Simplified TERP to achieve living free radical polymerization with crude ethyl 2-phenyltellanyl-2-methylpropionate as mediator
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- 作者：Haochuan Chen (1)
Jiao Jiao (1)
Changwen Zhao (1)
Yuhong Ma (1) (2)
Wenchao Ma (1)
Wantai Yang (1) (2) - 关键词：Living free radical polymerization ; Chain transfer agent ; Organotellurium compound ; Styrene ; Butyl acrylate ; Block copolymer
- 刊名：Polymer Bulletin
- 出版年：2014
- 出版时间：July 2014
- 年：2014
- 卷：71
- 期：7
- 页码：1797-1811
- 全文大小：
- 参考文献：1. Haloi Dhruba J, Ata Souvik, Singha Nikhil K (2012) Synthesis and characterization of all acrylic block copolymer/clay nanocomposites prepared via surface initiated atom transfer radical polymerization (SI-ATRP). Ind Eng Chem Res 51(29):9760-768 CrossRef
2. Hawker CJ, Bosman AW, Harth E (2001) New polymer synthesis by nitroxide mediated living radical polymerizations. Chem Rev 101:3661-688 CrossRef
3. Matyjaszewski K, Xia JH (2001) Atom transfer radical polymerization. Chem Rev 101:2921-990 CrossRef
4. Kamigaito M, Ando T, Sawamoto M (2001) Metal-catalyzed living radical polymerization. Chem Rev 101:3689-745 CrossRef
5. Matyjaszewski K (2003) Advances in controlled/living radical polymerization (ACS Symp. Ser. 854). American Chemical Society, Washington, DC
6. Otsu T, Tazaki T (1986) Living radical polymerization in homogeneous system with phenylazotriphenylmethane as a thermal iniferter. Polym Bull 16:277-84 CrossRef
7. Otsu T, Matsunaga T, Kuriyama A (1989) Living radical polymerization through the use of iniferters: controlled synthesis of polymers. Eur Polym 25(7&8):643-50 CrossRef
8. Chong YK, Ercole F, Moad G, Rizzardo E, Thang SH, Anderson AG (1999) Imidazolidinone nitroxide-mediated polymerization. Macromolecules 32(21):6895-903 CrossRef
9. Georges MK, Veregin RPN, Kazmaier PM, Hamer GK (1993) Narrow molecular weight resins by a free-radical polymerization process. Macromolecules 26(11):2987-988 CrossRef
10. Wang JS, Matyjaszewski K (1995) Controlled/“living-radical polymerization. Atom transfer radical polymerization in the presence of transition-metal complexes. J Am Chem Soc 117(20):5614-615 CrossRef
11. Wang JS, Matyjaszewski K (1995) “Living-controlled radical polymerization. Transition-metal-catalyzed atom transfer radical polymerization in the presence of a conventional radical initiator. Macromolecules 28(22):7572-573 CrossRef
12. Kato M, Kamogato M, Sawamoto M, Higashimura T (1995) Polymerization of methyl methacrylate with the carbon tetrachloride/dichlorotris-(triphenylphosphine)ruthenium(II)/methylaluminum bis(2,6-di-tert-butylphenoxide) initiating system: possibility of living polymerization. Macromolecules 28:1721-723 CrossRef
13. Matyjaszewski K (2012) Atom transfer radical polymerization (ATRP): current status and future perspectives. Macromolecules 45:4015-039 CrossRef
14. Chiefari J, Chong YK, Ercole F, Krstina J, Jeffery J, Le TPT, Mayadunne RTA, Meijs GF, Moad CL, Moad G, Rizzardo E, Thang SH (1998) Living free-radical polymerization by reversible addition–fragmentation chain transfer: the RAFT process. Macromolecules 31:5559-562 CrossRef
15. Kayahara E, Yamago S (2009) Development of an arylthiobismuthine cocatalyst in organobismuthine-mediated living radical polymerization: applications for synthesis of ultrahigh molecular weight polystyrenes and polyacrylates. J Am Chem Soc 131(7):2508-513 CrossRef
16. Yamago S (2006) Development of organotellurium-mediated and organostibine-mediated living radical polymerization. J Polym Sci Part A Polym Chem 44:1-2 CrossRef
17. Yamago S (2009) Precision polymer synthesis by degenerative transfer controlled/living radical polymerization using organotellurium, organostibine, and organobismuthine chain-transfer agents. Chem Rev 109:5051-068 CrossRef
18. Yusa S, Yamago S, Suguhara M, Morikawa S, Yamamoto T, Morishima Y (2007) Thermo-responsive diblock copolymers of poly( / N-isopropylacrylamide) and poly( / N-vinyl-2-pyrroridone) synthesized via organotellurium-mediated controlled radical polymerization (TERP). Macromolecules 40:5907-915 CrossRef
19. Moribe H, Kitayama Y, Suzuki T, Okubo M (2010) Emulsifier-free, organotellurium-mediated living radical emulsion polymerization of styrene: effect of stirring rate. Macromolecules 44(2):263-68 CrossRef
20. Kwak Y, Goto A, Fukuda T, Kobayashi Y, Yamago S (2006) A systematic study on activation processes in organotellurium-mediated living radical polymerizations of styrene, methyl methacrylate, methyl acrylate, and vinyl acetate. Macromolecules 39:4671-679 CrossRef
21. Feng S, Xu W, Nakanishi K, Yamago S (2011) Highly controlled organotellurium-mediated living radical polymerization (TERP) in ionic liquids (ILs). The new role of ILs in radical reactions. ACS Macro Lett 1(1):146-49 CrossRef
22. Goto A, Kwak Y, Fukuda T, Yamago S, Iida K, Nakajima M, Yoshida J (2003) Mechanism-based invention of high-speed living radical polymerization using organotellurium compounds and azo-initiators. J Am Chem Soc 125:8720-721 CrossRef
23. Kayahara E, Yamago S, Kwak Y, Goto A, Fukuda T (2008) Optimization of organotellurium transfer agents for highly controlled living radical polymerization. Macromolecules 41(3):527-29 CrossRef
24. Yamago S, Iida K, Yoshida J (2002) Tailored synthesis of structurally defined polymers by organotellurium-mediated living radical polymerization (TERP): synthesis of poly(meth)acrylate derivatives and their di- and triblock copolymers. J Am Chem Soc 124:13666-3667 CrossRef
25. Yamago S, Ukai Y, Matsumoto A, Nakamura Y (2009) Organotellurium-mediated controlled/living radical polymerization initiated by direct C–Te bond photolysis. J Am Chem Soc 131(6):2100-101 CrossRef
26. Nakamura Y, Kitada Y, Kobayashi Y, Ray B, Yamago S (2011) Quantitative analysis of the effect of azo initiators on the structure of α-polymer chain ends in degenerative chain-transfer-mediated living radical polymerization reactions. Macromolecules 44:8388-397 CrossRef
27. Yamago S, Iida K, Yoshida J (2002) Organotellurium compounds as novel initiators for controlled/living radical polymerizations. Synthesis of functionalized polystyrenes and end-group modifications. J Am Chem Soc 124:2874-875 CrossRef - 作者单位：Haochuan Chen (1)
Jiao Jiao (1)
Changwen Zhao (1)
Yuhong Ma (1) (2)
Wenchao Ma (1)
Wantai Yang (1) (2)
1. Key Laboratory of Carbon Fiber and Functional Polymers, Ministry of Education, Beijing University of Chemical Technology, Beijing, 100029, China
2. Beijing Engineering Research Center of Syntheses and Applications of Waterborne Polymers, Beijing University of Chemical Technology, Beijing, 100029, China - ISSN：1436-2449
文摘
Organotellurium compounds-mediated living radical polymerization (TERP) is one of the most robust tools of living free radical polymerizations (LRP). However, synthesis and purification of organotellurium compounds are time-consuming and to be operated in an inert atmosphere due to their extreme sensitivity to trace oxygen. In this article, a simple process of TERP, operating in open air, has been reported. It has demonstrated that the crude organotellurium compound, ethyl 2-phenyltellanyl-2-methylpropionate, could mediate 2,2-azobis (isobutyronitrile) initiated styrene (St) and butyl acrylate (BA) polymerization as an LRP system. For the bulk and solution polymerization of St and the solution polymerization of BA, the molecular weights of produced polymers increased linearly with the monomer conversions. During the same time, the molecular weight distributions kept under 1.3. The UV–vis spectrum showed that the PS polymer chain bearing C-TePh end group. With the sequential monomer addition technique, a clean diblock polymer of PS-b-PBA was also obtained.