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研究生:林蕙芬
研究生(外文):Hui-Fen Lin
論文名稱:高分子聚醚多胺衍生物之界面性質與抗菌機制探討
論文名稱(外文):Amphiphilic Aggregation and Antibacterial Behaviors of Poly(oxyalkylene)-Polyamine-Salts
指導教授:林江珍
學位類別:碩士
校院名稱:國立臺灣大學
系所名稱:高分子科學與工程學研究所
學門:工程學門
學類:化學工程學類
論文種類:學術論文
論文出版年:2010
畢業學年度:98
語文別:英文
論文頁數:44
中文關鍵詞:四級胺鹽抗菌微胞界面活性劑局部濃度
外文關鍵詞:quaternary ammonium saltsantibacterialmicellesurfactantlocal concentration
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在過去十年期間,抗菌材料發展受到很大的重視,其中以四級胺鹽被廣泛使用。本篇論文是利用本實驗室發明之高分子聚醚多胺 (polyamine)衍生物進行抗菌機制深討。首先分別利用poly(oxypropylene)-diamine 和triamine (POP-amine)與2,2-Bis[4-(glycidyloxy)phenyl]propane (DGEBA)進行偶合反應,製備出D400-terminating epoxy oligomers (DEO) and T403-terminating epoxy oligomers (TEO) 二種高分子聚醚多胺,高分子聚醚多胺擁有6個可酸化的胺基,利用鹽酸酸化不同比例1/6、3/6、6/6 (H+/amine equiv) 後,得到具有不同親疏水性的四級胺鹽。此論文中,我們利用表面張力儀得知親疏水性及界面活性劑的特性,並利用粒徑分析儀及穿透式電子顯微鏡觀察微胞的大小,發現酸化比例愈高時,微胞愈小。另外,對不同酸化比例的四級胺鹽進行抗菌測試,結果得知,當酸化比例愈高時,抗菌效果愈差。此外,利用掃描式電子顯微鏡去觀察四級胺鹽對大腸桿菌 (E. coli ) 及金黃色葡萄球菌 (S. aureus) 形態上的變化。綜合以上結果,可以推測抗菌機制與微胞大小有關,微胞大小則影響到接觸到細菌表面的局部濃度有關。此外,將我們合成的四級胺鹽與一般常用的抗菌劑比較,將具有調控親疏水性的功能及較好的抗菌效果。

Oligomeric amines were synthesized from the coupling reaction of poly(oxypropylene)-diamine and triamine (POP-amine) with 2,2-Bis[4-(glycidyloxy)phenyl]propane (DGEBA). Various equivalent amounts of acidification with hydrogen chloride at the acidified ratio of H+/amine equiv ratios rendered the oligomers with specific amphiphilic aggregations in water and antibacterial activity. The polyamine salts behave as a surfactant and exhibit the capability of surface tension until 47 mN/m at 0.01 wt %. Laser particle size analyzer and transmission electronic microscopy (TEM) results that polyamine salts at different acid ratios have the different micelle sizes, and further provide a large concentration on bacteria. The oligomers exhibited antibacterial activity against Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) at the minimum bactericidal concentration (MBC) of 1 μg/mL. Scanning electron microscope (SEM) revealed that polyamine salts confirmed morphological changes and the treated bacteria were damaged. Comparisons between poly(oxypropylene)- and poly(oxyethylene)-backbones for the oligomers had correlated the antibacterial properties that closely related to the different sizes of the micelle formation and the polyvalent ionic sites when interacting with bacteria. A comparison of the commercial product quaternary ammonium salts (QAS) ABLUMINE 1214, the polyamine salts displayed potent antibacterial activity.

Acknowledgements …………………………………………………………... Ι
中文摘要 Ⅱ
Abstract Ⅲ
Figure captions …………………………………………………………... Ⅶ
Table captions …………………………………………………………... Ⅷ

Chapter 1 Introduction…………………………... 1

Chapter 2 Literature Background………...…….………………….. 5
2-1 Application of antibacterial polymer...……….... 5
2-2 Mechanism of quaternary ammonium salts …... 6
2-3 Factors affecting the antibacterial activity……… 7
2-4 The difference in structure of cell walls between gram-positive and gram-negative bacteria……… 9

Chapter 3 Experimental………………………………………......... 11
3-1 Materials..……………………………………….. 11
3-2 Preparation of polyamines………………………. 12
3-3 Antibacterial activity tests…………….……........ 14
3-4 SEM of bacteria incubated with polyamine salts.. 15
3-5 Statistical analysis…………….…………............ 16
3-6 Characterization and Instruments……………….. 16

Chapter 4 Results and discussion…………………………………... 18
4-1 Dispersive and surfactant property of polyamine salts..………………………………...………....... 18
4-2 Emulsify micelle size of polyamines acidifies at different ratios……………................................... 21
4-3.1 Antibacterial activity of Polyamine Salts………. 24
4-3.2 Antibacterial activity of Jaffamine series and ABLUMINE 1214………………….................... 28
4-4 Scanning electron microscopy of bacteria incubated with polyamine salts………………… 31
4-5 Proposed antibacterial mechanism for polyamine salts…................................................................... 33

Chapter 6 Conclusion…………………………………………......... 36
Chapter 7 References...…………………………………………….. 37


(1) Nel, A.; Xia, T.; Ma¨dler, L.; Li, N. Science 2006, 311, 622–627.
(2) Nqvqrro, E.; Piccapietra, F.; Wagner, B.; Marconi, F.; Kaegi, R.; Odzak, N.; Sigg, L.; Behra, A. Environ. Sci. Technol. 2008, 42, 8959–8964.
(3) Yang, H.; Liu, C.; Yang, D. Zhang, H.; Xi, Z. J. Appl. Toxicol. 2009, 29, 69–78.
(4) Lin, J. J.; Chu, C. C.; Chiang, M. L.; Tsai. W. C. J. Phys. Chem. B. 2006, 110, 18115–18120.
(5) Aeschlimann, J. R.; Dresser, L. D.; Kaatz, G. W.; Rybak, M. J. Antimicrob. Agents Chemother. 1999, 43, 335–340.
(6) Ikeda, T.; Yamaguchi, H.; Tazuke, S. Antimicrob. Agents Chemother. 1984, 26, 139–144.
(7) Kenawy, E.; Abdel-Hay, F. I.; El-Raheem, A.; El-Shanshoury, R.; El-Newehy, M. H. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 2384–2393.
(8) Dizman, B.; Elasri, M. O.; Mathias, L. J. Biomacromolecules, 2005, 6, 514–520.
(9) Parshikov, I. A.; Freeman, J. P.; Lay, J. J. O.; Beger, R. D.; Williams, A. J.; Sutherland, J. B. Appl. Environ. Microbiol. 2000, 66, 2664–2667.
(10) Golet, E. M.; Alder, A. C.; Hartmann, A.; Ternes, T. A.; Giger, W. Anal. Chem. 2001, 73, 3632–3638.
(11) Biagini, G. A.; Richier, E.; Bray, P. G.; Calas, M.; Vial, H.; Ward, S. A. Antimicrob. Agents Chemother. 2003, 47, 2584–2589.
(12) Darouiche, R. O.; Mansouri, M. D.; Raad, I. I. Urology 2002, 59, 303–307.
(13) Chung, D. H.; Papadakis, S. E.; Yam, K. L. Int. J. Food Sci. Technol. 2003, 38, 165–169.
(14) Klueh, U.; Wagner, V.; Kelly, S.; Johnson, A.; Bryers, J. D. J. Biomed. Mater. Res., Part B 2000, 53, 621–631.
(15) Johnson, J. R.; Roberts, P. L.; Olsen, R. J.; Moyer, K. A.; Stamm, W. E. J. Infect. Dis. 1990, 162, 1145–1150.
(16) Isquith, A. J.; Abbott, E. A.; Walters, P. A. Appl. Microbiol. 1972, 24, 859–863.
(17) Nurdin, N.; Helary, G.; Sauvet, G. J. Appl. Polym. Sci. 1993, 50, 663–670.
(18) Grapski, J. A.; Cooper, S. L. Biomaterials 2001, 22, 2239–2246.
(19) Tiller, J. C.; Liao, C. J.; Lewis, K.; Klibanov, A. M. P. Natl. Acad. Sci. U.S.A. 2001, 98, 5981–5985.
(20) Gottenbos, B.; van der Mei, H. C.; Klatter, F.; Nieuwenhuis, P.; Busscher, H. J. Biomaterials 2002, 23, 1417–1423.
(21) Lee, S. B.; Koepsel, R. R.; Morley, S. W.; Matyjaszewski, K.; Sun, Y. J.; Russell, A. J. Biomacromolecules 2004, 5, 877–882.
(22) Cen, L.; Neoh, K. G.; Kang, E. T. Langmuir 2003, 19, 10295–10303.
(23) Tiller, J. C.; Lee, S. B.; Lewis, K.; Klibanov, A. M. Biotechnol. Bioeng. 2002, 79, 465–471.
(24) Kanazawa, A.; Ikeda, T.; Endo, T. J. Polym. Sci., Part A: Polym. Chem. 1993, 31, 1467–1472.
(25) Popa, A.; Davidescu, C. M.; Trif, R.; Ilia, G.; Iliescu, S.; Dehelean, G. React. Funct. Polym. 2003, 55, 151–158.
(26) Denyer, S. P. Int. Biodeterior. Biodegrad. 1995, 36, 227–245.
(27) Gabrielska, J.; Sarapuk, J.; Przestalski, S.; Wroclaw, P. Tenside Surfact. Det. 1994, 31, 296–298.
(28) Przestalski, S.; Sarapuk, J.; Kleszczynska, H.; Gabrielska, J.; Hladyszowski, J.; Trela, Z.; Kuczera, J. Acta Biochim. Pol. 2000, 47, 627–638.
(29) Franklin, T. J.; Snow, G. A. Biochemistry of Antimicrobial Action; Chapman and Hall: London, 1981.
(30) Tashiro, T. Macromol. Mater. Eng. 2001, 286, 63–87.
(31) Domagk, G. Dtsch. Med. Wochenschr. 1935, 61, 829–832.
(32) Birnie, C.R.; Malamud, D.; Schnaare, R.L. Antimicrob. Agents Chemother. 2000, 44, 2514–2517.
(33) Sauvet, G.; Dupond, S.; Kazmierski, K.; Chojnowski, J. J. Appl. Polym. Sci. 2000, 75, 1005–1012.
(34) Borman, S. Sci. Tech. 2002, 80, 36.
(35) Goodson, B.; Ehrhardt, A.; Ng, S.; Nuss, J.; Johnson, K.; Giedlin, M.; Yamamoto, R.; Moos, W. H.; Krebber, A.; Ladner, M.; Giacona, M. B.; Vitt, C.; Winter, J. Antimicrob. Agents Chemother. 1999, 43, 1429–1434.
(36) Block, S. S. Disinfection, Sterilization and PreserVation; 4th ed.; Lea & Febiger: Philadelphia, 1991.
(37) Chu, C. C.; Chiang, M. L.; Tsai, C. M.; Lin, J. J. Macromolecules 2005, 38, 6240–6243.
(38) Lin, J. J. Chu, C. C.; Chou, C. C.; Shieu, F. S. Adv. Mater. 2005, 17, 301–304.
(39) Lin, J. J. Chu, C. C.; Chiang, M. L.; Tsai. W. C. Adv. Mater. 2006, 18, 3248–3252.
(40) Block, S. Disinfection, Sterilization and PreserVation, 3rd ed.; Lea & Febiger: Philadelphia, PA, 1983.
(41) Woo, G. L. Y.; Yang, M. L.; Yin, H. Q.; Jaffer, F.; Mittelman, M. W.; Santerre, J. P. J. Biomed. Mater. Res. 2002, 59, 35–45.
(42) Acharya, V.; Prabha, C. R.; Narayanamurthy, C. Biomaterials 2004, 25, 4555–4562.
(43) Jiang, H.; Manolache, S.; Lee Wong, A. C.; Denes, F. S. J. Appl. Polym. Sci. 2004, 93, 1411–1422.
(44) Hume, E. B. H.; Baveja, J.; Muir, B.; Schubert, T. L.; Kumar, N.; Kjelleberg, S.; Griesser, H. J.; Thissen, H.; Read, R.; Poole-Warren, L. A.; Schindhelm, K.; Willcoxy, M. D. P. Biomaterials 2004, 25, 5023–5030.
(45) Baveja, J. K.; Li, G.; Nordon, R. E.; Hume, E. B. H.; Kumar, N.; Willcox, M. D. P.; Poole-Warren, L. A. Biomaterials 2004, 25, 5013–5021.
(46) Vigo, T. L. In Biotechnol. Bioact. Polym. [Proc. Am. Chem. Soc. Symp.]; Gebelein, C., Carraher, C., Eds.; Plenum Press: New York, 1994; pp 225–237.
(47) Ikeda, T.; Tazuke, S.; Suzuki, Y. Macromol. Chem. Phys. 1984, 185, 869–876.
(48) Baudrion, F.; Perichaud, A.; Coen, S. J. Appl. Polym. Sci. 1998, 70, 2657–2666.
(49) Kenawy, E. R.; Abdel-Hay, F. I.; El-Raheem, A.; El-Shanshoury, R.; El-Newehy, M. H. J. Controlled Release 1998, 50, 145–152.
(50) Chen, C. Z. S.; Beck-Tan, N. C.; Dhurjati, P.; van Dyk, T. K.; LaRossa, R. A.; Cooper, S. L. Biomacromolecules 2000, 1, 473–480.
(51) Dizman, B.; Elasri, M. O.; Mathias, L. J. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 5965–5973.
(52) Eren, T.; Som, A.; Rennie, J. R.; Nelson, C. F.; Urgina, Y.; Nusslein, K.; Coughlin, E. B.; Tew, G. N. Macromol. Chem. Phys. 2008, 209, 516–524.
(53) Rozga-Wijas, K.; Mizerska, U.; Fortuniak, W.; Chojnowski, J.; Halasa, R.; Werel, W. J. Inorg. Organomet. Polym. Mater. 2007, 17, 605–613.
(54) Kenawy, E. R.; Worley, S. D.; Broughton, R. Biomacromolecules 2007, 8, 1359–1384.
(55) Chauhan, G.S., Singh, B., Dhiman, S.K. J. Appl. Polym. Sci .2004, 91, 2454–2464.
(56) Lin, J.; Tiller, J. C.; Lee, S. B.; Lewis, K.; Klibanov, A. M. Biotechnol. Lett. 2002, 24, 801–805.
(57) Chen, J. C.; Yeh, J. T.; Chen, C. C. J. Appl. Polym. Sci. 2003, 90, 1662–1669.
(58) Seong, H. S.; Whang, H. S.; Ko, S. W. J. Appl. Polym. Sci. 2000, 76, 2009–2015.
(59) Kim, J. Y.; Lee, J. K.; Lee, T. S.; Park, W. H. Int. J. Biol. Macromol. 2003, 32, 23–27.
(60) Thorsteinsson, T.; Masson, M.; Kristinsson, K. G.; Hjalmarsdottir, M. A.; Hilmarsson, H.; Loftsson, T. J. Med. Chem. 2003, 46, 4173–4181.
(61) Lin, J.; Murthy, S. K.; Olsen, B. D.; Gleason, K. K.; Klibanov, A. M. Biotechnol. Lett. 2003, 25, 1661–1665.
(62) Lenoir, S.; Pagnoulle, C.; Galleni, M.; Compere, P.; Jerome, R.; Detrembleur, C. Biomacromolecules 2006, 7, 2291–2296.
(63) Ikeda, T.; Hirayama, H.; Suzuki, K.; Yamaguchi, H.; Tazuke, S. Makromol. Chem. 1986, 187, 333–340.
(64) Rahn, O.; Van Eseltine, W. P. Bacteriol. ReV. 1947, 1, 173–192.
(65) Panarin, E. F.; Solovaskii, M. V.; Zaikina, N. A.; Afinogenov, G. E. Makromol. Chem. Suppl. 1985, 9, 25–33.
(66) Kanazawa, A.; Ikeda, T.; Endo, T. J. Polym. Sci., Part A: Polym. Chem. 1993, 31, 2873–2876.
(67) Kanazawa, A.; Ikeda, T.; Endo, T. J. Polym. Sci., Part A: Polym. Chem. 1993, 31, 335–343.
(68) Ikeda, T.; Yamaguchi, H.; Tazuke, S. J. Bioact. Compact. Polym. 1990, 5, 31–41.
(69) Dizman, B.; Elasri, M. O.; Mathias, L. J. J. Appl. Polym. Sci. 2004, 94, 635–642.
(70) Kanazawa, A.; Ikeda, T.; Endo, T. J. Polym. Sci., Part A: Polym. Chem. 1993, 31, 3031–3038.
(71) Costerton, J. W.; K.-J. Cheng. J. Antimicrob. Chemother. 1975, 1, 363–377.
(72) Campbell N. Biology, 1993. 3rd ed. Redwood city, CA: Benjamin Cummings Publishing. p. 517.
(73) Brooks G, Butel J, Ornston L. 1991. Jawetz Melnick and Adelberg''s Medical Microbiology, 19th ed. Norwalk, CT: Appleton and Lange. pp. 15–20.
(74) Chiu, C.W.; Chu, C.C.; Cheng W. T.; Lin, J. J. European Polymer Journal 2008, 44, 628–636.
(75) Hansen, H. C.; Haataja, S.; Finne, J.; Magnusson, G. J. J. Am. Chem. Soc. 1997, 119, 6974–6979.
(76) Dizman, B.; Badger, J. C.; Elasri, M. O.; Mathias, L. J. Appl. Clay Sci. 2007, 38, 57–63.


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1. 王崧興,〈濁大流域的民族學研究〉,《中央研究院民族學研究所集刊》,期36(1973年),頁1-10。
2. 王世慶,〈日據初期臺灣之降筆會與戒煙運動〉,《臺灣文獻》,卷37期4 (1986年12月),頁111-151。
3. 吳文星,〈日據時代臺灣書房之研究〉,《思與言》,卷16期3(1978 年9 月),頁264-291。
4. 石再添、黃朝恩、張瑞津、鄧國雄,〈濁大流域的聚落分布與地形之相關研究〉,《臺灣文獻》卷28期2(1977年6月),頁75-94。
5. 王世慶,〈十九世記中葉臺灣北部農村金融之研究:以興直堡銀主小租戶廣記為例〉,《臺灣文獻》,卷39期2(1988年6月),頁1-48。
6. 吳文星,〈日據時代臺灣書房教育之再檢討〉,《思與言》,卷26 期1(1988 年5月),頁101-108。
7. 吳文星,〈日據時期臺灣總督府推廣日語運動初探(上)〉,《臺灣風物》卷37期1(1987年3月),頁1-31。
8. 吳文星,〈日據時期臺灣總督府推廣日語運動初探(下)〉,《臺灣風物》卷37期4(1987年12月),頁53-86。
9. 吳學明,〈清代一個務實拓墾家族的研究:以新竹姜朝鳳家族為例〉,《臺灣史研究》,卷2期2(1995年12月),頁5-52。
10. 李壬癸,〈臺灣平埔族的種類及其相互關係〉,《臺灣風物》,卷42期1(1992年3月),頁211-238。
11. 李弘毅,〈西螺今古觀〉,《雲林文獻》,輯36(1992年5月),頁32-35。
12. 林寶安,〈日據時期臺灣的信用組合與地方社會〉,《臺灣銀行季刊》,卷44期3(1993年9月),頁81-100。
13. 胡忠一,〈日據時期臺灣產業組合與農業會之研究〉,《農民組織學刊》,期2(1997年6月),頁31-90。
14. 張伊倫,〈古老的發酵食品-醬油〉,《食品工業月刊》,卷29期4(1997年4月),頁65-72。
15. 張瑞津,〈濁水溪沖積扇河道變遷之探討〉,《臺灣師範大學地理學研究》,期7(1983年10月),頁85-100。
 
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