Synthesis and characterization of new polyamides containing p-phenylenediacryloyl moieties in the main chain

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-phenylenediacrytic 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. (C) 2008 Wiley Periodicals, Inc.