Please use this identifier to cite or link to this item: http://hdl.handle.net/11455/91554
標題: 合成電子用熱固型樹脂之研究與性質探討
Synthesis and Characterization of Thermosetting Resins used in Electronic Applications
作者: Yu-Chun Chou
周有駿
關鍵字: Benzoxazine
Blend
Renewable resources
Poly(aryl ether sulfone)
氧代氮代苯并環己烷
混摻
可再生資源
聚芳醚碸
環氧樹脂
引用: (1). Ning, X.; Ishida, H. Journal of Polymer Science Part A: Polymer Chemistry 1994, 32, (6), 1121-1129. (2). Wang, C. F.; Su, Y. C.; Kuo, S. W.; Huang, C. F.; Sheen, Y. C.; Chang, F. C. Angewandte Chemie International Edition 2006, 45, (14), 2248-2251. (3). Holly, F. W.; Cope, A. C. Journal of the American Chemical Society 1944, 66, (11), 1875-1879. (4). Burke, W. Journal of the American Chemical Society 1949, 71, (2), 609-612. (5). Russell, V. M.; Koenig, J. L.; Low, H. Y.; Ishida, H. Journal of applied polymer science 1998, 70, (7), 1413-1425. (6). Brunovska, Z.; Liu, J. P.; Ishida, H. Macromolecular Chemistry and Physics 1999, 200, (7), 1745-1752. (7). Lin, C. H.; Chang, S. L.; Hsieh, C. W.; Lee, H. H. Polymer 2008, 49, (5), 1220-1229. (8). Kumar, K. S.; Nair, C. R.; Ninan, K. European Polymer Journal 2009, 45, (2), 494-502. (9). Kimura, H.; Ohtsuka, K.; Matsumoto, A. Express Polymer Letters 2011, 5, (12), 1113-1122. (10). Li, X.; Gu, Y. Polymer Chemistry 2011, 2, (12), 2778-2781. (11). Lin, C. H.; Huang, S. J.; Wang, P. J.; Lin, H. T.; Dai, S. A. Macromolecules 2012, 45, (18), 7461-7466. (12). Li, X.; Luo, X.; Liu, M.; Ran, Q.; Gu, Y. Materials Chemistry and Physics 2014, 148, (1), 328-334. (13). Wang, M. W.; Jeng, R. J.; Lin, C. H. Macromolecules 2015, 48, (8), 2417-2421. (14). Tsuchiya, K.; Endo, T. Journal of Polymer Science Part A: Polymer Chemistry 2014, 52, (5), 699-706. (15). Gibson, H. W.; Dotson, D. L.; Marand, H.; Swager, T. M. Molecular Crystals and Liquid Crystals 1999, 326, (1), 113-138. (16). Andreu, R.; Ronda, J. Synthetic Communications® 2008, 38, (14), 2316-2329. (17). Andreu, R.; Reina, J.; Ronda, J. Journal of Polymer Science Part A: Polymer Chemistry 2008, 46, (10), 3353-3366. (18). Olah, G. A.; Narang, S. C.; Gupta, B. B.; Malhotra, R. The Journal of Organic Chemistry 1979, 44, (8), 1247-1251. (19). Olah, G. A.; Husain, A.; Singh, B. P.; Mehrotra, A. K. The Journal of Organic Chemistry 1983, 48, (21), 3667-3672. (20). Wang, D.; Li, B.; Zhang, Y.; Lu, Z. Journal of Applied Polymer Science 2013, 127, (1), 516-522. (21). Agag, T.; Arza, C. R.; Maurer, F. H.; Ishida, H. Journal of Polymer Science Part A: Polymer Chemistry 2011, 49, (20), 4335-4342. (22). Koz, B.; Kiskan, B.; Yagci, Y. Polymer Bulletin 2011, 66, (2), 165-174. (23). Kiskan, B.; Yagci, Y. Polymer 2008, 49, (10), 2455-2460. (24). Kiskan, B.; Yagci, Y.; Ishida, H. Journal of Polymer Science Part A: Polymer Chemistry 2008, 46, (2), 414-420. (25). Lin, C. H.; Chang, S. L.; Shen, T. Y.; Shih, Y. S.; Lin, H. T.; Wang, C. F. Polymer Chemistry 2012, 3, (4), 935-945. (26). Imran, M.; Kiskan, B.; Yagci, Y. Tetrahedron Letters 2013, 54, (36), 4966-4969. (27). Fang, T.; Shimp, D. A. Progress in polymer Science 1995, 20, (1), 61-118. (28). Shieh, J. Y.; Yang, S. P.; Wu, M. F.; Wang, C. S. Journal of Polymer Science Part A: Polymer Chemistry 2004, 42, (11), 2589-2600. (29). Banks, M.; Ebdon, J. R.; Johnson, M. Polymer 1993, 34, (21), 4547-4556. (30). Lin, C. H.; Chang, S. L.; Wei, T. P. Macromolecular Chemistry and Physics 2011, 212, (5), 455-464. (31). Alunga, K. R.; Ye, Y.-Y.; Li, S.-R.; Wang, D.; Liu, Y. Catalysis Science & Technology 2015. (32). Chatel, G.; Rogers, R. D. ACS Sustainable Chemistry & Engineering 2013, 2, (3), 322-339. (33). Alonso, D. M.; Wettstein, S. G.; Dumesic, J. A. Chemical Society Reviews 2012, 41, (24), 8075-8098. (34). Zakzeski, J.; Bruijnincx, P. C.; Jongerius, A. L.; Weckhuysen, B. M. Chemical reviews 2010, 110, (6), 3552-3599. (35). Gosselink, R.; De Jong, E.; Guran, B.; Abächerli, A. Industrial Crops and Products 2004, 20, (2), 121-129. (36). Chakar, F. S.; Ragauskas, A. J. Industrial Crops and Products 2004, 20, (2), 131-141. (37). Wang, S.; Lin, Y.; Chu, F. In Molecular cloning of caffeoyl-CoA-3-O-methyltransferase gene from Chamaecyparis formosensis and lignin analyzing in its transgenic tobacco, Quarterly Journal of Chinese Forestry 2008, 43, (3), 323-338. (38). Zhu, H.; Chen, Y.; Qin, T.; Wang, L.; Tang, Y.; Sun, Y.; Wan, P. RSC Advances 2014, 4, (12), 6232-6238. (39). Fache, M.; Darroman, E.; Besse, V.; Auvergne, R.; Caillol, S.; Boutevin, B. Green Chemistry 2014, 16, (4), 1987-1998. (40). da Silva, E. B.; Zabkova, M.; Araújo, J.; Cateto, C.; Barreiro, M.; Belgacem, M.; Rodrigues, A. Chemical Engineering Research and Design 2009, 87, (9), 1276-1292. (41). Ramachandra Rao, S.; Ravishankar, G. A. Journal of the Science of Food and Agriculture 2000, 80, (3), 289-304. (42). Wong, Z.; Chen, K.; Li, J. Bioresources 2010, 5, (3), 1509-1516. (43). Pinto, P. C. R.; Costa, C. E.; Rodrigues, A. E. Industrial & Engineering Chemistry Research 2013, 52, (12), 4421-4428. (44). Benitez, F. J.; Real, F. J.; Acero, J. L.; Leal, A. I.; Cotilla, S. Journal of Environmental Science and Health, Part A 2005, 40, (12), 2153-2169. (45). Harrison, B. M.; Priest, F. G. Journal of agricultural and food chemistry 2009, 57, (6), 2385-2391. (46). Gonter, K.; Takács, E.; Wojnárovits, L. Radiation Physics and Chemistry 2012, 81, (9), 1495-1498. (47). Attwood, T.; Newton, A.; Rose, J. British Polymer Journal 1972, 4, (5), 391-399. (48). Johnson, R. N.; Farnham, A. G.; Clendinning, R. A.; Hale, W. F.; Merriam, C. N. Journal of Polymer Science Part A‐1: Polymer Chemistry 1967, 5, (9), 2375-2398. (49). Viswanathan, R.; Johnson, B.; McGrath, J. Polymer 1984, 25, (12), 1827-1836. (50). Hedrick, J.; Mohanty, D.; Johnson, B.; Viswanathan, R.; Hinkley, J.; McGrath, J. Journal of Polymer Science Part A: Polymer Chemistry 1986, 24, (2), 287-300. (51). Hedrick, J.; Dumais, J.; Jelinski, L.; Patsiga, R.; McGrath, J. Journal of Polymer Science Part A: Polymer Chemistry 1987, 25, (8), 2289-2300. (52). Harrison, W. L. Synthesis and Characterization of Sulfonated Poly(Arylene Ether Sulfone) Copolymers via Direct Copolymerization: Candidates for Proton Exchange Membrane Fuel Cells 2002, Virginia Polytechnic Institute and State University. (53). Argyropoulos, D. S.; Sadeghifar, H.; Cui, C.; Sen, S. ACS Sustainable Chemistry & Engineering 2013, 2, (2), 264-271. (54). Yee, A. F.; Pearson, R. A. Journal of materials science 1986, 21, (7), 2462-2474. (55). Aguilar‐Vega, M.; Paul, D. Journal of Polymer Science Part B: Polymer Physics 1993, 31, (11), 1599-1610. (56). Hoffmann, T.; Pospiech, D.; Häußler, L.; Komber, H.; Voigt, D.; Harnisch, C.; Kollann, C.; Ciesielski, M.; Döring, M.; Perez‐Graterol, R. Macromolecular Chemistry and Physics 2005, 206, (4), 423-431. (57). Lin, C. H.; Chen, J. C.; Huang, C. M.; Jehng, J. M.; Chang, H. C.; Juang, T. Y.; Su, W. C. Polymer 2013, 54, (26), 6936-6941. (58). Lin, C. H.; Chen, J. C.; Huang, C. M.; Juang, T. Y. Journal of Applied Polymer Science 2014, 131, (21). (59). Einsla, B. R.; McGrath, J. E. American Chemical Society Division Fuel Chemistry 2004, 49, 616. (60). Kwon, Y.; Lee, S. Y.; Hong, S.; Jang, J. H.; Henkensmeier, D.; Yoo, S. J.; Kim, H.-J.; Kim, S.-H. Polymer Chemistry 2015, 6, (2), 233-239. (61). Hay, J. N.; Porter, D.; Raval, H. M. Journal of Materials Chemistry 2000, 10, (8), 1811-1818. (62). Johnson, R. N.; Farnham, A. G. Journal of Polymer Science Part A‐1: Polymer Chemistry 1967, 5, (9), 2415-2427. (63). Kim, D. S.; Robertson, G. P.; Guiver, M. D. Macromolecules 2008, 41, (6), 2126-2134. (64). Liu, Y. L.; Hsiue, G. H.; Lee, R. H.; Chiu, Y. S. Journal of applied polymer science 1997, 63, (7), 895-901. (65). Wang, C.-S.; Shieh, J.-Y. Polymer 1998, 39, (23), 5819-5826. (66). Cai, S. X.; Lin, C. H. Journal of Polymer Science Part A: Polymer Chemistry 2005, 43, (13), 2862-2873. (67). Lin, C. H.; Cai, S. X.; Lin, C. H. Journal of Polymer Science Part A: Polymer Chemistry 2005, 43, (23), 5971-5986.
摘要: 本篇論文主要分為兩個部分,第一部分為利用親核性取代法合成一具新穎性,包含1,3,5-triazine 結構之氧代氮代苯并環己烷(Benzoxazine),並利用傅立葉轉換紅外光譜儀(FT-IR) 在不同溫度下針對其單體的開環機制,進行追蹤偵測,其結果顯示該單體開環機制與Benzoxazine/Cyanate ester 混摻系統相似,皆會形成 alkyl isocynarute與diphenyl ether linkage結構,並且高溫固化後的Polybenzoxazine經過性質測試,顯示有高的熱穩定性(空氣下Td5% = 427 oC),高的玻璃轉移溫度(279 oC),低的介電常數(Dk = 2.4)等優異的性質,適合發展作為航空、航太、微電子設備等之高溫耐燃性材料。 第二部分為利用可再生資源為雙酚單體(Acetovanillone)為合成之基材,合成出含有巨大基團之磷系聚芳醚碸,並將懸掛在主鏈段上之甲氧官能基去甲基化,成功得到一具有反應性之熱塑型高分子,另與市售三種環氧樹脂(DGEBA、HP7200、CNE)進行硬化增韌改質,得到的環氧樹脂固化物,不僅擁有高的耐熱性質,並保有聚芳醚碸之高穿透度和透明性,對於電子產品封裝製程的改進上提供一優秀的材料與方法以供選擇。
This research is divided into two parts. In the first part, cyanurate-containing benzoxazine (Triazine-BZ) was synthesized by nucleophilic substitution of cyanuric chloride with 4-aminophenol/phenol-based benzoxazine (OH-BZ). The reaction mechanism between benzoxazine and cyanurate moieties was monitored by FTIR. Also, the alkyl isocyanurate and diphenyl ether structures were formed at a high temperature. It suggests that the rearrangement of cyanurate with benzoxazine moiety was carried out. Moreover, the thermosets exhibit excellent thermal properties, thermal stabilities and dielectric properties. The bio-based phosphinated bisphenol (1) was synthesized by using acetovanillione as the starting material. A novel phosphinated poly(ether sulfone), DPES-OCH3, with methoxy group was prepared for the work. The poly(ether sulfone), DPES-OH, with a phenol pendent group in the repeating unit was synthesized from demethylation of DPES-OCH3 provides phenol linkages as reacting sites for epoxy resins. Subsequently, the curing procedure of DPES-OH with three epoxy resins was performed. Flexible and transparent films of thermosets can be obtained and exhibits great thermal properties.
URI: http://hdl.handle.net/11455/91554
其他識別: U0005-2807201513463800
文章公開時間: 2018-07-30
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