Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1998-06-18
2000-11-07
Aulakh, C. S.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
562405, 562467, 562480, 562488, C07D49306, C07C 6348
Patent
active
061439053
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel, 1,7-disubstituted 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 R is aryloxy, arylthio, hetaryloxy or hetarylthio each of which can be substituted one or more times by C.sub.1 -C.sub.30 -alkyl whose carbon chain can be interrupted by one or more groups --O--, --S--, --NR.sup.1 --, --CO-- and/or --SO.sub.2 -- and/or can be substituted one or more times by --COOR.sup.1, --SO.sub.3 R.sup.1, hydroxyl, cyano, C.sub.1 -C.sub.6 -alkoxy, C.sub.5 -C.sub.8 -cycloalkyl or a 5- to 7-membered heterocyclic radical which is attached via nitrogen and can contain further heteroatoms, or can be substituted one or more times by C.sub.1 -C.sub.6 -alkoxy, cyano, --COOR.sup.1 or --SO.sub.3 R.sup.1, where R.sup.1 is hydrogen or C.sub.1 -C.sub.6 -alkyl perylene-3,4,9,10-tetracarboxylic dianhydrides (I) or of the acids (Ia) 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
In addition to unsubstituted perylene-3,4,9,10-tetracarboxylic acid, which can be obtained by hydrolyzing perylene-3,4,9,10-tetracarboxylic dimide 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-94/25504 discloses 1,6,7,12-tetraaroxy-substituted perylene-3,4,9,10-tetracarboxylic dianhydrides prepared by hydrolyzing the corresponding diimides under alkaline conditions in a polar protic solvent. The tetraaroxy-substituted diimides themselves have been 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. Even the dihalogenated perylene-3,4,9,10-tetracarboxylic diimides described in EP-A-39 912 and DRP 412 122 are always mixtures of products with different degrees of halogenation (especially tetra-, tri- and monohalogenated products); it was not possible to prepare specifically the dihalogenated diimides.
It is an object of the invention to provide novel, 1,7-diaroxy- and 1,7-arylthio-substituted 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 formulae I and Ia defined at the outset (referred to below as dianhydrides I).
Preferred dianhydrides I are the subject of the subclaim.
The object has additionally been achieved by a process for the preparation of the dianhydrides I, which comprises or 1,7-dibromoperylene-3,4,9,10-tetracarboxylic acid (IIa), in the presence of a polar aprotic solvent and in the presence or absence of an imidation catalyst, with a primary amine of the general formula III in which R.sup.2 is C.sub.4 -C.sub.30 -alkyl whose carbon chain can be interrupted 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, formed in step a), of the general formula IV ##STR3## in the presence of an inert aprotic solvent and of a non-nucleophilic or only weakly nucleophilic base with an aromatic alcohol or thioalcohol of the general formula V diimides, formed in step b), of the general formula VI ##STR4## in the presence of a polar protic solvent and a base to give the dianhydrides I.
In addition we have discovered the 1,7-disubstituted perylene-3,4,9,10-tetracarboxylic diimides of the formula VI defined a
REFERENCES:
patent: 5677417 (1997-10-01), Muellen et al.
Arms Harald
Blaschka Peter
Bohm Arno
Henning Georg
Aulakh C. S.
BASF - Aktiengesellschaft
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