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Synthesis and Characterization of Novel Optically Active and Flame-Retardant Heterocyclic Polyimides


Tetrachlorophthalic anhydride (1) was reacted with L-leucine (2) in toluene solution at refluxing temperature in the presence of triethylamine and the resulting imide-acid (4) was obtained in quantitative yield. The compound (4) was converted to the N-(tetrachlorophthaloyl)-L-leucine acid chloride (5) by reaction with thionyl chloride. The reaction of this acid chloride (5) with isoeugenol (6) was carried out in chloroform and novel optically active isoeugenol ester derivative (7) as a chiral monomer was obtained in high yield. The compound (7) was characterized by 1H-NMR, IR, Mass and elemental analysis, and then was used for the preparation of model compound (10) 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 diastereomer of (10) via Diels–Alder and ene pathways in excellent yield. The polymerization reactions of novel monomer (7) with bistriazolinediones [bis-(p-3,5-dioxo-1,2,4-triazolin-4-ylphenyl)methane (11) and 1,6-bis-(3,5-dioxo-1,2,4-triazolin-4-yl)hexane] (12) were carried out in N,N-dimethylacetamide (DMAc) at room temperature. The reactions are exothermic, fast, and give novel optically active polymers (13) and (14) via repetitive Diels–Alder-ene polyaddition reactions. The resulting polymers are optically active, thermally stable, and flame resistant. All of the above compounds were fully characterized by IR, 1H-NMR, elemental analysis, and specific rotation. Some structural characterization and physical properties of these novel heterocyclic polyimides are reported. © 2000 John Wiley & Sons, Inc. J Appl Polym Sci 76: 240–248, 2000


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