Patent EP-1129690-B1 (EP)
Inventor: BRETON PHILIPPE
IPC: A61K8/36
Filed: 2001-02-19
Granted: 2005-01-05
Abstract: The use of cationic indolizine derivatives as couplers in oxidation-dye compositions, some of these derivatives, and the method of hair dyeing using these compositions are new. The composition contains a) at least one oxidation base and b) a coupler, in form of at least one indolizine derivative (and/or at least one of its acid addition salt) of formula (I); n = 0-4; R1 and R3 = H or halogen atom; group Z; 1-4C alkyl, alkoxy or monohydroxy-alkyl; 2-4C polyhydroxy- alkyl; 1-4C amino- or acetylamino- alkyl; acetylamino; 1-4C alkoxy- 1-4C alkyl; mono- (or di-)1-4C -alkyl- amino 1-4C alkyl; aminocarboxy- 1-4C- alkyl; acetyl 1-4C-alkyl- amino 1-4C alkyl; or aromatic cycle, non-substituted or substituted with one or more radicals selected from halogen atom, 1-4C alkyl or alkoxy, trifluoromethyl, amino, and amino mono- or di- substituted with 1-4C alkyl radical, mono- (or di-)1-4C -alkyl- amino 1-4C alkyl, carboxyl or sulfoxy radical; where R-3 can also be unsaturated heterocycle consisting of 5-6 links; R2 and R4 = H or halogen atom; group Z; 1-4C alkyl, alkoxy or monohydroxy-alkyl; 2-4C polyhydroxy- alkyl; mono- (or di-)1-4C -alkyl- amino 1-4C alkyl; carboxy; cyano; carboxy- 1-4C alkyl; nitro or 5-6C aromatic cycle non-substituted or substituted with one or more radicals selected from halogen atom, 1-4C alkyl or alkoxy, trifluoromethyl, amino, and amino mono- or di- substituted with 1-4C alkyl radical, mono- (or di-)1-4C -alkyl- amino 1-4C alkyl, carboxyl or sulfoxy radical; Z = unsaturated cationic group of formula (II) or (III) or saturated cationic group of formula (IV); D = linear or branched 1-14C (preferably) alkyl chain optionally interrupted by one or more heteroatoms O, S or N, and optionally substituted with one or more hydroxyl or 1-6C alkoxy radicals, also capable of bearing one or more ketone groups; E, G, J, L and M = C, O, S or N atom; b = 0-4, m = 0-5; R = identical or different second Z group identical or different from the first one; halogen atom; hydroxyl radical, 1-6C alkyl, 1-6C mono-hydroxy alkyl, 2-6C polyhydroxy- alkyl; nitro or cyano; 1-6C cyanoalkyl; 1-6C alkoxy; tri-1-6C alkyl-silane 1-6C alkyl; amido, aldehydo, carboxyl or thio group; 1-6C alkyl- carbonyl or thio; thio- 1-6C alkyl; amino; amino protected with 1-6C alkyl carbamyl, carbonyl or sulfonyl; NHR'' or NR''R'''; R'' and R''' = 1-6C alkyl or monohydroxy alkyl or 2-6C polyhydroxy alkyl; R5 = 1-6C alkyl, 1-6C mono-hydroxy alkyl, 2-6C polyhydroxy- alkyl; 1-6C cyanoalkyl; 1-6C alkoxy- or tri-1-6C alkyl-silane 1-6C alkyl; 1-6C carbamyl alkyl; 1-6C alkyl-carboxy 1-6C alkyl, benzyl or second Z group identical or different from the first one; R6, R7 and R8 = identical or different 1-6C alkyl, 1-6C mono-hydroxy alkyl, 2-6C polyhydroxy- alkyl; alkoxy- or cyano- 1-6C alkyl; aryl; benzyl; 1-6C amido alkyl, tri-1-6C alkyl-silane 1-6C alkyl or 1-6C amino-alkyl where amine is protected with 1-6C alkyl carbamyl, carbonyl or sulfonyl; two of R6, R7 and R8 may also form, together with N atom to which they are attached, a saturated 5 or 6C cycle or heterocycle containing one or more heteroatoms, and optionally substituted with halogen atom, hydroxyl radical, 1-6C alkyl, 1-6C mono-hydroxy alkyl, 2-6C polyhydroxy- alkyl; nitro or cyano; 1-6C cyanoalkyl; 1-6C alkoxy; tri-1-6C alkyl-silane 1-6C alkyl; amido, aldehydo, carboxyl, 1-6C ketoalkyl, thio-, 1-6C alkyl- carbonyl or thio; thio- 1-6C alkyl; amino, amino protected with 1-6C alkyl carbamyl, carbonyl or sulfonyl; or one of R6-R8 may represent second Z group, identical or different from the first one; R9 = 1-6C alkyl, 1-6C mono-hydroxy alkyl, 2-6C polyhydroxy- alkyl; aryl; benzyl; 1-6C amino-alkyl, 1-6C amino-alkyl where amine is protected with 1-6C alkyl carbamyl, carbonyl or sulfonyl; 1-6C carboxy- carbamyl-, cyano- or trifluoro- alkyl; tri-1-6C alkyl-silane 1-6C alkyl; 1-6C sulfonamido- alkyl; 1-6C alkyl- carboxy (or sulfinyl, or sulfonyl) 1-6C -alkyl; 1-6C alkyl- keto- 1-6C alkyl; or N- 1-6C alkyl- carbamyl (or sulfonamido) 1-6C alkyl; a and y = 0 or 1; X<-> = monovalent or divalent anion, selected from halogen atom, hydroxide, hydrosulfate or 1-6C alkyl sulfate (Full definitions are given in DEFINITIONS (Full Definitions) field). The composition may also contain additional couplers and one or more direct colorants. Independent claims are also included for: (1) use of indolizine derivatives of formula (I) as claimed as couplers, in combination with at least one oxidation base, for oxidation-dyeing of keratin fibers, especially human hair; (2) process of oxidation-dyeing of hair, comprising application of at least one composition as claimed and revealing color at acidic, neutral or alkaline pH by means of oxidizing agent which is added at the moment of use of dyeing composition, or which is present in oxidizing composition applied simultaneously or sequentially, in separate fashion; (3) hair dyeing kit with number of compartments of which one contains the composition as claimed and another oxidizing composition; (4) indolizine derivatives of formula (I) excluding these containing cationic groups of formula (IV) and excluding 4-methyl-4- (2-(2-phenyl- 1-indolizinyl) -ethyl)- morpholinium bromide; and (5) the use of indolizine derivatives as claimed in (4) as couplers in oxidation-dyeing of keratin fibers, especially hair.