Preparation and characterization of N-halamine-based antimicrobial fillers

Industrial and Engineering Chemistry Research

Volumn 51, Issue 14, 2012, Pages 5148-5156

  Padmanabhuni, Revathi V ^a   Luo, Jie ^b   Cao, Zhengbing ^b   Sun, Yuyu ^b  

^a W O Farber Center for Civic Leadership   (United States)

^b BioSNTR   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE CHLORINE; ADDITIVE CONTENTS; ANTI-BACTERIAL ACTIVITY; ANTIMICROBIAL ADDITIVES; BIFUNCTIONAL COMPOUNDS; CALCIUM SALTS; CELLULOSE ACETATES; FILLER SURFACES; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIUM; ORGANOPHILIC; POLYMER-FILLER; POTASSIUM SALTS; SEM ANALYSIS; STAPHYLOCOCCUS AUREUS; SURROUNDING ENVIRONMENT; UNDECANOIC ACID;

ADDITIVES; BACTERIA; BLEACHING; CALCIUM CARBONATE; CHLORINE; CLEANING; ENZYME INHIBITION; ESCHERICHIA COLI; FILLED POLYMERS; SALTS; SATURATED FATTY ACIDS;

FILLERS;

EID: 84859597565     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie300212x     Document Type: Article

References (52)

1. Binder, S.; Levitt, A. M.; Sacks, J. J.; Hughes, J. M. Emerging infectious diseases: Public health issues for the 21st century Science 1999, 284, 1311
2. Larson, E.; Olmsted, R. N. Research priorities project, year 2000: The lone ranger rides again Am. J. Infect. Control 2001, 29, 69
3. Neely, A. N.; Maley, M. P. Survival of Enterococci and Staphylococci on hospital fabrics and plastic J. Clin. Microbiol. 2000, 38, 724
4. Scott, E.; Bloomfield, S. F. The survival and transfer of microbial contamination via cloths, hands and utensils J. Appl. Bacteriol. 1990, 68, 271
5. Richards, M. J.; Edwards, J. R.; Culver, D. H.; Gaynes, R. P. Nosocomial infections in medical intensive care units in the United States Crit. Care Med. 1999, 27, 887
6. Litsky, W. Wanted: Plastics with antimicrobial properties Am. J. Pub. Health 1990, 80, 13
7. Cheng, Z.; Zhu, X.; Shi, Z. L.; Neoh, K. G.; Kang, E. T. Polymer microspheres with permanent antibacterial surface from surface-initiated atom transfer radical polymerization Ind. Eng. Chem. Res. 2005, 44, 7098
8. Pernak, J.; Branicka, M. Synthesis and aqueous ozonation of some pyridinium salts with alkoxymethyl and alkylthiomethyl hydrophobic groups Ind. Eng. Chem. Res. 2004, 43, 1966
9. Tiller, J. C.; Liao, C.; Lewis, K.; Klibanov, A. M. Designing surfaces that kill bacteria on contact Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 5981
10. Jayaraman, A.; Yarmush, M. L.; Roth, C. M. Molecular bioengineering Ind. Eng. Chem. Res. 2002, 41, 441
11. Emerson, D. W. Slow release of active chlorine and active bromine from styrene-divinylbenzene copolymers bearing N, N -dichlorosulfonamide, N -chloro- N -alkylsulfonamide, and N -bromo- N -alkylsufonamide functional groups. Polymer-supported reagents Ind. Eng. Chem. Res. 1991, 30, 2426
12. Worley, S. D.; Williams, D. E. Halamine water disinfectants Crit. Rev. Environ. Control 1988, 18, 133
13. Worley, S. D.; Sun, G. Biocidal polymers Trends Polym. Sci. 1996, 11, 364
14. Sun, G.; Xu, X. Durable and regenerable antibacterial finishing of fabrics: Biocidal properties Text. Chem. Color. 1998, 30, 26
15. Sun, Y.; Sun, G. Durable and refreshable polymeric N -halamine biocides containing 3-(4′-vinylbenzyl)-5,5-dimethylhydantoin J. Polym. Sci. A: Polym. Chem. 2001, 39, 3348
16. Sun, Y.; Sun, G. Synthesis, characterization, and antibacterial activities of novel N -halamine polymer beads prepared by suspension copolymerization Macromolecules 2002, 35, 8909
17. Worley, S. D.; Li, F.; Wu, R.; Kim, J.; Wei, C. I.; Williams, J. F.; Owens, J. R.; Wander, J. D.; Bargmeyer, A. M.; Shirtliff, M. E. A novel N -halamine monomer for preparing biocidal polyurethane coatings Surf. Coat. Int. B 2003, 86, 273
18. Chen, Y.; Worley, S. D.; Kim, J.; Wei, C. I.; Chen, T. Y.; Santiago, J. I.; Williams, J. F.; Sun, G. Biocidal poly(styrene hydantoin) beads for disinfection of water Ind. Eng. Chem. Res. 2003, 42, 280
19. Chen, Z.; Sun, Y. N -chloro-hindered amines as multifunctional polymer additives Macromolecules 2005, 38, 8116
20. Chen, Z.; Sun, Y. Antimicrobial functions of N -chloro-hindered amines Polym. Prepr. 2005, 46, 835
21. Chen, Z.; Sun, Y. N -Halamine based antimicrobial additives for polymers Ind. Eng. Chem. Res. 2006, 45, 2634
22. Sun, X.; Cao, Z.; Sun, Y. N -Chloro-alkoxy- s -triazine-based antimicrobial additives: Preparation, characterization, and antimicrobial and biofilm-controlling functions Ind. Eng. Chem. Res. 2009, 48, 607
23. Sun, X.; Cao, Z.; Porteous, N.; Sun, Y. Amine, melamine, and N -halamines as antimicrobial additives for polymers Ind. Eng. Chem. Res. 2010, 49, 11206
24. Cao, Z.; Sun, Y. Polymeric N -halamine latex emulsions for use in antimicrobial paints ACS Appl. Mater. Interfaces 2009, 1, 494
25. Luo, J.; Porteous, N.; Sun, Y. Rechargeable biofilm-controlling tubing materials for use in dental unit water lines ACS Appl. Mater. Interfaces 2011, 3, 2895
26. Kiselev, A. V. Adsorption properties of hydrophobic surfaces J. Colloid Interface Sci. 1968, 28, 430
27. Ferch, H. Amorphous synthetic silica products: Production and characterization Chem. Ing. Tech. 1976, 48, 922
28. Price, G. J.; Ansari, D. M. Surface modification of calcium carbonates studied by inverse gas chromatography and the effect on mechanical properties of filled polypropylene Polym. Int. 2004, 53, 430
29. 3 particles Polymer 2002, 43, 3661
30. Rothon, R. N., Ed. Particulate-Filled Polymer Composites; Longman Scientific and Technical: Harlow, Essex, U.K., 1995.
31. Rungruang, P.; Grady, B. P.; Supaphol, P. Surface-modified calcium carbonate particles by admicellar polymerization to be used as filler for isotactic polypropylene Colloids Surf. A 2006, 275, 114
32. Shi, X.; Rosa, R.; Lazzeri, A. On the coating of precipitated calcium carbonate with stearic acid in aqueous medium Langmuir 2010, 26, 8474
33. Edgar, K. J.; Buchanan, C. M.; Debenham, J. S.; Rundquist, P. A.; Seiler, B. D.; Shelton, M. C. Advances in cellulose ester performance and application Prog. Polym. Sci. 2001, 26, 1605
34. Fisher, S.; Thuemmler, K.; Volkert, B.; Hettrich, K.; Schmidt, I.; Fisher, K. Properties and applications of cellulose acetate Macromol. Symp. 2008, 262, 89
35. Richmond, J. Y.; McKinney, R. W. Biosafety in Microbiological and Biomedical Laboratories, 4 th ed.; U.S. Government Printing Office: Washington, DC, 1999; p 12.
36. Cen, L.; Neoh, K. G.; Kang, E. T. Antibacterial activity of cloth functionalized with N -alkylated poly(4-vinylpyridine) J. Biomed. Mater. Res. 2004, 74A, 70
37. Cauletti, C.; Devillanova, F. A.; Isaia, F.; Verani, G.; Vondrak, T. Electronic structure of five-membered heterocyclic compounds containing nitrogen, oxygen, sulfur and selenium. Gas-phase UV photoelectron spectra and quantum-mechanical calculations J. Mol. Struct. 1988, 175, 447
38. a Values for hydantoins by spectrophotometry J. Chem. Res. Synop. 1982, 5, 131
39. Ajo, D.; Casarin, M.; Granozzi, G.; Poli, A.; Tondello, E. Electronic structure of imides by UV photoelectron spectroscopy and INDO/S calculations: Hydantoin and urazole J. Mol. Struct. 1982, 82, 277
40. Uscumlic, G. S.; Kshad, A. A.; Mijin, D. Z. Synthesis and investigation of solvent effects on the ultraviolet absorptions spectra of 1, 3-bis-substituted-5,5-dimethylhydantoins J. Serb. Chem. Soc. 2003, 68, 699
41. Nakamoto, K. Infrared Spectra of Inorganic and Coordination Compounds; John Wiley & Sons: New York, 1970.
42. Zhang, J.; Guo, J.; Li, T.; Li, X. Chemical surface modification of calcium carbonate particles by maleic anhydride grafting polyethylene wax Int. J. Green Nanotechnol. Phys. Chem. 2010, 1, 65
43. Bodor, N.; Kaminski, J. J.; Worley, S. D.; Colton, R. J.; Lee, T. H.; Rabalais, J. W. Photoelectron spectra, hydrolytic stability, and antimicrobial activity of N -chlorinated piperidines J. Pharm. Sci. 1974, 63, 1387
44. Naquib, I.; Tsao, T.; Sarathy, P. K.; Worley, S. D. Kinetic versus thermodynamic control in chlorination of imidazolidin-4-one derivatives Ind. Eng. Chem. Res. 1991, 30, 1669
45. Block, S. S. Disinfection, Sterilization and Preservation, 3 rd ed.; Lea & Febiger: Philadelphia, 1983.
46. Denyer, S. P. Mechanisms of action of antibacterial biocides Int. Biodeterior. Biodegrad. 1995, 36, 227
47. Russell, A. D. Mechanism of bacterial resistance to biocides Int. Biodeterior. Biodegrad. 1995, 36, 247
48. Denyer, S. P.; Stewart, G. S. A. B. Mechanisms of action disinfectants Int. Biodeterior. Biodegrad. 1998, 41, 261
49. Stoodley, L. H.; Costerton, J. W.; Stoodley, P. Bacterial biofilms: From the natural environment to infectious diseases Nat. Rev. Microbiol. 2004, 2, 95
50. An, Y. H.; Friedman, R. J. Handbook of Bacterial Adhesion: Principles, Methods, and Applications; Humana Press: Totowa, NJ, 1999; Chapter 4, p 53.
51. Disinfection Byproducts. http://water.epa.gov/drink/contaminants/index. cfm#Byproducts (Accessed May 2009).
52. National Primary Drinking Water Regulations: Disinfectants and Disinfection Byproducts. Fed. Regist. 1998, 63, 69390.