Black perylene pigments comprising fused-ring dipyridoperylenedione isomers useful for coloring high molecular weight organic material of natural and synthetic origin

摘要

Black perylene pigments (I) comprising fused-ring dipyridoperylenedione isomers and having a black number of at least 210 in an alkyd/melamine stoving lacquer are new. Black perylene pigments (I) comprising fused-ring dipyridoperylenedione isomers of formula (Ia) and/or (Ib) and having a black number of at least 210 in an alkyd/melamine stoving lacquer are new. [Image] [Image] R 1, R 2phenylene, naphthylene or pyridylene, all optionally substituted with 1-12C alkyl, 1-6C alkoxy, OH, NO 2 and/or halo; X : halo; n : 0-4. Independent claims are also included for: (1) producing the perylene pigments from synthetically produced crude pigments by either comminution and optionally recrystallization from a liquid medium or comminution and simultaneous recrystallization; (2) producing the crude pigments by condensing perylene-3,4;9,10-tetracarboxylic acid dianhydride with an aromatic ortho-diamine and cyclizing the product, where condensation and cyclization are effected in a reaction medium comprising phenol or a non-fused nitrogen-containing heteroaromatic compound; (3) pigment synergists comprising isomers of formula (Ia') or (Ib'). [Image] [Image] R 1', R 2' : phenylene, naphthylene or pyridylene, all substituted with COOM, COOR 3, CONR 3R 4, COO - N +R 3R 4R 5R 6, SO 2NR 3R 4, CH 2NR 3R 4, CH 2N +R 3R 4R 5R 6 R 3COO - and/or CH 2R 7 and optionally substituted with 1-12C alkyl, 1-6C alkoxy, OH, NO 2 and/or halo; R 3-R 6H; 1-12C alkyl or 2-12C alkenyl optionally interrupted by O, S, NR 8, CO or SO 2 and optionally substituted with OH, halo, aryl, 1-4C alkoxy and/or acetyl; or 3-8C cycloalkyl optionally interrupted by O, S, NR 8 or CO and optionally substituted with acetyl; R 7phthalimidyl; R 8H or 1-8C alkyl; M : H or metal; X : halo; n : 0-4.