Citation: Shi Mei, Duan Xin-rui, Liu Zhao-tie, Liu Zhong-wen, Jiang Jin-qiang. Diethanol Ammonium-borate Based Polybetaine with Tunable UCST Phase Transition[J]. Chinese Journal of Polymer Science, ;2016, 34(6): 777-784. doi: 10.1007/s10118-016-1790-8 shu

Diethanol Ammonium-borate Based Polybetaine with Tunable UCST Phase Transition

Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry & Chemical Engineering, Shaanxi Normal University, Xi'an 710062, China

Corresponding author: Jiang Jin-qiang, jiangjq@snnu.edu.cn
Received Date: 27 December 2015
Revised Date: 26 January 2016

Fund Project: the Natural Science Basic Research Plan in Shaanxi Province of China NSBRP-SPC 2014JM2051the Program for Changjiang Scholars and Innovative Research Team in Universities IRT 14R33the National Natural Science Foundation of China No. 21374056the Program of Introducing Talents of Discipline to Universities B14041Shaanxi Innovative Research Team for Key Science and Technology 2012KCT-21, 2013KCT-17

A betaine-type styrene monomer with the quaternary ammonium-borate anion inner-salt pair was synthesized through the quaternization reaction and polymerized to afford the target polybetaine of poly(4-vinylbenzyl methyl-diethanol ammonium borate) (PVMAB). The chemical structures of the monomer and polymer were well demonstrated with ¹H-NMR and ¹¹B-NMR spectra analysis. The thermal-sensitive experiment showed that PVMAB in water afforded gradually well-defined sigmoidal transmittance-temperature (T-t) curves along with the increasing polymer concentration. However, the phase transition temperatures at the bottom of the S-shaped curves were always below 10 ℃ due to the very weak zwitterionic association of the ammonium-borate inner-salt pairs. The UCST phase transition could also be tuned by changing the ethanol content in the ethanol/water mixture. And the cytotoxicity experiment demonstrated the good biomimetic property of PVMAB. This study enriches the toolbox of polybetaines by introducing the quaternary ammonium-borate anion zwitterionic pair in the repeat units, therefore broadens the scope of synthetic polybetaines.
- Borate,
- Diethanol ammonium,
- Polybetaine,
- Thermal-sensitivity,
- UCST
1. [1]
  Duncan, A.J., Leo, D.J. and Long, T.E., Macromolecules, 2008, 41(21): 7765
2. [2]
  Ramos, J., Forcada, J. and Hidalgo-Alvarez, R., Chem. Rev., 2014, 114(1): 367
3. [3]
  Schlenoff, J.B., Langmuir, 2014, 30(32): 9625
4. [4]
  Lowe, A.B. and McCormick, C.L., Chem. Rev., 2002, 102(11): 4177
5. [5]
  Willcock, H., Lu, A., Hansell, C.F., Chapman, E., Collins, I.R. and O'Reilly, R.K., Polym. Chem., 2014, 5: 1023
6. [6]
  Azzaroni, O., Brown, A.A. and Huck, W.T.S., Angew. Chem., 2006, 118(11): 1802
7. [7]
  Li, W.S., Huang, L.W., Ying, X.Y., Jian, Y., Hong, Y., Hu, F.Q. and Du, Y.Z., Angew. Chem., 2015, 127(10): 3169
8. [8]
  Izumrudov, V.A., Domashenko, N.I., Zhiryakova, M.V. and Davydova, O.V., J. Phys. Chem. B, 2005, 109(37): 17391
9. [9]
  Bohrisch, J., Schimmel, T., Engelhardt, H. and Jaeger, W., Macromolecules, 2002, 35(10): 4143
10. [10]
  Azevedo, M.C.C. and Cavaleiro, A.M.V., J. Chem. Educ., 2012, 89(6): 767
11. [11]
  Cruz, G., J. Chem. Educ., 2013, 90(12): 1645
12. [12]
  Pelton, R., Hu, Z., Ketelson, H. and Meadows, D., Langmuir, 2009, 25(1): 192
13. [13]
  Shim, J., Kim, D.G., Kim, H.J., Lee, J.H. and Lee, J.C., ACS Appl. Mater. Inter., 2015, 7(14): 7690
14. [14]
  Steinberg, H. and Hunter, D.L., Ind. Eng. Chem., 1957, 49(2): 174
15. [15]
  Shen, G.Q., Zheng, Z., Wan, Y., Xu, X.D., Cao, L.L., Yue, Q.X., Sun, T.J. and Liu, A.R., Wear, 2000, 246: 55
16. [16]
  Tanner, D.W. and Bruice, T.C., J. Am. Chem. Soc., 1967, 89(26): 6954
17. [17]
  Nizioł, J., Zieliński, Z., Leś, A., Dąbrowska, M., Rode, W. and Ruman, T., Bioorgan. Med. Chem., 2014, 22(15): 3906
18. [18]
  Kim, D.J., Mun, S.D., Yoon, S., Oh, C.H., Park, H.R., You, T.S., Lee, J. and Kim, Y., Polyhedron, 2011, 30(6): 1076
19. [19]
  Qi, T., Sonoda, A., Makita, Y., Kanoh, H., Ooi, K. and Hirotsu, T., Ind. Eng. Chem. Res., 2002, 41(2): 133
20. [20]
  Liang, Z.Y., Ma, L.J., Lu, C.X. and Zhai, Y.J., J. Surfactants Deterg., 2012, 15(2): 217
21. [21]
  Miyazaki, Y., Yoshimura, K., Miura, Y., Sakashita, H. and Ishimaru, K., Polyhedron, 2003, 22(6): 909
22. [22]
  Taler, G., Schejter, A. and Navon, G., Inorg. Chim. Acta, 1998, 273: 388
23. [23]
  Miyazaki, Y., Fujimori, T., Okita, H., Hirano, T. and Yoshimura, K., Dalton Trans., 2013, 42(29): 10473
24. [24]
  Zhang, Q.L. and Hoogenboom, R., Prog. Polym. Sci., 2015, 48: 122
25. [25]
  Noskov, S.Y., Lamoureux, G. and Roux, B., J. Phys. Chem. B, 2005, 109(14): 6705
26. [26]
  Bustamante, P., Navarro, J., Romero, S. and Escalera, B., J. Pharm. Sci., 2002, 91(3): 874
27. [27]
  Hoogenboom, R., Rogers, S., Can, A., Becer, C.R., Guerrero-Sanchez, C., Wouters, D., Hoeppener, S. and Schubert, U.S., Chem. Commun., 2009, 37: 5582
28. [28]
  Twaites, B.R., Alarcón, C.H., Lavigne, M., Saulnier, A., Pennadam, S.S., Cunliffe, D., Górecki, D.C. and Alexander, C., J. Control. Release, 2005, 108: 472
29. [29]
  Tian, M., Cheng, R.D., Zhang, J., Liu, Z.T., Liu, Z.W. and Jiang, J.Q., Langmuir, 2016, 32(1): 12
30. [30]
  Geng, C.Z., Hu, X., Yang, G.H., Zhang, Q., Chen, F. and Fu, Q., Chinese J. Polym. Sci., 2015, 33(1): 61
31. [31]
  Hu, Y., Gan, L., Li, Q.X., Tao, H., Ye, L., Zhang, A.Y. and Feng, Z.G., Chinese J. Polym. Sci., 2014, 32(12): 1714
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