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Synthesis and Characterization of Methacrylate Derivatives of Oligo-Ether Carbonate Diols



S Bencherif, K S. Wilson, Elizabeth Wilder, Joseph M. Antonucci


Dimethacrylate monomers of several types are widely used in preventative and restorative dental applications. One such monomer that ushered in the modern era of polymeric based dental materials is 2,2-bis[p-(2'-hydroxy-3'-methacryloxyoxypropoxy)phenyl] propane or Bis-GMA. Bis-GMA has a moderate molecular mass of 512 but because of its two hydroxyl groups and rigid bisphenol-A core, it has a high viscosity. To achieve monomer systems with workable viscosities, Bis-GMA is usually admixed with a diluent difunctional methacrylate of lower molecular mass such as tri(ethylene glycol) dimethacrylate (TEGDMA). While this resin formulation approach yields monomer systems with manageable viscosities, it also results in significant increases to polymerization shrinkage and stress development, as well as biocompatibility concerns.An alternative resin formulation approach that can reduce the high viscosity of monomers such as Bis-GMA while also reducing polymerization shrinkage, and, possibly, enhancing biocompatibility, is to employ high molecular mass dimethacrylates that have flexible segments between vinyl functional groups. In this study we describe the synthesis and characterization of dimethacrylates derived from two relatively flexible diols.
Society for Biomaterials


Bis-GMA, conversion, dental monomer, methacrylate, polymerization shrinkage, viscosity


Bencherif, S. , Wilson, K. , Wilder, E. and Antonucci, J. (2005), Synthesis and Characterization of Methacrylate Derivatives of Oligo-Ether Carbonate Diols, Society for Biomaterials (Accessed April 24, 2024)
Created April 1, 2005, Updated February 19, 2017