Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1997-07-21
1999-11-16
Rotman, Alan L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
546 40, 8636, 8648, C09B 562, C07D22118
Patent
active
059860995
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel quaterrylenetetracarboxylic diimides of the general formula I ##STR2## where R is hydrogen; more of --O--, --S--, --NR.sup.1 --, --CO-- and/or --SO.sub.2 -- and which may be monosubstituted or polysubstituted by cyano, C.sub.1 -C.sub.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 one or more of --O--, --S-- and/or --NR.sup.1 --; C.sub.1 -C.sub.18 -alkyl, C.sub.1 -C.sub.6 -alkoxy, cyano, --CONHR.sup.2, --NHCOR.sup.2 and/or aryl- or hetaryl-azo, which may each be substituted by C.sub.1 -C.sub.10 -alkyl, C.sub.1 -C.sub.6 -alkoxy or halogen, where hetaryloxy or hetarylthio, which may each be substituted by C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy; hetarylthio, which may each be substituted by C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy;
The invention also relates to the preparation of these quaterrylenetetracarboxylic diimides and to their use as fluorescent dyes or pigments.
Lastly the invention relates to novel 9-haloperylene-3,4-dicarbimides of the general formula III ##STR3## where R and X are each as defined above, Hal is halogen and q is from 2 to 4, as intermediates for the quaterrylenetetracarboxylic diimides I.
EP-A-596 292 describes with reference to N,N'-didodecylquaterrylene-3,4:13,14-tetracarboxylic diimides the preparation of unsubstituted quaterrylenetetracarboxylic diimides (formula I: n=0; R=n-C.sub.12 H.sub.25) and their suitability for use as fluorescent dyes and pigments.
Starting from N-dodecylperylene-3,4,9,10-tetracarboxylic 3,4-imide 9,10-anhydride, decarboxylation in potassium hydroxide solution under superatmospheric pressure and at elevated temperature gives N-dodecylperylene-3,4-dicarbimide, which is brominated to N-dodecyl-9-bromoperylene-3,4-dicarbimide. This is converted by elimination of bromine in the presence of an inert diluent and of an organometallic catalyst to the corresponding biperylene derivative, where it is finally converted by heating in an alkali medium in the presence of an oxidizing agent into the abovementioned quaterrylene derivative.
However, EP-A-596 292 does not disclose any way of preparing substituted quaterrylenetetracarboxylic diimides I (hereinafter shortened to "quaterrylimides") which, however, are of special interest, since specific substitution makes it possible for the application properties (eg. solubility, hydrophilicity, lipophilicity, absorption and emission characteristics) to be predetermined and varied.
It is an object of the present invention to provide novel, substituted quaterrylimides which shall have advantageous application properties (including in the case of fluorescent dyes for example good solubility in the application media) and hence to provide means for optimum adaptation to the particular intended use.
We have found that this object is achieved by the quaterrylimides of the above-defined formula I.
Preferred quaterrylimides I are revealed in the subclaims.
We have also found various processes for preparing the quaterrylimides I, which are likewise revealed in the claims.
Finally, the present invention provides for the use of the quaterrylimides I as pigments or fluorescent dyes.
Last but not least, the 9-haloperylene-3,4-dicarbimides of the above-defined formula III have been found to be useful as intermediates for the preparation of the quaterrylimides I.
Any alkyl appearing in the formulae I and Ia may be straight-chain or branched. Substituted aryl may generally include up to 3, preferably 1 or 2, of the substituents mentioned.
Specific examples of suitable radicals R.sup.1 and X (and of their substituents) are: pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, 1-ethylpentyl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tridecyl, isotridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and eicosyl (the above designations isooctyl, isononyl, isodecyl and isotridecyl are
REFERENCES:
patent: 1715430 (1929-06-01), Schmidt et al.
patent: 4846892 (1989-07-01), Henning et al.
patent: 5405962 (1995-04-01), Muellen et al.
Nagao, Y. et al, Dyes and Pigments, 1991, 16, pp. 19-25.
Quante, H. et al, Angew. Chem. Int. Ed. Engl., 1995, 34(12), 1323-1325.
Seybold, G. et al, Dyes and Pigments, 1989, 11(4), pp. 303-317.
Bohm Arno
Mullen Klaus
Quante Heribert
BASF - Aktiengesellschaft
Dahlen Garth M.
Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V. B
Rotman Alan L.
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