Patent EP-0984007-A1 (EP)
Inventor: GENET ALAIN
IPC: C09B57/00
Filed: 1999-07-28
Abstract: Cationic o-phenylenediamine derivatives (I) are new. o-Phenylenediamine derivatives of formula (I) and their acid-addition salts are new. R1-R3 = H, halogen, Z, COA, COA'NH2, COA'NHZ, COA'NHA, COA'NA2, A'COA'NH2, A'COA'NHZ, A'COA'NHA, A'COA'NA2, COOH, COOA, SO2A, SO2NH2, SO2NHZ, SO2NHA, SO2NA2, A'SO2NH2, A'SO2NHZ, A'SO2NHA, A'SO2NA2, CONH2, CONHA, CONA2, A'CONH2, A'CONHA, A'CONA2, A, A'OH, 2-6C polyhydroxyalkyl, A'OA, A'', CN, OR6 or SR6; an amino group protected by COA, COOA, COA'', COA'NH2, COA'NHZ, COA'NHA, COA'NA2, CONH2, CONHA, CONA2, SO2A, SO2NH2, SO2NHZ, SO2NHA, SO2NA2, CSNH2, CHO or Z'; or 1-6C aminoalkyl N-substituted by 1 or 2 of A, A'OH, 2-6C polyhydroxyalkyl, COA, CONH2, CONHA, CONA2, SO2A, CHO, COA'', COOA, CSNH2 or Z; A = 1-6C alkyl; A' = 1-6C alkylene; A'' = 1-6C trifluoroalkyl; R6 = A, A'OH, 2-6C polyhydroxyalkyl, Z, A'OA, aryl, benzyl, A'COOH, A'COOA, A'CN, A'CONH2, A'CONHA, A'CONA2, A, A'SO2NH2, A'SO2NHZ, A'SO2NHA, A'SO2NA2, A'SOA, A'SO2A, A'COA or A'NH2; or 1-6C aminoalkyl N-substituted by 1 or 2 of A, A'OH, 2-6C polyhydroxyalkyl, COA, CHO, COA'', COOA, CONH2, CONHA, CONA2, CSNH2, SO2A and Z; R4, R'4, R5, R'5 = H, Z, A, A'OH, 2-6C polyhydroxyalkyl, Z, A'OA, aryl, benzyl, A'COOH, A'COOA, A'CN, A'CONH2, A'CONHA, A'CONA2, A'', A'SO2NH2, A'SO2NHZ,, A'SO2NHA, A'SO2NA2, A'SOA, A'SO2A, A'COA or A'NH2; or 1-6C aminoalkyl N-substituted by 1 or 2 of A, A'OH, 2-6C polyhydroxyalkyl, COA, CHO, COA'', COOA, CONH2, CONHA, CONA2, CSNH2, SO2A and Z; Z = a group of formula (i)-(iii): D = alkylene optionally interrupted by one or more heteroatoms and optionally substituted by OH, 1-6C alkoxy and/or oxo; E, G, J, L, M = C, O, S or N; n = 0-4; m = 0-5; R = Z, halogen, OH, A, A'OH, 2-6C polyhydroxyalkyl, NO2, CN, A'CN, OA, A'SiA3, CONH2, CHO, COOH, COA, SH, A'SH, SA, NH2, NHCOA, NHCONH2, NHSO2A, NHR'' or NR''R'''; R'', R''' = A, A'OH or 2-6C polyhydroxyalkyl; R9 = A, A'OH, 2-6C polyhydroxyalkyl, A'CN, A'SiA3, A'OA, A'CONH2, A'COOA, benzyl or Z; R10-R12 = A, A'OH, 2-6C polyhydroxyalkyl, A'OA, A'CN, aryl, benzyl, A'CONH2, A'SiA3, A'NHCOA, A'NHCONH2 or A'NHSO2A; or two of R7-R9 form a 5- or 6-membered ring optionally substituted by halogen, OH, A, A'OH, 2-6C polyhydroxyalkyl, NO2, CN, A'CN, OA, A'SiA3, CONH2, CHO, COOH, COA, SH, A'SH, SA, NH2, NHCOA, NHCONH2 or NHSO2A; or one of R10-R12 can be Z; R13 = A, A'OH, 2-6C polyhydroxyalkyl, aryl, benzyl, A'NH2, A'NHCOA, A'NHCONH2, A'NHSO2A, A'COOH, A'CN, A'CONH2, A'', A'SiA3, A'SO2NH2, A'COOA, A'SOA, A'SO2A, A'COA, A'CONHA or A'SO2NHA; Z' = Z in which B has an oxo group directly attached to the N atom; x, y = 0 or 1; and X<-> = a mono- or divalent anion; provided that: (A) when Z is of formula (i), then: (a) D is attached to the nitrogen atom when x = 0; (b) D is attached to E, G, J or L when x = 1; and (c) y can be 1 only if R9 is bonded to the ring N atom when E, G, J and L are all C or if at least one of E, G, J and L is a N atom to which R9 is bonded; (B) when Z is of formula (ii), then: (a) D is attached to the nitrogen atom when x = 0; (b) D is attached to E, G, J or L when x = 1; and (c) y can be 1 only if at least one of E, G, J, L and M is a divalent atom and R9 is bonded to the ring N atom; (C) when Z is a group of formula (iii), then: (a) D is attached to the N atom bearing R10 and R11 when x = 0; and (b) D is attached to a C atom of a saturated ring formed by R10 and R11 when x = 1; (D) at least one Z group is present; and (E) when R4, R5, R'4 and/or R'5 is a Z group in which D has an oxo group, this oxo group is not directly attached to the N atom of NR4R5 or NR'4R'5. Independent claims are also included for the following: (1) a composition for oxidation dyeing of keratinic fibers, containing at least one compound (I); (2) a method for oxidation dyeing of keratinic fibers, comprising applying at least one composition as in (1) to the fibers for a time sufficient for the desired color to develop, either in air or with the aid of an oxidizing agent; (3) a kit comprising a compartment containing the composition of (1) and a compartment containing an oxidizing composition.