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 1H NMR, 13C 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.