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

Abstract

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.

Advancing coatings with polybenzoxazines: insights into molecular design, synthesis, and modification

“…Consequently, PBOZs exhibit low surface energy, stable hydrophobicity, antimicrobial properties, and excellent antiadhesion properties. 46…”

The mechanochemical synthesis of environmentally benign fully biobased 4th generation benzoxazines and their polymers: mechanistic insights into the catalytic activity of latent catalysts

“…47 Biomass-derived derivatives of phenols and amines have proven successful as renewable resources, offering excellent opportunities to synthesize sustainable polymers capable of partially or fully replacing petroleum-based PBZs. 22,25,30,34,48,49 Biobased PBZs have demonstrated their utility in several applications including high-performance anticorrosive coatings, 50 superparamagnetic materials, 51 cathode materials in next-generation batteries beyond Li-ions, 52,53 antibacterials, 54,55 and as potential flame-retardant materials. 36,56,57 Recently, the replacement of formaldehyde with other aldehydes has also been employed to form 4 th generation BZs.…”

Multistep Continuous Synthesis of a Highly Fluorescent Tröger’s Base-Derived Benzoxazine: Its Thermal Conversion into Intrinsic Microporosity Polymers

“…Recently, a benzoxazine-containing anthracene unit was synthesized and showcased green fluorescence with a fluorescence emission peak at 494 nm upon irradiation with UV light . The previously described benzoxazine monomers and polymers have been shown to have appealing characteristics, , consequently encouraging continuous efforts to discover and synthesize novel benzoxazine molecules.…”