화학공학소재연구정보센터
Journal of Applied Polymer Science, Vol.86, No.9, 2211-2216, 2002
Microwave-assisted synthesis of new optically active poly(ester-imide)s containing N,N'-( pyromellitoyl)-bis-L-phenylalanine moieties
Pyromellitic dianhydride (benzene-1,2,4,5-tetracarboxylic dianhydride) (1) was reacted with L-phenylalanine (2) in a mixture of acetic acid and pyridine (3: 2) and the resulting imide-acid [NN'-(pyromellitoyl)-bis-L-phenylalanine diacid] (4) was obtained in quantitative yield. The compound (4) was converted to the NN'-(pyromellitoyl)bis-L-phenylalanine diacid chloride (5) by reaction with thionyl chloride. A new facile and rapid polycondensation reaction of this diacid chloride (5) with several aromatic diols such as phenol phthalein (6a), bisphenol-A (6b), 4,4'-hydroquinone (6c), 1,8-dihydroxyanthraquinone (6d), 4,4-dihydroxy biphenyl (6e), and 2,4-dihydroxyacetophenone (6f) was developed by using a domestic microwave oven in the presence of a small amount of a polar organic medium such as o-cresol. The polymerization reactions proceeded rapidly and are completed within 20 min, producing a series of optically active poly(ester-imide)s with good yield and moderate inherent viscosity of 0.10-0.26 dL/g. All of the above polymers were fully characterized by IR, elemental analyses, and specific rotation. Some structural characterization and physical properties of these optically active poly(esterimide)s are reported.