Synthesis of formamidine-containing polymers from aromatic diamines

Abstract

Aromatic polymers containing formamidine groups in the polymer backbone were obtained from aromatic diamines in high yields with Α,Α-dichloromethyl ether and triethylorthoformate. The latter was the reagent of choice. Soluble, high-molecular-weight products were obtained with m -phenylene diamine and 4,4′ bis(aminophenyl)methane. These polymers were characterized by viscosity, microanalysis, and nuclear magnetic resonance and infrared spectroscopy. Generally, insoluble products were obtained from p -phenylene diamine and 2,6-diaminotoluene, although small amounts of dimethylsulfoxide (DMSO)-soluble fractions could be extracted and examined by NMR spectroscopy. IR analysis of the insoluble fractions confirmed formation of polymers with the formamidine-containing structures. The synthetic procedures developed here make readily available this new class of aromatic polymers.