Dyeing composition for keratinous fibers comprising a dicationic diazo dye

A process for the oxidation dyeing of human keratin fibers, comprising applying to the fibers, at least one dye composition in the presence of at least one oxidizing agent, wherein the at least one dye composition comprises at least one oxidation base, optionally at least one coupler, and at least one dicationic diazo dye of formula (I):

• [W1—N═N—W2—W3—(W4—W5)p-]2-L Formula (I)
• wherein:
• p=0 or 1,
• W1 is chosen from heteroaromatic radicals of formulae (II) and (III):
• W2 is chosen from carbon-based, pyridine-based and pyridazine-based aromatic groups of formula (IV):
• W3 and W5, which may be identical or different, are chosen from —NR14— radicals, and oxygen and nitrogen atoms,
• W4 is chosen from saturated and unsaturated, linear and branched C1-C16 hydrocarbon-based chains, which can form at least one 3- to 6-membered carbon-based ring, wherein at least one carbon atom of the carbon-based chain may optionally be replaced with an entity chosen from oxygen, nitrogen and sulfur atoms, and from SO2 groups, and further wherein the carbon atoms may optionally be substituted, independently of each other, with at least one halogen atom, provided that W4 does not comprise a peroxide bond or diazo or nitroso radicals;
• piperazine rings;
• and groups of formula (V):
• wherein in formulae (II), (III), (IV) and (V):
• X1 is chosen from nitrogen atoms and CR5 radicals,
• X2 is chosen from nitrogen atoms and CR6 radicals,
• X3 is chosen from nitrogen atoms and CR17 radicals,
• X4 is chosen from nitrogen atoms and CR18 radicals,
• Z1 is chosen from oxygen and sulfur atoms, and NR8 radicals,
• Z2 is chosen from nitrogen atoms and CR9 atoms, with the proviso that when Z1 is chosen from NR8 radicals, then Z2 is not chosen from CR9 radicals, such that formula (II) is not an imidazolium ring,
• Z3 is chosen from nitrogen atoms and CR12 radicals,
• Z4 is chosen from nitrogen atoms and CR13 radicals,
• the bond a of the 5-membered cationic ring of formula (II) is linked to the azo group of formula (I),
• the bond b of the 6-membered cationic ring of formula (III) is linked to the azo group of formula (I),
• wherein when p=0, then L is chosen from linear and branched C1-C16 hydrocarbon-based chains, which can form at least one 3- to 6-membered carbon-based ring, wherein at least one carbon atom of the carbon-based chain is optionally replaced with an entity chosen from oxygen, nitrogen and sulfur atoms, and from SO2 groups, and further wherein the carbon atoms of the chain are optionally substituted, independently of each other, with at least one halogen atom;
• with the proviso that L does not comprise a peroxide bond or diazo or nitroso radicals,
• wherein when p=1, then L is chosen from saturated and unsaturated, linear and branched C1-C16 hydrocarbon-based chains, which can form at least one 3- to 6-membered carbon-based ring, wherein at least one carbon atom of the carbon-based chain is optionally replaced with an entity chosen from oxygen, nitrogen and sulfur atoms, and SO2 groups;
• with the proviso that L does not comprise a peroxide bond or diazo or nitroso radicals,
• R3, R4, R5, R6, R7, R9, R10, R11, R12, R13, R14, R15, R16, R17 and R18, which may be identical or different, are chosen from hydrogen atoms, saturated and unsaturated, linear and branched C1-C16 hydrocarbon-based chains, which can form at least one 3- to 6-membered carbon-based ring, wherein at least one carbon atom of the carbon-based chain is optionally replaced with an entity chosen from oxygen, nitrogen and sulfur atoms, and from SO2 groups, and the carbon atoms of the chain are optionally substituted, independently of each other, with at least one halogen atom;
• and with the proviso that R3, R4, R5, R6, R7, R9, R10, R11, R12, R13, R14, R15, R16, R17 and R18 do not comprise a peroxide bond or diazo or nitroso radicals,
• R3 with R4, R7 with R9, R10 with R11, R12 with R13 and R15 with R16 can optionally form a carbon-based aromatic ring,
• R1, R2 and R8 are chosen from linear and branched C1-C8 alkyl radicals optionally substituted with 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, and
• X is chosen from organic and mineral anions.

A multi-compartment kit, wherein at least one first compartment comprises a composition comprising at least one dicationic diazo dye of formula (I):

• [W1—N═N—W2—W3—(W4—W5)p-]2-L Formula (I)
• wherein:
• p=0 or 1,
• W1 is chosen from heteroaromatic radicals of formulae (II) and (III):
• W2 is chosen from carbon-based, pyridine-based and pyridazine-based aromatic groups of formula (IV):
• W3 and W5, which may be identical or different, are chosen from —NR14— radicals, and oxygen and nitrogen atoms,
• W4 is chosen from saturated and unsaturated, linear and branched C1-C16 hydrocarbon-based chains, which can form at least one 3- to 6-membered carbon-based ring, wherein at least one carbon atom of the carbon-based chain may optionally be replaced with an entity chosen from oxygen, nitrogen and sulfur atoms and from SO2 groups, and further wherein the carbon atoms may optionally be substituted, independently of each other, with at least one halogen atom, provided that W4 does not comprise a peroxide bond or diazo or nitroso radicals;
• piperazine rings;
• and groups of formula (V):
• wherein in formulae (II), (III), (IV) and (V):
• X1 is chosen from nitrogen atoms and CR5 radicals,
• X2 is chosen from nitrogen atoms and CR6 radicals,
• X3 is chosen from nitrogen atoms and CR7 radicals,
• X4 is chosen from nitrogen atoms and CR18 radicals,
• Z1 is chosen from oxygen and sulfur atoms, and NR8 radicals,
• Z2 is chosen from nitrogen atoms and CR9 atoms, with the proviso that when Z1 is chosen from NR8 radicals, then Z2 is not chosen from CR9 radicals, such that formula (II) is not an imidazolium ring,
• Z3 is chosen from nitrogen atoms and CR12 radicals,
• Z4 is chosen from nitrogen atoms and CR13 radicals,
• the bond a of the 5-membered cationic ring of formula (II) is linked to the azo group of formula (I),
• the bond b of the 6-membered cationic ring of formula (III) is linked to the azo group of formula (I),
• wherein when p=0, then L is chosen from linear and branched C1-C16 hydrocarbon-based chains, which can form at least one 3- to 6-membered carbon-based ring, wherein at least one carbon atom of the carbon-based chain is optionally replaced with an entity chosen from oxygen, nitrogen and sulfur atoms, and from SO2 groups, and further wherein the carbon atoms of the chain are optionally substituted, independently of each other, with at least one halogen atom;
• with the proviso that L does not comprise a peroxide bond or diazo or nitroso radicals,
• wherein when p=1, then L is chosen from saturated and unsaturated, linear and branched C1 -C16 hydrocarbon-based chains, which can form at least one 3- to 6-membered carbon-based ring, wherein at least one carbon atom of the carbon-based chain is optionally replaced with an entity chosen from oxygen, nitrogen and sulfur atoms, and from SO2 groups;
• with the proviso that L does not comprise a peroxide bond or diazo or nitroso radicals,
• R3, R4, R5, R6, R7, R9, R10, R11, R12, R13, R14, R15, R16, R17 and R18, which may be identical or different, are chosen from hydrogen atoms, saturated and unsaturated, linear and branched C1-C16 hydrocarbon-based chains, which can form at least one 3- to 6-membered carbon-based ring, wherein at least one carbon atom of the carbon-based chain is optionally replaced with an entity chosen from oxygen,
• nitrogen and sulfur atoms, and from SO2 groups, and the carbon atoms of the chain are optionally substituted, independently of each other, with at least one halogen atom;
• and with the proviso that R3, R4, R5, R6, R7, R9, R10, R11, R12, R13, R14, R15, R16, R17 and R18 do not comprise a peroxide bond or diazo or nitroso radicals,
• R3 with R4, R7 with R9, R10 with R11, R12 with R13 and R15 with R16 can optionally form a carbon-based aromatic ring,
• R1, R2 and R8 are chosen from linear and branched C1-C8 alkyl radicals optionally substituted with 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, and
• X is chosen from organic and mineral anions;
• and
• at least one second compartment comprises an oxidizing composition.