US5364414A
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Tinctorial composition for keratinous fibres containing oxidation dye precursors and aminoindole couplers, methods for dyeing using these compositions and new compounds
Assignee: L'Oréal SA
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Filing: 1992-07-22
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Granted: 1994-11-15
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Expires: 2012-07-22
Abstract
Abstract 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 or at least one ortho oxidation dye precursor and at least one heterocyclic coupler corresponding to the formula (I): <IMAGE> (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 denotes 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.
Inventors
- 👤 Gerard Lang
- 👤 Alex Junino
- 👤 Jean Cotteret
- 👤 Jean J. Vandenbossche
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 18:49
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
208 words
An oxidation tinctorial composition for dyeing keratinous fibers comprising, in a solvent medium suitable for dyeing said fibers, at least one para oxidation dye precursor, said para oxidation dye precursor being selected from the group consisting of a paraphenylenediamine, a para-aminophenol, a para heterocyclic precursor derived from an amino or hydroxy substituted pyridine or pyrimidine and a bis-phenylalkylenediamine, and at least one heterocyclic coupler having formula (I) ##STR8## wherein R 1 and R 3 , each independently, represent hydrogen or C 1 -C 4 alkyl, R 2 represents hydrogen, C 1 -C 4 alkyl, carboxyl or alkoxycarbonyl with the proviso that at least one of R 2 and R 3 represents hydrogen, R 4 represents hydrogen, C 1 -C 4 alkyl, C 1 -C 4 hydroxyalkyl or C 2 -C 4 polyhydroxyalkyl; and the NHR 4 group occupies positions 4, 6 or 7 of the benzene ring, or a salt thereof, said heterocyclic coupler being present in an amount ranging from 0.05 to 3.5 weight percent based on the total weight of said composition and said para oxidation dye precursor and said heterocyclic coupler, as a whole, being present in an amount ranging from 0.3 to 7 percent by weight based on the total weight of said composition.
Claim 2
Dependent Claim
208 words
An oxidation tinctorial composition for dyeing keratinous fibers comprising, in a solvent medium suitable for dyeing said fibers, at least one para oxidation dye precursor, said para oxidation dye precursor being selected from the group consisting of a paraphenylenediamine, a para-aminophenol, a para heterocyclic precursor derived from an amino or hydroxy substituted pyridine or pyrimidine and a bis-phenylalkylenediamine, and at least one heterocyclic coupler having formula (I) ##STR8## wherein R 1 and R 3 , each independently, represent hydrogen or C 1 -C 4 alkyl, R 2 represents hydrogen, C 1 -C 4 alkyl, carboxyl or alkoxycarbonyl with the proviso that at least one of R 2 and R 3 represents hydrogen, R 4 represents hydrogen, C 1 -C 4 alkyl, C 1 -C 4 hydroxyalkyl or C 2 -C 4 polyhydroxyalkyl; and the NHR 4 group occupies positions 4, 6 or 7 of the benzene ring, or a salt thereof, said heterocyclic coupler being present in an amount ranging from 0.05 to 3.5 weight percent based on the total weight of said composition and said para oxidation dye precursor and said heterocyclic coupler, as a whole, being present in an amount ranging from 0.3 to 7 percent by weight based on the total weight of said composition.
Claim 3
Dependent Claim
103 words
The composition of claim 1 wherein said paraphenylene diamine has the formula ##STR9## wherein R 5 , R 6 and R 7 , each independently, represent hydrogen, halogen, alkyl or alkoxy, and R 8 and R 9 , each independently, represent hydrogen, alkyl, hydroxyalkyl, alkoxyalkyl, carbamylalkyl, mesylaminoalkyl, acetylaminoalkyl, ureidoalkyl, carbalkoxyaminoalkyl, piperidinoalkyl, or morpholinoalkyl; or R 8 and R 9 together with the nitrogen atom to which they are attached form a piperidino or morpholino heterocycle, with the proviso that R 5 or R 7 represents hydrogen when R 8 and R 9 do not represent hydrogen; and the salts of said paraphenylene diamine.
Claim 4
Dependent Claim
31 words
The composition of claim 1 wherein said heterocyclic coupler of formula (I) is selected from the group consisting of 6-aminoindole, 7-aminoindole, 6-N-β-hydroxyethylaminoindole, 6-N-β-hydroxyethylamino-1-methylindole, 6-methylaminoindole, 6-amino-N-methylindole, 6-amino-2-carboxyindole, 6-amino-3-methylindole, 6-amino-2-methylindole, 6-amino-2-ethoxycarbonylindole and 6-N(β,γ-dihydoxypropyl)aminoindole.
Claim 5
Dependent Claim
55 words
The composition of claim 2 wherein said paraphenylene diamine is selected from the group consisting of p-phenylenediamine, p-toluylenediamine, methoxyparaphenylenediamine, 2,6-dimethyl-p-phenylenediamine, 2,5-dimethyl-p-phenylenediamine, 2-methyl-5-methoxy-paraphenylenediamine, 2,6-dimethyl-5-methoxy-paraphenylenediamine, N,N-dimethylparaphenyldiamine, 3-methyl-4-amino-N-diethylaniline, N,N-di(β-hydroxyethyl) paraphenylenediamine, 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-methoxyethyl)aniline, 3-methyl-4-amino-N,N(ethyl-β-acetylaminoethyl)aniline, 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 the salts thereof.
Claim 6
Dependent Claim
31 words
The composition of claim 1 wherein said paraaminophenol is selected from the group consisting of p-aminophenol, 2-methyl-4-aminophenol, 3-methyl-4-aminophenol, p0 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
119 words
The composition of claim 1 wherein said bis-phenylalkylenediamine has the formula ##STR10## wherein Z 1 and Z 2 , each independently, represent hydroxyl or NHR 3 wherein R 3 represents hydrogen or lower alkyl, R 1 and R 2 , each independently, represent hydrogen, halogen or alkyl, R represents hydrogen, alkyl, hydroxyalkyl or aminoalkyl wherein the amino moiety can be substituted, and Y represents a member selected from the group consisting of --(CH 2 ) n --, --(CH 2 ) n' --O--(CH 2 ) n' --, --(CH 2 ) n' --CHOH--, and ##STR11## wherein n is an integer ranging from 0 to 8, and n' is an integer ranging from 0 to 4, and the acid addition salt thereof.
Claim 8
Dependent Claim
23 words
The composition of claim 6 wherein said bis-phenylalkylenediamine is selected from the group consisting of N,N'-bis(β-hydroxyethyl)-N,N'-bis(4'-aminophenyl)-1,3-diaminopropan-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-methylaminophenyl)-tetramethylenediamine and N,N'-bis(ethyl)-N,N'-bis(4'-amino-3'-methylphenyl)-ethylenediamine.
Claim 9
Dependent Claim
55 words
The composition of claim 1 wherein in addition to said heterocyclic coupler of formula (I), said composition also contains another coupler selected from the group consisting of a meta-diphenol, a meta-aminophenol, a meta-phenylenediamine, a meta-acylaminophenol, a meta-ureidophenol, a meta-carbalkoxyaminophenol, α-naphthol, a coupler having an active methylene group selected from a β-ketone compound and a pyrazolone.
Claim 10
Dependent Claim
41 words
The composition of claim 8 wherein said another coupler is selected from the group consisting of 2,4-dihydroxyphenoxyethanol, 2,4-dihydroxyanisole, meta-aminophenol, resorcinol monomethyl ether, 2-methyl-5-aminophenol, 2-methyl-5-N-(β-hydroxyethyl)-aminophenol, 2-methyl-5-N-(β-methylaminoethyl)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-diaminophenoxyethyl amine, and a salt thereof.
Claim 11
Dependent Claim
31 words
The composition of claim 1 which also contains a direct dye selected from the group consisting of an azo dye, an anthraquinone dye and a nitro derivative of the benzene series.
Claim 12
Dependent Claim
26 words
The composition of claim 1 wherein said solvent medium suitable for dyeing said fibers is an aqueous medium having a pH ranging from 8 to 11.
Claim 13
Dependent Claim
125 words
The composition of claim 1 which also contains at least one of an anionic, cationic or amphoteric surfactant present in an amount ranging from 0.5 to 55 weight percent based on the total weight of said composition; an organic solvent selected from a C 1 -C 4 lower alkanol, glycerol, a glycol, a glycol ether or an aromatic alcohol, said organic solvent being present in an amount ranging from 1 to 40 weight percent based on the total weight of said composition; a thickener present in an amount ranging from 0.1 to 5 weight percent based on the total weight of said composition; and an antioxidant present in an amount ranging from 0.05 to 1.5 weight percent based on the total weight of said composition.
Claim 14
Independent Claim
236 words
A method for dyeing keratinous fibers comprising applying to said fibers an oxidation tinctorial composition comprising, in a solvent medium suitable for dyeing said fibers, at least one para oxidation dye precursor, said para oxidation dye precursor being selected from the group consisting of a paraphenylenediamine, a para-aminophenol, a para heterocyclic precursor derived from an amino or hydroxy substituted pyridine or pyrimidine and a bis-phenylalkylenediamine, and at least one heterocyclic coupler having formula (I) ##STR12## wherein R 1 and R 3 , each independently, represent hydrogen or C 1 -C 4 alkyl, R 2 represents hydrogen, C 1 -C 4 alkyl, carboxyl or alkoxycarbonyl, with the proviso that at least one of R 2 and R 3 represents hydrogen, R 4 represents hydrogen, C 1 -C 4 alkyl, C 1 -C 4 hydroxyalkyl or C 2 -C 4 polyhydroxyalkyl, the NHR 4 group occupies positions 4, 6 or 7 of the benzene ring, or a salt thereof, said heterocyclic coupler being present in an amount ranging from 0.05 to 3.5 weight percent based on the total weight of said composition and said para oxidation dye precursor and said heterocyclic coupler, as a whole, being present in an amount ranging from 0.3 to 7 percent by weight based on the total weight of said composition, said precursor and coupler being mixed at the time of use with an oxidant in an amount sufficient to develop a coloring.
Claim 15
Independent Claim
236 words
A method for dyeing keratinous fibers comprising applying to said fibers an oxidation tinctorial composition comprising, in a solvent medium suitable for dyeing said fibers, at least one para oxidation dye precursor, said para oxidation dye precursor being selected from the group consisting of a paraphenylenediamine, a para-aminophenol, a para heterocyclic precursor derived from an amino or hydroxy substituted pyridine or pyrimidine and a bis-phenylalkylenediamine, and at least one heterocyclic coupler having formula (I) ##STR12## wherein R 1 and R 3 , each independently, represent hydrogen or C 1 -C 4 alkyl, R 2 represents hydrogen, C 1 -C 4 alkyl, carboxyl or alkoxycarbonyl, with the proviso that at least one of R 2 and R 3 represents hydrogen, R 4 represents hydrogen, C 1 -C 4 alkyl, C 1 -C 4 hydroxyalkyl or C 2 -C 4 polyhydroxyalkyl, the NHR 4 group occupies positions 4, 6 or 7 of the benzene ring, or a salt thereof, said heterocyclic coupler being present in an amount ranging from 0.05 to 3.5 weight percent based on the total weight of said composition and said para oxidation dye precursor and said heterocyclic coupler, as a whole, being present in an amount ranging from 0.3 to 7 percent by weight based on the total weight of said composition, said precursor and coupler being mixed at the time of use with an oxidant in an amount sufficient to develop a coloring.
Claim 16
Dependent Claim
33 words
The method of claim 13 wherein the mixture of said composition and oxidant is permitted to remain in contact with said fibers for a period of time ranging from 10 to 40 minutes.
Claim 17
Dependent Claim
33 words
The method of claim 13 wherein the mixture of said composition and oxidant is permitted to remain in contact with said fibers for a period of time ranging from 15 to 30 minutes.
Claim 18
Independent Claim
267 words
A method for dyeing keratinous fibers comprising in a first step applying to said fibers a first composition comprising at least one para oxidation dye precursor in a solvent medium suitable for dyeing said fibers, said para oxidation dye precursor being selected from the group consisting of a paraphenylenediamine, a para-aminophenol, a para heterocyclic precursor derived from an amino or hydroxy substituted pyridine or pyrimidine and a bis-phenylalkylenediamine and permitting said first composition to remain in contact with said fibers for a period of time ranging from 10 to 40 minutes, and in a second step applying to said fibers a second composition comprising in a solvent medium suitable for dyeing said fibers, at least one heterocyclic coupler having formula (I) ##STR13## wherein R 1 and R 3 , each independently, represent hydrogen or C 1 -C 4 alkyl, R 2 represents hydrogen, C 1 -C 4 alkyl, carboxyl or alkoxycarbonyl with the proviso that at least one of R 2 and R 3 represents hydrogen, R 4 represents hydrogen, C 1 -C 4 alkyl, C 1 -C 4 hydroxyalkyl or C 2 -C 4 polyhydroxyalkyl; and the NHR 4 group occupies positions 4, 6 or 7 of the benzene ring, or a salt thereof, and permitting said second composition to remain in contact with said fibers for a period of time ranging from 10 to 40 minutes, said second composition optionally containing an oxidant in an amount effective to develop a coloring or alternatively in a third step applying to said fibers an oxidant in an amount and for a time effective to develop a coloring.
Claim 19
Independent Claim
267 words
A method for dyeing keratinous fibers comprising in a first step applying to said fibers a first composition comprising at least one para oxidation dye precursor in a solvent medium suitable for dyeing said fibers, said para oxidation dye precursor being selected from the group consisting of a paraphenylenediamine, a para-aminophenol, a para heterocyclic precursor derived from an amino or hydroxy substituted pyridine or pyrimidine and a bis-phenylalkylenediamine and permitting said first composition to remain in contact with said fibers for a period of time ranging from 10 to 40 minutes, and in a second step applying to said fibers a second composition comprising in a solvent medium suitable for dyeing said fibers, at least one heterocyclic coupler having formula (I) ##STR13## wherein R 1 and R 3 , each independently, represent hydrogen or C 1 -C 4 alkyl, R 2 represents hydrogen, C 1 -C 4 alkyl, carboxyl or alkoxycarbonyl with the proviso that at least one of R 2 and R 3 represents hydrogen, R 4 represents hydrogen, C 1 -C 4 alkyl, C 1 -C 4 hydroxyalkyl or C 2 -C 4 polyhydroxyalkyl; and the NHR 4 group occupies positions 4, 6 or 7 of the benzene ring, or a salt thereof, and permitting said second composition to remain in contact with said fibers for a period of time ranging from 10 to 40 minutes, said second composition optionally containing an oxidant in an amount effective to develop a coloring or alternatively in a third step applying to said fibers an oxidant in an amount and for a time effective to develop a coloring.
Claim 20
Dependent Claim
127 words
An oxidation tinctorial composition for dyeing keratinous fibers comprising, in a solvent medium suitable for dyeing said fibers, at least one para oxidation dye precursor, said para oxidation dye precursor being selected from the group consisting of a paraphenylenediamine, a para-aminophenol, a para heterocyclic precursor derived from an amino or hydroxy substituted pyridine or pyrimidine and a bis-phenylalkylenediamine and at least one heterocyclic coupler selected from the group consisting of 4-aminoindole, 6-aminoindole and 7-aminoindole present in an amount ranging from 0.05 to 3.5 weight percent based on the total weight of said composition and said para oxidation dye precursor and said heterocyclic precursor as a whole, being present in an amount ranging from 0.3 to 7 percent by weight based on the total weight of said composition.
Claim 21
Dependent Claim
127 words
An oxidation tinctorial composition for dyeing keratinous fibers comprising, in a solvent medium suitable for dyeing said fibers, at least one para oxidation dye precursor, said para oxidation dye precursor being selected from the group consisting of a paraphenylenediamine, a para-aminophenol, a para heterocyclic precursor derived from an amino or hydroxy substituted pyridine or pyrimidine and a bis-phenylalkylenediamine and at least one heterocyclic coupler selected from the group consisting of 4-aminoindole, 6-aminoindole and 7-aminoindole present in an amount ranging from 0.05 to 3.5 weight percent based on the total weight of said composition and said para oxidation dye precursor and said heterocyclic precursor as a whole, being present in an amount ranging from 0.3 to 7 percent by weight based on the total weight of said composition.
Claim 22
Dependent Claim
11 words
The composition of claim 17 wherein said heterocyclic coupler is 4-aminoindole.
Claim 23
Dependent Claim
11 words
The composition of claim 17 wherein said heterocyclic coupler is 7-aminoindole.
Claim 24
Dependent Claim
175 words
An oxidation tinctorial composition for dyeing keratinous fibers comprising, in a solvent medium suitable for dyeing said fibers, at least one para oxidation dye precursor, said para oxidation dye precursor being selected from the group consisting of a paraphenylenediamine, a para-aminophenol, a para heterocyclic precursor derived from an amino hydroxy substituted pyridine or pyrimidine and a bis-phenylalkylenediamine and at least one heterocyclic coupler having formula (I) ##STR14## wherein R 1 and R 3 represent hydrogen, R 2 represents hydrogen, R 4 represents hydrogen, C 1 -C 4 alkyl, C 1 -C 4 hydroxyalkyl or C 2 -C 4 polyhydroxyalkyl; and the NHR 4 group occupies positions 4, 6 or 7 of the benzene ring, or a salt thereof, said heterocyclic coupler being present in an amount ranging from 0.05 to 3.5 weight percent based on the total weight of said composition and said para oxidation dye precursor and said heterocyclic coupler, as a whole, being present in an amount ranging from 0.3 to 7 percent by weight based on the total weight of said composition.
Claim 25
Dependent Claim
175 words
An oxidation tinctorial composition for dyeing keratinous fibers comprising, in a solvent medium suitable for dyeing said fibers, at least one para oxidation dye precursor, said para oxidation dye precursor being selected from the group consisting of a paraphenylenediamine, a para-aminophenol, a para heterocyclic precursor derived from an amino hydroxy substituted pyridine or pyrimidine and a bis-phenylalkylenediamine and at least one heterocyclic coupler having formula (I) ##STR14## wherein R 1 and R 3 represent hydrogen, R 2 represents hydrogen, R 4 represents hydrogen, C 1 -C 4 alkyl, C 1 -C 4 hydroxyalkyl or C 2 -C 4 polyhydroxyalkyl; and the NHR 4 group occupies positions 4, 6 or 7 of the benzene ring, or a salt thereof, said heterocyclic coupler being present in an amount ranging from 0.05 to 3.5 weight percent based on the total weight of said composition and said para oxidation dye precursor and said heterocyclic coupler, as a whole, being present in an amount ranging from 0.3 to 7 percent by weight based on the total weight of said composition.
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