Dyeing composition for dyeing keratinous fibers comprising a cationic azo-dye
AssigneeL'oreal
InventorLaurent Vidal
Life of this patent
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Abstract
The invention concerns a novel dyeing composition for dyeing keratinous fibers, in particular human hair, comprising a cationic azo-dye of formula (I): W1-N═N-W2-W3, as well as the dyeing method using said composition and the novel compounds of formula (I).
Claims37
A composition for dyeing keratinous fibers comprising at least one cationic azo dye of formula (I):
- W1—N═N—W2—W3 (I):
- wherein:
- W1 is chosen from 5-membered cationic aromatic heterocycles of formula (II):
- W2 is chosen from divalent carbonaceous aromatic groups and pyridine groups chosen from groups of formulae (III) and (IV):
- W3 is chosen from 7-membered or 8-membered heterocycles of formula (V):
- wherein:
- Z1 is chosen from oxygen and sulfur atoms, and NR12 radicals;
- Z2 is chosen from a nitrogen atom and CR11 radicals;
- R12 and R13, which may be identical or different, are chosen from C1-C8 alkyl radicals optionally substituted with at least one radical chosen from hydroxyl radicals, C1-C2 alkoxy radicals, C2-C4 (poly)hydroxyalkoxy radicals, amino radicals, C1-C2 (di)alkylamino radicals, carboxyl radicals, and sulfonic radicals;
- and optionally substituted phenyl radicals;
- R10 and R11, which may be identical or different, are chosen from hydrogen atoms, optionally substituted phenyl radicals, carboxyl radicals, sulfonylamino radicals, and C1-C4 alkyl radicals optionally substituted with at least one radical chosen from hydroxyl radicals, C1-C2 alkoxy radicals, C2-C4 (poly)hydroxyalkoxy radicals, amino radicals, C1-C2 (di)alkylamino radicals, carboxyl radicals, and sulfonic radicals;
- R6, R7, R8 and R9, which may be identical or different, are chosen from hydrogen atoms;
- chlorine atoms;
- bromine atoms;
- linear and branched C1-C6 hydrocarbonaceous chains, wherein said C1-C6 hydrocarbonaceous chains can each form at least one saturated or unsaturated, 3- to 6-membered carbonaceous ring, wherein at least one carbon atom of each of said C1-C6 hydrocarbonaceous chains is optionally replaced by an entity chosen from an oxygen atom, a nitrogen atom, a sulfur atom, and an SO2 radical and further wherein at least one carbon atom of each of said C1-C6 hydrocarbonaceous chains can be optionally substituted by at least one halogen atom, provided that R6, R7, R8, and R9, which may be identical or different, are not chosen from peroxide bonds, diazo radicals, and nitroso radicals;
- n is an integer chosen from 1 and 2;
- Z4 is chosen from an oxygen atom, a sulfur atom, NR2 radicals, and CR2R2′ radicals;
- R0, R1, R2, R2′, R3, R4 and R5, which may be identical or different, are chosen from hydrogen atoms;
- alkyl radicals;
- alkoxy radicals;
- hydroxyl radicals;
- amino radicals;
- acetoxy radicals;
- NR14R15 groups wherein R14 and R15, which may be identical or different, are chosen from hydrogen atoms and C1-C4 alkyl radicals substituted with at least one radical chosen from halogen atoms, hydroxyl radicals, C1-C2 alkoxy radicals, amino radicals, and C1-C2 amino(di)alkyl radicals;
- sulfonylamino radicals;
- carboxyl radicals;
- carboxamido radicals;
- amido radicals;
- monoalkylamido radicals;
- dialkylamido radicals;
- halogen radicals;
- and C1-C6 alkyl radicals substituted with at least one radical chosen from hydroxyl radicals, C1-C2 alkoxy radicals, C2-C4 (poly)hydroxyalkoxy radicals, amino radicals and C1-C2 (di)alkylamino radicals;
- and
- X is chosen from organic anions and inorganic anions.
A process for the oxidation dyeing of keratinous fibers, comprising applying to said keratinous fibers at least one dyeing composition comprising at least one cationic azo dye of formula (I):
- W1—N═N—W2—W3 (I)
- wherein:
- W1 is chosen from 5-membered cationic aromatic heterocycles of formula (II):
- W2 is chosen from divalent carbonaceous aromatic groups and pyridine groups chosen from groups of formulae (III) and (IV):
- W3 is chosen from 7-membered or 8-membered heterocycles of formula (V):
- wherein:
- Z1 is chosen from oxygen and sulfur atoms, and NR12 radicals;
- Z2 is chosen from a nitrogen atom and CR11 radicals;
- R12 and R13, which may be identical or different, are chosen from C1-C8 alkyl radicals optionally substituted with at least one radical chosen from hydroxyl radicals, C1-C2 alkoxy radicals, C2-C4 (poly)hydroxyalkoxy radicals, amino radicals, C1-C2 (di)alkylamino radicals, carboxyl radicals, and sulfonic radicals;
- and optionally substituted phenyl radicals;
- R10 and R11, which may be identical or different, are chosen from hydrogen atoms, optionally substituted phenyl radicals, carboxyl radicals, sulfonylamino radicals, and C1-C4 alkyl radicals optionally substituted with at least one radical chosen from hydroxyl radicals, C1-C2 alkoxy radicals, C2-C4 (poly)hydroxyalkoxy radicals, amino radicals, C1-C2 (di)alkylamino radicals, carboxyl radicals, and sulfonic radicals;
- R6, R7, R8 and R9, which may be identical or different, are chosen from hydrogen atoms;
- chlorine atoms;
- bromine atoms;
- linear and branched C1-C6 hydrocarbonaceous chains, wherein each of said C1-C6 hydrocarbonaceous chains can form at least one saturated or unsaturated 3- to 6-membered carbonaceous ring, wherein at least one carbon atom of each of said C1-C6 hydrocarbonaceous chains is optionally replaced by an entity chosen from an oxygen atom, a nitrogen atom, a sulfur atom, and SO2 groups and further wherein at least one carbon atom of each of said C1-C6 hydrocarbonaceous chains can be optionally substituted by at least one halogen atom, provided that R6, R7, R8, and R9, which may be identical or different, are not chosen from peroxide bonds, diazo radicals, and nitroso radicals;
- n is an integer chosen from 1 and 2;
- Z4 is chosen from an oxygen atom, a sulfur atom, NR2 radicals, and CR2R2′ radicals;
- R0, R1, R2, R2′, R3, R4 and R5, which may be identical or different, are chosen from hydrogen atoms;
- alkyl radicals;
- alkoxy radicals;
- hydroxyl radicals;
- amino radicals;
- acetoxy radicals;
- NR14R15 groups wherein R14 and R15, which may be identical or different, are chosen from hydrogen atoms and C1-C4 alkyl radicals substituted with at least one radical chosen from halogen atoms, hydroxyl radicals, C1-C2 alkoxy radicals, amino radicals, and C1-C2 amino(di)alkyl radicals;
- sulfonylamino radicals;
- carboxyl radicals;
- carboxamido radicals;
- amido radicals;
- monoalkylamido radicals;
- dialkylamido radicals;
- halogen radicals;
- and C1-C6 alkyl radicals substituted with at least one radical chosen from hydroxyl radicals, C1-C2 alkoxy radicals, C2-C4 (poly)hydroxyalkoxy radicals, amino radicals and C1-C2 (di)alkylamino radicals;
- and
- X is chosen from organic anions and inorganic anions.
A process for the oxidation dyeing of keratinous fibers comprising applying to said keratinous fibers, in the presence of at least one oxidizing agent, at least one dyeing composition comprising at least one oxidation base and optionally at least one coupler,and further comprising at least one cationic azo dye of formula (I):
- W1-N═N-W2-W3 (I)
- wherein:
- W1is chosen from 5-membered cationic aromatic heterocycles of formula (II):
- W2 is chosen from divalent carbonaceous aromatic groups and pyridine groups chosen from groups of formulae (III) and (IV):
- W3 is chosen from 7-membered or 8-membered heterocycles of formula (V):
- wherein:
- Z1 is chosen from oxygen and sulfur atoms, and NR12 radicals;
- Z2 is chosen from a nitrogen atom and CR11 radicals;
- R12 and R13, which may be identical or different, are chosen from C1-C8 alkyl radicals optionally substituted with at least one radical chosen from hydroxyl radicals, C1-C2 alkoxy radicals, C2-C4 (poly)hydroxyalkoxy radicals, amino radicals, C1-C2 (di)alkylamino radicals, carboxyl radicals, and sulfonic radicals;
- and optionally substituted phenyl radicals;
- R10 and R11, which may be identical or different, are chosen from hydrogen atoms, optionally substituted phenyl radicals, carboxyl radicals, sulfonylamino radicals, and C1-C4 alkyl radicals optionally substituted with at least one radical chosen from hydroxyl radicals, C1-C2 alkoxy radicals, C2-C4 (poly)hydroxyalkoxy radicals, amino radicals, C1-C2 (di)alkylamino radicals, carboxyl radicals, and sulfonic radicals;
- R6, R7, R8 and R9, which may be identical or different, are chosen from hydrogen atoms;
- chlorine atoms;
- bromine atoms;
- linear and branched C1-C6 hydrocarbonaceous chains, wherein each of said C1-C6 hydrocarbonaceous chains can form at least one saturated or unsaturated, 3- to 6-membered carbonaceous ring, wherein at least one carbon atom of each of said C1-C6 hydrocarbonaceous chains is optionally replaced by an entity chosen from an oxygen atom, a nitrogen atom, a sulfur atom, and an SO2 radical, and further wherein at least one carbon atom of each of said C1-C6 hydrocarbonaceous chains can be optionally substituted by at least one halogen atom, provided that R6, R7, R8, and R9, which may be identical or different, are not chosen from peroxide bonds, diazo radicals, and nitroso radicals;
- n is an integer chosen from 1 and 2;
- Z4 is chosen from an oxygen atom, a sulfur atom, NR2 radicals, and CR2R2′ radicals;
- R0, R1, R2, R2′, R3, R4 and R5, which may be identical or different, are chosen from hydrogen atoms;
- alkyl radicals;
- alkoxy radicals;
- hydroxyl radicals;
- amino radicals;
- acetoxy radicals;
- NR14R15 groups wherein R14 and R15, which may be identical or different, are chosen from hydrogen atoms and C1-C4 alkyl radicals substituted with at least one radical chosen from halogen atoms, hydroxyl radicals, C1-C2 alkoxy radicals, amino radicals, and C1-C2 amino(di)alkyl radicals;
- sulfonylamino radicals;
- carboxyl radicals;
- carboxamido radicals;
- amido radicals;
- monoalkylamido radicals;
- dialkylamido radicals;
- halogen radicals;
- and C1-C6 alkyl radicals substituted with at least one radical chosen from hydroxyl radicals, C1-C2 alkoxy radicals, C2-C4 (poly)hydroxyalkoxy radicals, amino radicals and C1-C2 (di)alkylamino radicals;
- and
- X is chosen from organic anions and inorganic anions.
A multi-compartment dyeing device comprising at least one compartment comprising at least one dyeing composition for keratinous fibers and at least one compartment comprising at least one oxidizing composition,
- wherein said dyeing composition comprises at least one cationic azo dye of formula (I):
- W1—N═N—W2—W3 (I);
- wherein:
- W1 is chosen from 5-membered cationic aromatic heterocycles of formula (II):
- W2 is chosen from divalent carbonaceous aromatic groups and pyridine groups chosen from groups of formulae (III) and (IV):
- W3 is chosen from 7-membered or 8-membered heterocycles of formula (V):
- wherein:
- Z1 is chosen from oxygen and sulfur atoms, and NR12 radicals;
- Z2 is chosen from a nitrogen atom and CR11 radicals;
- R12 and R13, which may be identical or different, are chosen from C1-C8 alkyl radicals optionally substituted with at least one radical chosen from hydroxyl radicals, C1-C2 alkoxy radicals, C2-C4 (poly)hydroxyalkoxy radicals, amino radicals, C1-C2 (di)alkylamino radicals, carboxyl radicals, and sulfonic radicals;
- and optionally substituted phenyl radicals;
- R10 and R11, which may be identical or different, are chosen from hydrogen atoms, optionally substituted phenyl radicals, carboxyl radicals, sulfonylamino radicals, and C1-C4 alkyl radicals that are optionally substituted with at least one radical chosen from hydroxyl radicals, C1-C2 alkoxy radicals, C2-C4 (poly)hydroxyalkoxy radicals, amino radicals, C1-C2 (di)alkylamino radicals, carboxyl radicals, and sulfonic radicals;
- R6, R7, R8 and R9, which may be identical or different, are chosen from hydrogen atoms;
- chlorine atoms;
- bromine atoms;
- linear and branched C1-C6 hydrocarbonaceous chains, wherein each of said C1-C6 hydrocarbonaceous chains can form at least one saturated or unsaturated, 3- to 6-membered carbonaceous ring, wherein at least one carbon atom of each of said C1-C6 hydrocarbonaceous chains is optionally replaced by an entity chosen from an oxygen atom, a nitrogen atom, a sulfur atom, and an SO2 radical and further wherein at least one carbon atom of each of said C1-C6 hydrocarbonaceous chains can be optionally substituted by at least one halogen atom, provided that R6, R7, R8, and R9, which may be identical or different, are not chosen from peroxide bonds, diazo radicals, and nitroso radicals;
- n is an integer chosen from 1 and 2;
- Z4 is chosen from an oxygen atom, a sulfur atom, NR2 radicals, and CR2R2′ radicals;
- R0, R1, R2, R2′, R3, R4 and R5, which may be identical or different, are chosen from hydrogen atoms;
- alkyl radicals;
- alkoxy radicals;
- hydroxyl radicals;
- amino radicals;
- acetoxy radicals;
- NR14R15 groups wherein R14 and R15, which may be identical or different, are chosen from hydrogen atoms and C1-C4 alkyl radicals substituted with at least one radical chosen from halogen atoms, hydroxyl radicals, C1-C2 alkoxy radicals, amino radicals, and C1-C2 amino(di)alkyl radicals;
- sulfonylamino radicals;
- carboxyl radicals;
- carboxamido radicals;
- amido radicals;
- monoalkylamido radicals;
- dialkylamido radicals;
- halogen radicals;
- and C1-C6 alkyl radicals substituted with at least one radical chosen from hydroxyl radicals, C1-C2 alkoxy radicals, C2-C4 (poly)hydroxyalkoxy radicals, amino radicals and C1-C2 (di)alkylamino radicals;
- and
- X is chosen from organic anions and inorganic anions.
A cationic azo compound chosen from compounds of formula (I):
- W1—N═N—W2—W3 (I)
- wherein:
- W1 is chosen from 5-membered cationic aromatic heterocycles of formula (II):
- W2 is chosen from divalent carbonaceous aromatic groups and pyridine groups chosen from groups of formulae (III) and (IV):
- W3 is chosen from 7-membered or 8-membered heterocycles of formula (V):
- wherein:
- Z1 is chosen from oxygen and sulfur atoms, and NR12 radicals;
- Z2 is chosen from a nitrogen atom and CR11 radicals;
- R12 and R13, which may be identical or different, are chosen from C1-C8 alkyl radicals optionally substituted with at least one radical chosen from hydroxyl radicals, C1-C2 alkoxy radicals, C2-C4 (poly)hydroxyalkoxy radicals, amino radicals, C1-C2 (di)alkylamino radicals, carboxyl radicals, and sulfonic radicals;
- and optionally substituted phenyl radicals;
- R10 and R11, which may be identical or different, are chosen from hydrogen atoms, optionally substituted phenyl radicals, carboxyl radicals, sulfonylamino radicals, and C1-C4 alkyl radicals optionally substituted with at least one radical chosen from hydroxyl radicals, C1-C2 alkoxy radicals, C2-C4 (poly)hydroxyalkoxy radicals, amino radicals, C1-C2 (di)alkylamino radicals, carboxyl radicals, and sulfonic radicals;
- R6, R7, R8 and R9, which may be identical or different, are chosen from hydrogen atoms;
- chlorine atoms;
- bromine atoms;
- linear and branched C1-C6 hydrocarbonaceous chains, wherein each of said C1-C6 hydrocarbonaceous chains can form at least one saturated or unsaturated, 3- to 6-membered carbonaceous ring, wherein at least one carbon atom of each of said C1-C6 hydrocarbonaceous chains is optionally replaced by an entity chosen from an oxygen atom, a nitrogen atom, a sulfur atom, and an SO2 radical and further wherein at least one carbon atom of each of said C1-C6 hydrocarbonaceous chains can be optionally substituted by at least one halogen atom, provided that R6, R7, R8, and R9, which may be identical or different, are not chosen from peroxide bonds, diazo radicals, and nitroso radicals;
- n is an integer chosen from 1 and 2;
- Z4 is chosen from an oxygen atom, a sulfur atom, NR2 radicals, and CR2R2′ radicals;
- R0, R1, R2, R2′, R3, R4 and R5, which may be identical or different, are chosen from hydrogen atoms;
- alkyl radicals;
- alkoxy radicals;
- hydroxyl radicals;
- amino radicals;
- acetoxy radicals;
- NR4R15 groups wherein R14 and R15, which may be identical or different, are chosen from hydrogen atoms and C1-C4 alkyl radicals substituted with at least one radical chosen from halogen atoms, hydroxyl radicals, C1-C2 alkoxy radicals, amino radicals, and C1-C2 amino(di)alkyl radicals;
- sulfonylamino radicals;
- carboxyl radicals;
- carboxamido radicals;
- amido radicals;
- monoalkylamido radicals;
- dialkylamido radicals;
- halogen radicals;
- and C1-C6 alkyl radicals substituted with at least one radical chosen from hydroxyl radicals, C1-C2 alkoxy radicals, C2-C4 (poly)hydroxyalkoxy radicals, amino radicals and C1-C2 (di)alkylamino radicals;
- and
- X is chosen from organic anions and inorganic anions.
Dependencies are inferred from the claim text.