A Convenient Dual-Side Anionic Initiator Based on 2,6-Luditine/s-Butyl Lithium

Wu Bin Ying; Na Yeong Ko; Chen Kai Yao; Nho Hoon Kwak; Ruoyu Zhang; Kyung Jin Lee; Bumjae Lee

Macromolecular Research, Vol.27, No.6, 601-605, June, 2019

DOI10.1007/s13233-019-7096-2 Export Citation

A Convenient Dual-Side Anionic Initiator Based on 2,6-Luditine/s-Butyl Lithium

Wu Bin Ying, Na Yeong Ko¹, Chen Kai Yao, Nho Hoon Kwak¹, Ruoyu Zhang^†, Kyung Jin Lee^{1, †}, and Bumjae Lee^{1, †}

Key Laboratory of Bio-Based Polymeric Materials Technology and Application of Zhejiang Province, Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, No. 1219, West Zhongguan Road, Zhenhai District, Ningbo, Zhejiang 315201, P. R. China
¹Department of Fine Chemical Engineering and Applied Chemistry, College of Engineering, Chungnam National University, 99 Daehak-ro (st), Yuseong-gu, Daejeon 34134, Korea

E-mail:, ,

A novel convenient dual-side initiator of lutidine dianion for anionic polymerization has been investigated in terms of their initiation and propagation kinetics. This lutidine dianion could be synthesized in quantitative yields reacting commercial products of 2,6-lutidine with sec-butyl lithium without any complex organic synthesis, and could be used effectively as the dual-side initiator to synthesize polyisoprene with various molecular weights via living anionic polymerization. In addition, this lutidine dianion can produce 50% of 1.4-microstructure contents in polyisoprene which is very important for elastomeric property of polydienes. All experimental evidences showed the living property and were consistent with quantitative yields without any side reactions when the anionic living polymerization proceeded using lutidine dianion as the initiator.

Keywords:living anionic polymerization;dual-side initiator;lutidine;polyisoprene

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[2] Vasilakopoulos TC, Hadjichristidis N, J. Polym. Sci. A: Polym. Chem., 51, 824 (2012)

[3] Liu BX, Quirk RP, Wesdemiotis C, Yol AM, Foster MD, Macromolecules, 45(23), 9233 (2012)

[4] Schultz AR, Bobade S, Scott PJ, Long TE, Macromol. Chem. Phys., 219, 170020 (2018)

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[6] Zhang H, He J, Zhang C, Ju Z, Li J, Yang Y, Macromolecules, 45, 828 (2011)

[7] Riess G, Hurtrez G, in Encyclopedia of Polymer Science and Engineering, Wiley-Interscience, New York, p.324 1985.

[8] Quirk RP, Ma JJ, Polym. Int., 24, 197 (1991)

[9] Bywater S, in Encyclopedia of Polymer Science and Engineering, Wiley-Interscience, New York, p.1 1985.

[10] Hsieh HL, Quirk RP, in Anionic Polymerization: Principles and Practical Applications, Marcel Dekker, New York, p 110 1996.

[11] Estrin YI, Tarasov AE, Grishchuk AA, Chernyak AV, Badamshina ER, RSC Adv., 6, 106064 (2016)

[12] Huang M, Lu J, Han B, Liu J, Qiao H, Zhang L, J. Appl. Polym. Sci., 134, 44923 (2017)

[13] Lu W, Huang CL, Hong KL, Kang NG, Mays JW, Macromolecules, 49(24), 9406 (2016)

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[18] Jou CD, Hsieh HC, Tsiang RC, Polymer, 38(23), 5869 (1997)

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[23] Yu YS, Jerome R, Fayt R, Teyssie P, Macromolecules, 27(21), 5957 (1994)

[24] Cameron GG, Buchan GM, Polymer, 20, 1129 (1979)

[25] Hsieh HL, Quirk RP, in Anionic Polymerization: Principles and Practical Applications, Marcel Dekker, Inc., New York, p17 1996.

[26] Lipkowitz KB, Uhegbu C, Naylor AM, Vance R, J. Comput. Chem., 6, 662 (1985)

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[29] Quirk RP, McFay D, J. Polym. Sci. A: Polym. Chem., 24, 827 (1986)

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