Synthesis and characterization of a novel resin monomer with low viscosity

J Dent. 2017 Apr:59:11-17. doi: 10.1016/j.jdent.2017.01.006. Epub 2017 Jan 22.

Abstract

Objective: In this study, we designed and synthesized a novel macromolecule (tetramethyl bisphenol F acrylate, TMBPF-Ac) with low viscosity, excellent mechanical properties, and good biocompatibility. It could be used as a monomer for dental resin composites, which could reduce the risk of human exposure to bisphenol A derivatives in the oral environment. In addition, the monomer could be used without diluent, thereby avoiding the negative effect of a diluent METHODS: TMBPF-Ac was synthesized by a multistep condensation reaction. Its structure was confirmed by 1H NMR spectra. Different resin mixtures were prepared, and then a number of performance and cytotoxicity tests were performed on these specimens.

Results: 1H NMR spectra showed that the structure of TMBPF-Ac was in accordance with the design. The viscosity of TMBPF-Ac was obviously lower than that of bisphenol-A diglycidyl methacrylate. The three kinds of resins used in this study were in line with ISO 4049:2009 and ISO 10993-5:2009. TMBPF-Ac-based resin had better physical and biological properties.

Keywords: Acrylate; BPA free; Dental resin composites; Low viscosity; Monomer.

MeSH terms

  • Acrylates / chemistry
  • Acrylic Resins / chemical synthesis*
  • Acrylic Resins / chemistry*
  • Acrylic Resins / toxicity
  • Benzhydryl Compounds / chemistry
  • Benzhydryl Compounds / toxicity
  • Biocompatible Materials / chemical synthesis
  • Biocompatible Materials / chemistry
  • Chemical Phenomena
  • Chemistry Techniques, Synthetic
  • Composite Resins / chemical synthesis*
  • Composite Resins / chemistry*
  • Composite Resins / toxicity
  • Compressive Strength
  • Dental Materials / chemical synthesis
  • Dental Materials / chemistry
  • Epoxy Resins / chemistry
  • Humans
  • Inhalation Exposure
  • Magnetic Resonance Spectroscopy
  • Materials Testing
  • Methacrylates / chemical synthesis
  • Methacrylates / chemistry
  • Phenols / chemistry
  • Phenols / toxicity
  • Polymerization
  • Polyurethanes / chemical synthesis*
  • Polyurethanes / chemistry*
  • Polyurethanes / toxicity
  • Stress, Mechanical
  • Tensile Strength
  • Viscosity*
  • Water / chemistry

Substances

  • Acrylates
  • Acrylic Resins
  • Benzhydryl Compounds
  • Biocompatible Materials
  • Composite Dental Resin
  • Composite Resins
  • Dental Materials
  • Epoxy Resins
  • Methacrylates
  • Phenols
  • Polyurethanes
  • bisphenol F
  • Water
  • acrylic acid
  • bisphenol A