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Ionic Liquid Dental Monomers Based on Quaternary Ammonium Salts

Objectives: To investigate the feasibility of synthesizing flowable ionic dimethacrylates (IDMA) based on the formation of quaternary ammonium salts, and to assess their miscibility with conventional dental monomers and antibacterial activity. Methods: Chemicals used in this study included: 2-bromoethyl methacrylate (BEMA), 2,2'-bis(bromomethyl)-1,1'-biphenyl (BbmBP), 2-(N,N-dimethylamino)ethyl methacrylate (DMAEMA), and anhydrous ethanol. The Menschutkin reaction, involving the nucleophilic reaction of a tertiary amine with a halogenated organic compound, was the synthetic method employed. All reactions were conducted in anhydrous ethanol maintained at 60 oC-80 oC for approximately 24 h. Products from the DMAEMA/BEMA reaction (IDMA-1) and the DMAEMA/BbmBP reaction (IDMA-3) were characterized by FT-IR and 1H NMR. Results: Equal molar amounts of DMAEMA and BEMA yielded a moderately viscous (shear viscosity = 0.91 ± 0.02 Pa s), colorless liquid (IDMA-1) that was easily miscible with common base dental resins (bis-GMA,UDMA,EBPADMA) as well as diluent monomers such as TEGDMA. DMAEMA and BbmBP in 2:1 molar ratio yielded a higher viscosity (shear viscosity = 9.83 ± 0.1), colorless liquid (IDMA-3) that was also compatible with the aforementioned dental monomers. FT-IR of both ionic liquid monomers showed the disappearance of the C-Br absorption bands (512 cm-1 to 604 cm-1) as well as the N(CH3)2 bands from DMAEMA (2822 cm-1, 2771 cm-1). 1H NMR confirmed the assigned chemical structures of IDMA-1 and IDMA-3. Various amounts (10 to 30 mass %) of IDMA-1 added to bis-GMA/TEGDMA (1:1 by mass) resin showed a regular but modest increase in viscosity with increasing concentration of IDMA-1. Bacterial growth (Streptococcus mutans) on IDMA-1 copolymers was reduced. Conclusions: The Menschutkin reaction provides a facile approach to a variety of potentially anti-microbial, cationic quaternary ammonium monomers, including ionic liquid monomers having excellent miscibility with dental resins. These novel monomers are expected to find utility in dental and biomedical applications. Support: NIDCR/NIST Interagency Agreement Y1-DE-7005-01.
Division: AADR/CADR Annual Meeting
Meeting: 2010 AADR/CADR Annual Meeting (Washington, D.C.)
Location: Washington, D.C.
Year: 2010
Final Presentation ID: 1026
Abstract Category|Abstract Category(s): Dental Materials 6: Polymer-based Materials-Chemistry and Composition
Authors
  • Antonucci, Joseph M.  ( National Institute of Standards and Technology, Gaithersburg, MD, USA )
  • Fowler, Bruce  ( National Institute of Standards and Technology, Gaithersburg, MD, USA )
  • Lin, Nancy J.  ( National Institute of Standards and Technology, Gaithersburg, MD, USA )
  • Zeiger, Diana N.  ( National Institute of Standards and Technology, Gaithersburg, MD, USA )
  • Lin-gibson, Sheng  ( National Institute of Standards and Technology, Gaithersburg, MD, USA )
    • SESSION INFORMATION
    Poster Session
    Synthesis and Polymerization of Resins and Ionomers
    03/05/2010