EP0424261B1
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EP
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Dyeing composition containing oxidation dyes precursors and aminoindole derivatives as coupling agent
Assignee: L'Oréal SA
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Filing: 1990-10-18
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Granted: 1996-01-03
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Expires: 2010-10-18
Abstract
Abstract Oxidation dyeing composition intended for use for dyeing keratinous fibres, especially human keratinous fibres, and in particular the hair, which contains, in a solvent medium suitable for dyeing these fibres, at least one para oxidation dye precursor or at least one ortho oxidation dye precursor and at least one heterocyclic coupler corresponding to the formula (I): <IMAGE> in which: R1 and R3, which may be identical or different, denote a hydrogen atom or a C1-C4 alkyl group; R2 denotes a hydrogen atom, a C1-C4 alkyl group, a carboxyl group or an alkoxycarbonyl group; at least one of the radicals R2 or R3 denoting hydrogen; R4 denotes a hydrogen atom or a C1-C4 alkyl or C1-C4 hydroxyalkyl or C2-C4 polyhydroxyalkyl group; the group NHR4 occupying positions 4, 6 or 7 of the benzene ring, as well as their salts.
Inventors
- 👤 Alex Junino
- 👤 Gérard Lang
- 👤 Jean Cotteret
- 👤 Jean-Jacques Vandenbossche
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-01 02:05
CPC Classifications
A; A61; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/49; A61Q; A61Q5/00; A61Q5/10; A61K8/4906; A61K8/4913; A61K8/492
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
136 words
Oxidation tinctorial composition intended to be used for dyeing keratinous fibres, in particular human keratinous fibres and especially hair, characterized in that it contains, in a solvent medium appropriate for dyeing these fibres, at least one para oxidation dye precursor, 6-methyl-1-hydroxy-2-aminobenzene and/or 4-methyl-1-amino-2-hydroxybenzene and at least one heterocyclic coupler corresponding to the formula (I): in which: R₁ and R₃, which may be identical or different, denote a hydrogen atom or a C₁-C₄ alkyl group; R₂ denotes a hydrogen atom, a C₁-C₄ alkyl group, a carboxyl group or an alkoxycarbonyl group; at least one of the radicals R₂ or R₃ denoting hydrogen; R₄ denotes a hydrogen atom or a C₁-C₄ alkyl or C₁-C₄ hydroxyalkyl or C₂-C₄ polyhydroxyalkyl group; the group NHR₄ occupying the positions 4, 6 or 7 of the benzene ring, as well as their salts.
Claim 2
Dependent Claim
29 words
Composition according to Claim 1, characterized in that the para oxidation dye precursors are chosen from para-phenylenediamines, para-aminophenols, para heterocyclic precursors derived from pyridine or pyrimidine, and double bases.
Claim 3
Dependent Claim
121 words
Composition according to Claim 2, characterized in that the para-phenylenediamines are chosen from the compounds corresponding to the formula (II): in which: R₅, R₆ and R₇, which may be identical or different, represent a hydrogen or halogen atom, an alkyl radical or an alkoxy radical; and R₈ and R₉, which may be identical or different, represent a hydrogen atom or an alkyl, hydroxyalkyl, alkoxyalkyl, carbamylalkyl, mesylaminoalkyl, acetylaminoalkyl, ureidoalkyl, carbalkoxyaminoalkyl, piperidinoalkyl or morpholinoalkyl radical; or R₈ and R₉ form, together with the nitrogen atom to which they are bonded, a piperidino or morpholino heterocycle, with the proviso that R₅ or R₇ represents a hydrogen atom when R₈ and R₉ do not represent a hydrogen atom; and also the salts of these compounds.
Claim 4
Dependent Claim
34 words
Composition according to any one of Claims 1 to 3, characterized in that the heterocyclic couplers of formula (I) are chosen from 6-aminoindole, 7-aminoindole, 6-N-β-hydroxyethylaminoindole, 6-N-β-hydroxyethylamino-1-methylindole, 6-methylaminoindole, 6-amino-N-methyl-indole, 6-amino-2-carboxyindole, 6-amino-3-methylindole, 6-amino-2-methylindole, 6-amino-2-ethoxycarbonylindole and 6-N(β,γ-dihydroxypropyl)aminoindole.
Claim 5
Dependent Claim
43 words
Composition according to Claim 3, characterized in that the para-phenylenediamines are chosen from p-phenylenediamine, p-toluylenediamine, methoxy-para-phenylenediamine, 2,6-dimethyl-p-phenylenediamine, 2,5-dimethyl-p-phenylenediamine, 2-methyl-5-methoxy-para-phenylenediamine, 2,6-dimethyl-5-methoxy-p-phenylenediamine, N,N-dimethyl-para-phenylenediamine, 3-methyl-4-amino-N,N-diethylaniline, N,N-di(β-hydroxyethyl)-para-phenylenediamine, 3-methyl-4-amino-N,N-di(β-hydroxyethyl)aniline, 3-chloro-4-amino-N,N-di(β-hydroxyethyl)aniline, 4-amino-N,N-(ethylcarbamylmethyl)aniline, 3-methyl-4-amino-N,N-(ethylcarbamylmethyl)aniline, 4-amino-N,N-(ethyl-β-piperidinoethyl)aniline, 3-methyl-4-amino-N,N-(ethyl-β-piperidinoethyl)aniline, 4-amino-N,N-(ethyl-β-morpholinoethyl)aniline, 3-methyl-4-amino-N,N-(ethyl-β-morpholinoethyl)aniline, 4-amino-N,N-(ethyl-β-acetylaminoethyl)aniline, 4-amino-N-(β-methoxy-ethyl)aniline, 3-methyl-4-amino-N,N-(ethyl-β-acetylaminoethyl)aniline, 4-amino-N,N-(ethyl-β-mesylaminoethyl)aniline, 3-methyl-4-amino-N,N-(ethyl-β-mesylaminoethyl)aniline,4-amino-N,N-(ethyl-β-sulphoethyl)aniline, 3-methyl-4-amino-N,N-(ethyl-β-sulphoethyl)aniline, N-[(4'-amino)phenyl]-morpholine and N-[(4'-amino)phenyl]piperidine and their salts.
Claim 6
Dependent Claim
28 words
Composition according to Claim 2, characterized in that the p-aminophenols are chosen from p-aminophenol, 2-methyl-4-aminophenol, 3-methyl-4-aminophenol, 2-chloro-4-aminophenol, 3-chloro-4-aminophenol, 2,6-dimethyl-4-aminophenol, 3,5-dimethyl-4-aminophenol, 2,3-dimethyl-4-aminophenol, 2,5-dimethyl-4-aminophenol, 2-hydroxymethyl-4-aminophenol, 2-(β-hydroxyethyl)-4-aminophenol, 2-methoxy-4-aminophenol, 3-methoxy-4-aminophenol and 2-methoxymethyl-4-aminophenol.
Claim 7
Dependent Claim
147 words
Composition according to Claim 2, characterized in that the so-called double bases are bis-phenylalkylenediamines corresponding to the formula: in which: Z₁ and Z₂, which may be identical or different, represent hydroxyl or NHR₃ groups, where R₃ denotes a hydrogen atom or a lower alkyl radical; R₁ and R₂, which may be identical or different, represent either hydrogen atoms or halogen atoms or alkyl groups; R represents a hydrogen atom or an alkyl, hydroxyalkyl or aminoalkyl group, in which the amino radical can be substituted; and Y represents a radical taken from the group comprising the following radicals: -(CH₂) n -, (CH₂) n ,-O-(CH₂) n ,-,-(CH₂) n ,-CHOH-(CH₂) n , -N-(CH₂) n ,-; n being an integer between 0 and 8 and n ' being an integer between 0 and 4, it being possible for this base to be in the form of its addition salts with acids.
Claim 8
Dependent Claim
21 words
Composition according to Claim 7, characterized in that the double bases are chosen from N,N'-bis(β-hydroxyethyl)-N,N'-bis(4'-aminophenyl)-1,3-diaminopropan2-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-methylaminophenyl)tetramethylenediamine and N,N'-bis(ethyl)-N,N'-bis(4'-amino-3'-methylphenyl)ethylenediamine.
Claim 9
Dependent Claim
56 words
Composition according to any one of Claims 1 to 8, characterized in that, in addition to the heterocyclic coupler corresponding to the formula (I), the composition contains other couplers known per se, such as meta-diphenols, meta-aminophenols, meta-phenylenediamines, meta-acylaminophenols, meta-ureidophenols, meta-carbalkoxyaminophenols, α-naphthol and couplers having an active methylene group, chosen from the β-ketone compounds and the pyrazolones.
Claim 10
Dependent Claim
37 words
Composition according to Claim 9, characterized in that the supplementary coupler is chosen from 2,4-dihydroxyphenoxyethanol, 2,4-dihydroxyanisole, metaaminophenol, resorcinol monomethyl ether, 2-methyl-5-aminophenol, 2-methyl-5-N-(β-hydroxyethyl)aminophenol, 2-methyl-5-N-(β-mesylaminoethyl)aminophenol, 2,6-dimethyl-3-aminophenol, 6-hydroxybenzomorpholine, 2,4-diaminoanisole, 2,4-diaminophenoxyethanol, 6-aminobenzomorpholine, 2-[N-(β-hydroxyethyl)-amino-4-amino]-phenoxyethanol, 2-amino-4-N-(β-hydroxyethyl)aminoanisole, 2,4-diaminophenyl β,γ-dihydroxypropyl ether, 2,4-diaminophenoxyethylamine and their salts.
Claim 11
Dependent Claim
33 words
Composition according to any one of Claims 1 to 10, characterized in that the composition also contains direct dyes chosen from azo or anthraquinone dyes or the nitro derivatives of the benzene series.
Claim 12
Dependent Claim
49 words
Composition according to any one of Claims 1 to 11, characterized in that the oxidation dye precursors of the para type and the couplers are present, as a whole, in the composition in proportions of from 0.3 to 7% by weight relative to the total weight of the composition.
Claim 13
Dependent Claim
38 words
Composition according to any one of Claims 1 to 12, characterized in that the composition contains the coupler of formula (I) in proportions of between 0.05 and 3.5% by weight relative to the total weight of the composition.
Claim 14
Dependent Claim
31 words
Composition according to any one of Claims 1 to 13, characterized in that the solvent medium appropriate for dyeing is aqueous and in that its pH is between 8 and 11.
Claim 15
Dependent Claim
50 words
Composition according to any one of Claims 1 to 14, characterized in that it also contains anionic, cationic, nonionic or amphoteric surfactants or their mixtures, in proportions of between 0.5 and 55% by weight, and preferably between 2 and 50% by weight, relative to the total weight of the composition.
Claim 16
Dependent Claim
40 words
Composition according to any one of Claims 1 to 15, characterized in that the composition contains organic solvents chosen from C₁-C₄ lower alkanols, glycerol, glycols or glycol ethers and aromatic alcohols in proportions of between 1 and 40% by weight.
Claim 17
Dependent Claim
34 words
Composition according to any one of Claims 1 to 16, characterized in that it also contains thickeners in proportions of between 0.1 and 5% by weight relative to the total weight of the composition.
Claim 18
Dependent Claim
34 words
Composition according to any one of Claims 1 to 17, characterized in that it also contains antioxidants in proportions of between 0.05 and 1.5% by weight relative to the total weight of the composition.
Claim 19
Dependent Claim
143 words
Method for dyeing keratinous fibres, characterized in that a para oxidation dye precursor 6-methyl-1-hydroxy-2-aminobenzene and/or 4-methyl-1-amino-2-hydroxybenzene and at least one coupler corresponding to the formula (I): in which: R₁ and R₃, which may be identical or different, denote a hydrogen atom or a C₁-C₄ alkyl group; R₂ denotes a hydrogen atom, a C₁-C₄ alkyl group, a carboxyl group or an alkoxycarbonyl group; R₄ denotes a hydrogen atom or a C₁-C₄ alkyl or C₁-C₄ hydroxyalkyl or C₂-C₄ polyhydroxyalkyl group; the group NHR₄ occupying the positions 4, 6 or 7 of the benzene ring, as well as their salts in a solvent medium appropriate for dyeing are applied to the keratinous fibres, in particular human keratinous fibres and especially hair, said precursor and coupler being mixed at the time of use with an oxidant in an amount sufficient to be able to develop a colouring.
Claim 20
Dependent Claim
39 words
Method according to Claim 19, characterized in that the mixture is kept in contact with the fibres for 10 to 40 minutes, and preferably 15 to 30 minutes, after which the fibres are rinsed, washed, rinsed again and dried.
Claim 21
Dependent Claim
76 words
Compound, characterized in that it corresponds to the formula: in which: R₁ and R₃, independently of one another, represent a hydrogen atom or a C₁-C₄ alkyl group; R₂ denotes hydrogen or a C₁-C₄ alkyl group or a carboxyl or alkoxycarbonyl group; and R₄ represents a C₁-C₄ alkyl, C₁-C₄ hydroxyalkyl or C₂-C₄ polyhydroxyalkyl group, NHR₄ occupying the positions 4, 6 or 7 and R₄ not being able to denote C₁-C₄ alkyl when NHR₄ is in position 4.
Claim 22
Dependent Claim
111 words
Use of the compound corresponding to the formula: in which: R₁ and R₃, which may be identical or different, denote a hydrogen atom or a C₁-C₄ alkyl group; R₂ denotes a hydrogen atom, a C₁-C₄ alkyl group, a carboxyl group or an alkoxycarbonyl group; at least one of the radicals R₂ or R₃ denoting hydrogen; R₄ denotes a hydrogen atom or a C₁-C₄ alkyl or C₁-C₄ hydroxyalkyl or C₂-C₄ polyhydroxyalkyl group; the group NHR₄ occupying the positions 4, 6 or 7 of the benzene ring, as well as their salts, as coupler in the oxidation dyeing of keratinous fibres using oxidation dye precursors of the para type or 6-methyl-1-hydroxy-2-aminobenzene and/or 4-methyl-1-amino-2-hydroxybenzene.
Claim 23
Dependent Claim
73 words
Method for dyeing keratinous fibres, characterized in that, in a first step, the para oxidation dye precursor or 6-methyl-1-hydroxy-2-aminobenzene and/or 4-methyl-1-amino-2-hydroxybenzene are applied for 10 to 40 minutes and then, in a second step, the coupler of formula (I) defined in Claim 1 is applied for 10 to 40 minutes, the oxidant being present in the composition applied in the second step or being applied to the fibres themselves during a third step.
Claim 24
Dependent Claim
131 words
Oxidation tinctorial composition intended to be used for dyeing keratinous fibres, in particular human keratinous fibres and especially hair, characterized in that it contains, in a solvent medium appropriate for dyeing these fibres, at least 6-methyl-1-hydroxy-2-aminobenzene or 4-methyl-1-amino-2-hydroxybenzene and at least one heterocyclic coupler corresponding to the formula (I): in which: R₁ and R₃, which may be identical or different, denote a hydrogen atom or a C₁-C₄ alkyl group; R₂ denotes a hydrogen atom, a C₁-C₄ alkyl group, a carboxyl group or an alkoxycarbonyl group; at least one of the radicals R₂ or R₃ denoting hydrogen; R₄ denotes a hydrogen atom or a C₁-C₄ alkyl or C₁-C₄ hydroxyalkyl or C₂-C₄ polyhydroxyalkyl group; the group NHR₄ occupying the positions 4, 6 or 7 of the benzene ring, as well as their salts.
Claim 25
Dependent Claim
183 words
Method for dyeing keratinous fibres, characterized in that at least 6-methyl-1-hydroxy-2-aminobenzene or 4-methyl-1-amino-2-hydroxybenzene and at least one heterocyclic coupler corresponding to the formula (I): in which: R₁ and R₃, which may be identical or different, denote a hydrogen atom or a C₁-C₄ alkyl group; R₂ denotes a hydrogen atom, a C₁-C₄ alkyl group, a carboxyl group or an alkoxycarbonyl group; at least one of the radicals R₂ or R₃ denoting hydrogen; R₄ denotes a hydrogen atom or a C₁-C₄ alkyl or C₁-C₄ hydroxyalkyl or C₂-C₄ polyhydroxyalkyl group; the group NHR₄ occupying the positions 4, 6 or 7 of the benzene ring, as well as their salts in a solvent medium appropriate for dyeing are applied to the keratinous fibres, in particular human keratinous fibres and especially hair, said precursor and coupler being mixed at the time of use with an oxidant in an amount sufficient to be able to develop a colouring, the mixture is kept in contact with the fibres for 10 to 40 minutes, and preferably 15 to 30 minutes, after which the fibres are rinsed, washed, rinsed again and dried.
References Cited (Backward Citations)
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