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Synthesis and characterization of new polyamides containing p ‐phenylenediacryloyl moieties in the main chain
Author(s) -
Faghihi Khalil,
Naghavi Howra
Publication year - 2008
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.27702
Subject(s) - condensation polymer , thionyl chloride , inherent viscosity , polymer chemistry , chemistry , phenylene , pyridine , polyamide , diamine , malonic acid , moiety , condensation reaction , dicarboxylic acid , intrinsic viscosity , chloride , organic chemistry , polymer , catalysis
Abstract Six new polyamides 8a–f containing p ‐phenylenediacryloyl moieties in the main chain were prepared by the direct polycondensation reaction of bis( p ‐amidobenzoic acid)‐ p ‐phenylene diacrylic acid 6 with 1,4‐diphenylene diamine 7a , 1,3‐diamino toluene 7b , 1,5‐diamino naphthalene 7c , 4,4′‐diamino diphenyl ether 7d , 4,4′‐diamino diphenyl sulfone 7e , and 3,3′‐diamino diphenylsulfone 7f by using thionyl chloride, N ‐methyl‐2‐pyrolidone, and pyridine as condensing agents. These new polymers 8a–f were obtained in high yield and inherent viscosity between 0.35–0.65 dL/g. The resulting polyamides were characterized by elemental analysis, viscosity measurements, thermal gravimetric analysis (TGA and DTG), solubility test, FTIR and UV–vis spectroscopy. Diacid acid 6 as a new monomer containing p ‐phenylenediacryloyl moiety was synthesized by using a three‐step reaction. First, p ‐phenylenediacrylic acid 3 was prepared by reaction of terephthal aldehyde 1 with malonic acid 2 in the presence of pyridine, then diacid 3 was converted to p ‐phenylenediacryloyl chloride 4 by reaction with thionyl chloride. Finally, bis( p ‐amidobenzoic acid)‐ p ‐phenylene diacrylic acid 6 was prepared by the condensation reaction of phenylenediacryloyl chloride 4 with p ‐aminobenzoic acid 5 . © 2008 Wiley Periodicals, Inc. J Appl Polym Sci, 2008