Browse > Article
http://dx.doi.org/10.5012/bkcs.2011.32.8.2737

Ring-Opening Metathesis Polymerization and Hydrogenation of Ethyl-substituted Tetracyclododecene  

Kwon, Oh-Joon (Energy Division, Korea Institute of Science and Technology)
Vo, Huyen Thanh (Energy Division, Korea Institute of Science and Technology)
Lee, Sul-Bee (Energy Division, Korea Institute of Science and Technology)
Kim, Tae-Kyung (Energy Division, Korea Institute of Science and Technology)
Kim, Hoon-Sik (Department of Chemistry, Kyung Hee University)
Lee, Hyun-Joo (Energy Division, Korea Institute of Science and Technology)
Publication Information
Abstract
Ring-opening metathesis polymerization (ROMP) of an ethyl-substituted tetracyclododecene (8-ethyltetracyclo[$4.4.0.1^{2,5}.1^{7,10}$] dodec-3-ene, Et-TCD) was carried out in the presence of a ternary catalyst system consisting of $WCl_6$, triisobutyl aluminium (iso$Bu_3Al$), and ethanol. The optimal molar ratio of Et-TCD/$WCl_3$/iso-$Bu_3Al$/ethanol was found as 500/1/3/2 at which the yield of ring-opened polymer was 100%. 1-Hexene was shown to be an effective molecular weight controlling agent for ROMP reaction of Et-TCD. The hydrogenation of the ring opened polymer (p-Et-TCD) was conducted successfully using Pd(5 wt %)/${\gamma}$-$Al_2O_3$ at $80^{\circ}C$ for 1 h. Chemical structures of p-Et-TCD and its hydrogenated product($H_2$-p-Et-TCD) were characterized using 2D NMR techniques ($^1H-^1H$ COSY and $^1H-^{13}C$ HSQC). The changes of physical properties such as thermal stability, glass transition temperature and light transmittance after the hydrogenation were also investigated using TGA, DSC, and UV.
Keywords
Ring-opening metathesis polymerization (ROMP); Hydrogenation; 2D NMR technique; Tetracyclododecene;
Citations & Related Records

Times Cited By Web Of Science : 2  (Related Records In Web of Science)
Times Cited By SCOPUS : 2
연도 인용수 순위
  • Reference
1 Carvill, A. G.; Greene, R. M. E.; Hamilton, J.; Ivin, K. J.; Kenwrigth, A. M.; Rooney, J. J. Macromol. Chem. Phys. 1998, 199, 687.
2 Kim, J.; Wu, C. J.; Kim, W.-J.; Kim, J.; Lee, H.; Kim, J.-D. J. Appl. Polym. Sci. 2010, 116, 479.   DOI   ScienceOn
3 Choo, H. P.; Liew, K. Y.; Liu, H.; Seng, C. E.; Mahmood, W. A. K.; Bettahar, M. J. Mol. Catal. A-Chem. 2003, 191, 113.   DOI   ScienceOn
4 Wang, D.-S.; Wang, D.-W.; Zhou, Y.-G. Synlett. 2011, 7, 47.
5 Otsuki, T.; Goto, K.; Komiya, Z. J. Polym. Sci., Polym. Chem. 2000, 38, 4661.   DOI   ScienceOn
6 Tadahiro, S.; Masutada, O.; Tadashi, A. Japanese Patent 193323, 1999.
7 Hashizume, M.; Uchida, T.; Aida, F.; Suzuki, T.; Inomata, Y.; Matsumura, Y. US Patent 6512152, 2003.
8 Bielawski, C.; Grubbs, R. Prog. Polym. Sci. 2007, 32, 1.   DOI   ScienceOn
9 Hayano, S.; Sugawara, T; Tsunogae, Y. Appl. Polym. Sci. 2006, 44, 3153.   DOI   ScienceOn
10 Dragutan, V.; Dragutan, I.; Fischer, H. J. Inorg. Organomet. Polym. 2008, 18, 18.   DOI
11 Camm, K. D.; Castro, N. M.; Liu, Y.; Czechura, P.; Snelgrove, J. L.; Fogg, D. E. J. Am. Chem. Soc. 2007, 129, 4168.   DOI   ScienceOn
12 Ogata, Y.; Makita, Y.; Okaniwa, M. Polymer 2008, 49, 4819.   DOI   ScienceOn
13 Yoshinori, M. Japanese Patent 252964, 2003.
14 Hayano, S.; Takeyama, Y.; Tsunogae, Y.; Igarashi, I. Macromolecules 2006, 39, 4663.   DOI   ScienceOn
15 Gehlsen, M. D.; Bates, F. S. Macromolecules 1993, 26, 4122.   DOI   ScienceOn
16 Hosaka, T.; Mizuno, H.; Koushima, Y.; Kohara, T.; Nasuume, T. US Patent 5462995, 1995.
17 Sohn, B. H.; Gratt, J. A.; Lee, J. K.; Cohen, R. E. J. Appl. Polym. Sci. 1995, 58, 1041.   DOI   ScienceOn
18 Lee, L. B. W.; Register, R. A. Macromolecules 2005, 38, 1216.   DOI   ScienceOn
19 Hatjopoulos, J. D.; Register, R. A. Macromoleculs 2005, 38, 10320.   DOI   ScienceOn
20 Al-Samak, B.; Amir-Ebrahimi, V.; Carvill, A. G.; Hamilton, J. G.; Rooney, J. J. Polym. Int. 1996, 41, 85.   DOI   ScienceOn
21 Hayano, S.; Kurakata, H.; Uchida, D.; Sakamoto, M.; Kishi, N.; Matsumoto, H.; Tsungoae, Y.; Igarashi, I. Chemistry Letters 2003, 32, 670.   DOI   ScienceOn
22 Yamazaki, M. J. Mol. Catal. A-Chem. 2001, 213, 81.
23 Shin, J. Y.; Park, J. Y.; Liu, C.; He, J.; Kim, S. C. Pure Appl. Chem. 2005, 77, 801.   DOI   ScienceOn