Synthesis of an allyl carbonate monomer as alternative to TEGDMA in the formulation of dental composite resins

J Mech Behav Biomed Mater. 2018 Nov:87:148-154. doi: 10.1016/j.jmbbm.2018.07.016. Epub 2018 Jul 30.

Abstract

Over the past years, significant effort has been dedicated to synthesizing low-shrinking formulations, however, development of dental composites with low volumetric shrinkage continues to be challenging. The purpose of this study was to synthesize a bisphenol allylic derivate (BPhADAC) and evaluate its inclusion in the formulation of a photopolymerizable dental composite resin, as a BisGMA diluent. Experimental (BisGMA/BPhADAC) and control (BisGMA/TEGDMA) photopolymerizable composites were prepared. Double bond conversion, polymerization kinetics, volumetric shrinkage, water sorption, solubility, and flexural properties were investigated. The experimental composite showed higher degree of conversion values, less volumetric shrinkage and less water sorption than the control composite (p < 0.05). In addition, flexural strength between the materials was found to be similar. The overall properties prove that the allylic monomer BPhADAC could be potentially useful in the formulation of low-shrinking dental composite resins.

MeSH terms

  • Acrylic Resins / chemistry*
  • Acrylic Resins / toxicity
  • Animals
  • Bisphenol A-Glycidyl Methacrylate / chemistry
  • Carbonic Acid / chemical synthesis*
  • Carbonic Acid / chemistry*
  • Cell Line
  • Cell Survival / drug effects
  • Chemistry Techniques, Synthetic
  • Color
  • Composite Resins / chemistry*
  • Composite Resins / toxicity
  • Drug Compounding
  • Elastic Modulus
  • Flexural Strength
  • Kinetics
  • Mice
  • Photochemical Processes
  • Polyethylene Glycols / chemistry*
  • Polymerization
  • Polymethacrylic Acids / chemistry*
  • Polyurethanes / chemistry*
  • Polyurethanes / toxicity
  • Solubility
  • Water / chemistry

Substances

  • Acrylic Resins
  • Composite Dental Resin
  • Composite Resins
  • Polymethacrylic Acids
  • Polyurethanes
  • Water
  • triethylene glycol dimethacrylate
  • Polyethylene Glycols
  • Bisphenol A-Glycidyl Methacrylate
  • Carbonic Acid