Patent FR-2920780-A1 (FR)
Title: New di/tetraazo cationic disulfide or thiol compounds useful as dye for coloring keratin fibers, preferably human keratin fibers such as hair
Inventor: GREAVES ANDREW
IPC: A61K8/46
Filed: 2007-09-11
Abstract: Di/tetraazo cationic disulfide or thiol compounds (A) and their organic acid addition salts, mineral salts, solvates, tautomers or optical and geometrical isomers as dye are new. Di/tetraazo cationic disulfide or thiol compounds (A) of formula ([W 1-N=N-W 2-N=N-W 3-X-L-S] x-[Y 1] y) (I) or ([W 5-N=N-W 2-N=N-W 4-L-S] x-[Y 1] y) (II) and their organic acid addition salts, mineral salts, solvates, tautomers, or optical and geometrical isomers as dye are new. W 1pyridinium radical of formula (IIa) or imidazole group of formula (IIb); W 2substituted phenyl group of formula (III); W 3substituted phenyl group of formula (IV); W 4heteroaryl radical of formula (Va) or (Vb); W 5substituted phenyl group of formula (VI); m, n, o : 0-4; p : 0-5; e : 0-2; L : covalent bond, 1-20C bivalent hydrocarbon chain (optionally substituted and optionally interrupted by one or more divalent groups or their combinations, two divalent groups or their combinations are separated by divalent hydrocarbon chain, preferably 1-6C alkylene, where the divalent groups are -N(R)-, N +>(R)R0)-, An ->, -O-, -S-, -C(O)-, cationic heterocycle or cationic heteroaryl (Het +>An ->), non cationic heterocycle comprising 5-10 chains or (hetero)aryl (optionally substituted), where L does not comprises diazo, hydrazino, aminooxy, nitro, nitroso or peroxide; R : 1-4C alkyl, 2-6C (poly)hydroxyalkyl, alkoxy(1-6C)alkyl, aryl, aryl(1-6C)alkyl, (1-4C)alkylcarbonylamino(1-6C)alkyl or amino(1-4C)alkyl (in which the amino is substituted by one or more 1-4C alkyl, alkyl(1-6C)carbonyl or (1-4C)alkylcarbonylamino); R0 : H or R; Het +>cationic heterocycle containing 5-10 chains (optionally saturated) or cationic heteroaryl containing 5-10 chains; X : -NR1a- or -NR1a-CO-; R1a : H or 1-6C alkyl; R 11-6C alkyl, aryl-1-6C-alkyl, (hetero)aryl or heteroaryl(1-6C)alkyl (all optionally substituted), cycloalkyl(1-6C)alkyl or heterocycloalkyl(1-6C)alkyl; either R 2-R 51-6C alkyl, 1-4C (poly)hydroxyalkyl, OH, 1-4C alkoxy, 2-4C (poly)hydroxyalkyl, alkoxycarbonyl (R 11O-CO-), amino (optionally substituted by one or more 1-4C alkyl and containing OH) (where two radical alkyl radical together with N form 5 or 6 membered heterocycle containing O or N), alkylcarbonylamino (R 12CO-NR 12-), carbamoyl ((R 12) 2N-CO), ureido (R 12R 12N-CO-NR 12), sulfonamide (R 12R 12-SO 2-), guanidium group (R 12R 12N-C(=NH 2 +>)-NR)(An ->) or halo; or CR 2R 2, CR 3R 3, CR 4R 4condensed cycle; R 111-4C alkyl; R 12H or 1-4C alkyl; x : 1 or 2; y : 0 or 1; Y 1H, alkali metal, alkaline earth metal, ammonium group of formula (N +>Ralpha Rbeta Rgamma Rdelta ), phosphonium group of formula (P +>Ralpha Rbeta Rgamma Rdelta ), or protecting group of functional thiol; Ralpha , Rbeta , Rgamma , Rdelta : H or 1-4C alkyl; and An ->anionic counter-ion, where the electroneutrality of (I) being assured by one or more An ->anions. Provided that: when x is 2 then y is 0; when x is 1 then y is 1; the bond a in (IIa), (IIb), (III), (IV), (Va), (Vb), or (VI) connects the groups W 1-W 5at N, in the case of formulae (IIa), (IIb), (Va), (Vb), when two R 2radical carried by two atoms of adjacent carbons form an aromatic cycle such as benzyl; the bond a 1in (IV) connects the groups W 3and X; and the bond b in (Va) or (Vb) connects the groups W 4and L. Independent claims are included for: (1) a dye composition comprising a dye compound (A) in a cosmetic medium; (2) a method of coloring of keratin fibers, comprising applying the composition comprising (A) on keratin fibers; and (3) a multi-compartment device comprising: a first compartment containing a dye composition; and a second compartment containing a reducing agent. [Image] [Image].