Patent EP-1484049-A1 (EP)
Title: Imidazole compounds and their use for dyeing of keratinous fibres
Inventor: MAVRO JACQUELINE
IPC: C07D233/88
Filed: 2004-05-28
Abstract: Oxidation dye composition comprises one or more developers and an imidazole coupler (I). Oxidation dye composition comprises one or more developers and an imidazole coupler of formula (I) or a salt thereof. [Image] R 1, R 2H; phenyl optionally substituted with halo, OH, 1-4C alkoxy, COOH, CONH 2, 1-4C alkylsulfonyl, SO 3H, alkylsulfinyl, alkylsulfonamido, NR 1 3R 1 4 and Q; or 1-8C alkyl optionally substituted with OH, 1-4C alkoxy, COOH, CONH 2, 1-4C alkylsulfonyl, SO 3H, alkylsulfinyl, alkylsulfonamido or NR 1 3R 1 4; or NR 1R 2 is a 5- to 8-membered heterocycle in which C atoms can be replaced by O, N, S or SO 2 and C atoms can be substituted with R 5; Q : 1-4C alkyl optionally substituted with OH, 1-4C alkoxy, COOH, CONH 2, 1-4C alkylsulfonyl, SO 3H, alkylsulfinyl, alkylsulfonamido or NR 1 3R 1 4; R 4R 1, R 2, NR 2 2R 2 3 or 5- or 6-membered heteroaryl optionally substituted with OH, 1-2C alkoxy, NH 2, dimethylamino, 2-hydroxyethylamino, bis(2-hydroxyethyl)amino and Cl; R 2 2, R 3 3H, acyl or 1-2C alkyl optionally substituted with OH or 1-2C alkoxy; R 5halo; 1-4C alkyl optionally substituted with OH, COOH, 1-4C alkoxycarbonyl, 1-4C alkoxy or NR 6R 7; COOH; CONH 2; 1-4C alkylsulfonyl; alkylsulfonamido; OH; 1-4C alkoxy; 2-4C hydroxyalkoxy; SO 2NH 2; 1-4C alkylthio; 1-4C alkylsulfinyl; 1-4C alkylsulfonyl; or NR 8R 9; R 3H; 1-4C alkylsulfonyl; 1-8C alkyl optionally substituted with OH, OR 1 0, COOH, CONH 2, 1-4C alkylsulfonyl, SO 3H, 1-4C alkylsulfinyl, alkylsulfonamido or NR 1 1R 1 2; or phenyl or 5- or 6-membered heteroaryl optionally substituted with halo, OH, 1-4C alkoxy, COOH, CONH 2, 1-4C alkylsulfonyl, SO 3H, alkylsulfinyl, alkylsulfonamido, NR 1 3R 1 4 and Q; R 1 01-4C alkyl optionally substituted with OH, 1-2C alkoxy, NH 2, mono- or di(1-4C alkyl)amino or 2-4C (poly)hydroxyalkylamino; R 6-R 9, R 1 1-R 1 4H, acyl, CONH 2 or Q'; or NR 1 1R 1 2 is a 5- to 8-membered ring optionally substituted with halo, OH, 1-4C alkoxy, COOH, CONH 2, 1-4C alkylsulfonyl, SO 3H, alkylsulfinyl, 1-4C thioether, alkylsulfonamido, NR 1 3R 1 4 and Q; Q' : 1-4C alkyl optionally substituted with OH, 1-4C alkoxy, COOH, CONH 2, 1-4C alkylsulfonyl, SO 3H, alkylsulfinyl, alkylsulfonamido, NH 2, mono- or di(1-4C alkyl)amino or 2-4C (poly)hydroxyalkylamino; and X : H; halo; 1-4C alkoxy; phenoxy optionally substituted with halo, OH, 1-4C alkoxy, 1-4C alkoxycarbonyl, CONH 2, sulfino, 1-4C alkylsulfonyl, SO 3H, alkylsulfinyl, 1-4C thioether, alkylsulfonamido, NR 1 3R 1 4 and 1-4C alkyl; or 1-4C thioether optionally substituted with OH, 1-2C alkoxy, COOH, SO 3H and CONH 2. Independent claims are also included for: (1) oxidation dyeing of keratinic fibers by applying the due composition in the presence of an oxidizing agent; (2) kit comprising the dye composition in one compartment and an oxidizing agent in another compartment; (3) new compounds (I) with the definitions given below. X : H, Cl or Br; 1-4C alkoxy; or 1-4C thioether optionally substituted with OH, 1-2C alkoxy, COOH, SO 3H and CONH 2; R 1-R 4groups as defined above, except that R 3 must be 1-8C alkyl substituted with at least 2 of OH, 1-4C alkoxy, COOH, CONH 2, SO 3H or NR 1 1R 1 2, or phenyl optionally substituted with halo, OH, 1-4C alkoxy, COOH, CONH 2, NR 1 3R 1 4 and 1-4C alkyl, when X is H, Cl or Br.