Patent EP-2075289-A1 (EP)
Inventor: GREAVES ANDREW
IPC: A61Q5/06
Filed: 2008-09-19
Abstract: Fused pyridinium thiol/sulfide compounds (A) and their organic or mineral acid salts, optical isomers, geometrical isomers, solvates or hydrates, useful as fluorescent dye, are new. Fused pyridinium thiol/sulfide compounds (A) of formula (I) or (II) and their organic or mineral acid salts, optical isomers, geometrical isomers, solvates or hydrates, useful as fluorescent dye, are new. Ring A : aryl, heterocycle, heteroaryl fused with phenyl ring or absent; G, G1a : -NR cR dor 1-6C alkoxy (optionally substituted); either R c, R dH, 1-6C alkyl (optionally substituted), aryl(1-4C)alkyl or (1-6C)alkoxy(1-6C)alkyl; or NR cR dheterocycle or heteroaryl; either R g, R1g, R2g, R3g, R h, R1h, R2h, R3h : H (preferred), halo, amino, (di)(1-4C)alkylamino, CN, carboxy, OH, CF 3, acylamino, 1-4C alkoxy, 2-4C (poly)hydroxyalkoxy, (1-4C)alkylcarbonyloxy, (1-4C)alkoxycarbonyl, (1-4C)alkylcarbonyl-amino, acylamino, carbamoyl, (1-4C)alkylsulfonylamino, amino-sulfonyl or 1-16C alkyl (optionally substituted by 1-12C alkoxy, OH, CN, carboxy, amino or (di)(1-4C)alkylamino), where the two alkyl together with nitrogen of the group amino form 5-7 membered heterocycle (optionally containing another heteroatom same or different to the one of the nitrogen atom); or R gR1g, R2gR3g together with two atoms of adjacent C : benzo ring, indeno ring, fused heterocycloalkyl or fused heteroaryl (all optionally substituted by halo, 1-4C alkyl, amino, (1-4C) alkylamino, (1-4C)dialkylamino, CN, carboxy, OH, CF 3, acylamino, 1-4C alkoxy, 2-4C (poly)hydroxyalkoxy, alkylcarbonyloxy, alkoxycarbonyl, alkylcarbonylamino, acylamino, carbamoyl, alkylsulfonylamino, amino-sulfonyl or 1-16C alkyl (optionally substituted by 1-12C alkoxy, OH, CN, carboxy, amino, 1-4C alkylamino or 1-4C dialkylamino, where the two alkyl together with nitrogen of the group amino form 5-7 membered heterocycle (optionally containing another heteroatom same or different to the one of the nitrogen atom))); or R cR1g, R dR g, R cR2g, R dR3g (when G, G1a is -NR cR d) : heteroaryl or saturated heterocycle (optionally substituted by one or more 1-6C alkyl); either R1i, R2i, R3i, R4i : H (preferred) or 1-4C alkyl; or CR1hR2i, CR2hR3i : 5-7C cycloalkyl (optionally substituted) or fused pyridinium group; R 1-R 4, R1a, R2a, R3a, R4a : H (preferred), 1-4 alkyl, 1-12C alkoxy, OH, CN, -C(O)O ->M +>, carboxy or (di)(1-4C)(alkyl)amino, where alkyl radical together with nitrogen form 5-7 membered heterocycle (optionally containing another heteroatom different from N); M +>alkaline metal (in which An ->is absent); T a, T bcovalent sigma bond, -SO 2-, - O -, -S-, -N(R)-, -N +>(R)(R 0)-, -C(O)- or heterocycloalkyl or heteroaryl (both optionally cationic and preferably monocyclic); R, R 0H, 1-4C alkyl, 1-4C hydroxyalkyl or aryl(1-4C)alkyl; m, m1, n, n1 : 0-6, where m+n and m1+n1 are 1-10; An ->anionic counter ion; Y 1>H, alkaline metal, alkaline earth metal, ammonium group of formula (N +>Ralpha Rbeta Rgamma Rdelta ), phosphonium group of formula (P +>Ralpha Rbeta Rgamma Rdelta ) or thiol protecting group; and Ralpha , Rbeta , Rgamma , Rdelta : H or 1-4C alkyl. Provided that: the radical R1h or R2h and the styryl group carrying the radical R2i or R3i are positioned on the adjacent carbon atom of groups pyridinium group; and when (A) contains another cationic part, then it is associated with one or more anionic counter ion to achieve electroneutrality. Independent claims are included for: (1) a coloring composition comprising at least one fluorescent dyes (A) in cosmetic medium; (2) a method of coloring keratin materials, comprising applying the composition on the keratin fibers, optionally in the presence of a reducing agent; and (3) a multi-compartment device comprising a first compartment containing the coloring composition, and a second compartment containing a reducing agent. [Image] [Image].