Process for the preparation of arylimides of perylene-3,4,9,10-tetracarboxylic acid

Claim 1

A method for catalyzing the condensation of perylene-3, 4, 9, 10-tetracarboxylic dianhydride or a perylene-3, 4, 9, 10-tetracarboxylic monoanhydride of the formula (2) ##STR23## in which R 2 denotes a hydrogen atom or a C 1 -C 8 alkyl or phenyl or naphthyl group, which can be substituted on the aromatic nucleus by an alkyl, cycloalkyl, alkoxy, aryloxy, arylazo or nitro group or halogen atom, with a primary arylamine of the formula R 1 --NH 2 , wherein R 1 denotes a phenyl or Naphthyl group which can be substituted on the aromatic nucleus by an alkyl, cycloalkyl, alkoxy, aryloxy, arylazo or nitro group or a halogen atom, to obtain an arylamide of a perylene-3, 4, 9, 10-tetracarboxylic acid, of the formula (1): ##STR24## wherein, if both R 1 and R 2 are aryl groups, R 1 and R 2 can be either identical or different; wherein, the condensation reaction is conducted in the presence of a catalyst system consisting essentially of 0.05 to 5 mole, per mole of perylene-3, 4, 9, 10-tetracarboxylic dianhydride or per mole of the monoanhydride of formula (2), of a dialkylamine of the formula (4) ##STR25## in which R' and R" denote identical or different straight-chain C 1 -C 6 alkyl or branched C 3 -C 6 alkyl or C 5 -C 6 cycloalkyl groups, which can be substituted by hydroxyl, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, or phenyl or naphthyl groups, said phenyl or naphthyl groups being unsubstituted or substituted on the aromatic nucleus by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, or C 1 -C 4 alkylamino groups or halogen atoms, and in which the R' and R" can form, together with the nitrogen atom, piperidine, piperazine, morpholine, or pyrrolidine which can be unsubstituted or substituted by a lower alkyl or a phenyl group, the condensation being carried out with continuous removal fo the water of reaction and substantially in the absence of water as an inert diluent.

Claim 2

A method for catalyzing the condensation of perylene-3, 4, 9, 10-tetracarboxylic dianhydride or a perylene-3, 4, 9, 10-tetracarboxylic monoanhydride of the formula (2) ##STR23## in which R 2 denotes a hydrogen atom or a C 1 -C 8 alkyl or phenyl or naphthyl group, which can be substituted on the aromatic nucleus by an alkyl, cycloalkyl, alkoxy, aryloxy, arylazo or nitro group or halogen atom, with a primary arylamine of the formula R 1 --NH 2 , wherein R 1 denotes a phenyl or Naphthyl group which can be substituted on the aromatic nucleus by an alkyl, cycloalkyl, alkoxy, aryloxy, arylazo or nitro group or a halogen atom, to obtain an arylamide of a perylene-3, 4, 9, 10-tetracarboxylic acid, of the formula (1): ##STR24## wherein, if both R 1 and R 2 are aryl groups, R 1 and R 2 can be either identical or different; wherein, the condensation reaction is conducted in the presence of a catalyst system consisting essentially of 0.05 to 5 mole, per mole of perylene-3, 4, 9, 10-tetracarboxylic dianhydride or per mole of the monoanhydride of formula (2), of a dialkylamine of the formula (4) ##STR25## in which R' and R" denote identical or different straight-chain C 1 -C 6 alkyl or branched C 3 -C 6 alkyl or C 5 -C 6 cycloalkyl groups, which can be substituted by hydroxyl, C 1 -C 4 alkoxy, C 1 -C 4 alkyl, or phenyl or naphthyl groups, said phenyl or naphthyl groups being unsubstituted or substituted on the aromatic nucleus by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, or C 1 -C 4 alkylamino groups or halogen atoms, and in which the R' and R" can form, together with the nitrogen atom, piperidine, piperazine, morpholine, or pyrrolidine which can be unsubstituted or substituted by a lower alkyl or a phenyl group, the condensation being carried out with continuous removal fo the water of reaction and substantially in the absence of water as an inert diluent.