Synthesis of Novel Heterocyclic Polyimides Containing Trimellitimide Acid Moieties

摘要

4-Nitrobezoyl chloride (2) was reacted with isocugenol in chloroform inthe presence of triethyl amine and ester (4) was obtained inhigh yield. Ester (4) was reacted with SnCl_2.2H_2O to give amine-ester (5), and subsequently was reacted with trimellitic anhydride (6) and novel isoeugenol ester-imide derivative (7), as a new monomer was obtained in quantitative yield. Compound (7) was characterized by high-field ~1H-NMR, IR, and elemental analysis and then was used for the preparation of model comopound (9) and polymerization reactions. 4-Phenyl-1,2,4-triazoline-3,5-dione (PhTD) (8) was allowed to react with compound (7). The reaction is very fast and gives only one double adduct (9) via Diels-Alder and ene pathways in excellent yield. The polymeriation reactions of novel monomer (7) with bistriazolinediones [bis(p-3,5-dioxo-1,2,4-triazolin-4-ylphenyl)methane (10) and 1,6-bis(3,5-dioxo-1,2,4-triazolin-4-y-)hexane (11)] were carried out in N,N-dimethylacetamide (DMAc) at room temperature. The reactions are exothermic, fast, and gave novel heterocyclic polyimides (12) and (13) via repetitive Diels-Alder-ene polyaddition reactions. Some structural characterization and physical properties of these novel heterocyclic polyimides are reported.