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CELLULOSE · 2024 ·Vol. 31 ·期 8 ·5263-5280 · IF 4.9

Quat/malonylurea-based N-chloramine silane crosslinked on cotton for bactericidal synergism

Han Qiuxia,Xu Yanmeng,Zhao Qian,Wang Shiwei,Zhang Chunzhe,Zhang Qiang,Wang Fei,Bai Yu,Chen Yong

The study reports a tactic for superior antibacterial performance on cotton via synergism of complementary functionalities of quaternary ammonium salt and malonylurea-based N -chloramine combined in a silane. Knoevenagel Condensation between 4-(chloromethyl)benzaldehyde and malonylurea formed a product whose chloromethyl group was used to quaternize tertiary amine of N , N -dimethylethanolamine. The O − H of the quaternization product was subsequently alcoholyzed with Si − H of trimethoxysilane. The methoxysilyl groups of the alcoholysis silane were hydrolyzed to silanol ones that condensed with either their own kind or hydroxy groups of cellulose to polymerize into a crosslinked polysiloxane finishing on cotton. Upon chlorination of malonylurea-based N − H bonds, each repeating unit of the polysiloxane has one quaternary ammonium salt and two imide N -chloramine sites. Antibacterial assays against Staphylococcus aureus and Escherichia coli proved that the synergism of quaternary ammonium salt and N -chloramine, a higher efficacy and a broader spectrum arising from their complementary elimination mechanisms and physiochemical features. Biocidal stability and rechargeability of the polysiloxane finishing were both promising due to the robust and hydrophobicity of silicone backbone and the sturdy cyclic N -chloramine. This research presented a general approach for generation of super biocidability on substrates that can react with hydroxy group using silanes to carry complementary functionalities. Graphical abstract

研究领域: 材料科学 · 纺织工程 · 生物医学
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JOURNAL OF MEMBRANE SCIENCE · 2023 · IF 9.5

Synergistically enhancing the antibacterial and antibiofilm activities of anion exchange membrane by chemically assembling gentamicin and N-chloramine layers

Yuyang Yao,Yan Zhang,Yundi Dong,Keqin Ruan,Yifei Shao,Geting Xu,Junbin Liao,Zhenlu Shen,Jiangnan Shen

Biofouling is one of significant obstacles decaying the high separation performance and long-term stability of polymer membranes during the application. To explore the desirable anti-biofouling anion exchange membrane (AEM), in this work, a series of modified AEMs having surface antibacterial functional layers on surface has been prepared by using gentamicin and N-chloramine for electrodialysis (ED). The antibacterial functional layer on surface was constructed via chemical assembly. By using CuSO 4 and H 2 O 2 as the trigger, l -dopa was oxidized on surface of commercial AEM (Fuji type II) to form a carboxyl layer. Thereafter, gentamicin was chemically assembled via the amide condensation reaction . It was chlorinated with diluted NaClO solution to endow it with synergistic antibacterial activity by using gentamicin. Investigation demonstrates that the optimized membrane of P( l -Dopa)@GM-Cl has high antibacterial activity against Staphylococcus aureus (S. aureus) and Escherichia coli (E. coli). Among them, flow cytometry shows that the antibacterial rate of P( l -Dopa)@GM-Cl against E. coli is more than 99%, which is much higher than original membrane (28.4%). P( l -Dopa)@GM-Cl exhibits the enhanced performance in inhibiting biofilm observed by scanning electron microscopy analysis . This work may provide a reference for the construction of anti-biofouling ion exchange membrane.

研究领域: 材料科学 · 微生物学 · 环境工程
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Canadian Journal of Chemistry · 2018 ·Vol. 96 ·期 10 · IF 1.084

Novel N-chloramine precursors for antimicrobial application: synthesis and facile covalent immobilization on polyurethane surface based on perfluorophenyl azide (PFPA) chemistry

Lingdong Li,Fengxiang Zhang,Fangyuan Gai,Hao Zhou,Xiaofang Chi,Hande Wang,Zongbao Zhao (Kent)

To control the pathogen cross contaminations on medical material surface, there is a pressing need to develop antimicrobial materials with highly efficacious surface biocidal activity. In this work, N-chloramine precursors containing a quaternary ammonium unit and perfluorophenyl azide unit were synthesized and covalently immobilized on inert polyurethane (PU) film upon UV light irradiation. The surface modification was confirmed by contact angle, Fourier transform infrared (ATR FTIR) spectroscopy, X-ray photoelectron spectroscopy (XPS), and atomic force microscopy (AFM) analyses. After bleaching treatment, satisfactory biocidal activity was achieved for the surface-modified PU films. It was found that the introduced surface QA center contributed an even faster surface contact killing behavior and that precursors with a longer structural linker caused higher surface chlorine content and higher antimicrobial efficacy. This approach provides a novel and facile method that enables the covalent immobilization of N-chloramine precursors on inert polymeric surface to produce durable antimicrobial materials.

研究领域: 材料科学 · 生物医学工程
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INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH · 2017 · IF 2.843

Interpenetration of Polyethylene Terephthalate with Biocidal Quaternary Ammonium/N-Chloramine Polysiloxane in Supercritical CO2

Yong Chen,Panwei Yu,Guoyuan Ren,Qiang Zhang,Qiuxia Han,Hongni Teng

Antibacterial modification of polymers with potent biocides via an efficient and universal approach is very desirable in both academia and industry. A polysiloxane with both quaternary ammonium and N-chloramine was prepared via a facile three-step synthetic route. Poly(methylhydrosiloxane) (PMHS) was first reacted with 2-(dimethylamino)ethyl acrylate to introduce an ending tertiary amine that was subsequently quaternized with 3-(3-chloropropyl)-5,5-dimethylhydantoin (CPDMH). The 5,5-dimethylhydantoin moiety was then transformed into its N-chloramine counterparts by chlorination with tert-butyl hypochlorite to produce quaternary ammonium (quat)/N-chloramine polysiloxane. The CO2-philic quat/N-chloramine polysiloxane was interpenetrated into polyethylene terephthalate (PET) in supercritical carbon dioxide (scCO2) and formed a 70 nm biocidal layer. The synthetic procedures and interpenetration results were characterized with Fourier transform infrared spectroscopy (FTIR), 1H NMR, scanning electron microscopy (SEM), and X-ray photoelectron spectrocsopy (XPS). The incorporation of quaternary ammonium and N-chloramine exhibited improved synergetic biocidal performance against Staphylococcus aureus and Escherichia coli, providing a complete kill of a 7-log reduction of both species within a contact time of 10 min. The polysiloxane interpenetration layer was stable and the rechargeability of lost chlorine was good when the layer was subjected to repeated washing, storage, and UV irradiation. This modification procedure uses ecologically responsible CO2 as solvent and is expected to be applicable to substrates of other chemistry since it does not rely on chemical linkage.

研究领域: 材料科学 · 生物医学工程
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JOURNAL OF COLLOID AND INTERFACE SCIENCE · 2019 · IF 6.361

Renewable antibacterial and antifouling polysulfone membranes incorporating a PEO-grafted amphiphilic polymer and N-chloramine functional groups

Shuhua Hou,Xiaojia Wang,Xue Dong,Jifu Zheng,Shenghai Li

Functionalized polysulfone (PSf) membranes with combined antibacterial and antifouling properties were fabricated by incorporating a poly(ethyleneoxide)-grafted (PEO-grafted) amphiliic polymer. Both antifouling and antibacterial groups were easily introduced onto the membrane surfaces through non-solvent induced phase separon process and a simple chlorination process. It was observed that the functionalized membranes were effectivatie in resisting both protein absorption and bacterial adhesion. Furthermore, the functionalized membrane ( M3-Cl ) showed mostly suppressed irreversible flux decline and a 97% flux recovery ratio after simple washing during the separation process, indicating excellent antifouling properties. Meanwhile, the functionalized PSf membrane exhibited efficient biocidal activity against E. coli and S. aureus . These modified functionalized PSf membranes also displayed outstanding properties in inhibiting the formation of biofilm . Moreover, the antibacterial feature was renewable by a simple process.

CAS / MDL: 7681-52-9 872-50-4
研究领域: 材料科学 · 生物医学工程
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Advanced Science · 2023 ·Vol. 10 ·期 30 ·2303588 · IF 15.1

Rechargeable Multifunctional Anti-Bacterial AEMs for Electrodialysis: Improving Anti-Biological Performance via Synergistic Antibacterial Mechanism

Yuyang Yao,Junjie Mu,Yuan Li,Yanjing Ma,Jingwen Xu,Yuna Shi,Junbin Liao,Zhenlu Shen,Jiangnan Shen

Constructing a functional layer on the surface of commercial membrane (as a substrate) to inhibit the formation of biofilms is an efficient strategy to prepare an antibacterial anion exchange membrane (AEM). Herein, a rechargeable multifunctional anti-biological system is reported by utilizing the mussel-inspired L-dopa connection function on commercial AEMs. Cobalt nanoparticles (Co NPs) and N-chloramine compounds are deposited on the AEM surface by a two-step modification procedure. The anti-biofouling abilities of the membranes are qualitatively and quantitatively analyzed by adopting common Gram-negative ( E. coli ) and Gram-positive ( S. aureus & Bacillus ) bacteria as model biofouling organisms. The optimized membrane exhibits a high stability concerning the NaCl solution separation performance within 240 min. Meantime, the mechanism of the anti-adhesion is un-veiled at an atomic level and molecular dynamics (MD) simulation are conducted to measure the interaction, adsorption energy and average loading by using lipopolysaccharide (LPS) of E. coli . In view of the superior performance of antibacterial surfaces, it is believed that this work could provide a valuable guideline for the design of membrane materials with resistance to biological contamination.

研究领域: 材料科学 · 生物学 · 环境工程
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CELLULOSE · 2023 ·Vol. 30 ·期 16 ·10519-10531 · IF 5.7

Synthesis and antibacterial activity of Schiff base-pyridine quaternary ammonium salt-halamine compounds on cotton fabrics

Tang Xin,Zhang Zaixing,Jing Lingxiao,Luan Kun,Zhou Sha,Zhang Tonghua

The incorporation of a single antimicrobial agent on textiles has been proven to be effective to enhance the antibacterial efficacy against single bacteria family. However, the daily usage of textile products face challenges from multiple microbes, i.e., bacterial, fungal, or/and viral, which threaten human’s safety and health. A “combination” of antimicrobial agents could be efficient and accessible to against several microbes at one time. In this study, a Schiff base-pyridinium quaternary ammonium salt-halamine precursor compound (E)-3-(((2,4-dioxoimidazolidin-1-yl)imino)methyl)pyridin-1-ium (4-DMPY) was synthesized and grafted onto MPTES-treated cotton fabric by thiol-ene click chemistry. The results of NRM, FTIR, Raman, EDX, XPS and SEM tests showed that 4-DMPY was synthesized and grafted onto cotton fabrics. The antibacterial test results showed that 4-DMPY had antibacterial activity against both  Staphylococcus aureus and Escherichia coli . The antibacterial activity of 4-DMPY-finished cotton fabric was significantly enhanced after chlorination treatment, which could kill 98% of S. aureus and 98.9% of E. coli at a concentration of 5 g/L, confirming the enhanced synergistic effect between 4-DMPY and N -chloramine. The antimicrobial substance on the cotton fabric is non-soluble, which kills 98.4% E. coli and 98.3% S. aureus within 1 min by a direct contact. In addition, the produced fabric retained 81% and 63% of active chlorine content after 30 washes and 30 days of storage, indicating a good antimicrobial durability. Herein, we anticipate the technology can be used to enhance antibacterial function of cellulose products and thus resist the potential threats from microbes to ensure human’s health.

研究领域: 材料科学 · 纺织工程 · 微生物学
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CELLULOSE · 2019 ·Vol. 26 ·期 8 ·5033-5049 · IF 3.917

Construction of pyridinium/N-chloramine polysiloxane on cellulose for synergistic biocidal application

Chen Yong,Ma Yijia,He Qingkun,Han Qiuxia,Zhang Qiang,Chen Qi

Abstract Cotton cellulose was modified with polysiloxane with dual antimicrobial groups of pyridinium and N -chloramine (N-Cl) to endorse enhanced synergistic biocidal ability. A new compound, 4-oxo- N -(pyridin-4-yl)pentanamide (OPPA), that contains precursors of both pyridinium and N -chloramine was synthesized via amidation of 4-oxopentanoic acid and 4-aminopyridine. The molecules of OPPA were connected to cotton cellulose using poly(methylhydrosiloxane) (PMHS) as linker through hydrosilylation reaction between some Si–H groups of PMHS and hydroxyl groups of cellulose and some other Si–H groups and ketone carbonyl groups of OPPA. The OPPA on cellulose was transformed into its biocidal counterpart after quaternization of the pyridine to pyridinium and chlorination of the amide N–H to N -chloramine. The synthetic procedures and modification results were characterized with Fourier-transform infrared spectroscopy, scanning electron microscopy (SEM), and X-ray photoelectron spectroscopy. The pyridinium/ N -chloramine polysiloxane layer on cellulose was estimated to be 77 nm by weight and provided powerful and synergistic antibacterial capacities against model species of Escherichia coli and Staphylococcus aureus . The stability of the polysiloxane modifier layer and the rechargeability of lost chlorine were promising under repeated washing, long-term storage, and UV irradiation. The presented pyridinium/ N -chloramine polysiloxane layer showed advantages over many of the current systems containing either cationic salt or N -chloramine due to the synergism. Graphical abstract

研究领域: 材料科学 · 化学 · 生物技术 · 微生物学
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