Synthesis and Polymerization of New Multifunctional Pyrrolidinone Methacrylate Monomers

Jean-Francois Morizur, University of Southern Mississippi
Hui Zhou, University of Southern Mississippi
Charles E. Hoyle, University of Southern Mississippi
Lon J. Mathias, University of Southern Mississippi


Methacrylate monomers have been widely used in medical and dental applications such as bone cements, dental fillings, bioadhesives, and hydrogels. One major problem of these monomers resides in their low rates of polymerization leading to leaching problems that cause irritation of the surrounding tissues and even cell death. Here we describe the synthesis and polymerization of new mono-methacrylates containing multifunctional pyrrolidinone moieties. Such monomers possess stronger inherent hydrogen bonding potential susceptible to increase their reactivity and polymerization rates. These monomers were shown to homopolymerize rapidly leading to crosslinked polymers. The corresponding rates of polymerization were found to be comparable to difunctional methacrylates such as hexanediol dimethacrylate. Intermolecular hydrogen bonding interactions involving the pyrrolidinone unit leads these monomers to behave as "pseudo" difunctional monomers upon homopolymerization. (C) 2009 Elsevier Ltd. All rights reserved.