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Synthesis, Purification and Characterization of Polymerizable Multifunctional Quaternary Ammonium Compounds



Ugochukwu C. Okeke, Chad R. Snyder, Stanislav A. Frukhtbeyn


Polymer-based resin composites are commonly used in dentistry as restorative materials or adhesives. However, repeated occurrence of secondary caries at the restoration site necessitates development of novel long-lasting antimicrobial agents that can be incorporated into such restorative materials. Polymerizable quaternary ammonium methacrylate salts have shown promising sustained antimicrobial activity against both Gram-positive and Gram-negative bacteria. Methacrylate analogs of quaternary ammonium salts functionalized with carboxylic (AMadh1 68.8 % yield, AMadh2 53.2 % yield) and methoxysilane (AMsil1 94.8 % yield, AMsil2 36.0 % yield) groups were synthesized via Menschutkin reaction. Fourier-transform infrared spectroscopy (FTIR), nuclear magnetic resonance spectroscopy (1H, 13C and 2D 1H-13C heteronuclear single quantum coherence (HSQC) NMR), mass spectrometry, thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) were utilized to validate structures and characterize thermal properties of novel multifunctional quaternary ammonium salts synthesized. The potential adhesive, coupling and antimicrobial properties of these multifunctional monomers encourage their further comprehensive evaluation in conventional and experimental copolymers and composites.


Quaternary ammonium salts, antimicrobial monomers, antibacterial dental materials, tooth caries inhibition, Menschutkin reaction, copolymers, composites, resins


Okeke, U. , Snyder, C. and Frukhtbeyn, S. (2019), Synthesis, Purification and Characterization of Polymerizable Multifunctional Quaternary Ammonium Compounds, Molecules, [online], (Accessed April 20, 2024)
Created April 12, 2019, Updated October 12, 2021