US4885006A
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Process for dyeing keratinous fibres with indole derivatives combined with an iodide
Assignee: L' O R E A L
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Filing: 1987-11-17
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Granted: 1989-12-05
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Expires: 2007-11-17
Abstract
Abstract Process for dyeing human keratinous fibres, consisting in applying on these fibres at least least one composition (A) containing, in a cosmetically acceptable medium, one or more indole derivatives corresponding to the formula (I) <IMAGE> (I) in which: R1 denotes a hydrogen atom, a lower C1-C6 lower akly group or a group -SiR9R10R11; R2 and R3, which may be identical or different, denote a hydrogen atom, a C1-C6 lower alkyl group, a carboxyl group, a lower alkoxycarbonyl group wherein the alkoxy moiety contains 1 to 6 carbon atoms, or a group -COOSiR9R10R11; R4 and R5, which may be identical or different, denote a hydrogen atom, a C1-C20 linear or branched alkyl group, a formyl group, a linear or branched C2-C20 acyl group, a linear or branched C3-C20 alkenoyl group, a group -SiR9R10R11, a group -P(O) (OR6)2 or a group R6OSO2-, or alternatively R4 and R5, together with the oxygen atoms to which they are attached, form a ring optionally containing a carbonyl group, a methylene group, a thiocarbonyl group or one of the following groups; >P(O)OR6, or >CR7R8; R6 and R7 denoting a hydrogen atom or C1-C6 lower alkyl group, R8 denoting a C1-C6 lower alkoxy group or a mono- or di-C1-C6 alkylamino group, R9,R10 and R11, which may be identical or different, denoting C1-C6 linear or branched alkyl groups, and the corresponding salts of alkali metals, alkaline-earth metals and amines, at least one of the radicals R1 to R5 being other than hydrogen, in combinations: either (a) with iodide ions, or (b) with a solution of hydrogen peroxide at a pH of between 3.5 and 7, the application of the composition (A) being preceded or followed by the application of composition (B) which contains, in a cosmetically acceptable medium, either (a) hydrogen peroxide at a pH of between 2 and 7 when the composition (A) contains iodide ions, or (b) iodide ions when the composition (A) contains hydrogen peroxide.
Inventors
- 👤 Jean F. Grollier
- 👤 Didier Garoche
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 00:04
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: 26
Claim 1
Independent Claim
430 words
A process for dyeing human keratinous fibers comprising applying to said fibers at least one composition (A) comprising, in a cosmetically acceptable medium at least one indole derivative having the formula ##STR4## wherein R 1 represents hydrogen, C 1 -C 6 lower alkyl or --SiR 9 R 10 R 11 , R 2 and R 3 , each independently, represent hydrogen, C 1 -C 6 lower alkyl, carboxyl, lower alkoxycarbonyl wherein the alkoxy moiety contains 1-6 carbon atoms or --COOSiR 9 R 10 R 11 , R 4 and R 5 , each independently, represent hydrogen, C 1 -C 20 linear or branched alkyl, formyl, linear or branched C 2 -C 20 acyl, linear or branched C 3 -C 20 alkenoyl, --SiR 9 R 10 R 11 , --P(O)(OR 6 ) 2 or R 6 OSO 2 --, or R 4 and R 5 together with the oxygen atoms to which they are attached form a ring containing or not a carbonyl group, a methylene group, a thiocarbonyl group, a >P(O)OR 6 group or a >CR 7 R 8 group, R 6 and R 7 represent hydrogen or C 1 -C 6 lower alkyl, R 8 represents C 1 -C 6 lower alkoxy, monoalkylamino wherein the alkyl moiety has 1-6 carbon atoms or dialkylamino wherein the alkyl moiety has 1-6 carbon atoms, R 9 , R 10 and R 11 , each independently, represent C 1 -C 6 linear or branched alkyl, with the proviso that at least one of R 1 -R 5 is other than hydrogen, the inorganic or organic acid addition salts of said indole and the corresponding alkali metal, alkaline earth metal and amine salts thereof, said indole being present in an amount ranging from 0.01 to 5 percent by weight based on the total weight of said composition, and (a) an iodide present in an amount ranging from 0.007 to 4 percent by weight based on the total weight of said composition and expressed as iodide ions, or (b) a solution of hydrogen peroxide at a concentration of 1-40 volumes, said composition (A) having a pH ranging from 3.5 to 7 when said cosmetically acceptable medium is water or a water solvent mixture, said composition (A) being applied to said human keratinous fibers either prior to or subsequent to the application to said keratinous fibers of a composition (B) comprising, in a cosmetically acceptable medium, (i) hydrogen peroxide solution at a pH ranging from 2 to 7 when said composition (A) contains said iodide, or (ii) said iodide when said composition (A) contains hydrogen peroxide.
Claim 2
Dependent Claim
430 words
A process for dyeing human keratinous fibers comprising applying to said fibers at least one composition (A) comprising, in a cosmetically acceptable medium at least one indole derivative having the formula ##STR4## wherein R 1 represents hydrogen, C 1 -C 6 lower alkyl or --SiR 9 R 10 R 11 , R 2 and R 3 , each independently, represent hydrogen, C 1 -C 6 lower alkyl, carboxyl, lower alkoxycarbonyl wherein the alkoxy moiety contains 1-6 carbon atoms or --COOSiR 9 R 10 R 11 , R 4 and R 5 , each independently, represent hydrogen, C 1 -C 20 linear or branched alkyl, formyl, linear or branched C 2 -C 20 acyl, linear or branched C 3 -C 20 alkenoyl, --SiR 9 R 10 R 11 , --P(O)(OR 6 ) 2 or R 6 OSO 2 --, or R 4 and R 5 together with the oxygen atoms to which they are attached form a ring containing or not a carbonyl group, a methylene group, a thiocarbonyl group, a >P(O)OR 6 group or a >CR 7 R 8 group, R 6 and R 7 represent hydrogen or C 1 -C 6 lower alkyl, R 8 represents C 1 -C 6 lower alkoxy, monoalkylamino wherein the alkyl moiety has 1-6 carbon atoms or dialkylamino wherein the alkyl moiety has 1-6 carbon atoms, R 9 , R 10 and R 11 , each independently, represent C 1 -C 6 linear or branched alkyl, with the proviso that at least one of R 1 -R 5 is other than hydrogen, the inorganic or organic acid addition salts of said indole and the corresponding alkali metal, alkaline earth metal and amine salts thereof, said indole being present in an amount ranging from 0.01 to 5 percent by weight based on the total weight of said composition, and (a) an iodide present in an amount ranging from 0.007 to 4 percent by weight based on the total weight of said composition and expressed as iodide ions, or (b) a solution of hydrogen peroxide at a concentration of 1-40 volumes, said composition (A) having a pH ranging from 3.5 to 7 when said cosmetically acceptable medium is water or a water solvent mixture, said composition (A) being applied to said human keratinous fibers either prior to or subsequent to the application to said keratinous fibers of a composition (B) comprising, in a cosmetically acceptable medium, (i) hydrogen peroxide solution at a pH ranging from 2 to 7 when said composition (A) contains said iodide, or (ii) said iodide when said composition (A) contains hydrogen peroxide.
Claim 3
Dependent Claim
90 words
The process of claim 1 wherein said indole has the formula ##STR5## wherein R' 2 and R' 3 , each independently, represent hydrogen, C 1 -C 6 lower alkyl, C 1 -C 6 carboxyl, lower alkoxy carbonyl wherein the alkoxy moiety contains 1-6 carbon atoms, R' 4 and R' 5 , each independently, represent hydrogen, C 1 -C 6 alkyl, C 2 -C 20 linear acyl, or trimethylsilyl, or R' 4 and R' 5 together with the oxygen atoms to which they are attached form a methylenedioxy or carbonyldioxy ring.
Claim 4
Dependent Claim
35 words
The process of claim 1 wherein said indole derivative is selected from the group consisting of 5-methoxy-6-hydroxyindole, 3-methyl-5,6-dihydroxyindole, 2-methyl-5,6-dihydroxyindole, 5,6-bis (trimethylsilyloxy) indole, 5-(or 6-) myristoyloxy-6-(or 5-) hydroxyindole, 5,6-(methylenedioxy) indole, 5-acetoxy-6-hydroxyindole, 2-ethoxycarbonyl-5,6-dihydroxyindole, 5-hydroxy-6-methoxyindole, 5,6-carbonyldioxyindole and 2-carboxy-5,6-dihydroxyindole.
Claim 5
Dependent Claim
22 words
The process of claim 1 wherein said iodide is an alkali metal iodide, an alkaline earth metal iodide or an ammonium iodide.
Claim 6
Dependent Claim
65 words
The process of claim 1 comprising, in a first stage, applying to said human keratinous fibers said composition (A) containing an iodide selected from the group consisting of an alkali metal iodide, an alkaline earth metal iodide or an ammonium iodide and at least one said indole derivative and, in a second stage applying to said human keratinous fibers, said composition (B) containing hydrogen peroxide.
Claim 7
Dependent Claim
29 words
The process of claim 1 wherein said human keratinous fibers are rinsed with water after the application of said composition (A) and before the application of said composition (B).
Claim 8
Dependent Claim
36 words
The process of claim 1 wherein said composition (A) and said composition (B) are permitted to remain in contact with said human keratinous fibers for a period of time ranging from ten seconds to 45 minutes.
Claim 9
Dependent Claim
25 words
The process of claim 1 wherein said composition (A) and said composition (B) are in the form of a gel, a cream or an emulsion.
Claim 10
Dependent Claim
53 words
The process of claim 1 wherein said cosmetically acceptable medium is water, a solvent selected from the group consisting of ethyl alcohol, isopropyl alcohol, tert. butyl alcohol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether and ethylene glycol monoethyl ether acetate, or a mixture of water and said solvent.
Claim 11
Dependent Claim
29 words
The process of claim 9 wherein said solvent is present in an amount ranging from 0.5 to 75 percent by weight based on the total weight of said composition.
Claim 12
Dependent Claim
33 words
The process of claim 1 wherein said cosmetically acceptable medium of said composition (B) containing said iodide is water or a solvent, water mixture and has a pH ranging from 3 to 11.
Claim 13
Dependent Claim
48 words
The process of claim 1 wherein one or both of said compositions (A) and (B) also contain at least one of an anionic, cationic, nonionic or amphoteric surfactant, present in an amount ranging from 0.1 to 50 percent by weight based on the total weight of said composition.
Claim 14
Dependent Claim
39 words
The process of claim 1 wherein one or both of said compositions (A) and (B) contain a thickening agent present in an amount ranging from 0.1 to 5 percent by weight based on the total weight of said composition.
Claim 15
Dependent Claim
320 words
A composition for dyeing human keratinous fibers comprising in a cosmetically acceptable medium at least one indole derivative having the formula ##STR6## wherein R 1 represents hydrogen, C 1 -C 6 alkyl or --SiR 9 R 10 R 11 , R 2 and R 3 , each independently, represent hydrogen, C 1 -C 6 lower alkyl, carboxyl, lower alkoxycarbonyl wherein the alkoxy moiety contains 1-6 carbon atoms or --COOSiR 9 R 10 R 11 , R 4 and R 5 , each independently, represent hydrogen, C 1 -C 20 linear or branched alkyl, formyl, linear or branched C 2 -C 20 acyl, linear or branched C 3 -C 20 alkenoyl, --SiR 9 R 10 R 11 , --P(O)(OR 6 ) 2 or R 6 OSO 2 --, or R 4 and R 5 together with the oxygen atoms to which they are attached form a ring containing or not a carbonyl group, a methylene group, a thiocarbonyl group, a >P(O)OR 6 group or a >CR 7 R 8 group, R 6 and R 7 represent hydrogen or C 1 -C 6 lower alkyl, R 8 represents C 1 -C 6 lower alkoxy, monoalkylamino wherein the alkyl moiety has 1-6 carbon atoms or dialkylamino wherein the alkyl moiety has 1-6 carbon atoms, R 9 , R 10 and R 11 , each independently, represent C 1 -C 6 linear or branched alkyl, with the proviso that at least one of R 1 -R 5 is other than hydrogen, the inorganic or organic acid addition salts of said indole and the corresponding alkali metal, alkaline earth metal and amine salts thereof, said indole being present in an amount ranging from 0.01 to 5 percent by weight based on the total weight of said composition, and an iodide present in an amount ranging from 0.007 to 4 percent by weight based on the total weight of said composition and expressed as iodide ions.
Claim 16
Dependent Claim
320 words
A composition for dyeing human keratinous fibers comprising in a cosmetically acceptable medium at least one indole derivative having the formula ##STR6## wherein R 1 represents hydrogen, C 1 -C 6 alkyl or --SiR 9 R 10 R 11 , R 2 and R 3 , each independently, represent hydrogen, C 1 -C 6 lower alkyl, carboxyl, lower alkoxycarbonyl wherein the alkoxy moiety contains 1-6 carbon atoms or --COOSiR 9 R 10 R 11 , R 4 and R 5 , each independently, represent hydrogen, C 1 -C 20 linear or branched alkyl, formyl, linear or branched C 2 -C 20 acyl, linear or branched C 3 -C 20 alkenoyl, --SiR 9 R 10 R 11 , --P(O)(OR 6 ) 2 or R 6 OSO 2 --, or R 4 and R 5 together with the oxygen atoms to which they are attached form a ring containing or not a carbonyl group, a methylene group, a thiocarbonyl group, a >P(O)OR 6 group or a >CR 7 R 8 group, R 6 and R 7 represent hydrogen or C 1 -C 6 lower alkyl, R 8 represents C 1 -C 6 lower alkoxy, monoalkylamino wherein the alkyl moiety has 1-6 carbon atoms or dialkylamino wherein the alkyl moiety has 1-6 carbon atoms, R 9 , R 10 and R 11 , each independently, represent C 1 -C 6 linear or branched alkyl, with the proviso that at least one of R 1 -R 5 is other than hydrogen, the inorganic or organic acid addition salts of said indole and the corresponding alkali metal, alkaline earth metal and amine salts thereof, said indole being present in an amount ranging from 0.01 to 5 percent by weight based on the total weight of said composition, and an iodide present in an amount ranging from 0.007 to 4 percent by weight based on the total weight of said composition and expressed as iodide ions.
Claim 17
Dependent Claim
21 words
The composition of claim 14 wherein said cosmetically acceptable medium contains water and has a pH ranging from 3.5 to 7.
Claim 18
Dependent Claim
91 words
The composition of claim 14 wherein said indole derivative has the formula ##STR7## wherein R' 2 and R' 3 , each independently, represent hydrogen, C 1 -C 6 lower alkyl, C 1 -C 6 carboxyl, lower alkoxy carbonyl wherein the alkoxy moiety contains 1-6 carbon atoms, R' 4 and R' 5 , each independently, represent hydrogen, C 1 -C 6 alkyl, C 2 -C 20 linear acyl, or trimethylsilyl, or R' 4 and R' 5 together with the oxygen atoms to which they are attached form a methylenedioxy or carbonyldioxy ring.
Claim 19
Dependent Claim
32 words
The composition of claim 14 wherein said indole derivative is selected from the group consisting of 5-methoxy-6-hydroxyindole, 3-methyl-5,6-dihydroxyindole, 2-methyl-5,6-dihydroxyindole, 5,6-bis (trimethylsilyloxy) indole, 5-(or 6-) myristoyloxy-6-(or 5-) hydroxyindole, 5,6-(methylenedioxy) indole, 5-acetoxy-6-hydroxyindole, 2-ethoxycarbonyl-5,6-dihydroxyindole, 5-hydroxy-6-methoxyindole,
Claim 20
Dependent Claim
3 words
6-carbonyldioxyindole and 2-carboxy-5,6-dihydroxyindole.
Claim 21
Dependent Claim
3 words
6-carbonyldioxyindole and 2-carboxy-5,6-dihydroxyindole.
Claim 22
Dependent Claim
21 words
The composition of claim 14 wherein said iodide is an alkali metal iodide, an alkaline earth metal iodide or ammonium iodide.
Claim 23
Dependent Claim
9 words
The composition of claim 14 which also contains 5,6-dihydroxyindole.
Claim 24
Dependent Claim
36 words
A multi-compartment kit for dyeing human keratinous fibers comprising a first compartment containing the composition of claim 14 and a second compartment containing a solution of hydrogen peroxide at a pH ranging from 2 to 7.
Claim 25
Dependent Claim
372 words
A multi-compartment kit for dyeing human keratinous fibers comprising a first compartment containing an iodide in amount ranging from 0.007 to 4 percent by weight based on the total weight of the composition and expressed as iodide ions in a cosmetically acceptable medium, a second compartment containing in a cosmetically acceptable medium an indole derivative having the formula ##STR8## wherein R 1 represents hydrogen, C 1 -C 6 lower alkyl or --SiR 9 R 10 R 11 , R 2 and R 3 , each independently, represent hydrogen, C 1 -C 6 lower alkyl, carboxyl, lower alkoxycarbonyl wherein the alkoxy moiety contains 1-6 carbon atoms or --COOSiR 9 R 10 R 11 , R 4 and R 5 , each independently, represent hydrogen, C 1 -C 20 linear or branched alkyl, formyl, linear or branched C 2 -C 20 acyl, linear or branched C 3 -C 20 alkenoyl, --SiR 9 R 10 R 11 , --P(O)(OR 6 ) 2 or R 6 OSO 2 --, or R 4 and R 5 together with the oxygen atoms to which they are attached form a ring containing or not a carbonyl group, a methylene group, a thiocarbonyl group, a >P(O)OR 6 group or a >CR 7 R 8 group, R 6 and R 7 represent hydrogen or C 1 -C 6 lower alkyl, R 8 represents C 1 -C 6 lower alkoxy, monoalkylamino wherein the alkyl moiety has 1-6 carbon atoms or dialkylamino wherein the alkyl moiety has 1-6 carbon atoms, R 9 , R 10 and R 11 , each independently, represent C 1 -C 6 linear or branched alkyl, with the proviso that at least one of R 1 -R 5 is other than hydrogen, the inorganic or organic acid addition salts of said indole and the corresponding alkali metal, alkaline earth metal and amine salts thereof, said indole being present in an amount ranging from 0.01 to 5 percent by weight based on the total weight of said composition, and a third compartment containing a 1-40 volume solution of hydrogen peroxide at a pH ranging from 2 to 7, the contents of said third compartment designed to be mixed with the contents of said second compartment at the time of use.
Claim 26
Dependent Claim
372 words
A multi-compartment kit for dyeing human keratinous fibers comprising a first compartment containing an iodide in amount ranging from 0.007 to 4 percent by weight based on the total weight of the composition and expressed as iodide ions in a cosmetically acceptable medium, a second compartment containing in a cosmetically acceptable medium an indole derivative having the formula ##STR8## wherein R 1 represents hydrogen, C 1 -C 6 lower alkyl or --SiR 9 R 10 R 11 , R 2 and R 3 , each independently, represent hydrogen, C 1 -C 6 lower alkyl, carboxyl, lower alkoxycarbonyl wherein the alkoxy moiety contains 1-6 carbon atoms or --COOSiR 9 R 10 R 11 , R 4 and R 5 , each independently, represent hydrogen, C 1 -C 20 linear or branched alkyl, formyl, linear or branched C 2 -C 20 acyl, linear or branched C 3 -C 20 alkenoyl, --SiR 9 R 10 R 11 , --P(O)(OR 6 ) 2 or R 6 OSO 2 --, or R 4 and R 5 together with the oxygen atoms to which they are attached form a ring containing or not a carbonyl group, a methylene group, a thiocarbonyl group, a >P(O)OR 6 group or a >CR 7 R 8 group, R 6 and R 7 represent hydrogen or C 1 -C 6 lower alkyl, R 8 represents C 1 -C 6 lower alkoxy, monoalkylamino wherein the alkyl moiety has 1-6 carbon atoms or dialkylamino wherein the alkyl moiety has 1-6 carbon atoms, R 9 , R 10 and R 11 , each independently, represent C 1 -C 6 linear or branched alkyl, with the proviso that at least one of R 1 -R 5 is other than hydrogen, the inorganic or organic acid addition salts of said indole and the corresponding alkali metal, alkaline earth metal and amine salts thereof, said indole being present in an amount ranging from 0.01 to 5 percent by weight based on the total weight of said composition, and a third compartment containing a 1-40 volume solution of hydrogen peroxide at a pH ranging from 2 to 7, the contents of said third compartment designed to be mixed with the contents of said second compartment at the time of use.
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