Polymerization via zwitterion 27. No-catalyst copolymerization of 2-phenyl-1,3,2-dioxaphospholane with β-hydroxyalkyl acrylates and methacrylates

Summary This paper describes No-Catalyst Copolymerizations between ethylene phenylphosphonite (EPO) as M_N and four -hydroxyalkyl acrylates and methacrylates as M_E. In all combinations polyphosphinate type copolymers were obtained above 130 °C without added catalyst. The first step of reaction was a proton-transfer step to yield a transient phosphonium-alkoxide zwitterion 5 and generated a phosphorane intermediate like 6. The subsequent reactions of 6 were rather complicated. It was possible to conceive several zwitterions to lead to polymer units. The liberation of ethylene oxide and/or propylene oxide was observed as a side reaction during polymerization.Dedicated to the 60th birthday of Professor C. I. Simionescu