GB1488924A - Disperse bisanil dyes derived from diaminomaleonitrile and their preparation - Google Patents

Abstract

1488924 Bisanil dyes E I DU PONT DE NEMOURS & CO 2 Jan 1975 [3 Jan 1974 (3)] 57/75 Heading C4P Novel bisanil dyes have the formula wherein each of Ar 1 and Ar 2 is independently selected from (1) benzo(5- and 6-membered)- heterocyclic groups containing 0-4 methyl substituents and (2) phenyl, naphthyl, 5- membered heterocyclic and 6-membered heterocyclic groups containing 0-3 substituents selected from NO 2 , halogen, CN, C 1-4 alkyl, C 1-4 alkoxy, OCH 2 -phenyl, phenyl, CF 3 , OH, OC 1-4 alkylene-N(C 1-4 alkyl) 2 , C 2-4 alkylene-Cl, NHCONH 2 , NHCOA, NHSO 2 A, SR 8 , SO 2 R 8 , NHR 1 , NHCOC 1-4 alkylene-B and -NR 1 R 2 wherein; (a) R 1 is C 1-4 alkyl or C 2-4 alkylene-R 3 ; (b) R 2 is C 1-4 alkyl, C 2-4 alkylene-R 4 or, if Ar 1 or Ar 2 is phenyl, C 3 alkylene attached to a phenyl position which is ortho to the position to which the nitrogen is attached; (c) R 3 is CN, halogen, OH, phenyl, C 1-4 alkoxy, OC 1-4 alkylene-CN, CO 2 A, OCOA, OCONHA or CO 2 C 1-4 alkylene-OCOA; (d) R 4 is CN, halogen, OH, phenyl, OC 1-4 alkylene-CN, CO 2 A, OCOA, CO 2 C 1-4 alkylene- OCOA, SO 2 A, phthalimido, succinimido, glutarimido, OCOCH=CH 2 , CH 2 -CH(OCOA)CH 2 OA or CH 2 CH(OCONHA)CH 2 OA; (e) A is C 1-4 alkyl or R 5 ; (f) B is halogen, C 1-4 alkoxy or R 5 ; (g) R 5 is phenyl containing 0-2 substituents selected from C 1-4 alkyl, C 1-4 alkoxy, halogen, NO 2 , CN, C 1-4 alkyl-CONH and NR 6 R 7 wherein each of R 6 and R 7 is independently selected from H and C 1-4 alkyl, with at least one of R 6 and R 7 being C 1-4 alkyl; and (h) R 8 is C 1-4 alkyl, C 2 H 4 OH, C 5-6 cycloalkyl or R 5 . The dyes are prepared by condensation of diaminomaleonitrile with an aromatic aldehyde to a monoanil, reduction of this, further condensation with an aromatic aldehyde, and finally oxidation of the monoanil to the bisanil. The dyes give fluorescent yellow to blue dyeings on polyester fibres either alone or in cellulosic (e.g. cotton) blends.