Patent FR-2788521-A1 (FR)
Title: Cationic oxidation bases for use in compositions for dyeing keratin fibres such as hair dye compositions, consist of pyrazole derivatives with cationic groups containing optionally saturated quaternized rings
Inventor: TERRANOVA ERIC
IPC: C07D403/12
Filed: 1999-01-19
Abstract: Pyrazole derivatives comprising at least one cationic group comprising quaternized aliphatic chains, or chains comprising optionally saturated quaternized rings, are new.  Pyrazole derivatives, their addition salts with acids or bases, and possible tautomers, of formula (I): R1 = H, group (Z), 1-6C alkyl, trifluoroalkyl, hydroxy(1-6C)alkyl, or polyhydroxy(2-6C)alkyl, aryl (phenyl or aromatic hetero- (5-6 membered ring), di(1-6C alkyl)thio-, amino(1-6C-alkylcarbonyl(1-6C alkyl), N-Z-amino-(1-6C) alkylcarbonyl-, N-(1-6C)alkyl-amino-(1-6C) alkylcarbonyl-, N,N-di(1-6C)alkyl-amino-(1-6C) alkylcarbonyl-, aminosulfonyl-, N-Z-aminosulfonyl-, N-(1-6C)alkyl-aminosulfonyl- and N,N-di(1-6C)alkyl- aminosulfonyl- 1-6C alkyl radical;  R2, R3  = -NHR4 (at least one), hydroxyl radical (at least one), halogen, nitro-, cyano-, carboxy-, carboxy (1-6C)alkyl-, carboxy aryl-, carbamyl-, N-(or N,N) (1-6C) (di)alkyl (or aryl) carbamyl-, (1-6C)alkoxy-, aryloxy-, thio(1-6C)alkyl- or thioaryl- radical, or one of radicals listed for R1;  R4  = H, -Z, 1-6C alkyl radical, aryl (or benzyl) radical, trifluoro-, mono(or poly)- hydroxy-, (1-6C)-alkoxy-, cyano-, carbamyl-, N-(or N,N) (1-6C)-(di) alkyl carbamyl-, thio carbamyl-, sulfoalkyl-, (1-6C)-alkyl-carboxy-, (1-6C)alkyl sulfinyl-, aminosulfonyl-, N-Z-aminosulfonyl-, N-(1-6C)alkyl-aminosulfonyl-, N,N-di(1-6C)alkyl-aminosulfonyl-, aminosulfonyl-, and amino- (1-6C)alkyl radicals; with amine in the latter optionally substituted with one or two same or different radicals selected from (1-6C)alkyl- and mono(or poly)-hydroxy- (1-6C)alkyl radicals, (1-6C)alkyl carbonyl (or sulfonyl)-, formyl-, or trifluoro-(1-6C) alkyl-carbonyl- radicals, or Z, or with two radicals forming, jointly with amine N atom, (un)saturated 5-6 membered (hetero)cyclyl; Z  = groups of formula (II), (III) or (IV): D  = (preferably 1-14C) (non)branched alkyl, optionally interrupted with N, O or S, and optionally substituted with OH, or 1-6C alkoxy, or one or more ketone groups; E,G, J, L and M = C, O, S or N; n = 0-4; m = 0-5; R = halogen, OH, (1-6C) alkyl-, mono (or poly) hydroxy-, or cyano- (1-6C)alkyl radicals, nitro-, cyano-, 1-6C alkoxy-, tri(1-6C) silane (1-6C) alkyl-, amido-, formyl-, carboxyl, thio-, (1-6C) alkyl carbonyl-, thio-(1-6C) alkyl-, (1-6C)alkyl-thio- and amino- radicals, amino- radical protected with (1-6C)alkyl carbonyl- (or sulfonyl) radicals, or: NHR'' or NR''R'''; R'', R'''  = 1-6C alkyl, monohydroxy(1-6C) alkyl- or polyhydroxy (2-6C) alkyl- radical; R5 = 1-6C alkyl, monohydroxy (1-6C) alkyl- or polyhydroxy (2-6C) alkyl, aryl, benzyl, cyano-, tri(1-6C)alkyl silane-, 1-6C alkoxy or di(1-6C alkyl)carboxy; R6- R8 = 1-6C alkyl, monohydroxy 1-6C alkyl, or polyhydroxy (2-6C)alkyl-, 1-6C alkoxy-, cyano-, amido- or tri(1-6C)alkyl silane-, (1-6C) alkyl, or amino-(1-6C)alkyl radical with amine protected by (1-6C) alkyl sulfonyl- or carbonyl- radical; two of R6-R8 may form a N-containing 1-6C (sic) saturated hetero ring optionally substituted with halogen , hydroxyl, 1-6C alkyl, monohydroxy 1-6C alkyl- or polyhydroxy 2-6C alkyl-, 1-6C alkylthio- or alkoxy-, nitro-, cyano-, amido-, formyl-, carboxyl- or thio- radical, or cyano-, keto-, thio-, or tri-(1-6C)alkyl silane-(1-6C)alkyl radical, or amine radical, protected with (1-6C)alkyl carbonyl-(or sulfonyl); R9 = (1-6C) alkyl, 1-6C hydroxyalkyl- or polyhydroxy(2-6C) alkyl-, aryl (or benzyl), amino-(1-6C) alkyl optionally amine protected with (1-6C)alkyl carbonyl- (or sulfonyl)- radical; or carboxy-, cyano-, carbamyl-, trifluoro-, tri(1-6C)alkyl silane-, sulfonamido-, (1-6C) alkyl carboxy-, (1-6C)alkyl sulfinyl- (or sulfonyl-, or keto-)-, or N-(1-6C)alkyl carbamyl- (or sulfonamido-) (1-6C) alkyl radical; X = mono- or di-valent anion;  a, y  = 0-1 The full definitions are given in DEFINITIONS field. Independent claims are also included for the following: (1) A composition (A) for oxidation-dyeing of keratinic fibres, comprising: (a) oxidation base containing at least one compound of formula (I) (preferably 0.0005-12 (especially 0.005-6) wt.%),  (b) (optional) additional oxidation base,  (c) at least one coupler, and/or  (d) at least one direct colorant. (2) A process of dyeing keratin fibres (especially hair), involves applying composition (A) to produce color at acidic, neutral or alkaline pH with the aid of oxidant-agent, added at the application stage or present in oxidant composition (B) applied simultaneously or in sequence, separately from composition (A). (3) A dyeing kit comprising separate compartments for the first dyeing composition (A) and a second composition (B) containing an oxidant.