Dyeing composition comprising a dye chosen from styryl and imine dyes and methods for dyeing keratin fibers
AssigneeL'oreal
InventorGregory Plos
Life of this patent
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Abstract
Disclosed herein is a method for dyeing keratin fibers, for example, human keratin fibers such as the hair, comprising applying to the keratin fibers a dye composition comprising at least one compound chosen from styryl and imine compounds comprising a heterocycle that can undergo opening and/or dyes corresponding to these compounds whose heterocycles are open. The compositions and methods of the present disclosure may produce a coloration of keratin fibers that is chromatic and fast with respect to external factors such as shampooing, does not stain, and/or allows simultaneous dyeing and bleaching of keratin fibers.
Claims35
A method for dyeing keratin fibers comprising applying to the keratin fibers a dye composition comprising, in a suitable dyeing medium, at least one compound chosen from compounds of formulas (I) and (II), and addition salts thereof:
- wherein:
- A is chosen from substituted or unsubstituted, 5- to 16-membered, fused or non-fused, aromatic or heteroaromatic nuclei;
- X is chosen from oxygen, sulfur, and CR1R2 groups;
- R1 and R2, which may be identical or different, are chosen from hydrogen, C1-C6 alkyl radicals, C1-C6 hydroxyalkyl radicals, C1-C6 alkoxyalkyl radicals, and alkylene chains optionally comprising at least one atom chosen from oxygen and sulfur atoms;
- R1 and R2 may together form an aromatic or non-aromatic 5- or 6-membered ring optionally comprising at least one heteroatom chosen from nitrogen, oxygen, and sulfur;
- R3 is chosen from hydrogen, halogen atoms, C1-C6 alkyl radicals, cyano radicals, aromatic groups, phenoxy groups, and nitro radicals;
- W is chosen from CR4 groups and nitrogen;
- R4 is chosen from hydrogen, halogen atoms, C1-C6 alkyl radicals, cyano radicals, aromatic groups, phenoxy radicals, and nitro radicals.
- Y is chosen from oxygen, sulfur, and NR5 groups;
- R5 is chosen from hydrogen and C1-C6 alkyl radicals;
- Z is chosen from —CpH2p— groups, wherein p is an integer ranging from 2 to 4, which may be optionally substituted with at least one substituent chosen from halo, hydroxyl, alkyl, haloalkyl, alkoxy, amino, monoalkylamino, dialkylamino, monohydroxyalkylamino, dihydroxyalkylamino, and carboxyl radicals;
- —CqH2qCO— groups, wherein q is an integer ranging from 1 to 3, which may be optionally substituted with at least one substituent chosen from halo, hydroxyl, alkyl, haloalkyl, alkoxy, amino, monoalkylamino, dialkylamino, monohydroxyalkylamino, dihydroxyalkylamino, and carboxyl radicals;
- n is an integer from 1 to 4;
- and
- B is chosen from substituted or unsubstituted, 5- to 16-membered, fused or non-fused aromatic or heteroaromatic nuclei.
A process for treating keratin fibers, comprising applying a dye composition to the keratin fibers for a leave-on time sufficient to develop a desired coloration, optionally followed by rinsing, wherein the dye composition comprises, in a suitable dyeing medium, at least one compound chosen from compounds of formulas (I) and (II), and addition salts thereof:
- wherein:
- A is chosen from substituted or unsubstituted, 5- to 16-membered, fused or non-fused aromatic or heteroaromatic nuclei;
- X is chosen from oxygen, sulfur, and CR1R2 groups;
- R1 and R2, which may be identical or different, are chosen from hydrogen, C1-C6 alkyl radicals, C1-C6 hydroxyalkyl radicals, C1-C6 alkoxyalkyl radicals, and alkylene chains optionally comprising at least one atom chosen from oxygen and sulfur atoms;
- and R1 and R2 may together form an aromatic or non-aromatic 5- or 6-membered ring optionally comprising at least one heteroatom chosen from nitrogen, oxygen, and sulfur;
- R3 is chosen from hydrogen, halogen atoms, C1-C6 alkyl radicals, cyano radicals, aromatic groups, phenoxy groups, and nitro radicals;
- W is chosen from CR4 groups and nitrogen;
- R4 is chosen from hydrogen, halogen atoms, C1-C6 alkyl radicals, cyano radicals, aromatic groups, phenoxy radicals, and nitro radicals.
- Y is chosen from oxygen, sulfur, and NR5 groups;
- R5 is chosen from hydrogen and C1-C6 alkyl radicals;
- Z is chosen from —CpH2p— groups, wherein p is an integer ranging from 2 to 4, which may be optionally substituted with at least one substituent chosen from halo, hydroxyl, alkyl, haloalkyl, alkoxy, amino, monoalkylamino, dialkylamino, monohydroxyalkylamino, dihydroxyalkylamino, and carboxyl radicals;
- —CqH2qCO— groups, wherein q is an integer ranging from 1 to 3, which may be optionally substituted with at least one substituent chosen from halo, hydroxyl, alkyl, haloalkyl, alkoxy, amino, monoalkylamino, dialkylamino, monohydroxyalkylamino, dihydroxyalkylamino, and carboxyl radicals;
- n is an integer from 1 to 4;
- and
- B is chosen from substituted or unsubstituted, 5- to 16-membered, fused or non-fused aromatic or heteroaromatic nuclei.
A multi-compartment device comprising at least one first compartment containing at least one dye composition, and at least one second compartment comprising at least one agent chosen from acidifying agents, basifying agents,and/or solvents, wherein the at least one dye composition comprises, in a suitable dyeing medium, at least one compound chosen from compounds of formulas (I) and (II), and addition salts thereof:
- wherein:
- A is chosen from substituted or unsubstituted, 5- to 16-membered, fused or non-fused aromatic or heteroaromatic nuclei;
- X is chosen from oxygen, sulfur, and CR1R2 groups;
- R1 and R2, which may be identical or different, are chosen from hydrogen, C1-C6 alkyl radicals, C1-C6 hydroxyalkyl radicals, C1-C6 alkoxyalkyl radicals, and alkylene chains optionally comprising at least one atom chosen from oxygen and sulfur atoms;
- and R1 and R2 may together form an aromatic or non-aromatic 5- or 6-membered ring optionally comprising at least one heteroatom chosen from nitrogen, oxygen, and sulfur;
- R3 is chosen from hydrogen, halogen atoms, C1-C6 alkyl radicals, cyano radicals, aromatic groups, phenoxy groups, and nitro radicals;
- W is chosen from CR4 groups and nitrogen;
- R4 is chosen from hydrogen, halogen atoms, C1-C6 alkyl radicals, cyano radicals, aromatic groups, phenoxy radicals, and nitro radicals.
- Y is chosen from oxygen, sulfur, and NR5 groups;
- R5 is chosen from hydrogen and C1-C6 alkyl radicals;
- Z is chosen from —CpH2p— groups, wherein p is an integer ranging from 2 to 4, which may be optionally substituted with at least one substituent chosen from halo, hydroxyl, alkyl, haloalkyl, alkoxy, amino, monoalkylamino, dialkylamino, monohydroxyalkylamino, dihydroxyalkylamino, and carboxyl radicals;
- —CqH2qCO— groups, wherein q is an integer ranging from 1 to 3, which may be optionally substituted with at least one substituent chosen from halo, hydroxyl, alkyl, haloalkyl, alkoxy, amino, monoalkylamino, dialkylamino, monohydroxyalkylamino, dihydroxyalkylamino, and carboxyl radicals;
- n is an integer from 1 to 4;
- and
- B is chosen from substituted or unsubstituted, 5- to 16-membered, fused or non-fused aromatic or heteroaromatic nuclei.
A compound chosen from compounds of formulas (I) and (II), and addition salts thereof, wherein the compound comprises at least one cationic quaternary ammonium group:
- wherein:
- A is chosen from substituted or unsubstituted, 5- to 16-membered, fused or non-fused aromatic or heteroaromatic nuclei;
- X is chosen from oxygen, sulfur, and CR1R2 groups;
- R1 and R2, which may be identical or different, are chosen from hydrogen, C1-C6 alkyl radicals, C1-C6 hydroxyalkyl radicals, C1-C6 alkoxyalkyl radicals, and alkylene chains optionally comprising at least one atom chosen from oxygen and sulfur atoms;
- and R1 and R2 may together form an aromatic or non-aromatic 5- or 6-membered ring optionally comprising at least one heteroatom chosen from nitrogen, oxygen, and sulfur;
- R3 is chosen from hydrogen, halogen atoms, C1-C6 alkyl radicals, cyano radicals, aromatic groups, phenoxy groups, and nitro radicals;
- W is chosen from CR4 groups and nitrogen;
- R4 is chosen from hydrogen, halogen atoms, C1-C6 alkyl radicals, cyano radicals, aromatic groups, phenoxy radicals, and nitro radicals.
- Y is chosen from oxygen, sulfur, and NR5 groups;
- R5 is chosen from hydrogen and C1-C6 alkyl radicals;
- Z is chosen from —CpH2p— groups, wherein p is an integer ranging from 2 to 4, which may be optionally substituted with at least one substituent chosen from halo, hydroxyl, alkyl, haloalkyl, alkoxy, amino, monoalkylamino, dialkylamino, monohydroxyalkylamino, dihydroxyalkylamino, and carboxyl radicals;
- —CqH2qCO— groups, wherein q is an integer ranging from 1 to 3, which may be optionally substituted with at least one substituent chosen from halo, hydroxyl, alkyl, haloalkyl, alkoxy, amino, monoalkylamino, dialkylamino, monohydroxyalkylamino, dihydroxyalkylamino, and carboxyl radicals;
- n is an integer from 1 to 4;
- and
- B is chosen from substituted or unsubstituted, 5- to 16-membered, fused or non-fused aromatic or heteroaromatic nuclei.
A dye composition comprising, in a suitable dyeing medium, at least one compound chosen from compounds of formulas (I) and (II), and addition salts thereof, wherein the at least one compound comprises at least one cationic quaternary ammonium group:
- wherein:
- A is chosen from substituted or unsubstituted, 5- to 16-membered, fused or non-fused aromatic or heteroaromatic nuclei;
- X is chosen from oxygen, sulfur, and CR1R2 groups;
- R1 and R2, which may be identical or different, are chosen from hydrogen, C1-C6 alkyl radicals, C1-C6 hydroxyalkyl radicals, C1-C6 alkoxyalkyl radicals, and alkylene chains optionally comprising at least one atom chosen from oxygen and sulfur atoms;
- and R1 and R2 may together form an aromatic or non-aromatic 5- or 6-membered ring optionally comprising at least one heteroatom chosen from nitrogen, oxygen, and sulfur;
- R3 is chosen from hydrogen, halogen atoms, C1-C6 alkyl radicals, cyano radicals, aromatic groups, phenoxy groups, and nitro radicals;
- W is chosen from CR4 groups and nitrogen;
- R4 is chosen from hydrogen, halogen atoms, C1-C6 alkyl radicals, cyano radicals, aromatic groups, phenoxy radicals, and nitro radicals;
- Y is chosen from oxygen, sulfur, and NR5 groups;
- R5 is chosen from hydrogen and C1-C6 alkyl radicals;
- Z is chosen from —CpH2p— groups, wherein p is an integer ranging from 2 to 4, which may be optionally substituted with at least one substituent chosen from halo, hydroxyl, alkyl, haloalkyl, alkoxy, amino, monoalkylamino, dialkylamino, monohydroxyalkylamino, dihydroxyalkylamino, and carboxyl radicals;
- —CqH2qCO— groups, wherein q is an integer ranging from 1 to 3, which may be optionally substituted with at least one substituent chosen from halo, hydroxyl, alkyl, haloalkyl, alkoxy, amino, monoalkylamino, dialkylamino, monohydroxyalkylamino, dihydroxyalkylamino, and carboxyl radicals;
- n is an integer from 1 to 4;
- and
- B is chosen from substituted or unsubstituted, 5- to 16-membered, fused or non-fused aromatic or heteroaromatic nuclei.
Dependencies are inferred from the claim text.