Multifunctional Acrylic Ether Monomers, Their Polymers, and Polymerizable Epoxide Derivatives From Simple Alpha-Substitution of Alkly Acrylates

Abstract : Our group has been exploring the synthesis of 1,1-disubstituted monomers and their polymers obtained via the DABCO catalyzed hydroxy-methylation of alkyl acrylates. Previous work in this area has involved complicated or low yield syntheses. We are using a simple, clean synthetic technique using paraformaldehyde and neat substrate to produce alkyl alpha(hydroxymethyl) acrylates, albeit in yields of only 25-30%. Conversion of the hydroxymethyl group with thionyl chloride gives a reactive allyl chloride which allows a wide range of ether forming reactions to be applied. The ether linkage is inherently more stable than the ester linkage and is much more flexible