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

A series of biobased benzoxazine monomers (TF-BOZs) weredesignedand synthesized using tyrosine methyl ester, furfural, and five aminesources through the Mannich condensation reaction. The structuresof BOZs were examined using H-1 NMR, C-13 NMR,mass spectra (MS), and Fourier transform infrared spectra (FT-IR),which indicated the successful synthesis of TF-BOZ monomers. Curingbehavior was studied, which revealed that BOZ monomers could formpolybenzoxazine resins (PBOZs) via ring-opening polymerization. Inaddition, the PBOZs exhibited remarkable thermal stability, whichis better than that of the traditional bisphenol A-anilinepolybenzoxazine. The antibacterial properties and antibiofilm performancesof the BOZs were investigated. The TF-BOZs showed significant broad-spectrumantibacterial activity against Gram-positive Staphylococcusaureus (S. aureus),Gram-negative Escherichia coli (E. coli), and Pseudomonas aeruginosa (P. aeruginosa). The BOZ-Ola exhibitedthe best antibacterial property with the minimum inhibitory concentration(MIC) of 5 & mu;g/mL against S. aureus, which, based on the electrostatic interaction acts on the bacterialsurface and hydrophobic interaction destroys cell membrane integrity.Notably, PBOZs exhibited significant resistance to bacterial adhesionbecause of their antimicrobial properties, stable hydrophobicity,and low surface energy, indicating their application potential asantifouling materials. Those results indicate the great potentialof TF-BOZs and PBOZs as antibacterial agents and materials to solvebacterial contamination and expand the application range of sustainablematerials.