摘要
随着环境保护和化石资源问题的日益严峻,开发基于可再生生物质资源的生物基高分子材料,成为未来的发展趋势。作为最具有价值的生物基平台化合物之一,呋喃二甲酸及其衍生物可用于制造精细化学品和高分子材料。近年来,通过熔融聚合、溶液聚合、界面缩聚和固相缩聚等方法,将呋喃二甲酸及其衍生物与二元胺反应,制备出不同结构的生物基聚酰胺的均聚物和共聚物。本文从单体、聚合方法、聚合物结构和性能等方面,对含呋喃环生物基聚酰胺的合成作一总结,同时对这一领域的前景和挑战进行了探讨。
As the increasing concerns about the environmental protection and fossil resource issues, it is important to develop biobased polymer materials from renewable biomass resources. As one of the most valuable biogenic platform compounds, furandicarboxylic acid and derivatives, have attracted much attention in synthesis of fine chemicals and biobased materials. In recent years, varied biobased polyamide homo-and copolymers have been successfully prepared via polycondensations between furandicarboxylic acid and derivative and diamines, including melt polymerization, solution polymerization, interfacial polycondensation, and solid phase polycondensation. Herein, recent progress in synthesis of renewable furan-containing polyamides are detail introduced. Polyamides with different structures present favorable thermal properties and mechanical performance. In the meantime, varied measures have been taken to improve the molecular weight, yield, catalytic efficiency, structural diversity, etc. Moreover, the challenges and modifications of biobased furan-containing polyamides for further industrial applications are discussed and prospected.
引文
[1] Wang H C, Grolman J M, Rizvi A, Hisao G S, Rienstra C M, Zimmerman S C. ACS Macro Lett., 2017, 6: 321.
[2] Moran C S, Barthelon A, Pearsall A, Mittal V, Dorgan J R. J. Appl. Polym. Sci., 2016, 133: 43626.
[3] Winnacker M, Sag J. Chem. Commun., 2018, 54: 841.
[4] Winnacker M, Sag J, Tischner A, Rieger, B. Macromol. Rapid Comm., 2017, 38: 9.
[5] Zhu Y Q, Romain C, Williams C K. Nature, 2016, 540: 354.
[6] 孙绍晖(Sun S H), 孙培勤(Sun P Q), 马国杰(Ma G J), 衡明星(Heng M X), 陈俊武(Chen J W). 化学进展(Progress in Chemistry), 2010, 22: 1844.
[7] 杨越(Yang Y), 刘琪英(Liu Q Y), 蔡炽柳(Cai Z L), 谈金(Tan J), 王铁军(Wang T J), 马隆龙(Ma L L). 化学进展(Progress in Chemistry), 2016, 28: 363.
[8] Davis S E, Zope B N, Davis R J. Green Chem., 2012, 14: 143.
[9] 刘浪(Liu L), 杨顺利(Yang S L), 李鸿波(Li H B), 陈凯(Chen K), 吴毅(Wu Y), 马昌鹏(Ma C P), 张永岗(Zhang Y G), 杨俊卿(Yang J Q). 精细化工(Fine Chemicals), 2011, 28: 410.
[10] 余作龙(Yu Z L). Doctoral Dissertation of Nanjing Tech University(南京工业大学博士学位论文), 2013.
[11] 李伟杰(Li W J), 陆豫(Lu Y). 化学试剂(Chemical Reagents), 2006, 28: 309.
[12] Koopman F, Wierckx N, de Winde J H, Ruijssenaars H. Biores. Technol., 2010, 101: 6291.
[13] van Deurzen M P J, van Rantwijk F, Sheldon R A. J. Carbohyd Chem., 1997, 16: 299.
[14] Sousa A F, Vilela C, Fonseca A C, Matos M, Freire C S R, Gruter G J M, Coelho J F J, Silvestre A J D. Polym. Chem., 2015, 6: 5961.
[15] Wu L B, Mincheva R, Xu Y T, Raquez J M, Dubois P. Biomacromolecules, 2012, 13: 2973.
[16] Gubbels E, Jasinska-Walc L, Koning C E. J. Polym. Sci, Part A: Polym. Chem., 2013, 51: 890.
[17] Jiang M, Liu Q, Zhang Q, Ye C, Zhou G Y. J. Polym. Sci, Part A: Polym. Chem., 2012, 50: 1026.
[18] Ma J P, Pang Y, Wang M, Xu J, Ma H, Nie X. J. Mater. Chem., 2012, 22: 3457.
[19] 周佳栋(Zhou J D), 曹飞(Cao F), 余作龙(Yu Z L), 文斌斌(Wen B B), 崔莉燕(Cui L Y), 汤智群(Tang Z Q), 黄婷(Huang T), 韦萍(Wei P). 高分子学报(Acta Polymerica Sinica), 2016, 1: 13.
[20] Zhou W D, Zhang Y J, Xu Y, Wang P L, Gao L, Zhang W, Ji J H. Polym. Degred. STab., 2014, 109: 21.
[21] Werpy T A. Top Value Added Chemicals From Biomass: I. Results of Screening for Potential Candidates from Sugars and Synthesis Gas. Denton: Synthetic Fuels, 2004. 26.
[22] Hopff V H, Krieger A. Die Makromol. Chem., 1961, 47: 93.
[23] Hopff H, Krieger A. Helv. Chim. Acta, 1961, 44: 1058.
[24] Heertjes P M, Kok G J. Delft Prog. Rep.,Ser. A, 1974, 1: 59
[25] Salamone. Concise Polymeric Materials Encyclopedia,CRC Press, Boca Raton, 1999, 1: 6325.
[26] Ogata N, Shimamura K. Polym. J., 1975, 7: 72.
[27] Russo M. Kunststoffe, 1975, 65: 346.
[28] Moore J A, Bunting W W. Adv. Polym. Syn., 1985, 31: 51.
[29] Mitiakoudis A, Gandini A. Macromolecules, 1991, 24: 830.
[30] Mitiakoudis A, Gandini A, Cheradame H. Polym. Commun., 1985, 26: 246.
[31] Benecke H P, Kawczak A W, Garbark D B. US 20080207847, 2008.
[32] Benecke H P, Kawczak A W, Garbark D B. US20100280186, 2010.
[33] Fehrenbacher U, Grosshardt O, Kowollik K, Tübke B, Dingenouts N and Wilhelm M. Chem. Ing. Tech., 2009, 81: 1829.
[34] Smith D D, Flores J, Aberson R, Dam M A, Duursma A, Gruter G J M. EP3060598 A1, 2016.
[35] Duursma A, Aberson R, Smith D D, Flores J, DAM M A, Gruter G J M. WO2015060718, 2015.
[36] Yeh I C, Rinderspacher B C, Andzelm J W, Cureton L S T, Scala J L. Polymer, 2014, 55: 166.
[37] Jiang Y, Maniar D, Woortman A J, Alberda G O, Loos K. Biomacromolecules, 2015, 16: 3674.
[38] Jiang Y, Maniar D, Woortman A, Loos K. RSC Adv., 2016, 6: 67941.
[39] 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). CN 106191145, 2016.
[40] 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). CN 106011192, 2016.
[41] Luo K, Wang Y, Yu J, Hu Z. RSC Adv., 2016, 6: 87013.
[42] Cureton L S T, Napadensky E, Annunziato C, Scala J J L. J. Appl. Polym. Sci., 2017, 134: 45514.
[43] Cooper S J, Atkins E D T, Hill M J. Macromolecules, 1998, 31: 8947.
[44] 孙学科(Sun X K), 高红军(Gao H J), 麦堪成(Mai K C), 张传辉(Zhang C H), 曹民(Cao M). 工程塑料应用(Engineering Plastics Application), 2017, 45: 1.
[45] Endah Y K, Han S H, Kim J H, Kim N, Kim W N, Lee H S, Lee H. J. Appl. Polym. Sci., 2016, 133: 43391.