Urushiol-Based Benzoxazine Containing Sulfobetaine Groups for Sustainable Marine Antifouling Applications

Abstract

Benzoxazine resins are new thermosetting resins with excellent thermal stability, mechanical properties, and a flexible molecular design, demonstrating promise for applications in marine antifouling coatings. However, designing a multifunctional green benzoxazine resin-derived antifouling coating that combines resistance to biological protein adhesion, a high antibacterial rate, and low algal adhesion is still challenging. In this study, a high-performance coating with a low environmental impact was synthesized using urushiol-based benzoxazine containing tertiary amines as the precursor, and a sulfobetaine moiety into the benzoxazine group was introduced. This sulfobetaine-functionalized urushiol-based polybenzoxazine coating (poly(U−ea/sb)) was capable of clearly killing marine biofouling bacteria adhered to the coating surface and significantly resisting protein attachment. poly(U−ea/sb) exhibited an antibacterial rate of 99.99% against common Gram negative bacteria (e.g., Escherichia coli and Vibrio alginolyticus) and Gram positive bacteria (e.g., Staphylococcus aureus and Bacillus sp.), with >99% its algal inhibition activity, and it effectively prevented microbial adherence. Here, a dual-function crosslinkable zwitterionic polymer, which used an “offensive-defensive” tactic to improve the antifouling characteristics of the coating was presented. This simple, economic, and feasible strategy provides new ideas for the development of green marine antifouling coating materials with excellent performance.

Sustainable Coating Based on Zwitterionic Functionalized Polyurushiol with Antifouling and Antibacterial Properties

“…Therefore, these results confirmed the successful synthesis of IPUDM, the precursor containing aminoethyl methacrylate and phenolic amide ester bonds. Furthermore, the FTIR spectrum of IPUDM-SB showed strong characteristic absorption peaks at 1166 and 1036 cm −1 , corresponding to the vibrational absorption peaks of the -SO 3 − groups, confirming the successful coupling of sulfobetaine glycine groups with the urushiol molecules [32].…”

“…The peaks at 399.9 and 399.8 eV corresponded to the unreacted tertiary amines on the IPUDM-SB and HUDM-SB coatings, respectively. The other peaks at 402.5 and 402.3 eV represented the quaternary ammonium ions (+NR 4 ) formed after the successful chemical grafting of 1,3-propane sulfone [32]. The quaternary ammonium ions required higher energy to displace electrons from their N1s orbitals due to their electron-deficient and more stable nature.…”

Design of Rectifiable Bio-based Polybenzoxazine for Stimulated Self-Healing and Shape Memory applications with antimicrobial activity

“…Numerous sustainable phenolic sources have been used for to synthesis a bio-based benzoxazine monomer such as eugenol [11], chavicol [20], vanillin [21,22], urushiol [23,24], resveratrol [25], guaiacol [26,27], cinnamic/cinnamates [28], coumarin [29], etc., The sustainable and recyclable benzoxazines, obtained from the abundant bio-waste with low cost of raw materials serve as excellent substitutes for synthetic monomer. The one of the bio-waste phenolic sources was cardanol and occurred from cashew nut shell consist of an unsaturated alkyl chain [30][31][32] and the presence of an unsaturated alkyl chain in cardanol was used to produce a variety of products [33,34].…”