High-efficacy antibacterial polymeric micro/nano particles with N-halamine functional groups

Chemical Engineering Journal

Volumn 254, Issue , 2014, Pages 30-38

  Yan, Xiufang ^a   Jie, Zhiqiang ^a   Zhao, Lianhong ^a   Yang, Hong ^a   Yang, Shiping ^a   Liang, Jie ^a  

^a SHANGHAI NORMAL UNIVERSITY   (China)

Author keywords

Antibacterial; Minimum inhibitory concentration; N halamine; Polymeric micro nano particle; Styrene

Indexed keywords

ACRYLIC MONOMERS; AMIDES; AMINES; CHLORINE COMPOUNDS; COPOLYMERIZATION; ENAMELS; ESCHERICHIA COLI; FIELD EMISSION MICROSCOPES; FOURIER TRANSFORM INFRARED SPECTROSCOPY; PHOTOELECTRON SPECTROSCOPY; SCANNING ELECTRON MICROSCOPY; SODIUM COMPOUNDS; STYRENE;

ANTIBACTERIAL; ESCHERICHIA COLI (E. COLI); FIELD EMISSION SCANNING ELECTRON MICROSCOPY; MICRO/NANO PARTICLE; MINIMUM BACTERICIDAL CONCENTRATION (MBC); MINIMUM INHIBITORY CONCENTRATION; N-HALAMINE; X RAY PHOTOELECTRON SPECTRA;

POLYMERS;

EID: 84902318022     PISSN: 13858947     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cej.2014.05.114     Document Type: Article

References (39)

1. Song J., Kong H., Jang J. Enhanced antibacterial performance of cationic polymer modified silica nanoparticles. Chem. Commun. 2009, 36:5418-5420.
2. Waschinski C.J., Zimmermann J., Salz U., Hutzler R., Sadowski G., Tiller J.C. Design of contact-active antimicrobial acrylate-based materials using biocidal macromers. Adv. Mater. 2008, 20:104-108.
3. Hegstad K., Langsrud S., Lunestad B.T., Scheie A.A., Sunde M., Yazdankhah S.P. Does the wide use of quaternary ammonium compounds enhance the selection and spread of antimicrobial resistance and thus threaten our health?. Microb. Drug Resist. 2010, 16:91-104.
4. Lu G., Wu D., Fu R. Studies on the synthesis and antibacterial activities of polymeric quaternary ammonium salts from dimethylaminoethyl methacrylate. React. Funct. Polym. 2007, 67:355-366.
5. Kenawy E., Abdel-Hay F.I., El-Shanshoury A.E.R., El-Newehy M.H. 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. 2002, 40:2384-2393.
6. Ran X., Wang L., Cao D., Lin Y., Hao J. Synthesis, characterization and in vitro biological activity of cobalt (II), copper (II) and zinc (II) Schiff base complexes derived from salicylaldehyde and d,l-selenomethionine. Appl. Organomet. Chem. 2011, 25:9-15.
7. Ahmed A.E.I., Hay J.N., Bushell M.E., Wardell J.N., Cavalli G. Biocidal polymers (II): determination of biological activity of novel N-halamine biocidal polymers and evaluation for use in water filters. React. Funct. Polym. 2008, 68:1448-1458.
8. Jang J., Kim Y. Fabrication of monodisperse silica-polymer core-shell nanoparticles with excellent antimicrobial efficacy. Chem. Commun. 2008, 34:4016-4018.
9. Akdag A., Okur S., McKee M.L., Worley S.D. The stabilities of N-Cl bonds in biocidal materials. J. Chem. Theory Comput. 2006, 2:879-884.
10. Sun Y., Sun G. Novel refreshable N-halamine polymeric biocides: N-chlorination of aromatic polyamides. Ind. Eng. Chem. Res. 2004, 43:5015-5020.
11. Hui F., Debiemme-Chouvy C. Antimicrobial N-halamine polymers and coatings: a review of their synthesis. Charact. Appl. Biomacromol. 2013, 14:585-601.
12. Kocer H.B., Akdag A., Worley S.D., Acevedo O., Broughton R.M., Wu Y. Mechanism of photolytic decomposition of N-halamine antimicrobial siloxane coatings. ACS Appl. Mater. Interfaces 2010, 2:2456-2464.
13. Sun Y., Sun G. Synthesis, characterization, and antibacterial activities of novel N-halamine polymer beads prepared by suspension copolymerization. Macromolecules 2002, 35:8909-8912.
14. Liu S., Sun G. Durable and regenerable biocidal polymers: acyclic N-halamine cotton cellulose. Ind. Eng. Chem. Res. 2006, 45:6477-6482.
15. Gouda M., Ibrahim N.A. New approach for improving antibacterial functions of cotton fabric. J. Ind. Text. 2008, 37:327-339.
16. Akdag A., McKee M.L., Worley S.D. Mechanism of formation of biocidal imidazolidin-4-one derivatives: an ab initio density-functional theory study. J. Phys. Chem. A 2006, 110:7621-7627.
17. Gnichwitz J.F., Marczak R., Werner F., Lang N., Jux N., Guldi D.M., Hirsch A. Efficient synthetic access to cationic dendrons and their application for ZnO nanoparticles surface functionalization: new building blocks for dye-sensitized solar cells. J. Am. Chem. Soc. 2010, 132:17910-17920.
18. Dong A., Zhang Q., Wang T., Wang W., Liu F., Gao G. Immobilization of cyclic N-halamine on polystyrene-functionalized silica nanoparticles: synthesis, characterization, and biocidal activity. J. Phys. Chem. C 2010, 114:17298-17303.
19. 4-functionalized nanoparticles with N-halamine and their magnetic/antibacterial properties. ACS Appl. Mater. Interfaces 2011, 3:4228-4235.
20. Dong A., Lan S., Huang J., Wang T., Zhao T., Wang W., Chen Y. Preparation of magnetically separable N-halamine nanocomposites for the improved antibacterial application. J. Colloid Interface Sci. 2011, 364:333-340.
21. Yan R., Zhang Y., Wang X., Xu J., Wang D., Zhang W. Synthesis of porous poly (styrene-co-acrylic acid) microspheres through one-step soap-free emulsion polymerization: whys and wherefores. J. Colloid Interface Sci. 2012, 368:220-225.
22. Shi M., Cui S.C. Transamidation catalyzed by a recoverable and reusable poly DMAP-based hafnium chloride and montmorillonite KSF. Synth. Commun. 2005, 35:2847-2858.
23. Mucsi Z., Chass G.A., Csizmadia I.G. Amidicity change as a significant driving force and thermodynamic selection rule of transamidation reactions. A synergy between experiment and theory. J. Phys. Chem. B 2008, 112:7885-7893.
24. Liang J., Chen Y., Ren X., Wu R., Barnes K., Worley S.D., Huang T.S. Fabric treated with antimicrobial N-halamine epoxides. Ind. Eng. Chem. Res. 2007, 46:6425-6429.
25. Jie Z.Q., Yan X.F., Zhao L.H., Worley S.D., Liang J. A high-efficacy and regenerable antimicrobial resin containing quaternarized N-halamine groups. React. Funct. Polym. 2013, 73:1580-1587.
26. Liu S., Zeng T.H., Hofmann M., Burcombe E., Wei J., Jiang R., Chen Y. Antibacterial activity of graphite, graphite oxide, graphene oxide, and reduced graphene oxide: membrane and oxidative stress. ACS Nano 2011, 5:6971-6980.
27. Chuayjuljit S., Piyawong N. Use of polystyrene nanoparticles synthesized by differential microemulsion polymerization for property improvement of (vinyl acetate)-ethylene copolymer. J. Vinyl Add. Tech. 2012, 18:216-221.
28. Yabu H., Kanahara M., Shimomura M., Arita T., Harano K., Nakamura E., Jinnai H. Polymer janus particles containing block-copolymer stabilized magnetic nanoparticles. ACS Appl. Mater. Interfaces 2013, 5:3262-3266.
29. Wang L.L., Zhang K., Xiong C.Y., Ge Z.G. Cytotoxicity of core-shell polystyrene magnetic beads and related mechanisms. Mol. Cell. Toxicol. 2012, 8:217-227.
30. Akelah A., Moet A. Polymer-clay nanocomposites: free-radical grafting of polystyrene on to organophilic montmorillonite interlayers. J. Mater. Sci. 1996, 31:3589-3596.
31. Chang L., Kong X., Wang F., Wang L., Shen J. Layer-by-layer assembly of poly (N-acryloyl-N'-propylpiperazine) and poly (acrylic acid): effect of pH and temperature. Thin Solid Films 2008, 516:2125-2129.
32. Cao Z., Sun Y. Polymeric N-halamine latex emulsions for use in antimicrobial paints. ACS Appl. Mater. Interfaces 2009, 1:494-504.
33. Fatiadi A.J., Isbell H.S. Phenylhydrazono-phenylazo tautomerism: Part II. Structures of 2-oxo-1,3-bis (phenylhydrazono) compounds and related compounds. Carbohydr. Res. 1967, 5:302-319.
34. Xu Z., Li C., Kang X., Yang D., Yang P., Hou Z., Lin J. Synthesis of a multifunctional nanocomposite with magnetic, mesoporous, and near-IR absorption properties. J. Phys. Chem. C 2010, 114:16343-16350.
35. Barnes K., Liang J., Wu R., Worley S.D., Lee J., Broughton R.M., Huang T.S. Synthesis and antimicrobial applications of 5,5'-ethylenebis [5-methyl-3-(3-triethoxysilylpropyl) hydantoin]. Biomaterials 2006, 27:4825-4830.
36. Zhu J., Bahramian Q., Gibson P., Schreuder-Gibson H., Sun G. Chemical and biological decontamination functions of nanofibrous membranes. J. Mater. Chem. 2012, 22:8532-8540.
37. Shrivastava S., Bera T., Roy A., Singh G., Ramachandrarao P., Dash D. Characterization of enhanced antibacterial effects of novel silver nanoparticles. Nanotechnology 2007, 18:225103.
38. Bryaskova R., Pencheva D., Kyulavska M., Bozukova D., Debuigne A., Detrembleur C. Antibacterial activity of poly (vinyl alcohol)-b-poly (acrylonitrile) based micelles loaded with silver nanoparticles. J. Colloid Interface Sci. 2010, 344:424-428.
39. Qi L., Xu Z., Jiang X., Hu C., Zou X. Preparation and antibacterial activity of chitosan nanoparticles[J]. Carbohydr. Res. 2004, 339:2693-2700.