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Microwave‐promoted rapid synthesis of new optically active poly(amide imide)s derived from N,N ′‐(pyromellitoyl)‐bis‐ L ‐isoleucine diacid chloride and aromatic diamines
Author(s) -
Mallakpour Shadpour,
Shahmohammadi Mohammad Hassan
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.13720
Subject(s) - thionyl chloride , polymer chemistry , specific rotation , imide , polymerization , chemistry , condensation polymer , amide , pyromellitic dianhydride , inherent viscosity , acryloyl chloride , chloride , polymer , organic chemistry , polyimide , monomer , intrinsic viscosity , acrylate , layer (electronics)
A pyromellitic dianhydride (benzene‐1,2,4,5‐tetracarboxylic dianhydride) was reacted with L ‐isoleucine in acetic acid, and the resulting imide acid [ N,N ′‐(pyromellitoyl)‐bis‐ L ‐isoleucine] (4) was obtained in a high yield. 4 was converted into N,N ′‐(pyromellitoyl)‐bis‐ L ‐isoleucine diacid chloride by a reaction with thionyl chloride. The polycondensation reaction of this diacid chloride with several aromatic diamines, including 1,4‐phenylenediamine, 4,4′‐diaminodiphenyl methane, 4,4′‐diaminodiphenylsulfone (4,4′‐sulfonyldianiline), 4,4′‐diaminodiphenylether, 2,4‐diaminotoluene, and 1,3‐phenylenediamine, was developed with two methods. The first method was polymerization under microwave irradiation, and the second method was low‐temperature solution polymerization, with trimethylsilyl chloride used as an activating agent for the diamines. The polymerization reactions proceeded quickly and produced a series of optically active poly(amide imide)s with good yields and moderate inherent viscosities of 0.17–0.25 dL/g. All of the aforementioned polymers were fully characterized by IR, elemental analyses, and specific rotation. Some structural characterization and physical properties of these optically active poly(amide imide)s are reported. © 2004 Wiley Periodicals, Inc. J Appl Polym Sci 92: 951–959, 2004