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Synthesis and characterization of potential multifunctional methacrylate-based dental monomers

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Abstract

We describe synthesis and characterization of a series of novel multifunctional methacrylate-based dental monomers. Triethanolamine was reacted with glycidyl methacrylate and methacryloyl chloride to produce a series of multifunctional methacrylate-end-capped compounds for conversion to quaternary ammonium fluoride monomers with decyl-substituted side-chain to afford antibacterial dental monomers. The chemical structure of all samples was characterized by Fourier-transform infrared and proton nuclear magnetic resonance (1H NMR) spectroscopies. The obtained monomers have potential to replace 2,2-bis[4-(2-hydroxy-3-methacryloyloxypropyl)phenyl]propane as base monomer of universal resin-based dental composites in presence of diluting monomer (e.g., triethylene glycol dimethacrylate) due to their multifunctionality as well as possible antibacterial activity.

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Acknowledgements

We wish to express our gratitude to the Research Center for Pharmaceutical Nanotechnology (RCPN), Tabriz University of Medical Sciences for financial support of this project (grant number: 93002, a part of Ph.D. thesis number: 93/002/131/4).

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Authors and Affiliations

  1. Research Center for Pharmaceutical Nanotechnology, Tabriz University of Medical Sciences, P.O. Box: 51656-65811, Tabriz, Iran

    Mehdi Jaymand, Mehrdad Lotfi & Jaleh Barar

  2. Department of Endodontics, Dental Faculty, Tabriz University of Medical Sciences, P.O. Box: 51666-14711, Tabriz, Iran

    Mehrdad Lotfi

  3. Department of Pharmaceutics, Faculty of Pharmacy, Tabriz University of Medical Sciences, P.O. Box: 14766-51664, Tabriz, Iran

    Jaleh Barar

  4. Department of Operative Dentistry, Dental Faculty, Tabriz University of Medical Sciences, P.O. Box: 51666-14711, Tabriz, Iran

    Soodabeh Kimyai

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  1. Mehdi Jaymand
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  2. Mehrdad Lotfi
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  4. Soodabeh Kimyai
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Correspondence to Mehdi Jaymand or Mehrdad Lotfi.

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Jaymand, M., Lotfi, M., Barar, J. et al. Synthesis and characterization of potential multifunctional methacrylate-based dental monomers. Res Chem Intermed 43, 5707–5722 (2017). https://doi.org/10.1007/s11164-017-2957-9

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  • DOI: https://doi.org/10.1007/s11164-017-2957-9

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