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High-efficacy antimicrobial cellulose grafted by a novel quaternarized N-halamine

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Abstract

A novel quaternarized N-halamine precursor (3-chloro-2-hydroxypropyl)-(5, 5-dimethylhydantoinyl-1-ylmethyl)-dimethylammonium chloride (CDDAC), has been synthesized by a very facile two-step reaction. The two-step synthesis of CDDAC occurred at room temperature with common reactors, so the production of CDDAC could be easily enlarged to an industrial scale. Without any work-up, the final reaction solution which contained CDDAC could be directly used as grafting solution. CDDAC could be effectively grafted onto the surface of cellulose by a dehydrochlorination reaction. CDDAC grafted on cellulose was converted to N-halamine structure which showed powerful antimicrobial property by a chlorination reaction in the diluted NaClO solution. The antimicrobial tests showed that the chlorinated cellulose grafted with CDDAC was capable of 5-log inactivation of S. aureus and E. coli within 5 min. Also, the washing durability and storage stability of chlorinated cellulose grafted with CDDAC were investigated.

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References

  • Badrossamay MR, Sun G (2009) A study on melt grafting of N-halamine moieties onto polyethylene and their antibacterial activities. Macromolecules 42:1948–1954

    Article  CAS  Google Scholar 

  • Barnes K, Liang J, Worley SD, Lee J, Broughton RM, Huang TS (2007) Modification of silica gel, cellulose, and polyurethane with a sterically hindered N-halamine moiety to produce antimicrobial activity. J Appl Polym Sci 105:2306–2313

    Article  CAS  Google Scholar 

  • Cao ZB, Sun YY (2009) Polymeric N-halamine latex emulsions for use in antimicrobial paints. ACS Appl Mater Interfaces 1:494–504

    Article  CAS  Google Scholar 

  • Cerkez I, Kocer HB, Worley SD, Broughton RM, Huang TS (2012) Epoxide tethering of polymeric N-halamine moieties. Cellulose 19:959–966

    Article  CAS  Google Scholar 

  • Deavenport JL, Lopez BI (1995) Process for preparation of (halohydroxypropyl) trialkylammonium halides by quaternization of trialkylamines with epihalohydrins.US 5463127

  • Glenn JK, Gold MH (1983) Decolorization of several polymeric dyes by the ligniN-degrading basidiomycete phanerochaete chrysosporium. Appl Environ Microbiol 45:1741–1747

    CAS  Google Scholar 

  • Hazziza-Laskar JN, Helary G, Sauvet G (1993) Biocidal polymers active by contact. I. Synthesis of polybutadiene with pendant quaternary ammonium groups. J Appl Polym Sci 50:651–662

    Article  CAS  Google Scholar 

  • Jia ZS, Shen DF, Xu WL (2001) Synthesis and antibacterial activities of quaternary ammonium salt of chitosan. Carbohydr Res 333:1–6

    Article  CAS  Google Scholar 

  • Jung N, Han JS, Yeun SH, Chen XH (1998) Process for preparation of quaternary ammoniate containing organosilane group. KR 142146 B1

  • Kim YH, Sun G (2001) Durable antimicrobial finishing of nylon fabrics with acid dyes and a quaternary ammonium salt. Text Res J 71:318–323

    Article  CAS  Google Scholar 

  • Kocer HB, Cerkez I, Worley SD, Broughton RM, Huang TS (2011) N-Halamine copolymers for use in antimicrobial paints. Appl Mater Interfaces 3:3189–3194

    Article  CAS  Google Scholar 

  • Korotkii YV, Vrynchanu NA, Maksimov YN, Lozinskii MO (2011) Synthesis and antimicrobial and antifungal activities of quaternary salt of adamantine-containing alkoxydialkylaminopropanols. Pharm Chem J 45:19–21

    Article  CAS  Google Scholar 

  • Kotek R, Ola SMAE, White WC, Hauser P (2001) Polymerization of silane quaternary ammonium salts on fibers. Polym Prepr 42:106–107

    CAS  Google Scholar 

  • Liang J, Owens JR, Huang TS, Worley SD (2006) Biocidal hydantoinylsiloxane polymers IV. N-halamine siloxane functionalized silica gel. J Appl Polym Sci 101:3448–3454

    Article  CAS  Google Scholar 

  • Liang J, Chen YJ, Ren XH, Wu R, Barnes K, Worley SD (2007) Fabric treated with antimicrobial N-halamine epoxides. Ind Eng Chem Res 46:6425–6429

    Article  CAS  Google Scholar 

  • Mo ZL (2010) Synthesis method of epoxypropyltrimethylammonium chloride. CN101648927

  • Omar AK (2010) Evaluating the combined efficacy of polymers with fungicides for protection of museum textiles against fungal deterioration in Egypt. Pol J Microbiol 59:271–280

    Google Scholar 

  • Phugare SS, Kagalkar AN, Govindwar SP, Jadhav JP (2011) A study on significant microbial interaction leading to decolorization and degradation of textile dye Rubine 3GP. J Basic Microbiol 51:499–514

    Article  CAS  Google Scholar 

  • Pi ZB (2012) Environmentally-friendly antibacterial textile especially suitable suitable for next-to-skin clothing. CN 102433736 A

  • Qian L, Sun G (2003) Durable and regenerable antimicrobial t extiles: synthesis and applications of 3-ethylol-2,2,5,5-tetramethylimidazolidiN-1-one (TMIO) J]. J Appl Polym Sci 89:2418–2425

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  • Sakla AB, Abu-Taleb SA (1973) Individual microdetermination of chlorine, bromine and iodine in halogenated organic compounds by the oxygeN-flask method. Talanta 20:1332–1334

    Article  CAS  Google Scholar 

  • Sharif S, Ahmad S (2008) Synthesis and spectroscopic characterisation of 2,3-epoxy/3-chloro-2-hydroxy propyl derivatives of quaternary ammonium salts: useful cationic fixing agents. Chin J Chem 26:553–559

    Article  CAS  Google Scholar 

  • Slaughter S, Hayden MK, Nathan C, Hu TC, Rice T, Van VJ, Matushek M, Franklin C, Weinstein RA (1996) A comparison of the effect of universal use of gloves and gowns with that of glove use alone on acquisition of vancomyci N-resistant enterococci in a medical intensive care unit. Ann Intern Med 125:448

    CAS  Google Scholar 

  • Sun G, Xu XJ, Bickett JR, Williams JF (2001) Durable and regenerable antibacterial finishing of fabrics with a new hydantoin derivative. Ind Eng Chem Res 40:1016–1021

    Article  CAS  Google Scholar 

  • Tan KT, Obendorf SK (2007) Development of an antimicrobial microporous polyurethane membrane. J Membr Sci 289:199–209

    Article  CAS  Google Scholar 

  • Thomas R, Olivier L (2006) General and environmentally friendly synthesis of heterocyclic multidentate molecules based on microwave-assisted heating protocol. Tetrahedron 62:155–159

    Article  Google Scholar 

  • Weng YM, 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 

  • Worley SD, Chen YJ (2005) Preparation of biocidal crosslinked polystyrene particles containing hydantoin groups. US6852312 B2

  • Yang HF, Ren RS, Li ZF (2011) Preparation and antibacterial properties of nano-hydroxyapatite/quaternary ammonium sait composite material. Appl Mech Mater 71–78:830–832

    Article  Google Scholar 

  • Yeo SY, Lee HJ, Jeong SH (2003) Preparation of nanocomposite fibers for permanent antibacterial effect. J Mater Sci 38:2143–2147

    Article  CAS  Google Scholar 

  • Zhang DS, Toh GW, Lin H, Chen YY (2012) In situ synthesis of silver nanoparticles on silk fabric with PNP for antibacterial finishing. J Mater Sci 47:5721–5728

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors would like to acknowledge the financial support from the Shanghai Natural Science Foundation (10ZR1407700), Shanghai Pujiang Talent Project (11PJ1407600), the Research and Innovation Project of Municipal Education Commission of Shanghai (12YZ085).

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Correspondence to Jie Liang.

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Kang, ZZ., Zhang, B., Jiao, YC. et al. High-efficacy antimicrobial cellulose grafted by a novel quaternarized N-halamine. Cellulose 20, 885–893 (2013). https://doi.org/10.1007/s10570-012-9848-4

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  • DOI: https://doi.org/10.1007/s10570-012-9848-4

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