Synthesis and characterization of a new dimethacrylate monomer based on 5,50-bis(4-hydroxylphenyl)-hexahydro-4,7-methanoindan for root canal sealer application

J Mater Sci Mater Med. 2010 Apr;21(4):1135-42. doi: 10.1007/s10856-009-3979-7.

Abstract

In this study, a new dimethacrylate monomer 5,5'-bis[4-(2'-hydroxy-3'-methacryloyloxy-propoxy)-phenyl]-hexahydro-4,7-methan-oindan (5,5'-BHMPHM) with molecular weight of 640 and large molecular volume was designed and synthesized. The structure of monomer 5,5'-BHMPHM was confirmed by FT-IR, 1H-NMR and elemental analysis. Degree of double bond conversion, volume shrinkage, contact angle, water sorption and solubility, diffusion coefficient value, flexure strength and modulus of 5,5'-BHMPHM/tri(ethylene glycol) dimethacrylate (TEGDMA) based resin were measured. 2,2-bis[4-(2'-hydroxy-3'-methacryloyloxy-propoxy)-phenyl]-propane(Bis-GMA)/TEGDMA based resin was used as reference. The result illustrated that the double bond conversion, polymerization shrinkage, and diffusion coefficient value of 5,5'-BHMPHM/TEGDMA based resin were significantly lower than that of Bis-GMA/TEGDMA based resin (P<0.05). Water sorption, solubility, flexure strength and modulus of 5,5'-BHMPHM/TEGDMA based resin were higher than that of Bis-GMA/TEGDMA based resin (P<0.05). There was no statistical difference between 5,5'-BHMPHM/TEGDMA based resin and Bis-GMA/TEGDMA based resin in contact angle (P>0.05).

Publication types

  • Evaluation Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adsorption
  • Biocompatible Materials / chemical synthesis
  • Biocompatible Materials / chemistry
  • Biocompatible Materials / pharmacokinetics
  • Composite Resins / chemical synthesis
  • Composite Resins / chemistry
  • Dental Restoration, Permanent / instrumentation
  • Dental Restoration, Permanent / methods
  • Dental Stress Analysis
  • Elastic Modulus
  • Hardness
  • Indans / chemistry*
  • Materials Testing
  • Methacrylates / chemical synthesis*
  • Methacrylates / chemistry*
  • Methylmethacrylates / chemistry*
  • Polyethylene Glycols / chemistry
  • Polymethacrylic Acids / chemistry
  • Root Canal Filling Materials / chemical synthesis*
  • Root Canal Filling Materials / chemistry
  • Root Canal Filling Materials / pharmacokinetics
  • Tensile Strength
  • Water / metabolism

Substances

  • 5,5'-bis(4-(2'-hydroxy-3'-methacryloyloxypropoxy)phenyl)hexahydro-4,7-methanoindan
  • Biocompatible Materials
  • Composite Resins
  • Indans
  • Methacrylates
  • Methylmethacrylates
  • Polymethacrylic Acids
  • Root Canal Filling Materials
  • Water
  • triethylene glycol dimethacrylate
  • Polyethylene Glycols