Nouvelles bases d'oxydation cationiques, leur utilisation pour la teinture d'oxydation des fibres keratiniques, compositions tinctoriales et procedes de teinture

Cationic oxidation bases for use in compositions for oxidation-dyeing of keratin fibres, especially hair dyes, comprise pyrazolo (1,5-a) pyrimidines containing cationic groups including quaternized cycles

Abstract

New pyrazolo (1,5-a) pyrimidines and their addition salts with acids are claimed. The new pyrazole derivatives are of formula (I). R1, R2 and R3 = H, halogen, Z (as defined below), 1-6C alkyl, (1-6C)alkyl carbonyl-, amino(1-6C)alkyl carbonyl, N-Z-amino-(1-6C) alkylcarbonyl, N-(1-6C)alkyl-amino-(1-6C) alkylcarbonyl, or N,N-di(1-6C)alkyl-amino-(1-6C) alkylcarbonyl- radicals, or amino-(1-6C)-alkyl-carbonyl, N-Z-amino-(1-6C) alkylcarbonyl-, N-(1-6C)alkyl-amino-(1-6C) alkylcarbonyl-, or N,N-di(1-6C)alkyl-amino-(1-6C) alkylcarbonyl- (1-6C) alkyl, or carboxy-, (1-6C)alkylcarboxy-, (1-6C)alkylsulfonyl-, aminosulfonyl-, N-Z aminosulfonyl-, or N(or N, N) (1-6C) (di)alkyl aminosulfonyl, or amino-sulfonyl-, N-Z aminosulfonyl-, or N(or N, N) (1-6C) (di)alkyl aminosulfonyl- (1-6C) alkyl, etc. R6 = (1-6C) alkyl , mono (or poly)hydroxy (1-6C)alkyl, Z, aryl or benzyl, (1-6C) alkoxy-, carboxy-, (1-6C)alkyl carboxy-, cyano-, carbamyl-, N-(1-6C)alkyl-carbamyl-, N,N-di(1-6C)alkylcarbamyl-, trifluoro-, aminosulfonyl-, N-Z aminosulfonyl-, N(1-6C)alkylaminosulfonyl-, N,N-di(1-6C)alkyl aminosulfonyl-, (1-6C) alkyl sulfinyl- (or sulfonyl-, or carbonyl-), or amino- (1-6C) alkyl, 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, (1-6C)alkyl carbonyl (or sulfonyl), formyl, or trifluoro-(1-6C) alkyl-carbonyl- radicals, or Z; A = NR4R5 or hydroxyl radical; R4, R5 = H, Z, 1-6C alkyl, aryl (or benzyl), trifluoro-, mono(or poly)- hydroxy-, (1-6C)-alkoxy, cyano, carbamyl, N-(or N,N) (1-6C)-(di) alkylcarbamyl, thiocarbamyl, sulfo, (1-6C)-alkyl-carboxy-, (1-6C) alkyl carbonyl-, (1-6C)alkyl sulfinyl-, aminosulfonyl-, N-Z-aminosulfonyl-, N-(1-6C)alkyl-aminosulfonyl-, N,N-di(1-6C)alkyl-aminosulfony-l, aminosulfonyl-, and amino- (1-6C)alkyl; etc. Z = unsaturated groups of formula (II) or (III) or saturated groups of formula (IV); D = (preferably 1-14C) linear or branched chain, which may be interrupted with one or more heteroatoms (N, O or S) and substituted with one or more hydroxyl or 1-6C alkoxy radicals, and may have one or more ketone groups; E,G, J, L and M = C, O, S or N; n = 0-4; m = 0-5; R = same or different, represent Z, halogen, hydroxyl, (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-, aldehydo-, carboxyl-, thio-, (1-6C) alkyl carbonyl, thio-(1-6C) alkyl, (1-6C)alkyl-thio- and amino- radicals, with amino- radical protected with (1-6C)alkyl carbonyl- (or sulfonyl) radicals, or groups NHR'' or NR''R'''; R'', R''' = (1-6C) alkyl, monohydroxy (1-6C) alkyl- or polyhydroxy (2-6C) alkyl; R7 = (1-6C) alkyl, monohydroxy (1-6C) alkyl- or polyhydroxy (2-6C) alkyl, benzyl, cyano, tri(1-6C)alkyl silane, (1-6C) alkoxy or (1-6C) alkyl carboxy- (1-6C) alkyl; or group Z; R8, R9 and R10 = (1-6C) alkyl radical, monohydroxy (1-6C) alkyl- or polyhydroxy (2-6C) alkyl, (1-6C) alkoxy, cyano, amido- or tri(1-6C)alkyl silane- (1-6C) alkyl radical, or amino-(1-6C)alkyl radical with amine protected by (1-6C) alkyl sulfonyl- or amido, carboxy- or carbonyl- radical, or two of R8-R10 radicals may form with N atom 5-6 links saturated cycle which may contain one or more hetero-atoms and may be substituted with halogen, hydroxyl, (1-6C) alkyl, monohydroxy (1-6C) alkyl- or polyhydroxy (2-6C) alkyl, 1-6C alkyl-thio- or alkoxy, nitro, cyano, amido-, aldehydo-, 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) radical, or one of R8-R10 may represent second Z group identical or different from the first; R11 = (1-6C) alkyl l, monohydroxy (1-6C) alkyl- or polyhydroxy (2-6C) alkyl, aryl or benzyl, amino-(1-6C) alkyl with amine optionally 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; X = monovalent or divalent anion; a and y = 0-1. Independent claims are included for: (1) use of compounds (I) as oxidation base for oxidation-dye for keratinic fibres; (2) composition A for oxidation-dyeing of keratinic fibres, including oxidation base containing at least one compound (I) (preferably in amount 0.0005-12 (especially 0.005-6) wt.%), optional additional oxidation base, at least one coupler, and/or at least one direct colorant; (3) process of dyeing keratin fibres (especially hair) comprising application of composition A as claimed, which produces 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; and (4) dyeing kit comprising separate compartments of which the first contains dyeing composition A as claimed and the second contains oxidant composition B.
<P>L'invention a pour objet de nouvelles pyrazolo [1,5-a] pyrimidines comportant au moins un groupement cationique Z, Z étant choisi parmi des chaînes aliphatiques quaternisées, des chaînes aliphatiques comportant au moins un cycle saturé quaternisé, et des chaînes aliphatiques comportant au moins un cycle insaturé quaternisé, leur utilisation à titre de base d'oxydation pour la teinture d'oxydation des fibres kératiniques, les compositions tinctoriales les contenant, ainsi que les procédés de teinture d'oxydation les mettant en oeuvre.</P>

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Patent Citations (1)

    Publication numberPublication dateAssigneeTitle
    WO-9749378-A1December 31, 1997L'orealPYRAZOLO-(1,5-a)-PYRIMIDINE DERIVATIVES, THEIR PREPARATION AND HAIR DYES CONTAINING THESE

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Cited By (3)

    Publication numberPublication dateAssigneeTitle
    EP-1935456-A1June 25, 2008L'OréalOxidation dye composition containing a cationic surface-active agent, a bioheteropolysaccharide, an amphoteric surface-active agent and a dye precursor
    US-7674299-B2March 09, 2010L'oreal S.A.Direct dye composition comprising a cationic surfactant, a bioheteropolysaccharide, an amphoteric surfactant and direct dye
    US-7799094-B2September 21, 2010L'oreal S.A.Oxidation dye composition comprising a cationic surfactant, a bioheteropolysaccharide, an amphoteric surfactant and a dye precursor