1,7-disubstituted perylene-3,4,9, 10-tetracarboxylic acids, thei

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549232, 25230117, 25230132, C09B 314, C07D49306

Patent

active

060631813

DESCRIPTION:

BRIEF SUMMARY
BACKGROUND OF THE INVENTION

1. Field of the Invention
The present invention relates to 1,7-disubstituted perylene-3,4,9,10-tetracarboxylic dianhydrides. perylene-3,4,9,10-tetracarboxylic dianhydrides of the general formula I and perylene-3,4,9,10-tetracarboxylic acids of the general formula Ia ##STR2## where L.sup.1 and L.sup.2 independently of one another are 1,2-ethylene, 1,2-ethenylene and 1,2-ethynylene; -C.sub.30 -alkyl, whose carbon chain can be interrupted by one or more groups --O--, --S--, --NR.sup.3 -, --CO-- and/or --SO.sub.2 -- and/or which can be substituted one or more times by --COOR.sup.3, --SO.sub.3 R.sup.3, hydroxyl, cyano, C.sub.1 -C.sub.6 -alkoxy, C.sub.5 -C.sub.8 -cycloalkyl or aryl or by a 5- to 7-membered heterocyclic radical which is attached via a nitrogen atom and can include further heteroatoms and/or can be aromatic, R.sup.3 being hydrogen or C.sub.1 -C.sub.6 -alkyl, dianhydrides (I) or the acids (1a) and to their use as pigments, laser dyes and precursors for preparing fluorescent dyes, polymeric colorants, pigments and pigment additives.
The invention additionally relates to novel 1,7-disubstituted perylene-3,4,9,10-tetracarboxylic diimides of the general formula VI ##STR3## where X.sup.1 is bromine or is --L--R, where interrupted by one or more groups --O--, --S--, --NR.sup.3 --, --CO-- and/or --SO.sub.2 -- and/or which can be substituted one or more times by --COOR.sup.3, --SO.sub.3 R.sup.3, hydroxyl, cyano, C.sub.1 -C.sub.6 -alkoxy, C.sub.5 -C.sub.8 -cycloalkyl or aryl or by a 5- to 7-membered heterocyclic radical which is attached via a nitrogen atom and can include further heteroatoms and/or can be aromatic, R.sup.3 being hydrogen or C.sub.1 -C.sub.6 -alkyl; by one or more groups --O--, --S-- or --CO--, or is C.sub.5 -C.sub.8 -cycloalkyl or aryl which can be substituted one or more times by C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -alkoxy, or the acids (Ia), and to a process for preparing the perylene-3,4,9,10-tetracarboxylic diimides (VI).
Perylene-3,4,9,10-tetracarboxylic acids and their anhydrides are known to be important intermediates for preparing perylimide pigments and perylimide dyes, but are also useful themselves for coloring or pigmenting high molecular mass organic materials.
In addition to unsubstituted perylene-3,4,9,10-tetracarboxylic acid, which can be obtained by hydrolyzing perylene-3,4,9,10-tetracarboxylic diimide in concentrated sulfuric acid at about 200.degree. C., there is particular interest in perylene-tetracarboxylic acids which are substituted in the perylene skeleton and whose properties in use, such as solubility, inherent color and fluorescence, can be tailored by introducing suitable substituents.
WO-A-94/255 discloses 1,6,7,12-tetraaroxy-substituted perylene-3,4,9,10-tetracarboxylic dianhydrides prepared by alkaline hydrolysis of the corresponding diimides in a polar protic solvent. The tetraaroxy-substituted diimides themselves are obtained by reacting the tetrachlorinated diimides with arylates (EP-A-227 980).
1,7-disubstituted perylene-3,4,9,10-tetracarboxylic acids, such as the novel compounds (Ia) which, like all perylene-3,4,9,10-tetracarboxylic acids, are generally in the form of the dianhydrides, have not been disclosed to date. In addition, the dihalogenated perylene-3,4,9,10-tetracarboxylic diimides described in EP-A-39 912 and in DE-A-412 122 are always mixtures of products with differing degrees of halogenation (especially tetra-, tri- and monohalogenated products); it has not been possible to prepare the dihalogenated diimides specifically.
It is therefore an object of the invention to provide novel 1,7-disubstituted perylene-3,4,9,10-tetracarboxylic acids and dianhydrides.
We have found that this object is achieved by the 1,7-disubstituted perylene-3,4,9,10-tetracarboxylic dianhydrides and the corresponding acids of the above-defined formulae I and Ia (referred to below as dianhydrides I), which may be substituted symmetrically or asymmetrically.
Preferred dianhydrides I are the subject of the subclaim.
We have also disco

REFERENCES:
patent: 5677417 (1997-10-01), Muellen et al.

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