New Polyamides Based on Bis(p-amidobenzoic acid)-p-phenylene diacrylic acid and Hydantoin Derivatives: Synthesis and Characterization


Abstract: Bis(p-amidobenzoic acid)-p-phenylene diacrylic acid (6) as a new monomer containing p-phenylenediacryloyl moiety was synthesized by using a 3-step reaction. At first p-phenylenediacrylic acid (3) was prepared by reaction of terephthal aldehyde (1) with malonic acid (2) in the presence of pyridine, and 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). Then 6 new polyamides (8a-f) containing p-phenylenediacryloyl and hydantoin moiety in the main chain were prepared by the direct polycondensation reaction of bis(p-amidobenzoic acid)-p-phenylene diacrylic acid (6) with 6 different hydantoin derivatives (7a-f) by 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 0.32-0.50 dL/g. The resulting polyamides were characterized by elemental analysis, viscosity measurements, thermal gravimetric analysis (TGA and DTG), solubility test, FT-IR, and UV-vis spectroscopy.

Keywords: Polyamides, p-phenylenediacryloyl moieties, bis(p-amidobenzoic acid)-p-phenylene diacrylic acid, hydantoin derivatives

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