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High Performance Polymers
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Cyclic Polyimides - A Comparison of Synthetic Methods

Hans R. Kricheldorf

Institut für Technische und Makromolekulare Chemie, Bundesstr. 45, D-20146 Hamburg, Germanykricheld{at}chemie.uni-hamburg.de

Gert Schwarz

Institut für Technische und Makromolekulare Chemie, Bundesstr. 45, D-20146 Hamburg, Germany

Shu-Ching Fan

Department of Chemical Engineering, R & D Center for Membrane Technology, Chung Yuan University, Chung Li, Taiwan 32023, ROC

Two different aliphatic anhydrides and three aromatic diamines were selected to prepare polyimides soluble in chloroform and dichloromethane. Five synthetic methods were compared: polycondensation with triphenylphosphate (Higashi method), polycondensation in hot m-cresol and in hot 1,2-dichlorobenzene, polycondensation in bulk or in solution in the presence of acetic anhydride and polycondensation in ionic liquids. The highest molecular weights were obtained in m-cresol and in NN'-bis(n-propyl)imidazolium bromide. The matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) mass spectra revealed that the fraction of cyclic polyimides increased with the molecular weight of the entire sample. The identification of high molar mass cycles (detected up to 12 000 Da) was limited by the mass spectrometry, not by the chemical course of the polycondensations.

Key Words: Polyimides • polycondensation • cyclization • ionic liquids • MALDI-TOF

High Performance Polymers, Vol. 16, No. 4, 543-555 (2004)
DOI: 10.1177/0954008304041031
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