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Synthesis and Characterization of Optically Active Poly(Amide-Imide)s with Hydantoin and Thiohydantoin Derivatives in Main Chain

Hydantoin and thiohydantoin derivatives 4(a-e) were synthesized from reactions of

benzil and benzil derivatives 3(a-e) with urea and thiourea. 5,5-dimethylhydantoin

4f was synthesized from the reactions of acetone cyanohydrin 3f and ammonium

carbonate. Benzil and benzil derivatives 3(a-e) were obtained from oxidation of benzoin

and benzoin derivatives 2(a-e) with concentrated nitric acid. Benzoin and benzoin

derivatives were obtained from benzoin condensation of benzaldehyde and benzaldehyde

derivatives. Hydantoin and thiohydantoin derivatives 4(a-e) were characterized by

melting points, elemental analysis, FTIR, 1H NMR and 13C NMR spectroscopy. The

polycondensation reactions of 4,4-carbonyl-bis(phthaloyl-L-alanine) diacid chloride 5 with

six different derivatives of hydantoin and thiohydantoin compounds 4(a-f) were carried

out in DMAc solution in the presence of pyridine. The resulting poly(amide-imide)s, PAIs,

6(a-f) with inherent viscosities about 0.15-0.38 dL/g were obtained in high yield and were

optically active and thermally stable. All of the above compounds were fully characterized

by means of FTIR spectroscopy, elemental analysis, inherent viscosity (ηinh),

solubility test and specific rotation. Thermal properties of the PAIs 6(a-f) were

investigated using thermal gravimetric analysis (TGA).

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