Skip to main content
Erschienen in: Cellulose 6/2013

01.12.2013 | Original Paper

Antibacterial cotton treated with N-halamine and quaternary ammonium salt

verfasst von: Ying Liu, Kaikai Ma, Rong Li, Xuehong Ren, T. S. Huang

Erschienen in: Cellulose | Ausgabe 6/2013

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config
loading …

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.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Literatur
Zurück zum Zitat Badrossamay RM, Sun G (2008) Preparation of rechargeable biocidal polypropylene by reactive extrusion with diallylamino triazine. Eur Polym J 44:733–742CrossRef Badrossamay RM, Sun G (2008) Preparation of rechargeable biocidal polypropylene by reactive extrusion with diallylamino triazine. Eur Polym J 44:733–742CrossRef
Zurück zum Zitat 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 27:4825–4830CrossRef 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 27:4825–4830CrossRef
Zurück zum Zitat Cerkez I, Kocer HB, Worley SD, Broughton RM, Huang TS (2011) N-halamine biocidal coatings via a layer-by-layer assembly technique. Langmuir 27:4091–4097CrossRef Cerkez I, Kocer HB, Worley SD, Broughton RM, Huang TS (2011) N-halamine biocidal coatings via a layer-by-layer assembly technique. Langmuir 27:4091–4097CrossRef
Zurück zum Zitat Cerkez I, Worley SD, Broughton RM, Huang TS (2013) Rechargeable antimicrobial coatings for poly(lactic acid) nonwoven fabrics. Polym 54:536–541CrossRef Cerkez I, Worley SD, Broughton RM, Huang TS (2013) Rechargeable antimicrobial coatings for poly(lactic acid) nonwoven fabrics. Polym 54:536–541CrossRef
Zurück zum Zitat 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 92:363–367CrossRef 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 92:363–367CrossRef
Zurück zum Zitat 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 28:561–572CrossRef 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 28:561–572CrossRef
Zurück zum Zitat 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 45:2443–2449CrossRef 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 45:2443–2449CrossRef
Zurück zum Zitat 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:1353–1358CrossRef 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:1353–1358CrossRef
Zurück zum Zitat Ioppolo JA, Kassiou M, Rendina LM (2009) Water-soluble phosphonium salts containing 1,12-dicarba-closo-dodecaborane(12). Tetrahedron Lett 50:6457–6461CrossRef Ioppolo JA, Kassiou M, Rendina LM (2009) Water-soluble phosphonium salts containing 1,12-dicarba-closo-dodecaborane(12). Tetrahedron Lett 50:6457–6461CrossRef
Zurück zum Zitat 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 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
Zurück zum Zitat 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 221:80–89CrossRef 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 221:80–89CrossRef
Zurück zum Zitat 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 14:157–160CrossRef 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 14:157–160CrossRef
Zurück zum Zitat Kocer H, Cerkez I, Worley SD, Broughton RM, Huang TS (2011a) Cellulose/starch/HALS composite fibers extruded from an ionic liquid. Carbohydr Polym 86:922–927CrossRef Kocer H, Cerkez I, Worley SD, Broughton RM, Huang TS (2011a) Cellulose/starch/HALS composite fibers extruded from an ionic liquid. Carbohydr Polym 86:922–927CrossRef
Zurück zum Zitat Kocer HB, Worley SD, Broughton RM, Huang TS (2011b) A novel N-halamine acrylamide monomer and its copolymers for antimicrobial coatings. React Funct Polym 71:561–568CrossRef Kocer HB, Worley SD, Broughton RM, Huang TS (2011b) A novel N-halamine acrylamide monomer and its copolymers for antimicrobial coatings. React Funct Polym 71:561–568CrossRef
Zurück zum Zitat Kou L, Liang J, Ren X, Kocer HB, Worley SD, Broughton RM, Huang TS (2009a) Novel N-halamine silanes. Colloids Surf A 345:88–94CrossRef Kou L, Liang J, Ren X, Kocer HB, Worley SD, Broughton RM, Huang TS (2009a) Novel N-halamine silanes. Colloids Surf A 345:88–94CrossRef
Zurück zum Zitat 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 48:6521–6526CrossRef 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 48:6521–6526CrossRef
Zurück zum Zitat Li J, Zhang Q, Wang Y, Zhang W, Li T (2012) Synthesis and properties of organosilicon quaternary salts surfactants. J Surfactants Deterg 15:339–344CrossRef Li J, Zhang Q, Wang Y, Zhang W, Li T (2012) Synthesis and properties of organosilicon quaternary salts surfactants. J Surfactants Deterg 15:339–344CrossRef
Zurück zum Zitat 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 97:1161–1166CrossRef 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 97:1161–1166CrossRef
Zurück zum Zitat Liang J, Chen Y, Barnes K, Wu R, Worley SD, Huang TS (2006) N-halamine/quat siloxane copolymers for use in biocidal coatings. Biomater 27:2495–2501CrossRef Liang J, Chen Y, Barnes K, Wu R, Worley SD, Huang TS (2006) N-halamine/quat siloxane copolymers for use in biocidal coatings. Biomater 27:2495–2501CrossRef
Zurück zum Zitat Liang J, Barnes K, Akdag A, Worley SD, Lee J, Broughton RM, Huang TS (2007) Improved antimicrobial siloxane. Ind Eng Chem Res 46:1861–1866CrossRef Liang J, Barnes K, Akdag A, Worley SD, Lee J, Broughton RM, Huang TS (2007) Improved antimicrobial siloxane. Ind Eng Chem Res 46:1861–1866CrossRef
Zurück zum Zitat Liu S, Sun G (2008) Radical graft functional modification of cellulose with allyl monomers: chemistry and structure characterization. Carbohydr Polym 71:614–625CrossRef Liu S, Sun G (2008) Radical graft functional modification of cellulose with allyl monomers: chemistry and structure characterization. Carbohydr Polym 71:614–625CrossRef
Zurück zum Zitat 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 67:355–366CrossRef 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 67:355–366CrossRef
Zurück zum Zitat 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 57:1376–1386CrossRef 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 57:1376–1386CrossRef
Zurück zum Zitat 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 317:711–716CrossRef 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 317:711–716CrossRef
Zurück zum Zitat 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 15:593–598CrossRef 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 15:593–598CrossRef
Zurück zum Zitat Ren X, Akdag A, Kocer HB, Worley SD, Broughton RM, Huang TS (2009) N-halamine-coated cotton for antimicrobial and detoxification applications. Carbohydr Polym 78:220–226CrossRef Ren X, Akdag A, Kocer HB, Worley SD, Broughton RM, Huang TS (2009) N-halamine-coated cotton for antimicrobial and detoxification applications. Carbohydr Polym 78:220–226CrossRef
Zurück zum Zitat 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 61:340–354CrossRef 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 61:340–354CrossRef
Zurück zum Zitat Tischer M, Pradel G, Ohlsen K, Holzgrabe U (2012) Quaternary ammonium salts and their antimicrobial potential: targets or nonspecific interactions? ChemInform 7:22–31 Tischer M, Pradel G, Ohlsen K, Holzgrabe U (2012) Quaternary ammonium salts and their antimicrobial potential: targets or nonspecific interactions? ChemInform 7:22–31
Zurück zum Zitat Wan W, Yeow JTW (2012) Antibacterial properties of poly(quaternary ammonium) modified gold and titanium dioxide nanoparticles. J Nanosci Nanotechnol 12:4601–4606CrossRef Wan W, Yeow JTW (2012) Antibacterial properties of poly(quaternary ammonium) modified gold and titanium dioxide nanoparticles. J Nanosci Nanotechnol 12:4601–4606CrossRef
Zurück zum Zitat 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 122:2542–2551CrossRef 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 122:2542–2551CrossRef
Zurück zum Zitat 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 88:35–39CrossRef 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 88:35–39CrossRef
Zurück zum Zitat Worley SD, Chen Y, Wang JW, Wu R (2005) Novel N-halamine siloxane monomers and polymers for preparing biocidal coatings. Surf Coat Int 88:93–99CrossRef Worley SD, Chen Y, Wang JW, Wu R (2005) Novel N-halamine siloxane monomers and polymers for preparing biocidal coatings. Surf Coat Int 88:93–99CrossRef
Zurück zum Zitat 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 86:232–236CrossRef 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 86:232–236CrossRef
Zurück zum Zitat 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 87:839–845CrossRef 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 87:839–845CrossRef
Zurück zum Zitat 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 3:907–913CrossRef 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 3:907–913CrossRef
Zurück zum Zitat Zhao Q, Wang S, Muller-Steinhagen H (2004) Tailored surface free energy of membrane diffusers to minimize microbial adhesion. Appl Surf Sci 230:371–378CrossRef Zhao Q, Wang S, Muller-Steinhagen H (2004) Tailored surface free energy of membrane diffusers to minimize microbial adhesion. Appl Surf Sci 230:371–378CrossRef
Metadaten
Titel
Antibacterial cotton treated with N-halamine and quaternary ammonium salt
verfasst von
Ying Liu
Kaikai Ma
Rong Li
Xuehong Ren
T. S. Huang
Publikationsdatum
01.12.2013
Verlag
Springer Netherlands
Erschienen in
Cellulose / Ausgabe 6/2013
Print ISSN: 0969-0239
Elektronische ISSN: 1572-882X
DOI
https://doi.org/10.1007/s10570-013-0056-7

Weitere Artikel der Ausgabe 6/2013

Cellulose 6/2013 Zur Ausgabe