Synthesis of polyarylamines by vinylogous nucleophilic substitution polymerization of bis(4-chloro-3-nitrophenyl) sulfone with diamines

A series of new polyarylamines was prepared by the vinylogous nuclephilic substitution polymerization of bis(4-chloro-3-nitrophenyl) sulfone with both aromatic and aliphatic diamines. The synthesis involves the solution polycondensation in a polar aprotic solvent at elevated temperatures, a tertiary amine being used as an acid acceptor. Of these solvents, dimethyl sulfoxide and N-methyl-2-pyrrolidone were the most effective for the preparation of high molecular weight polymers. The polyarylamines having inherent viscosities in the range of 0.1–0.5 were all amorphous and highly soluble in polar aprotic solvents. Thermogravimetric analysis under both air and nitrogen atmospheres indicated that rapid decomposition began above 300°C for the polyarylamines from aromatic diamines.