Patent FR-2920779-A1 (FR)
Title: New cationic azo julolidine compounds useful as dye for coloring keratin fibers, preferably human keratin fibers such as hair
Inventor: DAUBRESSE NICOLAS
IPC: A61K8/46
Filed: 2007-09-11
Abstract: Cationic azo julolidine compounds (I) and their organic or inorganic acid addition salts, solvates, tautomers, and optical and geometrical isomers as dye are new, where the electroneutrality of (I) is assured by one or more anionic counter-ions. Cationic azo julolidine compounds of formula (I) and their organic or inorganic acid addition salts, solvates, tautomers, and optical and geometrical isomers as dye are new, where the electroneutrality of (I) is assured by one or more anionic counter-ions. W 1cationic heteroaromatic radical comprising pyridinium radical of formula (IIa) or imidazole group of formula (IIb); L : sigma covalent bond or 1-20C bivalent hydrocarbon chain (optionally substituted and interrupted by one or more divalent groups and where the two divalent groups or their combinations are separated by 1-6C divalent hydrocarbon chain, preferably alkylene, comprising -N(R)-, -N +>(R)(R o)-, An ->, -O-, -S-, -C(O)-, cationic heterocycle or cationic heteroaryl (Het +>), non-cationic heterocycle comprising 5-10 membered chain or heteroaryl (optionally substituted)); R : 1-4C alkyl, 2-6C (poly)hydroxyalkyl, alkoxy(1-6C)alkyl, aryl, aryl(1-6C)alkyl, (1-4C)alkylcarbonylamino(1-6C)alkyl, amino(1-4C)alkyl of which amine is substituted by one or more 1-4C alkyl radical, alkyl(1-8C)carbonyl or 1-4C alkylcarbonylamino; R oH or R; Het +>5-10 membered cationic heterocycle (optionally saturated) or 5-10 membered cationic heteroaryl; R 11-6C alkyl, aryl, heteroaryl, aryl(1-6C)alkyl, heteroaryl(1-6C)alkyl (all optionally substituted), cycloalkyl(1-6C)alkyl or heterocycloalkyl(1-6C)alkyl; either R 21-4C alkyl, OH, 1-4C alkoxy, 2-4C (poly)hydroxyalkoxy, alkoxycarbonyl (R aC(O)-O-), alkylcarbonyloxy (R aC(O)-O-), amino group (optionally substituted by one or more 1-4C alkyl and optionally carrying at least one hydroxyl group, where the two alkyl radicals optionally together with nitrogen atom to form a 5 or 6 heterocyclic ring optionally substituted and carrying another heteroatom of N or O), alkylcarbonylamino group (R aC(O)-NR1a-), (di-)(alkyl)aminocarbonyl ((R a) 2N-C(O)), ureido group ((R a) 2N-CO-NR b-), guanidinium group ((R a) 2N-C(=NH 2>+)-NR b-), phenyl or halo; or CR 2R 26 membered condensed aromatic ring optionally substituted by one or more OH, 1-4C alkyl, hydroxycarbonyl (HO(O)C-), alkoxy carbonyl (R aO(O)C-), alkylsulfonylamino (R aS(O) 2NR b), 1-4C alkoxy, amino optionally substituted by one or two 1-4C alkyl and optionally carrying OH or methylcarbonylamino, where the two alkyl groups optionally together with nitrogen atom to form a 5 or 6 heterocyclic ring optionally carrying another heteroatom of N or O; Y 1H, alkaline metal, alkaline-earth metal, ammonium group (N +>Ralpha Rbeta Rgamma Rdelta ), phosphonium group (P +>Ralpha Rbeta Rgamma Rdelta ) or thiol protecting group; An : anionic counter-ion; R a, R b, Ralpha Rbeta Rgamma Rdelta : H or 1-4C alkyl; R1a : H or 1-4C alkyl; R 3H or R 2; R 4optionally substituted 1-6C alkyl or carboxy; m : 0-4; n : 0-6; x : 1 or 2; and y : 0 or 1. Provided that: L not comprising a group of diazo, hydrazino, aminooxy, nitro, nitroso and peroxide; when x is 2, then y is 0; when x is 1, then y is 1; the bond (a) in (IIa) and (IIb) connects the W 1group to N, preferably for (IIa), the bond (a) connects the pyridinium group to N in position 2 or 4, and for (IIb) the bond (a) connects the imidazolium groups to N in position 2, and in the case of formulae (IIa) and (IIb), when two R 2radicals carried by two adjacent carbon atoms form an aromatic cycle such; the bond (a) connects the W 1group to N by the intermediate of aromatic cycle; and the bond b in (IIa) or (IIa) connects the W 1group to the bond L by intermediate of methylene group. Independent claims are included for: (1) a coloring composition comprising (I) and at least a reducing agent; (2) a process for coloring keratin fibers comprising applying the composition on the fibers; and (3) a device with several compartments comprising a first compartment containing the composition and a second compartment containing a reducing agent. [Image] [Image].