Synthesis of an N-halamine monomer and its application in antimicrobial cellulose via an electron beam irradiation process

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• 作者：Xiaolin Li ; Yin Liu ; Zhiming Jiang ; Rong Li ; Xuehong Ren ; T. S. Huang
• 关键词：N ; halamine ; Cellulose ; Antimicrobial ; Electron beam
• 刊名：Cellulose
• 出版年：2015
• 出版时间：December 2015
• 年：2015
• 卷：22
• 期：6
• 页码：3609-3617
• 全文大小：564 KB
• 参考文献：Akdag A, Liang J, Worley SD (2007) Oxidation of organic sulfides by N-halamine compounds. Phosphorus Sulfur Silicon Relat Elem 182:1525-533CrossRef
  Alberti A, Bertini S, Gastaldi G, Iannaccone N, Macciantelli D, Torri G, Vismara E (2005) Electron beam irradiated textile cellulose fibres: ESR studies and derivatisation with glycidyl methacrylate (GMA). Eur Polym J 41:1787-797CrossRef
  Alonso D, Gimeno M, Olayo R, Vázquez-Torres H, Sepúlveda-Sánchez JD, Shirai K (2009) Cross-linking chitosan into UV-irradiated cellulose fibers for the preparation of antimicrobial-finished textiles. Carbohydr Polym 77:536-43CrossRef
  Barnes K, Liang J, Wu R, Worley SD, Lee J, Broughton RM, Huang TS (2006) Synthesis and antimicrobial applications of 5,5-ethylenebis [5-methyl-3-(3-triethoxysilylpropyl) hydantoin]. Biomaterials 27:4825-830CrossRef
  Cerkez I, Kocer HB, Worley SD, Broughton RM, Huang TS (2012) N-halamine copolymers for biocidal coatings. React Funct Polym 72:673-79CrossRef
  Chen Z, Sun Y (2006) N-Halamine-based antimicrobial additives for polymers: preparation, characterization, and antimicrobial activity. Ind Eng Chem Res 45:2634-640CrossRef
  Chen Y, Worley SD, Kim J et al (2003) Biocidal polystyrenehydantoin beads. 2. Control of chlorine loading. Ind Eng Chem Res 42:5715-720CrossRef
  Cheng X, Ma K, Li R, Ren X, Huang TS (2014) Antimicrobial coating of modified chitosan onto cotton fabrics. Appl Surf Sci 309:138-43CrossRef
  Choi HY, Han SO, Lee JS (2008) Surface morphological, mechanical and thermal characterization of electron beam irradiated fibers. Appl Surf Sci 255:2466-473CrossRef
  Dietrich J, Hirt P, Herlinger H (1996) Electron-beam-induced cyclisation to obtain C-fibre precursors from polyacrylonitrile homopolymers. Eur Polym J 32:617-23CrossRef
  Driscoll M, Stipanovic A, Winter W et al (2009) Electron beam irradiation of cellulose. Radiat Phys Chem 78:539-42CrossRef
  Du WL, Niu SS, Xu YL, Xu ZR, Fan CL (2009) Antibacterial activity of chitosan tripolyphosphate nanoparticles loaded with various metal ions. Carbohydr Polym 75:385-89CrossRef
  El-Naggar AWM, Zohdy MH, Said HM, El-Din MS, Noval DM (2005) Pigment colors printing on cotton fabrics by surface coating induced by electron beam and thermal curing. Appl Surf Sci 241:420-30CrossRef
  El-Tahlawy KF, El-Bendary MA, Elhendawy AG, Hudson SM (2005) The antimicrobial activity of cotton fabrics treated with different crosslinking agents and chitosan. Carbohydr Polym 60:421-30CrossRef
  Fu X, Shen Y, Jiang X, Huang D, Yan Y (2011) Chitosan derivatives with dual-antibacterial functional groups for antimicrobial finishing of cotton fabrics. Carbohydr Polym 85:221-27CrossRef
  Grunzinger SJ, Kurt P, Brunson KM, Wood L, Ohman DE, Wynne KJ (2007) Biocidal activity of hydantoin-containing polyurethane polymeric surface modifiers. Polymer 48:4653-662CrossRef
  Heidenau F, Mittelmeier W, Detsch R, Haenle M, Stenzel F, Ziegler G, Gollwitzer H (2005) A novel antibacterial titania coating: metal ion toxicity and in vitro surface colonization. J Mater Sci Mater Med 16:883-88CrossRef
  Kenawy ER, Abdel-Hay FI, El-Magd AA, Mahmoud Y (2006) Biologically active polymers: VII. Synthesis and antimicrobial activity of some crosslinked copolymers with quaternary ammonium and phosphonium groups. React Funct Polym 66:419-29CrossRef
  Kenawy ER, Abdel-Hay FI, El-Shanshoury AERR, El-Newehy MH (1998) Biologically active polymers: synthesis and antimicrobial activity of modified glycidyl methacrylate polymers having a quaternary ammonium and phosphonium groups. J Controlled Release 50:145-52CrossRef
  Klaykruayat B, Siralertmukul K, Srikulkit K (2010) Chemical modification of chitosan with cationic hyperbranched dendritic polyamidoamine and its antimicrobial activity on cotton fabric. Carbohydr Polym 80:197-07CrossRef
  Kocer HB, Akdag A, Ren X, Broughton RM, Worley SD, Huang TS (2008) Effect of alkyl derivatization on several properties of N-halamine antimicrobial siloxane coatings. Ind Eng Chem Res 47:7558-563CrossRef
  Kocer HB, Akdag A, Worley SD, Acevedo O, Broughton RM, Wu Y (2010a) Mechanism of photolytic decomposition of N-halamine antimicrobial siloxane coatings. ACS Appl Mater Interfaces 2:2456-464CrossRef
  Kocer HB, Cerkez I, Worley SD, Broughton RM, Huang TS (2011a) Polymeric antimicrobial N-halamine epoxides. ACS Appl Mater Interfaces 3:2845-850CrossRef
  Kocer HB, Cerkez I, Worley SD, Broughton RM, Huang TS (2011b) N-halamine copolymers for use in antimicrobial paints. ACS Appl Mater Interfaces 3:3189-194CrossRef
  Kocer HB, Worley SD, Broughton RM, Acevedo O, Huang TS (2010b) Effect of phenyl derivatization on the stabilities of antimicrobial N-chlorohydantoin derivatives. Ind Eng Chem Res 49:11188-1194CrossRef
  Kocer HB, Worley SD, Broughton RM, Huang TS (2011c) A novel N-halamine acrylamide monomer and its copolymers for antimicrobial coatings. React Funct Polym 71:561-68CrossRe
• 作者单位：Xiaolin Li (1)
  Yin Liu (1)
  Zhiming Jiang (1)
  Rong Li (1)
  Xuehong Ren (1)
  T. S. Huang (2)
  
  1. Key Laboratory of Eco-textiles of Ministry of Education, College of Textiles and Clothing, Jiangnan University, Wuxi, Jiangsu, 214122, China
  2. Department of Poultry Science, Auburn University, Auburn, AL, 36849, USA
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Bioorganic Chemistry
  Physical Chemistry
  Organic Chemistry
  Polymer Sciences
  
• 出版者：Springer Netherlands
• ISSN：1572-882X

文摘

N-halamine derivatives are efficient antibacterial agents and have been widely used in different kinds of surfaces due to their biocidal functions against a broad range of microorganisms, long term stabilities and regenerable properties. In this study, 3-(3-acrylicacidpropylester)-5,5-dimethylhydantoin was synthesized and bonded onto cotton fabric by an electron beam irradiation process. Upon exposure to household bleach, the coated cotton sample could be rendered antibacterial. SEM, FTIR and EDX were used to characterize the surface of modified cotton which confirmed that the N-halamine precursor was coated on the cotton successfully. The chlorinated cotton samples were challenged with Staphylococcus aureus and Escherichia coli O157:H7 and showed excellent biocidal efficacy by inactivating 100 % of the bacteria with the contact times of 10 and 5 min, respectively. Standard washing and UV irradiation tests demonstrated that the coated cotton presented remarkable regenerable properties. The tensile loss was about 20 %, which is in an acceptable range in antimicrobial finishing. Keywords N-halamine Cellulose Antimicrobial Electron beam