Dicationic compounds for dyeing human keratin fibers, and compositions comprising them

A cosmetic composition for dyeing human keratin fibers comprising;

• a medium suitable for dyeing human keratin fibers,
• an effective amount of at least one direct dye present in said medium, chosen from those of formulae (I), (II) and (III):
• wherein:
• A and A1, which may be identical or different, are chosen from radicals of formula (a)
• Z is chosen from aliphatic and aromatic radicals,
• Z1 is an alkyl radical,
• R1 and R2, which may be identical or different, are chosen from hydrogen atoms;
• (C1-C4)alkyl radicals optionally substituted with at least one entity chosen from halogen atoms, hydroxyl, carboxyl and cyano radicals;
• (C1-C4)alkoxy radicals optionally substituted with at least one radical chosen from hydroxyl and (C1-C4)alkoxy radicals;
• and amino, alkylamino, dialkylamino, aminocarbonyl, phenyl, phenoxy and phenylaminocarbonyl radicals, wherein the phenyl radicals are optionally substituted with at least one radical chosen from (C1-C4)alkyl, (C1-C4)alkoxy and phenoxy radicals, or R1 and R2 can form, together with the two nitrogen atoms that bear them and the radical Z, a piperazine ring,
• X is a bridging radical chosen from —CO—;
• —CO—CH2—CH2—CO—;
• —CO—CO—;
• 1,4-dicarbonylphenyl;
• —CH2—CH2—;
• and triazines of formulae (b) and (c):
• wherein:
• Y and Y1, which may be identical or different, are chosen from halogen atoms and hydroxyl, amino, monoalkylamino, dialkylamino, 1 -piperidino, morpholino and 1-piperazino radicals, wherein the piperazino radicals are optionally substituted on the nitrogen atom not attached to the triazine ring with at least one (C1-C4)alkyl radical, said alkyl radicals being optionally substituted with at least one chosen from hydroxyl, amino, mono(C1-C4)alkylamino and di(C1-C4)alkylamino radicals,
• Z2 is an (C2-C8)alkylene radical or forms a piperazine ring with the two adjacent nitrogen atoms and the radicals R1 and R2,
• R3 and R4, which may be identical or different, are chosen from hydrogen atoms;
• (C1-C4)alkyl radicals optionally substituted with at least one entity chosen from halogen atoms, hydroxyl, carboxyl, and cyano radicals;
• (C1-C4)alkoxy radicals optionally substituted with at least one radical chosen from hydroxyl and (C1-C4)alkoxy radicals;
• and amino, alkylamino, dialkylamino, aminocarbonyl, phenyl, phenoxy and phenylaminocarbonyl radicals, wherein the phenyl radicals are optionally substituted with at least one radical chosen from (C1-C4)alkyl, (C1-C4)alkoxy and phenoxy radicals,
• R5 and R6, which may be identical or different, are chosen from hydrogen atoms;
• (C1-C4)alkyl and (C1-C4)alkoxy radicals optionally substituted with at least one radical chosen from hydroxyl, carboxyl, halogen and cyano radicals;
• (C1-C4)alkoxy radicals optionally substituted with a radical chosen from hydroxyl and (C1-C4)alkoxy radicals;
• and amino, alkylamino, dialkylamino, aminocarbonyl, phenyl, phenoxy and phenylaminocarbonyl radicals, wherein the phenyl radicals are potionally substituted with at least one radical chosen from (C1-C4)alkyl, (C1-C4)alkoxy and phenoxy radicals,
• An− is an anion;
• X′ and Y′, which may be identical or different, are chosen from hydrogen atoms, halogen atoms, and (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkylcarbonylamino, arylcarbonylamino, ureido and arylureido radicals,
• R′1 is chosen from hydrogen, optionally substituted alkyl and aryl radicals, and R′2 radicals;
• R′2 is a radical of formula (d):
• wherein:
• B is chosen from linear and branched alkylene radicals,
• R′6 is chosen from hydrogen atoms and optionally substituted alkyl radicals,
• R′7 and R′8, which may be identical or different, are chosen from optionally substituted alkyl radicals,
• R′6 and R′7, together with the nitrogen, form an optionally substituted 5-, 6- or 7-membered ring, which may comprise other hetero atoms, or alternatively R′6, R′7 and R′8 together form a pyridinium ring,
• R′3 is chosen from hydrogen atoms, halogen atoms, and (C1-C4)alkyl and (C1-C4)-alkoxy radicals,
• W is a radical of formula (e):
• wherein:
• K is a coupling radical,
• Z is a bridging radical chosen from the radicals of formulae:
• wherein
• R′9 is chosen from hydrogen atoms and optionally substituted (C2-C4)alkyl radicals, and
• B1 is chosen from linear and branched C2-C12 alkylene radicals optionally interrupted with at least one entity chosen from —NR′9— radicals, oxygen atoms and sulfur atoms;
• and wherein in formula (III), the number of cationic charges is two, and
• at least one surfactant chosen from anionic, amphoteric, nonionic, zwitterionic, and cationic surfactants.

A multi-compartment dyeing kit, comprising

• at least one first compartment comprises a composition comprising at least one direct dye chosen from formulae (I), (II) and (III):
• wherein:
• A and A1, which may be identical or different, are chosen from radicals of formula (a)
• Z is chosen from aliphatic and aromatic radicals,
• Z1 is an alkyl radical,
• R1 and R2, which may be identical or different, are chosen from hydrogen atoms, (C1-C4)alkyl radicals optionally substituted with at least one entity chosen from halogen atoms, hydroxyl, carboxyl and cyano radicals;
• (C1-C4)alkoxy radicals optionally substituted with at least one radical chosen from hydroxyl and (C1-C4)alkoxy radicals;
• and amino, alkylamino, dialkylamino, aminocarbonyl, phenyl, phenoxy and phenylaminocarbonyl radicals, wherein the phenyl radicals are optionally substituted with at least one radical chosen from (C1-C4)alkyl, (C1-C4)alkoxy and phenoxy radicals, or R1 and R2 can form, together with the two nitrogen atoms that bear them and the radical Z, a piperazine ring,
• X is a bridging radical chosen from —CO—;
• —CO—CH2—CH2—CO—;
• —CO—CO—;
• 1,4-dicarbonyiphenyl;
• —CH2—CH2—;
• and triazines of formulae (b) and (c):
• wherein:
• Y and Y1, which may be identical or different, are chosen from halogen atoms and hydroxyl, amino, monoalkylamino, dialkylamino, 1-piperidino, morpholino and 1-piperazino radicals, wherein the piperazino radicals are optionally substituted on the nitrogen atom not attached to the triazine ring with at least one (C1-C4)alkyl radical, said alkyl radicals being optionally substituted with at least one radical chosen from hydroxyl, amino, mono(C1-C4)alkylamino and di(C1-C4)alkylamino radicals,
• Z2 is an (C2-C8)alkylene radical or forms a piperazine ring with the two adjacent nitrogen atoms and the radicals R1 and R2,
• R3 and R4, which may be identical or different, are chosen from hydrogen atoms, (C1-C4)alkyl radicals optionally substituted with at least one entity chosen from halogen atoms, hydroxyl, carboxyl, and cyano radicals;
• (C1-C4)alkoxy radicals optionally substituted with at least one radical chosen from hydroxyl and (C1-C4)alkoxy radicals;
• and amino, alkylamino, dialkylamino, aminocarbonyl, phenyl, phenoxy and phenylaminocarbonyl radicals, wherein the phenyl radicals are optionally substituted with at least one radical chosen from (C1-C4)alkyl, (C1-C4)alkoxy and phenoxy radicals,
• R5 and R6, which may be identical or different, are chosen from hydrogen atoms, and (C1-C4)alkyl and (C1-C4)alkoxy radicals optionally substituted with at least one radical chosen from hydroxyl, carboxyl, halogen and cyano radicals;
• (C1-C4)alkoxy radicals optionally substituted with at least one radical chosen from hydroxyl and (C1-C4)alkoxy radicals;
• and amino, alkylamino, dialkylamino, aminocarbonyl, phenyl, phenoxy and phenylaminocarbonyl radicals, wherein the phenyl radicals are optionally substituted with at least one radical chosen from (C1-C4)alkyl, (C1-C4)alkoxy and phenoxy radicals,
• An− is an anion;
• X′ and Y′, which may be identical or different, are chosen from hydrogen atoms, halogen atoms, and (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkylcarbonylamino, arylcarbonylamino, ureido and arylureido radicals,
• R1 is chosen from hydrogen, optionally substituted alkyl and aryl radicals, and R′2 radicals;
• R′2 is a radical of formula (d):
• wherein:
• B is chosen from linear and branched alkylene radicals,
• R′6 is chosen from hydrogen atoms and optionally substituted alkyls,
• R′7 and R′8, which may be identical or different, are chosen from optionally substituted alkyl radicals,
• R′6 and R′7, together with the nitrogen, form an optionally substituted 5-, 6- or 7-membered ring, which may comprise other hetero atoms, or alternatively R′6, R′7 and R′8 together form a pyridinium ring,
• R′3 is chosen from hydrogen atoms, halogen atoms, and (C1-C4)alkyl and (C1-C4)-alkoxy radicals,
• W is a radical of formula (e):
• wherein:
• K is a coupling radical,
• Z is a bridging radical chosen from the radicals of formulae:
• and —CO—NR′9—B1—NR′9—CO—,
• wherein
• R′9 is chosen from hydrogen atoms and optionally substituted (C2-C4)alkyl radicals, and
• B1 is chosen from C2-C12 linear and branched alkylene radicals optionally interrupted with at least one entity chosen from —NR′9— radicals, oxygen atoms, and sulfur atoms;
• and wherein in formula (III), the number of cationic charges is two;
• and at least one second compartment comprising an oxidizing composition.