Synthesis of antibacterial polymers from 2-dimethylamino ethyl methacrylate quaternized by dimethyl sulfate

Polymer Journal

Volumn 42, Issue 9, 2010, Pages 766-771

  Zuo, Huajiang ^a   Wu, Dingcai ^a   Fu, Ruowen ^a  

^a SUN YAT SEN UNIVERSITY   (China)

Author keywords

2 dimethylamino ethyl methacrylate; antibacterial; dimethyl sulfate; synthesis

Indexed keywords

ALKYL HALIDES; ANTI-BACTERIAL ACTIVITY; ANTIBACTERIAL; ANTIBACTERIAL POLYMERS; BIOCIDAL; CHEMICAL STRUCTURE; DIMETHYL SULFATES; DIMETHYLAMINO ETHYL METHACRYLATE; FOURIER TRANSFORM INFRARED; HIGH YIELD; HOMOPOLYMERS; LOWER COST; POTASSIUM PERSULFATE; QUATERNARY AMMONIUM; QUATERNARY AMMONIUM COMPOUND; QUATERNARY AMMONIUM SALT; QUATERNIZATION; SHAKING FLASKS; STAPHYLOCOCCUS AUREUS; SYNTHESIS; SYNTHETIC ROUTES; VISCOSITY METHOD;

ACRYLIC MONOMERS; AMMONIUM COMPOUNDS; BIOMATERIALS; ESCHERICHIA COLI; FOURIER TRANSFORMS; FREE RADICALS; MAGNETIC RESONANCE; POLYMERS;

FREE RADICAL POLYMERIZATION;

EID: 77956380766     PISSN: 00323896     EISSN: 13490540     Source Type: Journal    
DOI: 10.1038/pj.2010.63     Document Type: Article

References (28)

1. Hong, K., Liu, N. & Sun, G. UV-induced graft polymerization of acrylamide on cellulose by using immobilized benzophenone as a photo-initiator. Eur. Polym. J. 45, 2443-2449 (2009).
2. Roy, D., Knapp, J., Guthrie, J. & Perrier, S. Antibacterial cellulose fiber via RAFT surface graft polymerization. Biomacromolecules. 9, 91-99 (2008).
3. Ignatova, M., Voccia, S., Gilbert, B., Markova, N., Cossement, D., Gouttebaron, R., Jerome, R. & Jerome, C. Combination of electrografting and atom-transfer radical polymerization for making the stainless steel surface antibacterial and protein antiadhesive. Langmuir. 22, 255-262 (2006).
4. Voccia, S., Ignatova, M., Jerome, R. & Jerome, C. Design of antibacterial surfaces by a combination of electrochemistry and controlled radical polymerization. Langmuir. 22, 8607-8613 (2006).
5. Beyth, N., Yudovin-Farber, I., Bahir, R., Domb, A. & Weiss, E. Antibacterial activity of dental composites containing quaternary ammonium polyethylenimine nanoparticles against Streptococcus mutans. Biomaterials. 27, 3995-4002 (2006).
6. Lu, G., Kong, L., Sheng, B., Wang, G., Gong, Y. & Zhang, X. Degradation of covalently cross-linked carboxymethyl chitosan and its potential application for peripheral nerve regeneration. Eur. Polym. J. 43, 3807-3818 (2007).
7. Patel, J., Patel, S., Talpada, N. & Patel, H. Bioactive polymers: synthesis, release study and antimicrobial properties of polymer bound Ampicillin. Die. Angewandte. Makromolekulare. Chemie. 271, 24-27 (1999).
8. Anyaogu, K., Fedorov, A. & Neckers, D. Synthesis, characterization, and antifouling potential of functionalized copper nanoparticles. Langmuir. 24, 4340-4346 (2008).
9. Iconomopoulou, S. & Voyiatzis, G. The effect of the molecular orientation on the release of antimicrobial substances from uniaxially drawn polymer matrixes. J. Control. Release. 103, 451-464 (2005).
10. Sambhy, V., MacBride, M., Peterson, B. & Sen, A. Silver bromide nanoparticle/polymer composites: dual action tunable antimicrobial materials. J. Am. Chem. Soc. 128, 9798-9808 (2006).
11. Sauvet, G., Fortuniak, W., Kazmierski, K. & Chojnowski, J. Amphiphilic block and statistical siloxane copolymers with antimicrobial activity. J. Polym. Sci. Polym. Chem. 41, 2939-2948 (2003).
12. Kenawy, E., Abdel-Hay, F., El-Shanshoury, A. & El-Newehy, M. Biologically active polymers. V. Synthesis and antimicrobial activity of modified poly-(glycidyl methacrylate-co-2-hydroxy-ethyl methacrylate) derivatives with quaternary ammonium and phosphonium salts. J. Polym. Sci. Polym. Chem. 40, 2384-2393 (2002).
13. Marini, M., Bondi, M., Iseppi, R., Toselli, Z. & Pilati, F. Preparation and antibacterial activity of hybrid materials containing quaternary ammonium salts via sol-gel process. Eur. Polym. J. 43, 3621-3628 (2007).
14. Tiller, J., Liao, C., Lewis, K. & Klibanov, A. Designing surfaces that kill bacteria on contact. PNAS. 98, 5981-5985 (2001).
15. Matsugi, T., Saito, J., Kawahara, N., Matsuo, S., Kaneko, H., Kashiwa, N., Kobayashi, M. & Takahara, A. Surface modification of polypropylene molded sheets by means of surface-initiated ATRP of methacrylates. Polym. J. 41, 547-554 (2009).
16. Matsugi, T., Saito, J., Kawahara, N., Matsuo, S., Kaneko, H., Kashiwa, N., Kobayashi, M. & Takahara, A. Surface modification of polypropylene molded sheets by means of surface-initiated ATRP of methacrylates. Polym. J. 41, 547-554 (2009).
17. Domagk, G. A new class of disinfectants. Deut. Med. Wochenschr. 61, 829-832 (1935).
18. Pernak, J., Kalewska, J., Ksycinska, H. & Cybulski, J. Synthesis and anti-microbial activities of some pyridinium salts with alkoxymethyl hydrophobic group. Eur. J. Med. Chem. 36, 899-907 (2001).
19. Cheng, Z., Zhu, X., Shi, Z., Neoh, K. & Kang, E. Polymer microspheres with permanent antibacterial surface from surface-initiated atom transfer radical polymerization. Ind. Eng. Chem. Res. 44, 7098-7104 (2005). (Pubitemid 41312240)
20. Hu, F., Neoh, K., Cen, L. & Kang, E. Antibacterial and antifungal efficacy of surface functionalized polymeric beads in repeated applications. Biotechnol. Bioeng. 89, 474-484 (2005).
21. Kanazawa, A., Ikeda, T. & Endo, T. Polymeric phosphonium salts as a novel class of cationic biocides. II. Effects of counter anion and molecular weight on antibacterial activity of polymeric phosphonium salts. J. Polym. Sci. Polym. Chem. 31, 1441-1447 (1993). (Pubitemid 23637958)
22. Lu, G., Wu, D. & Fu, R. Studies on the synthesis and antibacterial activities of polymeric quaternary ammonium salts from dimethylaminoethyl methacrylate. React. Funct. Polym. 67, 355-366 (2007).
23. Tatsuo, T. Antibacterial and bacterium adsorbing macromolecules. Macromol. Mater. Eng. 286, 63-87 (2001).
24. Murata, H., Koepsel, R., Matyjaszewski, K. & Russell, A. Permanent, non-leaching antibacterial surfaces\2: how high density cationic surfaces kill bacterial cells. Biomaterials. 28, 4870-4879 (2007).
25. Kugler, R., Bouloussa, O. & Rondelez, F. Evidence of a charge-density threshold for optimum efficiency of biocidal cationic surfaces. Microbiology. 151, 1341-1348 (2005).
26. Ikeda, T., Hirayama, H., Ymaguchi, H., Tazuke, S. & Watanabe, M. Polycationic biocides with pendant active groups: molecular weight dependence of antibacterial activity. Antimicrob. Agents. Ch. 30, 132-136 (1986).
27. Lenoir, S., Pagnoulle, C., Galleni, M., Compere, P., Jerome, R. & Detrembleur, C. Poly-olefin matrixes with permanent antibacterial activity: preparation, antibacterial activity, and action mode of the active species. Biomacromolecules. 7, 2291-2296 (2006).
28. Kebir, N., Campistron, I., Laguerre, A., Pilard, J., Bunel, C. & Jouenne, T. Use of telechelic cis-1,4-polyisoprene cationomers in the synthesis of antibacterial ionic polyurethanes and copolyurethanes bearing ammonium groups. Biomaterials. 28, 4200-4208 (2007).