US4822375A
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Dyeing compositions for keratinous fibres based on indole derivatives, and new compounds
Assignee: L'Oréal SA
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Filing: 1987-03-05
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Granted: 1989-04-18
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Expires: 2007-03-05
Abstract
Abstract Dyeing compositions for keratinous fibres based on indole derivatives, and new compounds. Dyeing composition for keratinous fibres, and especially human hair, characterized in that it contains, in a cosmetically acceptable medium suitable for dyeing these fibres, at least one dye corresponding to the formula: <IMAGE> (I) in which R1 denotes a hydrogen atom or a lower alkyl group or a group -SiR9R10R11; R2 and R3, which may be identical or different, denote a hydrogen atom, a lower alkyl group, a carboxyl group, a lower alkoxycarbonyl group or a group -COOSiR9- R10R11; and R5, which may be identical or different, denote at least one linear or branched C1-C20 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-, the other group R4 or R5 being able to be a hydrogen atom, R4 and R5 are not simultaneously acetyl, or alternatively R4 and R5, together with the oxygen atoms to which they are attached, form a ring optionally containing a carbonyl group, a thiocarbonyl group, a group>P(O)OR6 or>CR7R8; R6 denoting a hydrogen atom or a lower alkyl group, R7 denoting a hydrogen atom or a lower alkyl group, and R8 denotes a lower alkoxy group or a mono- or dialkylamino group, R9, R10 and R11, which may be identical or different, denoting linear or branched lower alkyl groups, and the cosmetically acceptable salts of alkali metals, alkaline earth metal metals, ammonia or amines.
Inventors
- 👤 Gerard Lang
- 👤 Herve Richard
- 👤 Madeleine Leduc
- 👤 Alex Junino
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 23:23
CPC Classifications
C; C07; C07D; C07D491/00; C07D491/02; C07D491/04; A; A61; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/49; A61K8/4906; A61K8/4913; A61K8/492; A61Q; A61Q5/00; A61Q5/10; C07D209/00; C07D209/02; C07D209/04; C07D209/08; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804; C07F9/00; C07F9/02; C07F9/547; C07F9/553; C07F9/572; C07F9/5728; C09; C09B; C09B69/00; C09B69/007; C09B69/008
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
311 words
A dye composition for keratinous fibers comprises, in a cosmetically acceptable medium and in an amount ranging from 0.01 to 5 percent by weight based on the total weight of said composition, at least one dye having the formula ##STR5## wherein R 1 represents hydrogen, lower alkyl or --SiR 9 R 10 R 11 , R 2 and R 3 , each independently, represent hydrogen, lower alkyl, lower alkoxy carbonyl or --COOSiR 9 R 10 R 11 , R 4 and R 5 , each independently, represent a member selected from the group consisting of 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 9 R 10 R 11 , --P(O)(OR 6 ) 2 and R 6 OSO 2 --, or one of R 4 and R 5 is hydrogen and the other has the meaning given above, with the proviso that R 4 and R 5 are not simultaneously acetyl, or R 4 and R 5 together with the oxygen atoms to which they are attached form a ring containing a carbonyl group, a thiocarbonyl group, a >P(O)OR 6 group or a >CR 7 R 8 group, R 6 represents hydrogen or lower akyl, R 7 represents hydrogen or lower alkyl, R 8 represents lower alkoxy, monoalkylamino or dialkylamino, R 9 , R 10 and R 11 , each independently, represent linear or branched lower alkyl, and the cosmetically acceptable alkali metal, alkaline earth metal, ammonia or amine salts of the dye of formula I, said dye composition also including an effective amount of at least one of a surfactant, an anionic polymer, a nonionic polymer a cationic polymer, an amphoteric polymer, a thickening agent, a penetrating agent, a swelling agent, a sequestering agent, an antioxidant, a buffer, an electrolyte and a perfume.
Claim 2
Dependent Claim
311 words
A dye composition for keratinous fibers comprises, in a cosmetically acceptable medium and in an amount ranging from 0.01 to 5 percent by weight based on the total weight of said composition, at least one dye having the formula ##STR5## wherein R 1 represents hydrogen, lower alkyl or --SiR 9 R 10 R 11 , R 2 and R 3 , each independently, represent hydrogen, lower alkyl, lower alkoxy carbonyl or --COOSiR 9 R 10 R 11 , R 4 and R 5 , each independently, represent a member selected from the group consisting of 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 9 R 10 R 11 , --P(O)(OR 6 ) 2 and R 6 OSO 2 --, or one of R 4 and R 5 is hydrogen and the other has the meaning given above, with the proviso that R 4 and R 5 are not simultaneously acetyl, or R 4 and R 5 together with the oxygen atoms to which they are attached form a ring containing a carbonyl group, a thiocarbonyl group, a >P(O)OR 6 group or a >CR 7 R 8 group, R 6 represents hydrogen or lower akyl, R 7 represents hydrogen or lower alkyl, R 8 represents lower alkoxy, monoalkylamino or dialkylamino, R 9 , R 10 and R 11 , each independently, represent linear or branched lower alkyl, and the cosmetically acceptable alkali metal, alkaline earth metal, ammonia or amine salts of the dye of formula I, said dye composition also including an effective amount of at least one of a surfactant, an anionic polymer, a nonionic polymer a cationic polymer, an amphoteric polymer, a thickening agent, a penetrating agent, a swelling agent, a sequestering agent, an antioxidant, a buffer, an electrolyte and a perfume.
Claim 3
Dependent Claim
22 words
The dye composition of claim 1 wherein said lower alkyl contains 1-6 carbon atoms and said lower alkoxy contains 1-6 carbon atoms.
Claim 4
Dependent Claim
73 words
The dye composition of claim 1 wherein said dye of formula I is selected from the group consisting of 6-hydroxy-5-methoxyindole, 5-hydroxy-6-methoxyindole, 6-acetoxy-5-methoxyindole, (5 or 6)-acetoxy-(6 or 5)-hydroxyindole, 5,6-carbonyldioxyindole, (5 or 6)-formyloxy-(6 or 5)-hydroxyindole, (5 or 6)-acetoxy-(6 or 5)-formyloxyindole, 6-formyloxy-5-methoxyindole, 5-butoxy-6-hydroxyindole, 6-butoxy-5-hydroxyindole, (5 or 6)-hydroxy-(6 or 5)-trimethylsilyloxyindole, 5,6-bis(trimethylsilyloxy)indole, 5,6-[(1-ethoxyethylidene)dioxy]indole, 5,6-dihydroxyindolecyclic phosphodiester, 5,6-thiocarbonyldioxyindole, 5-methoxy-6-trimethylsilyloxyindole, 5,6-bis-(trimethylsilyloxy)-2-methylindole, 5,6-carbonyldioxy-2-methylindole, (5 or 6)-hydroxy-(6 or 5)-myristoyloxyindole, 5,6-dimyristoyloxyindole, (5 or 6)-hydroxy-(6 or 5)-oleoyloxyindole, 5,6-dioleoyloxyindole, 5,6-bis(trimethylsilyloxy)-2-carbethoxyindole, 5,6-bis(trimethylsilyloxy)-2-(trimethylsilyloxy carbonyl)indole, 5,6-bis(trimethylsilyloxy)-3-methylindole, 6-hexadecyloxy-5-methoxyindole, 6-hexadecyloxy-5-hydroxyindole, 5-hexadecyloxy-6-hydroxyindole,
Claim 5
Dependent Claim
19 words
6-dipivaloyloxyindole, (5 or 6)-hydroxy-(6 or 5)-pivaloyloxyindole, 5,6-dihexanoyloxyindole, (5 or 6)-hexanoyloxy-(6 or 5)-hydroxyindole, 5,6-dibutanoyloxyindole and (5 or 6)-butanoyloxy-(6 or 5)-hydroxyindole.
Claim 6
Dependent Claim
19 words
6-dipivaloyloxyindole, (5 or 6)-hydroxy-(6 or 5)-pivaloyloxyindole, 5,6-dihexanoyloxyindole, (5 or 6)-hexanoyloxy-(6 or 5)-hydroxyindole, 5,6-dibutanoyloxyindole and (5 or 6)-butanoyloxy-(6 or 5)-hydroxyindole.
Claim 7
Dependent Claim
98 words
The dye composition of claim 1 where in the dye of formula I R 1 represents hydrogen, R 2 and R 3 , each independently, represent hydrogen or lower alkyl, one of R 4 and R 5 represents linear or branched C 1 -C 20 alkyl, linear or branched C 2 -C 20 acyl or linear or branched C 3 -C 20 alkenoyl and the other represents hydrogen, or R 4 and R 5 simultaneously represent SiR 9 R 10 R 11 wherein R 9 , R 10 and R 11 have the meanings given in claim 1.
Claim 8
Dependent Claim
33 words
The dye composition of claim 1 wherein said dye of formula I is present in an amount ranging from 0.03 to 2.5 percent by weight based on the total weight of said composition.
Claim 9
Dependent Claim
24 words
The dye composition of claim 1 in the form of a liquid, a thickened liquid, a cream, a gel, an oil or a powder.
Claim 10
Dependent Claim
23 words
The dye composition of claim 1 wherein said cosmetically acceptable medium is an aqueous medium having a pH ranging from 3.5 to 11.
Claim 11
Dependent Claim
50 words
The dye composition of claim 7 wherein said aqueous medium also contains a surfactant present in an amount ranging from 0.1 to 55 percent by weight and an organic solvent present in an amount ranging from 1 to 60 percent by weight, based on the total weight of said composition.
Claim 12
Dependent Claim
28 words
The dye composition of claim 8 wherein said organic solvent is a lower alcohol, ethyleneglycol monomethyl ether, ethyleneglycol monoethyl ether, ethyleneglycol monobutyl ether or ethyleneglycol monoethyl ether acetate.
Claim 13
Dependent Claim
38 words
The dye composition of claim 1 which contains an anionic, nonionic, cationic or amphoteric polymer or a mixture thereof, in an amount ranging from 0.1 to 5 percent by weight based on the total weight of said composition.
Claim 14
Dependent Claim
15 words
The dye composition of claim 1 wherein said cosmetically acceptable medium is an anhydrous medium.
Claim 15
Dependent Claim
35 words
The dye composition of claim 11 wherein said anhydrous medium is selected from the group consisting of a saturated monohydric alcohol, ethyleneglycol monomethyl ether, ethyleneglycol monoethyl ether, ethyleneglycol monobutyl ether and ethyleneglycol monoethyl ether acetate.
Claim 16
Dependent Claim
284 words
A process for dyeing keratinous fibers comprising applying to said fibers in an amount effective to dye said fibers a dye composition comprising, in a cosmetically acceptable medium, at least one dye having the formula ##STR6## wherein R 1 represents hydrogen, lower alkyl or --SiR 9 R 10 R 11 , R 2 and R 3 , each independently, represent hydrogen, lower alkyl, carbonyl, lower alkoxy carbonyl or --COOSiR 9 R 10 R 11 , R 4 and R 5 , each independently, represent a member selected from the group consisting of 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 9 R 10 R 11 , --P(O)(OR 6 ) 2 , or one of R 4 and R 5 is hydrogen and the other has the meaning given above, with the proviso that R 4 and R 5 are not simultaneously acetyl, or R 4 and R 5 together with the oxygen atoms to which they are attached form a ring containing a carbonyl group, a thiocarbonyl group, a >P(O)OR 6 group or a >CR 7 R 8 group, R 6 represents hydrogen or lower alkyl, R 7 represents hydrogen or lower alkyl, R 8 represents lower alkoxy, monoalkylamino or dialkylamino, R 9 , R 10 and R 11 , each independently, represent linear or branched lower alkyl, and the cosmetically acceptable alkali metal, alkaline earth metal, ammonia or amine salts of the dye of formula I, said dye of formula I being present in said composition in an amount ranging from 0.01 to 5 percent by weight based on the total weight of said composition.
Claim 17
Dependent Claim
284 words
A process for dyeing keratinous fibers comprising applying to said fibers in an amount effective to dye said fibers a dye composition comprising, in a cosmetically acceptable medium, at least one dye having the formula ##STR6## wherein R 1 represents hydrogen, lower alkyl or --SiR 9 R 10 R 11 , R 2 and R 3 , each independently, represent hydrogen, lower alkyl, carbonyl, lower alkoxy carbonyl or --COOSiR 9 R 10 R 11 , R 4 and R 5 , each independently, represent a member selected from the group consisting of 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 9 R 10 R 11 , --P(O)(OR 6 ) 2 , or one of R 4 and R 5 is hydrogen and the other has the meaning given above, with the proviso that R 4 and R 5 are not simultaneously acetyl, or R 4 and R 5 together with the oxygen atoms to which they are attached form a ring containing a carbonyl group, a thiocarbonyl group, a >P(O)OR 6 group or a >CR 7 R 8 group, R 6 represents hydrogen or lower alkyl, R 7 represents hydrogen or lower alkyl, R 8 represents lower alkoxy, monoalkylamino or dialkylamino, R 9 , R 10 and R 11 , each independently, represent linear or branched lower alkyl, and the cosmetically acceptable alkali metal, alkaline earth metal, ammonia or amine salts of the dye of formula I, said dye of formula I being present in said composition in an amount ranging from 0.01 to 5 percent by weight based on the total weight of said composition.
Claim 18
Dependent Claim
61 words
The process of claim 13 comprising initially applying to said keratinous fibers said dye of formula I in an acidic or neutral medium, permitting said dye containing acidic or neutral medium to remain in contact with said fibers for a period of time ranging from 5 to 60 minutes, wringing said fibers dry and contacting said fibers with an oxidizing agent.
Claim 19
Dependent Claim
35 words
The process of claim 14 wherein said oxidizing agent contains an oxidation catalyst selected from the group consisting of a cobalt salt, an iron salt, a manganese salt, a copper salt and an aluminum salt.
Claim 20
Dependent Claim
29 words
The process of claim 18 comprising applying to said keratinous fibers said dye of formula I in an alkaline medium containing, as an alkalinizing agent, ammonia or an amine.
Claim 21
Dependent Claim
39 words
The process of claim 16 which comprises repeating the application to said keratinous fibers of said dye of formula I in said alkaline medium for a number of times sufficient to impart a desired shade to said keratinous fibers.
Claim 22
Dependent Claim
14 words
The process of claim 16 which includes contacting said fibers with an oxidizing agent.
Claim 23
Dependent Claim
32 words
The process of claim 16 which includes adding an oxidizing agent to said alkaline medium containing said dye of formula I, just prior to the application of said medium to said fibers.
Claim 24
Dependent Claim
37 words
The process of claim 13 which comprises, in one stage, contacting said fibers with a metal salt before or after applying in another stage said dye composition to said fibers and rinsing said fibers between said stages.
Claim 25
Dependent Claim
46 words
The process of claim 13 which includes, subsequent to applying said dye composition to said fibers, rinsing said fibers and contacting the rinsed fibers with a hydrogen peroxide solution so as to lighten the tint resulting from the application of said dye composition to said fibers.
Claim 26
Dependent Claim
44 words
The process of claim 13 wherein said dye composition also contains an anionic, nonionic, cationic or amphoteric polymer, or a mixture thereof, and said dye composition is mixed, just prior to application to said fibers, with an aqueous cosmetic vehicle containing cosmetically acceptable additives.
Claim 27
Dependent Claim
29 words
A hair dyeing kit comprising a plurality of compartments, one of said compartments containing the dye composition of claim 1 and another of said compartments containing a metal salt.
Claim 28
Dependent Claim
17 words
The hair dye kit of claim 23 which also contains yet another compartment containing an oxidizing agent.
Claim 29
Dependent Claim
201 words
A compound having the formula ##STR7## wherein R' 1 represents hydrogen or lower alkyl, R' 2 and R' 3 , each independently, represent hydrogen, lower alkyl, carboxyl, lower alkoxy carbonyl or --COOSi(CH 3 ) 3 , one of R' 4 and R' 5 is selected from the group consisting of linear or branched C 10 -C 20 acyl, and --P(O)(OR 6 ) 2 and the other is selected from the group consisting of hydrogen, C 1 -C 8 alkyl, formyl, C 2 -C 9 acyl or aralkyl, or one or both of R' 4 and R' 5 represent --Si(CH 3 ) 3 when R' 1 is other than methyl, or R' 4 and R' 5 together with the oxygen atoms to which they are attached form a ring containing a carbonyl group when one of R' 1 , R' 2 and R' 3 is other than hydrogen, a thiocarbonyl group, a >P(O)OR 6 group or a >CR 7 R 8 group, R 6 represents hydrogen or lower alkyl, R 7 represents hydrogen or lower alkyl and R 8 represents lower alkoxy, monoalkylamino or dialkylamino, and the alkali metal, alkaline earth metal, ammonia or amine salts of the compound of formula II.
Claim 30
Dependent Claim
201 words
A compound having the formula ##STR7## wherein R' 1 represents hydrogen or lower alkyl, R' 2 and R' 3 , each independently, represent hydrogen, lower alkyl, carboxyl, lower alkoxy carbonyl or --COOSi(CH 3 ) 3 , one of R' 4 and R' 5 is selected from the group consisting of linear or branched C 10 -C 20 acyl, and --P(O)(OR 6 ) 2 and the other is selected from the group consisting of hydrogen, C 1 -C 8 alkyl, formyl, C 2 -C 9 acyl or aralkyl, or one or both of R' 4 and R' 5 represent --Si(CH 3 ) 3 when R' 1 is other than methyl, or R' 4 and R' 5 together with the oxygen atoms to which they are attached form a ring containing a carbonyl group when one of R' 1 , R' 2 and R' 3 is other than hydrogen, a thiocarbonyl group, a >P(O)OR 6 group or a >CR 7 R 8 group, R 6 represents hydrogen or lower alkyl, R 7 represents hydrogen or lower alkyl and R 8 represents lower alkoxy, monoalkylamino or dialkylamino, and the alkali metal, alkaline earth metal, ammonia or amine salts of the compound of formula II.
References Cited (Backward Citations)
US3194734A
Cited
US3976639A
Cited
US4013404A
Cited
US4127501A
Cited
US4208183A
Cited
FR2536993A1
Cited
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