Preparation and characterization of cyclopolymerizable resin formulations

An amine-catalyzed reaction between acrylates and formaldehyde has been used to convert mono-acrylates to difunctional monomers and di-acrylates to multifunctional oligomers by linking the acrylic double bonds together in 1,6-diene pairs. The resulting monomers and oligomers undergo efficient cyclopolymerization to high conversion with significantly less shrinkage than normally found for acrylates. In this study, a convenient single-step process was used with mixtures of mono- and di-acrylate starting materials to produce a series of resins with potential for effective cyclopolymerization. Incremental changes in the ethyl acrylate (EA) to ethoxylated bisphenol A diacrylate (EBPAD) ratio directly supplied cyclopolymerizable resins with a broad range of viscosities and product distributions. Those resins produced from reaction mixtures rich in EA have low viscosities because of high diluent monomer contents and limited oligomerization of EBPAD due to end-cap formation. Resin viscosity and average molecular weight of the oligomeric component of the resin were inversely related to the amount of EA used in the reaction. Through the choice of reactants and their ratio, this simple technique has the potential to provide cyclopolymerizable resins for use in a variety of dental polymer applications.