Synthesis and photopolymerizations of new crosslinkers for dental applications

Yagci B., Ayfer B., ZİYLAN A., Avci D.

MACROMOLECULAR MATERIALS AND ENGINEERING, vol.291, no.4, pp.336-344, 2006 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 291 Issue: 4
  • Publication Date: 2006
  • Doi Number: 10.1002/mame.200500391
  • Journal Name: MACROMOLECULAR MATERIALS AND ENGINEERING
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.336-344
  • Keywords: bis-GMA, crosslinking, dental polymers, alpha-hydroxymethacrylates, photopolymerization, LOW-SHRINKING COMPOSITES, MICHAEL-ADDITION, MONOMERS, DIMETHACRYLATE, POLYMERIZATION, KINETICS, METHACRYLATES, POLYMERS, MACROMONOMERS, SYSTEMS
  • Dokuz Eylül University Affiliated: No

Abstract

Five new crosslinkers for use in dental composites were synthesized. Four are based on TBHMA: 1 via reaction of TBBr and Bisphenol A; 2 by hydrolysis of t-butyl groups of the first monomer to give a diacid derivative; 3 by conversion of the first monomer to an amide derivative using benzyl amine; 4 by conversion of the first monomer to amide derivative using APTES. The AHM-based monomer 5 was synthesized from the Michael addition of APTES to AHM. The photopolymerization behaviors of the synthesized monomers with Bis-GMA, TEGDMA and HEMA were investigated using photodifferential scanning calorimetry at 40 degrees C using DMPA as photoinitiator. The polymerization rates and degrees of conversion for mixtures of any of the monomers 1-4 with Bis-GMA:TEGDMA were found to be similar to Bis-GMA:TEGDMA, higher than Bis-GMA:HEMA, and also higher than mixtures with Bis-GMA:HEMA. The incorporation of TBHMA-based monomers into the conventional resin mixture (Bis-GMA and TEGDMA) reduced the polymerization shrinkages. Monomer 5 and its mixtures polymerized much faster and to higher degrees of conversion than the other investigated systems, however, this system exhibited the largest volume shrinkage.