N-halamine-based antimicrobial additives for polymers: Preparation, characterization, and antimicrobial activity

Industrial and Engineering Chemistry Research

Volumn 45, Issue 8, 2006, Pages 2634-2640

  Chen, Zhaobin ^a   Sun, Yuyu ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3-ALKYL-5,5-DIMETHYLHYDANTOIN; ALKYL BROMIDES; GRAM POSITIVE BACTERIA; L-CHLORO-3-ALKYL-5,5-DIMETHYLHYDANTOINS (CADMH);

AMINES; BACTERIA; BACTERIOLOGY; CHLORINATION; FOURIER TRANSFORM INFRARED SPECTROSCOPY; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE;

POLYMERS;

AMINES; BACTERIA; BACTERIOLOGY; CHLORINATION; FOURIER TRANSFORM INFRARED SPECTROSCOPY; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE; POLYMERS;

EID: 33646345138     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie060088a     Document Type: Conference Paper

References (35)

1. Binder, S.; Levitt, A. M.; Sacks, J. J.; Hughes, J. M. Emerging Infectious Diseases: Public Health Issues for the 21st Century. Science 1999, 254, 1311-1313.
2. Larson, E.; Olmsted, R. N. Research Priorities Project, Year 2000: the Lone Ranger Rides Again. Am. J. Infect. Control 2001, 29, 69-72.
3. Neely, A. N.; Maley, M. P. Survival of Enterpcocci and Staphylococci on Hospital Fabrics and Plastic. J. Clin. Microbiol. 2000, 38, 724-726.
4. Scott, E.; Bloomfield, S. F. The Survival and Transfer of Microbial Contamination via Cloths, Hands and Utensils. J. Appl. Bacteriol. 1990, 68, 271-278.
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, 887-892.
6. Litsky, W. Wanted: Plastics with Antimicrobial Properties. Am. J. Pub. Health 1990, 80, 13-15.
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, 7098-7104.
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, 1966-1974.
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, 5981-5985.
10. Jayaraman, A.; Yarmush, M. L.; Roth, C. M. Molecular Bioengineering. Ind. Eng. Chem. Res. 2002, 41, 441-455.
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. 6. Ind. Eng. Chem. Res. 1991, 30, 2426-2430.
12. Worley, S. D.; Williams, D. E. Halamine Water Disinfectants. Crit. Rev. Environ. Control 1988, 18, 133-175.
13. Sun, Y.; Sun, G. Novel Refreshable N-Halamine Polymeric Biocides: N-Chlorination of Aromatic Polyamides. Ind. Eng. Chem. Res. 2004, 43, 5015-5020.
14. Chen, Y.; Worley, S. D.; Kim, J.; Wei, C. I.; Chen, T. Y.; Santiago, J. I.; Williams, J. F.; Sun, G. Biocidal Poly(styrenehydantoin) Beads for Disinfection of Water. Ind. Eng. Chem. Res. 2003, 42, 280-284.
15. Chen, Z.; Sun, Y. N-Chloro-Hindered Amines as Multifunctional Polymer Additives. Macromolecules 2005, 38, 8116-8119.
16. Sun, G.; Xu, X. Durable and Regenerable Antibacterial Finishing of Fabrics: Biocidal Properties. Text. Chem. Color. 1998, 30, 26-30.
17. Sun, Y.; Sun, G. Durable and Refreshable Polymeric N-Halamine Biocides Containing 3-(4′-Vinylbenzyl)-5,5-dimethylhydantoin. J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 3348-3355.
18. 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., Part B 2003, 86, 273-277.
19. Sun, Y.; Sun, G. Synthesis, Characterization, and Antibacterial Activities of Novel N-Halamine Polymer Beads Prepared by Suspension Copolymerization. Macromolecules 2002, 35, 8909-8912.
20. Chen, Z.; Sun, Y. Antimicrobial Functions of N-Chloro-Hindered Amines. Polym. Preprint 2005, 46, 835-836.
21. Worley, S. D.; Sun, G. Biocidal Polymers. Trends Polym. Sci. 1996, 11, 364-370.
22. Richmond, J. Y.; McKinney, R. W. Biosafety in Microbiological and Biomedical Laboratories, 4th ed.; Government Printing Office: Washington, DC, 1999; p 12.
23. Moore, G. E.; Badger, R. M. The Infrared Spectra and Structure of the Chloramines and Nitrogen Trichloride. J. Am. Chem. Soc. 1952, 74, 6076-6080.
24. Heasley, V. L.; Kovacic, P.; Lange, R. M. N-Haloalkylamines. Analyses and Amination of Toluene. J. Org. Chem. 1966, 31, 3050-3052.
25. Petterson, R. C.; Grzeskowiak, U.; Jules, L. H. W-Halogen Compounds. II. The N⋯Cl Stretching Band in Some N-Chloroamides. The Structure of Trichloroisocyanuric Acid. J. Org. Chem. 1960, 25, 1595-1598.
26. 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, 447-452.
27. a Values for Hydantoins by Spectrophotometry. J. Chem. Res. Synop. 1982, 5, 131.
28. 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, 277-282.
29. Uscumlic, G. S.; Kshad, A. A.; Mijin, D. Z. Synthesis and Investigation of Solvent Effects on the Ultraviolet Absorption Spectra of 1,3-Bis-Substituted 5,5-Dimethylhydantoins. J. Serb. Chem. Soc. 2003, 68, 699-706.
30. 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, 1387-1391
31. 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, 1669-1671.
32. Block, S. S. Disinfection, Sterilization and Preservation, 3rd ed.; Lea & Febiger: Philadelphia, 1983; pp 157-182.
33. Denver, S. P. Mechanisms of Action of Antibacterial Biocides. Int. Biodeterior. Biodegrad. 1995, 36, 227-245.
34. Russell, A. D. Mechanisms of Bacterial Resistance to Biocides. Int. Biodeterior. Biodegrad. 1995, 36, 247-265.
35. Denver, S. P.; Stewart, G. S. A. B. Mechanisms of Action of Disinfectants. Int. Biodeterior. Biodegrad. 1998, 41, 261-268.