Synthesis and characterization of N-isopropyl, N-methacryloxyethyl methacrylamide as a possible dental resin

Biomaterials. 2001 Mar;22(6):535-40. doi: 10.1016/s0142-9612(00)00209-x.

Abstract

In this study, N-isopropyl, N-methacryloxyethyl methacrylamide (NIMM) is proposed as a possible reactive diluent in place of triethylene glycol dimethacrylate (TEGDMA) for dental resin mixtures. Real-time infrared spectroscopy was used to monitor the double-bond conversion as a function of irradiation time, and mixtures of 50/50wt% bis-GMA/NIMM were found to reach final conversions (95%) that were 1.5 times greater than bis-GMA/TEGDMA (65%) under visible light irradiation. In addition, samples cured to these conversions were tested with dynamic mechanical analysis. The bis-GMA/NIMM mixture (100% converted) was found to have a higher glass transition temperature and modulus at body temperature than a comparable bis-GMA/TEGDMA mixture (60% converted). Finally, the water sorption and solubility of bis-GMA/NIMM were determined to be higher than the bisGMA/TEGDMA comparison, but the values were still within the range of the ISO 9000s standard. These results suggest that bis-GMA/NIMM mixtures are a viable alternative to conventional dental resins since a greater degree of monomer conversion is obtainable without sacrificing physical and mechanical properties.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Dental Materials / chemical synthesis*
  • Dental Materials / chemistry
  • Magnetic Resonance Spectroscopy
  • Methacrylates / chemical synthesis*
  • Methacrylates / chemistry
  • Polymers / chemistry
  • Resins, Plant / chemical synthesis*
  • Resins, Plant / chemistry
  • Solubility
  • Spectroscopy, Fourier Transform Infrared
  • Water / chemistry

Substances

  • Dental Materials
  • Methacrylates
  • N-isopropyl, N-methacryloxyethyl methacrylamide
  • Polymers
  • Resins, Plant
  • Water