Synthesis, Purification and Characterization of Polymerizable Multifunctional Quaternary Ammonium Compounds

Molecules. 2019 Apr 13;24(8):1464. doi: 10.3390/molecules24081464.


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 the 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.

Keywords: Menschutkin reaction; antibacterial dental materials; antimicrobial monomers; composites; copolymers; quaternary ammonium salts; resins; tooth caries inhibition.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry*
  • Methacrylates / chemistry*
  • Polymerization*
  • Quaternary Ammonium Compounds / chemical synthesis*
  • Quaternary Ammonium Compounds / chemistry*


  • Anti-Bacterial Agents
  • Methacrylates
  • Quaternary Ammonium Compounds