화학공학소재연구정보센터
홈 로그인 로그아웃 연락처 사이트맵
Macromolecular Research, Vol.27, No.7, 640-648, July, 2019
DOI10.1007/s13233-019-7084-6  Export Citation
Synthesis and Antibacterial Activities of Boronic Acid-Based Recyclable Spherical Polymer Brushes
Hüseyin Cicek†, Gokhan Kocak1, Ozggr Ceylan2, and Vural Butun3
  • Department of Chemistry, Mugla Sitki Kocman University, Mugla, 48000, Turkey
  • 1Department of Chemistry, Adiyaman University, Adiyaman, 02040, Turkey
  • 23Food Quality Control and Analysis Program, Ula Ali Kocman Vocational School, Mugla Sitki Kocman University, Mugla, Ula, 48147, Turkey
  • 3Department of Chemistry, Eskisehir Osmangazi University, Eskisehir, 26480, Turkey
E-mail:
Crosslinked poly(4-vinylbenzyl chloride) (PVBC) microbead was prepared by suspension polymerization. Various spherical polymer brushes (SPBs) were produced by grafting polymeric chains on their surfaces via surface initiated-atom transfer radical polymerization (SI-ATRP) using 4-vinylphenyl boronic acid (VPBA), 2-(dimethylamino)ethyl methacrylate (DMA), and quaternized DMA (QDMA). PVBC-g-PDMA, PVBC-g-PQDMA, PVBC-g-PVPBA, PVBC-g-P(VPBA-b-DMA), PVBC-g-P(VPBA-co-DMA) and PVBC-g-P(VPBA-b-QDMA) SPBs were characterized using nuclear magnetic resonance spectroscopy, attenuated total reflection Fourier transform infrared spectroscopy, thermogravimetric analysis, and scanning electron microscopy. Antibacterial activities of the synthesized SPBs were investigated against Escherichia coli and Staphylococcus aureus in nutrient and nutrient free media. Although PVBC-g-P(VPBA-b-DMA) SPB provided high antibacterial activity in the nutrient containing media due to its antibacterial, anti-biofilm and anti-QS properties, PVBC-g-P8QDMA SPB was found to be more effective in nutrient free media. Considering repeatable antibacterial activity, the PVBC-g-P(VPBA-b-8QDMA) SPB has advantageous over PVBC-g-P(VPBA-b-DMA) and PVBC-g-P8QDMA SPBs for long-term applications such as wastewater treatment in fluidized bad system.
Keywords:antibacterial microbead;suspension polymerization;SI-ATRP;spherical polymer brushes;4-vinylbenzyl chloride;4-vinylphenyl boronic acid;2-(dimethylamino)ethyl methacrylate
  1. Singh SK, Anamika J, Dipak S, Arti D, Der Chemica Sinica, 2, 111 (2011)
  2. Cheng ZP, Zhu XL, Shi ZL, Neoh KG, Kang ET, Ind. Eng. Chem. Res., 44(18), 7098 (2005)
  3. Cheng ZP, Zhu XL, Shi ZL, Neoh KG, Kang ET, Surf. Rev. Lett., 13, 313 (2006)
  4. Elsabee MZ, Abdou ES, Mater. Sci. Eng. C-Biomimetic Supramol. Syst., 33, 1819 (2013)
  5. Liu Y, Liu Y, Ren XH, Huang TS, Appl. Surf. Sci., 296, 231 (2014)
  6. Yu HP, Fu YC, Li G, Liu YX, Holzforschung, 67, 455 (2013)
  7. Roy D, Knapp JS, Guthrie JT, Perrier S, Biomacromolecules, 9(1), 91 (2008)
  8. Tang F, Zhang LF, Zhang ZB, Cheng ZP, Zhu XL, J. Macromol. Sci. A, 46, 989 (2009)
  9. Limpiteeprakan P, Babel S, Environ. Monit. Assess, 188 (2016)
  10. Siedenbiedel F, Tiller JC, Polymers, 4, 46 (2012)
  11. Maharaj LL, Gupta MM, Gadad AK, World J. Pharm. Pharm. Sci., 4, 126 (2015)
  12. Edmondson S, Armes SP, Polym. Int., 58, 307 (2009)
  13. Mittal V, Polymers, 2, 40 (2010)
  14. Suzuki H, Murou M, Kitano H, Ohno K, Saruwatari Y, Colloids Surf. B: Biointerfaces, 84, 111 (2011)
  15. Xu FJ, Yuan SJ, Pehkonen SO, Kang ET, Neoh KG, NanoBioNanoBiotechnology, 2, 123 (2006)
  16. Khabibullin A, Mastan E, Matyjaszewski K, Zhu SP, in Controlled Radical Polymerization at and from Solid Surfaces, P. Vana, Ed. Vol. 270, pp 29-76 2016.
  17. Fristrup CJ, Jankova K, Hvilsted S, Soft Matter, 5, 4623 (2009)
  18. Brooks BW, Chem. Eng. Technol., 33(11), 1737 (2010)
  19. Charnley M, Textor M, Acikgoz C, React. Funct. Polym., 71(3), 329 (2011)
  20. Gokmen MT, Du Prez FE, Prog. Polym. Sci, 37, 365 (2012)
  21. Hu FX, Neoh KG, Cen L, Kang ET, Biotechnol. Bioeng., 89(4), 474 (2005)
  22. Kugel AJ, Ebert SM, Stafslien SJ, Hevus I, Kohut A, Voronov A, Chisholm BJ, React. Funct. Polym., 72(1), 69 (2012)
  23. Senel S, Cicek H, Tuncel A, J. Appl. Polym. Sci., 67(7), 1319 (1998)
  24. Slomkowski S, Basinska T, Macromol. Symp., 295, 13 (2010)
  25. Tomovska R, de la Cal JC, Asua JM, in Monitoring Polymerization Reactions, John Wiley & Sons, pp 59-77 2013.
  26. Lee SB, Koepsel RR, Morley SW, Matyjaszewski K, Sun YJ, Russell AJ, Biomacromolecules, 5(3), 877 (2004)
  27. Lu GQ, Wu DC, Fu RW, React. Funct. Polym., 67(4), 355 (2007)
  28. Murata H, Koepsel RR, Matyjaszewski K, Russell AJ, Biomaterials, 28, 4870 (2007)
  29. Timofeeva L, Kleshcheva N, Appl. Microbiol. Biotechnol., 89(3), 475 (2011)
  30. Zeng FQ, Shen YQ, Zhu SP, Pelton R, J. Polym. Sci. A: Polym. Chem., 38(20), 3821 (2000)
  31. Baker SJ, Ding CZ, Akama T, Zhang YK, Hernandez V, Xia Y, Future Medicinal Chemistry, 1, 1275 (2009)
  32. Chang YJ, Liu XZ, Zhao Q, Yang XH, Wang KM, Wang Q, Lin M, Yang M, Chinese Chem. Lett., 26, 1203 (2015)
  33. Elmas B, Onur MA, Senel S, Tuncel A, Colloid Polym. Sci., 280, 1137 (2002)
  34. Li XB, Pennington J, Stobaugh JF, Schoneich C, Anal. Biochem., 372, 227 (2008)
  35. Lin Z, Huang H, Li SH, Wang J, Tan XQ, Zhang L, Chen GN, J. Chromatogr. A, 1271, 115 (2013)
  36. Senel S, Colloids Surf. A: Physicochem. Eng. Asp., 219, 17 (2003)
  37. Zhang J, Ni YL, Zheng XL, J. Sep. Sci., 38, 81 (2015)
  38. Adamczyk-Wozniak A, Komarovska-Porokhnyavets O, Misterkiewicz B, Novikov VP, Sporzynski A, Appl. Organomet. Chem., 26, 390 (2012)
  39. Ni NT, Chou HT, Wang JF, Li MY, Lu CD, Tai PC, Wang BH, Biochem. Biophys. Res. Commun., 369(2), 590 (2008)
  40. Kocak G, Cicek H, Ceylan O, Butun V, J. Appl. Polym. Sci., 136, 46907 (2019)
  41. Cicek H, Kocak G, Ceylan O, Kutluca EA, Dikmen Z, Butun V, J. Appl. Polym. Sci., 135, 46245 (2018)
  42. Yavuz E, Bayramoglu G, Senkal BF, Arica MY, J. Appl. Polym. Sci., 113(4), 2661 (2009)
  43. Man Y, Peng G, Lv XF, Liang YL, Wang Y, Chen Y, Deng YL, Chromatographia, 78, 157 (2015)
  44. Yancheva E, Paneva D, Maximova V, Mespouille L, Dubois P, Manolova N, Rashkov I, Biomacromolecules, 8(3), 976 (2007)
  45. Suart B, Infrared Spectroscopy: Fundamental and Applications, John Wiley & Sons, Ltd, 2004.
  46. Kahraman G, Beskardes O, Rzaev ZMO, Piskin E, Polymer, 45(17), 5813 (2004)
  47. Cetinkaya O, Duru ME, Cicek H, J. Chromatogr. B, 909, 51 (2012)
  48. Lu WT, Shao ZG, Zhang G, Zhao Y, Yi BL, J. Power Sources, 248, 905 (2014)
  49. Song JM, Lee SY, Woo HS, Sohn JY, Shin J, J. Polym. Sci. B: Polym. Phys., 52(7), 517 (2014)
  50. Karamitrou M, Sarpaki E, Bokias G, J. Appl. Polym. Sci., 133 (2016)
  51. Roy D, Guthrie JT, Perrier S, Soft Matter, 4, 145 (2008)
  52. Wiacek M, Wesolek D, Rojewski S, Bujnowicz K, Schab-Balcerzak E, Polym. Adv. Technol., 26, 49 (2015)
  53. King A, Chakrabarty S, Zhang W, Zeng XM, Ohman DE, Wood LF, Abraham S, Rao R, Wynne KJ, Biomacromolecules, 15(2), 456 (2014)
  54. Filip Z, Hermann S, Demnerova K, Czech J. Food Sci., 26, 458 (2008)
  55. D'Souza L, Devi P, Kamat T, Naik CG, Indian J. Mar. Sci., 38, 45 (2009)
  56. Ashfaq M, Khan S, Verma N, Biochem. Eng. J., 90, 79 (2014)