Synthesis of Bio-Based Polybenzoxazine and Its Antibiofilm and Anticorrosive Activities

Abstract

Candida albicans are highly widespread pathogenic fungi in humans. Moreover, its developed biofilm causes serious clinical problems, leading to drug failure caused by its inherent drug tolerance. Hence, the inhibition of biofilm formation and virulence characteristics provide other means of addressing infections. Polymer composites (PCs) derived from natural products have attracted increasing interest in the scientific community, including antimicrobial applications. PCs are a good alternative approach to solving this challenge because of their excellent penetration power inside biofilms. The main objectives of this study were to synthesize a novel curcumin-based polybenzoxazine polymer composite (poly(Cu-A) PC) using Mannich condensation reaction and evaluate their potency as an antibiofilm and anticorrosive candidate against C. albicans. In addition, their anticorrosive efficacy was also explored. PC exhibited significant antibiofilm efficacy versus C. albicans DAY185 by the morphologic changing of yeast to hyphae, and>90% anticorrosive efficacy was observed at a higher dose of PC. These prepared PC were safe in vivo against Caenorhabditis elegans and Raphanus raphanistrum. The study shows that a polybenzoxazine polymer composite has the potential for controlling biofilm-associated fungal infections and virulence by C. albicans, and opens a new avenue for designing PCs as antifungal, anticorrosive agents for biofilm-associated fungal infections and industrial remediation.

Recent advances in bio-based polybenzoxazines as an interesting adhesive coating

“…Benzoxazine can be synthesized using a variety of methods, such as the Duff reaction (Scheme 4a) with phenol and hexamethylenetetramine, the reaction of a halogenated triazole with salicyl alcohol (Scheme 4b), and the cyclization procedure of methyl- ortho -tolyl ether with a primary amine (Scheme 4c). 34,41–43…”

“…It can also be synthesized under more reaction conditions compared to benzoxazines, resulting in various aromatic ring-fused oxazines with specific characteristics. 34,45–48…”

“…Due to the reactants' compatibility complexity, this cyclic addition approach is less common than others; however, it contributes to the diversity of the benzoxazine structure. 34,39,40…”

“…It can also be synthesized under more reaction conditions compared to benzoxazines, resulting in various aromatic ring-fused oxazines with specic characteristics. 34,[45][46][47][48] 3 Preparation and synthesis of biobased benzoxazine monomers Although there are many benzoxazine isomers (based on the location of the nitrogen and oxygen in the oxazine ring), as stated in the introduction, this section focuses mainly on synthesizing 1,3-benzoxazines because these compounds are typically employed for polymerization. There have been numerous published methods for synthesizing benzoxazine monomer structures.…”

Nature's empowerment: unraveling superior performance and green degradation closed-loop in self-curing fully bio-based benzoxazines

“…21 Numerous methods have been reported by previous researchers for the synthesis of bio-based benzoxazines. 22–26 However, in the realm of synthetic production processes, two prominent challenges have come to the fore. Firstly, the utilization of toxic catalysts poses a significant concern, casting a shadow over the environmental sustainability of these processes.…”