Stable Free Radical Polymerization of Acrylates Promoted by α-Hydroxycarbonyl Compounds

Abstract

The living-radical polymerization of n-butyl acrylate, moderated with TEMPO, is shown to proceed in a controlled fashion in the presence of a series of α-hydroxycarbonyl compounds with different organic bases. The best results were obtained with glyceraldehyde dimer in the presence of pyridine. These results further support the suggestion that the difficulty of polymerizing acrylate monomers in the presence of TEMPO is related to the excess buildup of TEMPO due to a small amount of polymer chain termination and to a lesser extent on the higher bond dissociation energy of the TEMPO acrylate bond relative to the TEMPO styrene bond at the chain's terminus.