Cationic azo monomers or symmetric dimers, preparation thereof, compositions comprising same and process for dyeing keratin fibers

A compound of formula (I) or (II), and addition salts thereof:

• in which:
• R1, R2, and R3, which may be identical or different, are chosen from:
• linear or branched C1-C4 alkyl radicals that are unsubstituted or substituted with at least one entity chosen from:
• hydroxyl groups;
• linear or branched C1-C4 alkoxy groups;
• amino groups;
• and
• amino groups substituted with one or two radicals chosen from linear or branched C1-C4 alkyl radicals and linear or branched C1-C4 hydroxyalkyl radicals, which may be identical or different,
• wherein two of the radicals R1, R2, and R3 may optionally form a saturated or unsaturated, 5- or 6-membered heterocycle optionally comprising another hetero atom chosen from oxygen and nitrogen, said heterocycle being optionally substituted;
• R4, R′4, and R5, which may be identical or different, are chosen from:
• halogen atoms;
• hydroxyl groups;
• nitro groups
• cyano groups;
• linear or branched C1-C4 alkyl radicals, optionally comprising at least one entity chosen from hydroxyl groups, linear or branched C1-C4 alkoxy groups, amino groups and amino groups substituted with one or two radicals chosen from linear or branched C1-C4 alkyl radicals, which may be identical or different;
• linear or branched C1-C4 alkoxy radicals;
• amino radicals;
• and
• amino radicals substituted with one or two radicals, which may be identical or different, chosen from linear or branched C1-C4 alkyl radicals optionally substituted with one or two radicals chosen from:
• hydroxyl groups;
• amino groups;
• amino groups substituted with one or two radicals chosen from linear or branched C1-C4 alkyl radicals and linear or branched C1-C4 hydroxyalkyl radicals, which may be identical or different;
• substituted amino groups in which the radicals form a saturated or unsaturated 5- or 6-membered heterocycle optionally comprising another hetero atom chosen from oxygen and nitrogen;
• said heterocycle being optionally substituted;
• and
• —SO2NHR groups in which R is chosen from hydrogen, C1-C4 alkyl radicals, optionally substituted with at least one radical chosen from hydroxyl radicals, amino radicals, and amino radicals substituted with one or two radicals chosen from linear or branched C1-C4 alkyl radicals and linear or branched C1-C4 hydroxyalkyl radicals, which may be identical or different,
• wherein two radicals R5 carried by two adjacent carbon atoms may also form, with the carbon atom to which each is attached, an optionally substituted 6-membered aromatic ring;
• R6, R′6, and R′7, which may be identical or different, are chosen from:
• hydrogen;
• and
• linear or branched C1-C8 alkyl radicals that are unsubstituted or substituted with an entity chosen from hydroxyl groups, linear or branched C1-C4 alkoxy groups, amino groups, and amino groups substituted with one or two radicals chosen from linear or branched C1-C4 alkyl radicals and linear or branched C1-C4 hydroxyalkyl radicals, which may be identical or different;
• possibly interrupted with an entity chosen from hetero atoms chosen from oxygen and nitrogen and groups comprising a hetero atom;
• wherein the radicals R16 and R17 may optionally form a saturated or unsaturated 5- or 6-membered heterocycle optionally comprising another hetero atom chosen from oxygen and nitrogen;
• said heterocycle being optionally substituted;
• R7 is chosen from groups represented by formulae (a) and (b):
• R8 is chosen from groups represented by formula (c):
• R9 and R10, which may be identical or different, are chosen from:
• hydrogen,
• halogen atoms,
• nitro groups,
• cyano groups,
• linear or branched C1-C4 alkyl radicals optionally comprising at least one entity chosen from hydroxyl groups, linear or branched C1-C4 alkoxy groups, amino groups, and amino groups substituted with one or two radicals chosen from linear or branched C1-C4 alkyl radicals, which may be identical or different,
• hydroxyl groups,
• linear or branched C1-C4 alkoxy radicals,
• amino radicals,
• amino radicals substituted with one or more radicals, which may be identical or different, chosen from linear or branched C1-C6 alkyl radicals optionally substituted with at least one radical chosen from amino, hydroxyl radicals, ammonium radicals, (C1-C4)alkylammonium radicals, imidazolium radicals, pyrazolium radicals, pyridinium radicals, and amino radicals substituted with at least one radical chosen from linear or branched C1-C4 alkyl radicals and linear or branched C1-C4 alkoxy radicals, which may be identical or different, and
• substituted amino radicals in which the radicals form a saturated or unsaturated 5- or 6-membered heterocycle optionally comprising another hetero atom chosen from oxygen and nitrogen;
• said heterocycle being optionally substituted;
• with the proviso that R9 and R10, which may be identical or different, may not simultaneously represent chlorine or fluorine;
• X is chosen from nitrogen and the group —CR11, wherein R11 is chosen from:
• hydrogen,
• halogen atoms,
• nitro groups,
• cyano groups,
• linear or branched C1-C4 alkyl radicals optionally comprising at least one entity chosen from hydroxyl groups, linear or branched C1-C4 alkoxy groups, amino groups, and amino groups substituted with one or two radicals chosen from linear or branched C1-C4 alkyl radicals, which may be identical or different,
• linear or branched C1-C4 alkoxy radicals,
• amino radicals,
• amino radicals substituted with one or two radicals, which may be identical or different, chosen from linear or branched C1-C6 alkyl radicals optionally substituted with at least one radical chosen from amino radicals, hydroxyl radicals, and amino radicals substituted with one or two radicals chosen from linear or branched C1-C4 alkyl radicals and linear or branched C1-C4 hydroxyalkyl radicals, which may be identical or different, and
• substituted amino radicals in which the radicals form a saturated or unsaturated 5- or 6-membered heterocycle optionally comprising another hetero atom chosen from oxygen or nitrogen;
• said heterocycle being optionally substituted;
• L1, which may be cationic or noncationic, is chosen from linear, branched or cyclic, saturated or unsaturated C2-C20 hydrocarbon-based chains, optionally interrupted or terminated by a group comprising at least one hetero atom, optionally interrupted by at least one aromatic or nonaromatic, substituted or unsubstituted heterocycle or ring;
• L2, which may be cationic or noncationic, is chosen from:
• saturated or unsaturated, linear, branched, or cyclic C1-C20 hydrocarbon-based chains optionally interrupted or terminated by a group comprising at least one hetero atom, optionally interrupted or terminated by at least one optionally substituted, aromatic, or nonaromatic heterocycle or ring;
• aromatic or nonaromatic (hetero)cyclic radicals optionally attached to the nitrogen atoms by means of a group comprising at least one hetero atom;
• L3, which may be cationic or noncationic, is chosen from linear, branched, or cyclic, saturated or unsaturated C2-C20 hydrocarbon-based chains optionally interrupted or terminated by a group comprising at least one hetero atom, optionally interrupted by at least one optionally substituted aromatic or nonaromatic heterocycle or ring;
• n is a coefficient being less than or equal to 2;
• n′ is a coefficient being less than or equal to 3;
• m is a coefficient being less than or equal to 4;
• r is a coefficient being equal to 0 or 1;
• s is a coefficient being equal to 0 or 1;
• and
• An is at least one cosmetically acceptable counterion for ensuring the electroneutrality of the compounds of formulae (I) and (II) or the addition salts thereof.