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WO1996005800A1 - Dihydroxybenzenes aminomethyles - Google Patents

Dihydroxybenzenes aminomethyles Download PDF

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Publication number
WO1996005800A1
WO1996005800A1 PCT/EP1995/003156 EP9503156W WO9605800A1 WO 1996005800 A1 WO1996005800 A1 WO 1996005800A1 EP 9503156 W EP9503156 W EP 9503156W WO 9605800 A1 WO9605800 A1 WO 9605800A1
Authority
WO
WIPO (PCT)
Prior art keywords
hair
bis
components
hydroxyethyl
developer
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP1995/003156
Other languages
German (de)
English (en)
Inventor
David Rose
Bernd Meinigke
Horst Höffkes
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of WO1996005800A1 publication Critical patent/WO1996005800A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
    • C07C215/50—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain

Definitions

  • the invention relates to oxidation colorants for dyeing human hair, which contain customary developer components and aminomethyl-substituted dihydroxybenzene derivatives as coupler components.
  • oxidation hair colorants play a preferred role for dyeing hair because of their intense colors and good fastness properties.
  • hair dyes contain oxidation dye precursors in a cosmetic carrier.
  • Developer components and coupler components are used as oxidation dye precursors.
  • the developer components form the actual dyes under the influence of oxidizing agents or of atmospheric oxygen with one another or under coupling with one or more coupler components.
  • Special representatives are, for example, p-toluenediamine, 2,4,5,6-tetraaminopyrimidine, p-aminophenol, N, N-bis (2-hydroxyethyl) -p-phenylenediamine, 2- (2,5-diaminophenyl) - ethanol, 2- (2,5-diaminophenoxy) ethanol, l-phenyl-3-carboxyamido-4-amino-pyrazolon-5 and 4-amino-3-methylphenol, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6-triaminohydroxypyrimidine.
  • M-Phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenols are generally used as coupler components.
  • coupler substances ⁇ -naphthol, pyrogallol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, l-phenyl3-methyl- pyrazolon-5, 2,4-dichloro-3-aminophenol, l, 3-bis (2,4-diaminophenoxy) propane, 2-chloro-resorcinol, 2-chloro-6-methyl-3-aminophenol and 2-methylresorcinol.
  • a certain developer component can also form very different shades of color by combination with different couplers. Nevertheless, it is often not possible to achieve the multitude of natural hair color shades with the help of a single developer component. In practice, therefore, a combination of different developer components and coupler components is usually required in order to obtain a single, natural-looking hair color. There is therefore a constant need for new, improved coupler / developer combinations.
  • oxidation dye precursors must first of all meet the following requirements: they must develop the desired color shades with sufficient intensity and authenticity in the oxidative coupling. They must also have a good ability to draw on human hair, with no noticeable differences between stressed and freshly regrown hair (leveling ability). They should be resistant to light, heat and the influence of chemical reducing agents, e.g. B. against permanent wave liquids. After all, they should not stain the scalp too much, and above all they should be harmless in toxicological and dermatological terms.
  • the European patent application EP 0 398 702 A2 discloses hair colorants which contain aminomethyl-substituted m-aminophenols as couplers.
  • the present invention relates to oxidation hair colorants for dyeing keratin fibers, in particular human hair, containing coupler components and developer components in a water-containing carrier, characterized in that at least one conventional developer component in an amount of 0.01 to 20% by weight. %, preferably 0.5 to 5% by weight, and a dihydroxybenzene derivative of the formula I as the coupler component
  • X is a hydrogen atom, a halogen atom or a Cj-C / j-alkyl group
  • R * and R ⁇ independently of one another represent hydrogen, Cj-C4-alkyl group or C2-C_ ⁇ , -hydroxyalky1- groups and the unit NR ⁇ R ⁇ also a heterocyclic
  • non-aromatic optionally containing an oxygen or nitrogen atom, five or six ring.
  • N, N-bis- ( ⁇ -hydroxyethyl) -2,4-dioxybenzylamine or N, N-bis- ( ⁇ -hydroxyethyl) -2,4-dioxy-3-methylbenzylamine are particularly suitable as coupler components.
  • Some of the dihydroxybenzene derivatives of the formula I are known from the literature and can be prepared by known synthesis methods, for example by aminomethylation according to Mannich (for further details see the example section), but in some cases they are also new, such as N, N-bis- (ß-hydroxy) - ethyl) -2,4-dioxy-3-methylbenzylamine; his synthesis is described in detail in Example 1.
  • the substances already described in more detail above can be used as customary developer components which can be used in the oxidation hair colorants according to the invention.
  • the developer and coupler components can be used both as free bases and in the form of their inorganic or organic salts, e.g. the hydrochloride or hydrobromide.
  • the colorants according to the invention provide a broad spectrum of oxidation colors of interest in terms of application technology in the range from yellow-brown to dark brown shades of high brilliance, good leveling ability and good fastness properties.
  • Preferred colorants provide shades in the red range; Such nuances can be achieved with the oxidation hair colorants according to the invention in particular when the developer component is 2,4,5,6-tetraamino-pyrimidine.
  • the hair colorants according to the invention contain, in addition to the dihydroxybenzene derivatives of the formula I and the developer components, customary direct dyes, for example from the group of the nitrophenylenediamines, nitroaminophenols, anthraquinones or indophenols, such as, for example, those under the international names or, in addition to the dihydroxybenzene derivatives of the formula I and the developer components Trade names HC Yellow 2, HC Yellow 4, Methyl Yellow, Fluor Yellow, Basic Yellow 57, Disperse Orange 3, HC Red 3, HC Red BN, Cardinal Red, Red Y, Red X, Basic Red 76, HC Blue 2, Nitro Blue, Disperse Blue 3, Basis Blue 99, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Disperse Black 9, Basis Brown 16, Picramic Acid and Rodol 9 R Connections, in an amount of 0.01 to 20 wt .-%, based on the entire oxidation hair dye.
  • customary direct dyes for example from the group of the
  • dihydroxybenzene derivatives of formula I the developer components or the optional direct dyes each represent uniform compounds. Rather, mixtures of various dihydroxybenzene derivatives of the formula I, developer components and substantive dyes can also be used in the hair colorants according to the invention.
  • dihydroxybenzene derivatives of the formula I other conventional, above-mentioned. Coupler components may be included.
  • developer components and coupler components are generally used in approximately molar amounts to one another. If the molar use has also proven to be expedient, a certain excess of individual oxidation dye precursors is not disadvantageous, so that developer components and coupler components can be present in a molar ratio of 1: 0.5 to 1: 2 .
  • the oxidation dye precursors are incorporated in a suitable water-containing carrier.
  • suitable water-containing carrier are e.g. Creams, emulsions, gels or also surfactant-containing foaming solutions, e.g. Sha poos, foam aerosols or other preparations that are suitable for use on the hair.
  • the water-containing carrier usually contains wetting and emulsifying agents such as anionic, nonionic or ampholytic surfactants, eg fatty alcohol sulfates, alkane sulfonates, ⁇ -olefin sulfonates, fatty alcohol polyglycol ether sulfates, alkyl glycosides, ethylene oxide addition products on fatty alcohols, on fatty acids, on alkylphenols, on sorbitan fatty acid esters, on fatty acid partial glycerides and fatty acid alkanolamides; Thickeners, e.g. B.
  • anionic, nonionic or ampholytic surfactants eg fatty alcohol sulfates, alkane sulfonates, ⁇ -olefin sulfonates, fatty alcohol polyglycol ether sulfates, alkyl glycosides, ethylene oxide addition products on fatty alcohols, on fatty acids, on alkylphenols, on
  • fatty alcohols fatty acids, paraffin oils, fatty acid esters and other fat components in emulsified form
  • water-soluble polymeric thickeners such as natural gums, e.g. B. gum arabic, karaya gum, guar gum, locust bean gum, linseed gums; biosynthetic gums, for example xanthan gums and dextrans; synthetic gums, e.g. B. agar and algin, starch fractions and derivatives such as amylose, amylopectin and Dextri ⁇ ne; modified cellulose molecules, e.g. B. methyl cellulose, hydroxyalkyl cellulose and carboxymethyl cellulose; Clays such as B.
  • the constituents of the water-containing carrier are used for the production of the hair colorants according to the invention in amounts customary for this purpose;
  • emulsifiers are used in concentrations of 0.5 to 30 wt .-% and thickeners in concentrations of 0.1 to 25 wt .-% of the total colorant.
  • the oxidative development of the color can in principle be carried out with atmospheric oxygen.
  • a chemical oxidizing agent is preferably used, especially when a lightening effect on the hair is desired in addition to the coloring.
  • Particularly suitable oxidizing agents are hydrogen peroxide or its adducts with urea, melamine or sodium borate, and mixtures of such hydrogen peroxide adducts with potassium peroxide disulfate.
  • the preparation of the oxidizing agent is expediently mixed with the preparation from the oxidation dye precursors immediately before hair coloring.
  • the resulting ready-to-use hair dye preparation should preferably have a pH in the range from 6 to 10. It is particularly preferred to use the hair dye in a weakly alkaline environment.
  • the application temperatures can be in a range between 15 and 40 ° C. After an exposure time of approx. 30 minutes, the hair dye is removed from the hair to be colored by rinsing. Washing with a shampoo is not necessary if a carrier with a high tenside content, e.g. a coloring shampoo was used.
  • Hair colorants according to the invention were produced in the form of a hair color cream emulsion in the following composition:
  • Coupler component (K1-K2) 0.0075 mol
  • the ingredients were mixed together in order. After the oxidation dye precursors and the inhibitor had been added, the pH of the emulsion was first adjusted to 10 using concentrated ammonia solution, and the mixture was then made up to 100 g with water.
  • the oxidative development of the color was carried out with 3% hydrogen peroxide solution as the oxidation solution.
  • 100 g of the emulsion were mixed with 50 g of hydrogen peroxide solution (3%) and mixed.
  • the coloring cream was applied to approx. 5 cm long strands of standardized, 90% gray but not specially pretreated human hair and left there for 30 minutes at 27 ° C. After the dyeing process had ended, the hair was rinsed, washed with a conventional shampoo and then dried.
  • the developer components were E1 to E7

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)

Abstract

Des teintures d'oxydation pour les cheveux contiennent, comme composants copulateurs, des dihydroxybenzènes aminométhylés avec des composants développeurs usuels.
PCT/EP1995/003156 1994-08-18 1995-08-09 Dihydroxybenzenes aminomethyles Ceased WO1996005800A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4429344.5 1994-08-18
DE19944429344 DE4429344A1 (de) 1994-08-18 1994-08-18 Aminomethylierte Dihydroxybenzole

Publications (1)

Publication Number Publication Date
WO1996005800A1 true WO1996005800A1 (fr) 1996-02-29

Family

ID=6526024

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1995/003156 Ceased WO1996005800A1 (fr) 1994-08-18 1995-08-09 Dihydroxybenzenes aminomethyles

Country Status (2)

Country Link
DE (1) DE4429344A1 (fr)
WO (1) WO1996005800A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1222700A (fr) * 1959-01-20 1960-06-13 Oreal Nouveaux dérivés aminohydroxylés aromatiques utilisables comme colorants d'oxydation, procédé de préparation et procédé d'utilisation de ces dérivés
WO1993010744A2 (fr) * 1991-12-03 1993-06-10 L'oreal PROCEDE DE TEINTURE DES FIBRES KERATINIQUES AVEC UNE ALCOXYMETAPHENYLENEDIAMINE A pH ACIDE ET COMPOSITIONS MISES EN ×UVRE

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1222700A (fr) * 1959-01-20 1960-06-13 Oreal Nouveaux dérivés aminohydroxylés aromatiques utilisables comme colorants d'oxydation, procédé de préparation et procédé d'utilisation de ces dérivés
WO1993010744A2 (fr) * 1991-12-03 1993-06-10 L'oreal PROCEDE DE TEINTURE DES FIBRES KERATINIQUES AVEC UNE ALCOXYMETAPHENYLENEDIAMINE A pH ACIDE ET COMPOSITIONS MISES EN ×UVRE

Also Published As

Publication number Publication date
DE4429344A1 (de) 1996-02-22

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