Patent EP-1671955-A1 (EP)
Title: Cationic symmetric imidazole diazocompounds  with a non cationic linking group, compositions comprising them, dying process and kit thereof
Inventor: DAVID HERVE
IPC: C07D233/88
Filed: 2005-12-14
Abstract: Cationic dissymmetrical diazo compounds (I), their resonance forms, acid addition salts an acid and/or their solvates are new. Cationic dissymmetrical diazo compounds of formula (I) (where electroneutrality of (I) is ensured by one or more anions (An)), their resonance forms, acid addition salts an acid and/or their solvates are new. R 11-4C alkyl, phenyl or benzyl (all optionally substituted); R 3X or 1-16C alkyl (optionally substituted, and optionally interrupted by one or more heteroatoms or groups containing heteroatoms (preferably O, N, S, -CO and/or -SO 2)); X : OH, 1-4C alkoxy, 2-4C (poly)hydroxyalkoxy, RO-CO-, RCO-O-, R-CO-, amino (optionally substituted by one or two radicals 1-4C alkyl (optionally carrying OH), where the two alkyl radicals with N optionally form T), alkylcarbonylamino (RCO-NR 1-), aminocarbonyl ((R1) 2N-CO), ureido (N(R 1) 2-CO-NR1), aminosulfonyl ((R1) 2N-SO 2), alkylsulfonylamino (RSO 2-NR 1-), alkylsulfinyl (R-SO-), alkylsulfonyl (R-SO 2-), nitro, CN, halo (Cl or F), HS- or RS; R 2X, 1-16C alkyl (optionally substituted by HS, 1-4C thioalkyl, 1-4C alkylsulfinyl or 1-4C alkylsulfonyl, and optionally interrupted by one or more heteroatoms or groups containing heteroatoms (preferably O, N, S, -CO and/or -SO 2)), substituted aryl or 1-4C arylalkyl (optionally substituted); e, m1 : 0-4; T : 5-7 membered optionally aromatic heterocycle (containing 1-3 (preferably 1-2) heteroatoms N (preferred), O or S); W 1H, halo (Br, Cl or F (preferably Cl or F)), NR 5R 6, OR 7, -NR 4-Ph-NR 5R 6, -NR 4-Ph-OR 7, -O-Ph-OR 7 or -O-Ph-NR 5R 6; R 4, R 71-20C (preferably 1-16C) alkyl, 1-3C aralkyl, phenyl (all optionally substituted) or H; either R 5, R 61-20C (preferably 1-16C) alkyl, 1-3C aralkyl, phenyl (all optionally substituted), H or R-CO-; or NR 5R 6T; or R 5 + R 6 + C (of aromatic cycle adjacent to that to which -NR 5R 6 is attached) : 5-6 membered saturated heterocycle; Ph : optionally substituted phenyl; L : covalent bond, 1-40C (preferably 1-20C) alkyl (optionally substituted and optionally interrupted by 3-7 membered optimally aromatic heterocycle (optionally fused and optionally substituted), one or more heteroatoms or groups containing heteroatoms (O, N, S, CO and/or SO 2)) or optionally substituted phenyl; R : 1-4C alkyl; and R 1H or R. Provided that when e is 2, then two adjacent R 2 together forms with carbon atom to which they are attached a 5-6 (preferably 6) membered secondary cycle (optionally substituted by 1-4C alkyl, 1-4C alkoxy, 2-4C (poly)hydroxyalkoxy or amino (optionally substituted by 1-4C alkyl (optionally carrying OH)). Provided that when m1 is 2, then two adjacent R 3 together forms with carbon atom to which they are attached a 6 membered secondary cycle (optionally substituted by OH, 1-4C alkyl, 1-4C alkoxy, 2-4C (poly)hydroxyalkoxy or amino (optionally substituted by 1-4C alkyl (optionally carrying OH)). Provided that when e and m1 are lower than 4, the carbon atoms of unsubstituted heterocycle carry a hydrogen atom. Provided that OR 7 and NR 5R 6 groups form substitutions i.e. when two adjacent R 3 form a 6-membered aromatic ring, which is optionally substituted by NR 4-Ph, NR 4-Ph-OR 7 or NR 4-Ph-NR 5R 6. Provided that L is not azo, nitro, nitroso or peroxo. Independent claims are included for: (1) a tinctorial composition (A) comprising (I), in a medium for the dyeing of keratinous fibers, as direct dye; (2) a process of dyeing keratinous fiber comprising contacting (A) with the dry or wet fibers to obtain the desired effect; and (3) a device with several compartments, comprising a first compartment comprising (A) and a second compartment containing an oxidizing composition. [Image] .