Dyeing composition for keratinous fibers comprising a particular dicationic diazo dye
AssigneeL'oreal
InventorLaurent Vidal
Life of this patent
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Abstract
The invention concerns a dyeing composition for dyeing keratinous fibers, in particular human keratinous fibers and more particularly hair, comprising a dicationic diazo dye of formula W1—N═N—W2—N═N—W3 as well as the dyeing method using same and the novel compounds of formula (I).
Claims40
A composition for dyeing keratin fibers, comprising at least one dicationic diazo dye of formula (I) below:
- W1—N═N—W2—N═N—W3
- wherein
- W1 and W3, which may be identical or different, are chosen from heteroaromatic groups chosen from formulae (II) and (III) below:
- W2 is chosen from carbon-based, pyridine-based and pyridazine-based aromatic groups of formula (IV)
- wherein, in formulae (II), (III), and (IV):
- X1 is chosen from nitrogen and CR5,
- X2 is chosen from nitrogen and CR6,
- Z1 is chosen from oxygen, sulfur and NR8,
- Z2 is chosen from nitrogen and CR9,
- Z3 is chosen from nitrogen and CR12,
- Z4 is chosen from nitrogen and CR13,
- bond a of the 5-membered cationic ring of formula (II) may be linked to the azo group of formula (I),
- bond b of the 6-membered cationic ring of formula (III) may be linked to the azo group of formula (I),
- R3, R4, R5, R6, R7, R9, R10, R11, R12, and R13, which may be identical or different, are chosen from hydrogen and frorp linear and branched, saturated and unsaturated, C1-C16 hydrocarbon-based chains, wherein the chains can form at least one carbon-based ring comprising from 3 to 6 carbons, wherein at least one carbon atom of the carbon-based chain may be replaced with an entity chosen from oxygen, nitrogen and sulfur atoms and SO2 groups, and wherein the at least one carbon atom may be substituted with at least one halogen atom;
- wherein none of R3, R4, R5, R6, R7, R9, R10, R11, R12, and R13, comprises a peroxide bond, a diazo radical or a nitroso radical,
- R7 with R9, R10 with R11 and R12 with R13 may form carbon-based aromatic rings, and
- X is chosen from organic and mineral anions.
A process for dyeing keratin fibers comprising applying to said fibers a dye composition comprising at least one dicationic diazo dye of formula (I) below:
- W1—N═N—W2—N═N—W3
- wherein
- W1 and W3, which may be identical or different, are chosen from heteroaromatic groups chosen from formulae (II) and (III) below:
- W2 is chosen from carbon-based, pyridine-based and pyridazine-based aromatic groups of formula (IV)
- wherein, in formulae (II), (III), and (IV):
- X1 is chosen from nitrogen and CR5,
- X2 is chosen from nitrogen and CR6,
- Z1 is chosen from oxygen, sulfur and NR8,
- Z2 is chosen from nitrogen and CR9,
- Z3 is chosen from nitrogen and CR12,
- Z4 is chosen from nitrogen and CR13,
- bond a of the 5-membered cationic ring of formula (II) may be linked to the azo group of formula (I),
- bond b of the 6-membered cationic ring of formula (III) may be linked to the azo group of formula (I),
- R3, R4, R5, R6, R7, R9, R10, R11, R12, and R13, which may be identical or different, are chosen from hydrogen, linear and branched, saturated and unsaturated, C1-C16 hydrocarbon-based chains, wherein the chains can form at least one carbon-based ring comprising from 3 to 6 carbons, wherein at least one carbon of the carbon-based chain may be replaced with at least one entity chosen from oxygen, nitrogen and sulfur atoms and SO2 groups, and wherein the at least one carbon atom may be substituted with at least one halogen atom;
- wherein none of R3, R4, R5, R6, R7, R9, R10, R11, R12, and R13, comprises a peroxide bond, a diazo radical, or a nitroso radical,
- R7 with R9, R10 with R11 and R12 with R13 may form carbon-based aromatic rings, and
- X is chosen from organic and mineral anions.
A process for the oxidation dyeing of keratin fibers comprising
- applying to said fibers, in the presence of at least one oxidizing agent, a dye composition comprising at least one dicationic diazo dye of formula (I) below, at least one oxidation base, and optionally at least one coupler:
- W1—N═N—W2—N═N—W3
- wherein
- W1 and W3, which may be identical or different, are chosen from heteroaromatic groups chosen from formulae (II) and (III) below:
- W2 is chosen from carbon-based, pyridine-based arid pyridazine-based aromatic groups of formula (IV)
- wherein, in formulae (II), (III), and (IV):
- X1 is chosen from nitrogen and CR5,
- X2 is chosen from nitrogen and CR6,
- Z1 is chosen from oxygen, sulfur and NR8,
- Z2 is chosen from nitrogen and CR9,
- Z3 is chosen from nitrogen and CR12,
- Z4 is chosen from nitrogen and CR13,
- bond a of the 5-membered cationic ring of formula (II) may be linked to the azo group of formula (I),
- bond b of the 6-membered cationic ring of formula (III) may be linked to the azo group of formula (I),
- R3, R4, R5, R6, R7, R9, R10, R11, R12, and R13, which may be identical or different, are chosen from hydrogen, linear and branched, saturated and unsaturated, C1-C16 hydrocarbon-based chains, wherein the chains can form at least one carbon-based ring comprising from 3 to 6 carbons, wherein at least one carbon of the carbon-based chain may be replaced with an entity chosen from oxygen, nitrogen and sulfur atoms and SO2 groups, and wherein the at least one carbon atom may be substituted with at least one halogen atom;
- wherein none of R3, R4, R5, R6, R7, R9, R10, R11, R12, and R13, comprises a peroxide bond, a diazo radical or a nitroso radical,
- R7 with R9, R10 with R11 and R12 with R13 may form carbon-based aromatic rings, and
- X is chosen from organic and mineral anions.
A multi-compartment dyeing device, comprising at least two compartments, wherein the first compartment comprises at least one dicationic diazo dye of formula (I) below:
- W1—N═N—W2—N═N—W3
- wherein
- W1 and W3, which may be identical or different, are chosen from heteroaromatic groups chosen from formulae (II) and (III) below:
- W2 is chosen from carbon-based, pyridine-based and pyridazine-based aromatic groups of formula (IV)
- wherein, in formulae (II), (III), and (IV):
- X1 is chosen from nitrogen and CR5,
- X2 is chosen from nitrogen and CR6,
- Z1 is chosen from oxygen, sulfur and NR8,
- Z2 is chosen from nitrogen and CR9,
- Z3 is chosen from nitrogen and CR12,
- Z4 is chosen from nitrogen and CR13,
- bond a of the 5-membered cationic ring of formula (II) may be linked to the azo group of formula (I),
- bond b of the 6-membered cationic ring of formula (III) may be linked to the azo group of formula (I),
- R3, R4, R5, R6, R7, R9, R10, R11, R12, and R13, which may be identical or different, are chosen from hydrogen, linear and branched, saturated and unsaturated, C1-C16 hydrocarbon-based chains, wherein the chains can form at least one carbon-based ring comprising from 3 to 6 carbons, wherein at least one carbon of the carbon-based chain may be replaced with an entity chosen from oxygen, nitrogen and sulfur atoms and SO2 groups, and wherein the at least one carbon atom may be substituted with at least one halogen atom;
- and wherein none of R3, R4, R5, R6, R7, R9, R10, R11, R12, and R13 comprises a peroxide bond, a diazo radical, or a nitroso radical,
- R7 with R9, R10 with R11 and R12 with R13 may form carbon-based aromatic rings, and
- X is chosen from organic and mineral anions, and the second compartment comprises at least one oxidizing composition.
A dicationic diazo compound of formula (I):
- W1—N═N—W2—N═N—W3
- wherein
- W1 and W3, which may be identical or different, are chosen from heteroaromatic groups chosen from formulae (II) and (III) below:
- W2 is chosen from carbon-based, pyridine-based and pyridazine-based aromatic groups of formula (IV)
- wherein, in formulae (II), (III), and (IV):
- X1 is chosen from nitrogen and CR5,
- X2 is chosen from nitrogen and CR6,
- Z1 is chosen from oxygen, sulfur and NR8,
- Z2 is chosen from nitrogen and CR9,
- Z3 is chosen from nitrogen and CR12,
- Z4 is chosen from nitrogen and CR13,
- bond a of the 5-membered cationic ring of formula (II) may be linked to the azo group of formula (I),
- bond b of the 6-membered cationic ring of formula (III) may be linked to the azo group of formula (I),
- R3, R4, R6, R6, R7, R9, R10, R11, R12, and R13, which may be identical or different, are chosen from hydrogen, linear and branched, saturated and unsaturated, C1-C16 hydrocarbon-based chains, wherein the chains can form at least one carbon-based ring comprising from 3 to 6 carbons, wherein at least one carbon of the carbon-based chain may be replaced with an entity chosen from oxygen, nitrogen and sulfur atoms and SO2 groups, and wherein the at least one carbon atom may be substituted with at least one halogen atom;
- and wherein none of R3, R4, R5, R6, R7, R9, R10, R11, R12, and R13 comprises a peroxide bond, a diazo radical, or a nitroso radical,
- R7 with R9, R10 with R11 and R12 with R13 may form carbon-based aromatic rings, and
- X is chosen from organic and mineral anions.
Dependencies are inferred from the claim text.