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US 6,884,266 B2Granted
Dyeing composition for dyeing keratinous fibers comprising a cationic azo-dye
AssigneeL'oreal
InventorsLaurent Vidal, Madeleine Leduc
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—NW3W4, and 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):
- wherein
- W1 is a 5-membered cationic aromatic heterocycle of the following formula (II)
- W2 is chosen from divalent aromatic carbonaceous and pyridine groups of the following formulae (III) and (IV):
- in which formulae (II) to (IV)
- Z1 is chosen from an oxygen atom, a sulfur atom and a radical N(R4),
- Z2 is chosen from a nitrogen atom and a radical C(R3),
- R1 and R4, which may be identical or different, are chosen from C1-C8 alkyl radicals optionally substituted by 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, sulfonic radicals, and optionally substituted phenyl radicals,
- R2 and R3, which may be identical or different, are chosen from a hydrogen atom;
- C1-C4 alkyl radicals, optionally substituted by at least one radical chosen from hydroxyl radicals, C1-C2 alkoxy radicals, C2-C4 (poly)hydroxyalkoxy radicals, amino radicals, C1-C2 (di)alkylamino radicals;
- sulfonic radicals;
- optionally substituted phenyl radicals;
- carboxyl radicals;
- and sulfonylamino radicals,
- R5, R6, R7, R8, and W4, which may be identical or different, are chosen from hydrogen atoms;
- chlorine atoms;
- bromine atoms;
- linear and branched C1-C6 hydrocarbonaceous chains which may form at least one 3- to 6-membered carbonaceous ring, and which may be saturated or unsaturated, and wherein at least one carbon atom of the hydrocarbonaceous chain may be replaced by an entity chosen from an oxygen atom, a nitrogen atom, a sulfur atom, and a SO2 group, and the carbon atoms of which may be identical or different due to substitution by at least one halogen atom;
- with the proviso that R5, R6, R7, R8, and W4 are not chosen from a peroxide bond or from diazo and nitroso radicals, and wherein W4 is a nonaromatic substituent,
- W3 is a heteroaromatic ring chosen from thienyl, pyrazolyl, pyrrolyl, imidazolyl, furyl, triazolyl, thiadiazolyl, isoxazolyl, isothiazolyl, thiazolyl, oxazolyl, pyridyl, pyrimidinyl, triazinyl, pyridazinyl, and pyrazinyl rings, wherein the heteroaromatic rings are optionally substituted by at least one C1-C6 alkyl radical, optionally substituted by at least one radical chosen from hydroxyl radicals, C1-C4 alkoxy radicals, (poly)hydroxyalkoxy radicals, amino radicals, C1-C4 (di)alkylamino radicals, C2-C4 (poly)hydroxyalkylamino radicals, carboxyl radicals, sulfonyl radicals, alkoxycarbonyl radicals, and C1-C4 thioether radicals;
- phenyl radicals optionally substituted by at least one radical chosen from C1-C2 alkoxy radicals, amino radicals, C1-C2 (di)alkylamino radicals, carboxyl radicals, sulfonyl radicals, C1-C4 alkyl radicals, halogen atoms, and C1-C2 thioether radicals;
- halogen atoms;
- amino radicals;
- C1-C4 alkylamino radicals;
- C2-C4 (poly)hydroxyalkylamino radicals, C1-C4 (di)alkylamino radicals;
- C1-C2 alkoxy radicals;
- carboxyl radicals;
- and sulfonylamino radicals,
- X is an organic or inorganic anion.
25 more elements
A process for the oxidation dyeing of keratinous fibers, comprising applying to said keratinous fibers a dyeing composition comprising at least one cationic azo dye of formula (I):
- wherein
- W1 is a 5-membered cationic aromatic heterocycle of the following formula (II)
- W2 is chosen from divalent aromatic carbonaceous and pyridine groups of the following formulae (III) and (IV):
- in which formulae (II) to (IV)
- Z1 is chosen from an oxygen atom, a sulfur atom and a radical N(R4),
- Z2 is chosen from a nitrogen atom and a radical C(R3),
- R1 and R4, which may be identical or different, are chosen from C1-C8 alkyl radicals optionally substituted by 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, sulfonic radicals, and optionally substituted phenyl radicals,
- R2 and R3, which may be identical or different, are chosen from a hydrogen atom;
- C1-C4 alkyl radicals, optionally substituted by at least one radical chosen from hydroxyl radicals, C1-C2 alkoxy radicals, C2-C4 (poly)hydroxyalkoxy radicals, amino radicals, C1-C2 (di)alkylamino radicals;
- sulfonic radicals;
- optionally substituted phenyl radicals;
- carboxyl radicals;
- and sulfonylamino radicals,
- R5, R6, R7, R8, and W4, which may be identical or different, are chosen from hydrogen atoms;
- chlorine atoms;
- bromine atoms;
- linear and branched C1-C6 hydrocarbonaceous chains which may form at least one 3- to 6-membered carbonaceous ring, and which may be saturated or unsaturated, and wherein at least one carbon atom of the hydrocarbonaceous chain may be replaced by an entity chosen from an oxygen atom, a nitrogen atom, a sulfur atom, and a SO2 group, and the carbon atoms of which may be identical or different due to substitution by at least one halogen atom;
- with the proviso that R5, R6, R7, R8, and W4 are not chosen from a peroxide bond or from diazo and nitroso radicals, and wherein and W4 is a nonaromatic substituent,
- W3 is a heteroaromatic ring chosen from thienyl, pyrazolyl, pyrrolyl, imidazolyl, furyl, triazolyl, thiadiazolyl, isoxazolyl, isothiazolyl, thiazolyl, oxazolyl, pyridyl, pyrimidinyl, triazinyl, pyridazinyl, and pyrazinyl rings, wherein the heteroaromatic rings are optionally substituted by at least one C1-C6 alkyl radical, optionally substituted by at least one radical chosen from hydroxyl radicals, C1-C4 alkoxy radicals, (poly)hydroxyalkoxy radicals, amino radicals, C1-C4 (di)alkylamino radicals, C2-C4 (poly)hydroxyalkylamino radicals, carboxyl radicals, sulfonyl radicals, alkoxycarbonyl radicals, and C1-C4 thioether radicals;
- phenyl radicals optionally substituted by at least one radical chosen from C1-C2 alkoxy radicals, amino radicals, C1-C2 (di)alkylamino radicals, carboxyl radicals, sulfonyl radicals, C1-C4 alkyl radicals, halogen atoms, and C1-C2 thioether radicals;
- halogen atoms;
- amino radicals;
- C1-C4 alkylamino radicals;
- C2-C4 (poly)hydroxyalkylamino radicals, C1-C4 (di)alkylamino radicals;
- C1-C2 alkoxy radicals;
- carboxyl radicals;
- and sulfonylamino radicals, and
- X is an organic or inorganic anion.
25 more elements
A process for the oxidation dyeing of keratinous fibers comprising applying to said keratinous fibers a composition comprising at least one dyeing composition, at least one oxidation base, and optionally at least one coupler, in the presence of at least one oxidizing agent,
- wherein said dyeing composition comprises at least one cationic azo dye of formula (I):
- wherein
- W1 is a 5-membered cationic aromatic heterocycle of the following formula (II)
- W2 is chosen from divalent aromatic carbonaceous and pyridine groups of the following formulae (III) and (IV):
- in which formulae (II) to (IV)
- Z1 is chosen from an oxygen atom, a sulfur atom and a radical N(R4),
- Z2 is chosen from a nitrogen atom and a radical C(R3),
- R1 and R4, which may be identical or different, are chosen from C1-C8 alkyl radicals optionally substituted by 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, sulfonic radicals, and optionally substituted phenyl radicals,
- R2 and R3, which may be identical or different, are chosen from a hydrogen atom;
- C1-C4 alkyl radicals, optionally substituted by at least one radical chosen from hydroxyl radicals, C1-C2 alkoxy radicals, C2C4 (poly)hydroxyalkoxy radicals, amino radicals, C1-C2 (di)alkylamino radicals;
- sulfonic radicals;
- optionally substituted phenyl radicals;
- carboxyl radicals;
- and sulfonylamino radicals,
- R5, R6, R7, R8, and W4, which may be identical or different, are chosen from hydrogen atoms;
- chlorine atoms;
- bromine atoms;
- linear and branched C1-C6 hydrocarbonaceous chains which may form at least one 3- to 6-membered carbonaceous ring, and which may be saturated or unsaturated, and wherein at least one carbon atom of the hydrocarbonaceous chain may be replaced by an entity chosen from an oxygen atom, a nitrogen atom, a sulfur atom, and a SO2 group, and the carbon atoms of which may be identical or different due to substitution by at least one halogen atom;
- with the proviso that R5, R6, R7, R8, and W4 are not chosen from a peroxide bond or from diazo and nitroso radicals, and wherein and W4 is a nonaromatic substituent,
- W3 is a heteroaromatic ring chosen from thienyl, pyrazolyl, pyrrolyl, imidazolyl, furyl, triazolyl, thiadiazolyl, isoxazolyl, isothiazolyl, thiazolyl, oxazolyl, pyridyl, pyrimidinyl, triazinyl, pyridazinyl, and pyrazinyl rings, wherein the heteroaromatic rings are optionally substituted by at least one C1-C6 alkyl radical, optionally substituted by at least one radical chosen from hydroxyl radicals, C1-C4 alkoxy radicals, (poly)hydroxyalkoxy radicals, amino radicals, C1-C4 (di)alkylamino radicals, C2-C4 (poly)hydroxyalkylamino radicals, carboxyl radicals, sulfonyl radicals, alkoxycarbonyl radicals, and C1-C4 thioether radicals;
- phenyl radicals optionally substituted by at least one radical chosen from C1-C2 alkoxy radicals, amino radicals, C1-C2 (di)alkylamino radicals, carboxyl radicals, sulfonyl radicals, C1-C4 alkyl radicals, halogen atoms, and C1-C2 thioether radicals;
- halogen atoms;
- amino radicals;
- C1-C4 alkylamino radicals;
- C2-C4 (poly)hydroxyalkylamino radicals, C1-C4 (di)alkylamino radicals;
- C1-C2 alkoxy radicals;
- carboxyl radicals;
- and sulfonylamino radicals, and
- X is an organic or inorganic anion.
26 more elements
A multi-compartment dyeing device comprising:
- at least one compartment comprising a composition comprising at least
- one cationic azo dye of formula (I):
- wherein
- W1 is a 5-membered cationic aromatic heterocycle of the following formula (II)
- W2 is chosen from divalent aromatic carbonaceous and pyridine groups of the following formulae (III) and (IV):
- in which formulae (II) to (IV)
- Z1 is chosen from an oxygen atom, a sulfur atom and a radical N(R4),
- Z2 is chosen from a nitrogen atom and a radical C(R3),
- R1 and R4, which may be identical or different, are chosen from C1-C8 alkyl radicals optionally substituted by 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, sulfonic radicals, and optionally substituted phenyl radicals,
- R2 and R3, which may be identical or different, are chosen from a hydrogen atom;
- C1-C4 alkyl radicals, optionally substituted by at least one radical chosen from hydroxyl radicals, C1-C2 alkoxy radicals, C2-C4 (poly)hydroxyalkoxy radicals, amino radicals, C1-C2 (di)alkylamino radicals;
- sulfonic radicals;
- optionally substituted phenyl radicals;
- carboxyl radicals;
- and sulfonylamino radicals,
- R5, R6, R7, R8, and W4, which may be identical or different, are chosen from hydrogen atoms;
- chlorine atoms;
- bromine atoms;
- linear and branched C1-C6 hydrocarbonaceous chains which may form at least one 3- to 6-membered carbonaceous ring, and which may be saturated or unsaturated, and wherein at least one carbon atom of the hydrocarbonaceous chain may be replaced by an entity chosen from an oxygen atom, a nitrogen atom, a sulfur atom, and a SO2 group, and the carbon atoms of which may be identical or different due to substitution by at least one halogen atom;
- with the proviso that R5, R6, R7, R8, and W4 are not chosen from a peroxide bond or from diazo and nitroso radicals, and wherein and W4 is a nonaromatic substituent,
- W3 is a heteroaromatic ring chosen from thienyl, pyrazolyl, pyrrolyl, imidazolyl, furyl, triazolyl, thiadiazolyl, isoxazolyl, isothiazolyl, thiazolyl, oxazolyl, pyridyl, pyrimidinyl, triazinyl, pyridazinyl, and pyrazinyl rings, wherein the heteroaromatic rings are optionally substituted by at least one C1-C6 alkyl radical, optionally substituted by at least one radical chosen from hydroxyl radicals, C1-C4 alkoxy radicals, (poly)hydroxyalkoxy radicals, amino radicals, C1-C4 (di)alkylamino radicals, C2-C4 (poly)hydroxyalkylamino radicals, carboxyl radicals, sulfonyl radicals, alkoxycarbonyl radicals, and C1-C4 thioether radicals;
- phenyl radicals optionally substituted by at least one radical chosen from C1-C2 alkoxy radicals, amino radicals, C1-C2 (di)alkylamino radicals, carboxyl radicals, sulfonyl radicals, C1-C4 alkyl radicals, halogen atoms, and C1-C2 thioether radicals;
- halogen atoms;
- amino radicals;
- C1-C4 alkylamino radicals;
- C2-C4 (poly)hydroxyalkylamino radicals, C1-C4 (di)alkylamino radicals;
- C1-C2 alkoxy radicals;
- carboxyl radicals;
- and sulfonylamino radicals, and
- X is an organic or inorganic anion, and
- at least one other compartment comprising an oxidizing composition.
28 more elements
A cationic azo dye of formula (I):
- wherein
- W1 is a 5-membered cationic aromatic heterocycle of the following formula (II)
- W2 is chosen from divalent aromatic carbonaceous and pyridine groups of the following formulae (III) and (IV):
- 10 in which formulae (II) to (IV)
- Z1 is chosen from an oxygen atom, a sulfur atom and a radical N(R4),
- Z2 is chosen from a nitrogen atom and a radical C(R3),
- R1 and R4, which may be identical or different, are chosen from C1-C8 alkyl radicals optionally substituted by 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, sulfonic radicals, and optionally substituted phenyl radicals,
- R2 and R3, which may be identical or different, are chosen from a hydrogen atom;
- C1-C4 alkyl radicals, optionally substituted by at least one radical chosen from hydroxyl radicals, C1-C2 alkoxy radicals, C2-C4 (poly)hydroxyalkoxy radicals, amino radicals, C1-C2 (di)alkylamino radicals;
- sulfonic radicals;
- optionally substituted phenyl radicals;
- carboxyl radicals;
- and sulfonylamino radicals,
- R5, R6, R7, R8, and W4, which may be identical or different, are chosen from hydrogen atoms;
- chlorine atoms;
- bromine atoms;
- linear and branched C1-C5 hydrocarbonaceous chains which may form at least one 3- to 6-membered carbonaceous ring, and which may be saturated or unsaturated, and wherein at least one carbon atom of the hydrocarbonaceous chain may be replaced by an entity chosen from an oxygen atom, a nitrogen atom, a sulfur atom, and a SO2 group, and the carbon atoms of which may be identical or different due to substitution by at least one halogen atom;
- with the proviso that R5, R6, R7, R8, and W4 are not chosen from a peroxide bond or from diazo and nitroso radicals, and wherein and W4 is a nonaromatic substituent,
- W3 is a heteroaromatic ring chosen from thienyl, pyrazolyl, pyrrolyl, imidazolyl, furyl, triazolyl, thiadiazolyl, isoxazolyl, isothiazolyl, thiazolyl, oxazolyl, pyridyl, pyrimidinyl, triazinyl, pyridazinyl, and pyrazinyl rings, wherein the heteroaromatic rings are optionally substituted by at least one C1-C6 alkyl radical, optionally substituted by at least one radical chosen from hydroxyl radicals, C1-C4 alkoxy radicals, (poly)hydroxyalkoxy radicals, amino radicals, C1-C4 (di)alkylamino radicals, C2-C4 (poly)hydroxyalkylamino radicals, carboxyl radicals, sulfonyl radicals, alkoxycarbonyl radicals, and C1-C4 thioether radicals;
- phenyl radicals optionally substituted by at least one radical chosen from C1-C2 alkoxy radicals, amino radicals, C1-C2 (di)alkylamino radicals, carboxyl radicals, sulfonyl radicals, C1-C4 alkyl radicals, halogen atoms, and C1-C2 thioether radicals;
- halogen atoms;
- amino radicals;
- C1-C4 alkylamino radicals;
- C2-C4 (poly)hydroxyalkylamino radicals, C1-C4 (di)alkylamino radicals;
- C1-C2 alkoxy radicals;
- carboxyl radicals;
- and sulfonylamino radicals, and
- X is an organic or inorganic anion.
25 more elements
Dependencies are inferred from the claim text.