Preparation of Pigment Red 149
AssigneeBASF SE
InventorsHeinrich Kowarsch, Josef Hetzenegger, Andreas Stohr, Hans-Joachim Uschmann
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Abstract
The invention provides a process for preparing N,N′-di(3′,5′-dimethylphenyl)perylene bis(dicarboximide), and other pigments having modified properties, by reaction of perylene-3,4,9,10-tetracarboxylic dianhydride with 3,5-dimethylaniline, or a mixture of 3,5-dimethyl aniline and at least one other primary amine, in the presence of a secondary amine or tertiary amine as catalyst, wherein the reaction occurs in an aqueous reaction medium and in the presence of added seed crystals of N,N′-di(3′,5′-dimethylphenyl) perylenebis(dicarboximide), such that the aqueous medium is present at the beginning of the reaction.
Claims14
A process for preparing N,N′-di(3′,5′-dimethyl phenyl)perylenebis(dicarboximide), the process comprising reacting perylene-3,4,9,10-tetra carboxylic dianhydride with 3,5-dimethylaniline in the presence of a secondary amine as catalyst, wherein:
- a molar ratio between the 3,5-dimethylaniline and the perylene-3,4,9,10-tetracarboxylic dianhydride ranges from 2:1 to 3:1;
- the reaction occurs in an aqueous reaction medium and in the presence of added seed crystals of N,N′-di(3′,5′-dimethylphenyl) perylenebis(dicarboximide), wherein the seed crystals are present prior to the beginning of the reaction;
- the aqueous reaction medium is present at the beginning of the reaction;
- the reaction occurs at a temperature in the range from 130° C. to 170° C. and at a pressure in the range from 2 bar to 13 bar;
- and
- the process provides Pigment Red 149 in the alpha form, such that the Pigment Red 149 comprises less than 5% by weight of a monoimide by-product.
A process for preparing a perylenebis(dicarboximide), the process comprising reacting perylene-3,4,9,10-tetracarboxylic dianhydride with a primary amine mixture in the presence of a secondary amine as catalyst, wherein the reaction occurs in an aqueous reaction medium and in the presence of added seed crystals of N,N′-di(3′,5′-dimethylphenyl) perylenebis-(dicarboximide), wherein the seed crystals are present prior to the beginning of the reaction,
- wherein:
- the aqueous reaction medium is present at the beginning of the reaction;
- the primary amine mixture comprises 3,5-dimethylaniline and 0% to 10% by weight of a primary amine, based on a total weight of the primary amine mixture;
- the reaction occurs at a temperature in the range from 130° C. to 170° C. and at a pressure in the range from 2 bar to 13 bar;
- and
- a molar ratio between the 3,5-dimethylaniline and the perylene-3,4,9,10-tetracarboxylic dianhydride ranges from 2:1 to 3:1.
A process for preparing a perylenebis(dicarboximide), the process comprising reacting perylene-3,4,9,10-tetracarboxylic dianhydride with a primary amine mixture in the presence of a tertiary amine, wherein:
- the reaction occurs in an aqueous reaction medium and in the presence of added seed crystals of N,N′-di(3′,5′-dimethylphenyl) perylenebis(dicarboximide), wherein the seed crystals are present prior to the beginning of the reaction;
- the aqueous reaction medium is present at the beginning of the reaction;
- the primary amine mixture comprises 3,5-dimethylaniline and 0% to 10% by weight of a primary amine, based on a total weight of the primary amine mixture;
- the reaction occurs at a temperature in the range from 130° C. to 170° C. and at a pressure in the range from 2 bar to 13 bar;
- and
- a molar ratio between the 3,5-dimethylaniline and the perylene-3,4,9,10-tetracarboxylic dianhydride ranges from 2:1 to 3:1.
Dependencies are inferred from the claim text.