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US 7,611,546 B2Granted
Composition comprising at least one substituted acetylenic carbocyanin derivative, process for treating keratin fibres using it, and device therefor
AssigneeL'oreal
InventorAlain Lagrange
Life of this patent
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Abstract
The invention relates to a composition for dyeing human keratin fibers, comprising, in a cosmetically acceptable medium, one or more cationic direct dyes comprising at least one carbon-carbon triple bond, for instance dyes of formula (I), (II) or (III) below: in which A1, A2 and A3, independently of each other, correspond to a cationic heterocyclic group and B1, B2 and B3, independently of each other, correspond to a particular aromatic nucleus; n may be equal to 1 or 2.
Claims15
A composition for dyeing human keratin fibers comprising, in a cosmetically acceptable medium, at least one direct dye chosen from direct dyes of formulae (I), (II) and (III):
- wherein:
- A1, A2 and A3, independently of each other, are chosen from cationic heterocyclic groups comprising at least one quaternized nitrogen and optionally fused with at least one aromatic nucleus, and wherein A1, A2 and A3 are attached to the at least one C≡C functional group via one of the carbon atoms of the cationic heterocycle or via the at least one aromatic nucleus to which the cationic heterocycle is optionally fused;
- and wherein said at least one quaternized nitrogen atom optionally bears at least one radical chosen from amino radicals;
- C2-C20 acyl radicals;
- and C1-C25 alkyl radicals optionally substituted with at least one radical chosen from phenyl, phenyl-carbonyl, (C1-C4)alkoxycarbonyl, sulfo (—SO3M, wherein M is chosen from a hydrogen atom and alkali metals), ethylenyl (—CH═CH2), acetylenyl (—C≡CH), and phenyl-acetylenyl (—C≡C—C6H5);
- A1, A2 and A3 may be optionally substituted, beyond the radicals borne by the quaternized nitrogen atoms, with at least one radical chosen from halogen atoms, C1-C25 alkyl radicals, (C1-C4) alkoxy radicals, (C1-C20)alkylcarbonylamino radicals, and phenyl radicals;
- B1, B2 and B3, independently of each other, are aromatic nucleuses chosen from phenyl groups, anthracenyl groups, and naphthyl groups, attached to one or two C≡C functional groups;
- B1, B2 and B3 may be optionally substituted with at least one group chosen from:
- amino groups optionally bearing one or two radicals, independently of each other, chosen from C1-C18 alkyl, (C1-C20)alkylcarbonyl, (C1-C20)alkylsulfonyl, and phenyl optionally substituted with a C1-C4 alkoxy group;
- hydroxyl;
- C1-C4 alkoxy;
- C1-C10 alkyl optionally bearing an amino group;
- phenoxy;
- sulfo (—SO3M, wherein M is chosen from a hydrogen atom and alkali metals);
- cyano;
- trifluoromethyl;
- halogen chosen from chlorine, fluorine and bromine;
- and
- acetylthio (CH3—CO—S—);
- n is equal to 1 or 2;
- the electrical neutrality of the at least one direct dye being optionally assured via at least one cosmetically acceptable anion;
- and wherein the composition also comprises at least one surfactant present in an amount ranging from 0.01% to 50% by weight relative to the total weight of the composition, and chosen from anionic, amphoteric, nonionic, zwitterionic and cationic surfactants.
19 more elements
A composition for dyeing human keratin fibers comprising, in a cosmetically acceptable medium, at least one direct dye chosen from:
- Pyridinium salt, 4-[(4-
- Pyridinium salt, 4-[(4-
- aminophenyl)ethynyl]-1 -methyl
- hydroxyphenyl)ethynyl]-1 -methyl
- Pyridinium salt, 4-[(4-
- Pyridinium salt, 1-methyl-4-[(4-
- ethylphenyl)ethynyl]-1 -methyl-
- methylphenyl)ethynyl]
- Pyridinium salt, 4-[(4-
- Salt of 4-methylbenzenesulfonic acid
- cyanophenyl)ethynyl]-1-methyl
- (1:1) and of pyridinium, 4-[[4-
- (dimethylamino)phenyl]ethynyl]-1-
- methyl-, monohydrate
- Quinolizinium salt, 4-[[4-
- (trifluoromethyl)phenyl]ethynyl]-
- Pyridinium trichloride, 4,4′,4″-[nitrilotris(4,1-phenylene-2,1-ethynediyl)]tris[1 -
- methyl-, trichloride
- Quinolizinium salt, 1-[[4-
- Quinolizinium salt, 3-[(3-
- (trifluoromethyl)phenyl]ethynyl]-
- bromophenyl)ethynyl]-
- Quinolizinium salt, 3-[[4-
- Quinolizinium salt, 3-[(4-
- (trifluoromethyl)phenyl]ethynyl]-
- methoxyphenyl)ethynyl]-
- Quinolizinium salt, 3-[(4-
- Quinolizinium salt, 2-[(3-
- methylphenyl)ethynyl]-
- bromophenyl)ethynyl]-
- Quinolizinium salt, 2-[[4-
- Quinolizinium salt, 2-[(4-
- (trifluoromethyl)phenyl]ethynyl]
- methoxyphenyl)ethynyl]
- Quinolizinium salt, 2-[(4-
- Quinolizinium salt, 4-[(4-
- methylphenyl)ethynyl]-
- methoxyphenyl)ethynyl]-
- Quinolizinium salt, 1-[(4-
- Pyridinium iodide, 5-[[4-
- methoxyphenyl)ethynyl]-
- (acetylthio)phenyl]ethynyl]-1-methyl-2-
- (phenylethynyl)
- Pyridinium salt, 2-methyl-1-(2-oxo-2-
- Pyridinium salt, 4-[(4-
- phenylethyl)-6-(phenylethynyl)-
- methoxyphenyl)ethynyl]-1-octadecyl-
- Pyridinium salt, 1-docosyl-4-[(4-
- Isoquinolinium salt, 6-[(4-
- methoxyphenyl)ethynyl]-
- methoxyphenyl)ethynyl]-2-methyl
- Pyridinium salt, 1-decyl-4-[(4-
- Isoquinolinium salt, 6-[[4-
- methoxyphenyl)ethynyl]-
- (dimethylamino)phenyl]ethynyl]-2-methyl
- Pyridinium salt, 3-[[4-(1-amino-1-
- Pyridinium salt, 1-(2-oxo-2-phenylethyl)-
- methylethyl)phenyl]ethynyl]-1-methyl
- 2-(phenylethynyl)-
- Isoquinolinium salt, 2-methyl-6-
- Pyridinium salt, 1-octadecyl-4-
- (phenylethynyl)-
- (phenylethynyl)-
- Pyridinium salt, 1-docosyl-4-
- Salt of trifluoromethanesulfonic acid
- (phenylethynyl)-
- (1:1) and of pyridinium, 3,5-bis[(4-
- hydroxy-3-methoxyphenyl)ethynyl]-1-
- methyl
- Salt of trifluoromethanesulfonic acid
- Pyridinium salt, 4-[(4-
- (1:1) and of pyridinium, 2,6-bis[(4-
- bromophenyl)ethynyl]-1-dodecyl
- hydroxy-3-methoxyphenyl)ethynyl]-1-
- methyl
- Pyridinium salt, 1-methyl-3,5-
- Pyridinium salt, 1-methyl-4-(1-
- bis(phenylethynyl)-
- naphthalenylethynyl)
- Thioxanthylium perchlorate, 4-chloro-
- Pyridinium salt, 1-methyl-3-
- 9-[[4-(dimethylamino)phenyl]ethynyl]
- (phenylethynyl)-
- 3H-Pyrrolo[2,3-b]pyridinium salt, 7-(6-
- Pyridinium inner salt, 4-[[4-
- ethoxy-6-oxohexyl)-2,3,3-trimethyl-5-
- (dihexylamino)phenyl]ethynyl]-1-(4-
- [[4-[(methylsulfonyl)amino]-
- sulfobutyl)
- phenyl]ethynyl
- Pyridinium methanesulfonate, 1-
- Acridinium salt, 9-[(2-
- amino-2-(phenylethynyl)
- bromophenyl)ethynyl]-10-methyl
- Pyridinium salt, 4-[[4-(dimethylamino)-
- Pyridinium salt, 4-[[4-(dimethylamino)-
- 2,3,5,6-tetrafluorophenyl]ethynyl]-
- 2,3,5,6-tetrafluorophenyl]ethynyl]-1-
- 2,3,5,6-tetrafluoro-1-methyl
- methyl-
- Pyridinium salt, 4-[[4-
- Pyridinium salt, 4-[[4-
- (dimethylamino)phenyl]ethynyl]-
- (dimethylamino)phenyl]ethynyl]-1-
- 2,3,5,6-tetrafluoro-1-methyl-
- methyl
- Pyridinium iodide, 1-methyl-3,5-
- Pyridinium iodide, 1-methyl-3-
- bis(phenylethynyl)
- (phenylethynyl)
- Phenazinium salt, 2,2′-(9,10-
- Salt of trifluoromethanesulfonic acid and
- anthracenediyldi-2,1-
- of pyridinium, 1-methyl-2-
- ethynediyl)bis[5,10-dimethyl
- (phenylethynyl)
- Salt of trifluoromethanesulfonic acid
- Salt of trifluoromethanesulfonic acid
- (1:1) and of pyridinium, 1-(2-propynyl)-
- (1:1) and of thiazolium, 3-methyl-2-
- 2-[(3,4,5-trimethoxyphenyl)ethynyl]
- (phenylethynyl)
- Salt of trifluoromethanesulfonic acid
- Salt of trifluoroacetic acid(1:1) and of
- (1:1) and of benzothiazolium, 3-
- pyridinium, 1-methyl-2-(phenylethynyl)
- methyl-2-(phenylethynyl)
- Salt of trifluoroacetic acid (1:1) and of
- Pyridinium salt, 4-[[4-[bis(4-
- 1H-Benzimidazolium, 1-methyl-2-
- methoxyphenyl)amino]phenyl]ethynyl]-1-
- (phenylethynyl)-3-(3-phenyl-2-
- butyl
- propynyl)
- Salt of trifluoroacetic acid (:1) and of
- Pyridinium salt, 2-(phenylethynyl)-1-(2-
- thiazolium, 3-methyl-2-(phenylethynyl)
- propenyl)-
- Pyridinium inner salt, 4-[[4-
- 3H-Pyrrolo[2,3-b]pyridinium inner salt,
- (dibutylamino)phenyl]ethynyl]-1-(3-
- 2,3,3-trimethyl-5-[[4-
- sulfopropyl)
- [(methylsulfonyl)amino]phenyl]ethynyl]-
- 7-(3-sulfobutyl)
- 3H-Pyrrolo[2,3-b]pyridinium, 7-(6-
- 3H-Pyrrolo[2,3-b]pyridinium inner salt,
- ethoxy-6-oxohexyl)-2,3,3-trimethyl-5-
- 2,3,3-trimethyl-7-(3-sulfobutyl)-5-[(4-
- [[4-[(methylsulfonyl)amino]-
- sulfophenyl)ethynyl]
- phenyl]ethynyl]-bromide
- 3H-Pyrrolo[2,3-b]pyridinium inner salt,
- Benzothiazolium salt, 3-methyl-2-[(4-
- 7-(6-ethoxy-6-oxohexyl)-2,3,3-
- phenoxyphenyl)ethynyl]-
- trimethyl-5-[(4-sulfophenyl)ethynyl]
- 3H-Pyrrolo[2,3-b]pyridinium inner salt,
- Benzothiazolium salt, 2-[(4-
- 2,3,3,7-tetramethyl-5-[(4-
- methoxyphenyl)ethynyl]-3-methyl
- sulfophenyl)ethynyl]
- Benzothiazolium salt, 3-methyl-2-[[4-
- Salt of trifluoromethanesulfonic acid
- (1-methylethyl)phenyl]ethynyl]-
- (1:1) and of
- 1H-Benzimidazolium, 1,3-dimethyl-2-
- (phenylethynyl)
- Benzothiazolium salt, 3-methyl-2-
- Salt of 2,4,6-trinitrophenol (1:1) and of
- (phenylethynyl)-
- quinolizinium, 2-(phenylethynyl)
- Salt of trifluoromethanesulfonic acid
- Isoquinolinium iodide, 6-[(4-
- (1:1) 1H-Benzimidazolium, 1-methyl-2-
- methoxyphenyl)ethynyl]-2-methyl
- (phenylethynyl)-3-(3-phenyl-2-
- propynyl)
- Salt of 2,4,6-trinitrophenol (1:1) and of
- Benzoxazolium inner salt, 2-methyl-5-
- quinolizinium, 1-(phenylethynyl)
- (phenylethynyl)-3-(4-sulfobutyl)
- Isoquinolinium iodide, 6-[[4-
- Salt of trifluoromethanesulfonic acid
- (dimethylamino)phenyl]ethynyl]-2-
- (1:1) and of quinolinium, 1-methyl-2-
- methyl
- (phenylethynyl)
- Isoquinolinium iodide, 2-methyl-6-
- Salt of trifluoromethanesulfonic acid
- (phenylethynyl)
- (1:1) and of
- 3H-Indolium, 1,3,3-trimethyl-2-
- (phenylethynyl)
- Benzothiazolium inner salt, 2-methyl-5-
- Pyridinium methyl sulfate, 4-[(4-
- (phenylethynyl)-3-(4-sulfobutyl)
- chlorophenyl)ethynyl]-1-methyl-, methyl
- sulfate
- Salt of trifluoromethanesulfonic acid
- Pyridinium bromide, 4-[(4-
- (1:1) and of b
- bromophenyl)ethynyl]-1-docosyl
- Benzothiazolium, 2-[(4-
- chlorophenyl)ethynyl]-3-methyl-,
- Pyridinium methyl sulfate, 4-[(4-
- Pyridinium perchlorate, 1-butyl-3,5-
- bromophenyl)ethynyl]-1-methyl-
- dimethyl-2,6-diphenyl-4-(phenylethynyl)
- Pyridinium bromide, 4-[(4-
- Pyridinium bromide, 4-[(4-
- bromophenyl)ethynl]-1-dodecyl
- methoxyphenyl)ethynyl]-1-octadecyl
- Pyridinium perchlorate, 3,5-dimethyl-
- Pyridinium bromide, 1-docosyl-4-[(4-
- 2,6-diphenyl-4-(phenylethynyl)-1-
- methoxyphenyl)ethynyl]
- (phenylmethyl)
- Pyridinium perchlorate, 1,3,5-trimethyl-
- Pyridinium bromide, 1-docosyl-4-
- 2,6-diphenyl-4-(phenylethynyl)
- (phenylethynyl)
- Pyridinium bromide, 1-decyl-4-[(4-
- 1-Methyl-4-phenylethynylpyridinium
- methoxyphenyl)ethynyl]
- perchlorate
- Pyridinium bromide, 1-octadecyl-4-
- 1-Methyl-2,6-
- (phenylethynyl)
- bis(phenylethynyl)pyridinium perchlorate
- 1-Methyl-2-phenylethynylquinolinium
- 1-Ethyl-2-phenylethynylquinolinium
- para-toluenesulfonate
- perchlorate
- 1-Methyl-2-phenylethynylpyridinium
- Salt of 1-Methyl-4-
- perchlorate
- phenylethynylpyridinium methyl
- 1-Methyl-2-phenylethynylquinolinium
- Pyridinium bromide, 2-methyl-1-(2-oxo-
- perchlorate
- 2-phenylethyl)-6-(phenylethynyl)
- Methyl-2-phenylethynylpyridinium
- 1H-Benzimidazolium 1,3-dimethyl-2-(1-
- methyl sulfate
- naphthalenylethynyl) methyl sulfate
- Pyridinium methyl sulfate, 4-[[4-
- Benzimidazolium iodide, 1,3-dimethyl-2-
- (dimethylamino)-2-[(1-
- (phenylethynyl)-,
- oxooctadecyl)amino]phenyl]ethynyl]-
- 1-methyl-3-[(1-oxooctadecyl)amino]
- Benz[cd]indolium perchlorate, 1-acetyl-
- Pyridinium iodide, 1-methyl-4-(1-
- 5-ethoxy-2-(phenylethynyl)
- naphthalenylethynyl)-,
- Phenazinium salt, 2,2′-(1,4-phenylenedi-2,1-ethynediyl)bis[5,10-dimethyl-
- and wherein the composition also comprises at least one surfactant present in an amount ranging from 0.01% to 50% by weight relative to the total weight of the composition, and chosen from anionic, amphoteric, nonionic, zwitterionic and cationic surfactants.
255 more elements
A process for treating keratin fibers, comprising:
- applying to the keratin fibers a cosmetic composition comprising, in a cosmetically acceptable medium, at least one direct dye chosen from direct dyes of formulae (I), (II) and (III):
- wherein:
- A1, A2 and A3, independently of each other, are chosen from cationic heterocyclic groups comprising at least one quaternized nitrogen and optionally fused with at least one aromatic nucleus, and wherein A1, A2 and A3 are attached to the at least one C≡C functional group via one of the carbon atoms of the cationic heterocycle or via the at least one aromatic nucleus to which the cationic heterocycle is optionally fused;
- and wherein said at least one quaternized nitrogen atom optionally bears at least one radical chosen from amino radicals;
- C2-C20 acyl radicals;
- and C1-C25 alkyl radicals optionally substituted with at least one radical chosen from phenyl, phenyl-carbonyl, (C1-C4)alkoxycarbonyl, sulfo (—SO3M, wherein M is chosen from a hydrogen atom and alkali metals), ethylenyl (—CH═CH2), acetylenyl (—C≡CH), and phenyl-acetylenyl (—C≡C—C6H5);
- A1, A2 and A3 may be optionally substituted, beyond the radicals borne by the quaternized nitrogen atoms, with at least one radical chosen from halogen atoms, C1-C25 alkyl radicals, (C1-C4) alkoxy radicals, (C1-C20)alkylcarbonylamino radicals, and phenyl radicals;
- B1, B2 and B3, independently of each other, are aromatic nucleuses chosen from phenyl groups, anthracenyl groups, and naphthyl groups, attached to one or two C≡C functional groups;
- B1, B2 and B3 may be optionally substituted with at least one group chosen from:
- amino groups optionally bearing one or two radicals, independently of each other, chosen from C1-C18 alkyl, (C1-C20)alkylcarbonyl, (C1-C20)alkylsulfonyl, and phenyl optionally substituted with a C1-C4 alkoxy group;
- hydroxyl;
- C1-C4 alkoxy;
- C1-C10 alkyl optionally bearing an amino group;
- phenoxy;
- sulfo (—SO3M, wherein M is chosen from a hydrogen atom and alkali metals);
- cyano;
- trifluoromethyl;
- halogen chosen from chlorine, fluorine and bromine;
- and
- acetylthio (CH3—CO—S—);
- n is equal to 1 or 2;
- the electrical neutrality of the at least one direct dye being optionally assured via at least one cosmetically acceptable anion.
19 more elements
A multi-compartment device for dyeing and lightening the hair, comprising:
- at least one first compartment containing a composition comprising, in a cosmetically acceptable medium, at least one direct dye chosen from direct dyes of formulae (I), (II) and (III):
- wherein:
- A1, A2 and A3, independently of each other, are chosen from cationic heterocyclic groups comprising at least one quaternized nitrogen and optionally fused with at least one aromatic nucleus, and wherein A1, A2 and A3 are attached to the at least one C≡C functional group via one of the carbon atoms of the cationic heterocycle or via the at least one aromatic nucleus to which the cationic heterocycle is optionally fused;
- and wherein said at least one quaternized nitrogen atom optionally bears at least one radical chosen from amino radicals;
- C2-C20 acyl radicals;
- and C1-C25 alkyl radicals optionally substituted with at least one radical chosen from phenyl, phenyl-carbonyl, (C1-C4)alkoxycarbonyl, sulfo (—SO3M, wherein M is chosen from a hydrogen atom and alkali metals), ethylenyl (—CH═CH2), acetylenyl (—C≡CH), and phenyl-acetylenyl (—C≡C—C6H5);
- A1, A2 and A3 may be optionally substituted, beyond the radicals borne by the quaternized nitrogen atoms, with at least one radical chosen from halogen atoms, C1-C25 alkyl radicals, (C1-C4) alkoxy radicals, (C1-C20)alkylcarbonylamino radicals, and phenyl radicals;
- B1, B2 and B3, independently of each other, are aromatic nucleuses chosen from phenyl groups, anthracenyl groups, and naphthyl groups, attached to one or two C≡C functional groups;
- B1, B2 and B3 may be optionally substituted with at least one group chosen from:
- amino groups optionally bearing one or two radicals, independently of each other, chosen from C1-C18 alkyl, (C1-C20)alkylcarbonyl, (C1-C20)alkylsulfonyl, and phenyl optionally substituted with a C1-C4 alkoxy group;
- hydroxyl;
- C1-C4 alkoxy;
- C1-C10 alkyl optionally bearing an amino group;
- phenoxy;
- sulfo (—SO3M, wherein M is chosen from a hydrogen atom and alkali metals);
- cyano;
- trifluoromethyl;
- halogen chosen from chlorine, fluorine and bromine;
- and
- acetylthio (CH3—CO—S—);
- n is equal to 1 or 2;
- the electrical neutrality of the at least one direct dye being optionally assured via at least one cosmetically acceptable anion;
- and
- at least one second compartment containing a composition comprising at least one oxidizing agent.
21 more elements
Dependencies are inferred from the claim text.