Patent EP-1027879-B1 (EP)
Inventor: VANDENBOSSCHE JEAN-JACQUES
IPC: A61Q1/04
Filed: 2000-01-13
Granted: 2005-04-20
Abstract: Cationic heterocyclic polynuclear condensed compounds of formula (I) used as direct dyes in cosmetic compositions for coloring human hair and other keratinic materials.  Use, as direct dyes in compositions for coloring keratinic materials, of compounds of formula (I) and their acid addition salts;  R<1> = H; Z; aminoalkyl(1-6C) carbonylalklyl(1-6C); N-Z-aminoalkyl(1-6C)carbonylalkyl(1-6C); N-alkyl(1-6C)aminoalkyl(1-6C )carbonylalkyl(1-6C); N,N-dialkyl(1-6C)aminoalkyl(1-6C)carbonylalkyl(1-6C); aminosulfonylalkyl((1-6C); N-Z-aminosulfonylalkyl(1-6C ; N- alkyl(1-6C) aminosulfonyl alkyl(1-6C); N,N-di alkyl(1-6C)aminosulfonyl alkyl(1-6C); carbamyl alkyl(1-6C); N- alkyl(1-6C )carbamyl alkyl(1-6C ); N,N-di alkyl(1-6C) carbamyl alkyl(1-6C); alkyl(1-6C); monohydroxy alkyl(1-6C); polyhydroxyalkyl(2-6C) alkoxy(1-6C) alkyl(1-6C) or trifluoroalkyl(1-6C)  R<2>, R<3> = H; halogen; Z; 1-6C alkylcarbonyl; aminoalkyl(1-6C)carbonyl; N-Z-amino alkyl(1-6C)carbonyl; N- alkyl(1-6C)amino alkyl(1-6C)carbonyl; N,N-di alkyl(1-6C )amino alkyl(1-6C)carbonyl; amino alkyl(1-6C)carbonyl alkyl(1-6C); N-Z-amino alkyl(1-6C)carbonyl alkyl(1-6C ); N- alkyl(1-6C )amino alkyl(1-6C)carbonyl alkyl(1-6C); N,N-di alkyl(1-6C)amino alkyl(1-6C)carbonyl alkyl(1-6C); carboxy; alkyl(1-6C)carboxy; alkyl(1-6C )sulfonyl; aminosulfonyl; N-Z-aminosulfonyl; N- alkyl(1-6C)aminosulfonyl; N,N-di alkyl(1-6C )aminosulfonyl; aminosulfonyl alkyl(1-6C); N-Z-aminosulfonyl alkyl(1-6C); N- alkyl(1-6C)aminosulfonyl alkyl(1-6C); N,N-dialkyl(1-6C)aminosulfonyl alkyl(1-6C); carbamyl; N- alkyl(1-6C)carbamyl; N,N-di alkyl(1-6C)carbamyl; carbamylalkyl(1-6C ) etc.;  R<4> = 1-6C alkyl; monohydroxy1-6C alkyl; 2-6 C polyhydroxyalkyl; a group Z; 1-6C alkoxy, 1-6C alkyl aryl; benzyl; 1-6 C carboxyalkyl; 1-5C alkylcarboxyalkyl with 1-6 C; 1-6 C cyanoalkyl; 1-6 C carbamylalkyl; N-alkyl(1-6C)carbamyl alkyl with 1-6 C; N,N-dialkyl(1-6C)carbamylalkyl with 1-6 C; trifluoro alkyl(1-6C) etc.;  Z = unsaturated cationic group (III) or (IV) or a saturated cationic group of formula -D-(((R<9>)a)N<+)<R<8>)(R<6>)-R<7>)X<-> (V) D = bridging bond comprising an alkyl chain preferably of 1-14 C, linear or branched, optionally interrupted by heteroatom(s) such as O, N or S or substituted by one or more OH or 1-6 C alkoxy radicals; E, G, J, L, M = C, O, S or N;  n = 0-4;  m = 0-5;  R = covalent bond; Z; OH; 1-6 C alkyl; 1-6 C monohydroxyalkyl; 2-6 C polyhydroxyalkyl; nitro; cyano; 1-6 C cyanoalkyl; 1-6 C alkoxy; trialkyl(C1-C6)silanealkyl(C1-C6); amido; aldehydo; carboxyl; 1-6 C alkylcarbonyl; thio; 1-6 C thioalkyl; amino; amino radical protected by alkyl(C1-C6)carbonyl, carbamyl or alkyl(C1-C6)sulfonyl; NHR or NRR''' in which R and R''' (same or different) = 1-6 C alkyl, 1-6 C monohydroxyalkyl, or 2-6 C polyhydroxyalkyl; when in (III) or (IV) n or m is greater than 2, then two adjacent radicals R may together form an unsaturated 5- or 6-membered ring which may contain one or more heteroatoms;  R<5> = covalent bond; 1-6 C alkyl; 1-6 C monohydroxyalkyl; 2-6 C polyhydroxyalkyl; 1-6 C cyanoalkyl; trialkyl(C1-C6)silanealkyl(C1-C6); alkoxy(C1-C6)alkyl(C1-C6); carbamylalkyl(C1-C6); alkyl(C1-C6)carboxyalkyl(C1-C6); benzyl; or Z R<6>, R<7> and R<8> = covalent bond; 1-6 C alkyl; 1-6 C monohydroxyalkyl; 2-6 C polyhydroxyalkyl; alkoxy(C1-C6)alkyl(C1-C6); 1-6 C cyanoalkyl; aryl; benzyl; amidoalkyl(C1-C6); trialkyl(C1-C6)silanealkyl(C1-C6); aminoalkyl(C1-C6) in which the amine is protected by alkyl(C1-C6)carbonyl, carbamyl, or alkyl(C1-C6)sulfonyl; two of the radicals R<6>, R<7> and R<8> may, together with the N atoms form a saturated 5- or 6-membered ring which may contain one or more heteroatoms;  R<6>, R<7> and R<8> may also = a second group Z;  R<9> = 1-6 C alkyl; 1-6 C monohydroxyalkyl; 2-6 C polyhydroxyalkyl; aryl; benzyl; aminoalkyl(C1-C6); aminoalkyl(C1-C6) in which the amine is protected by an alkyl(C1-C6)carbonyl, carbamyl or alkyl(C1-C6)sulfonyl; carbamylalkyl(C1-C6); 1-6 C trifluoroalkyl; trialkyl(C1-C6)silanealkyl(C1-C6); sulfonamidoalkyl(C1-C6); alkyl(C1-C6)carboxyalkyl(C1-C6) etc.;  a and y = whole numbers 0 or 1 provided that in the groups (III), if a = 0, the bridging member D is attached to the N atom and if a = 1, the bridging member D is attached to one of E, G, J or L; y may not = 1 (1) if E, G, J and L all = C and if R<5> is carried by the N atom of the unsaturated ring, or (2) if at least one of E, G, J and L = N onto which R<5> is attached; in the groups (IV), if a = 0, the bridging member D is attached to the N atom and if a = 1, the bridging member D is attached to one of E, G, J, L or M; y may not = 1 (1) if at least one of E, G, J, L, and M = a divalent atom and the radical R<5> is carried by the N atoms of the unsaturated ring; and in the groups (V), if a = 0, the bridging group D is attached to the N atom carrying the radicals R<7> - R<8> and if a = 1, two of the radicals R<7> - R<8> together with the N form a saturated 5- or 6-membered ring as defined above and the bridging member D is attached to a C atom of the saturated ring;  X = a monovalent or divalent anion; provided that the number of cationic groups Z of formula (III), (IV) or (V) is at least one.