Synthesis and functionalization of bromomethylated poly(phenylene sulfide)

A soluble poly(phenylene sulfide) (PPS) derivative was synthesized by oxidative polymerization of bis(3,5-dimethylphenyl) disulfide. The obtained poly(thio-2,6-dimethyl-1,4-phenylene) ( I ) (M_w = 22 900, M_n = 8 400) was brominated by the reaction with N-bromosuccinimide (NBS). The bromomethyl substituents on PPS are reactive and were converted quantitatively to hydroxymethyl groups by hydrolysis in NMP at 100°C. The reaction of the bromomethylated PPS with tertiary amines gave the quaternized polymer, which is stable up to 145°C in the solid state and in refluxing methanol.