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Journal of Materials Science

, Volume 42, Issue 11, pp 4018–4024 | Cite as

Synthesis, characterization, and antibacterial activities of novel N-halamine copolymers

  • Ying Chen
  • Li WangEmail author
  • Haojie Yu
  • Quan Shi
  • Xiaochen Dong
Article

Abstract

The synthesis and antibacterial properties of N-halamine copolymers are reported in this paper. 3-(4′-vinylbenzyl)-5,5-dimethylhydantoin (VBDMH) monomer and its copolymers with n-butyl methacrylate (BMA) were prepared under mild conditions. The effects of monomer feeds on the composition of the final copolymers and reaction conversion were investigated. It was found that VBDMH had higher reactivities than BMA in the copolymerization reactions and the reactivity ratios of VBDMH and BMA were calculated to be 8.91 and 0.42, respectively, according to the Fineman–Ross equation in the preparation of PBMA-co-VBDMH. Two chlorination methods were applied and compared in the process of polymers chlorination. After chlorination by tert-butyl hypochlorite, the polymers provided powerful antibacterial activities against Escherichia coli (E. coli). The surface morphologies of the chlorinated polymer films used in antibacterial assessment were observed by scanning electron microscope. The copolymers before and after chlorination were characterized with fourier transform infrared (FTIR) and 1H-nuclear magnetic resonance (1H-NMR). Their thermal properties were analyzed with thermogravimetric analysis (TGA) studies.

Keywords

Reactivity Ratio Sodium Hypochlorite Solution Hydantoin Initial Molar Ratio Final Copolymer 

Notes

Acknowledgements

The authors thank Yuanming Ying for performing the microbiological evaluation of the polymers.

References

  1. 1.
    Lin J, Winkelmann C, Worley SD, Kim J, Wei C-I, Cho U, Broughton RM, Santiago JI, Williams JF (2002) J Appl Polym Sci 85(1):177CrossRefGoogle Scholar
  2. 2.
    Chen Y, Wang L, Jiang S, Yu HJ (2003) J Polym Mater 20(3):279Google Scholar
  3. 3.
    Jiang S, Wang L, Yu HJ, Chen Y (2005) React Funct Polym 62:209CrossRefGoogle Scholar
  4. 4.
    Worley SD, Sun G (1996) Trends Polym Sci 4(11):364Google Scholar
  5. 5.
    Sun G, Chen TY, Habercom MS, Wheatley WB, Worley SD (1996) Water Res Bull 32:793CrossRefGoogle Scholar
  6. 6.
    Sun G, Chen TY, Worley SD (1996) Polymer 37:3753CrossRefGoogle Scholar
  7. 7.
    Worley SD, Sun G (1996) Polym Mater Encyclopedia 1:550Google Scholar
  8. 8.
    Eknoian MW, Putman JH, Worley SD (1998) Ind Eng Chem Res 37:2873CrossRefGoogle Scholar
  9. 9.
    Sun G, Xu X (1998) Textile Chem Colorist 30(6):26Google Scholar
  10. 10.
    Sun YY, Sun G (2001) J Polym Sci 39:3348CrossRefGoogle Scholar
  11. 11.
    Sun YY, Sun G (2001) J Appl Polym Sci 80:2460CrossRefGoogle Scholar
  12. 12.
    Sun YY, Sun G (2002) Macromolecules 35:8909CrossRefGoogle Scholar
  13. 13.
    Baumgarten HE (1973) Organic syntheses, vol. 5. John Wiley and Sons, New York, p 183Google Scholar
  14. 14.
    Fineman M, Ross SD (1950) J Polym Sci 5:259CrossRefGoogle Scholar
  15. 15.
    Hawkins WJ (1984) Polymer degradation and stabilization. Springer-Verlag, BerlinCrossRefGoogle Scholar
  16. 16.
    Xue GB (1986) Practical sterilization study, 2 edn. The People’s Military Medical Publishing Company, Shanghai, p 45Google Scholar
  17. 17.
    Chen YJ, Worley SD, Kim J, Wei CI, Chen TY, Suess J, Kawai H, Williams JF (2003) Ind Eng Chem Res 42:5715CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2007

Authors and Affiliations

  • Ying Chen
    • 1
  • Li Wang
    • 1
    Email author
  • Haojie Yu
    • 1
  • Quan Shi
    • 1
  • Xiaochen Dong
    • 1
  1. 1.State Key Laboratory of Polymer Reaction Engineering, College of Materials Science and Chemical EngineeringZhejiang UniversityHangzhouChina

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