From hydroxyurethane methacrylates to hybrid nonisocyanate polyurethanes

Abstract

New hybrid polyhydroxyurethane networks were quantitatively synthesized by radical polymerization of new hydroxyurethane methacrylate (HUMA) prepolymers. These HUMAs were synthesized in several steps. First, bis(cyclic carbonate) poly(propylene oxide) was reacted with two different diamines (ethylene diamine and 2,2′-(ethylenedioxy)diethylamine) in excess. Then, these end-functionalized hydroxyurethane prepolymers were converted into end-functionalized hydroxyl prepolymers by ring opening of ethylene carbonate. Finally, a methacrylate function was grafted to the hydroxyl functions. All these steps were performed at room temperature. These prepolymers were thermally either homopolymerized or copolymerized using benzylmethacrylate or poly(ethylene oxide) bisphenol A dimethacrylate as comonomers, leading to new hybrid nonisocyanate polyurethane networks with various properties. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019.