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Synthesis and characterization of antimicrobial dimethacrylates containing quaternary ammonium functionalities for dental and biomedical applications



Joseph M. Antonucci, Diana N. Zeiger, Sheng Lin-Gibson, Bruce O. Fowler, Nancy J. Lin


The widespread incidence of recurrent caries has resulted in the need for improved dental restorative materials, including effective antibacterial, polymeric dental materials. Compounds with quaternary ammonium groups are known to reduce bacterial growth and in the form of monomer have the potential to copolymerize with methacrylate monomers to provide antibacterial polymers for dental applications. In this study, the Menschutkin reaction was utilized to synthesize two ionic liquid dimethacrylate monomers containing quaternary ammonium functionalities (IDMA-1 and IDMA-2). The monomers were characterized and shown to be miscible with commonly used dental dimethacrylate monomers. For instance, the novel monomers had high miscibility in a 1:1 (by mass) blend of bisphenol A glycidyl methacrylate (BisGMA) and triethylene glycol dimethacrylate (TEGDMA) with minimal effects on the photoactivated resins’ viscosities. Incorporation of as little as 10 % (by mass) IDMA-1 into BisGMA:TEGDMA polymers significantly reduced surface coverage by Streptococcus mutans, while increasing the IDMA-1 concentration to 30 % (by mass) had no additional effect on bacterial coverage. Cytotoxicity to RAW 264.7 mouse macrophage-like cell line was present for polymers containing high IDMA-1 concentrations, with ≥ 20 % IDMA-1 significantly reducing cell density, viability, and enzymatic activity (formazan reduction). Only polymers with 10 % IDMA-1 had no reduction in cell viability or enzymatic activity, although cell density was reduced. Thus, as little as 10 % IDMA-1 is effective at reducing bacterial colonization without cytotoxicity to mammalian cells. These novel monomers show great potential for use in dental polymeric restorative and adhesive materials, and the Menschutkin reaction provides a facile means to conveniently synthesize these and other molecules with antimicrobial quaternary ammonium groups for application in dental and medical materials.


antimicrobial, dental polymers, bacterial colonization, cytotoxicity


Antonucci, J. , Zeiger, D. , Lin-Gibson, S. , Fowler, B. and Lin, N. (2011), Synthesis and characterization of antimicrobial dimethacrylates containing quaternary ammonium functionalities for dental and biomedical applications, Biomaterials, [online], (Accessed June 19, 2024)


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Created October 27, 2011, Updated November 10, 2018