Dyeing composition for keratinous fibres comprising a particular dicationic diazo dye

A process for dyeing keratin fibers, comprising applying to the keratin fibers a composition comprising, at least one dicationic diazo dye of formula (I):

• wherein
• n is an integer chosen from 0 and 1,
• W1 and W5, which are identical or different, are chosen from heteroaromatic radicals of formulae (II) and (III):
• wherein,
• W3 is chosen from an oxygen atom, NR14, —NR15—W6—NR16—, —NR16—W6—O—, —O—W6—O—,
• W6 and carbonyl radicals,
• W2 and W4, which are identical or different, are chosen from carbon-based, pyridine-based and pyridazine-based aromatic groups of formula (IV):
• W6 is chosen from 5-membered and 6-membered aromatic and heteroaromatic groups of formula (V):
• wherein
• m is an integer chosen from 0 and 1,
• X1 is chosen from a nitrogen atom and CR5 radicals,
• X2 is chosen from a nitrogen atom and CR6 radicals,
• X3 is chosen from a nitrogen atom, a carbon atom, and CR18 radicals,
• X4 is chosen from a nitrogen atom, a carbon atom, and CR19 radicals,
• X5 is chosen from a nitrogen atom, a carbon atom, and CR20 radicals,
• X6 is chosen from a nitrogen atom, a carbon atom, and CR21 radicals,
• Z1 is chosen from an oxygen atom, a sulfur atom, and NR8 radicals,
• Z2 is chosen from a nitrogen atom and CR9 radicals,
• Z3 is chosen from a nitrogen atom and CR12 radicals,
• Z4 is chosen from a nitrogen atom 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),
• with the proviso that when X3 to X6 are chosen from carbon atoms, then they are linked to W2 or W4,
• and with the proviso that formula (V) does not comprise more than three nitrogen atoms,
• and further with the proviso that when formula (V) comprises three nitrogen atoms, they are noncontiguous,
• R1, R2 and R8, which are identical or different, 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;
• a phenyl radical 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 a halogen atom,
• R3, R4, R5, R6, R7, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20 and R21, which are identical or different, are chosen from a hydrogen atom, linear and branched, saturated and unsaturated C1–C16 hydrocarbon-based chains, wherein at least one carbon atom of the carbon-based chain may be replaced with at least one atom chosen from oxygen, nitrogen and sulfur atoms and with an SO2 group, and wherein the carbon atoms of which may be 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, R18, R19, R20 and R21 do not comprise a peroxide bond or diazo or nitroso radicals,
• R7 with R9, R10 with R11 and R12 with R13 may form a carbon-based aromatic ring, and
• X is chosen from organic and mineral anions.

A process for the oxidation dyeing of keratin fibers, comprising applying to the keratin fibers at least one dye composition comprising at least one dicationic diazo dye of formula (I):

• wherein
• n is an integer chosen from 0 and 1,
• W1 and W5, which are identical or different, are chosen from heteroaromatic radicals of formulae (II) and (III):
• wherein,
• W3 is chosen from an oxygen atom, NR14, —NR15—W6—NR16—, —NR16—W6—O—, —O—W6—O—,
• W6 and carbonyl radicals,
• W2 and W4, which are identical or different, are chosen from carbon based, pyridine based and pyridazine-based aromatic groups of formula (IV):
• W6 is chosen from 5-membered and 6-membered aromatic and heteroaromatic groups of formula (V):
• wherein
• m is an integer chosen from 0 and 1,
• X1 is chosen from a nitrogen atom and CR5 radicals,
• X2 is chosen from a nitrogen atom and CR6 radicals,
• X3 is chosen from a nitrogen atom, a carbon atom, and CR18 radicals,
• X4 is chosen from a nitrogen atom, a carbon atom, and C19 radicals,
• X5 is chosen from a nitrogen atom, a carbon atom, and CR20 radicals,
• X6 is chosen from a nitrogen atom, a carbon atom, and CR21 radicals,
• Z1 is chosen from an oxygen atom, a sulfur atom, and NR8 radicals,
• Z2 is chosen from a nitrogen atom and CR9 radicals,
• Z3 is chosen from a nitrogen atom and CR12 radicals,
• Z4 is chosen from a nitrogen atom 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),
• with the proviso that when X3 to X6 are chosen from carbon atoms, then they are linked to W2 or W4,
• and with the proviso that formula (V) does not comprise more than three nitrogen atoms,
• and further with the proviso that when formula (V) comprises three nitrogen atoms, they are noncontiguous,
• R1, R2 and R8, which are identical or different, 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;
• a phenyl radical 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 a halogen atom,
• R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20 and R21, which are identical or different, are chosen from a hydrogen atom, linear and branched, saturated and unsaturated C1–C16 hydrocarbon-based chains, wherein at least one carbon atom of the carbon-based chain may be replaced with at least one atom chosen from oxygen, nitrogen and sulfur atoms and with an SO2 group, and wherein the carbon atoms of which may be 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, R18, R19, R20 and R21 do not comprise a peroxide bond or diazo or nitroso radicals,
• R7 with R9, R10 with R11 and R12 with R13 may form a carbon-based aromatic ring, and
• X is chosen from organic and mineral anions,
• and also comprising at least one oxidation base and optionally at least one coupler, wherein the application to the fibers is in the presence of an oxidizing agent.

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

• wherein
• n is an integer chosen from 0 and 1,
• W1 and W5, which are identical or different, are chosen from heteroaromatic radicals of formulae (II) and (III):
• wherein,
• W3 is chosen from an oxygen atom, NR14, —NR15—W6—NR16—, —NR16—W6—O—, —O—W6—O—,
• W6 and carbonyl radicals,
• W2 and W4, which are identical or different, are chosen from carbon-based, pyridine-based and pyridazine-based aromatic groups of formula (IV):
• W6 is chosen from 5-membered and 6-membered aromatic and heteroaromatic groups of formula (V):
• wherein
• m is an integer chosen from 0 and 1,
• X1 is chosen from a nitrogen atom and CR5 radicals,
• X2 is chosen from a nitrogen atom and CR6 radicals,
• X3 is chosen from a nitrogen atom, a carbon atom, and CR18 radicals,
• X4 is chosen from a nitrogen atom, a carbon atom, and CR19 radicals,
• X5 is chosen from a nitrogen atom, a carbon atom, and CR20 radicals,
• Z1 is chosen from an oxygen atom, a sulfur atom, and NR8 radicals,
• Z2 is chosen from a nitrogen atom and CR9 radicals,
• Z3 is chosen from a nitrogen atom and CR12 radicals,
• Z4 is chosen from a nitrogen atom 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),
• with the proviso that when X3 to X6 are chosen from carbon atoms, then they are linked to W2 or W4,
• and with the proviso that formula (V) does not comprise more than three nitrogen atoms,
• and further with the proviso that when formula (V) comprises three nitrogen atoms, they are noncontiguous,
• R1, R2 and R8, which are identical or different, 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;
• a phenyl radical 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 a halogen atom,
• R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20 and R21, which are identical or different, are chosen from a hydrogen atom, linear and branched, saturated and unsaturated C1–C16 hydrocarbon-based chains, wherein at least one carbon atom of the carbon-based chain may be replaced with at least one atom chosen from oxygen, nitrogen and sulfur atoms and with an SO2 group, and wherein the carbon atoms of which may be 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, R18, R19, R20 and R21 do not comprise a peroxide bond or diazo or nitroso radicals,
• R7 with R9, R10 with R11 and R12 with R13 may form a carbon-based aromatic ring, and
• X is chosen from organic and mineral anions, and at least one second compartment comprises an oxidizing composition.

A dicationic diazo compound of formula (I):

• wherein
• n is an integer chosen from 0 and 1,
• W1 and W5, which are identical or different, are chosen from heteroaromatic radicals of formulae (II) and (III):
• wherein,
• W3 is chosen from an oxygen atom, NR14, —NR15—W6—NR16—, —NR6—W6—O—, —O—W6—O—,
• W6 and carbonyl radicals,
• W2 and W4, which are identical or different, are chosen from carbon-based, pyridine-based and pyridazine-based aromatic groups of formula (IV):
• W6 is chosen from 5-membered and 6-membered aromatic and heteroaromatic groups of formula (V):
• wherein
• m is an integer chosen from 0 and 1,
• X1 is chosen from a nitrogen atom and CR5 radicals,
• X2 is chosen from a nitrogen atom and CR6 radicals,
• X3 is chosen from a nitrogen atom, a carbon atom, and CR18 radicals,
• X4 is chosen from a nitrogen atom, a carbon atom, and CR19 radicals,
• X5 is chosen from a nitrogen atom, a carbon atom, and CR20 radicals,
• X6 is chosen from a nitrogen atom, a carbon atom, and CR21, radicals,
• Z1 is chosen from an oxygen atom, a sulfur atom, and NR8 radicals,
• Z2 is chosen from a nitrogen atom and CR9 radicals,
• Z3 is chosen from a nitrogen atom and CR12 radicals,
• Z4 is chosen from a nitrogen atom 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),
• with the proviso that when X3 to X6 are chosen from carbon atoms, then they are linked to W2 or W4,
• and with the proviso that formula (V) does not comprise more than three nitrogen atoms,
• and further with the proviso that when formula (V) comprises three nitrogen atoms, they are noncontiguous,
• R1, R2 and R8, which are identical or different, are chosen from linear and branched C1–C6 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;
• a phenyl radical 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 a halogen atom,
• R3, R4, R5, R6, R7, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20 and R21, which are identical or different, are chosen from a hydrogen atom, linear and branched, saturated and unsaturated C1–C16 hydrocarbon-based chains, wherein at least one carbon atom of the carbon-based chain may be replaced with at least one atom chosen from oxygen, nitrogen and sulfur atoms and with an SO2 group, and wherein the carbon atoms of which may be 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, R17, R19, R20 and R21 do not comprise a peroxide bond or diazo or nitroso radicals,
• R7 with R9, R10 with R11, and R12 with R13 may form a carbon-based aromatic ring, and
• X is chosen from organic and mineral anions.