Preparation and purification of perylene-3,4-dicarbimides

Claim 2

A process for preparing perylene-3,4-dicarbimides by reacting a perylene-3,4,9,10-tetracarboxylic acid or the corresponding anhydrides with a primary amine, which comprises performing the reaction in a reaction medium consisting essentially of a tertiary nitrogen base as solvent and of a transition metal or transition metal salt as catalyst.

Claim 3

A process as claimed in claim 1, wherein the tertiary nitrogen base used is a nitrogen-containing heteroaromatic.

Claim 4

A process as claimed in claim 1, wherein the catalyst used is zinc, a zinc salt, copper, a copper salt or a mixture thereof.

Claim 5

A process for purifying perylene-3,4-dicarbimides obtained by reaction of a perylene-3,4,9,10-tetracarboxylic acid or of the corresponding anhydrides with a primary amine, which comprises first heating the crude products in N-methylpyrrolidone, then treating the resulting N-methylpyrrolidone adducts with a base in the presence of an organic diluent, and, if desired, subjecting the subsequently isolated products to an additional treatment with an aqueous acid.

Claim 6

A process for purifying perylene-3,4-dicarbimides obtained by reaction of a perylene-3,4,9,10-tetracarboxylic acid or of the corresponding anhydrides with a primary amine, which comprises first heating the crude products in N-methylpyrrolidone, then treating the resulting N-methylpyrrolidone adducts with a base in the presence of an organic diluent, and, if desired, subjecting the subsequently isolated products to an additional treatment with an aqueous acid.

Claim 7

A process as claimed in claim 4, wherein the base used is an alkali metal hydroxide or an alkali metal alkoxide.

Claim 8

A process for making pure perylene-3,4-dicarbimides by reacting a perylene-3,4,9,10-tetracarboxylic acid or the corresponding anhydrides with a primary amine, which comprises performing the reaction in the presence of a tertiary nitrogen base as solvent and of a transition metal or transition metal salt as catalyst and first heating the resulting crude products in N-methylpyrrolidone, then treating the resulting N-methylpyrrolidone adducts with a base in the presence of an organic diluent, and, if desired, subjecting the subsequently isolated products to an additional treatment with an aqueous acid.

Claim 9

A process for making pure perylene-3,4-dicarbimides by reacting a perylene-3,4,9,10-tetracarboxylic acid or the corresponding anhydrides with a primary amine, which comprises performing the reaction in the presence of a tertiary nitrogen base as solvent and of a transition metal or transition metal salt as catalyst and first heating the resulting crude products in N-methylpyrrolidone, then treating the resulting N-methylpyrrolidone adducts with a base in the presence of an organic diluent, and, if desired, subjecting the subsequently isolated products to an additional treatment with an aqueous acid.

Claim 10

Perylene-3,4-dicarbimides of the general formula Ia ##STR12## where R 1' is C 14 -C 30 -alkyl whose carbon chain may be interrupted by one or more of --O--, --S--, --NR 3 --, --CO-- and/or --SO 2 -- and which is monosubstituted or polysubstituted by carboxyl, sulfo, hydroxyl, cyano, C 1 -C 6 -alkoxy or a 5-, 6- or 7-membered heterocyclic radical which is attached via a nitrogen atom and which may contain further heteroatoms and may be aromatic, where R 3 is hydrogen or C 1 -C 6 -alkyl; or R 1' is C 5 -C 8 -cycloalkyl whose carbon skeleton is interrupted by one or more of --O--, --S--, and/or --NR 3 --; or R 1' is phenyl which is polysubstituted by C 1 -C 4 -alkyl or methoxy at least in the two ortho positions, and/or monosubstituted or polysubstituted by C 5 -C 18 -alkyl, C 2 -C 6 -alkoxy, halogen, hydroxyl, cyano, carboxyl, --CONHR 4 , --NHCOR 4 and/or aryl- or hetaryl-azo, which may each be substituted by C 1 -C 10 -alkyl, C 1 -C 6 -alkoxy, halogen, hydroxyl, cyano or carboxyl, where R 3 is as above defined, and R 4 is hydrogen, C 1 -C 18 -alkyl, aryl or hetaryl, wherein the aryl or hetaryl may each be substituted by C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, halogen, hydroxyl or cyano, or R 1' is naphthyl or hetaryl, which may each be substituted by a radical defined as substituents for phenyl, in which case the C 1 -C 4 -alkyl and C 1 -C 6 -alkoxy substituents may be in any desired position on the ring system; R 2 is in each instance independently of the other instances hydrogen; halogen; C 1 -C 18 -alkyl; aryloxy, arylthio, hetaryloxy or hetarylthio, which may each be substituted by C 1 -C 10 -alkyl, C 1 -C 6 -alkoxy, cyano or carboxyl.

Claim 11

Perylene-3,4-dicarbimides of the general formula Ia ##STR12## where R 1' is C 14 -C 30 -alkyl whose carbon chain may be interrupted by one or more of --O--, --S--, --NR 3 --, --CO-- and/or --SO 2 -- and which is monosubstituted or polysubstituted by carboxyl, sulfo, hydroxyl, cyano, C 1 -C 6 -alkoxy or a 5-, 6- or 7-membered heterocyclic radical which is attached via a nitrogen atom and which may contain further heteroatoms and may be aromatic, where R 3 is hydrogen or C 1 -C 6 -alkyl; or R 1' is C 5 -C 8 -cycloalkyl whose carbon skeleton is interrupted by one or more of --O--, --S--, and/or --NR 3 --; or R 1' is phenyl which is polysubstituted by C 1 -C 4 -alkyl or methoxy at least in the two ortho positions, and/or monosubstituted or polysubstituted by C 5 -C 18 -alkyl, C 2 -C 6 -alkoxy, halogen, hydroxyl, cyano, carboxyl, --CONHR 4 , --NHCOR 4 and/or aryl- or hetaryl-azo, which may each be substituted by C 1 -C 10 -alkyl, C 1 -C 6 -alkoxy, halogen, hydroxyl, cyano or carboxyl, where R 3 is as above defined, and R 4 is hydrogen, C 1 -C 18 -alkyl, aryl or hetaryl, wherein the aryl or hetaryl may each be substituted by C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, halogen, hydroxyl or cyano, or R 1' is naphthyl or hetaryl, which may each be substituted by a radical defined as substituents for phenyl, in which case the C 1 -C 4 -alkyl and C 1 -C 6 -alkoxy substituents may be in any desired position on the ring system; R 2 is in each instance independently of the other instances hydrogen; halogen; C 1 -C 18 -alkyl; aryloxy, arylthio, hetaryloxy or hetarylthio, which may each be substituted by C 1 -C 10 -alkyl, C 1 -C 6 -alkoxy, cyano or carboxyl.

Claim 12

Perylene-3,4-dicarbimides as claimed in claim 7 of the formula Ia where R 1' is C 14 -C 30 -alkyl which is monosubstituted by carboxyl, sulfo, hydroxyl or a 5-, 6- or 7-membered heterocyclic radical which is attached via a nitrogen atom and which may contain further heteroatoms and may be aromatic; phenyl which is polysubstituted by C 1 -C 4 -alkyl at least in the two ortho positions, or monosubstituted or polysubstituted by halogen, hydroxyl, cyano, carboxyl, --COHNR 4 or --NHCOR 4 and/or monosubstituted by aryl- or hetaryl-azo, which may each be substituted by C 1 -C 10 -alkyl, C 1 -C 6 -alkoxy, halogen, hydroxyl, cyano or carboxyl; hetaryl which may be substituted by the radicals defined as above substituents for phenyl and/or by C 1 -C 4 -alkoxy, in which case the C 1 -C 4 -alkyl substituents may be in any desired position on the ring system; R 2 is in each instance independently of the other instances hydrogen, halogen or phenoxy which may be substituted by C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, cyano or carboxyl.

Claim 13

Perylene-3,4-dicarbimides as claimed in claim 7 of the formula Ia where R 1' is C 14 -C 30 -alkyl which is monosubstituted by carboxyl, sulfo or hydroxyl; phenyl which is substituted by C 1 -C 4 -alkyl in both ortho positions, hydroxyl, cyano, carboxyl, --CONHR 4 or --NHCOR 4 , where R 4 is C 1 -C 4 -alkyl or phenyl which may be substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or cyano, or by phenyl- or naphthyl-azo which may be substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, hydroxyl or cyano; monocyclic hetaryl which may be monosubstituted or polysubstituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, hydroxyl or cyano or monosubstituted by phenyl- or naphthyl-azo which may be substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, hydroxyl or cyano; R 2 is in each instance independently of the other instances hydrogen or phenoxy which may be substituted by C 1 -C 4 -alkyl.

Claim 14

A method of coloring comprising contacting the perylene-3,4-dicarbimides of the formula Ia as set forth in claim 7 with an organic or organic/inorganic composite material.