Poly(amide imide)s from Bicyclo[2. 2. 2]oct-7-ene-2, 3, 6-tricarboxylic Acid 2, 3-Anhydride and Various Diamines

Abstract

New poly (amide imide)s containing the bicyclooctene ring in the chain were synthesized in N, N -dimethylacetamide (DMA) by condensation of 7- ( chloroformyl)b icyclo[2.2.2 ]oct-5-ene2, 3-dicarboxylic anhydride (BTR-Cl) with various diamines. BTR-Cl was prepared by the reaction of bicyclo[2.2.2]oct-7-ene-2, 3, 6-tricarboxylic acid 2, 3-anhydride (BTR) with thionyl chloride. BTR-Cl reacted with a diamine at -15°C, and then the temperature was slowly elevated to 166°C. The reaction mechanism for the"formation of these polymers was investigated by the IR spectra of the initial reaction products. The reaction appeared to proceed in three steps;( 1 ) the dehydrochlorination reaction, ( 2 ) the polyaddition reaction and ( 3 ) the imi-C dation, similar to the mechanism of poly (amide imide) s formations. The imidation took place at 130°C in the case of these poly (amide imide) s. The intrinsic viscosities of the polymers ranged from 0.15∼0.63 dl/g. These polymers were thermally less stable than aromatic poly (amide imide) s. However, these polymers were soluble in the solvents such as N-methylpyrrolidone, N, N-dimethylformamide and DMA to obtain the polymer solution easily in such a high concentration as 30 g/100ml