Please use this identifier to cite or link to this item: http://hdl.handle.net/11455/3807
標題: 以含側鏈規則樹枝狀分子之聚胺酯製備蜂窩狀薄膜
Honeycomb-like Polymeric Films Based on Dendritirc Side-Chain Polyurethanes
作者: 葉峻銘
葉峻銘, Chun-Ming Yeh
關鍵字: dendrimer
規則樹枝狀高分子
breath-figure
honeycomb structrure
breath-figure
蜂窩狀結構
出版社: 化學工程學系所
引用: 1. Buchlein, E.; Wehner, W.; Vögtle, F. Synthese 1978, 155. 2. Xia, L.; Jian, L. Adv. Mater. 2008, 20, 2842. 3. Rayleigh, L. Nature 1911, 86, 416. 4. Rayleigh, L. Nature 1912, 90, 436. 5. Widawski, G.; Rawiso, M.; François, B. Nature 1994, 369, 387. 6. Stenzel, M. H.; Barner-Kowollik, C.; Davis, T. P. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 2363. 7. Yabu, H.; Shimomura, M.; Langmuir 2005, 21, 1709. 8. Karthaus, O.; Maruyama, N.; Cieren, X.; Shimomura, M.; Hasegawa, H.; Hishimoto, T. Langmuir 2000, 16, 6071. 9. Srinivasarao, M.; Collings, D.; Philips, A.; Patel, S. Science 2001, 292, 79. 10. Lord, H. T.; Quinn, J. F.; Angus, S. D.; Whittaker, M. R.; Stenzel, M. H.; Davis, T. P. J. Mater. Chem. 2003, 13, 2819. 11. Francois, B.; Ederlé , Y.; Mathis, C. Synth Met 1999, 103, 2362. 12. Connal, L. A.; Vestberg, R.; Gurr, P. A.; Hawker, C. J.; Qiao, G. G. Langmuir 2008, 24, 556. 13. Wong, K. H.; Davis, T. P.; Barner-Kowollik, C.; Stenzel, M. H. Aust. J. Chem. 2006, 59, 539. 14. Wong, K. H.; Davis, T. P.; Barner-Kowollik, C.; Stenzel, M. H. Polymer 2007, 48, 4950. 15. Song, L.; Bly, R. K.; Wilson, J. N.; Babak, S.; Park, J. O.; Srinivasarao, M.; Bunz, U. H. F. Adv. Mater. 2004, 16, 115. 16. Hernandez-Guerrero, M.; Min, E. H.; Barner-Kowollik, C.; Muller, A. H. E.; Stenzel, M. H. J. Mater. Chem. 2008, 18, 4718. 17. Bormashenko, E.; Schechter, A.; Stanevsky, O.; Stein, Tamir.; Balter, S.; Musin, A.; Bormashenko, Y.; Pogred, R.; Barkay, Z.; Aurbach, D. Macromol. Mater. Eng. 2008, 293, 872. 18. Nomura, E.; Hosoda, A,; Takagaki, H.; Miyake, Y.; Shibakami, M.; Taniguchi H. Langmuir 2010, 26, 10266. 19. Haswell, S. J.; Skelton, V. Trends Anal. Chem. 2000, 19, 389. 20. Beattie, D.; Wong, K. H.; Williams, C.; Poole-Warren, L. A.; Davis, T. P.; Barner-Kowollik, C.; Stenzel, M. H. Biomacromolecules 2006, 7, 1072. 21. Li, L.; Chen, C.; Li, C.; Zhang, A.; Liu, X.; Xu, B.; Gao, S.; Jin, G.; Ma, Z. J. Mater. Chem. 2009, 19, 2789. 22. Song, L.; Bly, R. K.; Wilson, J. N.; Bakbak, S.; Park, J. O.; Srinivasarao, M.; Bunz, U. H. F. Adv. Mater. 2004, 16, 115. 23. Imada, M.; Noda, M. S.; Chutinan, A.; Tokuda, T.; Murata, M.; Sasaki, G. Appl. Phys. Lett. 1999, 75, 316. 24. Barner-Kowollik, C.; Dalton, H.; Davis, T. P.; Stenzel, M. H.; Angew. Chem. Int. Ed. 2003, 42, 3664. 25. Oertel, G. Polyurethane Handbook, Hanser/Gardner Publications Inc, New York, 1993. 26. Fambri, L.; Penati, A.; Kolarik, J. Polymer 1997,38, 835. 27. Bosman, A. W.; Janssen, H. M.; Weijer, E. W. Chem. Rev. 1999, 99, 1665. 28. Grayson, S. M.; Fréchet, J. M. J. Chem. Rev. 2001, 101, 3819. 29. Esfand, R.; Tomalia, D. A. Drug. Discov. Today 2001, 6, 427. 30. Namazi, H.; Adeli, M. Biomaterials 2005, 26, 1175. 31. Piotti, M. E.; Rivera, Jr., F.; Bond, R.; Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1999, 121, 9471. 32. Joralemon, M. J.; O’Reilly, Matson, J. B.; Nugent, A. K,; Hawker, C. J.; Wooley, K. L. Macromolecules 2005, 38, 5436. 33. Chen, C. P.; Dai, S. A.; Chang, H. L.; Su, W. C.; Jeng, R. J. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 682. 34. Tsai, C. C.; Juang, T. Y.; Dai, S. A.; Wu, T. M.; Su, W. C.; Liu, Y. L.; Jeng, R. J. J. Mater. Chem. 2006, 16, 2056. 35. Stockmayer, W. H. J. Chem. Phys. 1944, 263, 1710. 36. Flory, P. J. J. Chem. Phys. 1943, 11, 512. 37. Tomalia, D. A. ; Baker, H.; Dewald, J.; Hall, M.; Kallos, G.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Polymer. J. 1985. 17. 117. 38. Newkome, G. R.; Yao, Z.; Baker, G. R.; Gupta, V. K. J. Org. Chem. 1985, 50, 2003. 39. Newkome, G. R.; Yao, Z.; Baker, G. R.; Gupta, V. K.; Russo, P. S.; Saunders, M. J. J. Am. Chem. Soc. 1986, 108, 849. 40. Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1990, 112, 7638. 41. Spindler, R.; Fréchet, J. M. J. Chem. Soc., Perkin Trans. 1 1993,913. 42. Spindler, R.; Fréchet, J. M. J. Macromolecules 1993, 26, 4809. 43. Peerlings, H. W. I.; Van Benthem, R. A. T. M.; Meijer, E. W. J. Poly, Sci,. Part A:Polym. Chem. 2001, 39,3112. 44. Chiu, H. C.; Lin, Y. W.; Huang, Y. F.; Chuang, C. K.; Chern, C. S. Angew. Chem. Int. Ed. 2008, 47, 1875. 45. Cho, H. K.; Co, J. H.; Cheong, I. W. Macromolecular Symposium 2007, 249, 96. 46. Lee, E. S.; Kwon, M. J.; Nab, K.; Bae, J. H. Colloids and Surfaces B: Biointrfaces 2007, 249, 96. 47. Pitois, O.; François, B. Colloid Polym Sci 1999, 277, 574. 48. Stenzel, M. H.; Davis, T. P.; Fane, A. G.; Chen, V. Angew. Chem. Int. Ed. 2001, 40, 3428. 49. Yabu, H.; Takebayshi,M.; Tanaka, M.; Shimomura, M. Langmuir 2005, 21, 3235. 50. Cheng, C.; Tian, Y.; Shi, Y.; Tang, R.; Xi, F. Macromol. Rapid Commun. 2005, 26, 1266. 51. Deepak, V. D.; Asha, S. K. J. Phys. Chem. 2006, 110, 21450. 52. Ting, W. H.; Chen, C. C.; Dai, S. A.; Suen, S. Y.; Yang, I. K.; Liu, Y. L.; Chen, F. M. C.; Jeng, R. J. J. Mater. Chem. 2009, 19, 4819. 53. Wong, K. H.; Stenzel, M. H.; Duvall, S.; Ladouceur, F. Chem. Mater. 2010, 22, 1878. 54. Rannard, S. P.; Davis, N. J. J. Am. Chem. Soc. 2000, 122, 11729. 55. 陳衍甫; 國立中興大學化工系碩士論文,2001.
摘要: 高分子的自組裝行為 (self-assembly) 一直以來都是高分子物理中受人矚目的一個現象,此行為的產生是因結構的親疏水性或是溶劑條件的不同所致,當中有靜電作用、氫鍵、凡德瓦爾力和疏水效應的影響。一般而言,自組裝行為是由於block copolymer中,同時具有兩種不同性質的鏈段所造成,其中也有導入規則樹枝狀高分子 (dendrimer) 之結構。 本實驗利用具有反應選擇性之構築單元4-isocyanato-4’ (3,3-dimethyl- 2,4-dioxo-azetidino)diphenylmethane (IDD) 以收斂方式來進行逐步式的合成反應,利用stearyl alcohol分別合成出末端為十八個碳鏈不同代數之urea/malonamide規則樹枝狀高分子 ([G-0.5]-C18、[G-1]-C18、[G-1.5]-C18) ;並且利用N-(3-amino-propyl)diethanolamine (APDEA) 和[G-1.5]-C18上之azetidine-2,4-dione進行開環反應,合成出具有diol官能基規則樹枝狀高分子 ([G-1.5]-C18-diol);爾後導入聚胺酯 (polyurethane) 系統中,製備出側鏈型規則樹枝狀高分子並成功地改善機械性質。由於接枝後之高分子於側鏈分子結構上具有多重氫鍵官能基,加上末端長烷鏈所形成的bulky rod,使得側鏈型規則樹枝狀高分子能夠輕易經由breath-figure的方式得到蜂窩狀高分子膜。 此外,為了達到更進一步疏水的目的,我們將末端的C18系列,改成表面能小的全氟烷基F17,利用IDD和1H,1H,2H,2H-perfluoro-1-decanol反應合成不同代數的規則樹枝狀高分子 ([G-0.5]-F17、[G-1]-F17、[G-1.5]-F17) ;同樣地,利用APDEA將[G-1.5]-F17進行開環反應,形成[G-1.5]-F17-diol做為PU中的鏈延長劑,並且以相同的程序製備出蜂窩狀薄膜,和C18系列的進行比較,探討其疏水的性質。
In this work, the bifunctional compound 4-isocyanato-4' (3,3-dimethyl-2,4- dioxo- azetidino) diphenylmethane (IDD) was used as building block for the synthesis of polyurea/malonaimde dendrons via a convergent route. . Stearyl alcohol was selected as terminal group Different generations of dendrons with peripheral stearyl groups ([G-0.5]-C18, [G-1]-C18, [G-1.5]-C18) were synthesized . To introduce the dendrons into the polyurethane systems, N-(3-aimnopropyl)-diethanolamine (APDEA) was reacted with azetidine-2,4-dione containing dendrons. The dendron with diol groups were easily introduced into the polyurethanes for the synthesis of dendritic side chain polymers with good mechanical properties. The dendrons comprised urea/malonamide linkages and alkyl chains, thereby enhancing the degrees of hydrogen bonding (at the focal segment) and van der Waals interaction (at the periphery), respectively. The latter interactions helped induce self-assembly and phase separation during the preparation of the polymer films. Using a simple and rapid breath-figure method, self-assembled honeycomb-like films were readily obtained from the dendritic side chain polyurethanes.Furthermore, 1H, 1H, 2H, 2H-perfluoro-1-decanol with low surface energy feature was selected for further increasing the hydrophobic properties in this study. Different generations of fluoro-containing dendrons ([G-0.5]-F17, [G-1]-F17, [G-1.5]-F17) were synthesized accordingly. Using the same methodology, [G-1.5]-F17-diol was obtained as the chain extender for the synthesis of polyurethanes. Finally, the hydrophilic properties of C18 and F17 series dendritic side chain PUs were studied in this work.
URI: http://hdl.handle.net/11455/3807
其他識別: U0005-1208201016252700
文章連結: http://www.airitilibrary.com/Publication/alDetailedMesh1?DocID=U0005-1208201016252700
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