Acyclic N-halamine polymeric biocidal films

Journal of Bioactive and Compatible Polymers

Volumn 25, Issue 4, 2010, Pages 392-405

  Ren, Xuehong ^a   Zhu, Changyun ^a   Kou, Lei ^a   Worley, S D ^a   Kocer, Hasan B ^b   Broughton, R M ^b   Huang, T S ^a  

^a AUBURN UNIVERSITY   (United States)

^b AUBURN UNIVERSITY   (United States)

Author keywords

Antimicrobial; Bacteria; Biocidal coatings; Biofilms; N halamine

Indexed keywords

ACRYLAMIDES; BIOCIDAL; BIOCIDAL COATINGS; E.COLI O157:H7; FTIR; LOW CONCENTRATIONS; METHACRYLAMIDES; N-HALAMINE; POLYESTER FABRIC; S. AUREUS; SODIUM HYPOCHLORITE SOLUTION; VINYL ACETATES;

AMIDES; BACTERIOLOGY; BIOFILMS; CHLORINE; COPOLYMERIZATION; COPOLYMERS; ESCHERICHIA COLI; FABRICS; INORGANIC COATINGS; MICROORGANISMS; PLASTIC COATINGS; POLYMERIC FILMS; SODIUM; TRANSPARENCY;

POLYVINYL ACETATES;

ACRYLAMIDE; AMIDE; BIOCIDE; HYPOCHLORITE SODIUM; N HALOAMINE; POLYMER; UNCLASSIFIED DRUG; VINYL ACETATE;

ANTIMICROBIAL ACTIVITY; ARTICLE; CHEMICAL STRUCTURE; CHLORINATION; DIFFERENTIAL SCANNING CALORIMETRY; ESCHERICHIA COLI O157; FILM; INFRARED SPECTROSCOPY; MOLECULAR WEIGHT; NONHUMAN; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; STAPHYLOCOCCUS AUREUS; TITRIMETRY; ULTRAVIOLET A RADIATION;

STAPHYLOCOCCUS AUREUS;

EID: 77953819539     PISSN: 08839115     EISSN: 15308030     Source Type: Journal    
DOI: 10.1177/0883911510370387     Document Type: Article

References (52)

1. Kanazawa, A., Ikeda, T. and Endo, T. (1993). Polymeric Phosphonium Salts as a Novel Class of Cationic Biocides. III. Immobilization of Phosphonium Salts by Surface Photografting and Antibacterial Activity of the Surface-treated Polymer Films, J. Polym. Sci. Part A: Polym. Chem., 31: 1467-1472. (Pubitemid 23637954)
2. Kenawy, E.R. and Mahmoud, Y.A.G. (2003). Biologically Active Polymers, 6: Synthesis and Antimicrobial Activity of some Linear Copolymers with Quaternary Ammonium and Phosphonium Groups, Macromol. Biosci., 3: 107-116.
3. Kenawy, E.R., Abdel-Hay, F.I., El-Shanshoury, A.E.R. R. and El-Newehy, M.H. (2002). Biologically Active Polymers. V. Synthesis and Antimicrobial Activity of Modified Poly(Glycidyl Methacrylate-co-2-Hydroxyethyl Methacrylate) Derivatives with Quaternary Ammonium and Phosphonium Salts, J. Polym. Sci. Part A: Polym. Chem., 40: 2384-2393.
4. Kenawy, E.R., Abdel-Hay, F.I., El-Magd, A.A. and 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: 419-429.
5. Hazziza-Laskar, J., Nurdin, N., Helary, G. and Sauvet, G. (1993). Biocidal Polymers Active by Contact. I. Synthesis of Polybutadiene with Pendant Quaternary Ammonium Groups, J. Appl. Polym. Sci., 50: 651-662.
6. Sauvet, G., Fortuniak, W., Kazmierski, K. and Chojnowski, J. (2003). Amphiphilic Block and Statistical Siloxane Copolymers with Antimicrobial Activity, J. Polym. Sci. Part A. Polym. Chem., 41: 2939-2948.
7. Lambert, J.L., Fina, G.T. and Fina, L.R. (1980). Preparation and Properties of Triiodide-, Pentaiodide-, and Heptaiodide-Quaternary Ammonium Strong Base Anion-exchange Resin Disinfectants, Ind. Eng. Chem. Prod. Res. Dev., 19: 256-258.
8. Murata, H., Koepsel, R.R., Matyjaszewski, K. and Russell, A.J. (2007). Permanent, Non-leaching Antibacterial Surfaces - 2: How High Density Cationic Surfaces Kill Bacterial Cells, Biomaterials, 28: 4870-4879.
9. Klibanov, A.M. (2007). Permanently Microbicidal Materials Coatings, J. Mater. Chem., 17: 2479-2482.
10. Park, D., Wang, J. and Klibanov, A.M. (2006). One-step, Painting-like Coating Procedures to make Surfaces Highly and Permanently Bactericidal, Biotechnol. Progr., 22: 584-589.
11. Lewis, K. and Klibanov, A.M. (2006). Surpassing Nature: Rational Design of Sterile-surface Materials, Trends Biotechnol., 23: 343-348.
12. Waschinski, C.J., Barnert, S., Theobald, A., Schubert, R., Kleinschmidt, F., Hoffmann, A. et al. (2008). Insights in the Antibacterial Action of Poly(Methyloxazoline)s with a Biocidal End Group and Varying Satellite Groups, Biomacromolecules, 9: 1764-1771.
13. Waschinski, C.J., Zimmermann, J., Salz, U., Hutzler, R., Sadowski, G. and Tiller, J.C. (2008). Design of Contact-active Antimicrobial Acrylate-based Materials Using Biocidal Macromers, Adv. Mater., 20: 104-108.
14. Waschinski, C.J., Herdes, V., Schueler, F. and Tiller, J.C. (2005). Influence of Satellite Groups on Telechelic Antimicrobial Functions of Polyoxazolines, Macromol. Biosci., 5: 149-156.
15. Waschinski, C.J. and Tiller, J.C. (2005). Poly(Oxazoline)s with Telechelic Antimicrobial Functions, Biomacromolecules, 6: 235-243.
16. Kurt, P., Wood, L., Ohman, D.E. and Wynne, K.J. (2007). Highly Effective Contact Antimicrobial Surfaces Via Polymer Surface Modifiers, Langmuir, 23: 4719-4723.
17. Kurt, P., Gamble, L.J. and Wynne, K.J. (2008). Surface Characterization of Biocidal Polyurethane Modifiers Having Poly(3,3-substituted)Oxetane Soft Blocks with Alkylammonium Side Chains, Langmuir, 24: 5816-5824.
18. Luo, J., Chen, Z. and Sun, Y. (2006). Controlling Biofilm Formation with an N-Halamine-based Polymeric Additive, J. Biomed. Mater. Res. Part A, 77: 823-831.
19. Chen, Z. and Sun, Y. (2006). N-Halamine-based Antimicrobial Additives for Polymers: Preparation, Characterization, and Antimicrobial Activity, Ind. Eng. Chem. Res., 45: 2634-2640.
20. Sun, Y. and Sun, G. (2001). Novel Regenerable N-Halamine Polymeric Biocides. II. Grafting of Hydantoin-containing Monomers onto Cotton Cellulose, J. Appl. Polym. Sci., 81: 617-624.
21. Sun, Y. and Sun, G. (2002). Durable and Regenerable Antimicrobial Textile Materials Prepared by a Continuous Grafting Process, J. Appl. Polym. Sci., 84: 1592-1599.
22. Liu, S. and Sun, G. (2008). Radical Graft Functional Modification of Cellulose with Allyl Monomers: Chemistry and Structure Characterization, Carbohyd. Polym., 71: 614-625.
23. Sun, G. and Xu, X. (1999). Durable and Regenerable Antibacterial Finishing of Fabrics: Fabric Properties, Text. Chemist Colorist, 31: 21-24. (Pubitemid 29204146)
24. Sun, G. and Xu, X. (1999). Durable and Regenerable Antibacterial Finishing of Fabrics: Biocidal Properties, Text. Chemist Colorist, 30: 26-30.
25. Sun, G. and Xu, X. (1999). Durable and Regenerable Antibacterial Finishing of Fabrics: Chemical Structures, Text. Chemist Colorist, 31: 31-35. (Pubitemid 29366115)
26. Lin, J., Cammarata, V. and Worley, S.D. (2001). Infrared Characterization of Biocidal Polyester, Polymer, 42: 7903-7906.
27. Lin, J., Winkelmann, C., Worley, S.D., Broughton, R.M. and Williams, J.F. (2001). Antimicrobial Treatment of Polyester, J. Appl. Polym. Sci., 81: 943-947.
28. Lin, J., Winkelmann, C., Worley, S.D., Kim, J., Wei, C.I., Cho, U. et al. (2002). Biocidal Polyester, J. Appl. Polym. Sci., 85: 177-182.
29. Barnes, K., Liang, J., Wu, R., Worley, S.D., Lee, J., Broughton, R.M. et al. (2006). Synthesis and Antimicrobial Applications of 5,5'- Ethylenebis[5Methyl-3-(3-Triethoxysilylpropyl)Hydantoin], Biomaterials, 27: 4825-4830.
30. Kou, L., Liang, J., Worley, S.D., Lee, J., Broughton, R.M. and Huang, T.S. (2006). Antimicrobial Cellulose: Preparation and Application of 5-Methyl-5-Aminomethylhydantoin, Res. J. Text. Apparel, 10: 44-53.
31. Lee, J., Broughton, R.M., Akdag, A., Worley, S.D. and Huang, T.S. (2007). Antimicrobial Fibers Created Via Polycarboxylic Acid Durable Press Finishing, Text. Res. J., 77: 604-611.
32. Liang, J., Barnes, K., Akdag, A., Worley, S.D., Lee, J., Broughton, R.M. et al. (2007). Improved Antimicrobial Siloxane, Ind. Eng. Chem. Res., 46: 1861-1866.
33. Liang, J., Chen, Y., Barnes, K., Wu, R., Worley, S.D. and Huang, T.S. (2006). N-Halamine/Quat Siloxane Copolymers for Use in Biocidal Coatings, Biomaterials, 27: 2495-2501.
34. Liang, J., Wu, R., Wang, J.W., Barnes, K., Worley, S.D., Cho, U. et al. (2007). N-Halamine Biocidal Coatings, J. Ind. Microbiol. Biotechnol., 34: 157-163.
35. Ren, X., Kou, L., Kocer, H.B., Zhu, C., Worley, S.D., Broughton, R.M. et al. (2008). Antimicrobial Coating of an N-Halamine Biocidal Monomer on Cotton Fibers Via Admicellar Polymerization, Colloid and Surface A: Physicochem. Eng. Aspects, 317: 711-716.
36. Ren, X., Kou, L., Liang, J., Worley, S.D., Tzou, Y.M. and Huang, T.S. (2008). Antimicrobial Efficacy and Light Stability of N-Halamine Siloxanes Bound to Cotton, Cellulose, 15: 593-598.
37. Makal, U., Wood, L., Ohman, D.E. and Wynne, K.J. (2006). Polyurethane Biocidal Polymeric Surface Modifiers, Biomaterials, 27: 1316-1326.
38. Grunzinger, S.J., Kurt, P., Brunson, K.M., Wood, L., Ohman, D.E. and Wynne, K.J. (2007). Biocidal Activity of Hydantoin-containing Polyurethane Polymeric Surface Modifiers, Polymer, 48: 4653-4662.
39. Sun, G., Wheatley, W.B. and Worley, S.D. (1994). A New Cyclic N-Halamine Biocidal Polymer, Ind. Eng. Chem. Res., 33: 168-170.
40. Chen, Y., Worley, S.D., Kim, J., Wei, C.I., Chen, T.Y., Santiago, J.I. et al. (2003). Biocidal Poly(Styrenehydantoin) Beads for Disinfection of Water, Ind. Eng. Chem. Res., 42: 280-284.
41. Chen, Y., Worley, S.D., Kim, J., Wei, C.I., Chen, T.Y., Suess, J. et al. (2003). Biocidal Polystyrenehydantoin Beads. 2. Control of Chlorine Loading, Ind. Eng. Chem. Res., 42: 5715-5720.
42. Chen, Y., Worley, S.D., Huang, T.S., Weese, J., Kim, J., Wei, C.I. et al. (2004). Biocidal Polystyrene Beads. IV. Functionalized Methylated Polystyrene, J. Appl. Polym. Sci., 92: 368-372.
43. Chen, Y., Worley, S.D., Huang, T.S., Weese, J., Kim, J., Wei, C.I. et al. (2004). Biocidal Polystyrene Beads. III. Comparison of N-Halamine and Quat Functional Groups, J. Appl. Polym. Sci., 92: 363-367.
44. Sun, Y. and Sun, G. (2001). Novel Regenerable N-Halamine Polymeric Biocides. I. Synthesis, Characterization, and Antibacterial Activity of Hydantoin-containing Polymers, J. Appl. Polym. Sci., 80: 2460-2467.
45. Sun, Y., Chen, T.Y., Worley, S.D. and Sun, G. (2001). Novel Refreshable N-Halamine Polymeric Biocides Containing Imidazolidin-4-One Derivatives, J. Polym. Sci. Part A: Polym. Chem., 39: 3073-3084.
46. Sun, Y. and Sun, G. (2001). Durable and Refreshable Polymeric N-Halamine Biocides Containing 3-(4'-vinylbenzyl)-5,5-dimethylhydantoin, J. Polym. Sci. Part A: Polym. Chem., 39: 3348-3355.
47. Liu, S. and Sun, G. (2006). Durable and Regenerable Biocidal Polymers: Acyclic N-Halamine Cotton Cellulose, Ind. Eng. Chem. Res., 45: 6477-6482.
48. Luo, J. and Sun, Y. (2008). Acyclic N-Halamine-based Biocidal Tubing: Preparation, Characterization, and Rechargeable Biofilm-controlling Functions, J. Biomed. Mater. Res. Part A, 84A: 631-642.
49. Luo, J. and Sun, Y. (2006). Acyclic N-Halamine-based Fibrous Materials: Preparation, Characterization, and Biocidal Functions, J. Polym. Sci. Part A: Polym. Chem., 44: 3588-3600.
50. Worley, S.D. and Sun, G. (1996). Biocidal Polymers, Trends Polym. Sci., 4: 364-370.
51. Crispin, E.G., Schuquel, I.T.A., Rubira, A.F. and Muniz, E.C. (2000). Solvent Effects on the Miscibility of PMMA/PVAc Blends II. Using Two-dimensional NMR Method, NOESY, Polymer, 41: 933-945.
52. Tan, K.H., Saha, M.K. and Liew, Y.S. (2009). FRP-strengthened RC Beams under Sustained Loads and Weathering, Cem. Concr. Compos., 31: 290-300.