Novel synthesis of polyureas by ring-opening polyaddition-condensation reaction of 2-phenyl-1,3,4-oxadiazolin-5-one with diamines

Abstract

A novel method for the synthesis of polyureas has been developed. This method involves ring-opening addition reaction of 2-phenyl-1,3,4-oxadiazolin-5-one with diamines, bis(4-aminophenyl) ether, 4,4′-methylenedianiline and m-xylylenediamine, followed by self-polycondensation of the resulting ring-opened adducts. Polymerizations in m-cresol at 150°C proceeded fast and were almost completed within 5 h. Polyureas were produced with reduced viscosities up to 0,38 dL · g−1. A model compound study was performed to demonstrate the feasibility of the reaction for the formation of polyureas.