Please use this identifier to cite or link to this item: http://hdl.handle.net/11455/3618
標題: 藉由新穎方法合成磷系及氟系之benzoxazines之樹脂研究與其性質研究
Synthesis and characterization of phosphorous polybenzoxazines and fluorinated polybenzoxaines by Novel Approach
作者: 李豪修
Lee, Hao-Hsin
關鍵字: phosphous
含氟
fluorinated
benzoxazine
polybenzoxazine
含磷
氧代氮代苯并環己烷
出版社: 化學工程學系所
引用: 1. H. Ishida, Allen, J. D. J. Polym. Sci. Part B: Polym.Phys.,1996,34,1019 2. X. Ning, and H. Ishida,J.Polym.Sci.Part A :Polym.Chem.,1994,32,1121 3. H. Ishida, and Y. Rodriguez, Polymer,1995,36,3151 4. Z. Brunovska, J. P. Liu, and H. Ishida, Macromol. Chem. Phys.,1999,200,1745 5. Y. X. Wang, H. Ishida, Macromolecules,2000,33,2839 6. Z. Brunovska, R. Lyon, H. Ishida Thermochim Acta, 2000,357,195 7. Z. Brunovska, H. Ishida, J. Polym. Sci.,1999,73, 2937 8. H. Kimura,Y. Murata, A. Matsumoto, K. Hasegawa, K. Ohtsuka, A. Fukuda, J. Polym. Sci.,1999,74, 2266 9. Y.-C. Su, F.-C. Chang,Polymer,2003,7990,44,7989-7996 10. Y. L. Liu, J. M. Yu, C. I. Chou, J. Polym. Sci. Part A : Polym. Chem.,2004,42, 5954-5963 11. D. J. Allen,Hatsuo Ishida, Journal of Applied Polymer Science, 2006,Vol. 101, 2798-2809 12. Y. L. Liu, J. M. Yu, J. Polym. Sci. Part A : Polym. Chem., 2006,44, 1890 13. C. H. Lin, S. X. Cai, T. S. Leu, T. Y. Hwang, H. H. Lee, J. Polym. Sci. Part A : Polym. Chem.,2006,44, 3454 14. H. Ishida, and Y. Rodriguez, Polymer,1995,36, 3151 15. H. Y. Low, H. Ishida, J Polym Sci Part B: Polym Phys,1998,36, 1935 16. D. J. Allen, H. Ishida, Journal of Applied Polymer Science, 2006,Vol. 101, 2798-2809
摘要: 本實驗Part I 是由三個含氟之雙胺(2,2-Bis[4-(4-amino-2-trifluoromethylphenoxy)phenyl]propane(2)/2,2-Bis[4-(4-amino-2-trifluoromethylphenoxy)phenyl]hexafluoropropane(3)/4,4''(Hexafluoroisopropylidene)diphenol(4))與2-hydroxybenzaldehyde合成一系列含Schiff base linkage之化合物(6/7/8),再利用NaBH4將-C=N-還原成-CH2-NH-,反應合成一系列同時擁有酚基以及二級胺之單體(10/11/12/13),使用上述單體與甲醛反應合成一系列新穎含氟之benzoxazine(14/15/16)藉由FTIR、NMR鑑定其結構正確。 因為將氟取代基導入高分子中可降低介電性質,一系列具有三氟甲基之benzoxazine,經由熱硬化過後具有低介電之特性,也具有良好的玻璃轉移溫度及熱裂解溫度,與Fa不同比例混合,亦合降低高分子之介電常數,提昇熱性質。 本實驗Part II是由四個商品化之脂肪族雙胺(Ethylene diamine(1)/1,4 Diamino buteane(2)/1,6 Hexadiamine(3)/1,8 Diamino octane(4))利用2-hydroxybenzaldehyde合成一系列含Schiff base linkage之化合物(5/6/7/8) ,再經由親核加成將DOPO與含Schiff base linkage之化合物反應合成一系列同時擁有P和C雙對掌中心之diastereomers單體(9/10/11/12)。利用上述這些同時擁有酚基以及二級胺之diastereomers單體與甲醛反應合成一系列新穎含磷之benzoxazine (13/14/15/16)。藉由FTIR、NMR鑑定其結構正確。 由於立體障礙的關係,p(P-C2-Bz)、p(P-C4-Bz)、p(P-C6-Bz)、p與(P-C8-Bz)之玻璃轉移溫度及熱裂解溫度不如預期的高。然而,p(P-C2-Bz)、p(P-C4-Bz)、p(P-C6-Bz)、p與(P-C8-Bz)的合成顯示出一個新的benzoxazine合成路徑,將在未來持續探討。
Part I : Synthesis a series of new fluorinated monomers use (2,2-Bis[4-(4-amino-2-trifluoromethylphenoxy)phenyl]propane(2)/2,2-Bis[4-(4-amino-2-trifluoromethylphenoxy)phenyl]hexafluoropropane(3)/4,4''(Hexafluoroisopropylidene)diphenol(4)) and 2-hydroxybenzaldehyde were successfully synthesized from the nucleiphilic addition of the Schiff-base compounds(6/7/8),and then we use NaBH4 reduced C=N double bond became CH2-NH,synthesis a series of monomer contain phenol group and secondary amine group (10/11/12),synthesis a series of fluorinated benzoxazine(14/15/16) using that monomer reaction with formaldehyde. And their structures were confirmed by FTIR, NMR, DSC. Part II : A series of linear aliphatic diamine (Ethylene diamine(1)/1,4 Diamino buteane(2)/1,6 Hexadiamine(3)/1,8 Diamino octane(4)) and 2-hydroxybenzaldehyde were successfully synthesized from the nucleiphilic addition of the Schiff-base compounds(5/6/7/8),and then we used DOPO nucleiphilic addition of the Schiff-base compounds become a series of diastereomers monomer contain phenol group and secondary amine group (9/10/11/12)。Synthesis a series of phosphorous benzoxazine(13/14/15/16) using that monomer reaction with formaldehyde. And their structures were confirmed by FTIR, NMR, DSC. Properties, such as glass transition temperature, thermal degradation temperature, and char yield, of the polybenzoxazines are investigated as a function of the chain length.
URI: http://hdl.handle.net/11455/3618
其他識別: U0005-0808200717490000
文章連結: http://www.airitilibrary.com/Publication/alDetailedMesh1?DocID=U0005-0808200717490000
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