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Polyimides based on new diamines having pendant imide groups

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Abstract

New aromatic diamines were prepared in two steps from 4,5-dichlorophthalic anhydride and primary amines. The resulting 4,5-dichlorophthalimide was reacted with 4-mercaptoaniline, so that the chloroatoms were substituted by the mercapto groups (via the sulfide anions). The new diamines were polycondensed either with the diphenyl ether 3,3′,4,4′-tetracarboxylic anhydride or with bicyclooctane tetracarboxylic anhydride. These polycondensations were conducted in boiling m-cresol with azeotropic removal of water. The isolated polyimides were characterized by viscosity measurement, IR-spectroscopy, elemental analyses, and MALDI-TOF mass spectrometry. The mass spectra evidenced a high content of cyclic polyimides, indicating nearly perfect reaction conditions. The mass spectra also proved the formation of copolymers containing one diamine with a trialkylamine group in the side chain. High glass transition temperatures but a low crystallization tendency were found by DSC measurements. © 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 43: 6272–6281, 2005

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