Investigation on synthesis and properties of isosorbide based bis-GMA analogue

J Mater Sci Mater Med. 2012 May;23(5):1149-55. doi: 10.1007/s10856-012-4594-6. Epub 2012 Mar 10.


The aim of this work was to synthesize and investigate properties of a novel dimethacrylic monomer based on bioderived alicyclic diol--isosorbide. Its potential as a possible substitute of 2,2-bis[4-(2-hydroxy-3-methacryloyloxypropoxy)phenyl]propane (BISGMA), widely used in dental restorative materials and suspected for toxicity was assessed. The novel monomer was obtained in a three-step synthesis. First, isosorbide was etherified by a Williamson nucleophilic substitution and subsequently oxidized to isosorbide diglycidyl ether (ISDGE). A triphenyl phosphine catalyzed addition of methacrylic acid to ISDGE resulted in 2,5-bis(2-hydroxy-3-methacryloyloxypropoxy)- 1,4:3,6-dianhydro-sorbitol (ISDGMA). The monomer obtained was photopolymerized using camphorquinone/2-(dimethylamino)ethyl methacrylate initiating system. Next, compositions with triethylene glycol dimethacrylate (TEGDMA) were prepared and polymerized. Double bond conversion, polymerization shrinkage and water sorption of resulting polymers were determined. Selected mechanical (flexular strength and modulus, Brinell hardness) and thermomechanical (DMA analysis) properties were also investigated. BISGMA based materials were prepared as reference for comparison of particular properties.

Publication types

  • Evaluation Study

MeSH terms

  • Adsorption
  • Biomechanical Phenomena
  • Bisphenol A-Glycidyl Methacrylate / chemical synthesis
  • Bisphenol A-Glycidyl Methacrylate / chemistry*
  • Composite Resins / chemical synthesis
  • Composite Resins / chemistry
  • Dental Materials / chemical synthesis*
  • Dental Materials / chemistry*
  • Elastic Modulus
  • Hardness / physiology
  • Isosorbide / analogs & derivatives*
  • Isosorbide / chemical synthesis
  • Isosorbide / chemistry
  • Materials Testing
  • Models, Biological
  • Polymerization
  • Specific Gravity
  • Water / metabolism
  • Wettability


  • Composite Resins
  • Dental Materials
  • Water
  • Bisphenol A-Glycidyl Methacrylate
  • Isosorbide