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]
  Yangfeifei Ou , Xiao-Liang Zhou , You-Zhao Lan , Jian-Wen Cheng . Borosilicates as deep-ultraviolet transparent nonlinear optical crystals: Structural motifs, performance limits and future directions. Chinese Journal of Structural Chemistry, 2025, 44(9): 100708-100708. doi: 10.1016/j.cjsc.2025.100708
2. [2]
  Peng Guo , Shicheng Dong , Xiang-Gui Zhang , Bing-Bin Yang , Jun Zhu , Ke-Yin Ye . Cobalt-catalyzed migratory carbon-carbon cross-coupling of borabicyclo[3.3.1]nonane (9-BBN) borates. Chinese Chemical Letters, 2025, 36(4): 110052-. doi: 10.1016/j.cclet.2024.110052
3. [3]
  Ning Yang , Huijian Zhao , Wenli Zhao , Yuheng She , Ning Ye , Zhanggui Hu , Conggang Li . Assembly of π-conjugated [B₃O₇] groups by unprecedented antiparallel triangles [ZnO₃] to tailor a deep-UV zinc borate birefringent crystal. Chinese Chemical Letters, 2026, 37(4): 110825-. doi: 10.1016/j.cclet.2025.110825
4. [4]
  Saima Perveen , Xicheng Wang , Tao Li , Linghua Wang , Shuai Zhang , Yizhao Ouyang , Xue Zhao , Liang Xu , Pengfei Li . Enantioconvergent reductive amidation of benzyl ammonium salts for synthesis of α-chiral amides. Chinese Chemical Letters, 2026, 37(1): 111779-. doi: 10.1016/j.cclet.2025.111779
5. [5]
  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
6. [6]
  Quanxing Mao , Zhengliang Wang , Zhinan Hu , Ziqi Yang , Hui Li , Yali Yao , Zijun Yong , Tianyi Ma . Facial detection of formaldehyde by using acidichromic carbon dots and the reaction between formaldehyde and ammonium chloride. Chinese Chemical Letters, 2025, 36(7): 110499-. doi: 10.1016/j.cclet.2024.110499
7. [7]
  Xue Du , Ze-Hua Sun , Penglei Zhang , Li-Ping Xu , Xiaodong Xiong . Asymmetric chloro– and selenocyclization of 2-alkenyl anilides enabled by tertiary ammonium salt catalysis. Chinese Chemical Letters, 2026, 37(4): 111259-. doi: 10.1016/j.cclet.2025.111259
8. [8]
  Xiaojun Wang , Yizhou Zhang , Linwei Guo , Jianwei Li , Peng Wang , Lei Yang , Zhiming Liu . V₂CT_X MXene-derived ammonium vanadate with robust carbon skeleton for superior rate aqueous zinc-ion batteries. Chinese Chemical Letters, 2025, 36(8): 111231-. doi: 10.1016/j.cclet.2025.111231
9. [9]
  Zerui Deng , Xincheng Liang , Xingfa Chen , Yuquan Gou , Anning Wang , Peixin Xie , Qian Liu , Huan Wen , Shibin Yin . The role of ammonium formate electrolyte additive for aqueous zinc-ion batteries: Inducing Zn(002) deposition and suppressing hydrogen evolution. Chinese Journal of Structural Chemistry, 2025, 44(11): 100706-100706. doi: 10.1016/j.cjsc.2025.100706
10. [10]
  Ruijing Fu , Bin Xiao , Haoyuan Weng , Pan Wang , Guangxia Wang , Qingguang Zeng , Dawei Wen , Guanjun Xiao . An optical pressure sensing phosphor of high-sensitivity by soft structure. Chinese Chemical Letters, 2026, 37(3): 111916-. doi: 10.1016/j.cclet.2025.111916
11. [11]
  Zihan Wang , Meizhen Dai , Pengcheng Song , Wenxuan Liu , Junhua You , Fang Hu , Yusheng Wu , Kai Zhu . Triply stabilized NH₄V₄O₁₀ via glycine pillaring enables universal cathode for outstanding rate aqueous zinc-ion batteries and stable aqueous ammonium-ion batteries. Chinese Chemical Letters, 2026, 37(4): 111729-. doi: 10.1016/j.cclet.2025.111729
12. [12]
  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
13. [13]
  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
14. [14]
  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
15. [15]
  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
16. [16]
  Shangda Qu , Yiming Yuan , Xu Ye , Wentao Xu . High sensitivity artificial synapses using printed high-transmittance ITO fibers for neuromorphic computing. Chinese Chemical Letters, 2024, 35(12): 110030-. doi: 10.1016/j.cclet.2024.110030
17. [17]
  Zhaoyu Liu , Dan Wang , Guohui Liu , Huili Zhang , He Li , Xiaoju Li , Ruihu Wang . Sound-Bioinspired Dual-Conductive Hydrogel Sensors for High Sensitivity and Environmental Weatherability. Chinese Journal of Structural Chemistry, 2025, 44(8): 100628-100628. doi: 10.1016/j.cjsc.2025.100628
18. [18]
  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
19. [19]
  Zihe SONG , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Crystal structure, thermal analysis, and luminescence properties of six heterocyclic lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 181-192. doi: 10.11862/CJIC.20250126
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1665)
HTML views(30)

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