Novel urethane-based polymer for dental applications with decreased monomer leaching

Mater Sci Eng C Mater Biol Appl. 2017 Mar 1:72:192-201. doi: 10.1016/j.msec.2016.11.050. Epub 2016 Nov 15.


The aim of this study was to synthesize and characterize new multifunctional-urethane-methacrylate monomers to be used as the organic matrix in restorative dental composites, and evaluate the main physical-chemical properties of the resulting material. Bis-GMA (bisphenol-A-diglycidylmethacrylate) and GDMA (glycerol dimethacrylate) were modified by reacting the hydroxyl groups with isocyanate groups of urethane-methacrylate precursors to result in the new monomeric systems U-(bis-GMA)-Mod and U-(GDMA)-Mod, U=Urethane and Mod=Modified. The modifications were characterized by FTIR and 1H NMR. The final monomeric synthesized system was used to prepare dental resins and composites. The physical-chemical properties were evaluated and compared with those of bis-GMA composites with varying filler contents or unfilled resins. U-(bis-GMA)-Mod and U-(GDMA)-Mod can be used to prepare dental restorative composites, with some foreseeable advantages compared with bis-GMA composites. One significant advantage is that these composites have the potential to be less toxic, once they presented a reduction of 50% in leaching of unreacted monomers extracted by solvent.

Keywords: Bisphenol A; Bisphenol A-glycidyl methacrylate; Composite resin; Methacrylates; Physicochemical phenomena; Urethane.

MeSH terms

  • Bisphenol A-Glycidyl Methacrylate / chemistry
  • Dental Materials / chemical synthesis
  • Dental Materials / chemistry*
  • Magnetic Resonance Spectroscopy
  • Methacrylates / chemistry
  • Polymers / chemical synthesis
  • Polymers / chemistry*
  • Solubility
  • Spectroscopy, Fourier Transform Infrared
  • Urethane / chemistry*
  • Water / chemistry


  • Dental Materials
  • Methacrylates
  • Polymers
  • Water
  • Urethane
  • Bisphenol A-Glycidyl Methacrylate