Application of microwave irradiation for synthesis of novel optically active poly(amide imides) derived from diacid chloride containing epiclon andL-isoleucine with aromatic diamines

Abstract

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 L-isoleucine (2) in acetic acid and the resulting imide acid (3) was obtained in high yield. The diacid chloride (4) was obtained from diacid derivative (3) by reaction with thionyl chloride. The polycondensation reaction of diacid chloride (4) with several aromatic diamines such as 4,4′-sulfonyldianiline (5a), 4,4′-diaminodiphenyl methane (5b), 4,4′-diaminodiphenylether (5c), p-phenylenediamine (5d), m-phenylenediamine (5e), 2,4-diaminotoluene (5f), and 4,4′-diaminobiphenyl (5g) 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 were also performed in two other different methods: low-temperature solution polycondensation and reflux conditions. A series of optically active poly(amide imides) with inherent viscosity of 0.12–0.30 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 imides) are reported. © 2004 Wiley Periodicals, Inc. J Appl Polym Sci 93: 2218–2229, 2004