DE102008061863A1 - Process for lamination of gray hair - Google Patents

Abstract

The present application relates to a process for the permanent dyeing of gray hair, in which - in a first step, the entire hair is treated with an oxidative dye (A) and - the subsequently regrown gray hair roots in one or more further steps with an agent (B ) are treated immediately before use. at least one agent (B1) which contains at least one reactive carbonyl compound in a cosmetic carrier, and. at least one agent (B2) containing in a cosmetic carrier at least one C, H-acidic compound selected from compounds of formula (CH-1) and / or compounds of formula (CH-2), $ F1 wherein - R6 is a linear or cyclic (C1 to C6) alkyl group, a (C2 to C6) alkenyl group, an optionally substituted aryl group, an optionally substituted heteroaryl group, an aryl (C1 to C6) alkyl group, a (C1 to C6) hydroxyalkyl group , a (C2 to C6) polyhydroxyalkyl group, a (C1 to C6) alkoxy (C1 to C6) alkyl group, a group RIRIIN- (CH2) m-, in which RI and RII independently of one another represent a hydrogen atom, a C1 to C4) alkyl group, a (C1 to C4) hydroxyalkyl group or an aryl (C1 to C6) alkyl group, wherein RI and RII together with the nitrogen atom can form a 5-, 6- or 7-membered ring and m stands for a number 2, 3, 4, 5 or 6, - R7 ...

Description

The The present invention relates to a process for permanent coloration gray hair, in which the hair is first dyed oxidatively and the regrown hairlines later with a special aftertreatment agent based on reactive Carbonyl compounds and C, H-acidic compounds colored be a method of coloring Asian Asian Hair, the use of the special aftertreatment agent as well corresponding dyeing kits.

Human Hair is used today in a variety of ways with hair cosmetics Treated preparations. These include cleaning hair with shampoos, care and regeneration with rinses and cures, as well as the bleaching, dyeing and shaping of the Hair with coloring, tinting, waving and styling preparations. There are funds for change or nuancing the color of the head hair a prominent role.

The Change in the coloring of the hair represents one important area of modern cosmetics. This can change the appearance the hair both current fashion trends and the individual wishes of the individual person to be adjusted. There is also a desire to preserve the natural Hair color even in old age and thus means for lamination of gray hair among consumers more pronounced.

conventional Hair dyes contain as color-changing Active ingredients usually at least one developer and / or at least a coupler components and optionally direct dyes as a nuance. Coupler and developer components are also known as Oxidation dye precursors referred.

In front Their application to human hair usually becomes Hair dyes in solid or pasty form with a dilute aqueous hydrogen peroxide solution mixed. The resulting mixture is then applied to the hair and rinsed out again after a certain exposure time. The duration of exposure to the hair to achieve a complete Coloring is usually between about 30 and 40 minutes.

Around to achieve a sufficient coloring effect are the ready to use Colorants usually adjusted strongly alkaline, the pH is between 8 and 10.5. Such high pH values are required to open the outer To ensure cuticle (cuticle) and thus a Penetration of the active species (hydrogen peroxide) into the hair enable.

by virtue of the strongly alkaline conditions and the use of hydrogen peroxide It may be related to the color-changing process come to irritation of the scalp. These are both during the action of the color-changing agent as well as in the Follow the treatment.

Furthermore the usual hair dyeing techniques have the disadvantage that at the hairline after a few days again a gray Offspring occurs, especially in the forehead and apex area unpleasant.

Accordingly In the past, various techniques have been developed to freshly regrown gray hairline to conceal.

To the one of the freshly grown hairline targeted a renewed be subjected to oxidative staining. This technique allows a durable and stable lamination, but is tedious and may have the disadvantages described above (hair damage, Scalp irritation) with it.

A other, especially in the Asian countries popular technology is the treatment of the graying hair approaches with remedies based on direct dyes. In doing so, in particular anionic substantive substances used. This technique allows a simple concealment of gray approaches, however has only a very poor authenticity and already after some Hair washes must be repeated. Besides that is when using anionic substantive dyes frequently to observe an intensive staining of the scalp.

Accordingly, there is still the need for a staining technique that is durable Lamination of gray hair allows without the disadvantages mentioned. This need exists especially for Asian gray hair. For one thing, Asian hair has a different hair structure than European hair and is much harder to dye. On the other hand, the colorants must allow intense black nuances with excellent opacity, so that the dyed hairs differ as little as possible in color from the other areas of the hair.

task The present invention thus provided the provision of a dyeing process, which allows a permanent coloring of gray hair. At the same time an irritation of the scalp, a damage Hair and staining of the scalp as much as possible be avoided.

in the Framework of the underlying this application could work now surprisingly found that a method in which the hair is first dyed oxidatively and the regrowing hair extensions afterwards with a colorant based on reactive carbonyl compounds and C, H-acidic compounds are colored, not to the above adverse effects.

• – in einem ersten Schritt die gesamten Haare mit einem oxidativen Färbemittel (A) behandelt werden und
• – die anschließend nachgewachsenen grauen Haaransätze in einem oder mehreren weiteren Schritten mit einem Mittel (B) behandelt werden, das unmittelbar vor der Anwendung aus • mindestens einem Mittel (B1), das in einem kosmetischen Träger mindestens eine reaktive Carbonylverbindung enthält, und • mindestens einem Mittel (B2), das in einem kosmetischen Träger mindestens eine C,H-acide Verbindung ausgewählt aus Verbindungen der Formel (CH-1) und/oder Verbindungen der Formel (CH-2) enthält,
  
  worin – R⁶ steht für eine lineare oder cyclische (C₁ bis C₆)-Alkylgruppe, eine (C₂ bis C₆)-Alkenylgruppe, eine gegebenenfalls substituierte Arylgruppe, eine gegebenenfalls substituierte Heteroarylgruppe, eine Aryl-(C₁ bis C₆)-alkylgruppe, eine (C₁ bis C₆)-Hydroxyalkylgruppe, eine (C₂ bis C₆)-Polyhydroxyalkylgruppe, eine (C₁ bis C₆)-Alkoxy-(C₁ bis C₆)-alkylgruppe, eine Gruppe R^IR^IIN-(CH₂)_m-, worin R^I und R^II stehen unabhängig voneinander für ein Wasserstoffatom, eine (C₁ bis C₄)-Alkylgruppe, eine (C₁ bis C₄)-Hydroxyalkylgruppe oder eine Aryl-(C₁ bis C₆)-alkylgruppe, wobei R^I und R^II gemeinsam mit dem Stickstoffatom einen 5-, 6- oder 7-gliedrigen Ring bilden können und m steht für eine Zahl 2, 3, 4, 5 oder 6, – R⁷ steht für eine (C₁ bis C₆)-Alkylgruppe, insbesondere für eine Methylgruppe, – X^– steht für ein physiologisch verträgliches Anion, – der Zyklus der Formel (CH-1) repräsentiert alle Ringstrukturen, die zusätzlich weitere Heteroatome wie Stickstoff, Sauerstoff oder Schwefel enthalten können und ferner ankondensierte Ringstrukturen tragen können, wobei alle diese Ringsstrukturen zusätzliche Substituenten tragen können, – Het steht für einen gegebenenfalls substituierten Heteroaromaten, und – X¹ steht für eine direkte Bindung oder eine Carbonylgruppe,

durch Mischung erhalten wird.A first object of the present invention is therefore a process for the permanent coloring of gray hair, in which

• - In a first step, the entire hair with an oxidative dye (A) are treated and
• The subsequently regrown gray hair roots are treated in one or more further steps with an agent (B) which, immediately before use, comprises at least one agent (B1) which contains at least one reactive carbonyl compound in a cosmetic carrier and at least one Composition (B2) which contains in a cosmetic carrier at least one C, H-acidic compound selected from compounds of the formula (CH-1) and / or compounds of the formula (CH-2),
  
  wherein - R ⁶ represents a linear or cyclic (C ₁ to C ₆ ) alkyl group, a (C ₂ to C ₆ ) alkenyl group, an optionally substituted aryl group, an optionally substituted heteroaryl group, an aryl (C ₁ to C ₆ ) alkyl group, a (C ₁ to C ₆ ) hydroxyalkyl group, a (C ₂ to C ₆ ) polyhydroxyalkyl group, a (C ₁ to C ₆ ) alkoxy (C ₁ to C ₆ ) alkyl group, a group R ^I R ^{II is} N- (CH ₂ ) _m -, in which R ^I and R ^II independently of one another represent a hydrogen atom, a (C ₁ to C ₄ ) -alkyl group, a (C ₁ to C ₄ ) -hydroxyalkyl group or an aryl- (C ₁ to C ₆ ) -alkyl group, wherein R ^I and R ^II together with the nitrogen atom can form a 5-, 6- or 7-membered ring and m is a number 2, 3, 4, 5 or 6, - R ⁷ is a (C ₁ to C ₆ ) -alkyl group, in particular a methyl group, - X ^- is a physiologically acceptable anion, - the cycle of the formula (CH-1) represents all ring structures, the additional lic h may contain further heteroatoms such as nitrogen, oxygen or sulfur and may further carry fused ring structures, all of these ring structures being able to carry additional substituents, - Het is an optionally substituted heteroaromatic, and - X ¹ is a direct bond or a carbonyl group,

obtained by mixing.

The inventive method is composed of 2 or more treatment steps together. The phrase "the subsequently regrown gray hairlines treated in one or more further steps with an agent (B) be "according to the invention to be understood as that the second treatment step can take place only when already a newly regrown hairline can be seen. According to the invention preferred it is when the time interval between the oxidative staining and the treatment of the regrown hairs at least 5 days.

Further, the phrase "the subsequently regrown gray hairlines in one or more of the above several further steps are treated with an agent (B) ", it being understood that at the time at which, after the aftertreatment, a gray hairline is visible again, the treatment with the agent (B) can be repeated.

Also the time interval between two consecutive treatments with the agent (B) is preferred according to the invention at least 5 days.

All in all the treatment with the agent (B) according to the invention in principle be repeated as often as a gray hairline visible becomes. However, it is preferred according to the invention after 3, 4, 5 or 6 post-treatments with the agent (B) the staining procedure complete and complete the entire fibers again undergo oxidative staining.

in the Within the scope of the method according to the invention the hair in a first step with an oxidative dye (A) treated.

The oxidative colorant (A) preferably contains at least an oxidation dye precursor.

When Oxidation dye precursor contain within the scope of the invention Method used (A) preferably at least one Entwickierkomponente.

wobei
– G¹ steht für ein Wasserstoffatom, einen (C₁ bis C₄)-Alkylrest, einen (C₁ bis C₄)-Monohydroxyalkylrest, einen (C₂ bis C₄)-Polyhydroxyalkylrest, einen (C₁ bis C₄)-Alkoxy-(C₁ bis C₄)-alkylrest, einen 4'-Aminophenylrest oder einen (C₁ bis C₄)-Alkylrest, der mit einer stickstoffhaltigen Gruppe, einem Phenyl- oder einem 4'-Aminophenylrest substituiert ist;
– G² steht für ein Wasserstoffatom, einen (C₁ bis C₄)-Alkylrest, einen (C₁ bis C₄)-Monohydroxyalkylrest, einen (C₂ bis C₄)-Polyhydroxyalkylrest, einen (C₁ bis C₄)-Alkoxy-(C₁ bis C₄)-alkylrest oder einen (C₁ bis C₄)-Alkylrest, der mit einer stickstoffhaltigen Gruppe substituiert ist;
– G³ steht für ein Wasserstoffatom, ein Halogenatom, wie ein Chlor-, Brom-, Iod- oder Fluoratom, einen (C₁ bis C₄)-Alkylrest, einen (C₁ bis C₄)-Monohydroxyalkylrest, einen (C₂ bis C₄)-Polyhydroxyalkylrest, einen (C₁ bis C₄)-Hydroxyalkoxyrest, einen (C₁ bis C₄)-Alkoxy-(C₁ bis C₄)-alkylrest, einen (C₁ bis C₄)-Acetylaminoalkoxyrest, einen Mesylamino-(C₁ bis C₄)-alkoxyrest oder einen (C₁ bis C₄)-Carbamoylaminoalkoxyrest;
– G⁴ steht für ein Wasserstoffatom, ein Halogenatom, einen (C₁ bis C₄)-Alkylrest oder einen (C₁ bis C₄)-Alkoxy-(C₁ bis C₄)-alkylrest, oder
– wenn G³ und G⁴ in ortho-Stellung zueinander stehen, können sie gemeinsam eine verbrückende α,ω-Alkylendioxogruppe, wie beispielsweise eine Ethylendioxygruppe bilden.It may be preferred according to the invention to use as the developer component a p-phenylenediamine derivative or one of its physiologically acceptable salts. Particular preference is given to p-phenylenediamine derivatives of the formula (E1)

in which
G ¹ represents a hydrogen atom, a (C ₁ to C ₄ ) -alkyl radical, a (C ₁ to C ₄ ) -monohydroxyalkyl radical, a (C ₂ to C ₄ ) -polyhydroxyalkyl radical, a (C ₁ to C ₄ ) - Alkoxy (C ₁ to C ₄ ) alkyl, 4'-aminophenyl or (C ₁ to C ₄ ) alkyl substituted with a nitrogen-containing group, a phenyl or a 4'-aminophenyl;
G ² represents a hydrogen atom, a (C ₁ to C ₄ ) -alkyl radical, a (C ₁ to C ₄ ) monohydroxyalkyl radical, a (C ₂ to C ₄ ) -polyhydroxyalkyl radical, a (C ₁ to C ₄ ) - Alkoxy (C ₁ to C ₄ ) alkyl or (C ₁ to C ₄ ) alkyl substituted with a nitrogen-containing group;
G ³ represents a hydrogen atom, a halogen atom, such as a chlorine, bromine, iodine or fluorine atom, a (C ₁ to C ₄ ) -alkyl radical, a (C ₁ to C ₄ ) -monohydroxyalkyl radical, a (C ₂ to C ₄ ) -polyhydroxyalkyl radical, a (C ₁ to C ₄ ) -hydroxyalkoxy radical, a (C ₁ to C ₄ ) -alkoxy- (C ₁ to C ₄ ) -alkyl radical, a (C ₁ to C ₄ ) -acetylaminoalkoxy radical, a mesylamino (C ₁ to C ₄ ) alkoxy or (C ₁ to C ₄ ) carbamoylaminoalkoxy;
G ⁴ represents a hydrogen atom, a halogen atom, a (C ₁ to C ₄ ) -alkyl radical or a (C ₁ to C ₄ ) -alkoxy (C ₁ to C ₄ ) -alkyl radical, or
When G ³ and G ⁴ are ortho to each other, they may together form a bridging α, ω-alkylenedioxy group, such as, for example, an ethylenedioxy group.

Particularly preferred p-phenylenediamines of formula (E1) are selected from one or more compounds of the group formed from p-phenylenediamine, p-toluenediamine, 2-chloro-p-phenylenediamine, 2,3-dimethyl-p-phenylenediamine , 2,6-dimethyl-p-phenylenediamine, 2,6-diethyl-p-phenylenediamine, 2,5-dimethyl-p-phenylenediamine, N, N-dimethyl-p-phenylenediamine, N, N-diethyl-p-phenylenediamine , N, N-dipropyl-p-phenylenediamine, 4-amino-3-methyl- (N, N-diethyl) -aniline, N, N-bis (β-hydroxyethyl) -p-phenylenediamine, 4-N, N Bis (β-hydroxyethyl) amino-2-methylaniline, 4-N, N-bis (β-hydroxyethyl) amino-2-chloroaniline, 2- (β-hydroxyethyl) -p-phenylenediamine, 2- ( α, β-dihydroxyethyl) -p-phenylenediamine, 2-fluoro-p-phenylenediamine, 2-isopropyl-p-phenylenediamine, N- (β-hydroxypropyl) -p-phenylenediamine, 2-hydroxymethyl-p-phenylenediamine, N, N Dimethyl 3-methyl-p-phenylenediamine, N, N- (ethyl, β-hydroxyethyl) -p-phenylenediamine, N- (β, γ-dihydroxypropyl) -p-phenylenediamine, N- (4'-aminophenyl) - p-phenylenediamine, N-phenyl-p-phenyle ndiamine, 2- (β-hydroxyethyloxy) -p-phenylenediamine, 2-methoxymethyl-p-phenylenediamine, 2- (β-acetylaminoethyloxy) -p-phenylenediene min, N- (β-methoxyethyl) -p-phenylenediamine, N- (4-amino-3-methylphenyl) -N- [3- (1H-imidazol-1-yl) propyl] amine, 5,8-diaminobenzo 1,4-dioxane and their physiologically acceptable salts.

Completely according to the invention Particularly preferred p-phenylenediamine derivatives of the formula (E1) are selected from at least one compound of the group p-phenylenediamine, p-toluenediamine, 2- (β-hydroxyethyl) -p-phenylenediamine, 2- (α, β-dihydroxyethyl) -p-phenylenediamine, N, N-bis (β-hydroxyethyl) -p-phenylenediamine, 2-methoxymethyl-p-phenylenediamine, N- (4-amino-3-methylphenyl) -N- [3- (1H-imidazol-1-yl) -propyl] amine, as well as the physiologically acceptable salts of these compounds.

It may be further preferred according to the invention as a developer component to use compounds that at least contain two aromatic nuclei containing amino and / or hydroxyl groups are substituted.

wobei:
– Z¹ und Z² stehen unabhängig voneinander für einen Hydroxyl- oder NH₂-Rest, der gegebenenfalls durch einen (C₁ bis C₄)-Alkylrest, durch einen (C₁ bis C₄)-Hydroxyalkylrest und/oder durch eine Verbrückung Y substituiert ist oder der gegebenenfalls Teil eines verbrückenden Ringsystems ist,
– die Verbrückung Y steht für eine Alkylengruppe mit 1 bis 14 Kohlenstoffatomen, wie beispielsweise eine lineare oder verzweigte Alkylenkette oder einen Alkylenring, die von einer oder mehreren stickstoffhaltigen Gruppen und/oder einem oder mehreren Heteroatomen wie Sauerstoff-, Schwefel- oder Stickstoffatomen unterbrochen oder beendet sein kann und eventuell durch einen oder mehrere Hydroxyl- oder (C₁ bis C₈)-Alkoxyreste substituiert sein kann, oder eine direkte Bindung,
– G⁵ und G⁶ stehen unabhängig voneinander für ein Wasserstoff- oder Halogenatom, einen (C₁ bis C₄)-Alkylrest, einen (C₁ bis C₄)-Monohydroxyalkylrest, einen (C₂ bis C₄)-Polyhydroxyalkylrest, einen (C₁ bis C₄)-Aminoalkylrest oder eine direkte Verbindung zur Verbrückung Y,
– G⁷, G⁸, G⁹, G¹⁰, G¹¹ und G¹² stehen unabhängig voneinander für ein Wasserstoffatom, eine direkte Bindung zur Verbrückung Y oder einen (C₁ bis C₄)-Alkylrest,
mit der Maßgabe, dass die Verbindungen der Formel (E2) nur eine Verbrückung Y pro Molekül enthalten.Among the binuclear developer components which can be used in the dyeing compositions according to the invention, mention may be made in particular of the compounds corresponding to the following formula (E2) and their physiologically tolerated salts:

in which:
- Z ¹ and Z ² independently of one another are a hydroxyl or NH ₂ radical which is optionally substituted by a (C ₁ to C ₄ ) -alkyl radical, by a (C ₁ to C ₄ ) -hydroxyalkyl radical and / or by a bridge Y is substituted or which is optionally part of a bridging ring system,
- The bridge Y is an alkylene group having 1 to 14 carbon atoms, such as a linear or branched alkylene chain or an alkylene ring interrupted or terminated by one or more nitrogen-containing groups and / or one or more heteroatoms such as oxygen, sulfur or nitrogen atoms may be substituted by one or more hydroxyl or (C ₁ to C ₈ ) alkoxy, or a direct bond,
G ⁵ and G ⁶ independently of one another represent a hydrogen or halogen atom, a (C ₁ to C ₄ ) -alkyl radical, a (C ₁ to C ₄ ) -monohydroxyalkyl radical, a (C ₂ to C ₄ ) -polyhydroxyalkyl radical, - (C ₁ to C ₄ ) -aminoalkyl radical or a direct compound for bridging Y,
G ⁷ , G ⁸ , G ⁹ , G ¹⁰ , G ¹¹ and G ¹² independently of one another represent a hydrogen atom, a direct bond to the bridge Y or a (C ₁ to C ₄ ) -alkyl radical,
with the proviso that the compounds of the formula (E2) contain only one bridge Y per molecule.

The used in formula (E2) substituents are analogous to the invention defined to the above statements.

preferred binuclear developer components of the formula (E2) are especially selected from at least one of the following: N, N'-bis (β-hydroxyethyl) -N, N'-bis- (4'-aminophenyl) -1,3-diamino-propan-2-ol, N, N'-bis (β-hydroxyethyl) -N, N'-bis (4'-aminophenyl) ethylenediamine, N, N'-bis (4'-aminophenyl) tetramethylenediamine, N, N'-bis (β-hydroxyethyl) -N, N'-bis- (4'-aminophenyl) tetramethylenediamine, N, N'-bis (4- (methylamino) phenyl) tetramethylenediamine, N, N'-diethyl-N, N'-bis (4'-amino-3'-methylphenyl) ethylenediamine, bis (2-hydroxy-5-aminophenyl) methane, N, N'-bis (4'-aminophenyl) -1,4-diazacycloheptane, N, N'-bis (2-hydroxy-5-aminobenzyl) -piperazine, N- (4'-aminophenyl) -p-phenylenediamine and 1,10-bis (2 ', 5'-diaminophenyl) -1,4,7,10-tetraoxadecane and their physiologically acceptable salts.

All particularly preferred binuclear developer components of the formula (E2) are selected from N, N'-bis (β-hydroxyethyl) -N, N'-bis (4-aminophenyl) -1,3-diamino-propan-2-ol, Bis (2-hydroxy-5-aminophenyl) methane, 1,3-bis (2,5-diaminophenoxy) -propan-2-ol, N, N'-bis (4-aminophenyl) -1,4-diazacycloheptane, 1,10-bis (2,5-diaminophenyl) -1,4,7,10-tetraoxadecane or one of the physiologically acceptable salts of these compounds.

wobei:
– G¹³ steht für ein Wasserstoffatom, ein Halogenatom, einen (C₁ bis C₄)-Alkylrest, einen (C₁ bis C₄)-Monohydroxyalkylrest, einen (C₂ bis C₄)-Polyhydroxyalkylrest, einen (C₁ bis C₄)-Alkoxy-(C₁ bis C₄)-alkylrest, einen (C₁ bis C₄)-Aminoalkylrest, einen Hydroxy-(C₁ bis C₄)-alkylaminorest, einen (C₁ bis C₄)-Hydroxyalkoxyrest, einen (C₁ bis C₄)-Hydroxyalkyl-(C₁ bis C₄)-aminoalkylrest oder einen (Di-[(C₁ bis C₄)-alkyl]amino)-(C₁ bis C₄)-alkylrest, und
– G¹⁴ steht für ein Wasserstoff- oder Halogenatom, einen (C₁ bis C₄)-Alkylrest, einen (C₁ bis C₄)-Monohydroxyalkylrest, einen (C₂ bis C₄)-Polyhydroxyalkylrest, einen (C₁ bis C₄)-Alkoxy-(C₁ bis C₄)-alkylrest, einen (C₁ bis C₄)-Aminoalkylrest oder einen (C₁ bis C₄)-Cyanoalkylrest,
– G¹⁵ steht für Wasserstoff, einen (C₁ bis C₄)-Alkylrest, einen (C₁ bis C₄)-Monohydroxyalkylrest, einen (C₂ bis C₄)-Polyhydroxyalkylrest, einen Phenylrest oder einen Benzylrest, und
– G¹⁶ steht für Wasserstoff oder ein Halogenatom.Furthermore, it may be preferred according to the invention to use as the developer component a p-aminophenol derivative or one of its physiologically tolerable salts. Particular preference is given to p-aminophenol derivatives of the formula (E3)

in which:
G ¹³ represents a hydrogen atom, a halogen atom, a (C ₁ to C ₄ ) -alkyl radical, a (C ₁ to C ₄ ) monohydroxyalkyl radical, a (C ₂ to C ₄ ) -polyhydroxyalkyl radical, a (C ₁ to C ₄ ) alkoxy (C ₁ to C ₄ ) alkyl, (C ₁ to C ₄ ) aminoalkyl, hydroxy (C ₁ to C ₄ ) alkylamino, (C ₁ to C ₄ ) hydroxyalkoxy, a (C ₁ to C ₄ ) hydroxyalkyl (C ₁ to C ₄ ) aminoalkyl radical or a (di - [(C ₁ to C ₄ ) alkyl] amino) - (C ₁ to C ₄ ) alkyl radical, and
G ¹⁴ is a hydrogen or halogen atom, a (C ₁ to C ₄ ) -alkyl radical, a (C ₁ to C ₄ ) -monohydroxyalkyl radical, a (C ₂ to C ₄ ) -polyhydroxyalkyl radical, a (C ₁ to C ₄ ) alkoxy (C ₁ to C ₄ ) -alkyl radical, a (C ₁ to C ₄ ) -aminoalkyl radical or a (C ₁ to C ₄ ) -cyanoalkyl radical,
G ¹⁵ is hydrogen, a (C ₁ to C ₄ ) -alkyl radical, a (C ₁ to C ₄ ) monohydroxyalkyl radical, a (C ₂ to C ₄ ) -polyhydroxyalkyl radical, a phenyl radical or a benzyl radical, and
- G ¹⁶ is hydrogen or a halogen atom.

The used in formula (E3) substituents are analogous to the invention defined to the above statements.

preferred p-aminophenols of the formula (E3) are in particular p-aminophenol, N-methyl-p-aminophenol, 4-amino-3-methyl-phenol, 4-amino-3-fluorophenol, 2-hydroxymethylamino-4-aminophenol, 4-amino-3-hydroxymethylphenol, 4-amino-2- (β-hydroxyethoxy) phenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethyl-phenol, 4-amino-2-aminomethylphenol, 4-amino-2- (β-hydroxyethyl-aminomethyl) -phenol, 4-amino-2- (α, β-dihydroxyethyl) -phenol, 4-amino-2-fluorophenol, 4-amino-2-chlorophenol, 4-amino-2,6-dichlorophenol, 4-amino-2- (diethyl-aminomethyl) -phenol and its physiological compatible salts.

All particularly preferred compounds of the formula (E3) are p-aminophenol, 4-amino-3-methylphenol, 4-amino-2-aminomethylphenol, 4-amino-2- (α, β-dihydroxyethyl) phenol and 4-amino-2- (diethylaminomethyl) phenol.

Further For example, the developer component can be selected from o-aminophenol and its derivatives, such as 2-amino-4-methylphenol, 2-amino-5-methylphenol or 2-amino-4-chlorophenol.

Farther For example, the developer component may be selected from heterocyclic Developer components, such as pyrimidine derivatives, Pyrazole derivatives, pyrazolopyrimidine derivatives or their physiological compatible salts.

worin
– G¹⁷, G¹⁸ und G¹⁹ unabhängig voneinander für ein Wasserstoffatom, eine Hydroxygruppe, eine (C₁ bis C₄)-Alkoxygruppe oder eine Aminogruppe steht und
– G²⁰ für eine Hydroxygruppe oder eine Gruppe -NG²¹G²² steht, worin G²¹ und G²² unabhängig voneinander stehen für ein Wasserstoffatom, eine (C₁ bis C₄)-Alkylgruppe, eine (C₁ bis C₄)-Monohydroxyalkylgruppe,
mit der Maßgabe, dass maximal zwei der Gruppen aus G¹⁷, G¹⁸, G¹⁹ und G²⁰ eine Hydroxygruppe bedeuten und höchstens zwei der Reste G¹⁷, G¹⁸ und G¹⁹ für ein Wasserstoffatom stehen. Dabei ist es wiederum bevorzugt, wenn gemäß Formel (E4) mindestens zwei Gruppen aus G¹⁷, G¹⁸, G¹⁹ und G²⁰ für eine Gruppe -NG²¹G²² stehen und höchstens zwei Gruppen aus G¹⁷, G¹⁸, G¹⁹ und G²⁰ für eine Hydroxygruppe stehen.Preferred pyrimidine derivatives are selected according to the invention from compounds of the formula (E4) or their physiologically tolerated salts,

wherein
G ¹⁷ , G ¹⁸ and G ¹⁹ independently of one another represent a hydrogen atom, a hydroxy group, a (C ₁ to C ₄ ) alkoxy group or an amino group and
G ^{20 is} a hydroxy group or a group -NG ²¹ G ²² in which G ²¹ and G ²² independently of one another represent a hydrogen atom, a (C ₁ to C ₄ ) -alkyl group, a (C ₁ to C ₄ ) monohydroxyalkyl group .
with the proviso that a maximum of two of the groups of G ¹⁷ , G ¹⁸ , G ¹⁹ and G ^{20 is} a hydroxy group and at most two of the radicals G ¹⁷ , G ¹⁸ and G ^{19 are} a hydrogen atom. In this case, it is again preferred if, according to formula (E4), at least two groups of G ¹⁷ , G ¹⁸ , G ¹⁹ and G ^{20 represent} a group -NG ²¹ G ²² and at most two groups of G ¹⁷ , G ¹⁸ , G ¹⁹ and G ^{20 represent} a hydroxy group.

Especially preferred pyrimidine derivatives are in particular the compounds 2,4,5,6-tetraaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2-dimethylamino-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6-triaminopyrimidine.

worin
– G²³, G²⁴, G²⁵ stehen unabhängig voneinander für ein Wasserstoffatom, eine (C₁ bis C₄)-Alkylgruppe, eine (C₁ bis C₄)-Monohydroxyalkylgruppe, eine (C₂ bis C₄)-Polyhydroxyalkylgruppe, eine gegebenenfalls substituierte Arylgruppe oder eine gegebenenfalls substituierte Aryl-(C₁ bis C₄)-alkylgruppe, mit der Maßgabe dass, wenn G²⁵ für ein Wasserstoffatom steht, G²⁶ neben den vorgenannten Gruppen zusätzlich für eine Gruppe -NH₂ stehen kann,
– G²⁶ steht für ein Wasserstoffatom, eine (C₁ bis C₄)-Alkylgruppe, eine (C₁ bis C₄)-Monohydroxyalkylgruppe oder eine (C₂ bis C₄)-Polyhydroxyalkylgruppe und
– G²⁷ steht für ein Wasserstoffatom, eine gegebenenfalls substituierte Arylgruppe, eine (C₁ bis C₄)-Alkylgruppe oder eine (C₁ bis C₄)-Monohydroxyalkylgruppe, insbesondere für ein Wasserstoffatom oder eine Methylgruppe.Preferred pyrazole derivatives are selected according to the invention from compounds of the formula (E5),

wherein
G ²³ , G ²⁴ , G ²⁵ independently of one another represent a hydrogen atom, a (C ₁ to C ₄ ) -alkyl group, a (C ₁ to C ₄ ) -monohydroxyalkyl group, a (C ₂ to C ₄ ) -polyhydroxyalkyl group, a optionally substituted aryl group or an optionally substituted aryl- (C ₁ to C ₄ ) -alkyl group, with the proviso that when G ^{25 is} a hydrogen atom, G ^{26 may} additionally be a group -NH _{2 in} addition to the abovementioned groups,
G ²⁶ represents a hydrogen atom, a (C ₁ to C ₄ ) alkyl group, a (C ₁ to C ₄ ) monohydroxyalkyl group or a (C ₂ to C ₄ ) polyhydroxyalkyl group and
G ²⁷ represents a hydrogen atom, an optionally substituted aryl group, a (C ₁ to C ₄ ) -alkyl group or a (C ₁ to C ₄ ) -monohydroxyalkyl group, in particular a hydrogen atom or a methyl group.

Preferably in formula (E5) the radical -NG ²⁵ G ²⁶ binds to the 5 position and the radical G ²⁷ to the 3 position of the pyrazole cycle.

Especially preferred pyrazole derivatives are in particular the compounds which are selected from 4,5-diamino-1-methylpyrazole, 4,5-diamino-1- (β-hydroxyethyl) pyrazole, 3,4-diaminopyrazole, 4,5-diamino-1- (4'-chlorobenzyl) -pyrazole, 4,5-diamino-1,3-dimethylpyrazole, 4,5-diamino-3-methyl-1-phenylpyrazole, 4,5-diamino-1-methyl-3-phenylpyrazole, 4-amino-1,3-dimethyl-5-hydrazinopyrazole, 1-benzyl-4,5-diamino-3-methylpyrazole, 4,5-diamino-3-tert-butyl-1-methylpyrazole, 4,5-diamino-1-tert-butyl-3-methylpyrazole, 4,5-diamino-1- (β-hydroxyethyl) -3- methylpyrazole, 4,5-diamino-1-ethyl-3-methylpyrazole, 4,5-diamino-1-ethyl-3- (4'-methoxyphenyl) -pyrazole, 4,5-diamino-1-ethyl-3-hydroxymethylpyrazole, 4,5-diamino-3-hydroxymethyl-1-methylpyrazole, 4,5-diamino-3-hydroxymethyl-1-isopropylpyrazole, 4,5-diamino-3-methyl-1-isopropylpyrazole, 4-Amino-5- (β-aminoethyl) amino-1,3-dimethylpyrazole, as well their physiologically acceptable salts.

wobei:
– G²⁸, G²⁹ und G³⁰, G³¹ unabhängig voneinander stehen für ein Wasserstoffatom, einen (C₁ bis C₄)-Alkylrest, einen Aryl-Rest, einen (C₁ bis C₄)-Monohydroxyalkylrest, einen (C₂ bis C₄)-Polyhydroxyalkylrest einen (C₁ bis C₄)-Alkoxy-(C₁ bis C₄)-alkylrest, einen (C₁ bis C₄)-Aminoalkylrest, der gegebenenfalls durch ein Acetyl-Ureid- oder einen Sulfonyl-Rest geschützt sein kann, einen (C₁ bis C₄)-Alkylamino-(C₁ bis C₄)-alkylrest, einen Di-[(C₁ bis C₄)-alkyl]-(C₁ bis C₄)-aminoalkylrest, wobei die Dialkyl-Reste gegebenenfalls einen Kohlenstoffzyklus oder einen Heterozyklus mit 5 oder 6 Kettengliedern bilden, einen (C₁ bis C₄)-Monohydroxyalkyl- oder einen Di[(C₁ bis C₄)-Hydroxyalkyl]-(C₁ bis C₄)-aminoalkylrest,
– die X-Reste stehen unabhängig voneinander für ein Wasserstoffatom, einen (C₁ bis C₄)-Alkylrest, einen Aryl-Rest, einen (C₁ bis C₄)-Monohydroxyalkylrest, einen (C₂ bis C₄)-Polyhydroxyalkylrest, einen (C₁ bis C₄)-Aminoalkylrest, einen (C₁ bis C₄)-Alkylamino-(C₁ bis C₄)-alkylrest, einen Di-[(C₁ bis C₄)alkyl]-(C₁ bis C₄)-aminoalkylrest, wobei die Dialkyl-Reste gegebenenfalls einen Kohlenstoffzyklus oder einen Heterozyklus mit 5 oder 6 Kettengliedern bilden, einen (C₁ bis C₄)-Hydroxyalkyl- oder einen Di-[(C₁ bis C₄)-hydroxyalkyl]amino-(C₁ bis C₄)-alkylrest, einen Aminorest, einen (C₁ bis C₄)-Alkyl- oder Di-[(C₁ bis C₄)-hydroxyalkyl]aminorest, ein Halogenatom, eine Carboxylsäuregruppe oder eine Sulfonsäuregruppe,
– i hat den Wert 0, 1, 2 oder 3,
– p hat den Wert 0 oder 1,
– q hat den Wert 0 oder 1 und
– n hat den Wert 0 oder 1,
mit der Maßgabe, dass
– die Summe aus p + q ungleich 0 ist,
– wenn p + q gleich 2 ist, n den Wert 0 hat, und die Gruppen NG²⁸G²⁹ und NG³⁰G³¹ belegen die Positionen (2, 3); (5, 6); (6, 7); (3, 5) oder (3, 7);
– wenn p + q gleich 1 ist, n den Wert 1 hat, und die Gruppen NG²⁸G²⁹ (oder NG³⁰G³¹) und die Gruppe OH belegen die Positionen (2, 3); (5, 6); (6, 7); (3, 5) oder (3, 7);Preferred pyrazolopyrimidine derivatives are, in particular, the derivatives of the pyrazolo [1,5-a] pyrimidine of the following formula (E6) and its tautomeric forms, if a tautomeric equilibrium exists:

in which:
G ²⁸ , G ²⁹ and G ³⁰ , G ³¹ independently of one another represent a hydrogen atom, a (C ₁ to C ₄ ) -alkyl radical, an aryl radical, a (C ₁ to C ₄ ) -monohydroxyalkyl radical, a (C ₂ to C ₄ ) -polyhydroxyalkyl radical is a (C ₁ to C ₄ ) -alkoxy- (C ₁ to C ₄ ) -alkyl radical, a (C ₁ to C ₄ ) -aminoalkyl radical which is optionally substituted by an acetyl-ureide or a sulfonyl radical Rest may be protected, a (C ₁ to C ₄ ) alkylamino (C ₁ to C ₄ ) alkyl, a di - [(C ₁ to C ₄ ) alkyl] - (C ₁ to C ₄ ) aminoalkyl where the dialkyl radicals optionally have a carbon cycle or form a heterocycle having 5 or 6 chain members, a (C ₁ to C ₄ ) monohydroxyalkyl or a di [(C ₁ to C ₄ ) -hydroxyalkyl] - (C ₁ to C ₄ ) aminoalkyl radical,
The X radicals independently of one another represent a hydrogen atom, a (C ₁ to C ₄ ) -alkyl radical, an aryl radical, a (C ₁ to C ₄ ) monohydroxyalkyl radical, a (C ₂ to C ₄ ) -polyhydroxyalkyl radical, a (C ₁ to C ₄ ) aminoalkyl radical, a (C ₁ to C ₄ ) alkylamino (C ₁ to C ₄ ) alkyl radical, a di - [(C ₁ to C ₄ ) alkyl] - (C ₁ to C ₄ ) -aminoalkyl radical, where the dialkyl radicals optionally form a carbon cycle or a heterocycle having 5 or 6 chain members, a (C ₁ to C ₄ ) -hydroxyalkyl or a di - [(C ₁ to C ₄ ) -hydroxyalkyl] amino (C ₁ to C ₄ ) alkyl, an amino, a (C ₁ to C ₄ ) alkyl or di - [(C ₁ to C ₄ ) hydroxyalkyl] amino, a halogen atom, a carboxylic acid group or a sulfonic acid group .
- i has the value 0, 1, 2 or 3,
- p has the value 0 or 1,
- q has the value 0 or 1 and
- n has the value 0 or 1,
with the proviso that
The sum of p + q is not equal to 0,
If p + q equals 2, n has the value 0, and the groups NG ²⁸ G ²⁹ and NG ³⁰ G ³¹ occupy the positions (2, 3); (5, 6); (6, 7); (3, 5) or (3, 7);
If p + q is 1, n is 1, and the groups NG ²⁸ G ²⁹ (or NG ³⁰ G ³¹ ) and the group OH occupy the positions (2, 3); (5, 6); (6, 7); (3, 5) or (3, 7);

The used in formula (E7) substituents are analogous to the invention defined to the above statements.

When the pyrazolo [1,5-a] pyrimidine of the above formula (E6) contains a hydroxy group at one of the 2, 5 or 7 positions of the ring system, there is a tautomeric equilibrium shown, for example, in the following scheme:

• – Pyrazolo[1,5-a]pyrimidin-3,7-diamin;
• – 2,5-Dimethyl-pyrazolo[1,5-a]pyrimidin-3,7-diamin;
• – Pyrazolo[1,5-a]pyrimidin-3,5-diamin;
• – 2,7-Dimethyl-pyrazolo[1,5-a]pyrimidin-3,5-diamin;
• – 3-Aminopyrazolo[1,5-a]pyrimidin-7-ol;
• – 3-Aminopyrazolo[1,5-a]pyrimidin-5-ol;
• – 2-(3-Aminopyrazolo[1,5-a]pyrimidin-7-ylamino)-ethanol;
• – 2-(7-Aminopyrazolo[1,5-a]pyrimidin-3-ylamino)-ethanol;
• – 2-[(3-Aminopyrazolo[1,5-a]pyrimidin-7-yl)-(2-hydroxy-ethyl)-amino]-ethanol;
• – 2-[(7-Aminopyrazolo[1,5-a]pyrimidin-3-yl)-(2-hydroxy-ethyl)-amino]-ethanol;
• – 5,6-Dimethylpyrazolo[1,5-a]pyrimidin-3,7-diamin;
• – 2,6-Dimethylpyrazolo[1,5-a]pyrimidin-3,7-diamin;
• – 3-Amino-7-dimethylamino-2,5-dimethylpyrazolo[1,5-a]pyrimidin;

sowie ihre physiologisch verträglichen Salze und ihre tautomeren Formen, wenn ein tautomers Gleichgewicht vorhanden ist.In particular, among the pyrazolo [1,5-a] pyrimidines of the above formula (E7):

• - pyrazolo [1,5-a] pyrimidine-3,7-diamine;
• 2,5-dimethylpyrazolo [1,5-a] pyrimidine-3,7-diamine;
• - pyrazolo [1,5-a] pyrimidine-3,5-diamine;
• 2,7-dimethylpyrazolo [1,5-a] pyrimidine-3,5-diamine;
• 3-aminopyrazolo [1,5-a] pyrimidin-7-ol;
• 3-aminopyrazolo [1,5-a] pyrimidin-5-ol;
• 2- (3-aminopyrazolo [1,5-a] pyrimidin-7-ylamino) ethanol;
• - 2- (7-aminopyrazolo [1,5-a] pyrimidin-3-ylamino) ethanol;
• - 2 - [(3-aminopyrazolo [1,5-a] pyrimidin-7-yl) - (2-hydroxy-ethyl) -amino] -ethanol;
• - 2 - [(7-aminopyrazolo [1,5-a] pyrimidin-3-yl) - (2-hydroxy-ethyl) -amino] -ethanol;
• 5,6-dimethylpyrazolo [1,5-a] pyrimidine-3,7-diamine;
• - 2,6-dimethylpyrazolo [1,5-a] pyrimidine-3,7-diamine;
• 3-amino-7-dimethylamino-2,5-dimethylpyrazolo [1,5-a] pyrimidine;

and their physiologically acceptable salts and their tautomeric forms when a tautomeric equilibrium is present.

The Pyrazolo [1,5-a] pyrimidines of the above formula (E6) can as described in the literature by cyclization starting from an aminopyrazole or hydrazine.

Very particularly preferred developer components are selected from at least one compound from the group formed from p-phenylenediamine, p-toluenediamine, 2- (β-hydroxyethyl) -p-phenylenediamine, 2- (α, β-dihydroxyethyl) -p phenylenediamine, N, N-bis (β-hydroxyethyl) -p-phenylenediamine, N- (4-amino-3-methylphenyl) -N- [3- (1H-imidazol-1-yl) propyl] amine, N , N'-bis (β-hydroxyethyl) -N, N'-bis- (4-ami nophenyl) -1,3-diamino-propan-2-ol, bis (2-hydroxy-5-aminophenyl) -methane, 1,3-bis (2,5-diaminophenoxy) -propan-2-ol, N , N'-bis (4-aminophenyl) -1,4-diazacycloheptane, 1,10-bis (2,5-diaminophenyl) -1,4,7,10-tetraoxadecane, p-aminophenol, 4-amino 3-methylphenol, 4-amino-2-aminomethylphenol, 4-amino-2- (α, β-dihydroxyethyl) phenol and 4-amino-2- (diethylaminomethyl) -phenol, 4,5-diamino-1- (β -hydroxyethyl) pyrazole, 2,4,5,6-tetraaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, and the physiologically acceptable salts of these compounds.

The following are examples of the radicals mentioned as substituents of the compounds of the formulas (E1) to (E6): Examples of (C ₁ to C ₄ ) -alkyl radicals are the groups -CH ₃ , -CH ₂ CH ₃ , -CH ₂ CH ₂ CH ₃ , -CH (CH ₃ ) ₂ , -CH ₂ CH ₂ CH ₂ CH ₃ , -CH ₂ CH (CH ₃ ) ₂ , -CH (CH ₃ ) CH ₂ CH ₃ , -C (CH ₃ ) ₃ . Examples of (C ₁ to C ₄ ) -alkoxy radicals according to the invention are -OCH ₃ , -OCH ₂ CH ₃ , -OCH ₂ CH ₂ CH ₃ , -OCH (CH ₃ ) ₂ , -OCH ₂ CH ₂ CH ₂ CH ₃ , OCH ₂ CH (CH ₃ ) ₂ , -OCH (CH ₃ ) CH ₂ CH ₃ , -OC (CH ₃ ) ₃ , in particular a methoxy or an ethoxy group.

Furthermore, as preferred examples of a (C ₁ to C ₄ ) monohydroxyalkyl group, -CH ₂ OH, -CH ₂ CH ₂ OH, -CH ₂ CH ₂ CH ₂ OH, -CHCH (OH) CH ₃ , -CH ₂ CH ₂ CH ₂ CH ₂ OH, with the group -CH ₂ CH ₂ OH being preferred.

A particularly preferred example of a (C ₂ to C ₄ ) polyhydroxyalkyl group is the 1,2-dihydroxyethyl group.

Examples for halogen atoms are F, Cl or Br atoms, Cl atoms are very particularly preferred examples.

Examples of nitrogen-containing groups are in particular -NH ₂ , (C ₁ to C ₄ ) -monoalkylamino groups, (C ₁ to C ₄ ) -dialkylamino groups, (C ₁ to C ₄ ) -trialkylammonium groups, (C ₁ to C ₄ ) -monohydroxyalkylamino groups, Imidazolinium and -NH ₃ ⁺

Examples of (C ₁ to C ₄ ) monoalkylamino groups are -NHCH ₃ , -NHCH ₂ CH ₃ , -NHCH ₂ CH ₂ CH ₃ , -NHCH (CH ₃ ) ₂ .

Examples of (C ₁ to C ₄ ) -dialkylamino group are -N (CH ₃ ) ₂ , -N (CH ₂ CH ₃ ) ₂ .

Examples of (C ₁ to C ₄ ) trialkylammonium groups are -N ⁺ (CH ₃ ) ₃ , -N ⁺ (CH ₃ ) ₂ (CH ₂ CH ₃ ), -N ⁺ (CH ₃ ) (CH ₂ CH ₃ ) ₂ ,

Examples of (C ₁ to C ₄ ) -hydroxyalkylamino radicals are -NH-CH ₂ CH ₂ OH, -NH-CH ₂ CH ₂ OH, -NH-CH ₂ CH ₂ CH ₂ OH, -NH-CH ₂ CH ₂ CH ₂ OH.

Examples of (C ₁ to C ₄ ) alkoxy (C ₁ to C ₄ ) alkyl groups are the groups -CH ₂ CH ₂ -O-CH ₃ , -CH ₂ CH ₂ CH ₂ -O-CH ₃ , -CH ₂ CH ₂ -O-CH ₂ CH ₃ , -CH ₂ CH ₂ CH ₂ -O-CH ₂ CH ₃ , -CH ₂ CH ₂ -O-CH (CH ₃ ), -CH ₂ CH ₂ CH ₂ -O- CH (CH ₃ ).

Examples of hydroxy (C ₁ to C ₄ ) alkoxy radicals are -O-CH ₂ OH, -O-CH ₂ CH ₂ OH, -O-CH ₂ CH ₂ CH ₂ OH, -O-CHCH (OH) CH ₃ , -O-CH ₂ CH ₂ CH ₂ CH ₂ OH.

Examples of (C ₁ to C ₄ ) -acetylaminoalkoxy radicals are -O-CH ₂ NHC (O) CH ₃ , -O-CH ₂ CH ₂ NHC (O) CH ₃ , -O-CH ₂ CH ₂ CH ₂ NHC (O ) CH ₃ , -O-CH ₂ CH (NHC (O) CH ₃ ) CH ₃ , -O-CH ₂ CH ₂ CH ₂ CH ₂ NHC (O) CH ₃ . Examples of (C ₁ to C ₄ ) -carbamoylaminoalkoxy radicals are -O-CH ₂ CH ₂ -NH-C (O) -NH ₂ , -O-CH ₂ CH ₂ CH ₂ -NH-C (O) -NH ₂ , O-CH ₂ CH ₂ CH ₂ CH ₂ -NH-C (O) -NH ₂ .

Examples of (C ₁ to C ₄ ) -aminoalkyl radicals are -CH ₂ NH ₂ , -CH ₂ CH ₂ NH ₂ , -CH ₂ CH ₂ CH ₂ NH ₂ , -CH ₂ CH (NH ₂ ) CH ₃ , -CH ₂ CH ₂ CH ₂ CH ₂ NH ₂ .

Examples of (C ₁ to C ₄ ) -cyanoalkyl radicals are -CH ₂ CN, -CH ₂ CH ₂ CN, -CH ₂ CH ₂ CH ₂ CN.

Examples of (C ₁ to C ₄ ) -hydroxyalkylamino (C ₁ to C ₄ ) -alkyl radicals are -CH ₂ CH ₂ NH-CH ₂ CH ₂ OH, -CH ₂ CH ₂ CH ₂ NH-CH ₂ CH ₂ OH, -CH ₂ CH ₂ NH-CH ₂ CH ₂ CH ₂ OH, -CH ₂ CH ₂ CH ₂ NH-CH ₂ CH ₂ CH ₂ OH. Examples of di [(C ₁ to C ₄ ) -hydroxyalkyl] amino (C ₁ to C ₄ ) -alkyl radicals are -CH ₂ CH ₂ N (CH ₂ CH ₂ OH) ₂ , -CH ₂ CH ₂ CH ₂ N ( CH ₂ CH ₂ OH) ₂ , -CH ₂ CH ₂ N (CH ₂ CH ₂ CH ₂ OH) ₂ , -CH ₂ CH ₂ CH ₂ N (CH ₂ CH ₂ CH ₂ OH) ₂ . An example of aryl groups is the phenyl group.

Examples of aryl (C ₁ to C ₄ ) alkyl groups are the benzyl group and the 2-phenylethyl group.

The Developer components are preferred in an amount of 0.005 to 20 wt .-%, preferably 0.1 to 5 wt .-%, each based on the ready-to-use agent (A) is used.

The employed in the process according to the invention Agent (A) may be added to the developer component or instead of the developer component at least one coupler component.

Kupplerkomponenten do not form a significant part of the oxidative staining alone Coloring, but always need the present of developer components. Therefore, it is preferred according to the invention that when using at least one developer component in addition at least one coupler component is used.

Kupplerkomponenten For the purposes of the invention, at least one substitution of a chemical residue of the coupler by the oxidized form of the developer component. This forms a covalent bond between the coupler and the developer component out. Couplers are preferred cyclic compounds that participate in the cycle at least two groups selected from (i) optionally substituted amino groups and / or (ii) hydroxy groups. If the cyclic compound is a six-membered ring (preferably aromatic), so the said groups are preferably in the ortho position or meta position to each other.

• – m-Aminophenol und/oder dessen Derivate,
• – m-Diaminobenzol und/oder dessen Derivate,
• – o-Diaminobenzol und/oder dessen Derivate,
• – o-Aminophenolderivate, wie beispielsweise o-Aminophenol,
• – Naphthalinderivate mit mindestens einer Hydroxygruppe,
• – Di- beziehungsweise Trihydroxybenzol und/oder deren Derivate,
• – Pyridinderivate,
• – Pyrimidinderivate,
• – Monohydroxyindol-Derivate und/oder Monoaminoindol-Derivate,
• – Monohydroxyindolin-Derivate und/oder Monoaminoindolin-Derivate,
• – Pyrazolonderivate, wie beispielsweise 1-Phenyl-3-methylpyrazol-5-on,
• – Morpholinderivate wie beispielsweise 6-Hydroxybenzomorpholin oder 6-Amino-benzomorpholin,
• – Chinoxalinderivate wie beispielsweise 6-Methyl-1,2,3,4-tetrahydrochinoxalin,

Gemische aus zwei oder mehrer Verbindungen aus einer oder mehrerer dieser Klassen sind im Rahmen dieser Ausführungsform ebenso erfindungsgemäß.Coupler components according to the invention are preferably selected as at least one compound from one of the following classes:

• M-aminophenol and / or its derivatives,
• M-diaminobenzene and / or its derivatives,
• O-diaminobenzene and / or its derivatives,
• O-aminophenol derivatives, such as o-aminophenol,
• Naphthalene derivatives having at least one hydroxy group,
• Di- or trihydroxybenzene and / or derivatives thereof,
• - pyridine derivatives,
• - pyrimidine derivatives,
• Monohydroxyindole derivatives and / or monoamine indole derivatives,
• Monohydroxyindoline derivatives and / or monoaminoindoline derivatives,
• Pyrazolone derivatives such as 1-phenyl-3-methylpyrazol-5-one,
• Morpholine derivatives such as, for example, 6-hydroxybenzomorpholine or 6-aminobenzomorpholine,
• Quinoxaline derivatives such as 6-methyl-1,2,3,4-tetrahydroquinoxaline,

Mixtures of two or more compounds from one or more of these classes are also within the scope of this embodiment according to the invention.

worin
G¹ und G² unabhängig voneinander stehen für ein Wasserstoffatom, eine (C₁ bis C₄)-Alkylgruppe, eine (C₃ bis C₆)-Cycloalkylgruppe, eine (C₂ bis C₄)-Alkenylgruppe, eine (C₁ bis C₄)-Monohydroxyalkylgruppe, eine (C₂ bis C₄)-Polyhydroxyalkylgruppe, eine (C₂ bis C₄)-Perfluoracylgruppe, eine Aryl-(C₁ bis C₆)-alkylgruppe, eine Amino-(C₁ bis C₆)-alkylgruppe, eine (C₁ bis C₆)-Dialkylamino-(C₁ bis C₆)-alkylgruppe oder eine (C₁ bis C₆)-Alkoxy-(C₁ bis C₆)-alkylgruppe, wobei G¹ und G² gemeinsam mit dem Stickstoffatom einen fünfgliedrigen, sechsgliedrigen oder siebengliedrigen Ring bilden können, G³ und G⁴ unabhängig voneinander stehen für ein Wasserstoffatom, ein Halogenatom, eine (C₁ bis C₄)-Alkylgruppe, eine (C₁ bis C₄)-Alkoxygruppe, eine Hydroxygruppe, eine (C₁ bis C₄)-Monohydroxyalkylgruppe, eine (C₂ bis C₄)-Polyhydroxyalkylgruppe, eine Hydroxy-(C₁ bis C₄)-alkoxygruppe, eine (C₁ bis C₆)-Alkyox-(C₂ bis C₆)-alkoxygruppe, eine Arylgruppe oder eine Heteroarylgruppe.The m-aminophenols or derivatives thereof which can be used according to the invention are preferably selected from at least one compound of the formula (K1) and / or from at least one physiologically tolerated salt of a compound of the formula (K1),

wherein
G ¹ and G ² independently of one another represent a hydrogen atom, a (C ₁ to C ₄ ) -alkyl group, a (C ₃ to C ₆ ) -cycloalkyl group, a (C ₂ to C ₄ ) -alkenyl group, a (C ₁ to C ₄ ) monohydroxyalkyl group, a (C ₂ to C ₄ ) polyhydroxyalkyl group, a (C ₂ to C ₄ ) perfluoroacyl group, an aryl (C ₁ to C ₆ ) alkyl group, an amino (C ₁ to C ₆ ) alkyl group, a (C ₁ to C ₆ ) dialkylamino (C ₁ to C ₆ ) alkyl group or a (C ₁ to C ₆ ) alkoxy (C ₁ to C ₆ ) alkyl group, wherein G ¹ and G ² together with the nitrogen atom can form a five-membered, six-membered or seven-membered ring, G ³ and G ⁴ independently of one another represent a hydrogen atom, a halogen atom, a (C ₁ to C ₄ ) -alkyl group, a (C ₁ to C ₄ ) Alkoxy group, a hydroxy group pe, a (C ₁ to C ₄ ) monohydroxyalkyl group, a (C ₂ to C ₄ ) polyhydroxyalkyl group, a hydroxy (C ₁ to C ₄ ) alkoxy group, a (C ₁ to C ₆ ) alkoxy (C ₂ to C ₆ ) alkoxy group, an aryl group or a heteroaryl group.

Especially preferred m-aminophenol coupler components are selected from at least one compound from the group that is formed from m-aminophenol, 5-amino-2-methylphenol, N-cyclopentyl-3-aminophenol, 3-amino-2-chloro-6-methylphenol, 2-hydroxy-4-aminophenoxyethanol, 2,6-dimethyl-3-aminophenol, 3-trifluoroacetylamino-2-chloro-6-methylphenol, 5-amino-4-chloro-2-methylphenol, 5-amino-4-methoxy-2-methylphenol, 5- (2'-hydroxyethyl) amino-2-methylphenol, 3- (diethylamino) phenol, N-cyclopentyl-3-aminophenol, 1,3-dihydroxy-5- (methylamino) -benzene, 3-ethylamino-4-methylphenol, 2,4-dichloro-3-aminophenol and the physiological compatible salts of all the compounds mentioned above.

worin
G⁵, G⁶, G⁷ und G⁸ unabhängig voneinander stehen für ein Wasserstoffatom, eine (C₁ bis C₄)-Alkylgruppe, eine (C₃ bis C₆)-Cycloalkylgruppe, eine (C₂ bis C₄)-Alkenylgruppe, eine (C₁ bis C₄)-Monohydroxyalkylgruppe, eine (C₂ bis C₄)-Polyhydroxyalkylgruppe, eine (C₁ bis C₄)-Alkoxy-(C₁ bis C₄)-alkylgruppe, eine Aryl-(C₁ bis C₄)-alkylgruppe, eine Heteroaryl-(C₁ bis C₄)-alkylgruppe, eine (C₂ bis C₄)-Perfluoracylgruppe, oder gemeinsam mit dem Stickstoffatom einen fünfgliedrigen oder sechsgliedrigen Heterozyklus bilden
G⁹ und G¹⁰ unabhängig voneinander stehen für ein Wasserstoffatom, ein Halogenatom, eine (C₁ bis C₄)-Alkylgruppe, eine ω-(2,4-Diaminophenyl)-(C₁ bis C₄)-alkylgruppe, eine ω-(2,4-Diaminophenyloxy)-(C₁ bis C₄)-alkoxygruppe, eine (C₁ bis C₄)-Alkoxygruppe, eine Hydroxygruppe, eine (C₁ bis C₄)-Alkoxy-(C₂ bis C₄)-alkoxygruppe, eine Arylgruppe, eine Heteroarylgruppe, eine (C₁ bis C₄)-Monohydroxyalkylgruppe, eine (C₂ bis C₄)-Polyhydroxyalkylgruppe, eine Hydroxy-(C₁ bis C₄)-alkoxygruppe.The m-diaminobenzenes or derivatives thereof which can be used according to the invention are preferably selected from at least one compound of the formula (K2) and / or from at least one physiologically tolerated salt of a compound of the formula (K2),

wherein
G ⁵ , G ⁶ , G ⁷ and G ⁸ independently of one another represent a hydrogen atom, a (C ₁ to C ₄ ) -alkyl group, a (C ₃ to C ₆ ) -cycloalkyl group, a (C ₂ to C ₄ ) -alkenyl group , a (C ₁ to C ₄ ) monohydroxyalkyl group, a (C ₂ to C ₄ ) polyhydroxyalkyl group, a (C ₁ to C ₄ ) alkoxy (C ₁ to C ₄ ) alkyl group, an aryl (C ₁ to C ₄ ) alkyl group, a heteroaryl (C ₁ to C ₄ ) alkyl group, a (C ₂ to C ₄ ) perfluoroacyl group, or together with the nitrogen atom form a five-membered or six-membered heterocycle
G ⁹ and G ¹⁰ independently of one another represent a hydrogen atom, a halogen atom, a (C ₁ to C ₄ ) -alkyl group, an ω- (2,4-diaminophenyl) - (C ₁ to C ₄ ) -alkyl group, an ω- (2,4-diaminophenyloxy) - (C ₁ to C ₄ ) alkoxy group, a (C ₁ to C ₄ ) alkoxy group, a hydroxy group, a (C ₁ to C ₄ ) alkoxy (C ₂ to C ₄ ) alkoxy group, an aryl group, a heteroaryl group, a (C ₁ to C ₄ ) monohydroxyalkyl group, a (C ₂ to C ₄ ) polyhydroxyalkyl group, a hydroxy (C ₁ to C ₄ ) alkoxy group.

Especially preferred m-diaminobenzene coupler components are selected from at least one compound from the group that is formed from m-phenylenediamine, 2- (2,4-diaminophenoxy) ethanol, 1,3-bis (2,4-diaminophenoxy) propane, 1-Methoxy-2-amino-4- (2'-hydroxyethylamino) benzene, 1,3-bis (2,4-diaminophenyl) propane, 2,6-bis (2'-hydroxyethylamino) -1-methylbenzene, 2- ({3 - [(2-hydroxyethyl) amino] -4-methoxy-5-methylphenyl} amino) ethanol, 2 - ({3 - [(2-hydroxyethyl) amino] -2-methoxy-5-methylphenyl} amino) ethanol, 2 - ({3 - [(2-hydroxyethyl) amino] -4,5-dimethylphenyl} amino) ethanol, 2- [3-morpholin-4-yl-phenyl) -amino] -ethanol, 3-amino-4- (2-methoxy-ethoxy) -5-methyl-phenylamine, 1-amino-3-bis (2'-hydroxyethyl) aminobenzene and the physiological compatible salts of all the compounds mentioned above.

worin
G¹¹, G¹², G¹³ und G¹⁴ unabhängig voneinander stehen für ein Wasserstoffatom, eine (C₁ bis C₄)-Alkylgruppe, eine (C₃ bis C₆)-Cycloalkylgruppe, eine (C₂ bis C₄)-Alkenylgruppe, eine (C₁ bis C₄)-Monohydroxyalkylgruppe, eine (C₂ bis C₄)-Polyhydroxyalkylgruppe, eine (C₁ bis C₄)-Alkoxy-(C₁ bis C₄)-alkylgruppe, eine Aryl-(C₁ bis C₄)-alkylgruppe, eine Heteroaryl-(C₁ bis C₄)-alkylgruppe, eine (C₂ bis C₄)-Perfluoracylgruppe, oder gemeinsam mit dem Stickstoffatom einen fünfgliedrigen oder sechsgliedrigen Heterozyklus bilden
G¹⁵ und G¹⁶ unabhängig voneinander stehen für ein Wasserstoffatom, ein Halogenatom, eine Carboxylgruppe, eine (C₁ bis C₄)-Alkylgruppe, eine (C₁ bis C₄)-Alkoxygruppe, eine Hydroxygruppe, eine (C₁ bis C₄)-Monohydroxyalkylgruppe, eine (C₂ bis C₄)-Polyhydroxyalkylgruppe, eine Hydroxy-(C₁ bis C₄)-alkoxygruppe.The o-diaminobenzenes or their derivatives which can be used according to the invention are preferably selected from at least one compound of the formula (K3) and / or from at least one physiologically tolerated salt of a compound of the formula (K3),

wherein
G ¹¹ , G ¹² , G ¹³ and G ¹⁴ independently represent a hydrogen atom, a (C ₁ to C ₄ ) alkyl group, a (C ₃ to C ₆ ) cycloalkyl group, a (C ₂ to C ₄ ) alkenyl group , a (C ₁ to C ₄ ) monohydroxyalkyl group, a (C ₂ to C ₄ ) polyhydroxyalkyl group, a (C ₁ to C ₄ ) alkoxy (C ₁ to C ₄ ) alkyl group, an aryl (C ₁ to C ₄ ) alkyl group, a heteroaryl (C ₁ to C ₄ ) alkyl group, a (C ₂ to C ₄ ) perfluoroacyl group, or together with the nitrogen atom form a five-membered or six-membered heterocycle
G ¹⁵ and G ¹⁶ independently of one another represent a hydrogen atom, a halogen atom, a carboxyl group, a (C ₁ to C ₄ ) -alkyl group, a (C ₁ to C ₄ ) -alkoxy group, a hydroxy group, a (C ₁ to C ₄ ) Monohydroxyalkyl group, a (C ₂ to C ₄ ) polyhydroxyalkyl group, a hydroxy (C ₁ to C ₄ ) alkoxy group.

Especially preferred o-diaminobenzene coupler components are selected from at least one compound from the group that is formed from 3,4-diaminobenzoic acid and 2,3-diamino-1-methylbenzene and the physiologically acceptable salts of all above mentioned compounds.

preferred Di- or trihydroxybenzenes and their derivatives selected from at least one compound of the group, which is formed from resorcinol, resorcinol monomethyl ether, 2-methylresorcinol, 5-methylresorcinol, 2,5-dimethylresorcinol, 2-chlororesorcinol, 4-chlororesorcinol, Pyrogallol and 1,2,4-trihydroxybenzene.

worin
G¹⁷ und G¹⁸ stehen unabhängig voneinander für eine Hydroxygruppe oder eine Gruppe -NG²¹G²², worin G²¹ und G²² unabhängig voneinander stehen für ein Wasserstoffatom, eine (C₁ bis C₄)-Alkylgruppe, eine (C₃ bis C₆)-Cycloalkylgruppe, eine (C₂ bis C₄)-Alkenylgruppe, eine Arylgruppe, eine (C₁ bis C₄)- Monohydroxyalkylgruppe, eine (C₂ bis C₄)-Polyhydroxyalkylgruppe, eine (C₁ bis C₄)-Alkoxy-(C₁ bis C₄)-alkylgruppe, eine Aryl-(C₁ bis C₄)-alkylgruppe, eine Heteroaryl-(C₁ bis C₄)-alkylgruppe,
G¹⁹ und G²⁰ stehen unabhängig voneinander für ein Wasserstoffatom, ein Halogenatom, eine (C₁ bis C₄)-Alkylgruppe oder eine (C₁ bis C₄)-Alkoxygruppe.The pyridine derivatives which can be used according to the invention are preferably selected from at least one compound of the formula (K4) and / or from at least one physiologically tolerable salt of a compound of the formula (K4),

wherein
G ¹⁷ and G ¹⁸ independently of one another represent a hydroxy group or a group -NG ²¹ G ²² , in which G ²¹ and G ²² independently of one another represent a hydrogen atom, a (C ₁ to C ₄ ) -alkyl group, a (C ₃ to C ₆ ) -cycloalkyl group, a (C ₂ to C ₄ ) alkenyl group, an aryl group, a (C ₁ to C ₄ ) monohydroxyalkyl group, a (C ₂ to C ₄ ) -polyhydroxyalkyl group, a (C ₁ to C ₄ ) - Alkoxy (C ₁ to C ₄ ) alkyl group, an aryl (C ₁ to C ₄ ) alkyl group, a heteroaryl (C ₁ to C ₄ ) alkyl group,
G ¹⁹ and G ²⁰ independently of one another represent a hydrogen atom, a halogen atom, a (C ₁ to C ₄ ) -alkyl group or a (C ₁ to C ₄ ) -alkoxy group.

It is preferred if, according to formula (K4), the radicals G ¹⁷ and G ^{18 are} in the ortho position or in the meta position relative to one another.

Especially preferred pyridine derivatives are selected from at least a compound of the group formed from 2,6-dihydroxypyridine, 2-amino-3-hydroxypyridine, 2-amino-5-chloro-3-hydroxypyridine, 3-amino-2-methylamino-6-methoxypyridine, 2,6-dihydroxy-3,4-dimethylpyridine, 2,6-dihydroxy-4-methylpyridine, 2,6-diaminopyridine, 2,3-diamino-6-methoxypyridine, 3,5-diamino-2,6-dimethoxypyridine, 3,4-diaminopyridine, 2- (2-methoxyethyl) amino-3-amino-6-methoxypyridine, 2- (4'-methoxyphenyl) amino-3-aminopyridine, and the physiological acceptable salts of the aforementioned compounds.

preferred Naphthalene derivatives having at least one hydroxy group are selected from at least one compound of the group that is formed from 1-naphthol, 2-methyl-1-naphthol, 2-hydroxymethyl-1-naphthol, 2-hydroxyethyl-1-naphthol, 1,3-dihydroxynaphthalene, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 1,8-dihydroxynaphthalene, 2,7-dihydroxynaphthalene and 2,3-dihydroxynaphthalene.

worin
G²³ steht für ein Wasserstoffatom, eine (C₁ bis C₄)-Alkylgruppe, eine (C₃ bis C₆)-Cycloalkylgruppe, eine (C₂ bis C₄)-Alkenylgruppe, eine (C₁ bis C₄)-Monohydroxyalkylgruppe, eine (C₂ bis C₄)-Polyhydroxyalkylgruppe, eine Aryl-(C₁ bis C₄)-alkylgruppe,
G²⁴ steht für eine Hydroxygruppe oder eine Gruppe -NG²⁶G²⁷, worin G²⁶ und G²⁷ unabhängig voneinander stehen für ein Wasserstoffatom, eine (C₁ bis C₄)-Alkylgruppe, eine (C₃ bis C₆)-Cycloalkylgruppe, eine (C₂ bis C₄)-Alkenylgruppe, eine (C₁ bis C₄)-Monohydroxyalkylgruppe, eine (C₂ bis C₄)-Polyhydroxyalkylgruppe,
G²⁵ Wasserstoffatom, ein Halogenatom oder eine (C₁ bis C₄)-Alkylgruppe,
mit der Maßgabe, dass G²⁴ in meta-Position oder ortho-Position zum Strukturfragment NG²³ der Formel bindet.The indole derivatives which can be used according to the invention are preferably selected from at least one compound of the formula (K5) and / or from at least one physiologically tolerated salt of a compound of the formula (K5),

wherein
G ²³ represents a hydrogen atom, a C ₁ to C ₄ alkyl group, a C ₃ to C ₆ cycloalkyl group, a C ₂ to C ₄ alkenyl group, a C ₁ to C ₄ monohydroxyalkyl group , a (C ₂ to C ₄ ) polyhydroxyalkyl group, an aryl (C ₁ to C ₄ ) alkyl group,
G ²⁴ represents a hydroxy group or a group -NG ²⁶ G ²⁷ , in which G ²⁶ and G ²⁷ independently of one another represent a hydrogen atom, a (C ₁ to C ₄ ) -alkyl group, a (C ₃ to C ₆ ) -cycloalkyl group, a (C ₂ to C ₄ ) alkenyl group, a (C ₁ to C ₄ ) monohydroxyalkyl group, a (C ₂ to C ₄ ) polyhydroxyalkyl group,
G ^{25 is a} hydrogen atom, a halogen atom or a (C ₁ to C ₄ ) -alkyl group,
with the proviso that G ²⁴ binds in the meta position or ortho position to the structural fragment NG ^{23 of} the formula.

Especially Preferred indole derivatives are selected from at least a compound of the group formed from 4-hydroxyindole, 6-hydroxyindole and 7-hydroxyindole and the physiologically acceptable Salts of the aforementioned compounds.

worin
G²⁸ steht für ein Wasserstoffatom, eine (C₁ bis C₄)-Alkylgruppe, eine (C₃ bis C₆)-Cycloalkylgruppe, eine (C₂ bis C₄)-Alkenylgruppe, eine (C₁ bis C₄)-Monohydroxyalkylgruppe, eine (C₂ bis C₄)-Polyhydroxyalkylgruppe, eine Aryl-(C₁ bis C₄)-alkylgruppe,
G²⁹ steht für eine Hydroxygruppe oder eine Gruppe -NG³¹G³², worin G³¹ und G³² unabhängig voneinander stehen für ein Wasserstoffatom, eine (C₁ bis C₄)-Alkylgruppe, eine (C₃ bis C₆)-Cycloalkylgruppe, eine (C₂ bis C₄)-Alkenylgruppe, eine (C₁ bis C₄)-Monohydroxyalkylgruppe, eine (C₂ bis C₄)-Polyhydroxyalkylgruppe,
G³⁰ Wasserstoffatom, ein Halogenatom oder eine (C₁ bis C₄)-Alkylgruppe,
mit der Maßgabe, dass G²⁹ in meta-Position oder ortho-Position zum Strukturfragment NG²⁸ der Formel bindet.The indoline derivatives which can be used according to the invention are preferably selected from at least one compound of the formula (K6) and / or from at least one physiologically tolerable salt of a compound of the formula (K6),

wherein
G ²⁸ represents a hydrogen atom, a (C ₁ to C ₄ ) alkyl group, a (C ₃ to C ₆ ) cycloalkyl group, a (C ₂ to C ₄ ) alkenyl group, a (C ₁ to C ₄ ) monohydroxyalkyl group , a (C ₂ to C ₄ ) polyhydroxyalkyl group, an aryl (C ₁ to C ₄ ) alkyl group,
G ²⁹ represents a hydroxy group or a group -NG ³¹ G ³² , in which G ³¹ and G ³² independently of one another represent a hydrogen atom, a (C ₁ to C ₄ ) -alkyl group, a (C ₃ to C ₆ ) -cycloalkyl group, a (C ₂ to C ₄ ) alkenyl group, a (C ₁ to C ₄ ) monohydroxyalkyl group, a (C ₂ to C ₄ ) polyhydroxyalkyl group,
G ^{30 is a} hydrogen atom, a halogen atom or a (C ₁ to C ₄ ) -alkyl group,
with the proviso that G ²⁹ binds in the meta position or ortho position to the structural fragment NG ^{28 of} the formula.

Especially preferred indoline derivatives are selected from at least a compound of the group formed from 4-hydroxyindoline, 6-hydroxyindoline and 7-hydroxyindoline and the physiologically acceptable Salts of the aforementioned compounds.

preferred Pyrimidine derivatives are selected from at least one Compound of the group formed from 4,6-diaminopyrimidine, 4-amino-2,6-dihydroxypyrimidine, 2,4-diamino-6-hydroxypyrimidine, 2,4,6-trihydroxypyrimidine, 2-amino-4-methylpyrimidine, 2-amino-4-hydroxy-6-methylpyrimidine and 4,6-dihydroxy-2-methylpyrimidine and the physiologically acceptable Salts of the aforementioned compounds.

Particularly preferred coupler components according to the invention are selected from m-aminophenol, 5-amino-2-methylphenol, 3-amino-2-chloro-6-methylphenol, 2-hydroxy-4-aminophenoxyethanol, 5-amino-4-chloro-2-methylphenol , 5- (2'-hydroxyethyl) amino-2-methylphenol, 2,4-dichloro-3-aminophenol, o-aminophenol, m-phenylenediamine, 2- (2,4-diaminophenoxy) ethanol, 1,3-bis (2,4-diaminophenoxy) propane, 1-methoxy-2-amino-4- (2'-hydroxyethylamino) benzene, 1,3-bis (2,4-diaminophenyl) propane, 2,6-bis (2'-bis) hydroxyethylamino) -1-methylbenzene, 2 - ({3 - [(2-hydroxyethyl) amino] -4-methoxy-5-methylphenyl} amino) ethanol, 2 - ({3 - [(2-hydroxyethyl) amino] -2 -methoxy-5-methylphenyl} amino) ethanol, 2- ({3 - [(2-hydroxyethyl) amino] -4,5-dimethylphenyl} amino) ethanol, 2- [3-morpholin-4-ylphenyl) amino] ethanol , 3-amino-4- (2-methoxyethoxy) -5-methylphenylamine, 1-amino-3-bis (2'-hydroxyethyl) aminobenzene, resorcinol, 2-methylresorcinol, 4-chlororesorcinol, 1,2,4- Trihydroxybenzene, 2-amino-3-hydroxypyridine, 3-amino-2-methylamino-6-methoxypyridine, 2,6-Dihydroxy-3,4-dimethylpyridine, 3,5-diamino-2,6-dimethoxypyridine, 1-phenyl-3-methylpyrazol-5-one, 1-naphthol, 1,5-dihydroxynaphthalene, 2,7- Dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 1,8-dihydroxynaphthalene, 4-hydroxyindole, 6-hydroxyindole, 7-hydroxyindole, 4-hydroxyindoline, 6-hydroxyindoline, 7-hydroxyindoline or mixtures of these compounds or the physiologically acceptable salts of the abovementioned compounds.

In the following, examples of the substituents as the compounds of formulas (K1) to (K6) said radicals are enumerated: Examples of (C ₁ to C ₄₎ -alkyl, the groups -CH _3, -CH ₂ CH _3, -CH ₂ CH ₂ CH ₃ , -CH (CH ₃ ) ₂ , -CH ₂ CH ₂ CH ₂ CH ₃ , -CH ₂ CH (CH ₃ ) ₂ , -CH (CH ₃ ) CH ₂ CH ₃ , -C (CH ₃ ) ₃ .

Examples of (C ₃ to C ₆ ) cycloalkyl groups according to the invention are cyclopropyl, cyclopentyl and cyclohexyl.

Examples of (C ₁ to C ₄ ) -alkoxy radicals according to the invention are -OCH ₃ , -OCH ₂ CH ₃ , -OCH ₂ CH ₂ CH ₃ , -OCH (CH ₃ ) ₂ , -OCH ₂ CH ₂ CH ₂ CH ₃ , OCH ₂ CH (CH ₃ ) ₂ , -OCH (CH ₃ ) CH ₂ CH ₃ , -OC (CH ₃ ) ₃ , in particular a methoxy or an ethoxy group.

Furthermore, as preferred examples of a (C ₁ to C ₄ ) monohydroxyalkyl group, -CH ₂ OH, -CH ₂ CH ₂ OH, -CH ₂ CH ₂ CH ₂ OH, -CH ₂ CH (OH) CH ₃ , -CH ₂ CH ₂ CH ₂ CH ₂ OH, with the group -CH ₂ CH ₂ OH being preferred.

A particularly preferred example of a (C ₂ to C ₄ ) polyhydroxyalkyl group is the 1,2-dihydroxyethyl group.

Examples for halogen atoms are F, Cl or Br atoms, Cl atoms are very particularly preferred examples.

Examples of nitrogen-containing groups are in particular -NH ₂ , (C ₁ to C ₄ ) -monoalkylamino groups, (C ₁ to C ₄ ) -dialkylamino groups, (C ₁ to C ₄ ) -trialkylammonium groups, (C ₁ to C ₄ ) -monohydroxyalkylamino groups, Imidazolinium and -NH ₃ ⁺

Examples of (C ₁ to C ₄ ) monoalkylamino groups are -NHCH ₃ , -NHCH ₂ CH ₃ , -NHCH ₂ CH ₂ CH ₃ , -NHCH (CH ₃ ) ₂ .

Examples of (C ₁ to C ₄ ) -dialkylamino group are -N (CH ₃ ) ₂ , -N (CH ₂ CH ₃ ) ₂ .

Examples of (C ₁ to C ₄ ) alkoxy (C ₁ to C ₄ ) alkyl groups are the groups -CH ₂ CH ₂ -O-CH ₃ , -CH ₂ CH ₂ CH ₂ -O-CH ₃ , -CH ₂ CH ₂ -O-CH ₂ CH ₃ , -CH ₂ CH ₂ CH ₂ -O-CH ₂ CH ₃ , -CH ₂ CH ₂ -O-CH (CH ₃ ) ₂ , -CH ₂ CH ₂ CH ₂ -O -CH (CH ₃ ) ₂ .

Examples of (C ₁ to C ₄ ) alkoxy (C ₁ to C ₄ ) alkoxy groups are the groups -O-CH ₂ CH ₂ -O-CH ₃ , -O-CH ₂ CH ₂ CH ₂ -O-CH ₃ , -O-CH ₂ CH ₂ -O-CH ₂ CH ₃ , -O-CH ₂ CH ₂ CH ₂ -O-CH ₂ CH ₃ , -O-CH ₂ CH ₂ -O-CH (CH ₃ ) ₂ , -O-CH ₂ CH ₂ CH ₂ -O-CH (CH ₃ ) ₂ .

Examples of hydroxy (C ₁ to C ₄ ) alkoxy radicals are -O-CH ₂ OH, -O-CH ₂ CH ₂ OH, -O-CH ₂ CH ₂ CH ₂ OH, -O-CH ₂ CH (OH) CH ₃ , -O-CH ₂ CH ₂ CH ₂ CH ₂ OH.

Examples of (C ₁ to C ₄ ) -aminoalkyl radicals are -CH ₂ NH ₂ , -CH ₂ CH ₂ NH ₂ , -CH ₂ CH ₂ CH ₂ NH ₂ , -CH ₂ CH (NH ₂ ) CH ₃ , -CH ₂ CH ₂ CH ₂ CH ₂ NH ₂ .

One Example of aryl groups is the phenyl group, which also may be substituted.

Examples of aryl (C ₁ to C ₄ ) alkyl groups are the benzyl group and the 2-phenylethyl group.

The Coupler components are preferably present in an amount of 0.005 to 20 wt .-%, preferably 0.1 to 5 wt .-%, each based on the ready-to-use means (A).

In this case, developer components and coupler components are generally used in approximately molar amounts to each other. Although the molar use has proven to be expedient, so a certain excess of individual oxidation dye precursors is not detrimental, so that developer components and coupler components in a molar ratio of 1: 0.5 to 1: 3, in particular 1: 1 to 1: 2, can stand.

It may be preferred according to the invention, the agent (A) of the method according to the invention as a further Dye precursor to add a natural analog dye.

When Dye precursors of naturally-analogous dyes are preferably those Indoles and indolines were used, which selected at least two groups from hydroxy and / or or amino groups, preferably as a substituent at the six-ring, exhibit. These groups may have additional substituents wear, z. B. in the form of etherification or esterification of the hydroxy group or an alkylation of the amino group. In a further embodiment the colorants contain at least one indole and / or Indoline. Compositions according to the invention, contain the precursors of natural dyes, are preferred used as air-oxidative coloring agents. In this embodiment Therefore, the said compositions will not be associated with an additional Oxidizing agent added.

in der unabhängig voneinander

• – R¹ steht für Wasserstoff, eine C₁-C₄-Alkylgruppe oder eine C₁-C₄-Hydroxy-alkylgruppe,
• – R² steht für Wasserstoff oder eine -COOH-Gruppe, wobei die -COOH-Gruppe auch als Salz mit einem physiologisch verträglichen Kation vorliegen kann,
• – R³ steht für Wasserstoff oder eine C₁-C₄-Alkylgruppe,
• – R⁴ steht für Wasserstoff, eine C₁-C₄-Alkylgruppe oder eine Gruppe -CO-R⁶, in der R⁶ steht für eine C₁-C₄-Alkylgruppe, und
• – R⁵ steht für eine der unter R⁴ genannten Gruppen,

sowie physiologisch verträgliche Salze dieser Verbindungen mit einer organischen oder anorganischen Säure.Particularly suitable precursors of naturally-analogous hair dyes are derivatives of 5,6-dihydroxyindoline of the formula (RN1),

in the independently of each other

• R ¹ is hydrogen, a C ₁ -C ₄ -alkyl group or a C ₁ -C ₄ -hydroxy-alkyl group,
• R ² is hydrogen or a -COOH group, where the -COOH group may also be present as a salt with a physiologically compatible cation,
• R ³ is hydrogen or a C ₁ -C ₄ -alkyl group,
• R ⁴ is hydrogen, a C ₁ -C ₄ -alkyl group or a group -CO-R ⁶ , in which R ⁶ is a C ₁ -C ₄ -alkyl group, and
• R ⁵ is one of the groups mentioned under R ⁴ ,

and physiologically acceptable salts of these compounds with an organic or inorganic acid.

Especially preferred derivatives of indoline are the 5,6-dihydroxyindoline, N-methyl-5,6-dihydroxyindoline, N-ethyl-5,6-dihydroxyindoline, N-propyl-5,6-dihydroxyindoline, N-butyl-5,6-dihydroxyindoline and 5,6-dihydroxyindoline-2-carboxylic acid.

Especially noteworthy within this group are N-methyl-5,6-dihydroxyindoline, N-ethyl-5,6-dihydroxyindoline, N-propyl-5,6-dihydroxyindoline, N-butyl-5,6-dihydroxyindoline and in particular the 5,6-dihydroxyindoline.

in der unabhängig voneinander

• – R¹ steht für Wasserstoff, eine C₁-C₄-Alkylgruppe oder eine C₁-C₄-Hydroxyalkylgruppe,
• – R² steht für Wasserstoff oder eine -COOH-Gruppe, wobei die -COOH-Gruppe auch als Salz mit einem physiologisch verträglichen Kation vorliegen kann,
• – R³ steht für Wasserstoff oder eine C₁-C₄-Alkylgruppe,
• – R⁴ steht für Wasserstoff, eine C₁-C₄-Alkylgruppe oder eine Gruppe -CO-R⁶, in der R⁶ steht für eine C₁-C₄-Alkylgruppe, und
• – R⁵ steht für eine der unter R⁴ genannten Gruppen,
• – sowie physiologisch verträgliche Salze dieser Verbindungen mit einer organischen oder anorganischen Säure.

Derivatives of the 5,6-dihydroxyindole of the formula (RN2) are also outstandingly suitable as precursors of naturally-analogous hair dyes.

in the independently of each other

• R ¹ is hydrogen, a C ₁ -C ₄ -alkyl group or a C ₁ -C ₄ -hydroxyalkyl group,
• R ² is hydrogen or a -COOH group, where the -COOH group may also be present as a salt with a physiologically compatible cation,
• R ³ is hydrogen or a C ₁ -C ₄ -alkyl group,
• - R ⁴ is hydrogen, a C ₁ -C ₄ alkyl group or a group -CO-R ⁶ , in which R ⁶ is a C ₁ -C ₄ alkyl group, and
• R ⁵ is one of the groups mentioned under R ⁴ ,
• - As well as physiologically acceptable salts of these compounds with an organic or inorganic acid.

Especially preferred derivatives of indole are 5,6-dihydroxyindole, N-methyl-5,6-dihydroxyindole, N-ethyl-5,6-dihydroxyindole, N-propyl-5,6-dihydroxyindole, N-butyl-5,6-dihydroxyindole, 5,6-dihydroxyindole-2-carboxylic acid.

Within of this group are N-methyl-5,6-dihydroxyindole, N-ethyl-5,6-dihydroxyindole, N-propyl-5,6-dihydroxyindole, N-butyl-5,6-dihydroxyindole and especially the 5,6-dihydroxyindole.

The Indoline or the indole derivatives can both as free bases as well as in the form of their physiologically acceptable Salts with inorganic or organic acids, e.g. B. the hydrochlorides, sulfates and hydrobromides.

Farther can in the agent (A) additionally at least one more direct Dye be included. These are dyes that apply directly to the hair and do not use an oxidative process Need training of the paint. Direct dyes are usually nitrophenylenediamines, nitroaminophenols, Azo dyes, anthraquinones or indophenols.

The substantive dyes are each preferably in an amount from 0.001 to 20% by weight, based on the total application preparation, used. The total amount of substantive dyes is preferably at most 20% by weight.

Substantive Dyes can be anionic, cationic and nonionic substantive dyes are subdivided.

Anionic substantive dyes:

Particularly suitable anionic direct dyes are 6-hydroxy-5 - [(4-sulfophenyl) azo] -2-naphthalenesulfonic acid disodium salt (CI 15.985, Food Yellow No. 3, FD & C Yellow No. 6), 2,4-dinitro-1 naphthol-7-sulfonic acid disodium salt (CI 10,316, Acid Yellow 1, Food Yellow No. 1), 2- (indan-1,3-dion-2-yl) quinoline-x, x-sulfonic acid (mixture of mono- and di-sodium Disulfonic acid) (CI 47,005, D & C Yellow No. 10, Food Yellow No. 13, Acid Yellow 3, Yellow 10), 4 - ((4-amino-3-sulfophenyl) azo) benzenesulfonic acid disodium salt (CI 13,015, Acid Yellow 9 ), 5-hydroxy-1- (4-sulfophenyl) -4 - [(4-sulfophenyl) azo] pyrazole-3-carboxylic acid trisodium salt (CI 19.140, Food Yellow No. 4, Acid Yellow 23), 3 - [( 4-phenylamino) phenyl] azobenzenesulfonic acid, sodium salt (CI 13.065, Ki406, Acid Yellow 36), 9- (2-carboxyphenyl) -6-hydroxy-3H-xanthen-3-one (CI 45, 350; Acid Yellow 73, D & C Yellow No 8), 5 - [(2,4-dinitrophenyl) amino] -2-phenylaminobenzenesulfonic acid, sodium salt (CI 10,385; Acid Orange 3), 4 - [(2,4-dihydroxyphenyl) azo] -benzene cosulfonic acid sodium salt (CI 14,270; Acid Orange 6), 4 - [(2-hydroxynaphth-1-yl) azo] -benzenesulfonic acid, sodium salt (CI 15.510, Acid Orange 7), 4 - [(2,4-dihydroxy-3 - [(2,4-) dimethylphenyl) azo] -phenyl) azo] -benzenesulfonic acid, sodium salt (CI 20,170; Acid Orange 24), 4-hydroxy-3 - [(2-methoxyphenyl) azo] -1-naphthalenesulfonic acid, sodium salt (CI 14,710, Acid Red 4) , 4-hydroxy-3 - [(4-sulfonaphth-1-yl) azo] -1-naphthalenesulfonic acid disodium salt (CI 14,720; Acid Red No. 14), 6-hydroxy-5 - [(4-sulfonaphthalene) 1-yl) azo] -2,4-naphthalenedisulfonic acid trisodium salt (CI 16,255, Ponceau 4R, Acid Red 18), 3-hydroxy-4 - [(4-sulfonaphth-1-yl) azo] -2,7 -naphthalene-disulfonic acid trisodium salt (CI 16.185, Acid Red 27), 8-amino-1-hydroxy-2- (phenylazo) -3,6-naphthalene-disulfonic acid disodium salt (CI 17, 400; Acid Red 33; Acetylamino) -4-hydroxy-3 - [(2-methylphenyl) azo] -2,7-naphthalenedisulfonic acid disodium salt (CI 18.065, Acid Red 35), 2- (3-hydroxy-2,4,5,7 tetraiodedibenzopyran-6-on-9-yl) benzoic acid disodium salt (CI 45,430, Acid Red 51), N- [6- (D. iethylamino) -9- (2,4-disulfophenyl) -3H-xanthen-3-ylidene] -N-ethylethanammonium hydroxide, inner salt, sodium salt (CI 45, 100; Acid Red 52), 8 - [(4- (phenylazo) phenyl) azo] -7-naphthol-1,3-disulfonic acid disodium salt (CI 27.290; Acid Red 73), 2 ', 4', 5 ', 7' Tetrabromo-3 ', 6'-dihydroxyspiro [isobenzofuran-1 (3H), 9' - [9H] xanthene] -3-one disodium salt (CI 45.380; Acid Red 87), 2 ', 4', 5 ', 7'-Tetrabromo-4,5,6,7-tetrachloro-3 ', 6'-dihydroxyspiro [isobenzofuran-1 (3H), 9' [9H] xanthene] -3-one disodium salt (CI 45.410; Acid Red 92 ), 3 ', 6'-dihydroxy-4', 5'-diiodospiro [isobenzofuran-1 (3H), 9 '(9H) -xanthen] -3-one-disodium salt (CI 45425; Acid Red 95), 2- Hydroxy-3 - ((2-hydroxynaphth-1-yl) azo) -5-nitrobenzenesulfonic acid, sodium salt (CI 15,685; Acid Red 184), 3-hydroxy-4- (3-methyl-5-oxo-1-phenyl) 4,5-dihydro-1H-pyrazol-4-ylazo) -naphthalene-1-sulfonic acid sodium salt, chromium complex (Acid Red 195), 3-hydroxy-4 - [(4-methyl-2-sulfonphenyl) azo] -2 -naphthalenecarboxylic acid calcium salt (CI 15.850: 1, Pigment Red 57: 1), 3 - [(2,4-dimethyl-5-sulfophenyl) azo] -4-hydroxy-1-naphthalenesulfonic acid dinatri Salt (CI 14,700, Food Red No. 1, Ponceau SX, FD & C Red No. 4), 1,4-bis [(2-sulfo-4-methylphenyl) amino] -9,10-anthraquinone disodium salt (CI 61.570; Acid Green 25), bis [4- (dimethylamino) phenyl] - (3,7-disulfo-2-hydroxynaphth-1-yl) carbenium internal salt, sodium salt (CI 44,090, Food Green No. 4, Acid Green 50), Bis [4- (diethylamino) phenyl] (2,4-disulfophenyl) carbenium inner salt, sodium salt (2: 1) (CI 42.045, Food Blue No. 3, Acid Blue 1), bis [4- (diethylamino) phenyl] (5-hydroxy-2,4-disulfophenyl) -carbenium inner salt, calcium salt (2: 1) (CI 42,051, Acid Blue 3), N- [4 - [(2,4-disulfophenyl) [4- [ethyl (phenylmethyl) amino) phenyl] methylene] -2,5-cyclohexadien-1-ylidene] -N-ethylbenzenemethanamine hydroxide, inner salt, sodium salt (CI 42.080, Acid Blue 7), (2-sulfophenyl) di [4- (2H) ethyl ((4-sulfophenyl) methyl) amino) phenyl] -carbenium disodium salt betaine (CI 42.090, Acid Blue 9, FD & C Blue No. 1), 1-amino-4- (phenylamino) -9,10-anthraquinone-2 sulfonic acid (CI 62.055; Acid Blue 25), 1-amino-4- (cyclohexylamino) - 9,10-anthraquinone-2-sulfonic acid sodium salt (CI 62045; Acid Blue 62), 2- (1,3-dihydro-3-oxo-5-sulfo-2H-indol-2-ylidene) -2,3-dihydro-3-oxo-1H-indole-5-sulfonic acid disodium salt (CI 73.015, Acid Blue 74), 9- (2-carboxyphenyl) -3 - [(2-methylphenyl) amino] -6 - [(2-methyl-4-sulfophenyl) amino] xanthylium inner salt, sodium salt (CI Acid Violet 9), 1-hydroxy-4 - [(4-methyl-2-sulfophenyl) amino] -9,10-anthraquinone sodium salt (CI 60.730, D & C Violet No. 2, Acid Violet 43), Bis [Biol. 3-nitro-4 - [(4-phenylamino) -3-sulfophenylamino] -phenyl] sulfone (CI 10.410; Acid Brown 13), 5-amino-4-hydroxy-6 - [(4-nitrophenyl) -azo ] -3- (phenylazo) -2,7-naphthalenedisulfonic acid disodium salt (CI 20,470, Acid Black 1), 3-hydroxy-4 - [(2-hydroxynaphth-1-yl) azo] -7-nitro-1 -naphthalene-sulfonic acid-chromium complex (3: 2) (CI 15,711, Acid Black 52), 4- (acetylamino) -5-hydroxy-6 - [(7-sulfo-4 - [(4-sulfophenynazo) -naphth-1 yl) azo] -1,7-naphthalenedisulfonic acid tetrasodium salt (CI 28,440, Food Black No. 1), 3 ', 3 ", 5', 5" -tetrabromophenolsulfonephthalein (bromophenol blue).

preferred anionic substantive dyes are among the international ones Designations or trade names Acid Yellow 1, Yellow 10, Acid Yellow 23, Acid Yellow 36, Acid Orange 7, Acid Red 33, Acid Red 52, Pigment Red 57: 1, Acid Blue 7, Acid Green 50, Acid Violet 43, Acid Black 1 and Acid Black 52 known compounds.

Cationic direct dyes:

When cationic substantive dyes are in particular 9- (dimethylamino) benzo [a] phenoxazine-7-ium chloride (C.I. 51,175; Basic Blue 6), di [4- (diethylamino) phenyl] [4- (ethylamino) naphthyl] carbenium chloride (C.I. 42,595; Basic Blue 7), di (4- (dimethylamino) phenyl) - (4- (methylphenylamino) -naphthalen-1-yl) carbenium chloride (C.I. 42,563, Basic Blue 8), 3,7-di (dimethylamino) -phenothiazine-5-ium chloride (C.I. 52.015 Basic Blue 9), di [4- (dimethylamino) phenyl] [4- (phenylamino) naphthyl] carbenium chloride (C.I. 44.045; Basic Blue 26), 2 - [(4- (ethyl (2-hydroxyethyl) amino) phenyl) azo] -6-methoxy-3-methylbenzothiazolium methylsulfate (C.I. 11,154; Basic Blue 41), 8-amino-2-bromo-5-hydroxy-4-imino-6 - [(3- (trimethylammonio) phenyl) amino] -1 (4H) -naphthalenone chloride (C.I. 56,059; Basic Blue No. 99), bis [4- (dimethylamino) phenyl] - [4- (methylamino) phenyl] carbenium chloride (C.I. 42,535, Basic Violet 1), tri (4-amino-3-methylphenyl) carbenium chloride (C.I. 42,520; Basic Violet 2), tri [4- (dimethylamino) -phenyl] carbenium chloride (C.I. 42,555; Basic Violet 3), 2- [3,6- (diethylamino) dibenzopyranium-9-yl] benzoic acid chloride (C.I., 45.170, Basic Violet 10), di (4-aminophenyl) (4-amino-3-methylphenyl) carbenium chloride (C.I. 42,510 Basic Violet 14), 1,3-bis [(2,4-diamino-5-methylphenyl) azo] -3-methylbenzene (C.I. 21,010; Basic Brown 4), 1 - [(4-aminophenyl) azo] -7- (trimethylammonio) -2-naphthol chloride (C.I. 12,250, Basic Brown 16), 1 - [(4-amino-2-nitrophenyl) azo] -7- (trimethylammonio) -2-naphthol chloride, 1 - [(4-amino-3-nitrophenynazo] -7- (trimethylammonio) -2-naphthol-chloride (C.I. 12,251; Basic Brown 17), 3 - [(4-amino-2,5-dimethoxyphenyl) azo] -N, N, N-trimethylbenzeneamine chloride (C.I. 12.605, Basic Orange 69), 3,7-diamino-2,8-dimethyl-5-phenylphenazinium chloride (C.I. 50,240, Basic Red 2), 1,4-dimethyl-5 - [(4- (dimethylamino) phenyl) azo] -1,2,4-triazolium chloride (C.I. 11,055; Basic Red 22), 2-hydroxy-1 - [(2-methoxyphenynazo) -7- (trimethylammonio) -naphthalene chloride (C.I. 12,245; Basic Red 76), di [4- (dimethylamino) phenyl] iminomethane hydrochloride (C.I. 41,000, Basic Yellow 2), 2- [2 - ((2,4-dimethoxyphenyl) amino) ethenyl] -1,3,3-trimethyl-3H-indol-1-ium chloride (C.I., 48,055; Basic Yellow 11), 3-methyl-1-phenyl-4 - [(3- (trimethylammonio) phenyl) azo] pyrazol-5-one chloride (C.I. 12.719; Basic Yellow 57), bis [4- (diethylamino) phenyl] phenylcarbenium hydrogensulfate (1: 1) (C.I., 42.040, Basic Green 1), di (4- (dimethylamino) phenyl) -phenylmethanol (C.I. 42,000, Basic Green 4), 1- (2-morpholiniumpropylamino) -4-hydroxy-9,10-anthraquinone methylsulfate, 1 - [(3- (dimethylpropylaminium) -propyl) amino] -4- (methylamino) -9,10-anthraquinone chloride and direct dyes containing a heterocycle, the has at least one quaternary nitrogen atom.

• (a) kationische Triphenylmethanfarbstoffe, wie beispielsweise Basic Blue 7, Basic Blue 26, Basic Violet 2 und Basic Violet 14,
• (b) aromatischen Systeme, die mit einer quaternären Stickstoffgruppe substituiert sind, wie beispielsweise Basic Yellow 57, Basic Red 76, Basic Blue 99, Basic Brown 16 und Basic Brown 17, sowie
• (c) direktziehende Farbstoffe, die einen Heterocyclus enthalten, der mindestens ein quaternäres Stickstoffatom aufweist, wie sie beispielsweise in der EP-A2-998 908 , auf die an dieser Stelle explizit Bezug genommen wird, in den Ansprüchen 6 bis 11 genannt werden.

Preferred cationic substantive dyes are included

• (a) cationic triphenylmethane dyes such as Basic Blue 7, Basic Blue 26, Basic Violet 2 and Basic Violet 14,
• (b) aromatic systems substituted with a quaternary nitrogen group, such as Basic Yellow 57, Basic Red 76, Basic Blue 99, Basic Brown 16 and Basic Brown 17, as well as
• (C) direct dyes containing a heterocycle having at least one quaternary nitrogen atom, as described for example in the EP-A2-998 908 to which reference is made at this point, are called in the claims 6 to 11.

Preferred cationic substantive dyes of group (c) are in particular the following compounds:

The Compounds of the formulas (DZ1), (DZ3) and (DZ5), which are also available under the terms Basic Yellow 87, Basic Orange 31 and Basic Red 51 are very particularly preferred cationic substantive Dyes of group (c).

The cationic direct dyes, which are sold under the trademark Arianor ^®, according to the invention are also very particularly preferred cationic direct dyes.

Nonionic substantive dyes:

When Nonionic substantive dyes are particularly suitable nonionic nitro and quinone dyes and neutral azo dyes.

Suitable blue nitro dyes are in particular:
1,4-bis [(2-hydroxyethyl) amino] -2-nitrobenzene, 1- (2-hydroxyethyl) amino-2-nitro-4- [di (2-hydroxyethyl) amino] benzene (HC Blue 2), 1-Methylamino-4- [methyl- (2,3-dihydroxypropyl) amino] -2-nitrobenzene (HC Blue 6), 1 - [(2,3-dihydroxypropyl) amino] -4- [ethyl- (2- hydroxyethyl) amino] -2-nitrobenzene hydrochloride (HC Blue 9), 1 - [(2,3-dihydroxypropyl) amino] -4- [methyl (2-hydroxyethyl) amino] -2-nitrobenzene (HC Blue 10) , 4- [di (2-hydroxyethyl) amino] -1 - [(2-methoxyethyl) amino] -2-nitrobenzene (HC Blue 11), 4- [ethyl- (2-hydroxyethyl) amino] -1- [ (2-hydroxyethyl) amino] -2-nitrobenzene hydrochloride (HC Blue 12), 2 - ((4-amino-2-nitrophenyl) amino) -5-dimethylaminobenzoic acid (HC Blue 13), 1-amino-3-methyl 4 - [(2-hydroxyethylamino) -6-nitrobenzene (HC Violet 1), 1- (3-hydroxypropylamino) -4- [di (2-hydroxyethyl) amino] -2-nitrobenzene (HC Violet 2), 1- (2-Aminoethylamino) -4- [di (2-hydroxyethyl) amino] -2-nitrobenzene, 4- (di (2-hydroxyethyl) amino) -2-nitro-1-phenylaminobenzene.

Suitable red nitro dyes are in particular:
1-Amino-4 - [(2-hydroxyethyl) amino] -2-nitrobenzene (HC Red 7), 2-amino-4,6-dinitrophenol (picramic acid) and its salts, 1,4-diamino-2-nitrobenzene ( CI 76,070), 4-amino-2-nitro-diphenylamine (HC Red 1), 1-amino-4- [di (2-hydroxyethyl) amino] -2-nitrobenzene hydrochloride (HC Red 13), 1-amino- 4 - [(2-hydroxyethyl) amino] -5-chloro-2-nitrobenzene, 4-amino-1 - [(2-hydroxyethyl) amino] -2-nitrobenzene (HC Red 3), 4 - [(2-hydroxyethyl ) methylamino] -1- (methylamino) -2-nitrobenzene, 1-amino-4 - [(2,3-dihydroxypropyl) amino] -5-methyl-2-nitrobenzene, 1-amino-4- (methylamino) -2 -nitrobenzene, 4-amino-2-nitro-1 - [(prop-2-en-1-yl) amino] benzene, 4-amino-3-nitrophenol, 4 - [(2-hydroxyethyl) amino] - 3-nitrophenol, 4 - [(2-nitrophenyl) amino] phenol (HC Orange 1), 1 - [(2-aminoethyl) amino] -4- (2-hydroxyethoxy) -2-nitrobenzene (HC Orange 2), 4 - (2,3-dihydroxypropoxy) -1 - [(2-hydroxyethyl) amino] -2-nitrobenzene (HC Orange 3), 1-amino-5-chloro-4 - [(2,3-dihydroxypropyl) amino] - 2-nitrobenzene (HC Red 10), 5-chloro-1,4- [di (2,3-dihydroxypropyl) amino] -2-nitrobenzene ol (HC Red 11), 2 - [(2-hydroxyethyl) amino] -4,6-dinitrophenol, 4-ethylamino-3-nitrobenzoic acid, 2 - [(4-amino-2-nitrophenyl) amino] benzoic acid, 2 Chloro-6-ethylamino-4-nitrophenol, 2-amino-6-chloro-4-nitrophenol, 4 - [(3-hydroxypropyl) amino] -3-nitrophenol (HC Red BN), 2,5-diamino-6 -nitropyridine, 6-amino-3 - [(2-hydroxyethyl) amino] -2-nitropyridine, 3-amino-6 - [(2-hydroxyethyl) amino] -2-nitropyridine, 3-amino-6- (ethylamino) 2-nitropyridine, 3 - [(2-hydroxyethyl) amino] -6- (methylamino) -2-nitropyridine, 3-amino-6- (methylamino) -2-nitropyridine, 6- (ethylamino) -3 - [( 2-hydroxyethylamino] -2-nitropyridine, 1,2,3,4-tetrahydro-6-nitroquinoxaline, 7-amino-3,4-dihydro-6-nitro-2H-1,4-benzoxazine (HC Red 14).

Suitable yellow nitro dyes are in particular:
1,2-diamino-4-nitrobenzene (CI 76,020), 1 - [(2-hydroxyethyl) amino] -2-nitrobenzene (HC Yellow 2), 1- (2-hydroxyethoxy) -2 - [(2-hydroxyethynamino] 5-nitrobenzene (HC Yellow 4), 1-amino-2 - [(2-hydroxyethyl) amino] -5-nitrobenzene (HC Yellow 5), 4 - [(2,3-dihydroxypropyl) amino] -3- nitro-1-trifluoromethylbenzene (HC Yellow 6), 2- [di (2-hydroxyethyl) amino] -5-nitrophenol, 2 - [(2-hydroxyethyl) amino] -1-methoxy-5-nitrobenzene, 2-amino- 3-nitrophenol, 2-amino-4-nitrophenol, 1-amino-2-methyl-6-nitrobenzene, 1- (2-hydroxyethoxy) -3-methylamino-4-nitrobenzene, 2,3- (dihydroxypropoxy) -3- methylamino-4-nitrobenzene, 3 - [(2-aminoethyl) amino] -1-methoxy-4-nitrobenzene hydrochloride (HC Yellow 9), 1-chloro-2,4-bis [(2-hydroxyethyl) amino] - 5-nitrobenzene (HC Yellow 10), 2 - [(2-hydroxyethynamino] -5-nitrophenol (HC Yellow 11), 1 - [(2'-ureidoethyl) amino] -4-nitrobenzene, 1-amino-4- [ (2-aminoethyl) amino] -5-methyl-2-nitrobenzene, 4 - [(2-hydroxyethyl) amino] -3-nitro-1-methylbenzene, 1-chloro-4 - [(2-hydroxyethyl) amino] - 3-nitrobenzene (HC Yellow 12), 4 - [(2-H ydroxyethyl) amino] -3-nitro-1-trifluoromethylbenzene (HC Yellow 13), 4 - [(2-hydroxyethyl) amino] -3-nitrobenzonitrile (HC Yellow 14), 4 - [(2-hydroxyethynamino] 3-nitrobenzamide (HC Yellow 15) 3 - [(2-hydroxyethyl) amino] -4-methyl-1-nitrobenzene, 4-chloro-3 - [(2-hydroxyethyl) amino] -1-nitrobenzene.

Suitable quinone dyes are in particular:
1,4-di [(2,3-dihydroxypropyl) amino] -9,10-anthraquinone, 1,4-di [(2-hydroxyethyl) amino] -9,10-anthraquinone (CI 61.545, Disperse Blue 23), 1 - [(2-hydroxyethyl) amino] -4-methylamino-9,10-anthraquinone (CI 61,505, Disperse Blue 3), 2 - [(2-aminoethyl) amino] -9,10-anthraquinone (HC Orange 5) , 1-amino-4-hydroxy-9,10-anthraquinone (CI 60.710, Disperse Red 15), 1-hydroxy-4 - [(4-methyl-2-sulfophenyl) amino] -9,10-anthraquinone, 7- Beta-D-glucopyranosyl-9,10-dihydro-1-methyl-9,10-dioxo-3,5,6,8-tetrahydroxy-2-anthracenecarboxylic acid (CI 75,470, Natural Red 4), 1 - [(3 Aminopropyl) amino] -4-methylamino-9,10-anthraquinone (HC Blue 8), 1 - [(3-aminopropyl) amino] -9,10-anthraquinone (HC Red 8), 1,4-diamino-2 -methoxy-9,10-anthraquinone (CI 62.015, Disperse Red 11, Solvent Violet No. 26), 1,4-dihydroxy-5,8-bis [(2-hydroxyethyl) amino] -9,10-anthraquinone (CI 62,500, Disperse Blue 7, Solvent Blue No. 69), 1,4-diamino-9,10-anthraquinone (CI 61.100, Disperse Violet 1), 1-amino-4- (methylamino) -9,10-anthraquinone (CI 61,105, Disperse Viole t 4, Solvent Violet No. 12), 2-hydroxy-3-methoxy-1,4-naphthoquinone, 2,5-dihydroxy-1,4-naphthoquinone, 2-hydroxy-3-methyl-1,4-naphthoquinone, N- {6 - [( 3-chloro-4- (methylamino) phenyl) imino] -4-methyl-3-oxo-1,4-cyclohexadien-1-yl} urea (HC Red 9), 2 - {{4- [di (2- hydroxyethyl) amino] phenyl} amino} -5 - [(2-hydroxyethyl) amino] -2,5-cyclohexadiene-1,4-dione (HC Green 1), 5-hydroxy-1,4-naphthoquinone (CI 75,500, Natural Brown 7), 2-hydroxy-1,4-naphthoquinone (CI 75,480, Natural Orange 6), 1,2-dihydro-2- (1,3-dihydro-3-oxo-2H-indol-2-ylidene) -3H-indol-3-one (CI 73,000), 4- { {5 - [(2-hydroxyethyl) amino] -1-methyl-1H-pyrazol-4-yl} imino} -4,5-dihydro-5 - [(2-hydroxyethyl) imino] -1-methyl-1H Pyrazole sulfate (1: 1), hydrate (1: 1).

Suitable neutral azo dyes are in particular:
1- [di (2-hydroxyethyl) amino] -3-methyl-4 - [(4-nitrophenyl) azo] benzene (CI 11.210, Disperse Red 17), 1- [di (2-hydroxyethyl) amino] -4 - [(4-nitrophenyl) azo] benzene (Disperse Black 9), 4 - [(4-aminophenyl) azo] -1- [di (2-hydroxyethyl) amino] -3-methylbenzene (HC Yellow 7), 2 , 6-diamino-3 - [(pyridin-3-yl) azo] pyridine, 2 - {[4- (acetylamino) phenyl] azo} -4-methylphenol (CI 11855, Disperse Yellow 3), 4 - [( 4-nitrophenyl) azo] -aniline (CI 11.005, Disperse Orange 3).

preferred Nonionic direct dyes are among the international ones Designations or trade names HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, HC Yellow 12, HC Orange 1, Disperse Orange 3, HC Red 1, HC Red 3, HC Red 10, HC Red 11, HC Red 13, HC Red BN, HC Blue 2, HC Blue 11, HC Blue 12, Disperse Blue 3, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Disperse Black 9 known compounds, and 1,4-diamino-2-nitrobenzene, 2-amino-4-nitrophenol, 1,4-bis (2-hydroxyethyl) amino-2-nitrobenzene, 3-nitro-4- (2-hydroxyethyl) aminophenol, 2- (2-hydroxyethyl) amino-4,6-dinitrophenol, 4 - [(2-hydroxyethyl) amino] -3-nitro-1-methylbenzene, 1-amino-4- (2-hydroxyethyl) amino-5-chloro-2-nitrobenzene, 4-amino-3-nitrophenol, 1- (2'-ureidoethyl) amino-4-nitrobenzene, 2 - [(4-amino-2-nitrophenylamino] benzoic acid, 6-nitro-1,2,3,4-tetrahydroquinoxaline, 2-hydroxy-1,4-naphthoquinone, Picramic acid and its salts, 2-amino-6-chloro-4-nitrophenol, 4-ethylamino-3-nitrobenzoic acid and 2-chloro-6-ethylamino-4-nitrophenol.

It It is not necessary that the substantive dyes each represent uniform connections. Rather, conditioned by the manufacturing processes for the individual Dyes, in minor amounts still contain other components be, as far as they do not adversely affect the dyeing result or for other reasons, e.g. B. toxicological, excluded Need to become.

Farther can also be used as direct dyes in nature occurring dyes are used, as for example in henna red, henna neutral, henna black, chamomile flower, Sandalwood, black tea, buckthorn bark, sage, bluewood, madder root, Catechu, Sedre and Alkana root are included.

Farther can the agent (A) according to the invention also in the Naturally occurring dyes, such as red, for example, in henna, Henna neutral, Henna black, Chamomile flower, Sandalwood, black tea, buckthorn bark, sage, bluewood, madder root, catechu, Sedre and alkano root are included.

The actual oxidative coloring of the hair can basically done with atmospheric oxygen. However, preference is given to a chemical Oxidizing agent used, especially if in addition to the staining a whitening effect on human hair is desired. in the Frame of a preferred embodiment of this article Therefore, according to the present invention, the agent (A) becomes immediate prior to application of an agent (A1) containing an oxidation dye precursor, and an agent (A2) containing an oxidizing agent.

When Oxidizing agents include persulfates, chlorites and especially hydrogen peroxide or its addition products of urea, melamine and sodium borate in question. However, according to the invention, the oxidation colorant also be applied to the hair together with a catalyst, the oxidation of the dye precursors, eg. B. by atmospheric oxygen, activated. Such catalysts are z. As metal ions, iodides, Quinones or certain enzymes.

Suitable metal ions are, for example, Zn ²⁺ Cu ^2+, Fe ²⁺ Fe ^3+, Mn ^2+, Mn ^4+, Li ^+, Mg ²⁺ Ca ³⁺ and Al ³⁺ is particularly suitable are Zn ^2+, Cu ²⁺ and Mn ^{2 +} . The metal ions can in principle be used in the form of any physiologically acceptable salt or in the form of a complex compound. Preferred salts are the acetates, sulfates, halides, lactates and tartrates. By using these metal salts, both the formation of the dyeing can be accelerated and the color shade can be specifically influenced.

• – Pyranose-Oxidase und z. B. D-Glucose oder Galactose,
• – Glucose-Oxidase und D-Glucose,
• – Glycerin-Oxidase und Glycerin,
• – Pyruvat-Oxidase und Benztraubensäure oder deren Salze,
• – Alkohol-Oxidase und Alkohol (MeOH, EtOH),
• – Lactat-Oxidase und Milchsäure und deren Salze,
• – Tyrosinase-Oxidase und Tyrosin,
• – Uricase und Harnsäure oder deren Salze,
• – Cholinoxidase und Cholin,
• – Aminosäure-Oxidase und Aminosäuren.

Suitable enzymes are z. As peroxidases, which can significantly increase the effect of small amounts of hydrogen peroxide. Furthermore, such enzymes are suitable according to the invention which directly oxidize the oxidation dye precursors with the aid of atmospheric oxygen, such as, for example, the laccases, or generate small amounts of hydrogen peroxide in situ and thus biocatalytically activate the oxidation of the dye precursors. Particularly suitable catalysts for the oxidation of the dye precursors are the so-called 2-electron oxidoreductases in combination with the specific substrates, eg. B.

• - pyranose oxidase and z. D-glucose or galactose,
• Glucose oxidase and D-glucose,
• - glycerol oxidase and glycerin,
• Pyruvate oxidase and pyruvic acid or its salts,
• Alcohol oxidase and alcohol (MeOH, EtOH),
• Lactate oxidase and lactic acid and their salts,
• Tyrosinase oxidase and tyrosine,
• Uricase and uric acid or their salts,
• - choline oxidase and choline,
• - amino acid oxidase and amino acids.

The actual oxidative hair dye is conveniently immediately before use by mixing the preparation of the Oxidizing agent (A2) with the preparation (A1) containing the Dye precursors, prepared. The resulting ready-to-use Hair dye preparation (A) should preferably have a pH ranging from 6 to 12. Particularly preferred is the application the hair dye in a weak alkaline environment. The application temperatures can be in a range between 15 and 40 ° C lie. After an exposure time of 5 to 45 minutes, the hair dye is removed by rinsing removed from the hair to be dyed. The washing up with a Shampoo is omitted if a carrier with high surfactant content, z. As a dyeing shampoo was used.

Especially For hair that is difficult to dye, the preparation may be mixed with the Dye precursors but also without prior mixing with the Oxidation component to be applied to the hair. After a Einwirkdauer of 20 to 30 minutes will then - if necessary after an intermediate rinse - the oxidation component applied. After another exposure time of 10 to 20 minutes is then rinsed and nachshampooniert if desired. In this embodiment, according to a first variant, in which the previous application of the dye precursors to effect a better penetration into the hair, the corresponding Medium adjusted to a pH of about 4 to 7. According to one second variant, first an air oxidation is sought, wherein the applied agent preferably has a pH of 7 to 10 has. In the subsequent accelerated post-oxidation may be the use of acidified peroxydisulfate solutions be preferred as the oxidizing agent.

in the second and optionally in further steps of the invention Procedure, the hair is treated with an agent (B), the immediately before the application of an agent (B1) and an agent (B2) is obtained by mixing.

The Agent (B1) contains at least one reactive carbonyl compound.

• a) von Aminen und deren Derivate unter Bildung von Iminen oder Oximen als Additionsverbindung
• b) von Alkoholen unter Bildung von Acetalen oder Ketalen als Additionsverbindung
• c) von Wasser unter Bildung von Hydraten als Additionsverbindung (Komponente (Oxo1) leitet sich in diesem Fall c) von einem Aldehyd ab)

an das Kohlenstoffatom der Carbonylgruppe der reaktiven Carbonylverbindung.Reactive carbonyl compounds have in the context of the invention at least one carbonyl group as a reactive group which reacts with the CH-acidic component to form a covalent bond. Preferred reactive carbonyl compounds are selected from compounds which carry at least one formyl group and / or at least one keto group, in particular at least one formyl group. Furthermore, those compounds according to the invention are also suitable as component (Oxo1) in which the reactive carbonyl group is derivatized or masked such that the reactivity of the carbon atom of the derivatized carbonyl group with respect to the component (Oxo2) is always present. These derivatives are preferably addition compounds

• a) amines and derivatives thereof to form imines or oximes as addition compound
• b) of alcohols to form acetals or ketals as addition compound
• c) of water with formation of hydrates as addition compound (component (oxo1) is derived in this case c) from an aldehyde)

to the carbon atom of the carbonyl group of the reactive carbonyl compound.

Among the reactive carbonyl compounds of the agent (B1), preferred are compounds selected from compounds of the following group: benzaldehyde and its derivatives, naphthaldehyde and its derivatives, cinnamaldehyde and its derivatives, 2-formylmethylene-1,3,3-trimethylindoline (Fischer's aldehyde or tribas Aldehyde), 2-indolealdehyde, 3-indolealdehyde, 1-methylindole-3-aldehyde, 2-methylindole-3-aldehyde, 2- (1 ', 3', 3'-trimethyl-2-indolinylidene) -acetaldehyde, 1- Methylpyrrole-2-aldehyde, pyridoxal, 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde, furfural, 5-nitrofurfural, chromone-3-aldehyde, 3 (5'-nitro-2'-furyl) acrolein, 3- (2'-furyl) acrolein and imidazole-2-aldehyde, 5- (4-dimethylaminophenyl) penta-2,4-dienal, 5- (4-diethylaminophenyl) penta-2,4-dienal, 5- (4-methoxyphenyl) penta-2,4-dienal, 5- (3,4-dimethoxyphenyl) penta-2,4-dienal, 5- (4-methoxyphenyl) -penta-2,4-dienal 2,4-dimethoxyphenyl) penta-2,4-dienal, 5- (4-piperidinophenyl) penta-2,4-dienal, 5- (4-morpholinophenyl) penta-2,4-dienal, 5- (4-pyrrolidinophenyl ) penta-2,4-dienal, 5- (4-dimethylamino-1-naphthyl) penta-3,5-dienal, piperonal, 6-nitropiperonal, 2-nitropiperonal, 5-nitrovanillin, 2,5-dinitrosalicylaldehyde, 5- Bromo-3-nitrosalicylaldehyde, 3-nitro-4-formylbenzenesulfonic acid, 4-formyl-1-methylpyridinium, 2-formyl-1-methylpyridinium, 4-formyl-1-ethylpyridinium, 2-formyl-1-ethylpyridinium, 4-Formyl-1-benzylpyridinium, 2-formyl-1-benzylpyridinium, 4-formyl-1,2-dimethylpyridinium, 4-formyl-1,3-dimethylpyridinium, 4-formyl-1-methylquinolinium, 2 -Formyl-1-methylquinolinium, 5-formyl-1-methylquinolinium, 6-formyl-1-methylquinolinium, 7-formyl-1-methylquinolinium, 8-formyl-1-methylquinolinium, 5-formyl-1-ethylquinolinium , 6-Formyl-1-ethylquinolinium, 7-formyl-1-ethylquinol inium, 8-formyl-1-ethylquinolinium, 5-formyl-1-benzylquinolinium, 6-formyl-1-benzylquinolinium, 7-formyl-1-benzylquinolinium, 8-formyl-1-benzylquinolinium, 5-formyl- 1-allyl-quinolinium, 6-formyl-1-allyl-quinolinium, 7-formyl-1-allyl-quinolinium and 8-formyl-1-allyl-quinolinium-benzenesulfonate, p-toluenesulfonate, methanesulfonate, perchlorate, sulfate, chloride, bromide, iodide, tetrachlorozincate, methylsulfate, trifluoromethanesulfonate, tetrafluoroborate, isatin, 1-methyl-isatin, 1-allyl-isatin, 1-hydroxymethyl-isatin, 5-chloro-isatin, 5-methoxy-isatin , 5-nitroisatin, 6-nitro-isatin, 5-sulfoisoisine, 5-carboxy-isatin, quinisatin, 1-methylquinisatin, and any mixtures of the above compounds.

Especially it is preferred if as the reactive carbonyl compound of the agent (B1) a compound selected from at least one compound the group consisting of 4-hydroxy-3-methoxybenzaldehyde, 3,5-dimethoxy-4-hydroxybenzaldehyde, 4-hydroxy-1-naphthaldehyde, 4-hydroxy-2-methoxybenzaldehyde, 3,4-dihydroxy-5-methoxybenzaldehyde, 3,4,5-trihydroxybenzaldehyde, 3,5-dibromo-4-hydroxybenzaldehyde, 4-hydroxy-3-nitrobenzaldehyde, 3-bromo-4-hydroxybenzaldehyde, 4-hydroxy-3-methylbenzaldehyde, 3,5-dimethyl-4-hydroxybenzaldehyde, 5-bromo-4-hydroxy-3-methoxybenzaldehyde, 4-diethylamino-2-hydroxybenzaldehyde, 4-dimethylamino-2-methoxybenzaldehyde, 2-methoxybenzaldehyde, 3-methoxybenzaldehyde, 4-methoxybenzaldehyde, 2-ethoxybenzaldehyde, 3-ethoxybenzaldehyde, 4-ethoxy-benzaldehyde, 4-hydroxy-2,3-dimethoxybenzaldehyde, 4-hydroxy-2,5-dimethoxybenzaldehyde, 4-hydroxy-2,6-dimethoxybenzaldehyde, 4-hydroxy-2-methylbenzaldehyde, 4-hydroxy-2,3-dimethylbenzaldehyde, 4-hydroxy-2,5-dimethylbenzaldehyde, 4-hydroxy-2,6-dimethylbenzaldehyde, 3,5-diethoxy-4-hydroxybenzaldehyde, 2,6-diethoxy-4-hydroxybenzaldehyde, 3-hydroxy-4-methoxybenzaldehyde, 2-hydroxy-4-methoxybenzaldehyde, 2-ethoxy-4-hydroxybenzaldehyde, 3-ethoxy-4-hydroxybenzaldehyde, 4-ethoxy-2-hydroxybenzaldehyde, 4-ethoxy-3-hydroxybenzaldehyde, 2,3-dimethoxybenzaldehyde, 2,4-dimethoxybenzaldehyde, 2,5-dimethoxybenzaldehyde, 2,6-dimethoxybenzaldehyde, 3,4-dimethoxybenzaldehyde, 3,5-dimethoxybenzaldehyde, 2,3,4-trimethoxybenzaldehyde, 2,3,5-trimethoxybenzaldehyde, 2,3,6-trimethoxybenzaldehyde, 2,4,6-trimethoxybenzaldehyde, 2,4,5-trimethoxybenzaldehyde, 2,5,6-trimethoxybenzaldehyde, 2-hydroxybenzaldehyde, 3-hydroxybenzaldehyde, 4-hydroxybenzaldehyde, 2,3-dihydroxybenzaldehyde, 2,4-dihydroxybenzaldehyde, 2,4-dihydroxy-3-methylbenzaldehyde, 2,4-dihydroxy-5-methylbenzaldehyde, 2,4-dihydroxy-6-methyl-benzaldehyde, 2,4-dihydroxy-3-methoxybenzaldehyde, 2,4-dihydroxy-5-methoxy-benzaldehyde, 2,4-dihydroxy-6-methoxybenzaldehyde, 2,5-dihydroxybenzaldehyde, 2,6-dihydroxybenzaldehyde, 3,4-dihydroxybenzaldehyde, 3,4-dihydroxy-2-methylbenzaldehyde, 3,4-dihydroxy-5-methylbenzaldehyde, 3,4-dihydroxy-6-methylbenzaldehyde, 3,4-dihydroxy-2-methoxybenzaldehyde, 3,5-dihydroxybenzaldehyde, 2,3,4-trihydroxybenzaldehyde, 2,3,5-trihydroxybenzaldehyde, 2,3,6-trihydroxybenzaldehyde, 2,4,6-trihydroxybenzaldehyde, 2,4,5-trihydroxybenzaldehyde, 2,5,6-trihydroxybenzaldehyde, 4-dimethylaminobenzaldehyde, 4-diethylaminobenzaldehyde, 4-dimethylamino-2-hydroxybenzaldehyde, 4-pyrrolidinobenzaldehyde, 4-morpholinobenzaldehyde, 2-morpholinobenzaldehyde, 4-piperidinobenzaldehyde, 3,5-dichloro-4-hydroxybenzaldehyde, 4-hydroxy-3,5-diiodobenzaldehyde, 3-chloro-4-hydroxybenzaldehyde, 5-chloro-3,4-dihydroxybenzaldehyde, 5-bromo-3,4-dihydroxybenzaldehyde, 3-chloro-4-hydroxy-5-methoxybenzaldehyde, 2-chloro-3,4-dihydroxybenzaldehyde, 2-bromo-3,4-dihydroxybenzaldehyde, 4-hydroxy-3-iodo-5-methoxybenzaldehyde, 2-methoxy-1-naphthaldehyde, 4-methoxy-1-naphthaldehyde, 2-hydroxy-1-naphthaldehyde, 2,4-dihydroxy-1-naphthaldehyde, 4-hydroxy-3-methoxy-1-naphthaldehyde, 2-hydroxy-4-methoxy-1-naphthaldehyde, 3-hydroxy-4-methoxy-1-naphthaldehyde, 2,4-dimethoxy-1-naphthaldehyde, 3,4-dimethoxy-1-naphthaldehyde, 4-dimethylamino-1-naphthaldehyde, 3-hydroxy-4-nitrobenzaldehyde, 2-hydroxy-3-methoxy-5-nitrobenzaldehyde, 5-nitrovanillin, 2,5-dinitrosalicylaldehyde, 5-bromo-3-nitrosalicylaldehyde, 2-dimethylaminobenzaldehyde, 2-chloro-4-dimethylaminobenzaldehyde, 4-dimethylamino-2-methylbenzaldehyde, 4-diethylamino-cinnamaldehyde, 4-dibutylaminobenzaldehyde, 3-carboxy-4-hydroxybenzaldehyde, 5-carboxyvanillin, 3-carboxy-4-hydroxy-5-methylbenzaldehyde, 3-carboxy-5-ethoxy-4-hydroxybenzaldehyde, 3-carboxy-4-hydroxybenzaldehyde, 5-carboxyvanillin, 3-carboxy-4-hydroxy-5-methylbenzaldehyde, 3-carboxy-5-ethoxy-4-hydroxybenzaldehyde, 3-allyl-4-hydroxybenzaldehyde, 3-allyl-4-hydroxy-5-methoxybenzaldehyde, 3-allyl-4-hydroxy-5-methylbenzaldehyde, 3-allyl-5-bromo-4-hydroxybenzaldehyde, 3,5-diallyl-4-hydroxybenzaldehyde, 3-allyl-5-carboxy-4-hydroxybenzaldehyde (3-allyl-5-formyl-2-hydroxybenzoic acid) and 3-allyl-4-hydroxy-5-formylbenzaldehyde or (5-allyl-4-hydroxyisophthalaldehyde) is used.

In a preferred embodiment of the invention Method, the agent (B1) contains a reactive carbonyl compound, which is selected from 4-hydroxy-2-methoxybenzaldehyde, 2-chloro-3,4-dihydroxybenzaldehyde, 2-bromo-3,4-dihydroxybenzaldehyde, 3,4-Dihydroxy-5-methoxybenzaldehyde, 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde and 2,4-dimethoxybenzaldehyde. Particularly preferred Agent (B1) proved to be the 4-hydroxy-2-methoxybenzaldehyde in combination with at least one further reactive carbonyl compound selected from 2-chloro-3,4-dihydroxybenzaldehyde, 2-bromo-3,4-dihydroxybenzaldehyde, 3,4-Dihydroxy-5-methoxybenzaldehyde, 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde and 2,4-dimethoxy-benzaldehyde.

The reactive carbonyl compound (s) of the agent (B1) are preferably in an amount of 0.03 to 65.00 mmol, based on 100 g of the agent (B1). The use of 1.00 to 30.00 mmol, based on 100 g of the agent (B1) is particularly preferred.

The Agent (B2) contains at least one CH-acidic compound of general formula (CH-1) and / or general formula (CH-2) (vide supra).

As CH-acidic compounds are generally considered those compounds which carry a bound to an aliphatic carbon atom hydrogen atom, wherein due to electron-withdrawing substituents, activation of the corresponding carbon-hydrogen bond are effected. The compounds of formula (CH-1) and (CH-2) are C, H-acidic compounds. From the cationic compounds of the formula (CH-1), it is possible by targeted addition of a base which effects the cleavage of a proton to represent the corresponding uncharged enamine form. As an example for compounds of the formula (CH-1), the illustration of the enamine form is illustrated below by means of the formulas (CH-1-A) and (CH-1-B) with R ⁷ = CH ₃ . The corresponding enamine forms of the CH-acidic compounds according to formula (CH-1) are also according to the invention.

worin

• • R⁸ und R⁹ stehen unabhängig voneinander für eine lineare oder cyclische (C₁ bis C₆)-Alkylgruppe, eine (C₂ bis C₆)-Alkenylgruppe, eine gegebenenfalls substituierte Arylgruppe, eine gegebenenfalls substituierte Heteroarylgruppe, eine Aryl-(C₁ bis C₆)-alkylgruppe, eine (C₁ bis C₆)-Hydroxyalkylgruppe, eine (C₂ bis C₆)-Polyhydroxyalkylgruppe, eine (C₁ bis C₆)-Alkoxy-(C₁ bis C₆)-alkylgruppe, eine Gruppe R^IR^IIN-(CH₂)_m-, worin R^I und R^II stehen unabhängig voneinander für ein Wasserstoffatom, eine (C₁ bis C₄)-Alkylgruppe, eine (C₁ bis C₄)-Hydroxyalkylgruppe oder eine Aryl-(C₁ bis C₄)-alkylgruppe, wobei R^I und R^II gemeinsam mit dem Stickstoffatom einen 5-, 6- oder 7-gliedrigen Ring bilden können und m steht für eine Zahl 2, 3, 4, 5 oder 6,
• • R¹⁰ und R¹² stehen unabhängig voneinander für ein Wasserstoffatom oder eine C₁-C₆-Alkylgruppe, wobei mindestens einer der Reste R¹⁰ und R¹² eine (C₁ bis C₆)-Alkylgruppe bedeutet,
• • R¹¹ steht für ein Wasserstoffatom, eine (C₁ bis C₆)-Alkylgruppe, eine (C₁ bis C₆)-Hydroxyalkylgruppe, eine (C₂ bis C₆)-Polyhydroxyalkylgruppe, eine (C₁ bis C₆)-Alkoxygruppe, eine (C₁ bis C₆)-Hydroxyalkoxygruppe, eine Gruppe R^IIIR^IVN-(CH₂)_q-, worin R^III und R^IV stehen unabhängig voneinander für ein Wasserstoffatom, eine (C₁ bis C₆)-Alkylgruppe, eine (C₁ bis C₆)-Hydroxyalkylgruppe oder eine Aryl-(C₁ bis C₆)-alkylgruppe und q steht für eine Zahl 1, 2, 3, 4, 5 oder 6, wobei der Rest R¹¹ zusammen mit einem der Reste R¹⁰ oder R¹² einen 5- oder 6-gliedrigen aromatischen Ring bilden kann, der gegebenenfalls mit einem Halogenatom, einer (C₁ bis C₆)-Alkylgruppe, einer (C₁ bis C₆)-Hydroxyalkylgruppe, einer (C₂ bis C₆)-Polyhydroxyalkylgruppe, einer (C₁ bis C₆)-Alkoxygruppe, einer (C₁ bis C₆)-Hydroxyalkoxygruppe, einer Nitrogruppe, einer Hydroxygruppe, einer Gruppe R^VR^VIN-(CH₂)_s-, worin R^V und R^VI stehen unabhängig voneinander für ein Wasserstoffatom, eine (C₁ bis C₆)-Alkylgruppe, eine (C₁ bis C₆)-Hydroxyalkylgruppe oder eine Aryl-(C₁ bis C₆)-alkylgruppe und s steht für eine Zahl 0, 1, 2, 3, 4, 5 oder 6 substituiert sein kann,
• • Y steht für ein Sauerstoffatom, ein Schwefelatom oder eine Gruppe NR^VII worin R^VII steht für ein Wasserstoffatom, eine Arylgruppe, eine Heteroarylgruppe, eine (C₁ bis C₆)-Alkylgruppe oder eine Aryl-(C₁ bis C₆)-alkylgruppe,
• • X- steht für ein physiologisch verträgliches Anion.

It is particularly preferred according to the invention to select the compounds of the formula (CH-1) from at least one compound of the formula (CH-3),

wherein

• R ⁸ and R ⁹ are each independently a linear or cyclic (C ₁ to C ₆ ) alkyl group, a (C ₂ to C ₆ ) alkenyl group, an optionally substituted aryl group, an optionally substituted heteroaryl group, an aryl (C ₁ to C ₆ ) alkyl group, a (C ₁ to C ₆ ) hydroxyalkyl group, a (C ₂ to C ₆ ) polyhydroxyalkyl group, a (C ₁ to C ₆ ) alkoxy (C ₁ to C ₆ ) alkyl group , a group R ^I R ^II N- (CH ₂ ) _m -, wherein R ^I and R ^II independently represent a hydrogen atom, a (C ₁ to C ₄ ) alkyl group, a (C ₁ to C ₄ ) hydroxyalkyl group or an aryl (C ₁ to C ₄ ) alkyl group, wherein R ^I and R ^II together with the nitrogen atom can form a 5-, 6- or 7-membered ring and m is a number 2, 3, 4, 5 or 6,
• R ¹⁰ and R ¹² independently of one another represent a hydrogen atom or a C ₁ -C ₆ -alkyl group, where at least one of the radicals R ¹⁰ and R ¹² denotes a (C ₁ to C ₆ ) -alkyl group,
• R ¹¹ represents a hydrogen atom, a (C ₁ to C ₆ ) -alkyl group, a (C ₁ to C ₆ ) -hydroxyalkyl group, a (C ₂ to C ₆ ) -polyhydroxyalkyl group, a (C ₁ to C ₆ ) - Alkoxy group, a (C ₁ to C ₆ ) -hydroxyalkoxy group, a group R ^III R ^IV N- (CH ₂ ) _q -, in which R ^III and R ^IV independently of one another represent a hydrogen atom, a (C ₁ to C ₆ ) alkyl group, a (C ₁ to C ₆ ) hydroxyalkyl group or an aryl (C ₁ to C ₆ ) alkyl group and q is a number 1, 2, 3, 4, 5 or 6, wherein the radical R ¹¹ together with one of the radicals R ¹⁰ or R ^{12 can form} a 5- or 6-membered aromatic ring optionally with a halogen atom, a (C ₁ to C ₆ ) alkyl group, a (C ₁ to C ₆ ) -hydroxyalkyl group, a (C ₂ to C ₆ ) -polyhydroxyalkyl group, a (C ₁ to C ₆ ) -alkoxy group, a (C ₁ to C ₆ ) -hydroxyalkoxy group, a nitro group, a hydroxy group, a group R ^V R ^{VI represents} N- (CH ₂ ) _s -, in which R ^V and R ^VI independently of one another represent a hydrogen atom, a (C ₁ to C ₆ ) -alkyl group, a (C ₁ to C ₆ ) -hydroxyalkyl group or an aryl- ( C ₁ to C ₆ ) -alkyl group and s is a number 0, 1, 2, 3, 4, 5 or 6 may be substituted,
• Y is an oxygen atom, a sulfur atom or a group NR ^VII in which R ^VII represents a hydrogen atom, an aryl group, a heteroaryl group, a (C ₁ to C ₆ ) alkyl group or an aryl (C ₁ to C ₆ ) alkyl group,
• • X- stands for a physiologically compatible anion.

At least one group R ¹⁰ or R ¹² according to formula (CH-3) necessarily stands for a (C ₁ to C ₆ ) -alkyl group. This alkyl group preferably carries at least two hydrogen atoms on its α-carbon atom. Particularly preferred alkyl groups are the methyl, ethyl, propyl, n-butyl, iso-butyl, n-pentyl, neo-pentyl, n-hexyl group. Most preferably, R ¹⁰ and R ¹² are each independently hydrogen or a methyl group, wherein at least one group R ¹⁰ or R ^{12 is} a methyl group.

In In a preferred embodiment, Y is of the formula (CH-3) for an oxygen or a sulfur atom, more preferred for an oxygen atom.

The radical R ^{8 of} the formula (CH-3) is preferably selected from a (C ₁ to C ₆ ) -alkyl group (particularly preferably a methyl group), a (C ₂ to C ₆ ) -alkenyl group (in particular an allyl group), a ( C ₂ to C ₆ ) hydroxyalkyl group (especially a 2-hydroxyethyl group) or an optionally substituted benzyl group.

R ^{11 of} the formula (CH-3) is preferably a hydrogen atom.

Particularly preferred in formula (CH-3) are the radicals R ⁹ , R ¹⁰ and R ^{12 is} a methyl group, the radical R ^{11 is} a hydrogen atom, Y is an oxygen or sulfur atom and the radical R ⁸ is selected from a ( C ₁ to C ₆ ) alkyl group (particularly preferably a methyl group), a (C ₂ to C ₆ ) alkenyl group (especially an allyl group), a (C ₂ to C ₆ ) hydroxyalkyl group (especially a 2-hydroxyethyl group) or a optionally substituted benzyl group.

• – 2-(2-Furoyl)-acetonitril,
• – 2-(5-Brom-2-furoyl)-acetonitril,
• – 3-(2,5-Dimethyl-3-furyl)-3-oxopropanitril,
• – 2-(2-Thenoyl)-acetonitril,
• – 2-(3-Thenoyl)-acetonitril,
• – 2-(5-Fluor-2-thenoyl)-acetonitril,
• – 2-(5-Chlor-2-thenoyl)-acetonitril,
• – 2-(5-Brom-2-thenoyl)-acetonitril,
• – 2-(5-Methyl-2-thenoyl)-acetonitril,
• – 2-(2,5-Dimethylpyrrol-3-oyl)-acetonitril,
• – 2-(1,2,5-Trimethypyrrol-3-oyl)-acetonitril,
• – 2-(Cyanmethyl)-benzimidazol,
• – 1H-Benzothiazol-2-ylacetonitril,
• – 2-(Pyrid-2-yl)-acetonitril,
• – 2,6-Bis(cyanmethyl)-pyridin,
• – 2-(Indol-3-oyl)-acetonitril,
• – 2-(2-Methyl-indol-3-oyl)-acetonitril,
• – 2-(6-Hydroxy-4,7-dimethoxy-1-benzofuran-5-oyl)-acetonitril

und den Salzen mit physiologisch verträglichem Gegenion X^– des

• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxo-pyrimidiniums,
• – 1,2-Dihydro-1,3-diethyl-4,6-dimethyl-2-oxo-pyrimidiniums,
• – 1,2-Dihydro-1,3-dipropyl-4,6-dimethyl-2-oxo-pyrimidiniums,
• – 1,2-Dihydro-1,3-di(2-hydroxyethyl)-4,6-dimethyl-2-oxo-pyrimidiniums,
• – 1,2-Dihydro-1,3-diphenyl-4,6-dimethyl-2-oxo-pyrimidiniums,
• – 1,2-Dihydro-1,3,4-trimethyi-2-oxo-pyrimidiniums,
• – 1,2-Dihydro-1,3-diethyl-4-methyl-2-oxo-pyrimidiniums,
• – 1,2-Dihydro-1,3-dipropyl-4-methyl-2-oxo-pyrimidiniumis,
• – 1,2-Dihydro-1,3-di(2-hydroxyethyl)-4-methyl-2-oxo-pyrimidiniums,
• – 1,2-Dihydro-1,3-diphenyl-4-methyl-2-oxo-pyrimidiniums,
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyi-2-oxo-pyrimidiniums,
• – 1,2-Dihydro-1-(2-hydroxyethyl)-3,4,6-trimethyl-2-oxo-pyrimidiniums,
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-thioxo-pyrimidiniums,
• – 1,2-Dihydro-1,3-diethyl-4,6-dimethyl-2-thioxo-pyrimidiniums,
• – 1,2-Dihydro-1,3-dipropyl-4,6-dimethyl-2-thioxo-pyrimidiniums,
• – 1,2-Dihydro-1,3-di(2-hydroxyethyl)-4,6-dimethyl-2-thioxo-pyrimidiniums,
• – 1,2-Dihydro-1,3-diphenyl-4,6-dimethyl-2-thioxo-pyrimidiniums,
• – 1,2-Dihydro-1,3,4-trimethyl-2-thioxo-pyrimidiniums,
• – 1,2-Dihydro-1,3-diethyl-4-methyl-2-thioxo-pyrimidiniums,
• – 1,2-Dihydro-1,3-dipropyl-4-methyl-2-thioxo-pyrimidiniums,
• – 1,2-Dihydro-1,3-di(2-hydroxyethyl)-4-methyl-2-thioxo-pyrimidiniums,
• – 1,2-Dihydro-1,3-diphenyl-4-methyl-2-thioxo-pyrimidiniums,
• – 1,2-Dihydro-3,4-dimethyl-2-oxo-chinazoliniums und
• – 1,2-Dihydro-3,4-dimethyl-2-thioxo-chinazoliniums

eingesetzt wird. Daher sind die Verbindungen dieser Gruppe besonders bevorzugt.Very particularly brilliant hair colorations can be obtained if the C, H-acidic compound of the formula (CH-1) and / or the formula (CH-2) contained in agent (B2) comprises a compound selected from at least one compound of the group consisting of

• 2- (2-furoyl) -acetonitrile,
• 2- (5-bromo-2-furoyl) -acetonitrile,
• 3- (2,5-dimethyl-3-furyl) -3-oxopropanitrile,
• 2- (2-thenoyl) -acetonitrile,
• 2- (3-thenoyl) -acetonitrile,
• 2- (5-fluoro-2-thenoyl) -acetonitrile,
• 2- (5-chloro-2-thenoyl) -acetonitrile,
• 2- (5-bromo-2-thenoyl) -acetonitrile,
• 2- (5-methyl-2-thenoyl) -acetonitrile,
• 2- (2,5-dimethylpyrrol-3-oyl) -acetonitrile,
• 2- (1,2,5-trimethypyrrol-3-oyl) -acetonitrile,
• 2- (cyanomethyl) benzimidazole,
• 1H-benzothiazol-2-ylacetonitrile,
• 2- (pyrid-2-yl) -acetonitrile,
• 2,6-bis (cyanomethyl) pyridine,
• 2- (indol-3-oyl) -acetonitrile,
• 2- (2-methylindol-3-oyl) -acetonitrile,
• - 2- (6-hydroxy-4,7-dimethoxy-1-benzofuran-5-oyl) -acetonitrile

and the salts with physiologically compatible counterion X ^- des

• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxo-pyrimidinium,
• 1,2-dihydro-1,3-diethyl-4,6-dimethyl-2-oxo-pyrimidinium,
• 1,2-dihydro-1,3-dipropyl-4,6-dimethyl-2-oxo-pyrimidinium,
• 1,2-dihydro-1,3-di (2-hydroxyethyl) -4,6-dimethyl-2-oxo-pyrimidinium,
• 1,2-dihydro-1,3-diphenyl-4,6-dimethyl-2-oxo-pyrimidinium,
• 1,2-dihydro-1,3,4-trimethyl-2-oxo-pyrimidinium,
• 1,2-dihydro-1,3-diethyl-4-methyl-2-oxo-pyrimidinium,
• 1,2-dihydro-1,3-dipropyl-4-methyl-2-oxopyrimidinium,
• 1,2-dihydro-1,3-di (2-hydroxyethyl) -4-methyl-2-oxo-pyrimidinium,
• 1,2-dihydro-1,3-diphenyl-4-methyl-2-oxo-pyrimidinium,
• 1-allyl-1,2-dihydro-3,4,6-trimethyl-2-oxo-pyrimidinium,
• 1,2-dihydro-1- (2-hydroxyethyl) -3,4,6-trimethyl-2-oxo-pyrimidinium,
• 1,2-dihydro-1,3,4,6-tetramethyl-2-thioxo-pyrimidinium,
• 1,2-dihydro-1,3-diethyl-4,6-dimethyl-2-thioxo-pyrimidinium,
• 1,2-dihydro-1,3-dipropyl-4,6-dimethyl-2-thioxo-pyrimidinium,
• 1,2-dihydro-1,3-di (2-hydroxyethyl) -4,6-dimethyl-2-thioxo-pyrimidinium,
• 1,2-dihydro-1,3-diphenyl-4,6-dimethyl-2-thioxo-pyrimidinium,
• 1,2-dihydro-1,3,4-trimethyl-2-thioxo-pyrimidinium,
• 1,2-dihydro-1,3-diethyl-4-methyl-2-thioxo-pyrimidinium,
• 1,2-dihydro-1,3-dipropyl-4-methyl-2-thioxo-pyrimidinium,
• 1,2-dihydro-1,3-di (2-hydroxyethyl) -4-methyl-2-thioxo-pyrimidinium,
• 1,2-dihydro-1,3-diphenyl-4-methyl-2-thioxo-pyrimidinium,
• 1,2-dihydro-3,4-dimethyl-2-oxo-quinazolinium and
• 1,2-dihydro-3,4-dimethyl-2-thioxo-quinazolinium

is used. Therefore, the compounds of this group are particularly preferred.

Has according to the invention it has proved to be preferred when the C, H-acidic compound of the By means of (B2) is selected from the physiologically acceptable Salts of 1-allyl-1,2-dihydro-3,4,6-trimethyl-2-oxo-pyrimidinium, 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium and 2- (cyanomethyl) -benzimidazole. Particularly preferred according to the invention are agents (B2), which necessarily a salt of 1-allyl-1,2-dihydro-3,4,6-trimethyl-2-oxo-pyrimidinium and optionally 2- (cyanomethyl) benzimidazole.

The CH-acidic compounds of the formula (CH-1) and / or of the formula (CH-2) in the agent (B2) are preferably added in an amount of 0.03 to 65.00 mmol, based on 100 g of the agent (B2) used. Of the Use of 1.00 to 30.00 mmol, based on 100 g of the agent (B2), is particularly preferred.

• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 4-Hydroxy-2-methoxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 3,4-Dihydroxy-5-methoxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2,4-Dimethoxy-benzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 4-Hydroxy-2-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 4-Hydroxy-2-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1-Allyl,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 4-Hydroxy-2-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 4-Hydroxy-2-methoxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2,4-Dimethoxy-benzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 4-Hydroxy-2-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 4-Hydroxy-2-methoxybenzaldehyd + 2,3-Dihydro-1,5-demethyl-3-oxo-2-phenyl-1H-pyrazol-4carboxaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 4-Hydroxy-2-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 4-Hydroxy-2-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 4-Hydroxy-2-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 4-Hydroxy-2-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Chior-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 3,4-Dihydroxy-5-methoxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2,4-Dimethoxy-benzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2,4-Dimethoxy-benzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 2,4-Dimethoxy-benzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 2,4-Dimethoxy-benzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethy-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-pheny-1H-pyrazol-4-carboxaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium-bromid + 2-(Cyanmethyl)-benzimidazol + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 2,4-Dimethoxy-benzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 2,4-Dimethoxy-benzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dhydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-(Cyanmethyl)-benzimidazol + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 3,4-Dihydroxy-5-methoxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2,4-Dimethoxy-benzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2,4-Dimethoxy-benzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 4-Hydroxy-2-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 1,2-Dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium-hydrogensulfat + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 2,4-Dimethoxy-benzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 2-Brom-3,4-dihydroxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 2,4-Dimethoxy-benzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 4-Hydroxy-2-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 3,4-Dihydroxy-5-methoxybenzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2,4-Dimethoxy-benzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd
• – 2-(Cyanmethyl)-benzimidazol + 2,4-Dimethoxy-benzaldehyd + 2-Chlor-3,4-dihydroxybenzaldehyd + 2-Brom-3,4-dihydroxybenzaldehyd

According to the invention, the following combinations of C, H-acidic compound and reactive carbonyl compound have proved to be particularly advantageous:

• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 4-hydroxy-2-methoxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 3,4-dihydroxy-5-methoxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4 carboxaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2,4-dimethoxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2-chloro-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 4-hydroxy-2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 4-hydroxy-2-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2 phenyl-1H-pyrazole-4-carboxaldehyde
• - 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 4-hydroxy-2-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde
• 1-Allyl, 2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 4-hydroxy-2-methoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• - 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 4-hydroxy-2-methoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• - 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo -2-phenyl-1H-pyrazole-4-carboxaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 3,4-dihydroxy-5-methoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 3,4-dihydroxy-5-methoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4 carboxaldehyde + 2,4-dimethoxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4 carboxaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4 carboxaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2,4-dimethoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2,4-dimethoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2-chloro-3,4-dihydroxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 4-hydroxy-2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,3-dihydro-1 , 5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde
• - 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 4-hydroxy-2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 4-hydroxy-2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde + 2-chloro-3,4 -dihydroxybenzaldehyd
• - 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 4-hydroxy-2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde + 2-bromo-3,4 -dihydroxybenzaldehyd
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 4-hydroxy-2-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2 -phenyl-1H-pyrazole-4-carboxaldehyde + 2,4-dimethoxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 4-hydroxy-2-methoxybenzaldehyde + 2,3-dihydro-1,5-demethyl-3-oxo-2 -phenyl-1H-pyrazole-4-carboxaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 4-hydroxy-2-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2 -phenyl-1H-pyrazole-4-carboxaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 4-hydroxy-2-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 4-hydroxy-2-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 4-hydroxy-2-methoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde + 2-bromo-3,4 -dihydroxybenzaldehyd
• - 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo 2-phenyl-1H-pyrazole-4-carboxaldehyde + 2,4-dimethoxy-benzaldehyde
• - 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo 2-phenyl-1H-pyrazole-4-carboxaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• - 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo 2-phenyl-1H-pyrazole-4-carboxaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,4-dimethoxy-benzaldehyde + 2-chloro-3,4 -dihydroxybenzaldehyd
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,4-dimethoxy-benzaldehyde + 2-bromo-3,4 -dihydroxybenzaldehyd
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 3,4-dihydroxy-5-methoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde + 2-bromo-3 , 4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4 carboxaldehyde + 2,4-dimethoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4 carboxaldehyde + 2,4-dimethoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4 carboxaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2,4-dimethoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde + 2-bromo-3,4 -dihydroxybenzaldehyd
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy -2-methoxy benzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate +3.4 dihydroxy-5-methoxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate +2,3 dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2,4 dimethoxy-benzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2-chloro -3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2-bromo -3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy 2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy 2-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy 2-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy 2-methoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy 2-methoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate +3.4 Dihydroxy-5-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate +3.4 Dihydroxy-5-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate +3.4 Dihydroxy-5-methoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate +3.4 Dihydroxy-5-methoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate +2,3 Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2,4-dimethoxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate +2,3 Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate +2,3 Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2,4 -Dimethoxy-benzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2,4 -Dimethoxy-benzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2-chloro 3,4-dihydroxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy 2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy 2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,4-dimethoxy-benzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy 2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy 2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxo-pyo rimidinium hydrogen sulfate + 4-hydroxy-2-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2,4-dimethoxy-benzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy 2-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy 2-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy 2-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy 2-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy 2-methoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate +3.4 Dihydroxy-5-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2,4-dimethoxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate +3.4 Dihydroxy-5-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate +3.4 Dihydroxy-5-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate +3.4 Dihydroxy-5-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate +3.4 Dihydroxy-5-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate +3.4 Dihydroxy-5-methoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate +2,3 Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2,4-dimethoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate +2,3 Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2,4-dimethoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate +2,3 Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2,4 -Dimethoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) -benzimidazole + 4-hydroxy-2-methoxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) -benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) -benzimidazole + 2,3-dihydro-1,5-dimethyl-3-oxo-2 phenyl-1H-pyrazole-4-carboxaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) benzimidazole + 2,4-dimethoxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) benzimidazole + 2-chloro-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) benzimidazole + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) -benzimidazole + 4-hydro xy-2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) -benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2,3-dihydro-1,5 dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) -benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2,4-dimethoxy-benzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) -benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,3-dihydro-1 , 5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) -benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde + 2-chloro-3,4 -dihydroxybenzaldehyd
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde + 2-bromo-3,4 -dihydroxybenzaldehyd
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) -benzimidazole + 2,3-dihydro-1,5-dimethyl-3-oxo-2 -phenyl-1H-pyrazole-4-carboxaldehyde + 2,4-dimethoxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) -benzimidazole + 2,3-dihydro-1,5-dimethyl-3-oxo-2 -phenyl-1H-pyrazole-4-carboxaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) -benzimidazole + 2,3-dihydro-1,5-dimethyl-3-oxo-2 -phenyl-1H-pyrazole-4-carboxaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) -benzimidazole + 2,4-dimethoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) benzimidazole + 2,4-dimethoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) -benzimidazole + 2-chloro-3,4-dihydroxybenzaldehyde + 2-bromo-3,4 -dihydroxybenzaldehyd
• - 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde
• - 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,4-dimethoxy-benzaldehyde
• - 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• - 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) -benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2,3-dihydro-1,5 -dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2,4-dimethoxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) -benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2,3-dihydro-1,5 -dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) -benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2,3-dihydro-1,5 -dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) -benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde + 2 chloro-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) -benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde + 2 bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) -benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,3-dihydro-1 , 5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2,4-dimethoxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,3-dihydro-1 , 5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) -benzimidazole + 3,4-dihy droxy-5-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) -benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) -benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde + 2-chloro-3,4 -dihydroxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) -benzimidazole + 2,3-dihydro-1,5-dimethyl-3-oxo-2 -phenyl-1H-pyrazole-4-carboxaldehyde + 2,4-dimethoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) -benzimidazole + 2,3-dihydro-1,5-dimethyl-3-oxo-2 -phenyl-1H-pyrazole-4-carboxaldehyde + 2,4-dimethoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) -benzimidazole + 2,3-dihydro-1,5-dimethyl-3-oxo-2 -phenyl-1H-pyrazole-4-carboxaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide + 2- (cyanomethyl) benzimidazole + 2,4-dimethoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl -1H-pyrazole-4-carboxaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 2,4-dimethoxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 2-chloro-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 2-bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl -3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,3-dihydro-1,5 dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,4-dimethoxy-benzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl 1H-pyrazole-4-carboxaldehyde + 2,4-dimethoxy-benzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl 1H-pyrazole-4-carboxaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl 1H-pyrazole-4-carboxaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 2,4-dimethoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 2,4-dimethoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 2-chloro-3,4-dihydroxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde + 2 , 3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde + 2 , 4-dimethoxy-benzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde + 2 chloro-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde + 2 bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl 3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2,4-dimethoxy-benzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl 3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl 3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2,4-dimethoxy-benzaldehyde + 2-chloro -3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2,4-dimethoxy-benzaldehyde + 2-bromo -3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde + 2 bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,3-dihydro-1,5 -dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2,4-dimethoxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,3-dihydro-1,5 -dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,3-dehydro-1,5 -dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde + 2 chloro-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde + 2 bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl 1H-pyrazole-4-carboxaldehyde + 2,4-dimethoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl 1H-pyrazole-4-carboxaldehyde + 2,4-dimethoxy-benzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl 1H-pyrazole-4-carboxaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2- (cyanomethyl) benzimidazole + 2,4-dimethoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde + 2 bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy-2-methoxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 3,4-dihydroxy-5-methoxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2,4-dimethoxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2-chloro-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2-bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy-2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy-2-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl -1H-pyrazole-4-carboxaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy-2-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy-2-methoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy-2-methoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2 phenyl-1H-pyrazole-4-carboxaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,4-dimethoxy-benzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 3,4-dihydroxy-5-methoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 3,4-dihydroxy-5-methoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2,4-dimethoxy-benzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2,4-dimethoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2,4-dimethoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2-chloro-3,4-dihydroxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy-2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,3-dihydro-1,5 dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy-2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy-2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy-2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy-2-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl 1H-pyrazole-4-carboxaldehyde + 2,4-dimethoxy-benzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy-2-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl 1H-pyrazole-4-carboxaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy-2-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl 1H-pyrazole-4-carboxaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy-2-methoxybenzaldehyde + 2,4-dimethoxy-benzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy-2-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 4-hydroxy-2-methoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2 -phenyl-1H-pyrazole-4-carboxaldehyde + 2,4-dimethoxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2 -phenyl-1H-pyrazole-4-carboxaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2 -phenyl-1H-pyrazole-4-carboxaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 3,4-dihydroxy-5-methoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde + 2-bromo-3,4 -dihydroxybenzaldehyd
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2,4-dimethoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2,4-dimethoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfate + 2,4-dimethoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• - 2- (cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde
• - 2- (cyanomethyl) benzimidazole + 2,4-dimethoxy-benzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 2-chloro-3,4-dihydroxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 2-bromo-3,4-dihydroxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde
• - 2- (Cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde
• - 2- (Cyanomethyl) benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2,4-dimethoxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 2,4-dimethoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• - 2- (cyanomethyl) benzimidazole + 2,4-dimethoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 2-chloro-3,4-dihydroxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole -4-carboxaldehyde
• - 2- (Cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde hyd + 2-chloro-3,4-dihydroxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 3,4-dihydroxy-5-methoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2,4-dimethoxy benzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2-chloro-3 , 4-dihydroxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2-bromo-3 , 4-dihydroxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 4-hydroxy-2-methoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2.4 dimethoxy-benzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2-chloro -3,4-dihydroxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2-bromo -3,4-dihydroxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde + 2,4-dimethoxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 3,4-dihydroxy-5-methoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2,4-dimethoxybenzaldehyde + 2-chloro-3 , 4-dihydroxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2,4-dimethoxybenzaldehyde + 2-bromo-3 , 4-dihydroxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde + 2-bromo -3,4-dihydroxybenzaldehyde
• - 2- (Cyanomethyl) benzimidazole + 2,4-dimethoxybenzaldehyde + 2-chloro-3,4-dihydroxybenzaldehyde + 2-bromo-3,4-dihydroxybenzaldehyde

In the context of the work on which this invention is based, it has also been possible to show that the different relevant nuances can preferably be obtained from mixtures of the substances indicated in the following table in the stated mixing ratio (stated in% by weight): black brown copper red 1-allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide 10-15 0-12 0-10 0-10 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogensulphate - 0-5 0-10 0-10 2- (cyanomethyl) benzimidazole 0-4 0-8 0-8 0-8 4-hydroxy-2-methoxybenzaldehyde 0.5-4 0.5-5 0.5-15 0.5-15 3,4-dihydroxy-5-methoxybenzaldehyde 8-15 0.5-10 0-0.5 0-0.5 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde 0-6 0-6 0-8 0-6 2,4-dimethoxy-benzaldehyde 0-5 0-5 0-8 0-5 2-chloro-3,4-dihydroxybenzaldehyde 8-15 0.2-10 0-1.5 0-4 2-bromo-3,4-dihydroxybenzaldehyde 8-15 0.2-10 0-1.5 0-4

In a further embodiment, in the agent (B1) and / or in the agent (B2) additionally at least one developer component and optionally at least one coupler component may be present as oxidation dye precursors. However, it is preferred that the agents according to the invention are free from oxidation to formulate dye precursors, especially if the risk of allergies for para-allergic is to be minimized.

Regarding the developers and developers usable in the agents (B1) and / or (B2) Coupler components should be explicitly referred to above Remarks on the means (A) referenced.

in the Framework of the underlying this application could work Furthermore, it is surprisingly found that a method in the Asian gray hair with a dye based on specially selected reactive carbonyl compounds and C, H-acidic compounds are not colored to the above leads to these adverse effects.

• – mindestens einem Mittel (B1), das in einem kosmetischen Träger 4-Hydroxy-2-methoxybenzaldehyd sowie mindestens eine weitere reaktive Carbonylverbindung ausgewählt aus 2-Chlor-3,4-dihydroxybenzaldehyd, 2-Brom-3,4-dihydroxybenzaldehyd, 3,4-Dihydroxy-5-methoxybenzaldehyd, 2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-carboxaldehyd und 2,4-Dimethoxybenzaldehyd enthält, und
• – mindestens einem Mittel (B2), das in einem kosmetischen Träger 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxo-pyrimidinium-bromid und gegebenenfalls 2-(Cyanmethyl)-benzimidazol enthält,

durch Mischung erhalten wird.A second subject of the present invention is therefore a process for dyeing gray-haired Asian hair, in which the grayed hair parts are treated with an agent (B) immediately before use

• At least one agent (B1) which comprises in a cosmetic vehicle 4-hydroxy-2-methoxybenzaldehyde and at least one further reactive carbonyl compound selected from 2-chloro-3,4-dihydroxybenzaldehyde, 2-bromo-3,4-dihydroxybenzaldehyde, 3, Contains 4-dihydroxy-5-methoxybenzaldehyde, 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde and 2,4-dimethoxybenzaldehyde, and
• At least one agent (B2) containing in a cosmetic carrier 1-allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide and optionally 2- (cyanomethyl) -benzimidazole,

obtained by mixing.

Regarding the inventively preferred combinations be explicitly at this point on the comments on first subject of the present invention. Either in the context of the first subject as well as in the context of the second Subject of the present invention have the following Conditions proved advantageous.

While the work underlying this invention has been found that the storage stability of the reactive carbonyl compounds be increased considerably when the agent (B1) is the reactive carbonyl compound (s) in a cosmetic carrier, wherein the pH of this agent is between 2 and 5.

Furthermore was found to be the stability of the special CH-acidic compounds can be increased if the agent (B2) contains them in a cosmetic carrier and having a pH of 0.5 to 2.5. By this measure increases the stability of the formulation in a measure that it is also in storage over for several months to no significant reduction in the content of CH-acidic Connection is coming.

Especially Store-stable formulations can be obtained if the agent (B1) has a pH between 3 and 4.5, therefore this pH range is particularly preferred.

Of Furthermore, it is particularly preferred if the agent (B2) has a pH of 1 to 2, and particularly preferably a pH of 1.1 to 1.9.

at The pH values for the purposes of the present invention are to pH values measured at a temperature of 22 ° C become.

The Adjustment of the pH in the agents (B1) and / or (B2) can with the help of an organic or inorganic acid like for example hydrochloric acid, sulfuric acid, hydrobromic acid, Phosphoric acid, acetic acid, tartaric acid, Citric acid, lactic acid, malic acid or glycolic acid.

In In this context, the setting of the invention pH values with the aid of sulfuric acid, hydrochloric acid, Tartaric acid, citric acid, malic acid or lactic acid is particularly preferred.

in the Within the scope of the method according to the invention the agents (B1) and (B2) just before application to the hair fiber intimately mixed with each other.

to However, it may be possible to further improve the staining result be beneficial, the staining itself in a pH range from 7 to 10.

Therefore can in a particular embodiment of the invention Method of mixing of the means (B1) and (B2) a third Component (B3) which is in a cosmetic carrier contains at least one alkalizing agent. It is preferred according to the invention when the agent (B3) has a pH of 7 to 10.

Farther it is preferred, although the ready-to-use means (B) after Addition of the agent (B3) has a pH of 7 to 10.

at that contained in agent (B3) in a cosmetic carrier Alkalizing agents may preferably be alkalizing agents selected from the group formed from ammonia, basic amino acids, alkali hydroxides, alkanolamines, Alkali metal metasilicates, urea, morpholine, N-methylglucamine, Imidazole, alkali phosphates and alkali hydrogen phosphates used become. The alkali metal ions used are preferably lithium, sodium, Potassium, especially sodium or potassium.

The usable as alkalizing agent according to the invention basic amino acids are preferably selected from the group formed from L-arginine, D-arginine, D, L-arginine, L-histidine, D-histidine, D, L-histidine, L-lysine, D-lysine, D, L-lysine. L-arginine, D-arginine, D, L-arginine are particularly preferred as an alkalizing used in the context of the invention.

The usable as alkalizing agent according to the invention Alkali hydroxides are preferably selected from the group which is formed from sodium hydroxide and potassium hydroxide.

The alkanolamines which can be used as alkalizing agents according to the invention are preferably selected from primary amines having a C ₂ -C ₆ -alkyl basic body which carries at least one hydroxyl group. Particularly preferred alkanolamines are selected from the group formed from 2-aminoethan-1-ol (monoethanolamine), 3-aminopropan-1-ol, 4-aminobutan-1-ol, 5-aminopentan-1-ol, 1 -Aminopropan-2-ol, 1-aminobutan-2-ol, 1-aminopentan-2-ol, 1-aminopentan-3-ol, 1-aminopentan-4-ol, 3-amino-2-methylpropan-1-ol , 1-amino-2-methylpropan-2-ol, 3-aminopropane-1,2-diol, 2-amino-2-methylpropane-1,3-diol. Very particularly preferred alkanolamines according to the invention are selected from the group consisting of 2-aminoethane-1-ol, 2-amino-2-methylpropan-1-ol and 2-amino-2-methylpropane-1,3-diol.

Especially Preferably, the alkalizing agent is selected from at least one compound from the group that is formed from Ammonia, 2-aminoethanol, 2-amino-2-methylpropan-1-ol, 2-amino-2-methyl-propane-1,3-diol, Potassium hydroxide, sodium hydroxide, L-arginine, D-arginine, DL-arginine, N-methylglucamine, morpholine, imidazole and urea.

Completely according to the invention Particularly preferred alkalizing agents are monoethanolamine, ammonia, sodium hydroxide, Potassium hydroxide and / or arginine.

Of Further, pH can also be greater as 7 set buffer systems in means (B3) are used.

When pH buffer system according to the invention chemical compounds or a combination of chemical compounds viewed in a solution that cause the pH of the solution with the addition of a small amount of acid or lye changes only slightly to a volume of the cosmetic carrier. This change is less pronounced than this with the addition of the same amount of acid or alkali to an equal volume of the cosmetic carrier without pH buffer system is the case.

Such pH buffer systems are preferably selected from among at least one member selected from bicarbonate, organic acid (especially citric acid) / monohydrogen phosphate, malic acid (especially citric acid) / dihydrogen phosphate, tris (hydroxymethyl) aminomethane / maleic acid / NaOH, Tris (hydroxymethyl) aminomethane / maleic acid / KOH, tris (hydroxymethyl) aminomethane / HCl, monohydrogenphosphate / dihydrogenphosphate, dihydrogenphosphate / NaOH, dihydrogenphosphate / KOH, H ₃ BO ₃ / KCl / NaOH, H ₃ BO ₃ / KCl / KOH, borate / HCl , Borate / halide (especially chloride such as potassium chloride) / NaOH, borate / halide (especially chloride such as potassium chloride) / KOH, Theorell and Stenhagen buffer system, McIlvine buffer system, glycine / NaOH and glycine / KOH. Particularly preferred pH buffer systems are selected from at least one member of the group formed from tris (hydroxymethyl) aminomethane / maleic acid / NaOH, tris (hydroxymethyl) aminomethane / maleic acid / KOH, tris (hydroxymethyl) aminomethane / HCl, borate / HCl and H ₃ BO ₃ / KCl / NaOH.

The slashed pH buffer systems from the above list, mixtures of these by the slash The compounds listed in the list are anionic Compounds are in the form of their salts with a corresponding monovalent or polyvalent cation used. Preferred cations are Alkali metal cations (especially sodium or potassium) and ammonium ions. Usable according to the invention in the buffer systems Edible acids are, for example, citric acid, Tartaric acid or malic acid or mixtures thereof.

The pH buffer system is preferably in an amount of 0.1 to 10.0 wt .-%, particularly preferably from 0.3 to 5.0% by weight, very particularly preferably from 0.5 to 3.0 wt .-%, each based on the weight of the application mixture from agent (B1), agent (B2) and agent (B3), in the ready-to-use Colorants included.

In In this context, the pH of the final application mixture, which are prepared by mixing the agents (B1), (B2) and (B3) will be from 7.5 to 11. Is the pH of the final application mixture in a range of 7.5 to 9.0, it is preferred.

The employed in the process according to the invention Means contain the components essential to the invention in one cosmetically acceptable carrier. As such, it is preferred a suitable aqueous, alcoholic or aqueous-alcoholic Carrier used. For the purpose of the present invention such carriers are, for example, creams, emulsions, gels or surfactant-containing foaming solutions, such as for example shampoos, foam aerosols or other preparations, which are suitable for use on the hair. It is but also conceivable, the essential components of the invention in one powdery or tablet-shaped formulation to integrate.

For the purposes of the present invention, aqueous-alcoholic solutions are to be understood as meaning aqueous solutions containing from 3 to 70% by weight of a C ₁ -C ₄ -alcohol, in particular ethanol or isopropanol. The compositions according to the invention may additionally contain further organic solvents, for example methoxybutanol, benzyl alcohol, ethyl diglycol or 1,2-propylene glycol. Preference is given to all water-soluble organic solvents.

in the Frame of a first preferred embodiment, the Agent used according to the invention (B1), (B2) and optionally (B3) adjusted to low viscosity. Application preparations after mixing the components (B1), (B2) and optionally (B3) have a viscosity of 0 to 2000 mPas (measured at 22 ° C in the Brookfield viscometer with spindle 4 and a Speed of 4 rpm), have proved to be particularly preferred. A viscosity of 0 to 1000 mPas, measured under the mentioned conditions, according to the invention is particularly prefers. A viscosity of 50 to 500 mPas (measured at 20 ° C (Brookfield viscometer type RV-T, spindle 4 with a rotational speed of 20 rpm) is complete according to the invention particularly preferred.

in the Within this embodiment of the present invention it has proved to be advantageous, the ready-to-use means (B) by means of an application device (1) with at least one Container (2) for receiving the agent (B), with an application head (3) connected to the at least one container (2) is and has a porous application body (B1), Apply on human hair by painting over.

A advantageous design of the actual application device provides that the porous body of the order to Achieving a capillary effect has continuous pores. The capillary properties of the application body, with the means (B) are wickedly connected, provide for a reliable transport of the agent (B) from the at least a container and a metered order of the agent (B) by stroking on the fibers. According to one further developed variant of the application device, the application body preferably a fibrous, sponge, foam, felt or sintered material type Material structure on. This material structure causes the desired Capillary action of the application body, so that, for example an unwanted leakage or dripping of the agent (B) from the applicator body is omitted, but at the same time a reliable fluid delivery is guaranteed by means of the job body.

alternative to a substantially block-shaped configuration of the porous This body can also be several pen-shaped Have protrusions. This enlarges the effective surface of the application body and thus improves the order of the agent (B). Consequently, by means of the swipe movement of the application body over the Hair quantitatively and qualitatively a better coloring result guaranteed.

A Another useful embodiment of the application device is achieved in that the application head several, if necessary having detachably arranged, comb teeth. These Comb teeth are in particular adjacent to the application body arranged. The stroke of the entire application head during the application provides by means of comb teeth initially for a disentanglement of the hair and thus especially for a steady order of the agent (B). Basically, the releasable allows Arrangement of the comb teeth on the application head a more versatile Use of the application device. It turns out for Such an arrangement is also advantageous when the comb teeth opposite the porous applicator body protrude. A preferred embodiment of the application device consists in the comb teeth of the application head circular to arrange around the applicator body. Independently from the respective stroking direction during the application in each case unraveled the hair first, before the actual application of the agent (B) takes place.

Farther it is essential to the invention that the actual agent (B) only immediately before use by mixing the preparation (B1), (B2) and optionally (B3) is produced. In particular as a result often insufficient storage stability of the Mixture are appropriately designed as part of the overall device Storage and mixing tank required. The suitable designed storage and mixing containers guarantee on the one hand adequate storage stability before use the individual components of the agent (B) and ensure on the other hand, an appropriate handling of the overall device during the application. There are different ones for this Variants of the application device possible. These different ones Variants is common, that is right before the application the already mixed preparation of the application liquid in the container of the invention Device is located. Here is the container with the application head connected. For the container is a variety of design options conceivable. For example This container is ergonomic in its design the application process to be adapted to the user handling facilitate the application device.

Of the Container can both as a separate application container be executed, in which before the start of the application the ready mixed preparation of the application liquid is filled. Similarly, it is also conceivable that the container is used both as an application container, as well as before the application serves as a mixing container. mixing tank and application containers are in this variant so identical and form the container. For both design variants A variety of possibilities are described below Design mixing vessel constructive.

Around a mixture of preparations (B1), (B2) and optionally (B3) there are a lot of ways some of which are listed here by way of example.

So there is a possibility to the user in a first embodiment the present invention three or more containers to the To give a hand. The first container contains the means (B1), the second container means (B2), the third container serves as a mixing container and a fourth container may optionally contain the agent (B3). Further additional storage containers are possible. For the preparation of the mixture becomes from the two respectively three storage containers the desired amount in given the mixing container, this closed, and the Components are, for example, by subsequent Shaking the mixing container mixed together. The mixing process can be accelerated by the fact that internals in the mixing container when shaking a turbulent Flow (high Reynolds numbers) and thus the mixing process improve and accelerate. In the event that it is at one or more of the components around lumpy or granular components, it may be advantageous be to provide internals in the mixing container such that a mechanical effect on a destruction or but faster solubility of granules respectively aimed at the component pieces. This will be for example by protruding into the mixing container tips or barb-like Elements achieved. Also achieve fixtures in the form of stirrers a similar result.

A another embodiment in the context of the present invention is one or more of the reservoir from one to provide material soluble by a liquid. These soluble storage containers are in the Mixing container given and there by the respective solvent, preferably one component of the mixture to be prepared, dissolved. This embodiment has the user for the Advantage that it during the preparation of the total preparation never in contact with individual in the storage containers packaged components comes. In addition to the dissolution process To accelerate, it may be advantageous, even here mechanical To use internals, which a crushing of the reservoir described and a concomitant increase in speed of the Achieve dissolution process. Advantageously, such soluble storage container designed as a foil bag.

A another variant for the preparation according to the invention Mixtures is the provision of at least two separate containers for storing the respective component, wherein at least one the container also acts as a mixing container. For such embodiments are all above examples of the variant with at least three containers also conceivable within the scope of the present invention.

Either with two storage containers, one of which additionally as a mixing container serves as well as in the variant with at least three containers (ie a separate mixing container) It may be advantageous to provide Umfüllhilfen, which Make sure when refilling from the reservoirs into the mixing tank / combined storage mix tank no single component is spilled. Such Umfüllhilfen are for example extended spouts, which allow the nesting of reservoir and mixing container and means for fixing the reservoir to the mixing container during the transfer process. Such fixative are, for example snap snap-in connections, screw or bayonet locks.

Around Making the transfer even faster can be beneficial be to provide means of pressure equalization between the two Containers during the transfer process provide. Such means are for example within the opening a reservoir arranged pipes, which serve as a snorkel can act. Also disposable valves in the reservoir for pressure equalization are conceivable for such functionalities.

Also helpful to the user is when the reservoir are provided with a closure, which only on a trigger command opens. So the user can make sure the Transfer process only starts when reservoir and mixing container in the for the mixing process correct position. A design option such closures is for example a tear-off, which by an increased internal pressure in the reservoir tears open and thus starts the transfer process. The internal pressure in the reservoir, for example, by Pumping means or by simply squeezing increased become.

Also mechanical destruction of such films by mechanical Aids, such as thorns, or by the contained component itself, for example in the case of tablets, is conceivable.

For example It is also conceivable, the reservoir for granules, Powder or chunky goods as a blister pack execute and additionally provide aids, which allow these blisters above the opening of the To place mixing container. The user of such mixing systems simply pushes through the component contained in the blister the sealing foil through into the mixing container.

Next the variants with three and more containers, or two or more containers, it is also conceivable to provide only a single container, both as a Reservoir as well as a mixing container serves. Such containers must due to the lack of Storage stability of the individual components in mixture with a way to separate the components during be equipped storage. Such a separation can for example be produced by partitions through which a container with two or optionally three separate chambers is formed. The mixture in such a system is generated through the destruction of the dividing walls or through the arrangement of valves in the partitions. At destructible Partitions may be useful, this destructibility either by increasing the internal pressure or by mechanical means from outside the container directly or indirectly. An embodiment such mixing containers, for example, a reservoir be whose destructible partition through the applicator head attached, projecting into the container, mechanical Means is destructible. The destruction takes place in Such a case by screwing or putting on the Applikatorkopfs in the application position instead. Also separate Devices for destroying the partition are self-evident conceivable in the context of the present invention.

Next a destructible partition can also be beneficial to provide a solid partition with a one-way valve. Such a thing One-way valve could, for example, by increasing the internal pressure in one of the chambers open and thus the Transfer component from one chamber to the other chamber. The increase in internal pressure can be achieved by the flexible design of the total container and its compression be achieved by the hand of the user. Also additional Pumping means are quite conceivable.

Next the embodiment of a mixing device with a single container and various chambers separated by partitions, the serve as a reservoir, it may be advantageous in addition to the storage chambers, a mixing chamber empty before the start of the mixing process provided. In such an embodiment is located there is an element between the pantries and the mixing chamber to transfer the components from the individual Panels in the mixing chamber. Such elements can, as already described above embodiments, destructible Be walls, but also one-way valves in the direction of the mixing chamber.

The above-described devices for mixing the components (B1), (B2) and optionally (B3) are of course only Examples and do not limit the present application. Also, combinations of all mixing devices shown above conceivable in the context of the present invention.

in the Within the scope of a second preferred embodiment of the present invention Invention are the means used in the process (B1), (B2) and optionally (B3) set medium viscosity. Application preparations after mixing the components (B1), (B2) and optionally (B3) have a viscosity of 0 to 15,000 mPas (measured at 22 ° C in the Brookfield viscometer with spindle 4 and a Speed of 4 rpm), have proved to be particularly preferred. A viscosity of 500 to 5000 mPas, measured under the mentioned conditions, according to the invention is particularly prefers.

in the Within this embodiment, a dispensing system may be used be having at least two containers, each this container at least one outlet opening having. The outlet openings of the container or the containers themselves are arranged so that the outlet openings isolated from each other.

in the Within a very particularly preferred embodiment comprises the delivery system according to the invention for hair color changing agent exactly two containers, wherein each of these containers has at least one outlet opening having.

The at least two containers can all be for have this purpose conceivable geometries. Even if according to the invention all conceivable container shapes are intended to be such which are cylindrical in shape, according to the invention preferred. But it is also conceivable that containers in the form of figures, such as figures and / or animals are used. Furthermore, of course, from the link the container with each other and with the outlet openings give a different geometry.

The Containers, in particular if they are cylindrical are, for example, a round, an oval, a square, triangular, rectangular or trapezoidal Base area have. According to the invention Also includes containers with such bases be different from the above ground surfaces slight variation, such as a rounding of the corners, result.

According to the invention in principle, all spatial arrangements of the container includes his.

In According to one embodiment, the inventive Dispensing system be designed in one piece.

In In another embodiment, the delivery system comprises for hair color-modifying agents two containers, the one round or square base have rounded corners. The containers are in Frame of this embodiment preferably arranged side by side.

in the Frame of another embodiment of the present invention Invention, the containers have an oval or a rectangular base with rounded corners on. In the context of this embodiment, it may be preferable when the containers are arranged such that the respective show longer outer sides to each other or abut each other.

The preferably two containers can continue geometrically be shaped so that they fit together or into each other and thus mechanically firmly or permanently releasably connected can be.

This can be achieved, for example, in that one container at least partially surrounds the other in its circumference and clamps it in a defined position. An exact positioning of the container to each other can be brought about, for example, that one of the container on its surface locking nubs or locking lugs, which in corresponding recesses or recesses of the engage second container and prevent slipping of the container to each other.

In In another embodiment, the containers also be designed so that one of the containers on his Surface at least one groove and the other container at least one spring engaging therein, so that the container can be put together in this way.

These Embodiment with tongue and groove can in an advantageous Be further developed manner that the groove or the spring locking nubs and accordingly, the spring or groove corresponding thereto Has locking recesses. These latching means, so the locking nubs and recesses, lock the connector of the two interconnected containers, so these be separated only with increased force can.

In a particularly preferred embodiment the containers as two equally shaped halves in a substantially geometrically formed as a truncated cone Be formed output system, wherein the truncated cone at its Narrow side two each arranged laterally of the central axis outlet openings having. Each of the halves, ie the container, thus has a convex outside, which is one half the truncated cone surface forms, and a substantially plane outside on to the halves together issue. Each of the halves is shaped so that the lower part flowing over the entire height of the truncated cone in each offset from the central axis to the side Outlet passes. The plane outside of each one Half furthermore has at least one mechanical connecting element such as tongue and groove, so that the halves be plugged together and firmly connected.

Farther it may be preferred according to the invention, if the at least two plastic containers, containing plastic Multi-layer films, metallized films or metal produced are.

The spatially isolated outlet openings according to the invention are such arranged that a mixing of different means at storage is excluded. It may be preferred according to the invention be when the outlet openings are arranged such that the two or more agents are applying themselves on the hair mix intimately. It can according to the invention about it In addition, also be preferred, the outlet openings in such a way to shape that also a backmixing afterwards to the application is avoided.

in the In one embodiment, the at least two isolated outlet openings two separate applicator attachments be installed. Within the scope of this embodiment, it is preferred according to the invention if the at least two containers are tight respectively firmly-releasably connected with each other and each of them wearing an applicator attachment. It is conceivable according to the invention that two similar but also two different applicator attachments be used.

in the Within the scope of a further embodiment of the present invention can be the at least two spatially isolated Outlets also a common applicator attachment with two separate openings. In the context of this According to the invention, it is preferred if the at least two containers are independent are held together by the common applicator attachment become. However, it may also be conceivable according to the invention Be that at least two containers already with each other are linked and the common applicator attachment a makes additional connection.

The Outlet openings and their spatial environment are According to the invention designed so that they are for application the means are suitable for the hair. Although here, too, the present In principle, the invention is not subject to any restrictions should, it has proved to be advantageous if the applicator attachment designed in such a way that bristles, combs or with cotton wool surrounded rods are arranged around the outlet opening. Furthermore, it may be preferred according to the invention if after at least one outlet opening a sponge is arranged. Likewise, it may be preferred according to the invention be if in at least one outlet opening a fiber composite pure enough. Furthermore, it may be preferred according to the invention be, if after at least one outlet opening a ball valve is arranged.

Completely according to the invention particularly preferred is a circular array of Bristles around the outlet.

Furthermore, it may be very particularly preferred according to the invention, if each of the containers more Having juxtaposed outlet openings. In the context of this embodiment, it may be preferred according to the invention if further application aids, such as, for example, bristles, a sponge, a comb, a rod enveloped by wadding, a ball valve or a fiber composite are arranged in the region of the further outlet opening.

In In a preferred embodiment, the applicator attachment also be further developed in that the edge of an outlet opening at least one of the outlet opening in the flow direction protruding projection has. This can when applying the Means from the associated container on the hair be placed on the scalp, making it a minimal Distance between the exit opening and the scalp is ensured.

Farther The applicator attachment can also be designed so that the edge the outlet opening at two opposite Side has two projections, so that the outlet opening is arranged between the projections. This can be a such applicator opening are placed on the hair so that through the two protrusions a strand of hair is separated from the remaining hair and the means exactly and applied exclusively to the detected strand becomes. Finally, such an applicator tip still by be further developed that the applicator between the projections Bristles or an order sponge has to one uniform order of the agent to be applied sure. In the case of such provided with projections Applicator openings, it has proved to be advantageous if these are arranged spatially so that when you sweep the applicator over the hair all the outlet openings the touch the same strand of hair, making a uniform strand of hair Ensures mixing of the components on the hair is.

Also with regard to the delivery mechanism, the present invention is intended in no way be restricted. This is how the output can be for example, by gravity, by capillary forces or by printing. As examples of the print output are at this point the exercise pressure on flexible walls, internal pressure (aerosol application) and pumping mechanisms mentioned.

in the Frame of a third preferred embodiment of the present invention Invention are the means used in the process (B1), (B2) and optionally (B3) adjusted to high viscosity. Application preparations after mixing the components (B1), (B2) and optionally (B3) have a viscosity of 0 to 20,000 mPas (measured at 22 ° C in the Brookfield viscometer with spindle 4 and a Speed of 4 rpm), have proved to be particularly preferred. A viscosity of 1,000 to 5,000 mPas, measured below the conditions mentioned, according to the invention is particularly prefers

in the Within this embodiment, it has proven to be advantageous proven, the means (B1), (B2) and optionally (B3) in tubes to assemble.

When Laminated according to the invention has particularly suitable Aluminum proved to be tube material. But there are also tubes out Plastic laminate (PE, PET, PP) or plastic coextrudates (PE, PET, PP) conceivable. As very particular according to the invention Preference has been given to tubes made of aluminum laminate, the optionally still protected with a paint or off Plastic laminate are made. Under aluminum laminate according to the invention a understood with plastic coated aluminum layer.

It According to the invention, it is conceivable that the means (B1), (B2) and optionally (B3) in each case separately packed in tubes are. However, it may also be preferred according to the invention be two of the components together in a two-chamber tube too assemble. It is conceivable both the means (B1) and (B2) as well as the means (B1) and (B3) as well as the means (B2) and (B3) to assemble together.

Independently from the distribution on the different tubes can the Agents (B1), (B2) and optionally (B3) immediately before use are removed from the tubes and transferred to a suitable mixing container become. After thorough mixing of the agents (B1), (B2) and optionally (B3), the resulting application mixture then with suitable tools, such as a brush or a comb applied to the hair to be treated become.

It but is also conceivable according to the invention, if from the respective tubes the means (B1), (B2) and optionally (B3) stranded next to each other on a comb. Subsequently, the comb is through the strands to be treated pulled, with a mixing of the various agents occurs and thus the coloration is initiated.

in the Within the scope of this embodiment, it may be preferred according to the invention be to offer the customer a multipart kit that consists of two or optionally three tubes containing the agents (B1), (B2) and optionally (B3) and a suitable comb for application on the hair.

Independently from the form of confectioning the individual means could be positive Effects, in particular an improved paint lift, demonstrated if, in the context of the method according to the invention agents used at least one alkyl phosphoric acid ester contain. Particularly preferred according to the invention is the use of at least one Alkylphosphorsäureesters in the agent (B2). Under alkylphosphoric be According to the invention esters of phosphoric acid understood, wherein at least one alcohol is a derivative of a fatty alcohol is.

wobei R¹, R² und R³ stehen unabhängig voneinander für ein Wasserstoffatom, ein Alkalimetallkation oder einen Rest der Formel (II) stehen

wobei m und n stehen unabhängig voneinander für eine ganze Zahl zwischen 0 und 20 und R⁴ steht für einen gesättigten oder ungesättigten, verzweigten oder unverzweigten C_5-28-Alkylrest, mit der Maßgabe, dass mindestens einer der Reste R¹, R² oder R³ steht für einen Rest der Formel (VI).It may be preferred according to the invention if the agents of the present application contain at least one alkyl phosphoric acid ester of the formula (V)

wherein R ¹ , R ² and R ³ are each independently a hydrogen atom, an alkali metal cation or a radical of the formula (II)

wherein m and n are independently an integer between 0 and 20 and R ⁴ is a saturated or unsaturated, branched or unbranched C _5-28 alkyl radical, with the proviso that at least one of R ¹ , R ² or R ³ is a radical of the formula (VI).

Furthermore, it has proved to be preferred if the agents according to the invention contain at least one alkylphosphoric acid ester of the formula (V) in which one of the radicals R ¹ , R ² or R ^{3 is} a hydrogen atom.

Likewise, it has proved to be advantageous if at least one of the radicals R ¹ , R ² or R ^{3 is} an alkali metal cation, preferably a sodium cation, a potassium cation or a lithium cation. A sodium cation and a potassium cation are most preferred.

Furthermore, it has proved to be preferred for the compositions according to the invention to contain at least one alkylphosphoric acid ester of the formula (V) in which the radical R ⁴ is a saturated or unsaturated, branched or unbranched C _12-22- alkyl radical, in particular an unsaturated alkyl radical , very particularly preferably for an oleyl radical.

Suitable alkyl phosphoric acid esters are for example the diester of phosphoric acid and of ethoxylated lauryl alcohol (INCI name: Dilaureth-4 Phosphate), that sold under the trade name Hostaphat ^® KO 200 from Clariant mixture of mono- and diesters of phosphoric acid and oleyl alcohol (INCI name: Oleyl phosphates), the triesters of phosphoric acid and ethoxylated cetearyl alcohol (INCI name: triceteareth-4 phosphates), the triesters of phosphoric acid and ethoxylated oleyl alcohol (INCI name: trioleth-8 phosphates), the triesters of phosphoric acid and oleyl alcohol (INCI name : Trioleyl Phosphate) and the phosphoric esters with the INCI names Dicetyl Phosphate, Potassium Cetyl Phosphate, Sodium Lauryl Phosphate.

Also preferred are alkyl phosphoric acid esters with partially or perfluorinated alkyl groups, for example those of the general formula (V), in which the radicals R ₁ , R ₂ and R ₃ independently of one another in addition to the abovementioned meanings also for a group R _f - (CH ₂ ) _x - (OCH ₂ CH ₂ ) _y -, where R _{f is} a perfluorinated alkyl radical having 4 to 20, preferably 6 to 18 C atoms, x is a number from 0 to 4, preferably 2 and y is a number from 0 to 20 stands.

Suitable fluorinated alkylphosphoric acid esters are the reaction products of the reaction of fluorinated, optionally ethoxylated alcohols with phosphoric acid, POCl ₃ , P ₄ O ₁₀ or polyphosphoric acid. For example, the diethanolammonium salt of perfluoroalkylethyl phosphate which is sold under the trade name HOE S 2746 by Clariant is suitable.

In It has the framework of the work underlying this invention also proved to be advantageous when the inventive At least two different alkylphosphoric acid esters contain.

invention An agent containing at least one dialkyl phosphoric acid ester and / or at least one ethoxylated monoalkyl phosphoric acid ester, are particularly preferred according to the invention.

Provided the agents according to the invention are two different Alkylphosphoric acid ester has a ratio of ethoxylated monoalkylphosphoric acid ester to dialkylphosphoric acid ester from 1: 5 to 5: 1, especially from 1: 1 to 2: 1, as particularly suitable proved.

A very particularly preferred according to the invention is a combination of Alkylphosphorsäureesterkombination Oleth-5 Phosphate with dioleyl phosphate, as sold for example under the trade name Crodafos ^® HCE by the company Croda.

Farther could be proved during the work on the present application be that the observed effects further amplified can be when the inventive Means additionally at least one optionally ethoxylated and / or propoxylated fatty alcohol.

Under optionally ethoxylated and / or propoxylated fatty alcohols According to the invention adducts of 0 to 30 moles of ethylene oxide, preferably 2 to 25 moles of ethylene oxide, in particular from 10 to 20 mol of ethylene oxide, and / or 0 to 5 mol Propylene oxide to linear fatty alcohols having 8 to 22 carbon atoms.

typical Examples of preferred according to the invention Fatty alcohols are caproic alcohol, caprylic alcohol, 2-ethylhexyl alcohol, Capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, Cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, Oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolyl alcohol, Linolenyl alcohol, elaeostearyl alcohol, arachyl alcohol, gadoleyl alcohol, Behenyl alcohol, erucyl alcohol and brassidyl alcohol and their technical Mixtures z. B. in the high pressure hydrogenation of technical methyl esters based on fats and oils or aldehydes from Roelen's Oxosynthesis and as a monomer fraction in the dimerization of incurred unsaturated fatty alcohols. Especially preferred are technical fatty alcohols with 12 to 18 carbon atoms, like for example, coconut, palm, palm kernel or tallow fatty alcohol.

All particularly preferred is the addition of fatty alcohol ethoxylates, such as ceteareth-12, ceteareth-20 and ceteareth-30.

Furthermore, it has been found to be very particularly preferred according to the invention to use Alkylphosphorsäureesterkombination to which a fatty alcohol ethoxylate has already been added, as for example under the trade names Crodafos ^® CES (INCI name: Cetearyl Alcohol, dicetyl phosphates, ceteth-10 phosphates) and Crodafos ^® CS -20 (INCI name: Cetearyl Alcohol, Dicetyl Phosphate, Ceteth-20 Phosphate) are sold by the company Croda.

The Alkylphosphorsäureester be in the inventive Agent in an amount of preferably 0.01 to 80 wt .-%, especially preferably in an amount of 0.1 to 10 wt .-%, each based on the weight of the ready mix.

Farther it has according to the invention as particularly advantageous to achieve the optimal effects, especially a uniform and intensive paint lift proven when in the context of the invention Procedure used agents containing a solubilizer.

• a) Glycerinmono- und -diester und Sorbitanmono- und -diester von gesättigten und ungesättigten Fettsäuren mit 6 bis 22 Kohlenstoffatomen und deren Ethylenoxidanlagerungsprodukte;
• b) Anlagerungsprodukte von 15 bis 60 Mol Ethylenoxid an Ricinusöl und/oder gehärtetes Ricinusöl sowie
• c) Anlagerungsprodukte von 20 bis 30 Mol Ethylenoxid und/oder 20 bis 20 Mol Propylenoxid an lineare Fettalkohole mit 4 bis 8 C-Atomen und an Alkylphenole mit 8 bis 15 C-Atomen in der Alkylgruppe.

According to the invention particularly vorteihafte solubilizers are

• a) glycerol mono- and diesters and sorbitan mono- and diesters of saturated and unsaturated fatty acids having 6 to 22 carbon atoms and their ethylene oxide addition products;
• b) addition products of 15 to 60 moles of ethylene oxide with castor oil and / or hydrogenated castor oil and
• c) addition products of 20 to 30 moles of ethylene oxide and / or 20 to 20 moles of propylene oxide to linear fat alcohols having 4 to 8 carbon atoms and alkylphenols having 8 to 15 carbon atoms in the alkyl group.

preferred Solubilizers of group a) are, for example, ethoxylated Sorbitan monoesters of lauric or oleic acid, as for example under the INCI names polysorbate-20 and Polysorbate-80 are known.

preferred Solubilizers of group b) are, for example, addition products of about 40 moles of Eo hydrogenated castor oil, as for example under the INCI name PEG-40 Hydrogenated Castor Oil in the trade are available.

One preferred solubilizer of group c) is, for example the adduct of about 26 moles of PPG and about 26 moles of PEG Butyl alcohol, as for example under the INCI name PPG-26-buteth-26 is commercially available.

It has proved to be advantageous according to the invention if the agents used at least two solubilizers from different groups a) to c).

Furthermore It has proved to be particularly preferred when the solubilizers on average (B1), containing at least one reactive carbonyl compound, be used.

The Solubilizers are used in the invention Preferably in an amount of 0.1 to 10 wt .-%, in particular from 0.5 to 6 wt .-%, based on the respective means.

Farther can in the context of the invention Method used all known in such preparations Active substances, additives and auxiliary substances. Included in many cases the ready-to-use colorants at least one surfactant, in principle both anionic and zwitterionic, ampholytic, nonionic and cationic surfactants are suitable. In many cases However, it has proved to be advantageous, the surfactants from anionic, select zwitterionic or nonionic surfactants.

• – lineare Fettsäuren mit 10 bis 22 C-Atomen (Seifen),
• – Ethercarbonsäuren der Formel R-O-(CH₂-CH₂O)_x-CH₂-COOH, in der R eine lineare Alkylgruppe mit 10 bis 22 C-Atomen und x = 0 oder 1 bis 16 ist,
• – Acylsarcoside mit 10 bis 18 C-Atomen in der Acylgruppe,
• – Acyltauride mit 10 bis 18 C-Atomen in der Acylgruppe,
• – Acylisethionate mit 10 bis 18 C-Atomen in der Acylgruppe,
• – Sulfobernsteinsäuremono- und -dialkylester mit 8 bis 18 C-Atomen in der Alkylgruppe und Sulfobernsteinsäuremono-alkylpolyoxyethylester mit 8 bis 18 C-Atomen in der Alkylgruppe und 1 bis 6 Oxyethylgruppen,
• – lineare Alkansulfonate mit 12 bis 18 C-Atomen,
• – lineare Alpha-Olefinsulfonate mit 12 bis 18 C-Atomen,
• – Alpha-Sulfofettsäuremethylester von Fettsäuren mit 12 bis 18 C-Atomen,
• – Alkylsulfate und Alkylpolyglykolethersulfate der Formel R-O(CH₂-CH₂O)_x-SO₃H, in der R eine bevorzugt lineare Alkylgruppe mit 10 bis 18 C-Atomen und x = 0 oder 1 bis 12 ist,
• – Gemische oberflächenaktiver Hydroxysulfonate gemäß DE-A-37 25 030 ,
• – sulfatierte Hydroxyalkylpolyethylen- und/oder Hydroxyalkylenpropylenglykolether gemäß DE-A-37 23 354 ,
• – Sulfonate ungesättigter Fettsäuren mit 12 bis 24 C-Atomen und 1 bis 6 Doppelbindungen gemäß DE-A-39 26 344 ,
• – Ester der Weinsäure und Zitronensäure mit Alkoholen, die Anlagerungsprodukte von etwa 2 bis 15 Molekülen Ethylenoxid und/oder Propylenoxid an Fettalkohole mit 8 bis 22 C-Atomen darstellen.

Suitable anionic surfactants in the kit according to the invention are all anionic surfactants suitable for use on the human body. These are characterized by a water-solubilizing, anionic group such as. Example, a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group having about 10 to 22 carbon atoms. In addition, glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups may be present in the molecule. Examples of suitable anionic surfactants are, in each case in the form of the sodium, potassium and ammonium as well as the mono-, di- and trialkanolammonium salts having 2 or 3 C atoms in the alkanol group,

• - linear fatty acids with 10 to 22 carbon atoms (soaps),
• Ether carboxylic acids of the formula RO- (CH ₂ -CH ₂ O) _x -CH ₂ -COOH, in which R is a linear alkyl group having 10 to 22 C atoms and x = 0 or 1 to 16,
• Acylsarcosides having 10 to 18 C atoms in the acyl group,
• Acyltaurides having 10 to 18 C atoms in the acyl group,
• Acyl isethionates having 10 to 18 C atoms in the acyl group,
• Sulfosuccinic acid mono- and dialkyl esters having 8 to 18 C atoms in the alkyl group and sulfosuccinic acid monoalkyl polyoxyethyl esters having 8 to 18 C atoms in the alkyl group and 1 to 6 oxyethyl groups,
• Linear alkanesulfonates having 12 to 18 C atoms,
• - linear alpha-olefin sulfonates having 12 to 18 C atoms,
• Alpha-sulfofatty acid methyl esters of fatty acids containing 12 to 18 carbon atoms,
• Alkyl sulfates and alkyl polyglycol ether sulfates of the formula RO (CH ₂ -CH ₂ O) _x -SO ₃ H, in which R is a preferably linear alkyl group having 10 to 18 C atoms and x = 0 or 1 to 12,
• Mixtures of surface active hydroxysulfonates according to DE-A-37 25 030 .
• - Sulfated Hydroxyalkylpolyethylen- and / or Hydroxyalkylenpropylenglykolether according to DE-A-37 23 354 .
• - Sulfonates of unsaturated fatty acids having 12 to 24 carbon atoms and 1 to 6 double bonds according to DE-A-39 26 344 .
• - esters of tartaric acid and citric acid with alcohols which are addition products of about 2 to 15 molecules of ethylene oxide and / or propylene oxide to fatty alcohols having 8 to 22 carbon atoms.

Preferred anionic surfactants are alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acids having 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule and in particular salts of saturated and in particular unsaturated C ₈ -C ₂₂ carboxylic acids, such as oleic acid, stearic acid, iso stearic acid and palmitic acid.

Zwitterionic surfactants are those surface-active compounds which carry in the molecule at least one quaternary ammonium group and at least one -COO ^(-) or -SO ₃ ^(-) group. Particularly suitable zwitterionic surfactants are the so-called betaines, such as N-alkyl-N, N-dimethylammonium glycinates, for example cocoalkyldimethylammoniumglycinate, N-acylaminopropyl-N, N-dimethylammoniumglycinates, for example cocoacylaminopropyldimethylammoniumglycinate, and Alkyl-3-carboxymethyl-3-hydroxyethyl-imidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and Kokosacylaminoethylhydroxyethylcarboxymethylglycinat. A preferred zwitterionic surfactant is the fatty acid amide derivative known by the CTFA name Cocamidopropyl Betaine.

Ampholytic surfactants are understood as meaning those surface-active compounds which, apart from a C _8-18 -alkyl or -acyl group in the molecule, contain at least one free amino group and at least one -COOH or -SO ₃ H group and are capable of forming internal salts. Examples of suitable ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids each having about 8 to 18 C Atoms in the alkyl group. Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C _12-18 acylsarcosine.

• – Anlagerungsprodukte von 2 bis 30 Mol Ethylenoxid und/oder 0 bis 5 Mol Propylenoxid an lineare Fettalkohole mit 8 bis 22 C-Atomen, an Fettsäuren mit 12 bis 22 C-Atomen und an Alkylphenole mit 8 bis 15 C-Atomen in der Alkylgruppe,
• – C_12-22-Fettsäuremono- und -diester von Anlagerungsprodukten von 1 bis 30 Mol Ethylenoxid an Glycerin,
• – C_8-22-Alkylmono- und -oligoglycoside und deren ethoxylierte Analoga,
• – Anlagerungsprodukte von Ethylenoxid an Fettsäurealkanolamide.

Nonionic surfactants contain as hydrophilic group z. A polyol group, a polyalkylene glycol ether group or a combination of polyol and polyglycol ether groups. Such compounds are, for example

• Addition products of 2 to 30 moles of ethylene oxide and / or 0 to 5 moles of propylene oxide onto linear fatty alcohols having 8 to 22 carbon atoms, to fatty acids containing 12 to 22 carbon atoms and to alkylphenols having 8 to 15 carbon atoms in the alkyl group,
• C _12-22 fatty acid mono- and diesters of addition products of 1 to 30 moles of ethylene oxide with glycerol,
• C _{8-22 alkyl} mono- and oligoglycosides and their ethoxylated analogs,
• - Addition products of ethylene oxide to fatty acid alkanolamides.

Examples for in the kit according to the invention Usable cationic surfactants are especially quaternary Ammonium compounds. Preference is given to ammonium halides such as alkyltrimethylammonium chlorides, Dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, z. B. Cetyitrimethylammoniumchlorid, stearyltrimethylammonium chloride, Distearyldimethylammonium chloride, lauryldimethylammonium chloride, Lauryldimethylbenzylammonium chloride and tricetylmethylammonium chloride. Further cationic used according to the invention Surfactants are the quaternized protein hydrolysates.

Also suitable in the present invention are cationic silicone oils such as the commercially available products Q2-7224 (manufactured by Dow Corning, a stabilized trimethylsilylamodimethicone), Dow Corning 929 emulsion (containing a hydroxylamino-modified silicone, also referred to as amodimethicones), SM -2059 (manufacturer: General Electric), SLM-55067 (manufacturer: Wacker) and Abil ^® quat 3270 and 3272 (manufacturer: Th Goldschmidt; diquaternary polydimethylsiloxanes, quaternium-80.).

Alkylamidoamines, in particular fatty acid amidoamines, such as the ^{stearylamidopropyldimethylamine} obtainable under the name Tego ^Amid® S 18, are distinguished not only by a good conditioning action but also by their good biodegradability.

Also very good biodegradability are quaternary Esterverbindungen, so-called "esterquats", such as the methyl hydroxyalkyl marketed under the trademark Stepantex ^®.

An example of a suitable cationic surfactant quaternary sugar derivative is the commercially available product Glucquat ^® 100 is, according to CTFA nomenclature a "lauryl methyl Gluceth-10 Hydroxypropyl Dimonium Chloride".

at the compounds used as surfactants with alkyl groups each are uniform substances. However, it is usually preferred in the preparation of these substances of native to go out with vegetable or animal raw materials, so that one Substance mixtures with different, from the respective raw material receives dependent alkyl chain lengths.

at the surfactants, the adducts of ethylene and / or propylene oxide represent fatty alcohols or derivatives of these addition products, can both products with a "normal" homolog distribution as well as those with a narrow homolog distribution become. Under "normal" homolog distribution thereby understood mixtures of homologues, which in the implementation of fatty alcohol and alkylene oxide using alkali metals, Alkali metal hydroxides or alkali metal alcoholates as catalysts receives. Narrow homolog distributions are opposed obtained, for example, when hydrotalcites, alkaline earth metal salts of ether carboxylic acids, alkaline earth metal oxides, hydroxides or -alkoholate be used as catalysts. The usage of products with restricted homolog distribution may be preferred be.

• – nichtionische Polymere wie beispielsweise Vinylpyrrolidon/Vinylacrylat-Copolymere, Polyvinylpyrrolidon und Vinylpyrrolidon/Vinylacetat-Copolymere und Polysiloxane,
• – kationische Polymere wie quaternisierte Celluloseether, Polysiloxane mit quaternären Gruppen, Dimethyldiallylammoniumchlorid-Polymere, Acrylamid-Dimethyldiallylammoniumchlorid-Copolymere, mit Diethylsulfat quaternierte Dimethylaminoethylmethacrylat-Vinylpyrrolidon-Copolymere, Vinylpyrrolidon-Imidazoliniummethochlorid-Copolymere und quaternierter Polyvinylalkohol,
• – zwitterionische und amphotere Polymere wie beispielsweise Acrylamidopropyl-trimethylammoniumchlorid/Acrylat-Copolymere und Octylacrylamid/Methylmethacrylat/tert.-Butylaminoethylmethacrylat/2-Hydroxypropylmethacrylat-Copolymere,
• – anionische Polymere wie beispielsweise Polyacrylsäuren, vernetzte Polyacrylsäuren, Vinylacetat/Crotonsäure-Copolymere, Vinylpyrrolidon/Vinylacrylat-Copolymere, Vinylacetat/Butylmaleat/Isobornylacrylat-Copolymere, Methylvinylether/Maleinsäureanhydrid-Copolymere und Acrylsäure/Ethylacrylat/N-tert.-Butylacrylamid-Terpolymere,
• – Verdickungsmittel wie Agar-Agar, Guar-Gum, Alginate, Xanthan-Gum, Gummi arabicum, Karaya-Gummi, Johannisbrotkernmehl, Leinsamengummen, Dextrane, Cellulose-Derivate, z. B. Methylcellulose, Hydroxyalkylcellulose und Carboxymethylcellulose, Stärke-Fraktionen und Derivate wie Amylose, Amylopektin und Dextrine, Tone wie z. B. Bentonit oder vollsynthetische Hydrokolloide wie z. B. Polyvinylalkohol,
• – Strukturanten wie Glucose und Maleinsäure,
• – haarkonditionierende Verbindungen wie Phospholipide, beispielsweise Sojalecithin, Ei-Lecitin und Kephaline, sowie Silikonöle,
• – Proteinhydrolysate, insbesondere Elastin-, Kollagen-, Keratin-, Milcheiweiß-, Sojaprotein- und Weizenproteinhydrolysate, deren Kondensationsprodukte mit Fettsäuren sowie quaternisierte Proteinhydrolysate,
• – Parfümöle, Dimethylisosorbid und Cyclodextrine,
• – Lösungsvermittler wie Ethanol, Isopropanol, Ethylenglykol, Propylenglykol, Glycerin und Diethylenglykol,
• – Antischuppenwirkstoffe wie Piroctone Olamine und Zink Omadine,
• – weitere Substanzen zur Einstellung des pH-Wertes,
• – Wirkstoffe wie Panthenol, Pantothensäure, Allantoin, Pyrrolidoncarbonsäuren und deren Salze, Pflanzenextrakte und Vitamine,
• – Cholesterin,
• – Lichtschutzmittel,
• – Konsistenzgeber wie Zuckerester, Polyolester oder Polyolalkylether,
• – Fette und Wachse wie Walrat, Bienenwachs, Montanwachs, Paraffine, Fettalkohole und Fettsäureester,
• – Fettsäurealkanolamide,
• – Komplexbildner wie EDTA, NTA und Phosphonsäuren,
• – Quell- und Penetrationsstoffe wie Glycerin, Propylenglykolmonoethylether, Carbonate, Hydrogencarbonate, Guanidine, Harnstoffe sowie primäre, sekundäre und tertiäre Phosphate, Imidazole, Tannine, Pyrrol,
• – Trübungsmittel wie Latex,
• – Perlglanzmittel wie Ethylenglykolmono- und -distearat,
• – Treibmittel wie Propan-Butan-Gemische, N₂O, Dimethylether, CO₂ und Luft sowie
• – Antioxidantien.

Other active ingredients, auxiliaries and additives are, for example

• Nonionic polymers such as vinyl pyrrolidone / vinyl acrylate copolymers, polyvinyl pyrrolidone and vinyl pyrrolidone / vinyl acetate copolymers and polysiloxanes,
• Cationic polymers such as quaternized cellulose ethers, quaternary group polysiloxanes, dimethyldiallylammonium chloride polymers, acrylamide-dimethyldiallylammonium chloride copolymers, diethyl sulfate quaternized dimethylaminoethylmethacrylate-vinylpyrrolidone copolymers, vinylpyrrolidone-imidazolinium methochloride copolymers and quaternized polyvinyl alcohol,
• Zwitterionic and amphoteric polymers such as acrylamidopropyltrimethylammonium chloride / acrylate copolymers and octylacrylamide / methylmethacrylate / tert-butylaminoethylmethacrylate / 2-hydroxypropylmethacrylate copolymers,
• Anionic polymers such as, for example, polyacrylic acids, crosslinked polyacrylic acids, vinyl acetate / crotonic acid copolymers, vinylpyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate / isobornyl acrylate copolymers, methyl vinyl ether / maleic anhydride copolymers and acrylic acid / ethyl acrylate / N-tert-butylacrylamide terpolymers,
• Thickeners such as agar-agar, guar gum, alginates, xanthan gum, gum arabic, karaya gum, locust bean gum, linseed gums, dextrans, cellulose derivatives, e.g. For example, methylcellulose, hydroxyalkylcellulose and carboxymethylcellulose, starch fractions and derivatives such as amylose, amylopectin and dextrins, clays such. As bentonite or fully synthetic hydrocolloids such. For example, polyvinyl alcohol,
• - structurants such as glucose and maleic acid,
• Hair-conditioning compounds such as phospholipids, for example soya lecithin, egg lecithin and cephalins, and silicone oils,
• Protein hydrolysates, in particular elastin, collagen, keratin, milk protein, soy protein and wheat protein hydrolysates, their condensation products with fatty acids and quaternized protein hydrolysates,
• Perfume oils, dimethylisosorbide and cyclodextrins,
• Solubilizers such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol and diethylene glycol,
• Anti-dandruff agents such as Piroctone Olamine and Zinc Omadine,
• - other substances for adjusting the pH,
• - active substances such as panthenol, pantothenic acid, allantoin, pyrrolidonecarboxylic acids and their salts, plant extracts and vitamins,
• - cholesterol,
• - sunscreen,
• Bodying agents such as sugar esters, polyol esters or polyol alkyl ethers,
• Fats and waxes such as spermaceti, beeswax, montan wax, paraffins, fatty alcohols and fatty acid esters,
• Fatty acid alkanolamides,
• - complexing agents such as EDTA, NTA and phosphonic acids,
• - Swelling and penetration substances such as glycerol, propylene glycol monoethyl ether, carbonates, bicarbonates, guanidines, ureas and primary, secondary and tertiary phosphates, imidazoles, tannins, pyrrole,
• Opacifiers such as latex,
• Pearlescing agents such as ethylene glycol mono- and distearate,
• - Propellants such as propane-butane mixtures, N ₂ O, dimethyl ether, CO ₂ and air and
• - antioxidants.

The Components of the cosmetic carrier are used for the production the agent A, the agent (B1), the agent (B2) and optionally in addition to the agent (B3) in customary for this purpose Quantities used; z. B. become emulsifiers in concentrations from 0.5 to 30% by weight and thickener in concentrations of 0.1 to 25 wt .-% based on the particular agent used.

• • mindestens einem Mittel (B1), das in einem kosmetischen Träger mindestens eine reaktive Carbonylverbindung enthält, und
• • mindestens einem Mittel (B2), das in einem kosmetischen Träger mindestens eine C,H-acide Verbindung ausgewählt aus Verbindungen der Formel (CH-1) und/oder Verbindungen der Formel (CH-2) enthält,
  
  worin – R⁶ steht für eine lineare oder cyclische (C₁ bis C₆)-Alkylgruppe, eine (C₂ bis C₆)-Alkenylgruppe, eine gegebenenfalls substituierte Arylgruppe, eine gegebenenfalls substituierte Heteroarylgruppe, eine Aryl-(C₁ bis C₆)-alkylgruppe, eine (C₁ bis C₆)-Hydroxyalkylgruppe, eine (C₂ bis C₆)-Polyhydroxyalkylgruppe, eine (C₁ bis C₆)-Alkoxy-(C₁ bis C₆)-alkylgruppe, eine Gruppe R^IR^IIN-(CH₂)_m-, worin R^I und R^II stehen unabhängig voneinander für ein Wasserstoffatom, eine (C₁ bis C₄)-Alkylgruppe, eine (C₁ bis C₄)-Hydroxyalkylgruppe oder eine Aryl-(C₁ bis C₆)-alkylgruppe, wobei R^I und R^II gemeinsam mit dem Stickstoffatom einen 5-, 6- oder 7-gliedrigen Ring bilden können und m steht für eine Zahl 2, 3, 4, 5 oder 6, – R⁷ steht für eine (C₁ bis C₆)-Alkylgruppe, insbesondere für eine Methylgruppe, – X^– steht für ein physiologisch verträgliches Anion, – der Zyklus der Formel (CH-1) repräsentiert alle Ringstrukturen, die zusätzlich weitere Heteroatome wie Stickstoff, Sauerstoff oder Schwefel enthalten können und ferner ankondensierte Ringstrukturen tragen können, wobei alle diese Ringsstrukturen zusätzliche Substituenten tragen können, – Het steht für einen gegebenenfalls substituierten Heteroaromaten, und – X¹ steht für eine direkte Bindung oder eine Carbonylgruppe,

durch Mischung erhalten wird, zur Färbung der frisch nachgewachsenen Haaransätze von Haaren, die zuvor mit einer oxidativen Färbung behandelt wurden.A third object of the present invention is the use of an agent (B) immediately before use

• At least one agent (B1) which contains at least one reactive carbonyl compound in a cosmetic carrier contains binding, and
• At least one agent (B2) which contains in a cosmetic carrier at least one C, H-acidic compound selected from compounds of the formula (CH-1) and / or compounds of the formula (CH-2),
  
  wherein - R ⁶ represents a linear or cyclic (C ₁ to C ₆ ) alkyl group, a (C ₂ to C ₆ ) alkenyl group, an optionally substituted aryl group, an optionally substituted heteroaryl group, an aryl (C ₁ to C ₆ ) alkyl group, a (C ₁ to C ₆ ) hydroxyalkyl group, a (C ₂ to C ₆ ) polyhydroxyalkyl group, a (C ₁ to C ₆ ) alkoxy (C ₁ to C ₆ ) alkyl group, a group R ^I R ^{II is} N- (CH ₂ ) _m -, in which R ^I and R ^II independently of one another represent a hydrogen atom, a (C ₁ to C ₄ ) -alkyl group, a (C ₁ to C ₄ ) -hydroxyalkyl group or an aryl- (C ₁ to C ₆ ) -alkyl group, wherein R ^I and R ^II together with the nitrogen atom can form a 5-, 6- or 7-membered ring and m is a number 2, 3, 4, 5 or 6, - R ⁷ is a (C ₁ to C ₆ ) -alkyl group, in particular a methyl group, - X ^- is a physiologically acceptable anion, - the cycle of the formula (CH-1) represents all ring structures, the additional lic h may contain further heteroatoms such as nitrogen, oxygen or sulfur and may further carry fused ring structures, all of these ring structures being able to carry additional substituents, - Het is an optionally substituted heteroaromatic, and - X ¹ is a direct bond or a carbonyl group,

obtained by mixing, for coloring the freshly grown hair roots of hair, which were previously treated with an oxidative dye.

• • mindestens einem Mittel (B1), das in einem kosmetischen Träger mindestens eine reaktive Carbonylverbindung enthält, und
• • mindestens einem Mittel (B2), das in einem kosmetischen Träger mindestens eine C,H-acide Verbindung ausgewählt aus Verbindungen der Formel (CH-1) und/oder Verbindungen der Formel (CH-2) enthält,
  
  worin – R⁶ steht für eine lineare oder cyclische (C₁ bis C₆)-Alkylgruppe, eine (C₂ bis C₆)-Alkenylgruppe, eine gegebenenfalls substituierte Arylgruppe, eine gegebenenfalls substituierte Heteroarylgruppe, eine Aryl-(C₁ bis C₆)-alkylgruppe, eine (C₁ bis C₆)-Hydroxyalkylgruppe, eine (C₂ bis C₆)-Polyhydroxyalkylgruppe, eine (C₁ bis C₆)-Alkoxy-(C₁ bis C₆)-alkylgruppe, eine Gruppe R^IR^IIN-(CH₂)_m-, worin R^I und R^II stehen unabhängig voneinander für ein Wasserstoffatom, eine (C₁ bis C₄)-Alkylgruppe, eine (C₁ bis C₄)-Hydroxyalkylgruppe oder eine Aryl-(C₁ bis C₆)-alkylgruppe, wobei R^I und R^II gemeinsam mit dem Stickstoffatom einen 5-, 6- oder 7-gliedrigen Ring bilden können und m steht für eine Zahl 2, 3, 4, 5 oder 6, – R⁷ steht für eine (C₁ bis C₆)-Alkylgruppe, insbesondere für eine Methylgruppe, – X^– steht für ein physiologisch verträgliches Anion, – der Zyklus der Formel (CH-1) repräsentiert alle Ringstrukturen, die zusätzlich weitere Heteroatome wie Stickstoff, Sauerstoff oder Schwefel enthalten können und ferner ankondensierte Ringstrukturen tragen können, wobei alle diese Ringsstrukturen zusätzliche Substituenten tragen können, – Het steht für einen gegebenenfalls substituierten Heteroaromaten, und – X¹ steht für eine direkte Bindung oder eine Carbonylgruppe,

durch Mischung erhalten wird, zur Färbung ergrauter asiatischer Haare.A fourth object of the present invention is to use an agent (B) immediately before use

• At least one agent (B1) containing at least one reactive carbonyl compound in a cosmetic carrier, and
• At least one agent (B2) which contains in a cosmetic carrier at least one C, H-acidic compound selected from compounds of the formula (CH-1) and / or compounds of the formula (CH-2),
  
  wherein - R ⁶ represents a linear or cyclic (C ₁ to C ₆ ) alkyl group, a (C ₂ to C ₆ ) alkenyl group, an optionally substituted aryl group, an optionally substituted heteroaryl group, an aryl (C ₁ to C ₆ ) alkyl group, a (C ₁ to C ₆ ) hydroxyalkyl group, a (C ₂ to C ₆ ) polyhydroxyalkyl group, a (C ₁ to C ₆ ) alkoxy (C ₁ to C ₆ ) alkyl group, a group R ^I R ^{II is} N- (CH ₂ ) _m -, in which R ^I and R ^II independently of one another represent a hydrogen atom, a (C ₁ to C ₄ ) -alkyl group, a (C ₁ to C ₄ ) -hydroxyalkyl group or an aryl- (C ₁ to C ₆ ) -alkyl group, wherein R ^I and R ^II together with the nitrogen atom can form a 5-, 6- or 7-membered ring and m is a number 2, 3, 4, 5 or 6, - R ⁷ is a (C ₁ to C ₆ ) -alkyl group, in particular a methyl group, - X ^- is a physiologically acceptable anion, - the cycle of the formula (CH-1) represents all ring structures, the additional lic h may contain further heteroatoms such as nitrogen, oxygen or sulfur and may further carry fused ring structures, all of these ring structures being able to carry additional substituents, - Het is an optionally substituted heteroaromatic, and - X ¹ is a direct bond or a carbonyl group,

obtained by mixing, for dyeing graying Asian hair.

In terms of the uses of the invention that applies to mutatis mutandis said method according to the invention mutandis.

One Fifth object of the present invention is a multi-part Dyeing kit for carrying out the inventive A method comprising an agent (B1) that is in a cosmetic Carrier 4-hydroxy-2-methoxybenzaldehyde and at least another reactive carbonyl compound selected from 2-chloro-3,4-dihydroxybenzaldehyde, 2-bromo-3,4-dihydroxybenzaldehyde, 3,4-dihydroxy-5-methoxybenzaldehyde, 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde and 2,4-dimethoxybenzaldehyde, and an agent (B2), which in a cosmetic carrier is 1-allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium and / or 2- (cyanomethyl) benzimidazole.

in the Frame of a preferred embodiment of this article of the present invention contains the multi-part dyeing kit additionally an agent (A1) containing at least one dye precursor and an agent (A2) containing at least one oxidizing agent.

Also with respect to this subject of the present invention the statement on the first two items applies mutatis mutandis mutandis.

The The following examples are intended to form the subject of the present invention but without explaining it in any way Way to restrict.

Examples

The The quantities used in the examples are to be understood, if not otherwise indicated, in weight percent.

1 Preparation of the preparations

1.1 Production of funds (B1)

The following agents (B1) containing a reactive carbonyl compound were prepared: component B1a B1b B1c B1d B1e B1f 4-hydroxy-2-methoxybenzaldehyde 6 mmol 3 mmol 1 mmol 2 mmol 4 mmol 1 mmol 3,4-dihydroxy-5-methoxybenzaldehyde 9 mmol 6 mmol 6.5 mmol 6 mmol 6 mmol 5 mmol 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde - 6 mmol 5.5 mmol - - 4 mmol 2,4-dimethoxy-benzaldehyde - - - 2 mmol - - Amaze ^® XT - - - 1.5 - - Cosmedia® Ultragel® ^® 300 - 1.0 - - - - Lorol® ^®, techn. 3.5 2.0 3.0 2.5 2.5 0.5 Eumulgin ^® B2 1.5 - 1.0 - 0.75 1.0 Eumulgin ^® B1 - 1.0 0.5 1.0 - - Hydrenol ^® D 7.0 3.0 8.0 4.5 7.0 5.5 Texapon.RTM ^® NSO 8.0 - - 3.0 8.0 - Plantacare® ^® 1200 4.0 6.0 - - 4.0 - Dehyton ^® K - 5.0 4.0 - - 3.0 Crodafos ^® CES - - 6.0 3.0 - 4.5 Polymer ^® W 37194 0.5 - - 1.0 0.5 - Tween ^® 20 1.0 0.5 - 5.0 1.0 - Solubilisant ^® LRI 2.0 - 1.0 - 2.0 4.0 Cremophor ^® RH 40 - 2.5 5.0 - - 1.5 phenoxyethanol 0.6 0.7 0.5 0.4 0.7 - Na-salicylate 0.4 0.5 0.3 0.2 0.5 - Turpinal® ^® SL 0.4 - - 0.3 0.4 - Perfume 0.2 0.3 0.25 0.4 0.2 0.15 Tartaric acid / monoethanolamine ad pH 3.6 ad pH 4.1 ad pH 3.8 ad pH 3.5 ad pH 3.7 ad pH 3.9 water ad 100 g ad 100 g ad 100 g ad 100 g ad 100 g ad 100g component B1g B1h b1i B1j B1k B1l 4-hydroxy-2-methoxybenzaldehyde 9.5 mmol 10 mmol 3 mmol 2 mmol 2.25 mmol 1.75 mmol 3,4-dihydroxy-5-methoxybenzaldehyde 0.5 mmol - - - 0.25 mmol 0.25 mmol 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde - - 7 mmol - 7.5 mmol - 2,4-dimethoxy-benzaldehyde - - - 8 mmol - 8 mmol Lorol® ^®, techn. 2.0 2.5 2.5 3.0 2.0 1.5 Eumulgin ^® B2 0.5 1.5 1.0 0.75 - - Eumulgin ^® B1 1.0 - 1.5 - 0.75 1.2 Hydrenol ^® D 4.0 8.0 6.5 4.0 4.5 7.0 Protelan ^® MST 35 - 6.0 - 3.5 - 4.0 Plantacare® ^® 2000 6.0 - 4.0 5.0 - - Akypo Soft ^® 45NV 5.0 3.0 - - 4.0 1.0 Lamesoft ^® PO 65 - - 5.5 - 4.5 4.0 Polymer JR 400 1.0 - 0.75 0.5 - - Tween ^® 80 0.5 1.0 1.0 - - 2.5 Solubilisant ^® LRI - 3.0 2.5 4.0 2.0 - Cremophor ^® RH 40 2.5 - 1.5 - 2.0 1.0 phenoxyethanol 0.5 0.6 0.8 0.7 0.55 - Na-salicylate 0.25 0.3 0.6 0.4 0.25 - water glass - 0.3 0.15 - - - Perfume 0.3 0.25 0.15 0.2 0.3 0.10 Tartaric acid / monoethanolamine ad pH 4.2 ad pH 3.4 ad pH 4.3 ad pH 4.0 ad pH 3.9 ad pH 3.3 water ad 100 g ad 100 g ad 100 g ad 100 g ad 100 g ad 100 g component B1m B1n B1O B1p B1Q b1r 4-hydroxy-2-methoxybenzaldehyde 15 mmol - 0.5 mmol - 1 mmol 2 mmol 3,4-dihydroxy-5-methoxybenzaldehyde - 10 mmol 9.5 mmol 15 mmol 12 mmol 10 mmol 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde - - - - 2 mmol - 2,4-dimethoxy-benzaldehyde - - - - - 3 mmol ^Emery® 1780 1.0 2.5 1.5 1.8 0.4 0.9 Eumulgin ^® B2 0.6 - 0.8 0.25 - 0.9 Eumulgin ^® B1 - 0.7 - 0.86 0.5 - Prisorine ^® ISAC 3505 5.6 7.4 6.3 4.9 7.0 5.8 Protelan ^® MST 35 3.0 3.5 - 2.9 - - Cetearyl glucoside 3.5 - 4.0 - 3.8 - Akypo Soft ^® 45NV - 4.2 - - 3.5 4.0 Lamesoft ^® PO 65 - - 4.0 3.5 - 4.3 Abil ^® EM 90 1.5 - 0.5 0.6 - Myritol ^® PC - 1.6 0.8 - 0.4 Antaron ^® V 220 - - 0.9 - 0.7 0.9 Solubilisant ^® LRI 2.5 - 3.0 - 1.5 - Cremophor ^® RH 40 - 2.0 - 2.5 - 3.0 phenoxyethanol 0.7 0.9 1.0 0.8 1.2 0.6 Na-salicylate 0.35 0.5 0.5 0.4 0.6 0.3 water glass - 0.8 - 0.35 - 0.7 Perfume 0.2 0.23 0.18 0.21 0.19 0.25 Tartaric acid / monoethanolamine ad pH 4.5 ad pH 3.5 ad pH 4.1 ad pH 3.6 ad pH 3.9 ad pH 3.7 water ad 100 g ad 100 g ad 100 g ad 100 g ad 100 g ad 100 g component B1s B1T B1U B1v B1W B1x 4-hydroxy-2-methoxybenzaldehyde 1 mmol 2 mmol 3.8 mmol 2.5 mmol 3 mmol 2 mmol 3,4-dihydroxy-5-methoxybenzaldehyde 9 mmol 8 mmol 11.2 mmol 12.5 mmol 9 mmol 10 mmol 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde 2 mmol - - - - - 2,4-dimethoxy-benzaldehyde - 2 mmol - - - - Eutanol G 2.5 1.0 0.7 0.9 2.0 1.8 Eumulgin ^® B2 0.5 0.9 0.75 0.4 1.0 0.7 Elfacos ^® ST 9 - 5.0 4.2 - 6.8 2.2 Hydrenol ^® D 5.5 - 3.5 6.0 - 3.5 Crosilk ^® Liquid 1.6 - 1.1 0.5 0.8 - Plantacare® ^® 2000 - 4.0 3.5 1.0 - 2.6 Crodasinic ^® C 3.7 1.5 - 2.5 - 3.0 Lame form TGI ^® 4.3 - 1.5 2.0 - - Dow ^Corning® 245 Fluid - 1.8 1.1 - 2.0 - Tween ^® 80 4.5 1.4 - 3.5 2.2 3.6 Incroquat ^® 26 1.5 - 1.1 1.2 - 0.4 Elfacos ^® ST 37 - 1.8 1.2 - - 0.7 phenoxyethanol 0.8 0.6 - 0.5 1.1 1.0 Na-salicylate 0.4 0.3 - 0.25 0.5 0.6 water glass - 0.5 - - 0.8 - Perfume 0.2 0.23 0.18 0.21 0.19 0.25 Tartaric acid / monoethanolamine ad pH 4.0 ad pH 3.8 ad pH 4.3 ad pH 3.2 ad pH 3.4 ad pH 4.4 water ad 100 g ad 100 g ad 100 g ad 100 g ad 100 g ad 100 g component B1y b1z B1aa B1ab B1ac B1ad 4-hydroxy-2-methoxybenzaldehyde - - - - 1 mmol 1 mmol 2-chloro-3,4-dihydroxybenzaldehyde 10 - 15 - 9 mmol 9 mmol 2-bromo-3,4-dihydroxybenzaldehyde - 10 - 15 - - 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde - - - - 2 mmol - 2,4-dimethoxy-benzaldehyde - - - - - 2 mmol Finsolv ^® TN 1.0 0.7 1.5 1.1 2.0 1.8 Eumulgin ^® B2 0.6 - 1.0 0.75 1.0 0.7 Eumulgin ^® B1 - 1.0 1.5 - - 1.0 Hydrenol ^® D 5.8 6.2 6.5 4.0 5.0 4.5 Adinol ^® CT 30 0.9 - 1.2 0.4 1.9 - panthenol 0.3 1.4 0.6 1.7 - 2.0 Crodasinic ^® L 4.5 - 3.0 1.5 - - Lamesoft ^® PO 65 - 4.2 - 1.8 2.9 - Polymer JR 400 - 0.9 - 1.1 - 0.7 Crillet ^® 1 2.0 1.5 3.2 4.5 2.5 4.2 Crill ^® 1 0.4 - - - 0.38 - Crodamol ^® BS - - 1.3 1.6 - - Crodamol EO ^® - 0.7 0.9 - - 1.4 Hydrolactin ^® 2500 - - 1.8 - 1.1 0.8 almond oil 0.65 - - 0.25 - 0.47 phenoxyethanol 0.8 0.9 1.2 - 0.7 1.0 Na-salicylate 0.4 0.4 0.6 - 0.5 0.5 water glass - 0.3 - 0.85 - - Perfume 0.1 0.2 0.3 0.15 0.25 0.35 Tartaric acid / monoethanolamine ad pH 3.3 ad pH 4.5 ad pH 4.3 ad pH 4.0 ad pH 3.9 ad pH 3.9 water ad 100 g ad 100 g ad 100 g ad 100 g ad 100 g ad 100 g component B1ae B1af B1ag B1ah B1ai B1aj 4-hydroxy-2-methoxybenzaldehyde 3.8 mmol 2 mm 1.75 mmol 2.25 mmol 1 mmol 2 mmol 2-chloro-3,4-dihydroxybenzaldehyde 11.2 mmol - 0.25 mmol - 5 mmol - 2-bromo-3,4-dihydroxybenzaldehyde - 10 mm - 0.25 mmol - 6 mmol 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde - - - 7.5 mmol 4 mmol - 2,4-dimethoxy-benzaldehyde - - 8 mmol - - 2 mmol Lorol® ^®, techn. 1.0 - - - - 1.2 Eumulgin ^® B2 0.5 - - - - 0.8 Carbomer ^® 134 0.6 1.3 - 0.5 - - Antil ^® 141 - - 1.4 0.8 1.6 0.8 Hudrenol ^® D 5.6 - - - - 6.3 Protelan ^® MST 35 3.0 3.5 4.1 - - - TEGO ^® Betaine HS 3.5 - - - 4.0 3.8 Amisoft ^® CT12 - 3.8 - 4.2 - 4.0 Lamesoft ^® PO 65 - - 3.8 3.1 4.3 - AquaCat® ^® CG518 3.0 2.4 - 2.8 - 1.9 Softcat ^® SX 2.3 1.5 - - 2.6 1.9 Croquat ^® M - 0.5 0.3 0.7 - - Prodew ^® 500 - - - 0.5 1.1 0.9 Cranberry oil 0.4 - - - 0.5 07 Rewoderm ^® LI 63 1.2 1.0 0.8 - - - phenoxyethanol 0.6 - 1.2 1.0 - 0.8 Na-salicylate 0.3 - 0.6 0.5 - 0.4 water glass 0.5 0.8 - 0.6 - 0.8 Perfume 0.1 0.2 0.3 0.15 0.25 0.35 Tartaric acid / monoethanolamine ad pH 4.2 ad ph 3,4 ad pH 4.3 ad pH 4.0 ad pH 3.9 ad pH 3.7 water ad 100g ad 100 g ad 100 g ad 100 g ad 100 g ad 100 g component B1ak B1al B1am B1an B1ao B1ap 4-hydroxy-2-methoxybenzaldehyde 6 mmol 3 mmol 1 mmol 1.5 mmol 4 mmol 3 mmol 2-chloro-3,4-dihydroxybenzaldehyde - 6 mmol 6.5 mmol - 6 mmol 2-bromo-3,4-dihydroxybenzaldehyde 9 mmol - - 6 mmol 7 mmol 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde - 6 mmol - 5.5 mmol 2,4-dimethoxy-benzaldehyde - - 5.5 mmol - - - Lorol® ^®, techn. 0.8 1.0 0.7 0.5 0.9 1.1 Eumulgin ^® B2 0.5 - 0.6 - 0.4 - Eumulgin ^® B1 - 0.4 - 0.7 - 0.8 Hydrenol ^® D 5.0 6.2 5.8 4.5 6.0 5.7 Incroquat ^® SDQ 25 3.2 4.1 3.8 - - - Plantacare® ^® 2000 3.6 - - - 4.1 3.9 Crodafos ^® G26a - 3.8 - 4.2 - 3.1 Lamesoft ^® PO 65 - - 4.0 3.4 3.9 - Crotein ^® MCAA 0.5 0.8 - - 1.5 - Crillet ^® 2 - - 0.7 0.9 - 1.9 Solubilisant ^® LRI 3.0 - - 3.6 - 4.2 Cremophor ^® RH 40 - 3.5 2.8 - 2.4 - Abil ^® B 8863 0.8 1.2 0.6 - 1.0 - phenoxyethanol - - 0.9 0.9 1.3 0.7 Na-salicylate - - 0.5 0.4 0.6 0.4 water glass - - - 1.1 - 0.8 Perfume 0.1 0.2 0.3 0.15 0.25 0.35 Tartaric acid / monoethanolamine ad pH 4.2 ad pH 3.4 ad pH 4.3 ad pH 4.0 ad pH 3.9 ad pH 3.9 water ad 100 g ad 100 g ad 100 g ad 100 g ad 100 g ad 100 g

1.1.1 Preparation of the cream formulations B1a to B1ae and B1aj to B1ap

Lorol ^®, Eumulgin ^® B1 or B2 Eumulgin ^{®, ®} Finsolv TN, Elfacos ST9 ^®, Emery ^® 1780 Prisorine ISAC ^® 3505 and / or Hydrenol D ^® were melted together at 80 ° C. In this melt required for the individual formulations, proportions of the components Texapon ^® NSO, Plantacare ^® 1200 were Plantacare ^® 2000, Dehyton ^® K, Cordafos ^® CES, Protelan ^® MST 35, Akypo Soft ^® 45NV, cetearyl glucoside, Crodasinic ^® C, Cordasinic ^® L, Lameform ^® TGI, Tego betaine ^® BS, Amisoft CT12 ^{®, ®} AquaCat CG518, Incroquat ^® SDQ25, Crodafos ^® G26a and / or Lamesoft ^® PO incorporated 65th To this mixture, the indicated proportions of the carbonyl compounds 4-hydroxy-2-methoxybenzaldehyde, 3,4,5-trihydroxybenzaldehyde, 3,4-dihydroxy-5-methoxybenzaldehyde, 2,3-dihydro-1,5-dimethyl-3-oxo 2-phenyl-1H-pyrazole-4-carboxaldehyde, 2,4-dimethoxy-benzaldehyde, 2-chloro-3,4-dihydroxybenzaldehyde and / or 2-bromo-3,4-dihydroxybenzaldehyde dissolved in 80 to 90 ° C hot water, added with stirring. While the mixture slowly cooled to room temperature with stirring, the remaining recipe ingredients were added. The swelling agent Carbomer ^® 134, Antil ^® 141, Amaze XT ^® and / or Cosmedia Ultragel ^® 300 were pre-swollen in water and added depending on the particular formulation. Subsequently, the pH stated for the respective formulation was adjusted by addition of tartaric acid or monoethanolamine. Finally, it was made up to 100 g with warm water.

1.1.2 Preparation of gel formulations B1af to B1ai

4-hydroxy-2-methoxybenzaldehyde, 3,4,5-trihydroxybenzaldehyde, 3,4-dihydroxy-5-methoxybenzaldehyde, 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole 4-carboxaldehyde, 2,4-dimethoxy-benzaldehyde, 2-chloro-3,4-dihydroxybenzaldehyde and / or 2-bromo-3,4-dihydroxybenzaldehyde were dissolved in 70 g of 80 to 90 ° C hot water with stirring, then were necessary for the individual formulations, proportions of the components Protelan ^® MST 35, Lamesoft ^® PO 65, Tego betaine ^® BS, Amisoft® and / or AquaCat CG518 ^® added and filled up with warm water to 100 g. During the cooling, the previously pre-swollen agent Carbomer ^® 134 and / or Antil ^® 141 was added with continued stirring. The source process was awaited. Subsequently, the remaining recipe ingredients were added. Finally, by adding phosphoric acid or monoethanolamine, the pH stated for the particular formulation was established and made up to 100 g with cold water.

1.2 Preparation of the means (B2)

The following preparations (B2) containing a C, H-acidic compound were prepared: component B2a b2b b2c B2d B2e B2f b2g 1-allyl-1,2-dihydro-3,4,6-trimethyl-2-oxo-pyrimidiniumbromid 15 mmol 9 mmol 12 mmol - 10 mmol - 7 mmol 2- (cyanomethyl) benzimidazole - 6 mmol - - - - 3 mmol 1,2-dihydro-1,3,4,6-tetramethyl-2-oxo-pyrimidiniumhydrogensulfonat - - - 12 mmol - 10 mmol - Synthalen ^® K - - - - - 1.25 - Carbopol Ultrez ^® 10 - - - - 1.35 - 2.0 Lorol® ^®, techn. 2.0 2.5 1.0 1.5 - - - Eumulgin ^® B2 1.0 0.5 - 0.75 - - - Eumulgin ^® B1 - - 1.5 - - - - Hydrenol ^® D 7.0 7.5 3.5 4.0 - - - Texapon.RTM ^® NSO 4.0 - - 3.5 1.5 - 2.0 Plantacare® ^® 2000 - 6.0 6.0 - 1.0 1.5 - Dehyton ^® K 5.0 3.0 - - - - 1.5 Crodafos ^® CES - - 4.0 3.5 - 2.0 - Perfume 0.25 0.2 0.4 0.3 - - 0.35 phenoxyethanol 0.9 1.0 0.7 0.6 0.8 1.2 0.7 sodium salicylate 0.4 0.5 0.4 0.3 0.4 0.6 0.3 Tartaric acid / monoethanolamine ad pH 1.1 ad pH 1.2 ad pH 1.3 ad pH 1.5 ad pH 1.8 ad pH 1.7 ad pH 1.9 water ad 100 g ad 100g ad 100 g ad 100 g ad 100 g ad 100 g ad 100 g component B2h b2i B2j B2k B2L B2m 1-allyl-1,2-dihydro-3,4,6-trimethyl-2-oxo-pyrimidinium bromide 6 mmol 4 mmol 11 mmol 12 mmol 9 mmol 10 mmol 2- (cyanomethyl) benzimidazole 4 mmol 6 mmol 4 mmol 3 mmol 3 mmol 2 mmol Amaze ^® XT 1.3 - 0.7 - - - Carbopol ^® 675 - 1.6 0.9 1.2 - - Lorol® ^®, techn. - - - - 1.0 0.7 Eumulgin ^® B1 - - - - 0.6 1.0 Hudrenol ^® D - - - - 5.0 6.0 Texapon.RTM ^® NSO 3.5 - 4.0 3.0 - - Plantacare® ^® 2000 - 3.5 3.0 - - 4.0 Dehyton ^® K 3.0 - - - 3.5 4.0 Crodafos ^® CES - 3.0 - 3.5 4.0 - Perfume 0.10 0.20 0.30 0.15 0.25 0.35 sodium benzoate 0.5 0.3 0.6 0.8 0.7 1.0 Tartaric acid / monoethanolamine ad pH 2.0 ad pH 1.8 ad pH 1.5 ad pH 2.2 ad pH 1.0 ad pH 2.1 water ad 100 g ad 100 g ad 100 g ad 100 g ad 100 g ad 100 g

1.2.1 Preparation of the cream formulations B2a to B2d, B2l and B2m

Lorol ^®, Eumulgin ^® B1 and B2 Eumulgin ^® and / or Hydrenol D ^® were melted together at 80 ° C. Into this melt, the necessary for the individual formulations amounts of the components Texapon ^® NSO, Plantacare ^® 2000, Dehyton ^® K and / or Crodafos ^® CES were incorporated.

1-allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidiniumbromid, 1,2-dihydro-1,3,4,6-tetramethyl-2-oxo-pyrimidinium hydrogensulfonat and / or 2- (cyanomethyl) benzimidazole dissolved in 80 to 90 ° C hot water, were stirred added. After cooling, the remaining Added recipe ingredients. Subsequently was by addition of tartaric acid or monoethanolamine adjusted for the particular formulation pH value. Finally, it was filled with warm water to 100 g.

1.2.2 Preparation of gel formulations B2e to B2k

1-Alyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide, 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium hydrogen sulfonate and / or 2- (Cyanomethyl) benzimidazole were dissolved in 70 g of 80 to 90 ° C hot water with stirring, then the necessary proportions of the components Texapon ^® NSO, Dehyton ^® K, Plantacare ^® 2000 and / or Crodafos ^® CES were added for the individual formulations and with warm water to 95 g. Then Synthalen® ^® K and / or Carbopol Ultrez ^® 10 were slowly added while continuing to stir. The source process was awaited. Finally, the remaining formulation ingredients were added and adjusted by the addition of tartaric acid or monoethanolamine specified for the respective formulation pH. With warm water was made up to 100 g.

1.3 Production of funds (B3)

The following compositions (B3) containing an alkalizing agent were prepared: composition Medium B3a 20 wt .-% monoethanolamine in water Medium B3b Concentrated ammonia solution in water Medium B3c 10% by weight of sodium hydroxide solution in water Medium B3d 10 wt .-% arginine solution in water Medium B3e 10% by weight potassium hydroxide solution in water

1.4 Production of the means A1

The following coloring cream (A1) was prepared: component Recipe A1 Cetearyl Alcohol 13.7 Ceteareth-20 3.4 p-Toluylenediamine 3.2 ammonium hydroxide 3.2 glycol distearate 2.3 octyldodecanol 2.3 glyceryl stearate 2.0 sodium laureth sulfate 1.3 glycerin 0.8 resorcinol 0.8 potassium hydroxide 0.7 sodium cetearyl sulfate 0.7 2,4-Diaminophenoxyethanol hydrochloride 0.6 4-chlororesorcinol 0.6 oleic acid 0.4 sodium 0.4 Perfume 0.4 silica 0.25 Tetrasodium EDTA 0.2 Carbomer 0.2 potassium stearate 0.2 m-aminophenol 0.2 Polyquaternium-39 0.1 ascorbic acid 0.1 sodium sulphate 0.1 Linoleamidopropyl PG-Dimonium Chloride Phosphate 0.03 benzyl 0.02 Moringa Pterygosperma Seed Extract 0.005 citric acid 0,002 Titanium dioxide 0.5 water ad 100

1.5 Production of the means A2

The following oxidizer preparation (A2) was prepared: component Recipe (A2) disodiumpyrophosphate 0.3 Disodium EDTA 0.15 Emulgade® ^® F 2.2 Phosphoric acid (85%) 0.04 Hydrogen peroxide (50%) 18 water ad 100

1.6 List of used commercial products

The commercial products used in the examples are defined as follows: Abil ^® B 8843 polyether-modified polysiloxane (INCI name: PEG-14 Dimethicone) (Evonik Degussa) Abil ^® EM 90 modified polyether polysiloxane (INCI name: Cetyl PEG / PPG) 10/1 Dimethicone) (Evonik Deguss) Adinol ^® CT 30 INCI name: Aqua (and) Sodium Methyl Cocoyl Taurate) (Croda) Akypo Soft 45 NV ^® Lauryl Alcohol 4.5 EO Acetic Acid Sodium Salt (at least 21%) Active substance content; INCI name: sodium laureth-6 carboxylates) (Chem-Y) Amaze ^® XT Dehydrated xanthan gum (INCI name: dehydroxanthan gum) (National Starch) Amisoft ^® CT12 Triethanolamine N-cocoyl-L-glutamate (about 28.32% active ingredient content; INCI name: TEA-cocoyl glutamate) (Ajinomoto) Antaron ^® V 220 INCI name: VP / eicosene copolymer (ISP) Antil ^® 141 Polyoxyethylene propylene glycol dioleate (about 40% active ingredient content; Name: Propylene Glycol, PEG-55 Propylene Glycol Oleate) (Goldschmidt) AquaCat® ^® CG518 Guar derivative (about 9.5 to 10.5% solids; INCI name: Guar Hydroxypropyltrimonium chlorides) (Hercules) Carbomer ^® 134 INCI name: Carbomer (Evonik Goldschmidt) Carbopol ^® 675 Polyacrylic acid powder (INCI name: Carbomer) (Lubrizol) Carbopol ^® Ultrez 10 Polyacrylate (INCI name: carbomer) (Lubrizol) Cosmedia® Ultragel® ^® 300 2- (trimethylammonio) ethylmethacrylate chloride homopolymer (at least 92% by weight) Solid; INCI name: Polyquaternium-37) (Cognis) Cremophor ^® RH40 hydrogenated castor oil with approx. 40-45 EO units (INCI name: PEG-40 Hydrogenated Castor Oil) (BASF) Crill ^® 1 INCI name: Sorbitan Laurate (Croda) Crillet ^® 1 INCI name: Polysorbate 20 (Croda) Crillet ^® 2 INCI name: Polysorbate 40 (Croda) Crodafos ^® CES INCI name: Cetearyl Alcohol, Dicetyl Phosphate, Ceteth-10 Phosphates (Croda) Crodafos ^® G26a ethoxylated glyceryl phosphate (INCI name: Glycereth-26 Phosphates) (Croda) Crodamol ^® BS distilled stearic acid butyl ester (INCI name: butyl stearate) (Croda) Crodamol EO ^® INCI name: Ethyl Oleate (Croda) Crodasinic ^® C INCI name: Cocoyl Sarcosine (Croda) Crodasinic ^® L INCI name: Lauroyl Sarcosine (Croda) Croquat ^® M about 40% active ingredient content; INCI name: Aqua (and) Lauryldimonium Hydroxypropyl Hydrolyzed Collagen (Croda) Crosilk ^® Liquid about 27 to 31% solids; (INCI name: Aqua, Silk Amino Acids) (Croda) Crotein ^® MCAA about 15% active ingredient content; (INCI name: Aqua (and) Collagen Amino Acids) (Croda) Dehyton ^® K N, N-dimethyl-N- (C8-18-cocoamidopropyl) ammonium aceto-betaine (about 30%) Active substance; INCI name: Aqua (Water), Cocamidopropyl Betaine) (Cognis) Dow ^Corning® 245 Fluid Dimethylsiloxane pentamer (95% purity, INCI name: Cyclomethicones) (Dow Corning) Elfacos ^® ST 9 100% active ingredient content; INCI name: PEG-45 / dodecyl glycol Copolymer) (Akzo Nobel) Elfacos ^® ST 37 INCI name: PEG-22 / dodecyl glycol copolymer (Akzo) ^Emery® 1780 INCI name: Lanolin Alcohol (Cognis) Emulgade® ^® F Mixture of cetylstearyl alcohol, castor oil with approx. 40 EO units and the sodium salt of cetyl stearyl sulfate (INCI name: Cetearyl Alcohol, PEG-40 Castor Oil, Sodium Cetearyl Sulfate) (Cognis) Eumulgin ^® B1 Cetylstearyl alcohol with approx. 12 EO units (INCI name: Ceteareth- 12) (Cognis) Eumulgin ^® B2 Cetylstearyl alcohol with approx. 20 EO units (INCI name: Ceteareth- 20) (Cognis) Finsolv ^® TN C _12-15 -alkyl esters of benzoic acid (INCI name: C12-15 alkyl Benzoates) (Innospec) Hydrenol ^® D C _16-18 fatty alcohol (INCI name: Cetearyl alcohol) (Cognis) Hydrolactin ^® 2500 hydrolyzed milk protein (about 77-90% protein, INCI name: Hydrolyzed Milk Protein) (Croda) Incroquat ^® 26 Minkamidopropyldimethylhydroxyethylammonium chloride (INCI name: Quaternium-26) (Croda) Incroquat ^® SDQ 25 about 25% active ingredient content; (INCI name: Stearalkonium Chloride) (Croda) Lame form TGI ^® about 100% active ingredient content; INCI name: polyglyceryl-3 Diisostearate (Cognis) Lame Soft ^® PO65 Alkylpolyglucoside oleic acid monoglyceride Mixture (about 65-70% solids; INCI name: Coco-Glucoside, Glyceryl Oleate, Aqua (Water)) (Cognis) Lorol® ^®, tech. C _12-18 fatty alcohol (INCI name: Coconut alcohol) (Cognis) Myritol ^® PC INCI name: Propylene Glycol Dicaprylate / Dicaprate (Cognis) Plantacare® ^® 1200 C _12-16 -fatty alcohol-1,4-glucoside (about 50-53% active ingredient content; Name: Lauryl Glucoside, Aqua (Water)) (Cognis) Plantacare® ^® 2000 C _8-16 alkylglucoside (about 51-55% active ingredient content in water; Name: Decyl Glucoside, Aqua (Water)) (Cognis) Polymer ^JR® 400 quaternized hydroxyethyl cellulose (INCI name: Polyquaternium-10) (Amerchol) Polymer ^® W 37194 about 20% by weight of active substance content in water; INCI name: Acrylamidopropyltrimonium Chloride / Acrylates Copolymer (Stockhausen) Prisorine ^® ISAC 3505 Isostearic acid (INCI name: Isostearic Acid) (Croda) Prodew ^® 500 Raw material mixture; (INCI names: 15.0 wt% sodium PCA, 12.0% by weight of sodium lactate, 8.0% by weight of arginine, 5.2% by weight of aspartic acid Acid, 4.3 wt% PCA, 1.3 wt% Glycine, 1.2 wt% Alanine, 0.8 wt% Serine, 0.6% by weight of valine, 0.4% by weight of proline, 0.4% by weight of threonine, 0.4% by weight of isoleucines, 0.2% by weight of histidine, 0.2% by weight of phenylalanine, Rest Water) (Ajinomoto) Protelan ^® MST 35 Mixture of sodium N-myristoyl sarcosinate and sodium N-methyl-N- cocoyltaurate (40% by weight of active substance, Zschimmer & Schwartz) Rewoderm ^® LI 63 ethoxylated coconut mono / diglycerides (about 100% active ingredient; Name: PEG-30 glyceryl cociate) (Evonik Degussa) Softcat ^® SX quaternized hydroxyethylcellulose (about 91% purity, INCI name: Polyquaternium-67) (Dow) Solubilisant ^® LRI about 9.5 to 10.5 wt .-% water content; INCI name: PPG-26-buteth- 26, PEG-40 Hydrogenated Castor Oil (Sensient Cosmetic Technologies) Synthalen ^® K Polyacrylic acid (about 89% active ingredient content, INCI name: carbomer) (3 V Sigma) Tego betaine HS (about 29-32% active ingredient in 63-67% water with 4.5-5.3% sodium chloride; INCI name: Cocamidopropyl Betaine, Glyceryl Laurate) (Evonik Degussa) Texapon.RTM ^® NSO Lauryl ether sulfate, sodium salt (about 27.5% active ingredient; INCI name: Sodium Laureth Sulfate) (Cognis) Turpinal® ^® SL 1-hydroxyethane-1,1-diphosphonic acid (about 58-61% active ingredient content; INCI name: Etidronic Acid, Aqua (Water) (Solutia) Tween ^® 20 ethoxylated sorbitan monolaurate (about 2.5-3% by weight water content; Name: Polysorbate-20) (Croda) Tween ^® 80 Sorbitan monooleate with about 20 EO units (maximum 3% by weight of water; Name: Polysorbate-80) (Croda)

2 coloration

2.1 Oxidative staining

immediate before use, 60 ml of the stain (A1) with 60 ml of the oxidizing agent preparation (B1) and mixed on the applied to hair to be dyed. After a contact time of For 30 minutes at 32 ° C, the mixture became thorough with water from the hair, this with a commercial shampoo cleaned again and then with a hairdryer dried.

2.2 Post-treatment

to Preparation of the ready-mix dye mixture were the agents (B1) and (B2) in a weight ratio 1: 1 mixed. Immediately afterwards so much of the preparation (B3) was added until specified in the following table pH of the mixture was reached.

The ready-to-use colorant obtained was applied in a ratio of 2 g of color mixture to 1 g of hair (Kerling natural white and / or grayish Asian hair). After a contact time of 30 minutes at 32 ° C, the strands were rinsed with lukewarm water and then dried in a warm air stream (30 to 40 ° C). The stains were visually assessed under a daylight lamp. Nuances no. combined formulation Precipitation pH value Color (on Kerling natural white and gray Asian hair) Nuance 1 B2a + B1a + B3a 7.5 medium brown Nuance 2 B2a + B1b + B3c 8.2 dark brown Nuance 3 B2c + B1c + B3e 9.0 black-brown Nuance 4 B2d + B1c + B3b 7.9 dark brown Nuance 5 B2e + B1d + B3d 8.5 black-brown Nuance 6 B2f + B1d + B3a 9.2 dark brown Nuance 7 B2g + B1d + B3c 7.4 medium brown Nuance 8 B2g + B1e + B3e 8.8 medium brown Nuance 9 B2h + B1e + B3b 7.7 tan Nuance 10 B2e + B1f + B3d 8.0 black-brown Nuance 11 B2f + B1f + B3a 8.4 medium brown Nuance 12 B2g + B1f + B3c 7.8 tan Nuance 13 B2e + B1g + B3e 7.6 dark wine red Nuance 14 B2f + B1g + B3b 8.1 Dark red Nuance 15 B2i + B1g + B3d 7.8 Red orange Nuance 16 B2e + B1h + B3a 8.6 Dark red Nuance 17 B2f + B1h + B3c 9.0 red Nuance 18 B2h + B1h + B3e 7.5 Red orange Nuance 19 B2e + B1i + B3b 8.3 Orange red Nuance 20 B2f + B11 + B3d 7.9 copper Nuance 21 B2g + B11 + B3a 7.4 copper Orange Nuance 22 B2e + B1j + B3c 8.0 Orange red Nuance 23 B2f + B1j + B3e 8.7 copper Nuance 24 B2g + B1j + B3b 7.8 copper Orange Nuance 25 B2e + B1k + B3d 8.2 red copper Nuance 26 B2f + B1k + B3a 7.7 orange copper Nuance 27 B2e + B1l + B3c 8.3 red copper Nuance 28 B2f + B1l + B3e 7.0 orange copper Nuance 29 B2e + B1m + B3b 8.1 Dark red Nuance 30 B2h + B1m + B3d 9.0 Red orange Nuance 31 B2a + B1m + B2a 8.4 dark wine red Nuance 32 B2e + B1n + B3c 8.0 Black Blue Nuance 33 B2f + B1n + B3e 7.5 dark Blue Nuance 34 B2e + B1o + B3d 8.2 violet Nuance 35 B2f + B10 + B3d 7.8 dark purple Nuance 36 B2a + B1p + B3a 8.5 Black Blue Nuance 37 B2e + B1p + B3c 7.6 Black Blue Nuance 38 B2a + B1q + B3e 8.3 black Nuance 39 B2a + B1r + B3b 7.4 black Nuance 40 B2c + to + B3d 8.6 black Nuance 41 B2c + B1t + B3a 7.7 black Nuance 42 B2j + B1u + B3c 8.1 black Nuance 43 B2j + B1v + B3e 7.9 black Nuance 44 B2k + B1u + B3b 8.4 black Nuance 45 B2k + B1v + B3d 8.2 black Nuance 46 B2l + B1w + B3a 9.0 black Nuance 47 B2l + B1x + B3c 7.8 black Nuance 48 B2m + B1w + B3e 8.8 black Nuance 49 B2m + B1x + B3b 8.5 black Nuance 50 B2e + B1y + B3d 7.6 Black Blue Nuance 51 B2f + B1y + B3a 8.3 Black Blue Nuance 52 B2e + B1z + B3c 7.4 Black Blue Nuance 53 B2f + B1z + B3e 8.6 Black Blue Nuance 54 B2a + B1aa + B3b 7.7 black Nuance 55 B2e + B1aa + B3d 8.1 black Nuance 56 B2a + B1 from + B3a 7.9 black Nuance 57 B2e + B1 from + B3c 8.4 black Nuance 58 B2c + B1ac + B3e 8.2 black Nuance 59 B2d + B1ac + B3b 9.0 black Nuance 60 B2c + B1ad + B3d 7.0 black Nuance 61 B2d + B1ad + B3a 8.1 black Nuance 62 B2j + B1ae + B3c 9.0 black Nuance 63 B2k + B1ae + B3e 8.4 black Nuance 64 B2k + B1af + B3b 8.0 black Nuance 65 B2l + B1af + B3d 7.5 black Nuance 66 B2e + B1ag + B3a 8.2 red copper Nuance 67 B2f + B1ag + B3c 7.8 orange copper Nuance 68 B2e + B1ah + B3e 7.8 red copper Nuance 69 B2f + B1ah + B3b 7.6 orange copper Nuance 70 B2d + B1aj + B3d 8.1 black-brown Nuance 71 B2e + B1aj + B3a 7.8 dark brown Nuance 72 B2f + B1aj + B3c 8.6 medium brown Nuance 73 B2e + B1ai + B3e 9.0 black-brown Nuance 74 B2f + B1ai + B3b 7.5 medium brown Nuance 75 B2g + B1ai + B3d 8.3 tan Nuance 76 B2a + B1ak + B3a 8.4 medium brown Nuance 77 B2b + B1al + B3c 8.0 dark brown Nuance 78 B2c + B1am + B3e 7.5 black-brown Nuance 79 B2d + B1am + B3b 8.2 dark brown Nuance 80 B2c + B1an + B3d 7.8 black-brown Nuance 81 B2d + B1an + B3a 8.5 dark brown Nuance 82 B2g + B1ao + B3c 7.6 medium brown Nuance 83 B2h + B1ao + B3e 8.3 tan Nuance 84 B2g + B1ap + B3b 7.4 medium brown Nuance 85 B2h + B1ap + B3d 8.6 tan

With the dye precursors according to the invention were intense and brilliant colorings on European Hair achieved.

Also the more difficult to color white European and especially white Asian hair has been intensely colored, so that get a good gray coverage with these combinations has been.

Furthermore was found that by the aftertreatment with the inventive Means (B) the freshly grown hair roots without the disadvantages of frequent oxidative staining could be dyed intensively and opaque.

QUOTES INCLUDE IN THE DESCRIPTION

This list The documents listed by the applicant have been automated generated and is solely for better information recorded by the reader. The list is not part of the German Patent or utility model application. The DPMA takes over no liability for any errors or omissions.

Cited patent literature

• - EP 998908 A2 [0118]
• - DE 3725030 A [0266]
• - DE 3723354 A [0266]
• - DE 3926344 A [0266]

Claims (15)

Process for the permanent dyeing of gray hair, characterized in that - in a first step the entire hair is treated with an oxidative dye (A) and - the subsequently regrown gray hair roots are treated in one or more further steps with an agent (B), that just prior to use, comprises at least one agent (B1) which contains at least one reactive carbonyl compound in a cosmetic carrier, and at least one agent (B2) which, in a cosmetic carrier, comprises at least one C, H-acidic compound selected from compounds of the formula (CH-1) and / or compounds of the formula (CH-2),

wherein - R ⁶ represents a linear or cyclic (C ₁ to C ₆ ) alkyl group, a (C ₂ to C ₆ ) alkenyl group, an optionally substituted aryl group, an optionally substituted heteroaryl group, an aryl (C ₁ to C ₆ ) alkyl group, a (C ₁ to C ₆ ) hydroxyalkyl group, a (C ₂ to C ₆ ) polyhydroxyalkyl group, a (C ₁ to C ₆ ) alkoxy (C ₁ to C ₆ ) alkyl group, a group R ^I R ^{II is} N- (CH ₂ ) _m -, in which R ^I and R ^II independently of one another represent a hydrogen atom, a (C ₁ to C ₄ ) -alkyl group, a (C ₁ to C ₄ ) -hydroxyalkyl group or an aryl- (C ₁ to C ₆ ) -alkyl group, wherein R ^I and R ^II together with the nitrogen atom can form a 5-, 6- or 7-membered ring and m is a number 2, 3, 4, 5 or 6, - R ⁷ is a (C ₁ to C ₆ ) -alkyl group, in particular a methyl group, - X ^- is a physiologically acceptable anion, - the cycle of the formula (CH-1) represents all ring structures, the additional lic h may contain further heteroatoms such as nitrogen, oxygen or sulfur and may further carry fused ring structures, all of these ring structures may carry additional substituents, - Het represents an optionally substituted heteroaromatic, and - X ¹ represents a direct bond or a carbonyl group, by Mixture is obtained. Method according to claim 1, characterized in that that the time interval between the oxidative staining and the treatment of the regrown hairs at least 5 days. Method according to one of claims 1 or 2, characterized in that the means (A) immediately before Use of a composition (A1) containing at least one oxidation dye precursor, and a means (A2) containing at least one oxidizing agent, will be produced. Method according to one of claims 1 or 2, characterized in that the reactive carbonyl compound the agent (B1) is selected from 4-hydroxy-2-methoxybenzaldehyde, 3,4-dihydroxy-5-methoxybenzaldehyde, 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde, 2,4-dimethoxy-benzaldehyde, 2-chloro-3,4-dihydroxybenzaldehyde and 2-bromo-3,4-dihydroxybenzaldehyde. Method according to one of claims 1 to 3, characterized in that the C, H-acidic compound of the agent (B2) is selected from 1-allyl-1,2-dihydro-3,4,6-trimethyl-2-oxo-pyrimidinium, 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium and 2- (cyanomethyl) -benzimidazole or their physiologically acceptable salts. Process for dyeing grayed-on Asian hair, characterized in that the grayed hair parts are treated with an agent (B) immediately before use of - at least one agent (B1) containing in a cosmetic carrier 4-hydroxy-2-methoxybenzaldehyde and at least one further reactive carbonyl compound selected from 2-chloro-3,4-dihydroxybenzaldehyde, 2-bromo-3,4-dihydroxybenzaldehyde, 3,4-dihydroxy-5-methoxybenzaldehyde, 2,3-dihydro-1,5-dimethyl-3- oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde and 2,4-dimethoxybenzaldehyde, and - at least one agent (B2) containing, in a cosmetic carrier, a physiologically acceptable salt of 1-Allyl-1,2-dihydro-3,4,6-trimethyl-2-oxo-pyrimidiniums and optionally 2- (cyanomethyl) benzimidazole, is obtained by mixing. Method according to one of claims 1 to 6, characterized in that the means (B1) has a pH of 2 to 5. Method according to one of claims 1 to 7, characterized in that the means (B2) has a pH of 0.5 to 2.5. Method according to one of claims 1 to 8, characterized in that the means (B) immediately before Application, a further component (B3) is added, which in one cosmetically acceptable carrier at least one alkalizing agent contains. Method according to one of claims 1 to 9, characterized in that the ready-to-use agent (B) has a pH of 7 to 10. Method according to one of claims 9 or 10, characterized in that the means (B3) as an alkalizing agent Monoethanolamine, ammonia, sodium hydroxide, potassium hydroxide and / or Contains arginine. Use of an agent (B) according to one of the claims 1 to 11 for coloring the freshly grown hair roots of hair previously treated with an oxidative dye were. Use of an agent (B) according to one of the claims 1 to 11 for dyeing graying Asian hair. Multi-part dyeing kit for implementation of the method according to any one of claims 1 to 11, comprising Agent (B1) containing in a cosmetic carrier 4-hydroxy-2-methoxybenzaldehyde and at least one further reactive carbonyl compound selected from 2-chloro-3,4-dihydroxybenzaldehyde, 2-bromo-3,4-dihydroxybenzaldehyde, 3,4-Dihydroxy-5-methoxybenzaldehyde, 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxaldehyde and 2,4-dimethoxybenzaldehyde, and an agent (B2) which in a cosmetic carrier is 1-allyl-1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium bromide, 1,2-dihydro-1,3,4,6-tetramethyl-2-oxopyrimidinium and / or 2- (cyanomethyl) benzimidazole contains. Multi-part staining kit according to claim 14, additionally containing an agent (A1) containing at least one Dye precursor, and an agent (A2) containing at least an oxidizing agent.