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Synthesis and properties of poly(amide–imide)s based on N , N ′‐bis(4‐carboxyphenyl)‐4,4′‐oxydiphthalimide, p ‐aminobenzoic acid and various aromatic diamines
Author(s) -
Yang ChinPing,
Chen RueiShin,
Hung KueiShi,
Woo Eamor M
Publication year - 2002
Publication title -
polymer international
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.592
H-Index - 105
eISSN - 1097-0126
pISSN - 0959-8103
DOI - 10.1002/pi.870
Subject(s) - condensation polymer , imide , polymer chemistry , diamine , solubility , triphenyl phosphite , amide , polyamide , solvent , inherent viscosity , chemistry , materials science , organic chemistry , polymer , intrinsic viscosity
A new diimide–diacid monomer, N , N ′‐bis(4‐carboxyphenyl)‐4,4′‐oxydiphthalimide (I), was prepared by azeotropic condensation of 4,4′‐oxydiphthalic anhydride (ODPA) and p ‐aminobenzoic acid ( p ‐ABA) at a 1:2 molar ratio in a polar solvent mixed with toluene. A series of poly(amide–imide)s (PAI, III a–m ) was synthesized from the diimide–diacid I (or I′, diacid chloride of I) and various aromatic diamines by direct polycondensation (or low temperature polycondensation) using triphenyl phosphite and pyridine as condensing agents. It was found that only III k–m having a meta ‐structure at two terminals of the diamine could afford good quality, creasable films by solution‐casting; other PAIs III using diamine with para ‐linkage at terminals were insoluble and crystalline; though III g–i contained the soluble group of the diamine moieties, their solvent‐cast films were brittle. In order to improve their to solubility and film quality, copoly(amide–imide)s (Co‐PAIs) based on I and mixtures of p ‐ABA and aromatic diamines were synthesized. When on equimolar of p ‐ABA ( m = 1) was mixed, most of Co‐PAIs IV had improved solubility and high inherent viscosities in the range 0.9–1.5 dl g −1 ; however, their films were still brittle. With m = 3, series V was obtained, and all members exhibited high toughness. The solubility, film‐forming ability, crystallinity, and thermal properties of the resultant poly(amide–imide)s were investigated. © 2002 Society of Chemical Industry