Benzoxazine Monomers with Antibacterial Property and Polybenzoxazines for Preventing Adhesion to Bacteria

A series of biobased benzoxazine monomers (TF-BOZs) were designed and synthesized using tyrosine methyl ester, furfural, and five amine sources through the Mannich condensation reaction. The structures of BOZs were examined using 1 H NMR, 13 C NMR, mass spectra (MS), and Fourier transform infrared spectra (FT-IR), which indicated the successful synthesis of TF-BOZ monomers. Curing behavior was studied, which revealed that BOZ monomers could form polybenzoxazine resins (PBOZs) via ring-opening polymerization. In addition, the PBOZs exhibited remarkable thermal stability, which is better than that of the traditional bisphenol A–aniline polybenzoxazine. The antibacterial properties and antibiofilm performances of the BOZs were investigated. The TF-BOZs showed significant broad-spectrum antibacterial activity against Gram-positive Staphylococcus aureus ( S. aureus ), Gram-negative Escherichia coli ( E. coli ), and Pseudomonas aeruginosa ( P. aeruginosa ). The BOZ-Ola exhibited the best antibacterial property with the minimum inhibitory concentration (MIC) of 5 μg/mL against S. aureus, which, based on the electrostatic interaction acts on the bacterial surface and hydrophobic interaction destroys cell membrane integrity. Notably, PBOZs exhibited significant resistance to bacterial adhesion because of their antimicrobial properties, stable hydrophobicity, and low surface energy, indicating their application potential as antifouling materials. Those results indicate the great potential of TF-BOZs and PBOZs as antibacterial agents and materials to solve bacterial contamination and expand the application range of sustainable materials.