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WO2011051087A1 - Agent de coloration - Google Patents

Agent de coloration Download PDF

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Publication number
WO2011051087A1
WO2011051087A1 PCT/EP2010/064969 EP2010064969W WO2011051087A1 WO 2011051087 A1 WO2011051087 A1 WO 2011051087A1 EP 2010064969 W EP2010064969 W EP 2010064969W WO 2011051087 A1 WO2011051087 A1 WO 2011051087A1
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WO
WIPO (PCT)
Prior art keywords
amino
acid
agent
hydroxyethyl
copolymer
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/EP2010/064969
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German (de)
English (en)
Inventor
Diane Metten
Ina Franke
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
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Filing date
Publication date
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Publication of WO2011051087A1 publication Critical patent/WO2011051087A1/fr
Anticipated expiration legal-status Critical
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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
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)

Definitions

  • the present invention relates to agents for the color change of keratin-containing fibers, in particular human hair, containing 1, 3-butanediol, and a method for dyeing keratin-containing fibers, in particular human hair.
  • Preparations for tinting and coloring hair are an important type of cosmetic. They may be used to slightly or more intensely nuance the natural hair color according to the desires of the corresponding person, to achieve a completely different hair color, or to mask unwanted color tones, such as gray tones.
  • Conventional hair dyes are formulated either on the basis of oxidation dyes or on the basis of substantive dyes, depending on the desired color or durability of the dyeing. Often, combinations of oxidation dyes and direct dyes are used to achieve special nuances.
  • Colorants based on oxidation dyes result in brilliant and lasting color shades. However, they require the use of strong oxidizing agents such as hydrogen peroxide solutions.
  • Such colorants contain oxidation dye precursors, so-called developer components and coupler components.
  • the developer components form under the influence of oxidizing agents or atmospheric oxygen with each other or under coupling with one or more coupler components, the actual dyes.
  • Colorants based on direct dyes do not require an oxidizing agent and can be formulated at pH values in the region of the neutral point; but give less permanent colorations.
  • the absorption capacity of the dye molecules on the hair as well as the gloss of the colored hairs can not fully satisfy in many cases either.
  • combination preparations have been developed to reduce the burden of the usual multi-stage process, especially in direct application by consumers.
  • these preparations additionally contain active ingredients which were formerly reserved for hair aftertreatment agents. The consumer thus saves an application step; At the same time, packaging costs are reduced because one product is less needed.
  • Another field of application for such combination preparations is the color refreshment of previously oxidatively dyed fibers.
  • 1,3-butanediol in color-changing agents preferably in combination with a polymer of the diallyldimethylammonium chloride type, can increase the gloss of the fibers Wet combability of the fibers can be improved and the durability of the color change achieved can be increased.
  • a first subject of the present invention are therefore agents for the color change of keratinic fibers containing in a cosmetically acceptable carrier at least one dye and / or a dye precursor and 1, 3-butanediol.
  • Keratin fibers are wool, furs, feathers and especially human hair to understand.
  • the colorants of the invention can in principle but also for dyeing other natural fibers such.
  • cotton, jute, sisal, linen or silk modified natural fibers, such as regenerated cellulose, nitro, alkyl or hydroxyalkyl or acetyl cellulose can be used.
  • color change of keratin fibers used according to the invention encompasses any form of color change of the fibers, including in particular the color changes encompassed by the terms tinting, bleaching, oxidative dyeing, semipermanent dyeing, permanent dyeing and temporary dyeing, in which a dye and / or a dye precursor is used.
  • the inventive compositions contain the 1, 3-butanediol preferably in an amount of 0.01 to 10 wt .-%, in particular in an amount of 0, 1 to 5 wt .-%, most preferably in an amount of 0.5 to 2 wt .-%, each based on the ready-to-use agent.
  • the homopolymers and / or copolymers of diallyldimethylammonium chloride have been found to be most preferred.
  • the agents according to the invention may contain a homopolymer of diallyldimethylammonium chloride.
  • agents which, in addition to the 1,3-butylene glycol, contain a copolymer of diallyldimethylammonium chloride and a nonionic and / or anionic comonomer.
  • Preferred comonomers according to the invention are acrylic acid, methacrylic acid, acrylamide, and methacrylamide. Accordingly, agents containing a copolymer of diallyldimethylammonium chloride with acrylamide and / or acrylic acid and / or methacrylamide and / or methacrylic acid are also preferred.
  • Such polymers are sold commercially, for example under the trade name Merquat ® by the company Ondeo Nalco. These are for example:
  • the agents according to the invention preferably contain the diallyldimethylammonium chloride polymer in an amount of from 0.01 to 10% by weight, in particular in an amount of from 0.1 to 5% by weight, especially preferably in an amount of 0.5 to 2 wt .-%, each based on the ready-to-use agent.
  • compositions according to the invention also contain at least one thickening polymer which has no diallyldimethylammonium chloride units ,
  • Acrylamide Copolymer Acrylamide / Sodium Acrylate Copolymer, Acrylamide / Sodium Acryloyl Dimethyl Taurate Copolymer, Acrylates / Acetoacetoxyethyl Methacrylate Copolymer, Acrylates / Beheneth-25 Methacrylate Copolymer, Acrylates / C 10-30 Alkyl Acrylate Crosspolymer, Acrylates / Ceteth-20 Itaconate Copolymer, Acrylates / Ceteth -20 Methacrylate Copolymer, Acrylates / Laureth-25 Methacrylate Copolymer, Acrylates / Palmeth-25 Acrylate Copolymer, Acrylates / Palmeth-25 Itaconate Copolymer, Acrylates / Steareth-50 Acrylate Copolymer, Acrylates / Steareth-20 Itaconate Copolymer, Acrylates / Steareth-20 Methacrylate Copolymer, Acrylates / Steary
  • thickening polymers of the polyacrylic acid type in particular the polymers known under the INCI names Calcium Potassium Carbomer, Carbomer, Potassium Carbomer and Sodium Carbomer.
  • the thickening polymers are preferably present in the compositions according to the invention in amounts of from 0.0001 to 4% by weight, in particular from 0.01 to 2% by weight, very particularly preferably in amounts of from 0.1 to 1% by weight, in each case based on the ready-to-use agent.
  • compositions according to the invention contain, as in a first embodiment as a color-modifying component, at least one substantive dye.
  • a color-modifying component at least one substantive dye.
  • These are dyes that raise directly on the hair and do not require an oxidative process to form the color.
  • Direct dyes are usually organic compounds such as nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones or indophenols.
  • the substantive dyes are each preferably used in an amount of 0.001 to 20 wt .-%, based on the total application preparation.
  • the total amount of substantive dyes is preferably at most 20% by weight.
  • Direct dyes can be subdivided into anionic, cationic and nonionic 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 Disulfonic acid) (Cl 47.005, D & C Yellow No. 10, Food Yellow No.
  • Acid Blue 1 bis [4- (diethylamino) phenyl] (5-hydroxy-2,4- disulfophenyl) -carbenium inner salt, calcium salt (2: 1) (Cl 42,051, Acid Blue 3), N- [4 - [(2,4-disulfophenyl) [4- [ethyl (phenylmethyl) amino) phenyl] methylene] -2,5-cyclohex
  • ethylbenzene methanaminium hydroxide, inner salt, sodium salt (CI 42.080, Acid Blue 7), (2-sulfophenyl) di [4- (ethyl ((4-sulfophenyl) methyl) amino) phenyl] -carbenium disodium salt betaine (CI 42.090, Acid Blue 9, FD & C Blue No.
  • Preferred anionic substantive dyes are those having the international designations or trade names tetrabromophenol blue, 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.
  • Particularly suitable cationic direct dyes are 9- (dimethylamino) benzo [a] phenoxazine-7-ium chloride (Cl 51, 175; Basic Blue 6), di [4- (diethylamino) phenyl] [4- (ethylamino)].
  • 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
  • Preferred cationic substantive dyes of group (c) are, in particular, the compounds disclosed in the priority document with the designations (DZ1) to (DZ9).
  • the compounds of the formulas (DZ1), (DZ3) and (DZ5), which are also known by the names 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.
  • Suitable nonionic substantive dyes are in particular 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-
  • 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 salts thereof, 1, 4- Diamino-2-nitrobenzene (Cl 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]
  • suitable yellow nitro dyes are: 1,2-diamino-4-nitrobenzene (Cl 76.020), 1 - [(2-hydroxyethyl) amino] -2-nitrobenzene (HC Yellow 2), 1- (2-hydroxyethoxy) -2- [(2-hydroxyethyl) amino] -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,
  • 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 (Cl 61, 545, Disperse Blue 23), 1- [(2-hydroxyethyl) amino] -4-methylamino-9,10-anthraquinone (Cl 61, 505, Disperse Blue 3), 2 - [(2-aminoethyl) amino] -9 , 10-anthraquinone (HC Orange 5), 1-amino-4-hydroxy-9,10-anthraquinone (Cl 60.710, Disperse Red 15), 1-hydroxy-4 - [(4-methyl-2-sulfophenyl) amino] -9,10-anthraquinone, 7-beta-D-glucopyranosyl-9,10-dihydro-1-
  • Suitable neutral azo dyes are in particular: 1 - [di (2-hydroxyethyl) amino] -3-methyl-4 - [(4-nitrophenyl) azo] benzene (Cl 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 (Cl 1 1855 Disperse Yellow 3), 4 - [(4-nitrophenyl) azo] aniline (Cl 1 1, 005, Disperse Orange 3).
  • Preferred nonionic substantive dyes are those under the international 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 1, HC Red 13, HC Red BN, HC Blue 2, HC Blue 1 1, 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-
  • the substantive dyes each represent uniform compounds. Rather, due to the production process for the individual dyes, minor amounts of other components may be included, as far as these do not adversely affect the dyeing result or for other reasons, e.g. toxicological, must be excluded.
  • direct dyes also naturally occurring dyes may be used, as for example in henna red, henna neutral, henna black, chamomile, sandalwood, black tea, buckthorn bark, sage, bluewood, madder root, Catechu, Sedre and alkano root are included.
  • Very particular preferred substantive dyes according to the invention are Basic Brown 16, Basic Yellow 57, Basic Blue 99, HC Blue 2, 4-amino-3-nitrophenol, HC Yellow 13, HC Blue No. 12, 1-Amino-5-chloro-4 (2,3-dihydroxypropylamino) -2-nitrobenzene (Red Y), Acid Violet 43, 4 - [(2-hydroxyethyl) amino] -3-nitrophenol (Red B54). hydroxyethyl-2-nitro-toluidine.
  • the substantive dyes are each preferably used in an amount of 0.001 to 20 wt .-%, based on the total application preparation.
  • the total amount of substantive dyes is preferably at most 20% by weight.
  • the agent may contain at least one dye precursor.
  • both oxidation dye precursors and precursors of natural analog hair dyes understood each under the action of an oxidizing agent (optionally oxygen from the air) form the actual dyeing the hair dyes.
  • oxidation colorants For permanent, intensive colorations with corresponding fastness properties, so-called oxidation colorants are used. Such colorants usually contain oxidation dye precursors, so-called developer components and coupler components. The developer components form under the influence of oxidizing agents or of atmospheric oxygen with one another or with coupling with one or more coupler components, the actual dyes.
  • the oxidation dyes are characterized by excellent, long-lasting dyeing results. For naturally acting dyeings, however, usually a mixture of a larger number of oxidation dye precursors must be used; In many cases, direct dyes are still used for shading.
  • developer component a p-phenylenediamine derivative or one of its physiologically acceptable salts.
  • Particularly preferred p-phenylenediamines are selected from p-phenylenediamine, p-toluenediamine, 2-chloro-p-phenylenediamine, N, N-bis (2-hydroxyethyl) -p-phenylenediamine and N- Phenyl-p-phenylenediamine, 2- (2-hydroxyethyl) -p-phenylenediamine, N- (4-amino-3-methylphenyl) -N- [3- (1 H -imidazol-1-yl) propyl] amine and their physiologically acceptable salts.
  • developer component compounds which contain at least two aromatic nuclei which are substituted by amino and / or hydroxyl groups.
  • Preferred binuclear developer components are in particular: N, N'-bis (2-hydroxyethyl) -N, N'-bis (4'-aminophenyl) -1,3-diamino-propan-2-ol and bis (2-hydroxyethyl) Hydroxy-5-aminophenyl) -methane and their physiologically acceptable salts.
  • the developer component may be preferred according to the invention to use as the developer component a p-aminophenol derivative or one of its physiologically tolerable salts.
  • Preferred p-aminophenols are in particular p-aminophenol, N-methyl-p-aminophenol, and 4-amino-3-methyl-phenol and their physiologically tolerated salts.
  • the developer component may be selected from o-aminophenol and its derivatives such as 2-amino-5-methylphenol and its physiologically acceptable salts.
  • the developer component may be selected from heterocyclic developer components, such as the pyridine, pyrimidine, pyrazole, pyrazolo-pyrimidine derivatives and their physiologically acceptable salts.
  • Preferred pyrimidine derivatives are in particular 2,4,5,6-tetraaminopyrimidine and 4-hydroxy-2,5,6-triaminopyrimidine and their physiologically tolerated salts.
  • a preferred pyrazole derivative is 4,5-diamino-1- (2-hydroxyethyl) pyrazole and its physiologically acceptable salts.
  • Coupler components do not form a significant color within the framework of the oxidative dyeing alone, but always require the presence of developer components. Therefore, it is preferred according to the invention that at least one coupler component is additionally used when using at least one developer component.
  • Coupler components according to the invention allow 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.
  • Couplers are preferably cyclic compounds which carry on cycle at least two groups selected from (i) optionally substituted amino groups and / or (ii) hydroxy groups. These groups are conjugated by a double bond system. When the cyclic compound is a six-membered ring, said groups are preferably in ortho position or meta position to each other.
  • coupler components m-phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenol derivatives are generally used.
  • Suitable coupler substances are in particular 1-naphthol, 1, 5- and 2,7-dihydroxynaphthalene, 1-acetoxy-2-methoxynaphthalene, resorcinol, 4-chloro-resorcinol and 2-amino-3-hydroxypyridine and their physiologically tolerated salts.
  • preferred coupler components are
  • (C) m-Diaminobenzene and its derivatives such as, for example, 2,4-diaminophenoxyethanol, 1,3-bis- (2 ', 4'-diaminophenoxy) -propane, 1-methoxy-2-amino-4- (2' - hydroxyethylamino) benzene, 2,6-bis (2'-hydroxyethylamino) -1-methylbenzene, 2 - ( ⁇ 3 - [(2-hydroxyethyl) amino] -4-methoxy-5-methylphenyl ⁇ amino) ethanol and 2 - ( ⁇ 3 - [(2-hydroxyethyl) amino] -2-methoxy-5-methylphenyl ⁇ amino) ethanol,
  • pyridine derivatives such as 3-amino-2-methylamino-6-methoxypyridine, 2,6-diaminopyridine, 2,6-dihydroxy-3,4-dimethylpyridine, 2-amino-3-hydroxypyridine and 3,5-diamino 2,6-dimethoxy,
  • Coupler components which are particularly preferred according to the invention are 1-naphthol, 1,5- and 2,7-dihydroxynaphthalene, 5-amino-2-methylphenol, 2-amino-3-hydroxypyridine, resorcinol, 4-chlororesorcinol, 2-methylresorcinol and 2, 6-Dihydroxy-3,4-dimethylpyridine and their physiologically acceptable salts.
  • the inventive compositions contain both the developer components and the coupler components preferably in an amount of 0.005 to 20 wt .-%, preferably 0, 1 to 5 wt .-%, each based on their total weight.
  • developer components and coupler components are generally used in approximately molar amounts to each other.
  • a certain excess of individual oxidation dye precursors is not disadvantageous, 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, may be included.
  • the agents according to the invention comprise at least one precursor of a naturally-analogous dye.
  • precursors of natural analogue Dyes are preferably those indoles and indolines used which have at least one hydroxyl or amino group, preferably as a substituent on the six-membered ring.
  • Particularly preferred derivatives of indoline are 5,6-dihydroxyindoline and 2,3-dioxoindoline (isatin) and their physiologically acceptable salts.
  • a particularly preferred derivative of indole is 5,6-dihydroxyindole and its physiologically acceptable salts.
  • the agents according to the invention preferably contain the indole or indoline derivatives in an amount of 0.05-10% by weight, preferably 0.2-5% by weight, in each case based on their total weight.
  • the agents of the second embodiment of the invention contain with particular preference additionally hydrogen peroxide.
  • agents according to the invention for dyeing and, if appropriate, simultaneous lightening of keratinic fibers are particularly preferred, which contain 0.5 to 15% by weight, preferably 1 to 12.5% by weight, particularly preferably 2.5 to 10% by weight and in particular 3 to 6 wt .-% hydrogen peroxide (calculated as 100% H 2 0 2 ) included.
  • the hydrogen peroxide may also be used in the form of its attachment compounds to solid supports, preferably hydrogen peroxide itself is used.
  • the hydrogen peroxide is used as a solution or in the form of a solid addition compound of hydrogen peroxide to inorganic or organic compounds, such as sodium perborate, sodium percarbonate, magnesium percarbonate, sodium percarbamide, polyvinylpyrrolidone n H 2 0 2 (n is a positive integer greater than 0), urea peroxide and melamine peroxide, used.
  • aqueous hydrogen peroxide solutions are very particularly preferred according to the invention.
  • concentration of a hydrogen peroxide solution is determined on the one hand by the legal requirements and on the other hand by the desired effect; preferably 6 to 12 percent solutions in water are used.
  • Such surfactants having an HLB of 5.0 and greater are preferred.
  • HLB value For the definition of the HLB value, explicit reference is made to the statements in Hugo Janistyn, Handbuch der Kosmetika und Riechstoffe, III. Volume: The personal care products, 2nd edition, Dr. med. Alfred Hüthig Verlag Heidelberg, 1973, pages 68-78 and Hugo Janistyn, Paperback of modern perfumery and cosmetics, 4th edition, Scientific Publishing Company m.b.H. Stuttgart, 1974, pages 466-474, as well as the original works cited therein.
  • non-ionic surface-active substances are substances that are commercially available as solids or liquids in pure form because of their ease of processing.
  • the definition of purity in this context does not refer to chemically pure compounds. Rather, especially when it comes to natural-based products, mixtures of different homologs can be used, for example, with different alkyl chain lengths, such as those obtained with products based on natural fats and oils. Even with alkoxylated products, mixtures of different degrees of alkoxylation are usually present.
  • purity refers to this Rather, it refers to the fact that the chosen substances should preferably be free from solvents, stabilizers and other impurities.
  • Preferred nonionic surfactants are:
  • fatty alkyl groups having 8 to 22, in particular 10 to 16, carbon atoms in the fatty alkyl group and 1 to 30, especially 1 to 15, ethylene oxide and / or propylene oxide units.
  • Preferred fatty alkyl groups are, for example, lauryl, myristyl, cetyl, but also stearyl, isostearyl and oleyl groups.
  • Particularly preferred compounds of this class are, for example, lauryl alcohol with 2 to 4 ethylene oxide units, oleyl and cetyl alcohol with 5 to 10 ethylene oxide, cetyl alcohol and stearyl alcohol and mixtures thereof with 10 to 30 ethylene oxide units and the commercial product Aethoxal ® B (Henkel), Lauryl alcohol with 5 ethylene oxide and 3 propylene oxide units.
  • the alkoxy group has no OH group at the end but is "closed” in the form of an ether, in particular a C 1 -C 4 -alkyl ether.
  • An example of such a compound is the commercially available product ® Dehypon LT 054, a Ci-2 -i8 Fettalkoholol + 4.5 ethylene oxide-butyl ether.
  • - alkoxylated fatty acids having 8 to 22, in particular 10 to 16, carbon atoms in the fatty acid group and 1 to 30, in particular 1 to 15, ethylene oxide and / or propylene oxide units.
  • Preferred fatty acids are, for example, lauric, myristic, palmitic, stearic, isostearic and oleic acids.
  • Examples of preferred compounds are glycerol monolaurate + 20 ethylene oxide and glycerol monostearate + 20 ethylene oxide.
  • Polyglycerol esters and alkoxylated polyglycerol esters are for example poly (3) glycerol diisostearate (commercial product: Lameform ® TGI (Henkel)) and poly (2) glycerinpolyhydroxy- stearate (commercial product: Dehymuls ® PGPH (Henkel)).
  • Sorbitan fatty acid esters and alkoxylated sorbitan fatty acid esters such as sorbitan monolaurate and sorbitan monolaurate + 20 ethylene oxide (EO).
  • Alkylphenols and Alkylphenolalkoxylate having 6 to 21, in particular 6 to 15, carbon atoms in the alkyl chain and 0 to 30 ethylene oxide and / or propylene oxide units.
  • Preferred representatives of this class are, for example, nonylphenol + 4 EO, nonylphenol + 9 EO, octylphenol + 3 EO and octylphenol + 8 EO.
  • nonionic surfactants are the alkoxylated fatty alcohols, the alkoxylated fatty acids and the alkylphenols and alkylphenol alkoxylates.
  • Agents according to the invention which contain non-ionic surface-active substances in amounts of 1 to 5% by weight have proved to be particularly advantageous.
  • the color-modifying agents according to the invention may contain all known in such preparations active ingredients, additives and excipients.
  • the agents contain at least one surfactant, wherein in principle both anionic and zwitterionic, ampholytic, nonionic and cationic surfactants are suitable.
  • Anionic surfactants may be very particularly preferred.
  • Preferred anionic surfactants are alkyl sulfates, ether carboxylic acid salts having 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule such as C 12 H 25 - (C 2 H 4 O) 6 -CH 2 -COONa and in particular salts of saturated and especially unsaturated C 8 -C 22 Carboxylic acids such as oleic acid, stearic acid, isostearic acid and palmitic acid.
  • anionic surfactants should preferably be present in solid, in particular powder form. Very particular preference is given to solid soaps, especially sodium stearate, at room temperature. These are preferably present in amounts of 5 to 20 wt .-%, in particular 10 to 15 wt .-%, before.
  • Suitable nonionic surfactants are in particular C 8 -C 22 -alkyl mono- and oligoglycosides and their ethoxylated analogs. In particular, the nonethoxylated compounds have been found to be particularly suitable.
  • cationic surfactants which can be used in the hair treatment compositions according to the invention are, in particular, quaternary ammonium compounds.
  • ammonium halides such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, eg. Cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, distearyldimethylammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and
  • Tricetylmethylammonium chloride Tricetylmethylammonium chloride.
  • Further cationic surfactants which can be used according to the invention are the quaternized protein hydrolysates.
  • 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.
  • esterquats such as the Distearoylethylhydroxyethylammoniummethosulfat available in a blend with Cetearylalkohle under the name Dehyquart® ® F 75 miles.
  • the compounds containing alkyl groups used as surfactants may each be uniform substances. However, it is generally preferred to use native vegetable or animal raw materials in the production of these substances, so that substance mixtures having different alkyl chain lengths depending on the respective raw material are obtained.
  • the compositions according to the invention may contain at least one ammonium compound from the group of ammonium chloride, ammonium carbonate, ammonium bicarbonate, ammonium sulfate and / or ammonium carbamate in an amount of from 0.5 to 10, preferably from 1 to 5,% by weight, based on the total composition of the composition ,
  • dyeing and / or brightening agents according to the invention may contain further active ingredients, auxiliaries and
  • 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, polysiloxanes with quaternary groups, dimethyldiallylammonium chloride polymers, acrylamide-dimethyldiallylammonium chloride copolymers, diethyl sulfate-quaternized dimethylaminoethylmethacrylate-vinylpyrrolidone copolymers, vinylpyrrolidone-imidazolinium methochloride copolymers and quaternized polyvinylalcohol,
  • zwitterionic and amphoteric polymers for example acrylamidopropyltrimethylammonium chloride / acrylate copolymers and octylacrylamide / methyl methacrylate / tert-butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate copolymers,
  • anionic polymers such as 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-butyl acrylamide 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. Bentonite or fully synthetic hydrocolloids such as e.g. polyvinyl alcohol,
  • Structurants such as maleic acid and lactic acid
  • hair-conditioning compounds such as phospholipids, for example soya lecithin, egg lecithin and cephalins,
  • 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,
  • Solvents and mediators such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol and diethylene glycol,
  • fiber-structure-improving active ingredients in particular mono-, di- and oligosaccharides such as, for example, glucose, galactose, fructose, fructose and lactose,
  • quaternized amines such as methyl-1-alkylamidoethyl-2-alkylimidazolinium methosulfate
  • Anti-dandruff agents such as Piroctone Olamine, Zinc Omadine and Climbazole,
  • Light stabilizers in particular derivatized benzophenones, cinnamic acid derivatives and triazines, substances for adjusting the pH, for example customary acids, in particular edible acids and bases,
  • Active ingredients such as panthenol, pantothenic acid, allantoin, pyrrolidonecarboxylic acids and their salts, and bisabolol,
  • Vitamins, provitamins and vitamin precursors in particular those of groups A, B 3 , B 5 , B 6 , C, E, F and H,
  • Plant extracts such as extracts of green tea, oak bark, nettle, witch hazel, hops, chamomile, burdock root, horsetail, hawthorn, lime blossom, almond, aloe vera, spruce needle, horse chestnut, sandalwood, juniper, coconut, mango, apricot, lime, wheat, kiwi , Melon, orange, grapefruit, sage, rosemary, birch, mallow, meadowfoam, quenelle, yarrow, thyme, lemon balm, toadstool, coltsfoot, marshmallow, meristem, ginseng and ginger root ,.
  • Bodying agents such as sugar esters, polyol esters or polyol alkyl ethers,
  • Fats and waxes such as spermaceti, beeswax, montan wax and paraffins, fatty alcohols and
  • Swelling and penetration substances such as glycerol, propylene glycol monoethyl ether, carbonates,
  • Opacifiers such as latex, styrene / PVP and styrene / acrylamide copolymers
  • Pearlescing agents such as ethylene glycol mono- and distearate and PEG-3-distearate,
  • Propellants such as propane-butane mixtures, N 2 O, dimethyl ether, C0 2 and air,
  • compositions according to the invention may contain the ingredients in a suitable aqueous, alcoholic or aqueous-alcoholic carrier.
  • 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.
  • Preferred agents according to the invention are characterized in that they additionally comprise a nonaqueous solvent, particularly preferred compositions according to the invention the solvent in a concentration of 0, 1-30 weight percent, preferably in a concentration of 1 - 20 weight percent, most preferably in a concentration of 2 - 10 weight percent, each based on the agent included.
  • the solvent is selected from ethanol, n-propanol, isoropanol, n-butanol, propylene glycol, n-butylene glycol, glycerol, diethylene glycol monoethyl ether, diethylene glycol mono-n-butyl ether, phenoxyethanol and benzyl alcohol and mixtures thereof.
  • the pH of the compositions according to the invention can be adjusted within a wide range by suitable ingredients such as acidifying agent or alkalizing agent.
  • Oxidative dyeing of the fibers can in principle be carried out with atmospheric oxygen in the presence of oxidation dye precursors.
  • a chemical oxidizing agent is used, especially if, in addition to the coloring, a lightening effect on human hair is desired. This lightening effect may be desired regardless of the staining method.
  • the presence of oxidation dye precursors is therefore not a mandatory requirement for the use of oxidizing agents in the compositions of the invention.
  • Suitable oxidizing agents are persulfates, chlorites and in particular hydrogen peroxide or its addition products of urea, melamine and sodium borate.
  • the oxidation colorant can also be applied to the hair together with a catalyst which promotes the oxidation of the dye precursors, e.g. by atmospheric oxygen, activated.
  • catalysts are e.g. 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 2+ and Al 3+ . 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.
  • Suitable enzymes include peroxidases, which can significantly enhance the effect of small amounts of hydrogen peroxide. Furthermore, such enzymes are according to the invention suitable, which directly oxidize the oxidation dye precursors with the aid of atmospheric oxygen, such as the laccases, or in situ produce small amounts of hydrogen peroxide 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
  • Lactate oxidase and lactic acid and their salts Lactate oxidase and lactic acid and their salts
  • the actual colorant is expediently prepared immediately before use by mixing the preparation of the oxidizing agent with the preparation containing the compounds of the formula (Ia) and optionally dye precursors.
  • the resulting ready-to-use hair dye preparation should preferably have a pH in the range of 6 to 12. Particularly preferred is the use of the hair dye in a weakly alkaline medium.
  • the application temperatures can range between 15 and 40 ° C.
  • the hair dye is removed by rinsing of the hair to be dyed. The washing with a shampoo is omitted if a strong surfactant-containing carrier, e.g. a dyeing shampoo was used.
  • an agent according to the invention may optionally be applied to the hair with additional dye precursors but also without prior mixing with the oxidation component. After an exposure time of 20 to 30 minutes, the oxidation component is then applied, if appropriate after an intermediate rinse. After a further exposure time of 10 to 20 minutes, the product is then rinsed and, if desired, shampooed again.
  • the corresponding agent is adjusted to a pH of about 4 to 7.
  • an air oxidation is initially desired, wherein the applied agent preferably has a pH of 7 to 10.
  • the use of acidified peroxide is sulfate solutions may be preferred as the oxidizing agent.
  • compositions of the invention are mixed immediately before application with a hydrogen peroxide solution.
  • concentration of this hydrogen peroxide solution is determined on the one hand by the legal requirements and on the other hand by the desired effect; As a rule, 6-12% solutions in water are used.
  • the proportions of dyeing and / or lightening agent and hydrogen peroxide solution are usually in the range 1: 1 to 1: 2, with an excess of hydrogen peroxide solution is chosen in particular when no too pronounced Blondier Stil is desired.
  • compositions according to the invention comprise one or more substances from the group nitrilotriacetic acid (NTA), diethylenetriamine pentaacetic acid (DTPA), ethylenediamine disuccinic acid (EDDS), ethylenediamine diglutaric acid (EDGA), 2-hydroxypropylenediamine disuccinic acid (HPDS), glycinamide- ⁇ , ⁇ '-disuccinic acid (GADS).
  • NTA nitrilotriacetic acid
  • DTPA diethylenetriamine pentaacetic acid
  • EDDS ethylenediamine disuccinic acid
  • EDGA 2-hydroxypropylenediamine disuccinic acid
  • HPDS 2-hydroxypropylenediamine disuccinic acid
  • GDS glycinamide- ⁇ , ⁇ '-disuccinic acid
  • Ethylenediamine-N-N'-diglutaric acid EDDG
  • HPDDS 2-hydroxypropylenediamine-N-N'-dis
  • EDC diaminoalkyldi (sulfosuccinic acid)
  • DDS diaminoalkyldi (sulfosuccinic acid)
  • EPDHA ethylenediamine-N-N'-bis (ortho-hydroxyphenylacetic acid
  • N-2-hydroxyethyl-N, N-diacetic acid glyceryliminodiacetic acid
  • N-2-hydroxypropylsulfonic acid lminodiacetic acid
  • Aspartic acid-N-carboxymethyl-N-2,5-hydroxypropyl-3-sulfonic acid 8-alanine-N, N'-diacetic acid, aspartic acid-N, N'-diacetic acid, aspartic acid-N-monoacetic acid, dipicolinic acid, 1-hydroxyethane 1, 1-diphosphonate (HEDP) and their salts and / or derivatives.
  • HEDP 1-hydroxyethane 1, 1-diphosphonate
  • Preferred agents according to the invention are formulated with little or no water.
  • Particularly preferred agents according to the invention are characterized in that they contain less than 5% by weight, preferably less than 2% by weight, more preferably less than 1% by weight and in particular less than 0.5% by weight of water, preferred agents being anhydrous.
  • the water content of the agents can be determined, for example, by means of titration according to Karl Fischer.
  • a second object of the present invention is a process for the color change of keratin fibers, in particular human hair, in which
  • a pretreatment agent M1 is applied to the fiber, then a means M2 is applied to the fiber, optionally adding a further agent M3 to the means M2 before use,
  • this agent M2 is rinsed from the fiber after 5-30 minutes
  • an aftertreatment agent M4 is applied to the fiber and rinsed off after a contact time of a few minutes, at least one of the agents M1, M2 or M3 being an agent according to the invention.
  • the agents according to the invention can be formulated as single-component agents (color-modifying agent M2), as two-component agents (M2 + M3) or as three-component agents (M2 + M3 + M4) and used accordingly. Separation into multicomponent systems is particularly suitable where incompatibilities of the ingredients are to be expected or feared; the agent to be used is produced in such systems by the consumer directly before use by mixing the components. According to the invention, it is particularly preferred if the agent is formulated as a one-component agent which acts on the hair without pre- or post-treatment. In this case, the agent according to the invention can be applied to both wet and dry hair.
  • the strands (Kerling Euronaturhaar, blond, 12cm long) were treated with a watery
  • Texapon ® NSO solution (3 wt .-% active matter content, pH 6-7) thorough cleaning. Subsequently, the combing forces were determined before the product application as a reference value.
  • the recipes were applied in a ratio of 4g cream: 1g hair on the strands. After a contact time of 20 minutes at 32 ° C, the hair was rinsed with 32 ° C warm tap water for 2 minutes (flow 0.51 water per minute). Aftertreatment was not carried out.
  • the fibers After tinting with an agent according to the invention (formulation B), the fibers have improved wet combability, which manifests itself in the fact that less work has to be expended for combing the strands.
  • formulation B After tinting with an agent according to the invention (formulation B), the fibers have improved wet combability, which manifests itself in the fact that less work has to be expended for combing the strands.
  • the addition of Polyquaternium-6 the wet combability of the tress even further improved (corresponding to a significantly reduced required combing work).

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Abstract

L'invention concerne un agent destiné à modifier la couleur de fibres kératiniques, contenant, dans un excipient cosmétiquement acceptable, au moins un colorant et/ou un précurseur de colorant comme le 1,3-butanediol.
PCT/EP2010/064969 2009-10-30 2010-10-07 Agent de coloration Ceased WO2011051087A1 (fr)

Applications Claiming Priority (2)

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DE200910046196 DE102009046196A1 (de) 2009-10-30 2009-10-30 Tönungsmittel
DE102009046196.5 2009-10-30

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Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3986825A (en) * 1972-06-29 1976-10-19 The Gillette Company Hair coloring composition containing water-soluble amino and quaternary ammonium polymers
EP0998908A2 (fr) 1998-11-04 2000-05-10 L'oreal Composition tinctoriale contenant un colorant direct cationique et une pyrazolo-(1,5-a)-pyrimidine à titre de base d'oxydation, et procédés de teinture
WO2000069400A1 (fr) * 1999-05-12 2000-11-23 Wella Aktiengesellschaft Colorant d'oxydation pour les cheveux
EP1118319A1 (fr) * 2000-01-07 2001-07-25 Kao Corporation Soin pour cheveux teints
EP1627627A1 (fr) * 2004-05-28 2006-02-22 L'oreal Composition pour le traitement de matières kératiniques comprenant un composé polycarboxylique particulier et un polymère cationique et procédés la mettant en oeuvre
WO2006136303A1 (fr) * 2005-06-20 2006-12-28 Henkel Kommanditgesellschaft Auf Aktien Agents de soins capillaires
EP2033625A1 (fr) * 2006-06-07 2009-03-11 Kao Corporation Composition de colorant capillaire mono-composant
EP2065074A2 (fr) * 2007-11-09 2009-06-03 L'Oréal Composition de teinture d'oxydation des fibres kératiniques comprenant une cellulose à substituant(s) hydrophobe(s), un colorant d'oxydation et un polymère cationique
WO2010140542A1 (fr) * 2009-06-01 2010-12-09 ホーユー 株式会社 Composition cosmétique capillaire

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3986825A (en) * 1972-06-29 1976-10-19 The Gillette Company Hair coloring composition containing water-soluble amino and quaternary ammonium polymers
EP0998908A2 (fr) 1998-11-04 2000-05-10 L'oreal Composition tinctoriale contenant un colorant direct cationique et une pyrazolo-(1,5-a)-pyrimidine à titre de base d'oxydation, et procédés de teinture
WO2000069400A1 (fr) * 1999-05-12 2000-11-23 Wella Aktiengesellschaft Colorant d'oxydation pour les cheveux
EP1118319A1 (fr) * 2000-01-07 2001-07-25 Kao Corporation Soin pour cheveux teints
EP1627627A1 (fr) * 2004-05-28 2006-02-22 L'oreal Composition pour le traitement de matières kératiniques comprenant un composé polycarboxylique particulier et un polymère cationique et procédés la mettant en oeuvre
WO2006136303A1 (fr) * 2005-06-20 2006-12-28 Henkel Kommanditgesellschaft Auf Aktien Agents de soins capillaires
EP2033625A1 (fr) * 2006-06-07 2009-03-11 Kao Corporation Composition de colorant capillaire mono-composant
EP2065074A2 (fr) * 2007-11-09 2009-06-03 L'Oréal Composition de teinture d'oxydation des fibres kératiniques comprenant une cellulose à substituant(s) hydrophobe(s), un colorant d'oxydation et un polymère cationique
WO2010140542A1 (fr) * 2009-06-01 2010-12-09 ホーユー 株式会社 Composition cosmétique capillaire

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