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US 7,022,143 B2Granted
Dyeing composition for dyeing keratinous fibers comprising a cationic azo-dye
AssigneeL'oreal
InventorsLaurent Vidal, Aziz Fadli
Life of this patent
Estimating the term…
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).
Claims34
A composition for dyeing keratinous fibers comprising at least one cationic azo dye of the following formula (I):
- W1—N═N—W2—W3 (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 (Ill) and (IV)
- W3 is chosen from 5- and 6-membered heterocycles of the following formula (V)
- in which formulae (II) to (V):
- Z1 is chosen from an oxygen atom, a sulfur atom and a radical N(R12),
- Z2 is chosen from a nitrogen atom and a radical C(R11),
- R9 and R12, which may be identical or different, are chosen from C1-C8 alkyl radicals, optionally substituted by at least one radical chosen from hydroxyl, C1-C2 alkoxy, C2-C4 (poly)hydroxyalkoxy, amino, C1-C2 (di)alkylamino, carboxyl, and sulfonic radicals;
- and optionally substituted phenyl radicals,
- R10 and R11, 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, C1-C2 alkoxy, C2-C4 (poly)hydroxyalkoxy, amino, C1-C2 (di)alkylamino, carboxyl, and sulfonic radicals;
- optionally substituted phenyl radicals;
- carboxyl radicals;
- and sulfonylamino radicals,
- R5, R6, R7, and R8, which may be identical or different, are chosen from a hydrogen atom;
- a chlorine atom;
- a bromine atom;
- 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, of which at least one carbon atom of the carbonaceous chain can be replaced by an entity chosen from oxygen, nitrogen, and sulfur atoms and from an 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, and R8 are not chosen from a peroxide bond or from diazo and nitroso radicals,
- n is an integer equal to 0 or 1,
- R0, R1, R2, R3, and R4, which may be the same or different, are chosen from a hydrogen atom;
- hydroxyl radicals;
- amino radicals;
- acetoxy radicals;
- a group —N(R13)(R14), where R13 and R14, which may be identical or different, are chosen from a hydrogen atom and C1-C4 alkyl radicals substituted by at least one radical chosen from halogen atoms and from hydroxyl, C1-C2 alkoxy, amino, and C1-C2 amino(di)alkyl radicals;
- sulfonylamino radicals;
- carboxyl radicals;
- carboxamido radicals;
- amido radicals;
- mono- and dialkylamido radicals;
- halogen radicals;
- and C1-C6 alkyl radicals substituted by at least one radical chosen from hydroxyl, C1-C2 alkoxy, C2-C4 (poly)hydroxyalkoxy, amino, and C1-C2 (di)alkylamino radicals,
- with the proviso that at least one of the groups R0, R1, R2, R3, and R4 is not hydrogen, and
- X is chosen from organic and inorganic anions.
31 more elements
A process for the oxidation dyeing of keratinous fibers, comprising applying to said keratinous fibers at least one dyeing composition for keratinous fibers comprising at least one cationic azo dye of the following formula (I):
- W1—N═N—W2—W3 (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)
- W3 is chosen from 5- and 6-membered heterocycles of the following formula (V)
- in which formulae (II) to (V):
- Z1 is chosen from an oxygen atom, a sulfur atom and a radical N(R12),
- Z2 is chosen from a nitrogen atom and a radical C(R11),
- R9 and R12, which may be identical or different, are chosen from C1-C8 alkyl radicals, optionally substituted by at least one radical chosen from hydroxyl, C1-C2 alkoxy, C2-C4 (poly)hydroxyalkoxy , amino, C1-C2 (di)alkylamino, carboxyl, and sulfonic radicals;
- and optionally substituted phenyl radicals,
- R10 and R11, 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, C1C2 alkoxy, C2-C4 (poly)hydroxyalkoxy, amino, C1-C2 (di)alkylamino, carboxyl, and sulfonic radicals;
- optionally substituted phenyl radicals;
- carboxyl radicals;
- and sulfonylamino radicals;
- R5, R6, R7, and R8, which may be identical or different, are chosen from a hydrogen atom;
- a chlorine atom;
- a bromine atom;
- 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, of which at least one carbon atom of the carbonaceous chain can be replaced by an entity chosen from oxygen, nitrogen and sulfur atoms and from an 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, and R8 are not chosen from a peroxide bond or from diazo and nitroso radicals,
- n is an integer equal to 0 or 1,
- R0, R1, R2, R3, and R4, which may be the same or different, are chosen from a hydrogen atom;
- hydroxyl radicals;
- amino radicals;
- acetoxy radicals;
- a group —N(R13)(R14), where R13 and R14, which may be identical or different, are chosen from a hydrogen atom, C1-C4 alkyl radicals substituted by at least one radical chosen from halogen atoms, and hydroxyl, C1-C2 alkoxy, amino, and C1-C2 amino(di)alkyl radicals;
- sulfonylamino radicals;
- carboxyl radicals;
- carboxamido radicals;
- amido radicals;
- mono- and dialkylamido radicals;
- halogen radicals;
- C1-C6 alkyl radicals substituted by at least one radical chosen from hydroxyl , C1-C2 alkoxy, C2-C4 (poly)hydroxyalkoxy, amino, and C1-C2 (di)alkylamino radicals,
- with the proviso that at least one of the groups R0, R1, R2, R3, and R4 is not hydrogen, and
- X is chosen from organic and inorganic anions.
31 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 at least one dyeing composition comprises at least one cationic azo dye of the following formula (I):
- W1—N═N—W2—W3 (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)
- W3 is chosen from 5- and 6-membered heterocycles of the following formula (V)
- in which formulae (II) to (V):
- Z1 is chosen from an oxygen atom, a sulfur atom and a radical N(R12),
- Z2 is chosen from a nitrogen atom and a radical C(R11),
- R9 and R12, which may be identical or different, are chosen from C1-C8 alkyl radicals, optionally substituted by at least one radical chosen from hydroxyl, C1-C2 alkoxy, C2-C4 (poly)hydroxyalkoxy, amino, C1-C2 (di)alkylamino, carboxyl, and sulfonic radicals;
- and optionally substituted phenyl radicals,
- R10 and R11, 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, C1-C2 alkoxy, C2-C4 (poly)hydroxyalkoxy, amino, C1-C2 (di)alkylamino, carboxyl, and sulfonic radicals;
- optionally substituted phenyl radicals;
- carboxyl radicals;
- and sulfonylamino radicals,
- R5, R6, R7, and R8, which may be identical or different, are chosen from a hydrogen atom;
- a chlorine atom;
- a bromine atom;
- 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, of which at least one carbon atom of the carbonaceous chain can be replaced by an entity chosen from oxygen, nitrogen, and sulfur atoms and from an 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, and R8 are not chosen from a peroxide bond or from diazo and nitroso radicals,
- n is an integer equal to 0 or 1,
- R0, R1, R2, R3, and R4, which may be the same or different, are chosen from a hydrogen atom;
- hydroxyl radicals;
- amino radicals;
- acetoxy radicals;
- a group —N(R13)(R14), where R13 and R14, which may be identical or different, are chosen from a hydrogen atom and C1-C4 alkyl radicals substituted by at least one radical chosen from halogen atoms, and hydroxyl, C1-C2 alkoxy, amino, and C1-C2 amino(di)alkyl radicals;
- sulfonylamino radicals;
- carboxyl radicals;
- carboxamido radicals;
- amido radicals;
- mono- and dialkylamido radicals;
- halogen radicals;
- C1-C6 alkyl radicals substituted by 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,
- with the proviso that at least one of the groups R0, R1, R2, R3, and R4 is not hydrogen, and
- X is chosen from organic and inorganic anions.
31 more elements
A multi-compartment dyeing device comprising:
- at least one first compartment comprising a dyeing composition and at least one second compartment comprising an oxidizing composition, wherein said dyeing composition comprises at least one cationic azo dye of the following formula (I):
- W1—N═N—W2—W3 (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)
- W3 is chosen from 5- and 6-membered heterocycles of the following formula (V)
- in which formulae (II) to (V):
- Z1 is chosen from an oxygen atom, a sulfur atom and a radical N(R12),
- Z2 is chosen from a nitrogen atom and a radical C(R11),
- R9 and R12, which may be identical or different, are chosen from C1-C8 alkyl radicals, optionally substituted by at least one radical chosen from hydroxyl, C1-C2 alkoxy, C2-C4 (poly)hydroxyalkoxy, amino, C1-C2 (di)alkylamino, carboxyl, and sulfonic radicals;
- and optionally substituted phenyl radicals,
- R10 and R11, 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, C1-C2 alkoxy, C2-C4 (poly)hydroxyalkoxy, amino, C1-C2 (di)alkylamino, carboxyl, and sulfonic radicals;
- optionally substituted phenyl radicals;
- carboxyl radicals;
- and sulfonylamino radicals,
- R5, R6, R7, and R8, which may be identical or different, are chosen from a hydrogen atom;
- a chlorine atom;
- a bromine atom;
- 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, of which at least one carbon atom of the carbonaceous chain can be replaced by an entity chosen from oxygen, nitrogen, and sulfur atoms and from an 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, and R8 are not chosen from a peroxide bond or from diazo and nitroso radicals,
- n is an integer equal to 0 or 1,
- R0, R1, R2, R3, and R4, which may be the same or different, are chosen from a hydrogen atom;
- hydroxyl radicals;
- amino radicals;
- acetoxy radicals;
- a group —N(R13)(R14), where R13 and R14, which may be identical or different, are chosen from a hydrogen atom and C1-C4 alkyl radicals substituted by at least one radical chosen from halogen atoms, and hydroxyl, C1-C2 alkoxy, amino, and C1-C2 amino(di)alkyl radicals;
- sulfonylamino radicals;
- carboxyl radicals;
- carboxamido radicals;
- amido radicals;
- mono- and dialkylamido radicals;
- halogen radicals;
- C1-C6 alkyl radicals substituted by 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,
- with the proviso that at least one of the groups R0, R1, R2, R3, and R4 is not hydrogen, and
- X is chosen from organic and inorganic anions.
32 more elements
A cationic azo compound of formula (I)
- W1—N═N—W2—W3 (I)
- wherein
- W1is 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)
- W3 is chosen from 5- and 6-membered heterocycles of the following formula (V)
- in which formulae (II) to (V):
- Z1 is chosen from an oxygen atom, a sulfur atom and a radical N(R12),
- Z2 is chosen from a nitrogen atom and a radical C(R11),
- R9 and R12, which may be identical or different, are chosen from C1-C8 alkyl radicals, optionally substituted by at least one radical chosen from hydroxyl, C1-C2 alkoxy, C2-C4 (poly)hydroxyalkoxy, amino, C1-C2 (di)alkylamino, carboxyl, and sulfonic radicals;
- and optionally substituted phenyl radicals,
- R10 and R11, which may be identical or different, are chosen from a hydrogen atom;
- C2-C4 alkyl radicals, optionally substituted by at least one radical chosen from hydroxyl, C1-C2 alkoxy, C2-C4 (poly)hydroxyalkoxy, amino, C1-C2 (di)alkylamino, carboxyl, and sulfonic radicals;
- optionally substituted phenyl radicals;
- carboxyl radicals;
- and sulfonylamino radicals,
- R5, R6, R7, and R8, which may be identical or different, are chosen from a hydrogen atom;
- a chlorine atom;
- a bromine atom;
- 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, of which at least one carbon atom of the carbonaceous chain can be replaced by an entity chosen from oxygen, nitrogen, and sulfur atoms and from an 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, and R8 are not chosen from a peroxide bond or from diazo and nitroso radicals,
- n is an integer equal to 0 or 1,
- R0, R1, R2, R3, and R4, which may be the same or different, are chosen from a hydrogen atom;
- hydroxyl radicals;
- amino radicals;
- acetoxy radicals;
- a group —N(R13)(R14), where R13 and R14, which may be identical or different, are chosen from a hydrogen atom and C1-C4 alkyl radicals substituted by at least one radical chosen from halogen atoms, and hydroxyl, C1C2 alkoxy, amino, and C1-C2 amino(di)alkyl radicals;
- sulfonylamino radicals;
- carboxyl radicals;
- carboxamido radicals;
- amido radicals;
- mono- and dialkylamido radicals;
- halogen radicals;
- C1-C6 alkyl radicals substituted by 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,
- with the proviso that at least one of the groups R0, R1, R2, R3, and R4 is not hydrogen, and
- X is chosen from organic and inorganic anions.
31 more elements
Dependencies are inferred from the claim text.