Patent EP-0673978-A1 (EP)
Inventor: KRAPP MICHAEL DR
IPC: C09B29/01
Filed: 1995-03-15
Abstract: Isoindoline azo pigments of formula (I) are new. They maybe in the azo or hydrazo form or in the form of an equilibrium mixt of these forms and their lake-forming gps may be in lake form. A = =S, =C(R<1>)-CN or a gp of the formula. R<1> = CN; carbamoyl, opt substd by 4,6-dimethyl-1H-pyrazolo(3,4-b)-pyrid-3-yl or 3,3,5,5-tetramethyl-4-piperidyl, by 1-18C alkyl, 1-10C alkoxycarbonyl, benzyl, phenyl or naphthyl, in which the substits may be substd by halogen, CN, NO2, SO3H, 1-10C alkyl, 1-10C alkoxy, 1-10C alkylcarbonyl, 1-10C alkoxy-carbonyl, mono- or di-(1-10C alkyl)-amino, formyl amino, 2-10C alkanoylamino, benzoylamino, aminosulphonyl, mono- or di-(1-10C alkyl)-aminosulphonyl, phenyl-azo, 3,3,5,5,-tetramethyl-4-piperidyl, phthalimidyl, carbamoyl (opt mono- or di-substd by 1-10C alkyl) and/or CF3; 1-10C alkylcarbonyl, benzoyl, 1-10C alkoxycarbonyl, phenoxycarbonyl or benzyloxycarbonyl, in which benzoyl, phenoxy and benzyloxy may be substd by halogen, NO2, SO3H, 1-10C alkyl, formylamino, 2-10C alkanoylamino and/or phthalimidyl; phenyl, opt substd by halogen, CN, NO2, SO3H and/or CF3; carbazoyl or ureidocarbonyl, in which the terminal N atoms may be mono- or di-substd by 1-10C alkyl or benzyl, opt with the given substits; or a heterocyclic gp of the formulae. Z = -O-, -S- or -NH-; R<6> = halogen, NO2, SO3H, 1-6C alkyl or 1-6C alkoxy; R<7> = halogen; p = 0-2; q = 1-4; R<2> = H, 1-10C alkyl, phenyl or naphthyl, opt substd by halogen, NO2, SO3H, 1-10C alkyl and/or 1-10C alkoxy; R<3> = 1-10C alkyl, amino, benzoylamino, COOH, carbamoyl or 1-10C alkoxycarbonyl; R<4> = H or phenyl with up to 2 substits selected from halogen, NO2, SO3H, COOH, carbamoyl, 1-10C alkoxy, 1-10C alkoxy or 1-10C alkoxycarbonyl; R<5> = halogen or NO2; X = -O- or -NR<8>- (R<8>= H or 1-10C alkyl); m = 0-4; L = 1,4- or 1,3-phenylene or 1,5-naphthylene, opt substd by halogen, NO2, COOH, SO3H, sulphonamido (opt mono- or di-substd by 1-10C alkyl), 1-10C alkyl, 1-10C alkoxy, 1-10C alkylcarbonyl, 1-10C alkoxycarbnyl, formylamino, 210C alkanoylamino and/or carbamoyl (opt mono- or di-substd by 1-10C alkyl); K = the radical of a coupling component of the formula. R<8> = H, halogen, NO2, SO3H, 1-10C alkyl, 1-10C alkoxy, 1-10C alkoxycarbonyl and/or carbamoyl (opt mono- or di-substd by 1-10C alkyl); R<9> = 1-10C alkyl, opt substd by amino or mono- or di-(1-10C alkylamino; R<10> = H, halogen, CN, SO3H, 1-10C alkylcarbonyl, 110C alkoxycarbonyl or carbamoyl (opt mono- or di-substd by 1-10C alkyl); R<11> = methyl or phenyl, opt substd by halogen, OH, NO2, SO3H, 1-10C alkyl, 1-10C alkoxy, 1-10C alkylcarbonyl, 1-10C alkoxycarbonyl, formylamino, 2-10C alkanoylamino, COOH, carbamoyl (opt mono- or di-substd by 1-10C alkyl) mono- or di-(1-10C alkyl)- or -(phenyl)-aminosulphonyl and/or 1-10C alkoxy- or phenoxysulphonyl; R<12> = H, halogen, OH, SO3H, 1-10C alkyl, 1-10C alkoxy, 1-10C alkylcarbonyl, carbamoyl (opt mono- or di-substd by 1-10C alkyl) and/or mono-(1-10C alkyl)- or -(phenyl)-aminosulphonyl; R<13> = 1-10C alkyl or 1-10C alkylcarbonyl; R<14> =OH or -NH-R<20>; R<20> = H, phenyl (opt with the substits given for phenyl in R<10>) or a heterocyclic gp of the formulae. R<15> = phenyl or naphthyl, opt with the substits given for phenyl in R<10>; R<16> = Me or -NH-R<15>; R<17> = H or SO3H; R<18> = H or OH; R<19> = halogen; Y = -O- or -CH)2-; Z = =O or =S; benzene ring D may be substd by halogen, NO2, COOH, carbamoyl, 1-10C alkyl and/or 1-10C alkoxy.