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Antibacterial cotton treated with N-halamine and quaternary ammonium salt

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Abstract

Quaternary ammonium salts and N-halamines are widely used as biocides in antimicrobial coatings, and have been extensively studied over the past two decades. In this work, 5,5-dimethyl-3-(3′-triethoxysilylpropyl)hydantoin (SPH), and 3-(trimethoxysilylpropyl) octadecyl dimethyl ammonium chloride (SPODA) were synthesized and coated onto cotton fibers using a pad-dry process (PD) and the traditional pad-dry-cure process (PDC). The coated cotton swatches were characterized by FT-IR and SEM. The quaternary ammonium salt showed a relatively lower inactivating bacteria efficacy than did the N-halamine compounds. The chlorinated swatches coated with both SPH and SPODA using the PD process could inactivate about 7 logs of the Staphylococci aureus within 5–10 min and 7 logs of Escherichia coli O157:H7 within 10–30 min, respectively. The addition of quats in N-halamine coatings improved antimicrobial activity against Gram-negative bacteria E. coli O157:H7. However, this result was not observed when the PDC process was applied in coatings because of the increasing hydrophobicity of the coated samples under high coating temperature.

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References

  • Badrossamay RM, Sun G (2008) Preparation of rechargeable biocidal polypropylene by reactive extrusion with diallylamino triazine. Eur Polym J 44:733–742

    Article  CAS  Google Scholar 

  • 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]. Biomater 27:4825–4830

    Article  CAS  Google Scholar 

  • Cerkez I, Kocer HB, Worley SD, Broughton RM, Huang TS (2011) N-halamine biocidal coatings via a layer-by-layer assembly technique. Langmuir 27:4091–4097

    Article  CAS  Google Scholar 

  • Cerkez I, Worley SD, Broughton RM, Huang TS (2013) Rechargeable antimicrobial coatings for poly(lactic acid) nonwoven fabrics. Polym 54:536–541

    Article  CAS  Google Scholar 

  • Chen Y, Worley SD, Huang TS, Weese J, Kim J, Wei CI, Williams JF (2004) Biocidal polystyrene beads. III. Comparison of N-halamine and quat functional groups. J Appl Polym Sci 92:363–367

    Article  CAS  Google Scholar 

  • Cheng L, Weir MD, Xu HHK, Antonucci JM, Kraigsley AM, Lin NJ, Lin-Gibson S, Zhou X (2012) Antibacterial amorphous calcium phosphate nanocomposites with a quaternary ammonium dimethacrylate and silver nanoparticles. Dent Mater 28:561–572

    Article  CAS  Google Scholar 

  • Hong KH, Liu N, Sun G (2009) UV-induced graft polymerization of acrylamide on cellulose by using immobilized benzophenone as a photo-initiator. Eur Polym J 45:2443–2449

    Article  CAS  Google Scholar 

  • Huang L, Sun X, Xiao YH, Dong Y, Ton ZC, Xing X, Li F, Chai ZG, Chen JH (2012) Antibacterial effect of a resin incorporating a novel polymerizable quaternary ammonium salt MAE-DB against Streptococcus mutans. J Biomed Mater Res 100B:1353–1358

    Article  CAS  Google Scholar 

  • Ioppolo JA, Kassiou M, Rendina LM (2009) Water-soluble phosphonium salts containing 1,12-dicarba-closo-dodecaborane(12). Tetrahedron Lett 50:6457–6461

    Article  CAS  Google Scholar 

  • Jin D, Fu S, Zhang F, Lu X, Han P (2012) Preparation of silica gel grafting bisquarternary phosphonium and its antibacterial activities. Asian J Chem 24:107–111

    CAS  Google Scholar 

  • Jincheng W, Xiaoyu Z, Wenli H, Nan X, Xingchen P (2012) Synthesis of hyper-branched quaternary ammonium salt and its application into montmorillonite. Powder Technol 221:80–89

    Article  Google Scholar 

  • Ju HY, Manju MD, Kim KH, Park SW, Park DW (2008) Catalytic performance of quaternary ammonium salts in the reaction of butyl glycidyl ether and carbon dioxide. J Ind Eng Chem 14:157–160

    Article  CAS  Google Scholar 

  • Kocer H, Cerkez I, Worley SD, Broughton RM, Huang TS (2011a) Cellulose/starch/HALS composite fibers extruded from an ionic liquid. Carbohydr Polym 86:922–927

    Article  CAS  Google Scholar 

  • Kocer HB, Worley SD, Broughton RM, Huang TS (2011b) A novel N-halamine acrylamide monomer and its copolymers for antimicrobial coatings. React Funct Polym 71:561–568

    Article  CAS  Google Scholar 

  • Kou L, Liang J, Ren X, Kocer HB, Worley SD, Broughton RM, Huang TS (2009a) Novel N-halamine silanes. Colloids Surf A 345:88–94

    Article  CAS  Google Scholar 

  • Kou L, Liang J, Ren X, Kocer HB, Worley SD, Tzou YM, Huang TS (2009b) Synthesis of a water-soluble siloxane copolymer and its application for antimicrobial coatings. Ind Eng Chem Res 48:6521–6526

    Article  CAS  Google Scholar 

  • Li J, Zhang Q, Wang Y, Zhang W, Li T (2012) Synthesis and properties of organosilicon quaternary salts surfactants. J Surfactants Deterg 15:339–344

    Article  CAS  Google Scholar 

  • Liang J, Wu R, Huang TS, Worley SD (2005) Polymerization of a hydantoinylsiloxane on particles of silicon dioxide to produce a biocidal sand. J Appl Polym Sci 97:1161–1166

    Article  CAS  Google Scholar 

  • Liang J, Chen Y, Barnes K, Wu R, Worley SD, Huang TS (2006) N-halamine/quat siloxane copolymers for use in biocidal coatings. Biomater 27:2495–2501

    Article  CAS  Google Scholar 

  • Liang J, Barnes K, Akdag A, Worley SD, Lee J, Broughton RM, Huang TS (2007) Improved antimicrobial siloxane. Ind Eng Chem Res 46:1861–1866

    Article  CAS  Google Scholar 

  • Liu S, Sun G (2008) Radical graft functional modification of cellulose with allyl monomers: chemistry and structure characterization. Carbohydr Polym 71:614–625

    Article  CAS  Google Scholar 

  • Lu G, Wu D, Fu R (2007) Studies on the synthesis and antibacterial activities of polymeric quaternary ammonium salts from dimethylaminoethyl methacrylate. React Funct Polym 67:355–366

    Article  CAS  Google Scholar 

  • Mukherjee I, Manna K, Dinda G, Ghosh S, Moulik SP (2012) Shear- and temperature-dependent viscosity behavior of two phosphonium-based ionic liquids and surfactant triton X-100 and their biocidal activities. J Chem Eng Data 57:1376–1386

    Article  CAS  Google Scholar 

  • Ren X, Kou L, Kocer HB, Zhu C, Worley SD, Broughton RM, Huang TS (2008a) Antimicrobial coating of an N-halamine biocidal monomer on cotton fibers via admicellar polymerization. Colloids Surf A 317:711–716

    Article  CAS  Google Scholar 

  • Ren X, Kou L, Liang J, Worley SD, Tzou YM, Huang TS (2008b) Antimicrobial efficacy and light stability of N-halamine siloxanes bound to cotton. Cellul 15:593–598

    Article  CAS  Google Scholar 

  • Ren X, Akdag A, Kocer HB, Worley SD, Broughton RM, Huang TS (2009) N-halamine-coated cotton for antimicrobial and detoxification applications. Carbohydr Polym 78:220–226

    Article  CAS  Google Scholar 

  • Simoncic B, Tomsic B, Cerne L, Orel B, Jerman I, Kovac J, Zerjav M, Simoncic A (2012) Multifunctional water and oil repellent and antimicrobial properties of finished cotton: influence of sol-gel finishing procedure. J Sol–Gel Sci Technol 61:340–354

    Article  CAS  Google Scholar 

  • Tischer M, Pradel G, Ohlsen K, Holzgrabe U (2012) Quaternary ammonium salts and their antimicrobial potential: targets or nonspecific interactions? ChemInform 7:22–31

    CAS  Google Scholar 

  • Wan W, Yeow JTW (2012) Antibacterial properties of poly(quaternary ammonium) modified gold and titanium dioxide nanoparticles. J Nanosci Nanotechnol 12:4601–4606

    Article  CAS  Google Scholar 

  • Weng Y, Guo X, Gregory RL, Xie D (2011) Preparation and evaluation of an antibacterial dental cement containing quaternary ammonium salts. J Appl Polym Sci 122:2542–2551

    Article  CAS  Google Scholar 

  • Williams JF, Suess J, Santiago J, Chen Y, Wang J, Wu R, Worley SD (2005) Antimicrobial properties of novel N-halamine siloxane coatings. Surf Coat Int 88:35–39

    Article  CAS  Google Scholar 

  • Worley SD, Chen Y, Wang JW, Wu R (2005) Novel N-halamine siloxane monomers and polymers for preparing biocidal coatings. Surf Coat Int 88:93–99

    Article  CAS  Google Scholar 

  • Wu T, Xie AG, Tan SZ, Cai X (2011) Antimicrobial effects of quaternary phosphonium salt intercalated clay minerals on Escherichia coli and Staphylococci aureus. Colloids Surf B 86:232–236

    Article  CAS  Google Scholar 

  • Yang G, Xie J, Hong F, Cao Z, Yang X (2012) Antimicrobial activity of silver nanoparticle impregnated bacterial cellulose membrane: effect of fermentation carbon sources of bacterial cellulose. Carbohydr Polym 87:839–845

    Article  CAS  Google Scholar 

  • Zhang Y, Ding M, Zhou L, Tan H, Li J, Xiao H, Li J, Snow J (2012) Synthesis and antibacterial characterization of gemini surfactant monomers and copolymers. Polym Chem 3:907–913

    Article  CAS  Google Scholar 

  • Zhao Q, Wang S, Muller-Steinhagen H (2004) Tailored surface free energy of membrane diffusers to minimize microbial adhesion. Appl Surf Sci 230:371–378

    Article  CAS  Google Scholar 

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Acknowledgments

The financial support was provided by the National Thousand Young Talents Program. The authors acknowledge helpful discussions with Dr. S.D. Worley (Auburn University).

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Authors and Affiliations

  1. Key Laboratory of Eco-textiles of Ministry of Education, College of Textiles and Clothing, Jiangnan University, Wuxi, 214122, Jiangsu, China

    Ying Liu, Kaikai Ma, Rong Li & Xuehong Ren

  2. Department of Poultry Science, Auburn University, Auburn, AL, 36849, USA

    T. S. Huang

Authors
  1. Ying Liu
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  2. Kaikai Ma
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  3. Rong Li
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  4. Xuehong Ren
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  5. T. S. Huang
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Correspondence to Xuehong Ren.

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Liu, Y., Ma, K., Li, R. et al. Antibacterial cotton treated with N-halamine and quaternary ammonium salt. Cellulose 20, 3123–3130 (2013). https://doi.org/10.1007/s10570-013-0056-7

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  • DOI: https://doi.org/10.1007/s10570-013-0056-7

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