Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From carboxylic acid or derivative thereof
Patent
1995-08-29
1997-10-14
Seidleck, James J.
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From carboxylic acid or derivative thereof
528315, 146 37, C08G 6908, C08G 7310
Patent
active
056774176
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP 94/01345 filed Apr. 28, 1994.
BACKGROUND OF THE INVENTION
Field of the Invention
The present invention relates to novel tetraaroxypery-lene-3,4,9,10-tetracarboxylic polyimides of the formula I ##STR2## where R.sup.1 : denotes identical or different aryl radicals which may be substituted by cyano, nitro, halogen, C.sub.1 -C.sub.18 -alkoxy, C.sub.5 -C.sub.7 -cycloalkyl and/or C.sub.1 -C.sub.18 -alkyl and may each contain up to 24 carbon atoms; be interrupted by from 1 to 10 oxygen atoms in ether function or by a phenylene or cyclohexylene group, or optionally C.sub.1 -C.sub.10 -alkylene- or oxygen-bridged C.sub.6 -C.sub.30 -arylene or cyclohexylene radicals; light collectors, printing inks and paints and for coloring plastics.
The invention also relates to the use of novel tetraaroxypery-lene-3,4,9,10-tetracarboxylic dianhydrides of the formula III ##STR3## and to the corresponding tetraaroxyperylene-3,4,9,10-tetracarboxylic acids (IIa) as intermediates for preparing the polyimides I.
As will be known, there are many possible uses for fluorescent dyes; they are used for example for the flat-plate concentration of light in light collectors, for manufacturing dye lasers and daylight-fluorescent colors and also generally for coloring printing inks, paints and polymers.
For this the dyes have to have a number of properties which are high in particular for light collectors. They have to have high fluorescence, a broad absorption range, good separation of absorption and emission bands in the application medium, high lightfastness and good solubility and at the same time low tendency to migrate in the application medium.
DESCRIPTION OF THE RELATED ART
These requirements are difficult to meet at one and the same time. This is also true of the fluorescent dyes described in EP-A-227 980 and JP-A-53 894/1992, which are based on monomeric, tetrasubstituted perylene-3,4,9,10-tetracarboxylic diimides and which are in some instances not satisfactory as regards their migration resistance.
JP-A-110 219/1988 and EP-A-445 577 disclose unsubstituted perylene-3,4,9,10-tetracarboxylic polyimides which, however, are not used as fluorescent dyes.
It is an object of the present invention to provide fluorescent dyes which come particularly close to the required property profile.
SUMMARY OF THE INVENTION
We have found that this object is achieved by the above-defined tetraaroxyperylene-3,4,9,10-tetracarboxylic polyimides I.
The invention further provides a process for preparing the polyimides I, which comprises formula II ##STR4## where the radicals R.sup.3 are C.sub.1 -C.sub.30 -alkyl radicals whose carbon chain may be interrupted by from 1 to 10 oxygen atoms in ether function, C.sub.5 -C.sub.7 -cycloalkyl or phenyl radicals which may each be substituted by up to 2 C.sub.1 -C.sub.4 -alkyl groups, with a base in a polar, protic solvent, and dianhydride obtained in step a), of the general formula III ##STR5## with a diamine of the general formula IV basic catalysis at from 170.degree. to 200.degree. C.
The invention also provides for the use of the polyimides I for manufacturing dye lasers and light collectors and for pigmenting printing inks, paints and plastics.
Lastly the present invention provides the tetraaroxyperylene-3,4,9,10-tetracarboxylic dianhydrides III and their corresponding tetraaroxyperylene- 3,4,9,10-tetracarboxylic acids (IIIa) as intermediates for preparing the polyimides I.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
R.sup.1 is aryl, such as naphthyl, anthryl or in particular phenyl. The aryl radicals can be substituted by cyano, nitro, halogen, in particular chlorine, C.sub.1 -C.sub.18 -alkoxy, C.sub.5 -C.sub.7 -cycloalkyl, especially cyclohexyl, and/or C.sub.1 -C.sub.18 -alkyl, and in each case can contain up to 24 carbon atoms. The R.sup.1 radicals can be identical or different, but are preferably identical.
Examples of the C.sub.1 -C.sub.18 -alkoxy and alkyl groups suitable for use as substituents are: tert-butoxy, pentyloxy, isopentyloxy, neo-pentyloxy, hexyloxy,
REFERENCES:
patent: 4845223 (1989-07-01), Seybold et al.
Japanese Abst. 58 894/1992.
Japanese Abst. 110 219/1988.
Dotcheva Dobrinka Todorova
Klapper Markus
Muellen Klaus
Max-Planck-Gesellschaft zur Foerderung
Seidleck James J.
Truong Duc
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