Synthesis of Soluble,Curable, and Thermally Stable Aromatic Polyamides Bearing Thiourea and Pendent 4-Pyridylformylimino Groups

A new aromatic dicarboxylic acid monomer 4-pyridylformylimino-N-(phenyl,2′,5′ – dicarboxylic acid) (PPDC) containing pyridine and azomethine units was synthesized through a simple one-step condensation reaction between 2-aminoterephthalic acid and 4-pyridinecarboxaldehyde. A series of new polyamides was prepared through the direct one-pot phosphorylation polycondensation of PPDC with simple aromatic commercial diamines and diamines bearing phenylthiourea groups. The polyamides were characterized by FT-IR, ¹H-NMR, and ¹³C-NMR spectroscopy. Thermal stability of the polymers was evaluated using thermogravimetric analysis. The polyamides with inherent viscosities in the range of 0.30–0.51 dL/g showed an outstanding solubility in various solvents such as 1-methyl-2-pyrrolidone (NMP), dimethly sulfoxide (DMSO), N,N-dimethylformamide (DMF), N,N-dimetylacetamide (DMAc), and pyridine. The cured polyamides displayed significantly higher thermal stability than the uncured polyamides. The conductivity of the polyamides, when blended with 20% by weight of doped polyanilines, was in the range 3.09–4.21 × 10^?3 S cm^?1.