Synthesis of antibacterial methacrylate monomer derived from thiazole and its application in dental resin

• A new non-quaternary ammonium antibacterial methacrylate MEMT was synthesized.
• Novel dental resin with MEMT was prepared.
• MEMT can endow dental polymer with antibacterial activity.
• MEMT had no negative effect on FS and FM before water immersion.

A non-quaternary ammonium antibacterial methacrylate monomer MEMT derived from thiazole was synthesized and applied into UDMA/TEGDMA dental resin with a series of mass fraction (10 wt%, 20 wt%, and 30 wt%). Double bond conversion, polymerization shrinkage, water sorption, solubility, flexural strength and modulus, and antibacterial activity of MEMT containing resin formulations were investigated with UDMA/TEGDMA as control resin. The results showed that MEMT containing dental resin had higher double bond conversion than control resin. Compared with control polymer, all MEMT containing polymer had comparable or lower polymerization shrinkage, water sorption and solubility, except for the polymer with 30 wt% of MEMT which had higher water sorption and solubility than control polymer. The MEMT had no influence on flexural strength and modulus before water immersion, but all MEMT containing polymers had lower flexural strength and modulus than control polymer after water immersion. The MEMT could endow dental polymer with obvious antibacterial activity by immobilizing MEMT into the polymeric network.