Novel N-halamine silanes

Colloids and Surfaces A: Physicochemical and Engineering Aspects

Volumn 345, Issue 1-3, 2009, Pages 88-94

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

^a AUBURN UNIVERSITY   (United States)

^b AUBURN UNIVERSITY   (United States)

Author keywords

Antimicrobial coating; Cotton; Disinfectant; N Halamine; Silica gel; Siloxane

Indexed keywords

COTTON; DISINFECTANTS; ESCHERICHIA COLI; GELATION; OXIDES; SILANES; SILICA; SILICA GEL; SODIUM;

AMBIENT LIGHT; ANTIMICROBIAL COATING; CONTACT TIME; ESCHERICHIA COLI O157:H7; GEL PARTICLES; N-HALAMINE; SILOXANE; SODIUM HYPOCHLORITE SOLUTION; STAPHYLOCOCCUS AUREUS; UV- AND;

PLASTIC COATINGS;

6 PHENYL 3 (3' TRIETHOXYSILYLPROPYL) 1,3,5 TRIAZINANE 2,4 DIONE; 6,6 DIMETHYL 3 (3' TRIETHOXYSILYLPROPYL) 1,3,5 TRIAZINANE 2,4 DIONE; CELLULOSE; HYPOCHLORITE SODIUM; MONOMER; N HALAMINE SILANE DERIVATIVE; SILANE DERIVATIVE; SILICA GEL; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CHLORINATION; COTTON; DISINFECTION; ESCHERICHIA COLI O157; LIGHT EXPOSURE; MATERIAL COATING; MOLECULAR STABILITY; NONHUMAN; PRIORITY JOURNAL; REACTION ANALYSIS; STAPHYLOCOCCUS AUREUS; ULTRAVIOLET RADIATION;

BACTERICIDES; COATINGS; COTTON; GELATION; OXIDES; POLYSILICONES; SILANES; SILICA; SILICA GEL; SODIUM;

EID: 67349166950     PISSN: 09277757     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.colsurfa.2009.04.047     Document Type: Article

References (63)

1. Patal M.B., Patel S.A., Ray A., Ray A., and Patel R.M. Synthesis, characterization, and antimicrobial activity of acrylic copolymers. J. Appl. Polym. Sci. 89 (2003) 895
2. Park E.-S., Lee H.-J., Park H.-Y., Kim M.-N., Chung K.-H., and Yoon J.-S. Antifungal effect of carbendazim supported on poly(ethylene-co-vinyl alcohol) and epoxy resin. J. Appl. Polym. Sci. 80 (2001) 728
3. Vigo T.L. In: Seymour R.B., and Porter R.S. (Eds). Manmade Fibers: Their Origin and Development (1992), Elsevier Appl. Sci., New York 214
4. Vigo T.L. In: Gebelein C., and Carraher C. (Eds). Biotechnology and Bioactive Polymers (1994), Plenum Press, New York 225
5. Emerson D.W., Shea D.T., and Sorensen E.M. Functionally modified poly(styrenedivinylbenzene). Preparation, characterization, and bactericidal action, Ind Eng. Chem. Prod. Res. Dev. 17 (1978) 269
6. Emerson D.W. Polymer-bound active chlorine: disinfection of water in a flow system. Polymer-supported reagents. 5. Ind. Eng. Chem. Res. 29 (1990) 448
7. Emerson D.W. Slow release of active chlorine and bromine from styrene-divinylbenzene copolymers bearing N,N-dichlorosulfonamide, N-chloro-N-alkylsulfonamide and N-bromo-N-alkylsulfonamide functional groups. Polymer-supported reagents. Ind. Eng. Chem. Res. 30 (1991) 2426
8. Zhang Y., Emerson D.W., and Steinberg S.M. Destruction of cyanide in water using N-chlorinated secondary sulfonamide-substituted macroporous poly(styrene-co-divinylbenzene). Ind. Eng. Chem. Res. 42 (2003) 5959
9. Bogoczek R., and Balawejder E.K. N-Monohalogeno- and N,N-dihalogenopoly(styrene-co-divinylbenzene)sulfonamides. Polym. Commun. 27 (1986) 286
10. Bogoczek R., and Balawejder E.K. Studies on a macromolecular dichloroamine-the N,N-dichloro poly(styrene-co-divinylbenzene) sulfonamides. Angew. Makromol. Chem. 169 (1989) 119
11. Kanazawa A., Ikeda T., and Endo T. 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 (1993) 1467
12. Kenawy E.R., Abdel-Hay F.I., El-Shanshoury A.E.R.R., and El-Newehy M.H. Biologically active polymers. V. Synthesis and antimicrobial activity of modified poly(glycidyl methacrylate-co-2-hydroxyethylmethacrylate) derivatives with quaternary ammonium and phosphonium salts. J. Polym. Sci. Part. A: Polym. Chem. 40 (2002) 2384
13. Kenawy E.R., Abdel-Hay F.I., El-Magd A.A., and Mahmoud Y. Biologically active polymers: VII. Synthesis and antimicrobial activity of some crosslinked copolymers with quaternary ammonium and phosphonium groups. React. Funct. Polym. 66 (2006) 419
14. Kenawy E.R., and Mahmoud Y.A.G. Biologically active polymers, 6: synthesis and antimicrobial activity of some linear copolymers with quaternary ammonium and phosphonium groups. Macromol. Biosci. 3 (2003) 107
15. Hazziza-Laskar J., Nurdin N., Helary G., and Sauvet G. Biocidal polymers active by contact. I. Synthesis of polybutadiene with pendant quaternary ammonium groups. J. Appl. Polym. Sci. 50 (1993) 651
16. Sauvet G., Fortuniak W., Kazmierski K., and Chojnowski J. Amphiphilic block and statistical siloxane copolymers with antimicrobial activity. J. Polym. Sci. Part A: Polym. Chem. 41 (2003) 2939
17. Lambert J.L., Fina G.T., and Fina L.R. Preparation and properties of triiodide-, pentaiodide-, and heptaiodide-quaternary ammonium strong base anion-exchange resin disinfectants. Ind. Eng. Chem. Prod. Res. Dev. 19 (1980) 256
18. Murata H., Koepsel R.R., Matyjaszewski K., and Russell A.J. Permanent, non-leaching antibacterial surfaces-2: how high density cationic surfaces kill bacterial cells. Biomaterials 28 (2007) 4870
19. Klibanov A.M. Permanently microbicidal materials coatings. J. Mater. Chem. 17 (2007) 2479-2482
20. Park D., Wang J., and Klibanov A.M. One-step, painting-like coating procedures to make surfaces highly and permanently bactericidal. Biotechnol. Prog. 22 (2006) 584
21. Lewis K., and Klibanov A.M. Surpassing nature: rational design of sterile-surface materials. Trends Biotechnol. 23 (2006) 343
22. Eren T., Som A., Rennie J.R., Nelson C.F., Urgina Y., Nusslein K., Coughlin E.B., and Tew G.N. Antibacterial and hemolytic activities of quaternary pyridinium functionalized polynorbornenes. Macromol. Chem. Phys. 209 (2008) 516
23. Colak S., and Tew G.N. Synthesis and solution properties of norbornene based polybetaines. Macromolecules 41 (2008) 8436
24. Waschinski C.J., Barnert S., Theobald A., Schubert R., Kleinschmidt F., Hoffmann A., Saalwaechter K., and Tiller J.C. Insights in the antibacterial action of poly(methyloxazolines) with a biocidal end group and varying satellite groups. Biomacromolecules 9 (2008) 1764
25. Waschinski C.J., Zimmermann J., Salz U., Hutzler R., Sadowski G., and Tiller L.C. Design of contact-active antimicrobial acrylate-based materials using biocidal macromers. Adv. Mater. 20 (2008) 104
26. Waschinski C.J., Herdes V., Schueler F., and Tiller J.C. Influence of satellite groups on telechelic antimicrobial functions of polyoxazolines. Macromol. Biosci. 5 (2005) 149
27. Waschinski C.J., and Tiller C.J.C. Poly(oxazolines) with telechelic antimicrobial functions. Biomacromolecules 6 (2005) 235
28. Kurt P., Wood L., Ohman D.E., and Wynne K.J. Highly effective contact antimicrobial surfaces via polymer surface modifiers. Langmuir 23 (2007) 4719
29. Kurt P., Gamble L.J., and Wynne K.J. Surface characterization of biocidal polyurethane modifiers having poly(3,3-substituted)oxetane soft blocks with alkylammonium side chains. Langmuir 24 (2008) 5816
30. Isquith A.J., Abbott E.A., and Walters P.A. Surface-bonded antimicrobial activity of an organosilicon quaternary ammonium chloride. Appl. Microbiol. 24 (1972) 859
31. Luo J., Chen Z., and Sun Y. Controlling biofilm formation with an N-halamine-based polymeric additive. J. Biomed. Mater. Res. Part A 77 (2006) 823
32. Chen Z., and Sun Y. N-Halamine-based antimicrobial additives for polymers: Preparation, characterization, and antimicrobial activity. Ind. Eng. Chem. Res. 45 (2006) 2634
33. Sun Y., and Sun G. Novel regenerable N-halamine polymeric biocides. II. Grafting of hydantion-containing monomers onto cotton cellulose. J. Appl. Polym. Sci. 81 (2001) 617
34. Sun Y., and Sun G. Durable and regenerable antimicrobial textile materials prepared by a continuous grafting process. J. Appl. Polym. Sci. 84 (2002) 1592
35. Liu S., and Sun G. Radical graft functional modification of cellulose with allyl monomers: Chemistry and structure characteriazation. Carbohydr. Polym. 71 (2008) 614
36. Sun Y., and Sun G. Novel regenerable N-halamine polymeric biocides. I. Synthesis, characterization, and antibacterial activity of hydantoin-containing polymers. J. Appl. Polym. Sci. 80 (2001) 2460
37. Liu S., and Sun G. Functional modification of poly(ethylene terephthalate) with an allyl monomer: Chemistry and structure characterization. Polymer 49 (2008) 5225
38. Makal U., Wood L., Ohman D.E., and Wynne K.J. Polyurethane biocidal polymeric surface modifiers. Biomaterials 27 (2006) 1316
39. Grunzinger S.J., Kurt P., Brunson K.M., Wood L., Ohman D.E., and Wynne K.J. Biocidal activity of hydantoin-containing polyurethane polymeric surface modifiers. Polymer 48 (2007) 4653
40. Luo J., and Sun Y. Acyclic N-halamine-based biocidal tubing: preparation, characterization, and rechargeable biofilm-controlling functions. J. Biomed. Mater. Res. Part A 84A (2008) 631
41. Luo J., and Sun Y. Acyclic N-halamine-based fibrous materials: preparation, characterization, and biocidal functions. J. Polym. Sci. Part A: Polym. Chem. 44 (2006) 3588
42. Worley S.D., and Williams D.E. Halamine water disinfectants. Crit. Rev. Environ. Cntr. 18 (1988) 133
43. Worley S.D., and Sun G. Biocidal polymers. Trends Polym. Sci. 4 (1996) 364
44. Liang J., Chen Y., Barnes K., Wu R., Worley S.D., and Huang T. N-Halamine/quat siloxane copolymers for use in biocidal coatings. Biomaterials 27 (2006) 2495
45. Liang J., Chen Y., Ren X., Wu R., Barnes K., Worley S.D., Broughton S.D.R.M., Cho U., Kocer H., and Huang T.S. Fabric treated with antimicrobial N-halamine epoxides. Ind. Eng. Chem. Res. 46 (2007) 6425
46. Kenawy E.R., Worley S.D., and Broughton R. The chemistry and applications of antimicrobial polymers; A state of the art review. Biomacromolecules 8 (2007) 1359
47. Sun Y.Y., Chen T., Worley S.D., and Sun G. Novel refreshable N-Halamine polymeric biocides containing imidazolidin-4-one derivatives. J. Polym. Sci. Part A: Polym. Chem. 39 (2001) 3073
48. 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., and Li Y. Novel N-Halamine siloxane monomers and polymers for preparing biocidal coatings. Surf. Coat. Int. Part B: Coat. Trans. 88 (2005) 93
49. Liang J., Barnes K., Akdag A., Worley S.D., Lee J., Broughton R.M., and Huang T.S. An improved antimicrobial siloxane. Ind. Eng. Chem. Res. 46 (2007) 1861
50. Liang J., Owens J.R., Huang T.S., and Worley S.D. Biocidal hydantoinylsiloxane functionalized polymers IV. N-Halamine-functionalized silica gel. J. Appl. Polym. Sci. 101 (2006) 3448
51. Liang J., Wu R., Wang J.W., Barnes K., Worley S.D., Cho U., Lee J., Broughton R.M., and Huang T.S. N-halamine biocidal coatings. J. Ind. Microbiol. Biotechnol. 34 (2007) 157
52. Ren X., Kocer H.B., Kou L., Worley S.D., Broughton R.M., Tzou Y.M., and Huang T.S. Antimicrobial polyester. J. Appl. Polym. Sci. 109 (2008) 2756
53. Williams J.F., Suess J., Santiago J., Worley S.D., Chen Y., Wang J., and Wu R. Antimicrobial properties of novel N-halamine siloxane coatings. Surf. Coat. Int. Part B: Coat. Trans. 88 (2005) 35
54. Ren X., Kou L., Liang J., Worley S.D., Tzou Y.-M., and Huang T.S. Antimicrobial efficacy and light stability of N-halamine siloxanes bound to cotton. Cellulose 15 (2008) 593
55. Barnes K., Liang J., Worley S.D., Lee J., Broughton R.M., and Huang T.S. Modification of silica gel, cellulose, and polyurethane with a sterically hindered N-halamine moiety to produce antimicrobial activity. J. Appl. Polym. Sci. 105 (2007) 2306
56. Kocer H.B., Akdag A., Ren X., Broughton R.M., Worley S.D., and Huang T.S. Effect of alkyl derivatization on several properties of N-Halamine antimicrobial siloxane coatings. Ind. Eng. Chem. Res. 47 (2008) 7558
57. Barnes K., Liang J., Wu R., Worley S.D., Lee J., Broughton R.M., and Huang T.S. Synthesis and antimicrobial applications of 5,5-ethylenebis[5-methyl-3- (3-triethoxysilylpropyl) hydantoin]. Biomaterials 27 (2006) 4825
58. Liang J., Wu R., Huang T.S., and Worley S.D. Polymerization of a hydantoinylsiloxane on particles of silicon dioxide to produce a biocidal sand. J. Appl. Polym. Sci. 97 (2005) 1161
59. Chen Y., Worley S.D., Kim J., Wei C.-I., Chen T.Y., Suess J., Kawai H., and Williams J.F. Ind. Eng. Chem. Res. 42 (2003) 5715
60. Akdag A., Okur S., McKee M.L., and Worley S.D. The stabilities of N-Cl bonds in biocidal materials. J. Chem. Theory Comput. 2 (2006) 879
61. Tsao T.-C., Love B.E., and Worley S.D. Preparation of previously unavailable 6,6-dialkylhexahydro-1,3,5-triazine-2,4-diones. Synth. Commun. 22 (1992) 1597
62. Worley S.D., Chen Y., Liang J., Wu R., Barnes K., Broughton R.M., Cho U., and Lee J. Biocidal siloxanes containing N-halogenated amine and amide functional groups for coating materials. PCT Int. Appl. (2005) WO 2005058814
63. We thank a reviewer for this suggestion.