US5073174A
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US
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Dyeing process employing indole dyes and oxidation dye precursors and dyeing agents employed
Assignee: L'Oréal SA
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Filing: 1990-07-20
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Granted: 1991-12-17
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Expires: 2010-07-20
Abstract
Abstract A process for dyeing keratinous fibers comprises a two-step operation in which in the first step the fibers are contacted with an indole dye in a medium suitable for dyeing the fibers, the medium being free from any oxidation catalyst and oxidation catalyst. Thereafter, in the second step the fibers are contacted with a para type oxidation dye precursor in a medium which is also suitable for dyeing the fibers and is free from any oxidation catalyst and oxidation agent. A multi-compartment kit housing the indole dye and para type oxidation dye precursor is also provided.
Inventors
- 👤 Charles Vayssie
- 👤 Daniel Bauer
- 👤 Francoise Richard
- 👤 Alex Junino
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 13:12
CPC Classifications
A; A61; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/49; A61K8/4906; A61K8/4913; A61K8/492; A61Q; A61Q5/00; A61Q5/10
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
417 words
A process for dyeing keratinous fibers comprising applying to said fibers, in a first step, a composition (A) containing, in a medium suitable for dyeing said fibers and free from any oxidation catalyst and oxidation agent, at least one indole dye having the formula ##STR3## wherein R 1 represents hydrogen, lower alkyl or --SiR 6 R 7 R 8 , R 2 and R 3 , each independently, represent hydrogen, lower alkyl, carboxyl, (lower alkoxy) carbonyl or --COOSiR 6 R 7 R 8 , R 4 and R 5 , each independently, represent hydrogen, linear or branched C 1 -C 20 alkyl, formyl, linear or branched C 2 -C 20 acyl, linear or branched C 3 -C 20 alkenoyl, --SiR 6 R 7 R 8 , --P(O)(OR 9 ) 2 or --SO 2 OR 9 , or R 4 and R 5 together with the oxygen atoms to which they are attached form a ring optionally containing a carbonyl group, a methylene group a thiocarbonyl group, a <P(O)OR 9 group or a <CR 10 R 11 group, R 9 and R 10 represent hydrogen, or lower alkyl, R 11 represents lower alkoxy, monoalkylamino or dialkylamino, R 6 , R 7 and R 8 , each independently, represent linear or branched lower alkyl, and the acid addition salt with an inorganic or organic acid, and the corresponding alkali metal, alkaline earth metal or amine salt; said indole dye being present in said composition (A) in an amount ranging from 0.1 to 5 percent by weight; relative to the total weight of said composition (A), and in a second step, applying to said fibers a composition (B) containing, in a medium suitable for dyeing said fibers and free from any oxidation catalyst and oxidation agent, (i) at least one para oxidation dye precursor selected from the group consisting of a paraphenylenediamine, a paraaminophenol and a heterocyclic para base selected from the group consisting of a pyridine derivative and a pyrimidine derivative or (ii) at least one rapid oxidation dye selected from the group consisting a trihydroxylated benzene derivative, diaminohydroxybenzene, aminodihydroxybenzene, a substituted aminohydroxybenzene, triaminobenzene, a substituted 1,2-dihydroxybenzene, brazilin, haematoxylin and alkanet extract or both (i) and (ii), said para oxidation dye precursor or said rapid oxidation dye or both being present in said composition (B) in an amount ranging from 0.05 to 3 percent by weight relative to the total weight of said composition (B), said composition (B) optionally being mixed at the time of use with hydrogen peroxide.
Claim 2
Dependent Claim
417 words
A process for dyeing keratinous fibers comprising applying to said fibers, in a first step, a composition (A) containing, in a medium suitable for dyeing said fibers and free from any oxidation catalyst and oxidation agent, at least one indole dye having the formula ##STR3## wherein R 1 represents hydrogen, lower alkyl or --SiR 6 R 7 R 8 , R 2 and R 3 , each independently, represent hydrogen, lower alkyl, carboxyl, (lower alkoxy) carbonyl or --COOSiR 6 R 7 R 8 , R 4 and R 5 , each independently, represent hydrogen, linear or branched C 1 -C 20 alkyl, formyl, linear or branched C 2 -C 20 acyl, linear or branched C 3 -C 20 alkenoyl, --SiR 6 R 7 R 8 , --P(O)(OR 9 ) 2 or --SO 2 OR 9 , or R 4 and R 5 together with the oxygen atoms to which they are attached form a ring optionally containing a carbonyl group, a methylene group a thiocarbonyl group, a <P(O)OR 9 group or a <CR 10 R 11 group, R 9 and R 10 represent hydrogen, or lower alkyl, R 11 represents lower alkoxy, monoalkylamino or dialkylamino, R 6 , R 7 and R 8 , each independently, represent linear or branched lower alkyl, and the acid addition salt with an inorganic or organic acid, and the corresponding alkali metal, alkaline earth metal or amine salt; said indole dye being present in said composition (A) in an amount ranging from 0.1 to 5 percent by weight; relative to the total weight of said composition (A), and in a second step, applying to said fibers a composition (B) containing, in a medium suitable for dyeing said fibers and free from any oxidation catalyst and oxidation agent, (i) at least one para oxidation dye precursor selected from the group consisting of a paraphenylenediamine, a paraaminophenol and a heterocyclic para base selected from the group consisting of a pyridine derivative and a pyrimidine derivative or (ii) at least one rapid oxidation dye selected from the group consisting a trihydroxylated benzene derivative, diaminohydroxybenzene, aminodihydroxybenzene, a substituted aminohydroxybenzene, triaminobenzene, a substituted 1,2-dihydroxybenzene, brazilin, haematoxylin and alkanet extract or both (i) and (ii), said para oxidation dye precursor or said rapid oxidation dye or both being present in said composition (B) in an amount ranging from 0.05 to 3 percent by weight relative to the total weight of said composition (B), said composition (B) optionally being mixed at the time of use with hydrogen peroxide.
Claim 3
Dependent Claim
20 words
Process according to claim 1, wherein a rinsing of the treated fibres is performed after application of the composition (A).
Claim 4
Dependent Claim
24 words
Process according to claim 2, wherein this rinsing is followed by a step of drying the hair before the application of the composition (B).
Claim 5
Dependent Claim
30 words
Process according to claim 1, wherein the indole dyes of the formula (I) are selected from 5,6-dihydroxyindole, 2-methyl-5,6-dihydroxyindole, 5-methoxy-6-hydroxyindole, (5 or 6)-acetoxy-(6 or 5)-hydroxyindole, 2-carboxy-5,6-dihydroxyindole, 3-methyl5,6-dihydroxyindole, 2,3-dimethyl-5,6-dihydroxyindole and their salts.
Claim 6
Dependent Claim
142 words
Process according to claim 1, wherein the paraphenylenediamines correspond to the formula (II): ##STR4## in which: R 12 , R 13 and R 14 , which may be identical or different, denote a hydrogen atom or halogen atom, a lower alkyl radical or a lower alcoxy radical; R 15 and R 16 , which may be identical or different, denote a hydrogen atom or a lower alkyl, lower hydroxyalkyl, lower alkoxyalkyl, lower carbamylakyl, lower sulphoalkyl, lower mesylaminoalkyl, lower acetylaminoalkyl, lower ureidoalkyl, lower carbethoxyaminoalkyl, lower piperidinoalkyl or lower morpholinoalkyl group, or alternatively R 15 and R 16 , together with the atom to which they are attached, form a piperidino or morpholino heterocycle, with the proviso that R 12 and R 14 represent a hydrogen atom when R 15 and R 16 do not represent a hydrogen atom; as well the corresponding salts.
Claim 7
Dependent Claim
45 words
Process according to claim 1, where the para-phenylenediamines are selected from the p-phenylenediamine, p-toluenediamine, methoxy-para-phenylenediamine, chloro-para-phenylenediamine, 2,6-dimethyl-p-phenylenediamine, 2,5-dimethyl-para-phenylenediamine, 2-methyl-5-methoxy-para-phenylenediamine, 2,6-dimethyl-5-methoxy-para-phenylenediamine, N,N-dimethyl-para-phenylenediamine, 3-methyl-4-amino-N,N-diethylaniline, N,N-bis(β-hydroxyethyl)-para-phenylenediamine, 3-methyl-4-amino-N,N-bis(β-hydroxyethyl)aniline, 3-chloro-4-amino-N,N-bis(β-hydroxymethyl)aniline, 4-amino-N-ethyl-N-(carbamylmethyl)aniline, 3-methyl-4-amino-N-ethyl-N-(carbamylmethyl)aniline, 4-amino-N-ethyl-N-(β-piperidinoethyl)aniline, 3-methyl-4-amino-N-ethyl-N-(β-piperidinoethyl)aniline, 4-amino-N-ethyl-N-(β-morpholinoethyl)aniline, 3-methyl-4-amino-N-ethyl-N-(β-morpholinoethyl)aniline, 4-amino-N-ethyl-N-(β-acetylaminoethyl)aniline, 4-amino-N-(β-methoxyethyl)aniline, 3-methyl-4-amino-N-ethyl-N-(β-acetylaminoethyl)aniline, 4-amino-N-ethyl-N-(β-mesylaminoethyl)aniline, 3-methyl-4-amino-N-ethyl-N-(β-mesylaminoethyl)aniline, 4-amino-N-ethyl-N-(β-sulphoethyl)aniline, 3-methyl-4-amino-N-ethyl-N-(β-sulphoethyl)aniline, N-(4-aminophenyl)morpholine, N-(4aminophenyl)piperidine, 2,3-dimethyl-p-phenylenediamine, isopropyl-p-phenylenediamine and their salts.
Claim 8
Dependent Claim
25 words
Process according to claim 1, wherein the paraaminophenols are selected from para-aminophenol, N-methyl-p-aminophenol, 2-methyl-4-aminophenol, 3-methyl-4-aminophenol, 2-chloro-4-aminophenol, 3-chloro-4-aminophenol, 2,6-dimethyl-4-amino-phenol, 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 and 3-methoxy-4-aminophenol.
Claim 9
Dependent Claim
18 words
Process according to claim 1, wherein the heterocyclic para oxidation dyes are selected from 2,5-diaminopyridine, 2-hydroxy-5-aminopyridine and tetraaminoprimidine.
Claim 10
Dependent Claim
31 words
Process according to claim 1, wherein the "rapid" oxidation dye is selected from 1,2,4-trihydroxybenzene, 1,2,4-trihydroxy-5-(C 1 -C6alkyl)benzene, 4-aminoresorcinol, 1,2,3-trihydroxybenzene, 4-methyl-1,2-dihydroxybenzene,2-amino-1,4-dihydroxybenzene, 2-amino-4-methoxyphenol, 2,4-diamino-phenol, 3-methoxy-1,2-dihydroxybenzene, 1,4-dihydroxy-2-(N,N-diethylamino)benzene, 2,5-diamino-4-methoxy-1-hydroxybenzene, 4,6-dimethoxy-3-amino-1-hydroxybenzene, 2,6-dimethyl-4-[N-(p-hydroxyphenyl)amino]-1-hydroxy-benzene, 1,5-diamino-2-methyl-4-[N-(p-hydroxyphenyl)-amino]benzene and their salts.
Claim 11
Dependent Claim
22 words
Process according to claim 1, wherein the medium suitable for dyeing is an aqueous medium consisting of water or a water/solvent(s) mixture.
Claim 12
Dependent Claim
17 words
Process according to claim 1, wherein the pH of the composition (A) is between 4 and 11.
Claim 13
Dependent Claim
17 words
Process according to claim 1, wherein the pH of the composition (B) is between 7 and 12.
Claim 14
Dependent Claim
29 words
Process according to claim 1, wherein the composition (B) contains, in addition, a coupler in proportions not exceeding 3% by weight relative to the total weight of the composition.
Claim 15
Dependent Claim
24 words
Process according to claim 1, wherein the aqueous medium contains up to 30% of solvent selected from alcohols, glycols, glycol ethers and methyl lactate.
Claim 16
Dependent Claim
29 words
Process according to claim 1, wherein the compositions (A) and/or (B) are presented in the form of a lotion, thickened or other wise, a gel or an aerosol mousse.
Claim 17
Dependent Claim
31 words
Process according to claim 1, wherein the composition (A) applied in a first stage is maintained in contact with the air for a period of between 1 minute and 60 minutes.
Claim 18
Dependent Claim
51 words
Process according to claim 1, wherein the composition (B) is applied in the second stage on the fibres treated with the composition (A), either immediately after the application of the latter, or postponing the second stage for a lapse of time which can vary between a few minutes and several days.
Claim 19
Dependent Claim
26 words
Process according to claim 17, wherein the composition (B) is maintained in contact with the hair for a period of between 1 minute and 60 minutes.
Claim 20
Dependent Claim
394 words
A keratinous fiber multi-compartment kit comprising a first compartment containing a composition (A) containing, in a medium suitable for dyeing said fiber and free from any oxidation catalyst and oxidation agent, at least one indole dye having the formula ##STR5## wherein R 1 represents hydrogen, lower alkyl or --SiR 6 R 7 R 8 , R 2 and R 3 , each independently, represent hydrogen, lower alkyl, carboxyl, (lower alkoxy) carbonyl or --COOSiR 6 R 7 R 8 , R 4 and R 5 , each independently, represent hydrogen, linear or branched C 1 -C 20 alkyl, formyl, linear or branched C 2 -C 20 acyl, linear or branched C 3 -C 20 alkenoyl, --SiR 6 R 7 R 8 , --P(O)(OR 9 ) 2 or --SO 2 OR 9 , or R 4 and R 5 together with the oxygen atoms to which they are attached form a ring optionally containing a carbonyl group, a methylene group a thiocarbonyl group, a <P(O)OR 9 group or a <CR 10 R 11 group, R 9 and R 10 represent hydrogen, or lower alkyl, R 11 represents lower alkoxy, monoalkylamino or dialkylamino, R 6 , R 7 and R 8 , each independently, represent linear or branched lower alkyl, and the acid addition salt with an inorganic or organic acid, and the corresponding alkali metal, alkaline earth metal or amine salt; said indole dye being present in said composition (A) in an amount ranging from 0.1 to 5 percent by weight; relative to the total weight of said composition (A), and a second compartment containing a composition (B) containing, in a medium suitable for dyeing said fibers and free from any oxidation catalyst and oxidation agent, (i) at least one para oxidation dye precursor selected from the group consisting of a paraphenylenediamine, a paraaminophenol and a heterocyclic para base selected from the group consisting of a pyridine derivative and a pyrimidine derivative or (ii) at least one rapid oxidation dye selected from the group consisting a trihydroxylated benzene derivative, diaminohydroxybenzene, aminodihydroxybenzene, a substituted aminohydroxybenzene, triaminobenzene, a substituted 1,2-dihydroxybenzene, brazilin, haematoxylin and alkanet extract or both (i) and (ii), said para oxidation dye precursor or said rapid oxidation dye or both being present in said composition (B) in an amount ranging from 0.05 to 3 percent by weight relative to the total weight of said composition (B).
Claim 21
Dependent Claim
394 words
A keratinous fiber multi-compartment kit comprising a first compartment containing a composition (A) containing, in a medium suitable for dyeing said fiber and free from any oxidation catalyst and oxidation agent, at least one indole dye having the formula ##STR5## wherein R 1 represents hydrogen, lower alkyl or --SiR 6 R 7 R 8 , R 2 and R 3 , each independently, represent hydrogen, lower alkyl, carboxyl, (lower alkoxy) carbonyl or --COOSiR 6 R 7 R 8 , R 4 and R 5 , each independently, represent hydrogen, linear or branched C 1 -C 20 alkyl, formyl, linear or branched C 2 -C 20 acyl, linear or branched C 3 -C 20 alkenoyl, --SiR 6 R 7 R 8 , --P(O)(OR 9 ) 2 or --SO 2 OR 9 , or R 4 and R 5 together with the oxygen atoms to which they are attached form a ring optionally containing a carbonyl group, a methylene group a thiocarbonyl group, a <P(O)OR 9 group or a <CR 10 R 11 group, R 9 and R 10 represent hydrogen, or lower alkyl, R 11 represents lower alkoxy, monoalkylamino or dialkylamino, R 6 , R 7 and R 8 , each independently, represent linear or branched lower alkyl, and the acid addition salt with an inorganic or organic acid, and the corresponding alkali metal, alkaline earth metal or amine salt; said indole dye being present in said composition (A) in an amount ranging from 0.1 to 5 percent by weight; relative to the total weight of said composition (A), and a second compartment containing a composition (B) containing, in a medium suitable for dyeing said fibers and free from any oxidation catalyst and oxidation agent, (i) at least one para oxidation dye precursor selected from the group consisting of a paraphenylenediamine, a paraaminophenol and a heterocyclic para base selected from the group consisting of a pyridine derivative and a pyrimidine derivative or (ii) at least one rapid oxidation dye selected from the group consisting a trihydroxylated benzene derivative, diaminohydroxybenzene, aminodihydroxybenzene, a substituted aminohydroxybenzene, triaminobenzene, a substituted 1,2-dihydroxybenzene, brazilin, haematoxylin and alkanet extract or both (i) and (ii), said para oxidation dye precursor or said rapid oxidation dye or both being present in said composition (B) in an amount ranging from 0.05 to 3 percent by weight relative to the total weight of said composition (B).
References Cited (Backward Citations)
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