Conversion of perylene-3,4:9,10-tetracarboximides to a form...

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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Reexamination Certificate

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07851628

ABSTRACT:
A process for converting perylene-3,4:9,10-tetracarboximides of the general formula Iin which R1and R2are each unbranched, branched or cyclic C1-C8-alkyl to a form suitable for use as fluorescent dyes, which comprisesa) dissolving or suspending the perylene-3,4:9,10-tetracarboximides whose molecules have a molecular volume of ≦230 Å3in an organic or inorganic solvent at from 0 to 250° C.,b1) cooling the solution obtained in step a) to or below the crystallization temperature and, in the case of an organic solvent, if desired at the same time removing excess solvent until the first crystals form, or, in the case of an inorganic solvent, adding water or dilute aqueous solutions of the solvent until the first crystals form, and maintaining the solution at this temperature for further crystallization orb2) cooling the suspension obtained in step a) to or below the crystallization temperature when the temperature in step a) was above the crystallization temperature, and maintaining the suspension at this temperature for further crystallization,c) isolating the solvate crystals formed in step b) andd) then removing the solvent from the solvate crystals,and also novel crystalline forms of perylene-3,4:9,10-tetracarboxylic diimides.

REFERENCES:
patent: 4446324 (1984-05-01), Graser
patent: 30 16 765 (1981-11-01), None
patent: 30 49 215 (1982-07-01), None
patent: 0 055 363 (1982-07-01), None
Rademacher, Andreas et al. “Loesliche Perylen-Fluoreszenzfarbstoffe mit hoher Photostabilitaet”, Chem. Ber., vol. 115, pp. 2927-2934, with English abstract, XP000881309 1982.
Graser, Fritz et al. “Kristallstruktur und Farbe bei Perylen-3,4:9,10-bis(dicarboximid)-Pigmenten”, Liebigs Ann. Chem., pp. 1994-2011, with English abstract, XP001070159 1980.
Seybold, G. et al. “New Perylene and Violanthrone Dyestuffs for Fluorescent Collectors”, Dyes and Pigments, vol. 11, No. 4, pp. 303-317, XP009016080 1989.
Lee, Sang Kwon et al. “Electrochemistry, Spectroscopy and Electrogenerated Chemiluminescence of Perylene, Terrylene, and Quaterrylene Diimides in Aprotic Solution”, J. Am. Chem. Soc., vol. 121, No. 14, pp. 3513-3520, XP002252150 1999.

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