2，5-呋喃二甲酸（2，5-FDCA）是基于可再生资源的二酸，来源广泛，可由果糖和半乳糖制得。近年来以2，5-呋喃二甲酸为起始原料合成聚合物的研究引起了人们的广泛关注。本文对基于可再生资源含呋喃环均聚酯及共聚酯的合成、结构和性能等方面的研究作了综述，着重阐述了以2，5-呋喃二甲酸及其衍生物为起始原料制备聚酯的新进展，并讨论了基于可再生资源含呋喃聚酯的应用及发展前景。
2,5-Furandicarboxylic acid (FDCA) is a diacid based on renewable resources and can be synthesized from fructose and galactose. Recently, polymers synthesized from FDCA have attracted more and more attention. The recent studies of synthesis, structures and properties of homopolyesters and copolyesters containing furan rings based on renewable resources, especially for the polyesters synthesized from 2,5-furandicarboxylic acid and its derivatives are summurized. The application and development of these polyesters are also discussed.
Contents
1 Introduction
2 Synthesis methods,structure and properties of polyesters containing furan ring
2.1 Synthesis methods of polyesters containing furan ring
2.2 Structures and properties of homopolyesters containing furan ring
2.3 Structures and properties of copolyesters containing furan ring
3 Composite materials and the 3D printing material containing furan ring-based polyesters
4 Conclusion
[1] Gandini A, Lacerda T M, Carvalho A J, Trovatti E. Chemical Reviews, 2016, 116:1637.
[2] Wu J, Eduard P, Jasinskawalc L, Rozanski A, Noordover B A J, van Es D S, Koning C E. Macromolecules, 2013, 46:384.
[3] Japu C, Ilarduya A M D, Alla A, Garcíamartín M G, Galbis J A, Muñozguerra S. Polymer Chemistry, 2013, 4:3524.
[4] Lavilla C, Ilarduya A M D, Alla A, Muñoz-Guerra S. Polymer Chemistry, 2012, 4:282.
[5] Japu C, Ilarduya A M D, Alla A, García-Martín M G, Galbis J A, Muñoz-Guerra S. Macromolecular Chemistry & Physics, 2014, 215:2048.
[6] Zakharova E, Alla A, Ilarduya A M D, Muñoz-Guerra S. RSC Advances, 2015, 5:46395.
[7] Japu C, Martínez D I A, Alla A, Jiang Y, Loos K, Muñoz-Guerra S. Biomacromolecules, 2015, 16:868.
[8] Wei Z, Long C, Yu Z. Polymer, 2009, 50:1311.
[9] Liu L F, Yu J Y, Cheng L D, Qu W W. Composites Part A Applied Science & Manufacturing, 2009, 40:669.
[10] Chen G Q. Chemical Society Reviews, 2009, 38:2434.
[11] Gonis G, Amstutz E D. Journal of Organic Chemistry, 1962, 27:2946.
[12] Yu Z L, Zhou J D, Cao F, Wen B B, Zhu X, Wei P. Journal of Applied Polymer Science, 2013, 130:1415.
[13] Schrock A K, Hamilton H S C, Johnson N D, Rosario C D, Thompson B D, Ulrich K, Coggio W D. Polymer, 2016, 101:233.
[14] And M A C, Grinstaff M W. Macromolecules, 2016, 39:609.
[15] Wu L B, Mincheva R, Xu Y T, Raquez J M, Dubois P. Biomacromolecules, 2012, 13:2973.
[16] Bakr M A, Mahmud A, Sarker M, Islam M A. Journal of Polymer Materials, 2015, 32:1.
[17] Wei Z Y, Zhou C, Yu Y, Li Y. RSC Advances, 2015, 5:42777.
[18] Lee J, Min K J, Oh H, Sohn Y S, Jeong B. Polymer, 2006, 47:3760.
[19] Kwiecień M, Kwiecień I, Radecka I, Kannappan V, Morris M R, Adamus G. RSC Advances, 2017, 7:20469.
[20] Tang J C, Zhang Z J, Song Z F, Chen L R, Hou X, Yao K D. European Polymer Journal, 2006, 42:3360.
[21] Tsanaktsis V, Papageorgiou D G, Exarhopoulos S, Bikiaris D N, Papageorgiou G Z. Crystal Growth & Design, 2015, 15:5505.
[22] Vannini M, Marchese P, Celli A, Lorenzetti C. Green Chemistry, 2015, 17:4162.
[23] Szymczyk A. European Polymer Journal, 2009, 45:2653.
[24] Wang Q M. Polymer Bulletin, 2013, 15:129.
[25] Ma J P, Pang Y, Wang M, Xu J, Ma H, Nie X. Journal of Materials Chemistry, 2012, 22:3457.
[26] Cristobal J L V, Mendoza G A P. Journal of Applied Polymer Science, 2010, 43:1605.
[27] Yoon W J, Oh K S, Koo J M, Kim J R, Lee K J, Im S S. Macromolecules, 2013, 46:2930.
[28] Park H S, Gong M S, Knowles J C. Journal of Biomaterials Applications, 2012, 27:99.
[29] Risti? I S, Vuki? N, Caki? S, Simendi? V, Risti? O, Budinski-Simendi? J. Journal of Polymers & the Environment, 2012, 20:519.
[30] Lee J, Lee S, Yoon D, Yoon W J, Im S S, Moon B, Oh H B. Rapid Communications in Mass Spectrometry Rcm, 2013, 27:1913.
[31] Yoon W J, Hwang S Y, Koo J M, Lee Y J, Sang U L, Im S S. Macromolecules, 2013, 46:7219.
[32] Zhang F C, Wang Q X, Wang L P, Bai Y P. Journal of Applied Polymer Science, 2017:45444.
[33] Lv A, Li Z L, Du F S, Li Z C. Macromolecules, 2014, 47:7707.
[34] Wu Y M, Xie Q W, Gao C H, Wang T, Wang C X. Polymer Engineering & Science, 2014, 54:2515.
[35] Shivarkar A B, Gaykar D V, Jain R K. Progress in Organic Coatings, 2015, 89:75.
[36] Takagaki A, Nishimura S, Ebitani K. Catalysis Surveys from Asia, 2012, 16(3):164.
[37] Jong E, Higson A, Walsh P, Wellisch M. Biofuels Bioproducts & Biorefining, 2012, 6(6):606.
[38] Burgess S K, Kriegel R M, Koros W J. Macromolecules, 2014, 47:1383.
[39] Wu J P, Xie H Z, Wu L B, Li B G, Dubois P. RSC Advances, 2017, 7:13877.
[40] Tsanaktsis V, Bikiaris D N, Guigo N, Exarhopoulos S, Papageorgiou D G, Sbirrazzuoli N, Papageorgiou G Z. RSC Advances, 2015, 5:74592.
[41] Martino L, Niknam V, Guigo N, Berkel J G V, Sbirrazzuoli N. RSC Advances, 2016, 6:59800.
[42] Deng J, Liu X Q, Li C, Jiang Y H, Zhu J. RSC Advances, 2015, 5:15930.
[43] Sousa A F, Matos M, Freire C S R, Silvestre A J D, Coelho J F J. Polymer, 2013, 54:513.
[44] Papageorgiou G Z, Papageorgiou D G, Tsanaktsis V, Bikiaris D N. Polymer, 2015, 62:28.
[45] Morales-Huerta J C, Ilarduya A M D, Muñoz-Guerra S. Polymer, 2016, 87:148.
[46] Lotti N, Munari A, Gigli M, Gazzano M, Tsanaktsis V, Bikiaris D N, Papageorgiou G Z. Polymer, 2016, 103:288.
[47] Kwiatkowska M, Kowalczyk I, Kwiatkowski K, Szymczyk A, Ros?aniec Z. Polymer, 2016, 99:503.
[48] Burgess S K, Karvan O, Johnson J R, Kriegel R M, Koros W J. Polymer, 2014, 55:4748.
[49] Papageorgiou G Z, Tsanaktsis V, Bikiaris D N. Physical Chemistry Chemical Physics Pccp, 2014, 16:7946.
[50] Van Berkel J G, Guigo N, Kolstad J J, Sipos L, Wang B, Dam M A, Sbirrazzuoli N. Macromolecular Materials & Engineering, 2015, 300:466.
[51] Codou A, Guigo N, Van Berkel J, De Jong E, Sbirrazzuoli N. Macromolecular Chemistry & Physics, 2015, 215:2065.
[52] Su Y, Brown H M, Huang X W, Zhou X D, Amonette J E, Zhang Z C. Applied Catalysis A-General, 2009, 361:117.
[53] Zhou L L, He Y M, Ma Z W, Liang R J, Wu T H, Wu Y. Carbohydrate Polymers, 2015, 117:694.
[54] Zhao S, Cheng M X, Li J Z, Tian J, Wang X H. Chemical Communications, 2011, 47:2176.
[55] Li H, Zhang Q Y, Liu X F, Chang F, Hu D Y, Zhang Y P, Xue W, Yang S. RSC Advances, 2013, 3:3648.
[56] Banerjee A, Dick G R, Yoshino T, Kanan M W. Nature, 2016, 531:215.
[57] Cawse J L, Stanford J L, Still R H. Macromolecular Chemistry & Physics, 1984, 185:709.
[58] Quillerou J, Belgacem M N, Gandini A, Rivero J, Roux G. Polymer Bulletin, 1989, 21:555.
[59] Belgacem M N, Quillerou J, Gandini A, Rivero J, Roux G. European Polymer Journal, 1989, 25:1125.
[60] Belgacem M N, Quillerou J, Gandini A. European Polymer Journal, 1993, 29:1217.
[61] Neumann C N, Bulach W D, Rehahn M, Klein R. Macromolecular Rapid Communications, 2011, 32:1373.
[62] Liu X X, Du P F, Li L, Zhen Z, Wang X L, Joncheray T, Zhang Y F. Polymer Bulletin, 2013, 70:2319.
[63] Mignard N, Okhay N, Jegat C, Taha M. Journal of Polymer Research, 2013, 20:233.
[64] Mitiakoudis A, Gandini A. Macromolecules, 1991, 24:649.
[65] Gharbi S, Gandini A. Acta Polymerica, 1999, 50:293.
[66] Liu Y L, Chen Y W. Macromolecular Chemistry & Physics, 2010, 208:224.
[67] Fehrenbacher U, Grosshardt O, Kowollik K, Tübke B, Dingenouts N, Wilhelm M. Chemie Ingenieur Technik-CIT, 2010, 81:1829.
[68] Galan J F, Tang C N, Chakrabarty S, Liu Z, Moyna G, Pophristic V. Physical Chemistry Chemical Physics Pccp, 2013, 15:11883.
[69] Cao M, Zhang C H, He B, Huang M J, Jiang S J. Macromolecular Research, 2017, 7:722.
[70] Jiang Y, Maniar D, Woortman A, Loos K. RSC Advances, 2016, 6:67941.
[71] Jiang Y, Maniar D, Woortman A J J, Loos K. Biomacromolecules, 2015, 16:3674.
[72] Endah Y K, Han S H, Kim J H, Kim N K, Kim W N, Lee H S, Lee H. Journal of Applied Polymer Science, 2016, 133:43391.
[73] Wilsens C H R M, Deshmukh Y S, Noordover B A J, Rastogi S. Macromolecules, 2014, 47:6196.
[74] Wang J G, Liu X Q, Zhang Y J, Liu F, Zhu J. Polymer, 2016, 103:1.
[75] Wu B S, Xu Y T, Bu Z Y, Wu L B, Li B G, Dubois P. Polymer, 2014, 55:3648.
[76] 李静涛(Li J T). 河南化工(Henan Chemical Industry), 2013, 30(5):9.
[77] Gomes M, Gandini A, Silvestre A J D, Reis B. Journal of Polymer Science Part A Polymer Chemistry, 2011, 49:3759.
[78] Moore J A, Kelly J E. Macromolecules, 1978, 11:568.
[79] Sousa A F, Coelho J F J, Silvestre A J D. Polymer, 2016, 98:129.
[80] Morales-huerta J C, Martínez de Ilarduya A, Muñoz-Guerra S. ACS Sustainable Chemistry & Engineering, 2016, 4, 4965.
[81] O'hagan D, Zaidi N A. Polymer, 1994, 35:3576.
[82] Knani D, Gutman A L, Kohn D H. Journal of Polymer Science Part A Polymer Chemistry, 1993, 31:1221.
[83] Uyama H, Suda S, Kikuchi H, Kobayashi S. Chemistry Letters, 1997, 11:1109.
[84] Uyama H, Kobayashi S. Chemistry Letters, 1994, 23:1687.
[85] Uyama H, Inada K, Kobayashi S. Chemistry Letters, 1998, 1998:1285.
[86] Okumura S, Iwai M, Tominaga Y. Agricultural & Biological Chemistry, 1984, 48:2805.
[87] Jiang Y, Woortman A J, Go A V E, Petrovi? D M, Loos K. Biomacromolecules, 2014, 15:2482.
[88] Jiang M, Liu Q, Zhang Q, Ye C, Zhou G Y. Journal of Polymer Science Part A Polymer Chemistry, 2012, 50:1026.
[89] Thiyagarajan S, Vogelzang W, Knoop R J I, Frissen A E, Van Haveren J, Van Es D S. Green Chemistry, 2014, 16:1957.
[90] Tsanaktsis V, Terzopoulou Z, Nerantzaki M, Papageorgiou G Z, Bikiaris D N. Materials Letters, 2016, 178:64.
[91] Tsanaktsis V, Papageorgiou G Z, Bikiaris D N. Journal of Polymer Science Part A Polymer Chemistry, 2015, 53:2617.
[92] 姜敏(Jiang M), 周光远(Zhou G Y), 张强(Zhang Q), 叶冲(Ye C), 敖玉辉(Ao Y H). 应用化学(Applied Chemistry), 2012, 29:751.
[93] 姜敏(Jiang M), 刘茜(Liu Q), 李洋(Li Y), 张强(Zhang Q), 周光远(Zhou G Y). 高分子学报(Acta Polymerica Sinica), 2013, 46:24.
[94] 李连贵(Li L G), 李洋(Li Y), 叶冲(Ye C), 张强(Zhang Q), 姜敏(Jiang M), 周光远(Zhou G Y). 应用化学(Applied Chemistry), 2013, 30:661.
[95] Stoclet G, Sart G G D, Yeniad B, Vos S D, Lefebvre J M. Polymer, 2015, 72:165.
[96] Ma J P, Yu X F, Xu J, Pang Y. Polymer, 2012, 53:4145.
[97] Zhu J H, Cai J L, Xie W C, Chen P H, Gazzano M, Scandola M, Gross R A. Macromolecules, 2013, 46:796.
[98] Pan T, Deng J, Xu Q, Zuo Y, Guo Q X, Fu Y J. ChemSusChem, 2013, 6:47.
[99] Shono T, Hyono K, Hachihama Y. Journal of the Society of Chemical Industry Japan, 1960, 63:176.
[100] Gandini A, Silvestre A J D, Neto C P, Sousa A F, Gomes M. Journal of Polymer Science Part A Polymer Chemistry, 2010, 47:295.
[101] Gandini A. Macromolecules, 2008, 41:37.
[102] Gruter G M, Sipos L, Dam M A. Combinatorial Chemistry & High Throughput Screening, 2011, 10:1.
[103] Gubbels E, Jasinska-Walc L, Koning C E. Journal of Polymer Science Part A Polymer Chemistry, 2013, 51:890.
[104] Wu J, Eduard P, Thiyagarajan S, Noordover B A J, van Es D S, Koning C E. Chemsuschem, 2015, 8:67.
[105] Tsanaktsis V, Terzopoulou Z, Exarhopoulos S, Bikiaris D N, Achilias D S, Papageorgiou D G, Papageorgiou G Z. Polymer Chemistry, 2015, 6:8284.
[106] Matos M, Sousa A F, Silvestre A J D. Macromolecular Chemistry & Physics, 2016, 218:1600492.
[107] 姜敏(Jiang M), 芦婷婷(Lu T T), 姜国伟(Jiang G W), 张强(Zhang Q), 周光远(Zhou G Y). 高分子学报(Acta Polymerica Sinica), 2013, 46:1092.
[108] Jiang M, Lu T T, Zhang Q, Chen Y, Zhou G Y. Journal of Renewable Materials, 2015, 3:120.
[109] Zhou W D, Wang X W, Yang B, Xu Y, Zhang W, Zhang Y H, Ji J H. Polymer Degradation and Stability, 2013, 98:2177.
[110] Wang G Q, Jiang M, Zhang Q, Wang R, Tong X B, Xue S Y, Zhou G Y. Polymer Degradation & Stability, 2017, 143:1.
[111] Diao L C, Su K M, Li Z H, Ding C K. RSC Advances, 2016, 6:27632.
[112] Soccio M, Costa M, Lotti N, Gazzano M, Siracusa V, Salatelli E, Manaresi P, Munari A. European Polymer Journal, 2016, 81:397.
[113] Zhou W D, Zhang Y J, Xu Y, Wang P L, Gao L, Zhang W, Ji J H. Polymer Degradation & Stability, 2014, 109:21.
[114] Lomelí-Rodríguez M, Martín-Molina M, Jiménez-Pardo M, Nasim-Afzal Z, Cauët S I, Davies T E, Rivera-Toledo M, Lopez-anchez J A. Journal of Polymer Science Part A Polymer Chemistry, 2016, 54:2876.
[115] Wang G Q, Jiang M, Zhang Q, Wang R, Zhou G Y. Polymer Degradation & Stability, 2017, 144:121.
[116] Matos M, Sousa A F, Fonseca A C, Freire C S R, Coelho J F J, Silvestre A J D. Macromolecular Chemistry & Physics, 2014, 215:2175.
[117] Wang G Q, Jiang M, Zhang Q, Wang R, Zhou G Y. RSC Advances, 2017, 7:13798.
[118] Burgess S K, Wenz G B, Kriegel R M, Koros W J. Polymer, 2016, 98:305.
[119] Gubbels E, Jasinska-Walc L, Noordover B A J, Koning C E. European Polymer Journal, 2013, 49:3188.
[120] Fan C C, Pang C C, Liu X H, Ma J B, Gao H. Green Chemistry, 2016, 18, 6320.
[121] Hu Y S, Prattipati V, Mehta S, Schiraldi D A, Hiltner A, Baer E. Polymer, 2005, 46:2685.
[122] Martino L, Guigo N, Berkel J G V, Sbirrazzuoli N. Composites Part B Engineering, 2017, 110:96.
[123] Kucherov F A, Gordeev E G, Kashin A S, Ananikov V P. Angewandte Chemie International Edition, 2017, 56:15931.
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