Synthesis and Properties of Organosoluble and Optically Active Poly(amide-imide)s Based on Epiclon and (S)-(+)-Valine under Microwave Irradiation

摘要

Aliphatic dianhydride, Epiclon [3a,4,5,7a-tetrahydro-7-methyl-5-(tetrahydro-2,5-dioxo-3-furanyl)-1,3-isobenzofurandione] or [5-(2,5-dioxotetrahydrofurfuryl)-3-methyl-3-cyclohexyl-1,2-dicarboxylic acid anhydride] 1 was reacted with (S)-(+)-valine 2 in acetic acid and the resulting imide-acid 3 was obtained in high yield. The diacid chloride 4 was obtained from the reaction of 3 with thionyl chloride. The polycondensa-tion reaction of diacid chloride 4 with several aromatic diamines such as 4,4′-sulphonyl-dianiline 5a, 4,4′-diaminodiphenyl methane 5b, 4,4′-diaminodiphenylether 5c, p-phenylenediamine 5d, m-phenylenediamine 5e, 2,4-diaminotoluene 5f and 4,4′-diamino-biphenyl 5g was developed by using a domestic microwave oven in the presence of a small amount of o-cresol. The polymerization reactions were also performed by two another methods: low temperature solution polycondensation and reflux conditions. A series of optically active poly(amide-imide)s with inherent viscosity of 0.13-0.32 dL/g were obtained. All of the above polymers were fully characterized by IR, elemental analyses and specific rotation techniques. Some structural characterizations and physical properties of these optically active poly(amide-imide)s are reported.