Citation: Hua-qing Liang, Qi-hua Zhou, Yong-jiang Long, Wan-chu Wei, Guo-dong Liang, Qing Wu, Hai-yang Gao, Fang-ming Zhu. Synthesis of Isotactic Polystyrene-block-Polyethylene by the Combination of Sequential Monomer Addition and Hydrogenation of 1, 4-Trans-polybutadiene Block[J]. Chinese Journal of Polymer Science, ;2017, 35(7): 866-873. doi: 10.1007/s10118-017-1933-6 shu

Synthesis of Isotactic Polystyrene-block-Polyethylene by the Combination of Sequential Monomer Addition and Hydrogenation of 1, 4-Trans-polybutadiene Block

a.
Guangdong Provincial Key Laboratory for High Performance Polymeric Composites, School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275, China
b.
Key Laboratory for Polymer Composite and Functional Materials of Ministry of Education, School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275, China

Corresponding author: Fang-ming Zhu, ceszfm@mail.sysu.edu.cn
Received Date: 7 December 2016
Revised Date: 3 January 2017
Accepted Date: 14 January 2017

Fund Project: the National Natural Science Foundation of China 51573212the Natural Science Foundation of Guangdong Province Nos. S2013030013474the Natural Science Foundation of Guangdong Province 2014A030313178the National Natural Science Foundation of China Nos. 21174167

Herein, we demonstrate the synthesis of a well-defined diblock copolymer consisting of isotactic polystyrene (iPS) and linear polyethylene, isotactic polystyrene-block-polyethylene (iPS-b-PE), by the combination of sequential monomer addition and hydrogenation. Isospecific living polymerization of styrene and living trans-1,4-polymerization of 1,3-butadiene were catalyzed by 1,4-dithiabutandiyl-2,2′-bis(6-cumenyl-4-methylphenoxy) titanium dichloride (complex 1) activated by triisobutyl aluminum modified methylaluminoxane (MMAO) at room temperature to provide highly isotactic polystyrene (iPS) and 1,4-trans-polybutadiene (1,4-trans-PBD) with narrow molecular weight distribution. Furthermore, the iPS-b-1,4-trans-PBD was synthesized via sequential monomer addition in the presence of complex 1 and MMAO. The hydrogenation of the 1,4-trans-PBD block was promoted by RuCl₂(PPh₃)₃ used as a catalyst to produce iPS-b-PE.
- Isotactic polystyrene,
- 1, 4-Trans-polybutadiene,
- Linear polyethylene,
- Diblock copolymer,
- Sequential monomer addition,
- Hydrogenation
1. [1]
  Park, C., Yoon, J. and Thomas, E.L., Polymer, 2003, 44: 6725 doi: 10.1016/j.polymer.2003.08.011
2. [2]
  Jin, K.K., Yang, S.Y., Lee, Y. and Kim, Y., Prog. Polym. Sci., 2010, 35: 1325 doi: 10.1016/j.progpolymsci.2010.06.002
3. [3]
  Kim, H.J., Kim, J.H., Ryu, J.H., Kim, Y., Kang, H., Lee, W.B., Kim, T.S. and Kim, B.J., ACS Nano, 2014, 8: 10461 doi: 10.1021/nn503823z
4. [4]
  Pandav, G. and Ganesan, V., Macromolecules, 2015, 73: 16
5. [5]
  Fujita, H., Michinobu, T., Fukuta, S., Koganezawa, T. and Higashihara, T., ACS Appl. Mater. Interfaces, 2016, 8: 5484 doi: 10.1021/acsami.5b12437
6. [6]
  Wu, M., Wu, Z., Wang, K., Zhang, Q. and Fu, Q., Polymer, 2014, 55: 6409 doi: 10.1016/j.polymer.2014.10.004
7. [7]
  Wu, H., Jiang, T., Zhu, J., Cui, K., Zhao, Q. and Ma, Z., J. Polym. Sci., Part A: Polym. Chem., 2015, 8: 341
8. [8]
  Chen, L., Zhang, C., Du, Z., Li, H., Zhang, L. and Wei, Z., RSC Adv., 2015, 5: 65184 doi: 10.1039/C5RA10197B
9. [9]
  Raynaud, J., Liu, N., Gnanou, Y. and Taton, D., Polym. Chem., 2011, 2: 1706 doi: 10.1039/c1py00077b
10. [10]
  Wu, Z.Q., Chen, Y., Wang, Y., He, X.Y., Ding, Y.S. and Liu, N., Chem. Commun., 2013, 49: 8069 doi: 10.1039/c3cc43026j
11. [11]
  Yang, J.X., Long, Y.Y., Pan, L., Men, Y.F. and Li, Y.S., ACS Appl. Mater. Interfaces, 2016, 8: 12445 doi: 10.1021/acsami.6b02073
12. [12]
  Wu, J., Jiang, H., Zhang, L., Cheng, Z. and Zhu, X., Polym. Chem., 2016, 7: 2486 doi: 10.1039/C6PY00199H
13. [13]
  Tanaka, S., Goseki, R., Ishizone, T. and Hirao, A., Macromolecules, 2014, 47: 934
14. [14]
  Ren, Y., Wei, Z., Leng, X., Wang, Y. and Li, Y., Polymer, 2015, 78: 51 doi: 10.1016/j.polymer.2015.09.063
15. [15]
  Todd, A.D. and Bielawski, C.W., ACS Macro Lett., 2015, 4: 1254 doi: 10.1021/acsmacrolett.5b00505
16. [16]
  Anastasaki, A., Waldron, C., Wilson, P., Boyer, C., Zetterlund, P.B., Whittaker, M.R. and Haddleton, D., ACS Macro Lett., 2013, 2: 896 doi: 10.1021/mz4004198
17. [17]
  Goseki, R., Onuki, S., Tanaka, S., Ishizone, T. and Hirao, A., Macromolecules, 2015, 48: 3230 doi: 10.1021/acs.macromol.5b00575
18. [18]
  Leone, G., Polym. Chem., 2012, 3: 1987 doi: 10.1039/c2py20218b
19. [19]
  Kima, D.G., Bell, A. and Register, R.A., ACS Macro Lett., 2015, 4: 327 doi: 10.1021/acsmacrolett.5b00079
20. [20]
  Capacchione, C., Saviello, D., Ricciardi, R. and Proto, A., Macromolecules, 2011, 44: 7940 doi: 10.1021/ma201442w
21. [21]
  Kobayashi, E., Hayashi, N., Aoshima, S. and Furukawa, J., J. Polym. Sci., Part. A: Polym. Chem., 1998, 36: 241 doi: 10.1002/(ISSN)1099-0518
22. [22]
  Kaita, S., Hou, Z. and Wakatsuki, Y., Macromolecules, 2001, 34: 1539 doi: 10.1021/ma001609n
23. [23]
  Monteil, V., Spitz, R. and Boisson, C., Polym. Int., 2004, 53: 576 doi: 10.1002/(ISSN)1097-0126
24. [24]
  Ventura, A., Chenal, T., Bria, M., Bonnet, F., Zinck, P., Ravache, Y.N., Balanzat, E. and Visseaux, M., Eur. Polym. J., 2013, 49: 4130 doi: 10.1016/j.eurpolymj.2013.09.019
25. [25]
  Jian, Z., Tang, S. and Cui, D., Chem. Eur. J., 2010, 16: 14007 doi: 10.1002/chem.v16.47
26. [26]
  Proto, A., Avagliano, A., Saviello, D., Ricciardi, R. and Capacchione, C., Macromolecules, 2010, 43: 5919 doi: 10.1021/ma101246x
27. [27]
  Capacchione, C., Proto, A., Ebeling, H., Mulhaupt, R., Moller, K., Spaniol, T.P. and Okuda, J., J. Am. Chem. Soc., 2003, 125: 4964 doi: 10.1021/ja029968g
28. [28]
  Beckerle, K., Manivannan, R., Spaniol, T.P. and Okuda, J., Organometallics, 2006, 25: 3019 doi: 10.1021/om060047e
29. [29]
  Buwalda, S.J., Amgoune, A. and Bourissou, D., J. Polym. Sci., Part. A: Polym. Chem., 2015, 54: 1222
30. [30]
  Reuther, J.F., Bhatt, M.P., Tian, G., Batchelor, B.L., Campos, R. and Novak, B.M., Macromolecules, 2014, 47: 4587 doi: 10.1021/ma5009429
31. [31]
  Chen, Y.J., Wu, B.J., Wang, F.S., Chi, M.H., Chen, J.T. and Peng, C.H., Macromolecules, 2015, 48: 6832 doi: 10.1021/acs.macromol.5b01101
32. [32]
  Yang, Y. and Knauss, D.M., Macromolecules, 2015, 48: 4471 doi: 10.1021/acs.macromol.5b00459
33. [33]
  Stalmach, U., Boer, B.D., Videlot, C., Hutten, P.F.V. and Hadziioannou, G., J. Am. Chem. Soc., 2000, 122: 5464 doi: 10.1021/ja000160a
34. [34]
  Piunova, V.A., Horn, H.W., Jones, G.O., Rice, J.E. and Miller, R.D., J. Polym. Sci., Part A: Polym. Chem., 2016, 54: 563 doi: 10.1002/pola.27807
35. [35]
  Zhang, Z., Altaher, M., Zhang, H., Wang, D. and Hadjichristidis, N., Macromolecules, 2016, 49: 2630 doi: 10.1021/acs.macromol.6b00291
36. [36]
  Pottier, C., Morandi, G., Dulong, V., Souguir, Z., Picton, L. and Cerf, D.L., J. Polym. Sci., Part A: Polym. Chem., 2015, 53: 2606 doi: 10.1002/pola.v53.22
37. [37]
  Hu, Y., Darcos, V., Monge, S. and Li, S., Int. J. Pharmaceut., 2015, 491: 152 doi: 10.1016/j.ijpharm.2015.06.020
38. [38]
  Alkayal, N., Polym. Chem., 2016, 7: 2986 doi: 10.1039/C6PY00331A
39. [39]
  Bellas, V. and Rehahn, M., Macromol. Chem. Phys., 2009, 210: 320 doi: 10.1002/macp.v210:5
40. [40]
  Hoyle, C.E. and Bowman, C.N., Angew. Chem. Int. Ed., 2010, 49: 1540 doi: 10.1002/anie.200903924
41. [41]
  Tsuchiya, K., Ando, K., Shimomura, T. and Ogino, K., Polymer, 2016, 92: 125 doi: 10.1016/j.polymer.2016.03.092
42. [42]
  Park, J., Lee, K.S., Choi, C., Kwak, J., Moon, H.C. and Kim, J.K., Macromolecules, 2016, 49: 3647 doi: 10.1021/acs.macromol.6b00513
43. [43]
  Pessoni, L., Winter, J.D., Surin, M., Hergué, N., Delbosc, N., Lazzaroni, R., Dubois, P., Gerbaux, P. and Coulembier, O., Macromolecules, 2016, 49: 3001 doi: 10.1021/acs.macromol.6b00283
44. [44]
  Guillaume, G., Roberts, D.A., Thomas, M. and Sébastien, P., J. Am. Chem. Soc., 2016, 138: 4061 doi: 10.1021/jacs.5b11831
45. [45]
  Xu, J., Ye, J. and Liu, S., Macromolecules, 2007, 40: 203
46. [46]
  Soeriyadi, A.H., Boyer, C., Nyström, F., Zetterlund, P.B. and Whittaker, M.R., J. Am. Chem. Soc., 2011, 133: 11128 doi: 10.1021/ja205080u
47. [47]
  Hansell, C.F., Espeel, P., Stamenovi, M.M., Barker, I.A., Dove, A.P., Prez, F.E.D. and O'Reilly, R.K., J. Am. Chem. Soc., 2011, 133: 13828 doi: 10.1021/ja203957h
48. [48]
  Li, T., Wang, W.J., Liu, R., Liang, W.H., Zhao, G.F., Li, Z.Y., Wu, Q. and Zhu, F.M., Macromolecules, 2009, 42: 3804 doi: 10.1021/ma900182s
49. [49]
  Li, Z.Y., Liu, R., Mai, B.Y., Feng, S., Wu, Q., Liang, G.D., Gao, H.Y. and Zhu, F.M., Polym. Chem., 2013, 4: 954 doi: 10.1039/C2PY20814H
50. [50]
  Ferrer, M. D. P. and Calle, J. A. B. , 1996, U. S. Pat. , 5, 583, 185
51. [51]
  Chamberlain, L. R. and Gibler, C. J. , 1991, U. S. Pat. , 5, 039, 755
52. [52]
  Gibler, C. J. and Wilson, S. E. , 1993, U. S. Pat. , 5, 244, 980
53. [53]
  Mohammadi, N.A. and Rempel, G.L., J. Mol. Catal., 1989, 50: 259 doi: 10.1016/0304-5102(89)80284-6
54. [54]
  Guo, X. and Rempel, G.L., J. Mol. Catal., 1990, 63: 279 doi: 10.1016/0304-5102(90)85120-7
55. [55]
  Guo, X., Scott, P.J. and Rempel, G.L., J. Mol. Catal., 1992, 72: 193 doi: 10.1016/0304-5102(92)80045-I
56. [56]
  Hahn, S.F., J. Polym. Sci., Part A: Polym. Chem., 1992, 30: 397 doi: 10.1002/pola.1992.080300307
57. [57]
  Petzetakis, N., Stone, G.M. and Balsara, N.P., Macromolecules, 2014, 47: 4151 doi: 10.1021/ma500686k
58. [58]
  Caporaso, L., Izzo, L., Sisti, I. and Oliva, L., Macromolecules, 2002, 35: 4866 doi: 10.1021/ma011489z
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