Synthesis of glycerol-derived diallyl spiroorthocarbonates and the study of their antishrinking properties in acrylic dental resins

J Mater Sci Mater Med. 2013 Aug;24(8):2077-84. doi: 10.1007/s10856-013-4959-5. Epub 2013 May 28.

Abstract

In this work was evaluated the efficiency of an antishrinkage additive in a dental resin. This additive was a mixture 1:1 of five and six-membered ring spiroorthocarbonates functionalized with allylic groups (SOC DA). The aim of this study was to reduce the shrinkage of a typical dental resin composed of a blend of the dimethacrylates, Glycerolate bisphenol A dimethacrylate (Bis-GMA)/2-[(3,5,5-trimethyl-6-[2-(2-methyl prop-2-enoyloxy) ethoxycarbonylamino] hexyl) carbamoyloxy] ethyl, 2-methyl prop-2-enoate, (UDMA)/triethyleneglycol dimethacrylate (TEGDMA) in a 50:30.20 molar ratio, and silicon dioxide as filler. SOC DA was added at 5, 10 and 20 mol% to the already mentioned formulation. It was found that the addition of 20 mol% of SOC DA decreased 53 % the shrinkage of the cured composite material, in comparison with a formulation where it was not added the antishrinkage additive. Besides, the kinetics of photopolymerization determined by Real-Time infrared spectroscopy, demonstrated that the addition of increasing concentration of SOC DA improved the conversion of double bonds of dimethacrylates. Additionally, the presence of SOC DA at 10 % mol, helped to increase the flexural strength and the compressive strength of the composite, as a consequence of the augment of the crosslink density, induced by the ring opening polymerization of SOC DA.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrylic Resins / chemical synthesis
  • Acrylic Resins / chemistry*
  • Allyl Compounds / chemical synthesis
  • Allyl Compounds / chemistry
  • Carbonates / chemical synthesis*
  • Carbonates / chemistry
  • Compressive Strength
  • Dental Stress Analysis*
  • Glycerol / chemistry*
  • Kinetics
  • Materials Testing
  • Models, Biological
  • Pliability
  • Polymerization
  • Spectroscopy, Fourier Transform Infrared
  • Tensile Strength

Substances

  • Acrylic Resins
  • Allyl Compounds
  • Carbonates
  • Glycerol