两性离子聚合物是在高分子链段上包含丰富等量阴离子基团与阳离子基团的聚合物，因具备优异的亲水性、生物相容性等独特的性质，近年来在抗污染、生物医药等领域展示了极广阔的应用前景。按照其结构特征，可以大体被分为混合电荷型与甜菜碱型两性离子聚合物。目前两性离子聚合物的制备方法多种多样，从实际应用的角度出发，使用“活性”/可控自由基聚合制备两性离子聚合物具有独特的优势，如分子量可控、易于制备复杂结构聚合物等，这些特性拓宽了两性离子聚合物的应用领域。本文沿“单体直接聚合”和“聚合物后修饰”两条路径，介绍了使用“活性”/可控自由基聚合制备两性离子聚合物的优势及进展，同时从抗污染材料、生物医药材料、物质检测与分离等方面概述了两性离子聚合物的主要应用，并对其未来发展作出展望。
Zwitterionic polymer is a polymer with equivalent positive and negative charge groups on the polymer chains. It is widely used in the areas of anti-fouling and biomedical applications due to its super-hydrophilic and biocompatible properties. Based on their structural features, they can be broadly divided into mixed-charge type and betaine type zwitterionic polymers. At present, zwitterionic polymers can be prepared in a variety of methods, among which living/controlled radical polymerization is a robust and versatile method for the preparation of zwitterionic materials. This approach allows preparation of polymers with precise control over molecular weight, molecular weight distribution, polymer composition, topology and functionality. In this paper, the synthesis of zwitterionic polymers and its recent development are critically reviewed. We mainly focus on the advantages and development of living/controlled radical polymerization for preparing zwitterionic polymers. The main applications of zwitterionic polymers as anti-fouling materials, biomedical materials, detection and separation are summarized and the prospect of their future development is also outlined.
Contents
1 Introduction
2 Synthesis of zwitterionic polymers by living/controlled radical polymerization.
2.1 Preparation of mixed-charge type polymers
2.2 Preparation of betaine type polymers
3 Applications of zwitterionic polymers
3.1 Industrial materials
3.2 Biomedical materials
4 Conclusion and outlook
[1] Lowe A B, McCormick C L. Chem. Rev., 2002, 102(11):4177.
[2] 王中华(Wang Z H). 中外能源(Sino-global Energy), 2013, 18(10):34.
[3] Beltrán-Osuna Á A, Cao B, Cheng G, Jana S C, Espe M P, Lama B. Langmuir, 2012, 28(25):9700.
[4] 陈杨军(Chen Y J), 刘湘圣(Liu X S), 王海波(Wang H B), 王寅(Wang Y), 金桥(Jin Q), 计剑(Ji J). 化学进展(Prog. Chem.), 2014, 26(11):1849.
[5] Ni L, Meng J Q, Geise G M, Zhang Y F, Zhou J. J. Membrane Sci., 2015, 491:73.
[6] Stach H. Angew. Chem. Int. Ed., 1951, 63:263.
[7] Chen S F, Jiang S Y. Adv. Mater., 2008, 20(2):335.
[8] Huang Y, Tang Z, Zhang X, Yu H, Sun H, Pang X, Chen X. Biomacromolecules, 2013, 14(6):2023.
[9] Shao Q, Mi L, Han X, Bai T, Liu S J, Li Y T, Jiang S Y. J. Phys. Chem. B, 2014, 118(24):6956.
[10] Shao Q, Jiang S Y. J. Phys. Chem. B, 2014, 118(27):7630.
[11] Higaki Y, Inutsuka Y, Sakamaki T, Terayama Y, Takenaka A, Higaki K, Yamada N L, Moriwaki T, Ikemoto Y, Takahara A. Langmuir, 2017, 33(34):8404.
[12] Zhu Y C, Batchelor R, Lowe A B, Roth P J. Macromolecules, 2016, 49(2):672.
[13] Kumar R, Fredrickson G H. J. Chem. Phys., 2009, 131(10):104901.
[14] Rajan R, Matsumura K. Macromol. Rapid Commun., 2017, 38(22):1700478.
[15] Shao Q, Jiang S. Adv. Mater., 2015, 27(1):15.
[16] Mary P, Bendejacq D D, Labeau M, Dupuis P. J. Phys. Chem. B, 2007, 111(27):7767.
[17] Georgiev G S, Kamenska E B, Vassileva E D, Kamenova I P, Georgieva V T, Iliev S B, Ivanov I A. Biomacromolecules, 2006, 7(4):1329.
[18] Laschewsky, A. Polymers, 2014, 6(5):1544.
[19] Georges M K, Veregin R P, Kazmaier P M, Hamer G K. Macromolecules, 1993, 26(11):2987.
[20] Kazmaier P M, Daimon K, Georges M K, Hamer G K, Veregin R P N. Macromolecules, 1997, 30(8):2228.
[21] Xia J H, Matyjaszewski K. Macromolecules, 1997, 30(25):7697.
[22] Chiefari J, Chong Y K, Ercole F, Krstina J, Jeffery J, Le T P, Mayadunne R T, Meijs G F, Moad C L, Moad G, Rizzardo E, Thang S H. Macromolecules, 1998, 31(16):5559.
[23] Chiefari J, Mayadunne R T, Moad C L, Moad G, Rizzardo E, Postma A, Skidmore M A, Thang S H. Macromolecules, 2003, 36(7):2273.
[24] Moad G, Rizzardo E, Thang S H. Aust. J. Chem., 2005, 58(6):379.
[25] Perrier S. Macromolecules, 2017, 50(19):7433.
[26] 郭晓峰(Guo X F), 潘翔宇(Pan X Y), 魏晓虎(Wei X H), 冯岸超(Feng A C), 汤华燊(Thang S H). 化学进展(Prog. Chem.), 2017, 29(10):1184.
[27] Khabibullin A, Mastan E, Matyjaszewski K, Zhu S P. Controlled Radical Polymerization at and from Solid Surfaces, NY:Springer, 2015, 29.
[28] Chen X J, Lawrence J, Parelkar S, Emrick T. Macromolecules, 2012, 46(1):119.
[29] Silies L, Didzoleit H, Hess C, Stühn B, Andrieu-Brunsen A. Chem. Mater., 2015, 27(6):1971.
[30] Ma G L, Lin W F, Yuan Z F, Wu J, Qian H F, Xu L B, Chen S F. J. Mater. Chem. B, 2017, 5(5):935.
[31] Venault A, Hsu K J, Yeh L C, Chinnathambi A, Ho H T, Chang Y. Colloid. Surface. B, 2017, 151:372.
[32] Chang Y, Shu S H, Shih Y J, Chu C W, Ruan R C, Chen W Y. Langmuir, 2010, 26(5):3522.
[33] Mi L, Bernards M T, Cheng G, Yu Q M, Jiang S Y. Biomaterials, 2010, 31(10):2919.
[34] Canning S L, Neal T J, Armes S P. Macromolecules, 2017, 50(16):6108.
[35] Cheng G, Xue H, Zhang Z, Chen S F, Jiang S Y. Angew. Chem. Int. Ed., 2008, 47(46):8831.
[36] Liu J, Zhou J. Acta Biomater., 2016, 40:23.
[37] Das S, Santra S, Mondal P, Majee A, Hajra A. Synthesis, 2016, 48(09):1269.
[38] 牛瑞霞(Niu R X), 任伟东(Ren W D), 孙双波(Sun S B), 宋华(Song H), 李征鸿(Li Z H). 化工进展(Chem. Ind. Eng. Prog.), 2013, (8):1887.
[39] Chou Y N, Wen T C, Chang Y. Acta Biomater., 2016, 40:78.
[40] Sivashanmugan K, Liu P C, Tsai K W, Chou Y N, Lin C H, Chang Y, Wen T C. Nanoscale, 2017, 9(8):2865.
[41] Yuan J, Huang X B, Li P F, Li L, Shen J. Polym. Chem., 2013, 4(19):5074.
[42] 蒋川(Jiang C), 成煦(Cheng X), 杜宗良(Du Z L). 皮革科学与工程(Leather Sci. Eng.), 2015, (02):12.
[43] Jackson M A, Werfel T A, Curvino E J, Yu F, Kavanaugh T E, Sarett S M, Dockery M D, Kilchrist K V, Jackson A N, Giorgio T D, Duvall C L. ACS Nano, 2017, 11(6):5680.
[44] He X Y, Qiang S L, Liu Z, Wang M, Yang W. RSC Adv., 2015, 5(122):101055.
[45] Jangu C, Wang J H, Wang D, Fahs G, Heflin J R, Moore R B, Colby R H, Long T E. J. Mater. Chem. C, 2015, 3(16):3891.
[46] Ezzat M, Huang C. RSC Adv., 2016, 6(66):61695.
[47] Zhao W W, Ye Q, Hu H Y, Wang X L, Zhou F. J. Mater. Chem. B, 2014, 2(33):5352.
[48] Li B, Yu B, Huck W T, Zhou F, Liu W M. Angew. Chem. Int. Ed., 2012, 51(21):5092.
[49] Li B, Yu B, Zhou F. Macromol. Rapid Commun., 2013, 34(3):246.
[50] Li B, Yu B, Huck W T, Liu W M, Zhou F. J. Am. Chem. Soc., 2013, 135(5):1708.
[51] Chmielarz P, Fantin M, Park S, Isse A A, Gennaro A, Magenau A J, Sobkowiak A, Matyjaszewski K. Prog. Polym. Sci., 2017, 69:47.
[52] Pan X C, Tasdelen M A, Laun J, Junkers T, Yagci Y, Matyjaszewski K. Prog. Polym. Sci., 2016, 62:73.
[53] Magenau A, Strandwitz N C, Gennaro A, Matyjaszewski K. Science, 2011, 332(6025):81.
[54] Hong D W, Hung H C, Wu K, Lin X J, Sun F, Zhang P, Liu S J, Cook K E, Jiang S Y. ACS Appl. Mater. Inter., 2017, 9(11):9255.
[55] Raymo F M, Giordani S. J. Am. Chem. Soc., 2001, 123(19):4651.
[56] Cao Z Q, Bian Q, Chen Y, Liang F X, Wang G J. ACS Macro Lett., 2017, 6(10):1124.
[57] Chen J, Zhong W B, Xue M J, Wang H, Yu M L, Zhang P S, Yi P G. Polym. Chem., 2017, 8(42):6520.
[58] Jin Q, Liu G Y, Ji J. J. Polym. Sci. Pol. Chem., 2010, 48(13):2855.
[59] Mi Y F, Zhao F Y, Guo Y S, Weng X D, Ye C C, An Q F. J. Membrane Sci., 2017, 541:29.
[60] Chen S J, Mei Z K, Ren H H, Zhuo H T, Liu J H, Ge Z C. Polym. Chem., 2016, 7(37):5773.
[61] Billing M, Elter J K, Schacher F H. Polymer, 2016, 104:40.
[62] Sundaram H S, Ella-Menye J, Brault N D, Shao Q, Jiang S Y. Chem. Sci., 2014, 5(1):200.
[63] Hung H C, Jain P, Zhang P, Sun F, Sinclair A, Bai T, Li B W, Wu K, Tsao C, Liu E J, Sundaram H S, Lin X J, Farahani P, Fujihara T, Jiang S Y. Adv. Mater., 2017, 29(31):1700617.
[64] 陈杰(Chen J), 李小舟(Li X Z), 田华雨(Tian H Y), 朱筱娟(Zhu X J), 陈学思(Chen X S). 高等学校化学学报(Chem. J. Chin. Univ.), 2015, 36(11):2148.
[65] Zheng L C, Sundaram H S, Wei Z Y, Li C C, Yuan Z F. React. Funct. Polym., 2017, 118:51.
[66] Leng C, Hung H C, Sun S W, Wang D Y, Li Y T, Jiang S Y, Chen Z. ACS Appl. Mater. Inter., 2015, 7(30):16881.
[67] Chen M, Briscoe W H, Armes S P, Klein J. Science, 2009, 323(5922):1698.
[68] Wu J, Lin W F, Wang Z, Chen S F, Chang Y. Langmuir, 2012, 28(19):7436.
[69] He M R, Gao K, Zhou L J, Jiao Z W, Wu M Y, Cao J L, You X D, Cai Z Y, Su Y L, Jiang Z Y. Acta Biomater., 2016, 40:142.
[70] Shahkaramipour N, Tran T, Ramanan S, Lin H. Membranes, 2017, 7(1):13.
[71] Guo S, Jańczewski D, Zhu X, Quintana R, He T, Neoh K G. J. Colloid Interf. Sci., 2015, 452:43.
[72] Chen K, Hu F L, Gu H C, Xu H. J. Mater. Chem. B, 2017, 5(3):435.
[73] Abraham S, So A, Unsworth L D. Biomacromolecules, 2011, 12(10):3567.
[74] Lee H, Dellatore S M, Miller W M, Messersmith P B. Science, 2007, 318(5849):426.
[75] Kang X M, Cai W H, Zhang S, Cui S X. Polym. Chem., 2017, 8(5):860.
[76] McCloskey B D, Park H B, Ju H, Rowe B W, Miller D J, Chun B J, Kin K, Freeman B D. Polymer, 2010, 51(15):3472.
[77] Kasemset S, Lee A, Miller D J, Freeman B D, Sharma M M.J.Membrane Sci., 2013, 425/426:208.
[78] Zhu L J, Liu F, Yu X M, Gao A L, Xue L X. J. Membrane Sci., 2015, 475:469.
[79] Ulbricht M, Matuschewski H, Oechel A, Hicke H. J. Membrane Sci., 1996, 115(1):31.
[80] Pieracci J, Wood D W, Crivello J V, Belfort G. Chem. Mater., 2000, 12(8):2123.
[81] Pieracci J, Crivello J V, Belfort G. Chem. Mater., 2002, 14(1):256.
[82] Wavhal D S, Fisher E R. J. Membrane Sci., 2002, 209(1):255.
[83] Liu Z M, Xu Z K, Wan L S, Wu J, Ulbricht M. J. Membrane Sci., 2005, 249(1/2):21.
[84] Mok S, Worsfold D J, Fouda A, Matsuura T. J. Appl. Polym. Sci., 1994, 51(1):193.
[85] Kang J S, Shim J K, Huh H, Lee Y M. Langmuir, 2001, 17(14):4352.
[86] He K, Duan H R, Chen G Y, Liu X K, Yang W S, Wang D Y. ACS Nano, 2015, 9(9):9188.
[87] Krause J E, Brault N D, Li Y T, Xue H, Zhou Y B, Jiang S Y. Macromolecules, 2011, 44(23):9213.
[88] Zhu J Y, Tian M M, Hou J W, Wang J, Lin J Y, Zhang Y T, Liu J D, van der Bruggen B. J. Mater. Chem. A, 2016, 4(5):1980.
[89] Zheng J F, Li M, Yao Y J, Zhang X, Wang L J. J. Mater. Chem. A, 2017, 5(26):13730.
[90] 徐和德(Xu H D). 离子交换与吸附(Ion. Exchange. Adsorpt.), 1995, (05):460.
[91] 徐和德(Xu H D), 李国明(Li G M), 陈文森(Chen W S).应用化学(Chin. J. Appl. Chem.), 1993, (05):22.
[92] Chandrasekara N P G N, Pashley R M. Desalination, 2015, 357:131.
[93] Chan W F, Chen H Y, Surapathi A, Taylor M G, Shao X H, Marand E, Johnson J K. ACS Nano, 2013, 7(6):5308.
[94] Liu T Y, Yuan H G, Li Q, Tang Y H, Zhang Q, Qian W Z, van der Bruggen B, Wang X L. ACS Nano, 2015, 9(7):7488.
[95] Zhang Z, Zhang M, Chen S F, Horbetta T A, Ratner B D, Jiang S Y. Biomaterials, 2008, 29(32):4285.
[96] Shih Y J, Chang Y. Langmuir, 2010, 26(22):17286.
[97] Shih Y J, Chang Y, Quemener D, Yang H S, Jhong J F, Ho F M, Higuchi A, Chang Y. Langmuir, 2014, 30(22):6489.
[98] Yu B Y, Zheng J, Chang Y, Sin M C, Chang C H, Higuchi A, Sun Y M. Langmuir, 2014, 30(25):7502.
[99] Zhang L, Xue H, Gao C L, Carr L, Wang J N, Chu B C, Jiang S Y. Biomaterials, 2010, 31(25):6582.
[100] Zhu Y H, Sundaram H S, Liu S J, Zhang L, Xu X W, Yu Q M, Xu J Q, Jiang S Y. Biomacromolecules, 2014, 15(5):1845.
[101] Yuan J J, Armes S P, Takabayashi Y, Prassides K, Leite C A P, Galembeck F, Lewis A L. Langmuir, 2006, 22(26):10989.
[102] Luongo G, Campagnolo P, Perez J E, Kosel J, Georgiou T K, Regoutz A, Payne D J, Stevens M M, Ryan M P, Porter A E, Dunlop I E. ACS Appl. Mater. Inter., 2017, 9(46):40059.
[103] Zhai S Y, Ma Y H, Chen Y Y, Li D, Cao J, Liu Y J, Cai M T, Xie X X, Chen Y W, Luo X L. Polym. Chem., 2014, 5(4):1285.
[104] Wang H B, Xu F M, Wang Y, Liu X S, Jin Q, Ji J. Polym. Chem., 2013, 4(10):3012.
[105] Liu G Y, Jin Q, Liu X S, Lv L P, Chen C J, Ji J. Soft Matter, 2011, 7(2):662.
[106] Chen Y J, Li Z H, Wang H B, Wang Y, Han H J, Jin Q, Ji J. ACS Appl. Mater. Inter., 2016, 8(11):6852.
[107] Chen X J, Mcrae S, Parelkar S, Emrick T. Bioconjugate Chem., 2009, 20(12):2331.
[108] Wang D L, Zhao T Y, Zhu X Y, Yan D Y, Wang W W. Chem. Soc. Rev., 2015, 44(12):4023.
[109] Zheng Y C, Li S P, Weng Z L, Gao C. Chem. Soc. Rev., 2015, 44(12):4091.
[110] Li X J, Qian Y F, Liu T, Hu X L, Zhang G Y, You Y Z, Liu S Y. Biomaterials, 2011, 32(27):6595.
[111] Xu W J, Siddiqui I A, Nihal M, Pilla S, Rosenthal K, Mukhtar H, Gong S. Biomaterials, 2013, 34(21):5244.
[112] Chen G J, Jaskula Sztul R, Harrison A, Dammalapati A, Xu W J, Cheng Y Q, Chen H, Gong S Q. Biomaterials, 2016, 97:22.
[113] Torchilin V P. J. Control. Release, 2001, 73(2):137.
[114] Chen H T, Kim S, He W, Wang H F, Low P S, Park K, Cheng J X. Langmuir, 2008, 24(10):5213.
[115] Poon Z, Lee J A, Huang S, Prevost R J, Hammond P T. Nanomed-Nanotechnol., 2011, 7(2):201.
[116] Kim S W, Shi Y Z, Kim J Y, Park K, Cheng J X. Expert Opin. Drug Del., 2009, 7(1):49.
[117] Sun P, Chen D, Deng H P, Wang N, Huang P, Jin X, Zhu X Y. Bioconjugate Chem., 2017, 28(5):1470.
[118] Sugihara S, Blanazs A, Armes S P, Ryan A J, Lewis A L. J. Am. Chem. Soc., 2011, 133(39):15707.
[119] Warren N J, Armes S P. J. Am. Chem. Soc., 2014, 136(29):10174.
[120] Doncom K E B, Warren N J, Armes S P. Polym. Chem., 2015, 6(41):7264.
[121] Cho E C, Xie J W, Wurm P A, Xia Y N. Nano Lett., 2009, 9(3):1080.
[122] Zhang Z, Chen S F, Jiang S Y. Biomacromolecules, 2006, 7(12):3311.
[123] Sun F, Wu K, Hung H C, Zhang P, Che X R, Smith J, Lin X J, Li B W, Jain P, Yu Q M, Jiang S Y. Anal. Chem., 2017, 89(20):10999.
[124] Padlan E A, Davies D R, Rudikoff S, Potter M. Immunochemistry, 1976, 13(11):945.
[125] Volanakis J E, Wirtz K W. Nature, 1979, 281(5727):155.
[126] Matyjaszewski K, Tsarevsky N V. Nat. Chem., 2009, 1(4):276.
[127] Lutz J, Ouchi M, Liu D R, Sawamoto M. Science, 2013, 341(6146):1238149.
[128] Kitayama Y, Takeuchi T. Anal. Chem., 2014, 86(11):5587.
[129] Wiarachai O, Vilaivan T, Iwasaki Y, Hoven V P. Langmuir, 2016, 32(4):1184.
[130] Sun J T, Yu Z Q, Hong C Y, Pan C Y. Macromol. Rapid Comm., 2012, 33(9):811.
[131] Xu J T, Jung K, Atme A, Shanmugam S, Boyer C. J. Am. Chem. Soc., 2014, 136(14):5508.
[132] Xu J T, Fu C K, Shanmugam S, Hawker C J, Moad G, Boyer C. Angew. Chem. Int. Ed., 2017, 56(29):8376.
[133] Ng G, Yeow J, Xu J T, Boyer C. Polym. Chem., 2017, 8(18):2841.
[134] Liu Z F, Lv Y, An Z S. Angew. Chem. Int. Ed., 2017, 56(44):13852.
[135] Barner L, Quinn J F, Barner-Kowollik C, Vana P, Davis T P. Eur. Polym. J., 2003, 39(3):449.
[136] McKenzie T G, Colombo E, Fu Q, Ashokkumar M, Qiao G G. Angew. Chem. Int. Ed., 2017, 56(40):12302.
[137] Matyjaszewski K, Dong H C, Jakubowski W, Pietrasik J, Kusumo A. Langmuir, 2007, 23(8):4528.
[138] Wang Y, Fantin M, Park S, Gottlieb E, Fu L Y, Matyjaszewski K. Macromolecules, 2017, 50(20):7872.
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