Effect of alkyl derivatization on several properties of N-halamine antimicrobial siloxane coatings

Industrial and Engineering Chemistry Research

Volumn 47, Issue 20, 2008, Pages 7558-7563

  Kocer, Kasan B ^a   Akdag, Akin ^b   Ren, Xuehong ^b   Broughton, R M ^a   Worley, S D ^b   Huang, T S ^b  

^a AUBURN UNIVERSITY   (United States)

^b AUBURN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL CHAIN LENGTHS; ALKYL SUBSTITUENTS; ALKYL SUBSTITUTIONS; ANTI-MICROBIAL; ANTIMICROBIAL COATINGS; BIOCIDAL; BIOCIDAL ACTIVITIES; DERIVATIZATION; DERIVATIZATION OF; ESCHERICHIA COLI O157:H7; HALAMINE; HYDANTOIN; QUATERNARY AMMONIUM SALTS; SILOXANE COATINGS; ULTRAVIOLET LIGHTS;

AMINES; AMMONIUM COMPOUNDS; CHEMICAL REACTIONS; CHLORINE; DERIVATIVES; ESCHERICHIA COLI; INORGANIC COATINGS; ULTRAVIOLET RADIATION;

ALKYLATION;

EID: 54949110180     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie800899u     Document Type: Article

References (35)

1. Hambraeus, A. Infection Control from a Global Perspective. J. Hosp. Infect. 2006, 64, 217-223.
2. Hardy, K. J.; Oppenheim, B. A.; Gossain, S.; Gao, F.; Hawkey, P. M. A Study of the Relationship between Environmental Contamination with Methicillin-resistant Staphylococcus aureus (MRSA) and Patients' Acquisition of MRSA. Infect. Control Hosp. Epidemiol. 2006, 27, 127-132.
3. Neely, A. N.; Maley, M. P. Survival of Enterococci and Staphylococci on Hospital Fabrics and Plastics. J. Clin. Microbiol. 2000, 724-726.
4. Harbartha, S.; Saxa, H.; Gastmeier, P. The Preventable Proportion of Nosocomial Infections: An Overview of Published Reports. J. Hosp. Infect. 2003, 54, 258-266.
5. Hambraeus, A. Transfer of Staphylococcus aureus via Nurses' Uniforms. J. Hyg. 1973, 71, 799-814.
6. Hedin, G.; Hambraeus, A. Multiply Antibiotic-Resistant Staphylococcus epidermidis in Patients, Staff and Environment - A One-Week Survey in a Bone Marrow Transplant Unit. J. Hasp. Infect. 1991, 17, 95-106.
7. Scott, E.; Bloomfield, S. F. The Survival and Transfer of Microbial Contamination via Cloths, Hands and Utensils. J. Appl. Bacteriol. 1990, 68, 271-278.
8. Boyce, J. M.; Potter-Bynoe, G.; Chenevert, C.; King, T. Environmental Contamination Due to Methicillin-Resistam Staphylococcus aureus: Possible Infection Control Implications. Infect. Control Hosp. Epidemiol. 1997, 18, 622-627.
9. For example see: (a) Isquith, A. J.; Abbot, A.; Walters, P. A. Surfacebonded Antimicrobial Activity of an Organosilicone Quaternary Ammonium Chloride. Appl. Microbiol. 1972, 24, 859-86.
10. For example, see: (a) Lambert, J. L.; Fina, G. T. Preparation and Properties of Triiodide-, Pentaiodide-, and Heptaiodide-Quaternary Ammonium Strong Base Anion-Exchange Resin Disinfectants. Ind. Eng. Chem. Prod. Res. Dev. 1980, 79, 256-258.
11. For example, see: (a) Sauvet, G.; Fortuniak, W.; Kazmierski, K.; Chojnowski, J. Amphiphilic Block and Statistical Siloxane Copolymers with Antimicrobial Activity. J. Polym. Sci. Part A: Polym. Chem. 2003, 41, 2939-2948.
12. For example see: (a) Stobiea, N.; Duffya, B.; McCormack, D. E.; Colreavya, J.; Hidalgoa, M.; McHalec, P.; Hinderd, S. J. Prevention of Staphylococcus epidermidis Biofilm Formation Using a Low-Temperature Processed Silver-Doped Phenyltriethoxysilane Sol-Gel Coating. Biomaterials 2008, 29, 963-969.
13. For example, see: (a) Nagar, R. Structural and Microbial Studies of Some Transition Metal Complexes. J. Inorg. Biochem. 1989, 37, 193-200.
14. Liang, J.; Chen, Y.; Barnes, K.; Wu, R.; Worley, S. D.; Huang, T. S. A'-Halamine/Quat Siloxane Copolymers for Use in Biocidal Coatings. Biomaterials 2006, 27, 2495-2501.
15. Worley, S. D.; Sun, G. Biocidal Polymers. Trends Polym. Sci. 1996, 4, 364-370.
16. Kenawy, E. R.; Worley, S. D.; Broughton, R. The Chemistry and Applications of Antimicrobial Polymers; A State of the Art Review. Biomacromolecules 2007, 8, 1359-1384.
17. Sun, Y. Y.; Chen, T.; Worley, S. D.; Sun, G. Novel Refreshable JV-Halamine Polymeric Biocides Containing Imidazolidin-4-one Derivatives. J. Polym. Sci. Part A: Polym. Chem. 2001, 39, 3073-3084.
18. Makal, U.; Wood, L.; Ohman, D. E.; Wynne, K. J. Polyurethane Biocidal Polymeric Surface Modifiers. Biomaterials 2006,27, 1316-1326.
19. Worley, S. D.; Chen, Y.; Wang, J. W.; Wu, R.; Cho, U.; Broughton, R. M.; Kim, J.; Wei, C. I.; Williams, J. F.; Chen, J.; Li, Y. Novel W-Halamine Siloxane Monomers and Polymers for Preparing Biocidal Coatings. Surf. Coat. Int. Part B: Coat. Trans. 2005, 88, 93-100.
20. Chen, Z.; Sun, Y. Y. N-Halamine-Based Antimicrobial Additives for Polymers: Preparation, Characterization, and Antimicrobial Activity. Ind. Eng. Chem. Res. 2006, 45, 2634-2640.
21. Liang, J.; Wu, R.; Wang, J. W.; Barnes, K.; Worley, S. D.; Cho, U.; Lee, J.; Broughton, R. M.; Huang, T. S. W-Halamine Biocidal Coatings. J. Ind. Microbiol. Biotechnol. 2007, 34, 157-163.
22. Williams, D. E.; Eider, E. D.; Worley, S. D. Is Free Halogen Necessary for Disinfection? Appl. Environ. Microbiol. 1988, 54, 2583-2585.
23. Akdag, A.; Okur, S.; McKee, M. L.; Worley, S. D. The Stabilities of N-C1 Bonds in Biocidal Materials. J. Chem. Theory Comput. 2006, 2, 879-884.
24. Russell, A. D.; Chopra, I. Understanding Antibacterial Action and Resistance, 2nd ed; Chichester: Ellis Horwood, 1996.
25. Denyer, S. P. Mechanisms of Action of Antibacterial Biocides. Int. Biodeterior. Biodegrad. 1995, 36, 221-245.
26. Denyer, S. P.; Stewart, G. S. A. B. Mechanisms of Action of Disinfectants. Int. Biodeterior. Biodegrad. 1998, 41, 261-268.
27. Russell, A. D. Mechanisms of Bacterial Insusceptibility to Biocides. Am. J. Infect. Control 2001, 29, 259-261.
28. Russell, A. D. Bacterial Resistance to Disinfectants: Present Knowledge and Future Problems. J. Hosp. Infect. 1999, 43, S57-S68.
29. Scholl, S.; Koch, A.; Henning, D.; Kempter, G.; Kleinpeter, E. The Influence of Structure and Lipophilicity of Hydantoin Derivatives on Anticonvulsant Activity. Struct. Chem. 1999, 10, 355-366.
30. Block, S. S. Disinfection, Sterilization and Preservation, 3rd ed.; Lea & Febiger: Philadelphia, 1983; pp 743-745.
31. Nakae, T. Outer Membrane of Salmonella. Isolation of Protein Complex That Produces Transmembrane Channels. J. Biol. Chem. 1976, 257, 2176-2178.
32. Shirai, A.; Sumitomo, T.; Yoshida, M.; Kaimura, T.; Nagamune, H.; Maeda, T.; Kourai, H. Synthesis and Biological Properties of Gemini Quaternary Ammonium Compounds, 5,5′-[2,2′-(α,ω- Polymethylenedicarbonyldioxy)diethyl]bis-(3-alkyl-4-methylthiazolium iodide) and Its Brominated Analog. Chem. Pharm. Bull. 2006, 54, 639-645.
33. Liu, W.; Liu, X.; Knaebel, D.; Luck, L.; Li, Y. Synthesis and Antibacterial Evaluation of Novel Water-Soluble Organic Peroxides. Antimicrob. Agents Chemother. 1998, 42, 911-915.
34. Jia, Z.; Shen, D.; Xu, W. Synthesis and Antibacterial Activities of Quaternary Ammonium Salt of Chitosan. Carbohydr. Res. 2001, 333, 1-6.
35. Berger, A. Hydantoinylsilanes. US Patent 4,412,078, 1983.