Patent FR-2788690-A1 (FR)
Title: Naphthalene cationic coupler for use in compositions for oxidation-dyeing of keratinic fibres, especially hair, contains at least one 2-hydroxynaphthalene including specified cationic group
Inventor: VANDENBOSSCHE JEAN JACQUES
IPC: A61K8/49
Filed: 1999-01-21
Abstract: Naphthalene cationic couplers are new.  Patent refers to oxidation-dyeing composition(s) A, containing (in dye-appropriate medium) at least one oxidation-base, and at least one coupler selected from compounds of formula (I) (and their acid-addition salts). R1, R2 and R3 = H, halogen, Z , 1-6C alkyl radical, (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 radicals, or carboxy-, (1-6C)alkyl carboxy-, (1-6C)alkyl sulfonyl-, aminosulfonyl-, N-Z aminosulfonyl-, etc.; R4  = 1-6C alkyl radical, Z, aryl (or benzyl) radical, 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-aminosulfonyl-, aminosulfonyl-, and amino- (1-6C)alkyl radicals; etc. Z = unsaturated cationic groups of formula (II), (III) or saturated cationic 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 = second group Z identical or different to first, halogen atom, hydroxyl radical, (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 carbamyl, or sulfonyl) radicals, or groups NHR'' or NR''R''';  R'', R'''  = identical or different (1-6C) alkyl radical, monohydroxy (1-6C) alkyl- or polyhydroxy (2-6C) alkyl- radical; R5 = (1-6C) alkyl radical, monohydroxy (1-6C) alkyl- or polyhydroxy (2-6C) alkyl- radical, benzyl radical, cyano-, tri(1-6C)alkyl silane-, (1-6C) alkoxy or (1-6C) alkyl carboxy- (1-6C) alkyl radical; or second Z group identical or different from first; R6, R7 and R8 = (1-6C) alkyl radical, monohydroxy (1-6C) alkyl- or polyhydroxy (2-6C) alkyl- radical, (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 carbonyl- radical, or two of R6-R8 radicals may form with N atom 1-6C saturated cycle which may contain one or more hetero-atoms and may be substituted with halogen, hydroxyl radical, (1-6C) alkyl radical, monohydroxy (1-6C) alkyl- or polyhydroxy (2-6C) alkyl- radical, 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 R6-R8 may represent second Z group identical or different from the first; R9 = (1-6C) alkyl radical, monohydroxy (1-6C) alkyl- or polyhydroxy (2-6C) alkyl- radical, aryl or benzyl radical, amino-(1-6C) alkyl radical 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 radical;  X = monovalent or divalent anion;  a and y = 0-1. Independent claims are included for: (1) a process of dyeing keratin fibres (especially hair) comprising application of composition A, 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; (2) a dyeing kit comprising separate compartments of which the first contains dyeing composition A and the second contains oxidant composition B;and (3) a compound of formula (I') (and its acid-addition salts), exclusive of 6-hydroxy- N,N,N-trimethyl- 1-naphthalene methanaminium chloride and ((2-hydroxy-1-naphthyl) methyl) trimethyl ammonium iodide; and 4) the use of compounds (I') as coupler for oxidation-dyeing of keratinic fibres. R1'-R3' = R1-R3 as in (I); when two of R1'-R3' are simultaneously H, the third radical contains amido- or carboxy group, however those groups are not directly joined to naphthol cycle.