聚酯酰胺的合成
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摘要
聚(酯酰胺)(PEA)的主链中同时具有酯键和酰胺键,兼具了聚酯(polyester)的生物降解性和相容性以及聚酰胺(polyamide)优异的机械性能,在药物控释、组织工程以及热塑性弹性体等领域应用广泛。缩合聚合是合成聚酯酰胺最初的方法,近年来开环聚合(ROP)成为制备聚酯酰胺的主要策略,本文从环状单体均聚、环状单体共聚、环状单体和线形单体共聚等方面总结了聚酯酰胺合成的研究进展。同时,介绍了基于多组分聚合反应(MCP)的新合成方法,并对聚酯酰胺材料的发展进行了探讨和展望。
Poly(ester amide)(PEA) is a class of functional polymers with both amide and ester linkages in the polymer main chains. Due to the outstanding biodegradability, biocompatibility and mechanical property, PEA has broad applications in drug delivery, tissue engineering and thermoplastic elastomer. Polycondensation is the original synthetic method to PEA. Recently, remarkable achievements have been made in synthesis of PEA via ring-opening polymerization(ROP). This review summarizes the progress in ROP of cyclic monomers, ring-opening copolymerization(ROCP) of cyclic monomers and ROCP of cyclic/linear momomers. Moreover, multicomponent polymerization(MCP) is highlighted as a novel synthetic strategy to prepare PEA. The challenge and outlook of PEA are also discussed.
Poly(ester amide)(PEA) is a class of functional polymers with both amide and ester linkages in the polymer main chains. Due to the outstanding biodegradability, biocompatibility and mechanical property, PEA has broad applications in drug delivery, tissue engineering and thermoplastic elastomer. Polycondensation is the original synthetic method to PEA. Recently, remarkable achievements have been made in synthesis of PEA via ring-opening polymerization(ROP). This review summarizes the progress in ROP of cyclic monomers, ring-opening copolymerization(ROCP) of cyclic monomers and ROCP of cyclic/linear momomers. Moreover, multicomponent polymerization(MCP) is highlighted as a novel synthetic strategy to prepare PEA. The challenge and outlook of PEA are also discussed.
引文
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[2] Nie J, Liu X, Yan Y, Zhang H. J. Mater. Chem. C, 2017, 5: 10391.
[3] Bednarek M. Prog. Polym. Sci., 2016, 58: 27.
[4] Winnacker M, Rieger B. Polym. Chem., 2016, 7: 7039.
[5] Natarajan J, Madras G, Chatterjee K. ACS Appl. Mater. Inter., 2017, 9: 28281.
[6] Carothers W H, Dorough G L, Natta F J V. J. Am. Chem. Soc., 1932, 54: 761.
[7] Dr P D. Angew. Chem. Int. Edit., 2004, 43: 1078.
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[12] Rodríguez-Galán A, Franco L, Puiggali J. Biodegradable Poly(Ester Amide)s: Synthesis and Applications. 2nd ed. NY: Nova Science, 2011. 207.
[13] Sun H, Meng F, Dias A A, Hendriks M, Feijen J, Zhong Z. Biomacromolecules, 2011, 12: 1937.
[14] Khan W, Muthupandian S, Farah S, Kumar N, Domb A J. Macromol. Biosci., 2011, 11: 1625.
[15] Hu X, Zhu N, Fang Z, Guo K. React. Chem. Eng., 2017, 2: 20.
[16] H?cker H, Keul H. Adv. Mater., 1994, 6: 21.
[17] Okada M. Adv. Polym. Sci., 1992, 102: 1.
[18] 汪羽翎(Wang Y L), 李武松(Li W S), 刘聪聪(Liu C C), 黄卫(Huang W), 颜德岳(Yan D Y), 康宏强(Kang H Q). 高分子学报(Acta polymerica Sinica), 2017, 1304.
[19] 周群华(Zhou Q H), 杨立群(Yang L Q), 张巍(Zhang W), 李淼(Li M). 中国组织工程研究(Journal of Clinical Rehabilitative Tissue Engineering Research), 2016, 20: 4524.
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[24] Shoda S, Uyama H, Kadokawa J, Kimura S, Kobayashi S. Chem. Rev., 2016, 116: 2307.
[25] Feng Y K, Knufermann J, Klee D, Hocker H. Macromol. Chem. Phys., 1999, 200: 1506.
[26] Feng Y, Lu J, Behl M, Lendlein A. Macromol. Biosci., 2010, 10: 1008.
[27] Feng Y, Klee D, Keul H, H?cker H. Macromol. Chem. Phys., 2000, 201: 2670.
[28] Fey T, Keul H, H?cker H. Macromol. Chem. Phys., 2003, 204.
[29] Fey T, Keul H, H?cker H. Macromol. Symp., 2004, 215: 307.
[30] Jakisch L, B?hme F, Komber H, Pompe G. Macromol. Rapid. Commun., 1999, 20: 256.
[31] Feng Y, Lu W, Ren X, Liu W, Guo M, Ullah I, Zhang W. Polymers, 2016, 8: 13.
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[33] Hao X, Li Q, Lv J, Yu L, Ren X, Zhang L, Feng Y, Zhang W. ACS Appl. Mater. Inter., 2015, 7: 12128.
[34] Rainbolt E A, Washington K E, Biewer M C, Stefan M C. Polym. Chem., 2015, 6: 2369.
[35] Toncheva-Moncheva N, Jerome R, Mateva R. Polym. Degrad. Stabil., 2016, 123: 170.
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[37] Chromcová D, Baslerová L, Roda J, Bro?ek J. Eur. Polym. J., 2008, 44: 1733.
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[39] 许茸(Xu R), 陈春霞(Chen C X). 化学进展(Progress in Chemistry), 2012, 24: 1519.
[40] Sanchez-Sanchez A, Basterretxea A, Mantione D, Etxeberria A, Elizetxea C, de la Calle A, García-Arrieta S, Sardon H, Mecerreyes D. J. Polym. Sci. Part A: Polym. Chem., 2016, 54: 2394.
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[42] Deshayes G, Delcourt C, Verbruggen I, Trouillet-Fonti L, Touraud F, Fleury E, Degée P, Destarac M, Willem R, Dubois P. Eur. Polym. J., 2011, 47: 98.
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[44] Yang W, Wei D, Tang M. J. Org. Chem., 2017, 82: 13043.
[45] Zhang G, Xu W, Liu J, Das D K, Yang S, Perveen S, Zhang H, Li X, Fang X. Chem. Commun., 2017, 53: 13336.
[46] 郭凯(Guo K), 弓桦(Gong H), 朱宁(Zhu N), 胡欣(Hu X), 方正(Fang Z), 王海鑫(Wang H X), 曾文波(Zeng W B). ZL201610219405.3, 2016.
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[48] 于翠萍(Yu C P), 李希(Li X), 沈之荃(Shen Z Q). 化学进展(Progress in Chemistry), 2007, 19: 136.
[49] Li X, Chen C, Wu J. Molecules, 2018, 23: 189.
[50] Mezzasalma L, Dove A P, Coulembier O. Eur. Polym. J., 2017.
[51] Basterretxea A, Gabirondo E, Sanchez-Sanchez A, Etxeberria A, Coulembier O, Mecerreyes D, Sardon H. Eur. Polym. J., 2017, 95: 650.
[52] Ottou W N, Sardon H, Mecerreyes D, Vignolle J, Taton D. Prog. Polym. Sci., 2016, 56: 64.
[53] Fernández J, Etxeberria A, Sarasua J R. Polym. Degrad. Stabil., 2015, 112: 104.
[54] Kronek J, Lustoň J, Kroneková Z, Paulovi?ová E, Farka? P, Petren?íková N, Paulovi?ová L, Janigová I. J. Mater. Sci. Mater. M, 2010, 21: 879.
[55] Li C G, Li S Q, Zhao J B, Zhang Z Y, Zhang J Y, Yang W T. Polym. Eng. Sci., 2015, 55: 763.
[56] Kempe K. Macromol. Chem. Phys., 2017, 218: 1700021.
[57] Culbertson B M. Prog. Polym. Sci., 2002, 27: 579.
[58] (a)Sano Y, Arita K, Masuda I. US 4474942, 1984.; (b)Sano Y. J. Polym. Sci. Part A: Polym. Chem., 1989, 27: 2749.
[59] Rao B S, Palanisamy A. Prog. Org. Coat., 2012, 74: 427.
[60] Masuda I, Arita K, Sano Y. US4600766, 1986.
[61] Sano Y, Arita K, Masuda I, Hirono T, Nakamura Y. J. Netw. Polym. Jpn., 1986, 7: 131.
[62] Néry L, Lefebvre H, Fradet A. Macromol. Chem. Phys., 2003, 204: 1755.
[63] Sepp?l? J V, Helminen A O, Korhonen H. Macromol. Biosci., 2004, 4: 208.
[64] Tarvainen T, Karjalainen T, Malin M, Per?korpi K, Tuominen J, Sepp?l? J, J?rvinen K. Eur. J. Pharm. Sci., 2002, 16: 323.
[65] Rabnawaz M, Wyman I, Auras R, Cheng S. Green. Chem., 2017, 19.
[66] 李红微(Li H W), 陈梦羽(Chen M Y), 赵京波(Zhao J B), 杨万泰(Yang W T). 北京化工大学学报(自然科学版)(Journal of Beijing University of Chemical Technology(Nature Science Edition)), 2011, 38: 89.
[67] Lustoň J, Kronek J, Janigová I. J. Macromol. Sci. A, 2010, 47: 716.
[68] Lustoň J, Kronek J, Kleinová A, Janigová I, Valentová H, Nedbal J. J. Polym. Sci. Part A: Polym. Chem., 2012, 50: 3936.
[69] Wilsens C H R M, Wullems N J M, Gubbels E, Yao Y, Rastogi S, Noordover B A J. Polym. Chem., 2015, 6: 2707.
[70] Wilsens C H R M, Deshmukh Y S, Noordover B A J, Rastogi S. Macromolecules, 2014, 47: 6196.
[71] ?ak?r S, Eriksson M, Martinelle M, Koning C E. Eur. Polym. J., 2016, 79: 13.
[72] Bakkali-Hassani C, Tunc D, Roos K, Planes M, Lecomte P, Carlotti S. Macromolecules, 2016, 50: 175.
[73] Qian Z, Li S, He Y, Li C, Liu X B. Polym. Degrad. Stabil., 2003, 81: 279.
[74] He Y, Du Y R, Liu X B. Adv. Mater. Res., 2011, 287/290: 1538.
[75] Solleder S C. Angew. Chem. Int. Edit., 2014, 53: 711.
[76] Badi N. Chem. Soc. Rev., 2009, 38: 3383.
[77] Ouchi M, Badi N, Lutz J F, Sawamoto M. Nat. Chem., 2011, 3: 917.
[78] Robert C, De M F, Thomas C M. Nat. Commun., 2011, 2: 586.
[79] Lutz J F. Macromol. Rapid. Commun., 2017, 38: 1700582.
[80] Urnauer S, Morys S, Levacic A K, Müller A M, Schug C, Schmohl K A, Schwenk N, Zach C, Carlsen J, Bartenstein P. Mol. Ther., 2016, 24: 1395.
[81] Li J, Stayshich R M, Meyer T Y. J. Am. Chem. Soc., 2011, 133: 6910.
[82] Chen C L, Zuckermann R N, Deyoreo J J. ACS Nano, 2016, 10: 5314.
[83] Passerini M. Gazz. Chim. Ital., 1921, 51: 126.
[84] Deng X X, Li L, Li Z L, Lv A, Du F S, Li Z C. ACS Macro. Lett., 2012, 1: 1300.
[85] Lv A, Deng X X, Li L, Li Z L, Wang Y Z, Du F S, Li Z C. Polym. Chem., 2013, 4: 3659.
[86] Kan X W, Deng X X, Du F S, Li Z C. Macromol. Chem. Phys., 2014, 215: 2221.
[87] Li L, Deng X X, Li Z L, Du F S, Li Z C. Macromolecules, 2014, 47: 4660.
[88] Kim K S, Lee D, Song C G, Kang P M. Nanomedicine, 2015, 10: 2709.
[89] Tapeinos C, Pandit A. Adv. Mater., 2016, 28: 5553.
[90] Cui Y, Zhang M, Du F S, Li Z C. ACS Macro. Lett., 2016, 6: 11.
[91] Kamaly N, Yameen B, Wu J, Farokhzad O C. Chem. Rev., 2016, 116: 2602.
[92] Zhang Y, Yin Q, Yin L, Ma L, Tang L, Cheng P D J. Angew. Chem. Int. Edit., 2013, 125: 6563.