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Application of microwave irradiation for synthesis of novel optically active poly(amide imides) derived from diacid chloride containing epiclon and L ‐isoleucine with aromatic diamines
Author(s) -
Mallakpour Shadpor,
Kowsari Elaheh
Publication year - 2004
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.20738
Subject(s) - thionyl chloride , inherent viscosity , condensation polymer , specific rotation , polymer chemistry , chemistry , acetic anhydride , imide , amide , chloride , polyamide , acyl chloride , polymerization , intrinsic viscosity , acetic acid , dicarboxylic acid , organic chemistry , polymer , catalysis
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