Novel mechanically strong and antibacterial dimethacrylate copolymers based on quaternary ammonium urethane-dimethacrylate analogues

Abstract

Objectives: This study assumed that the quaternary ammonium urethane-dimethacrylate derivative (QAUDMA-m, where m was 8, 10, 12, 14, 16, 18, and corresponded to the number of carbon atoms in the N-alkyl substituent) can be used to achieve copolymers with high mechanical performance and antibacterial activity.

Methods: Photocured copolymers of bisphenol A glycerolate dimethacrylate (Bis-GMA) 40 wt%, QAUDMA-m 40 wt%, and triethylene glycol dimethacrylate (TEGDMA) 20 wt% (BG:QAm:TEG) were characterized by the degree of conversion (DC), flexural strength (FS), flexural modulus (E), hardness (HB), and antibacterial properties (the number of bacteria colonies adhered to copolymer surfaces and inhibition zone diameter (IZD)) against Staphylococcus aureus and Escherichia coli. Reference copolymers of Bis-GMA, urethane-dimethacrylate monomer (UDMA), and TEGDMA (BG:TEG and BG:UD:TEG) were also characterized.

Results: The DC of BG:QAm:TEGs ranged from 0.59 to 0.68, HB from 83.84 to 153.91 MPa, FS from 50.81 to 74.47 MPa, and E from 1986.74 to 3716.68 MPa. The number of S. aureus and E. coli bacteria adhered to BG:QAm:TEG surfaces was from 0 (no bacteria observed) to 6.47 and 4.99 log(CFU/mL), respectively. IZD was from 10 and 5 mm (no inhibition zone) to 23 and 21 mm, respectively. Three copolymers: BG:QA8:TEG, BG:QA10:TEG, and BG:QA12:TEG had similar or better mechanical properties than the reference copolymers, but unlike them, they showed high antibacterial activity against both bacteria strains.

Significance: The obtained copolymers can offer a good, mechanically efficient, bioactive alternative to BG:TEG and BG:UD:TEG copolymers. The use of such materials can help to make progress in dental health care.

Keywords: Antibacterial activity; Dental materials; Mechanical properties; Quaternary ammonium compounds; Urethane-dimethacrylate monomers.