Abstract
Novel block antibacterial polyurethane (BAPU) and terminated antibacterial polyurethane (TAPU) with N-methyl-N-dodecyl-N,N-bis(2-hydroxyethyl) ammonium bromide (C12QAS) were prepared through pre-polymerization, chain-extending and termination reactions. The physical performances of the antibacterial polyurethane (APU)s, including the film-building effect, differential scanning calorimetry, viscometry, mechanical properties and water absorption rate, were primarily investigated. Their antibacterial properties, tested by the inhibition zone method and the oscillation method, indicate that the APUs display marked mechanical properties, water absorption and improved antibacterial properties against Escherichia coli, Staphylococcus aureus and Bacillus subtilis, with the most potency against E. coli. This polyurethane material may have potential applications as an antibacterial material for biomedical devices and implants.
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References
Wang, H. H. & Lin, M. S. Biocidal polyurethane and its antibacterial properties. J. Polym. Res 5, 177–186 (1998).
Sakagami, Y., Horiguchi, K., Narita, Y., Sirithep, W., Morita, K. & Nagase, Y. Syntheses of a novel diol monomer and polyurethane elastomers containing phospholipid moieties. Polym. J. 45, 1159–1166 (2013).
Luo, J., Deng, Y. & Sun, Y. Y. Antimicrobial activity and biocompatibility of polyurethane-iodine complexes. J. Bioact. Compat. Pol. 25, 185–206 (2010).
Nagel, J. A., Dickinson, R. B. & Cooper, S. L. Bacterial adhesion to polyurethane surfaces in the presence of pre-adsorbed high molecular weight kininogen. J. Biomater. Sci. Polym. Ed. 7, 769–780 (1996).
Bakhshi, H., Yeganeh, H. & Mehdipour-Ataei, S. Synthesis and evaluation of antibacterial polyurethane coatings made from soybean oil functionalized with dimethylphenylammonium iodide and hydroxyl groups. J. Biomed. Mater. Res. A. 101, 1599–1611 (2013).
Nandakumar, V., Chittaranjan, S., Kurian, V. M. & Doble, M. Characteristics of bacterial biofilm associated with implant material in clinical practice. Polym. J. 45, 137–152 (2013).
Yung, L. Y., Colman, R. W. & Cooper, S. L. Neutrophil adhesion on polyurethanes preadsorbed with high molecular weight kininogen. Blood 94, 2716–2724 (1999).
Jain, P. & Pradeep, T. Potential of silver nanoparticle-coated polyurethane foam as an antibacterial water filter. Biotechnol. Bioeng. 90, 59–63 (2005).
Phong, N. T. P., Thanh, N. V. K & Phuong, P. H. Fabrication of antibacterial water filter by coating silver nanoparticles on flexible polyurethane foams. J. Phys. Conf. Ser. 187, 012079–012088 (2009).
Paladini, F., Cooper, I. R. & Pollini, M. Development of antibacterial and antifungal silver-coated polyurethane foams as air filtration units for the prevention of respiratory diseases. J. Appl. Microbiol. 116, 710–717 (2014).
Bakhshi, H., Yeganeh, H., Mehdipour-Ataei, S., Shokrgozar, M. A., Yari, A. & Saeedi-slami, S. N. Synthesis and characterization of antibacterial polyurethane coatings from quaternary ammonium salts functionalized soybean oil based polyols. Mater. Sci. Eng: C 33, 153–164 (2013).
Ma, T., Pradel, G., Ohlsen, K. & Holzgrabe, U. Quaternary ammonium salts and their antibacterial potential: targets or nonspecific interactions? Chem. Med. Chem. 7, 22–31 (2012).
Badawy, H. T., Pasetto, P., Mouget, J. L., Pilard, J. F., Cutright, T. J. & Milsted, A. Bacterial adhesion and growth reduction by novel rubber-derived oligomers. Biochem. Biophy. Res. Commun. 438, 691–696 (2013).
Shelton, R. S., Campen, M. G., Tilford, C. H., Lang, H. C., Nisonger, L., Bandelin, F. J. & Rubenkoenig, H. L. Quaternary ammonium salts as germicides. I. non-acylated quaternary ammonium salts derived from aliphatic amines. J. Am. Chem. Soc. 68, 753–755 (1946).
McDonnell, G. & Russell, A. D. Clin. Antiseptics and disinfectants: activity, action, and resistance. Microbiol. Rev. 12, 147–179 (1999).
Ma, S., Izutani, N., Imazato, S., Chen, J., Kiba, W., Yoshikawa, R., Takeda, K., Kitagawa, H. & Ebisu, S. Assessment of bactericidal effects of quaternary ammonium-based antibacterial monomers in combination with colloidal platinum nanoparticles. Dent. Mater. J. 31, 150–156 (2012).
Makino, M., Ohta, S. & Zenda, H. Effect of alkyl chain length of N-alkyl-N-(2-hydroxy-3-phenoxy)propyl-N,N-dimethyl ammonium butyl phosphate on the antibacterial activity. Yakugaku zasshi: J. Pharma. Soc. Japan 114, 73–79 (1994).
Liu, W. S., Wang, C. H., Sun, J. F., Hou, G. G., Wang, Y. P. & Qu, R. J. Synthesis, characterization and antibacterial properties of dihydroxy quaternary ammonium salts with long chain alkyl bromides. Chem. Biol. Drug. Des. 85, 91–97 (2015).
Besancon, B. M., Soles, C. L. & Green, P.F. Glass transition of miscible binary polymer-polymer thin films. Phys. Rev. Lett. 97 (5), 057801 (2006).
Hartmann, L, Gorbatschow, W, Hauwede, J & Kremer, F. Molecular dynamics in thin films of isotactic poly(methyl methacrylate). Eur. Phys. J. E. 8, 145–154 (2002).
Velankar, S. & Cooper, S. L. Microphase separation and rheological properties of polyurethane melts. 1. effect of block length, macromolecules. Macromolecules 31, 9181–9192 (1998).
Lcl, X. & Siedlecki, C. A. Microphase separation structure influences protein interactions with poly(urethane urea) surfaces. J Biomed. Mater. Res. A 92, 126–136 (2010).
Nagel-Baumgartner, J., Yang, C. Z. & Cooper, S. L. Physcial property analysis and bacterial adhesion on a series of phosphonated polyurethanes. Biomaterials 18, 831–837 (1997).
Ye, S. J., Majumdar, P., Chisholm, B., Stafslien, S. & Chen, Z. Antifouling and Antimicrobial mechanism of tethered quaternary qmmonium qalts in a cross-linked poly(dimethylsiloxane) matrix studied using sum frequency generation vibrational spectroscopy. Langmuir 26, 16455–16462 (2010).
Acknowledgements
We are grateful for the financial support from the National Natural Science Foundation of China (No. 21402010), the Foundation of Shandong province (Nos. ZR2014BL008, ZR2013BM022, 2015GGX102013, J11LF27) and the Foundation of Yantai (No. 2013ZH095, 2011076).
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Wang, CH., Hou, GG., Du, ZZ. et al. Synthesis, characterization and antibacterial properties of polyurethane material functionalized with quaternary ammonium salt. Polym J 48, 259–265 (2016). https://doi.org/10.1038/pj.2015.108
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DOI: https://doi.org/10.1038/pj.2015.108
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