Development of direct contact-killing non-leaching antimicrobial polyurethanes through click chemistry

Polymer resins are critical for marine anti-biofouling coatings. In this study, degradable poly(ester-co-acrylate) with antifoulant pendant groups has been prepared by the radical ring-opening polymerization of 2-methylene-1,3dioxepane, methyl methacrylate, and N-methacryloyloxy methyl benzoisothiazolinone. Such a polymer containing main-chain esters can hydrolytically and enzymatically degrade. Both degradation rates increase with main-chain ester content. Moreover, since the antifoulant groups are chemically grafted to the degradable main chain, their release can be controlled by the degradation besides the hydrolysis of side groups. Our study shows that the copolymer coating is efficient in inhibiting the accumulation of marine bacterial biofilm of Pseudomonas sp. and diatom Navicular incerta. Marine field test reveals that the copolymer has excellent efficiency in preventing biofouling for more than 6 months.

Section: ■ Results and Discussionmentioning

confidence: 99%

“…for V-BIT and BIT-OH are ∼16 and ∼8 mg/L, respectively (Figure S3). Considering that the time scale in the antibacteria experiment is very short and the hydrolysis is so slow that the excellent antifouling ability is mainly attributed to contact-kill mechanism . In other words, the coating surfaces are active by contact.…”

Section: Resultsmentioning

confidence: 99%

Biodegradable Poly(ester-co-acrylate) with Antifoulant Pendant Groups for Marine Anti-Biofouling

Dai

Xie

et al. 2019

“…Marine biofouling, an undesirable colonization of marine organisms, has negative impacts on marine industries and marine activities. − Two strategies are generally employed to solve the problem: one involves killing the biofouling close to the surface (attacking), and the other involves resisting adhesion of the biofouling to the surface (defending). − Polymers containing antifouling groups such as quaternary ammonium salts, − phosphonium salts, − triclosan, − isothiazolinone, , and N -(2,4,6-trichlorophenyl) maleimide , have been used to prepare “attacking” coatings. The surface of these “attacking” coatings exhibits efficient bactericidal properties via release–killing or contact–killing.…”

Section: Introductionmentioning

confidence: 99%

Kill–Resist–Renew Trinity: Hyperbranched Polymer with Self-Regenerating Attack and Defense for Antifouling Coatings

Dai

Mei

et al. 2021

Traditional antifouling coatings are generally based on a single antifouling mechanism, which can hardly meet the needs of different occasions. Here, a single "kill−resist−renew trinity" polymeric coating integrating fouling killing, resistance, and releasing functions is reported. To achieve the design, a novel monomer-tertiary carboxybetaine ester acrylate with the antifouling group N-(2,4,6-trichlorophenyl)maleimide (TCB-TCPM) is synthesized and copolymerized with methacrylic anhydride via reversible addition-fragmentation chain transfer polymerization yielding a degradable hyperbranched polymer. Such a polymer at the surface/seawater is able to hydrolyze and degrade to short segments forming a dynamic surface (releasing). The hydrolysis of TCB-TCPM generates the antifouling groups TCPM (killing) and zwitterionic groups (resistance). Such a polymeric coating exhibits a controllable degradation rate, which increases with the degrees of branching. The antibacterial assay demonstrates that the antifouling ability arise from the synergistic effect of "attacking" and "defending". This study provides a new strategy to solve the challenging problem of marine biofouling.

“…Microbial infections in medical devices remain one of the major complications leading to high mortality. , Anti-infective biomaterials are considered to be a promising means for preventing infections associated with medical devices. − So far, various methods have been proposed to reduce the susceptibility of biomaterial surfaces to bacterial colonization and infection . As compared with leaching-based bactericidal surfaces, such as silver ions and antibiotics, nonleaching bactericidal materials kill bacteria on contact and thus avoid the gradual loss of antibacterial efficiency, eliminate environmental pollution, and alleviate bacterial resistance …”

Section: Introductionmentioning

confidence: 99%

“…3−5 So far, various methods have been proposed to reduce the susceptibility of biomaterial surfaces to bacterial colonization and infection. 6 As compared with leaching-based bactericidal surfaces, such as silver ions 7 and antibiotics, 8 nonleaching bactericidal materials kill bacteria on contact 9 and thus avoid the gradual loss of antibacterial efficiency, eliminate environmental pollution, and alleviate bacterial resistance. 10 Nonleaching bactericidal materials can be fabricated by immobilizing bactericidal components on the surface such as quaternary ammonium groups, 11 quaternary phosphonium groups, 12 antibacterial peptides, 13 lysozymes, 14 and chitosan derivatives.…”

Section: Introductionmentioning

confidence: 99%

Initiated Chemical Vapor Deposition of Graded Polymer Coatings Enabling Antibacterial, Antifouling, and Biocompatible Surfaces

Song

et al. 2020

We report initiated chemical vapor deposition of model-graded polymer coatings enabling antibacterial, antifouling, and biocompatible surfaces. The graded coating was constructed by a bottom layer consisting of bactericidal poly(dimethyl amino methyl styrene) and a surface layer consisting of both dimethyl amino methyl styrene (DMAMS) and hydrophilic vinyl pyrrolidone (VP) moieties. Fourier transform infrared spectra showed existence of both DMAMS and VP in the coating with DMAMS as the major component, while X-ray photoelectron spectroscopy analysis and water contact angle measurement revealed a VP-enriched coating surface. The resultant coating exhibited more than 99.9% killing rate against both Gram-negative Escherichia coli and Gram-positive Bacillus subtilis despite the incorporation of VP on the surface. We believe that such bactericidal capability resulted because of its high surface zeta potential, which could be originated from the DMAMS units distributed both on the top surface and underneath. The graded coating achieved more than 85% bacterial fouling resistance than the pristine substrate, as well as improved biocompatibility, owing to the abundant surface lactam groups from the VP moiety. Furthermore, the graded coating maintained good bactericidal capability after multicycle challenges of bacterial solutions and was durable against continuous rigorous washing, suggesting potential applications in biomedical devices.