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
1. [1]
  Ruilong Geng , Lingzi Peng , Chang Guo . Dynamic kinetic stereodivergent transformations of propargylic ammonium salts via dual nickel and copper catalysis. Chinese Chemical Letters, 2024, 35(8): 109433-. doi: 10.1016/j.cclet.2023.109433
2. [2]
  Juan Guo , Mingyuan Fang , Qingsong Liu , Xiao Ren , Yongqiang Qiao , Mingju Chao , Erjun Liang , Qilong Gao . Zero thermal expansion in Cs₂W₃O₁₀. Chinese Chemical Letters, 2024, 35(7): 108957-. doi: 10.1016/j.cclet.2023.108957
3. [3]
  Weijian Zhang , Xianyu Deng , Liying Wang , Jian Wang , Xiuting Guo , Lianggui Huang , Xinyi Wang , Jun Wu , Linjia Jiang . Poly(ferulic acid) nanocarrier enhances chemotherapy sensitivity of acute myeloid leukemia by selectively targeting inflammatory macrophages. Chinese Chemical Letters, 2024, 35(9): 109422-. doi: 10.1016/j.cclet.2023.109422
4. [4]
  Lan Yang , Yu Li , Mou Jiang , Rui Zhou , Hengjiang Cong , Minghui Yang , Lei Zhang , Shenhui Li , Yunhuang Yang , Maili Liu , Xin Zhou , Zhong-Xing Jiang , Shizhen Chen . Fluorinated [2]rotaxanes as sensitive ¹⁹F MRI agents: Threading for higher sensitivity. Chinese Chemical Letters, 2024, 35(10): 109512-. doi: 10.1016/j.cclet.2024.109512
5. [5]
  Junmei FAN , Wei LIU , Ruitao ZHU , Chenxi QIN , Xiaoling LEI , Haotian WANG , Jiao WANG , Hongfei HAN . High sensitivity detection of baicalein by N, S co-doped carbon dots and their application in biofluids. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2009-2020. doi: 10.11862/CJIC.20240120
6. [6]
  Huihui LIU , Baichuan ZHAO , Chuanhui WANG , Zhi WANG , Congyun ZHANG . Green synthesis of MIL-101/Au composite particles and their sensitivity to Raman detection of thiram. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2021-2030. doi: 10.11862/CJIC.20240059
7. [7]
  Ruizhi Yang , Xia Li , Weiping Guo , Zixuan Chen , Hongwei Ming , Zhong-Zhen Luo , Zhigang Zou . New thermoelectric semiconductors Pb5Sb12+xBi6-xSe32 with ultralow thermal conductivity. Chinese Journal of Structural Chemistry, 2024, 43(3): 100268-100268. doi: 10.1016/j.cjsc.2024.100268
8. [8]
  Chaozheng He , Pei Shi , Donglin Pang , Zhanying Zhang , Long Lin , Yingchun Ding . First-principles study of the relationship between the formation of single atom catalysts and lattice thermal conductivity. Chinese Chemical Letters, 2024, 35(6): 109116-. doi: 10.1016/j.cclet.2023.109116
9. [9]
  Yi Herng Chan , Zhe Phak Chan , Serene Sow Mun Lock , Chung Loong Yiin , Shin Ying Foong , Mee Kee Wong , Muhammad Anwar Ishak , Ven Chian Quek , Shengbo Ge , Su Shiung Lam . Thermal pyrolysis conversion of methane to hydrogen (H₂): A review on process parameters, reaction kinetics and techno-economic analysis. Chinese Chemical Letters, 2024, 35(8): 109329-. doi: 10.1016/j.cclet.2023.109329
10. [10]
  Rongliang Deng , Yihang Chen , Xiaotong Fan , Guolong Chen , Shuli Wang , Changzhi Yu , Xiao Yang , Tingzhu Wu , Zhong Chen , Yue Lin . Break of thermal equilibrium between optical and acoustic phonon branches of CsPbI₃ under continuous-wave light excitation and cryogenic temperature. Chinese Chemical Letters, 2024, 35(7): 109346-. doi: 10.1016/j.cclet.2023.109346
11. [11]
  Hong Chen , Mao-Yin Ran , Long-Hua Li , Xin-Tao Wu , Hua Lin . [Cs14Cl][Tm71Se110]: An unusual salt-inclusion chalcogenide containing different valent Tm centers and ultralow thermal conductivity. Chinese Journal of Structural Chemistry, 2024, 43(10): 100397-100397. doi: 10.1016/j.cjsc.2024.100397

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(587)
HTML views(2)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142