Biobased polyesters and other polymers from 2,5-furandicarboxylic acid: A tribute to furan excellency

Polymer Chemistry

Volumn 6, Issue 33, 2015, Pages 5961-5983

  Sousa, Andreia F ^a,b   Vilela, Carla ^a   Fonseca, Ana C ^b   Matos, Marina ^a   Freire, Carmen S R ^a   Gruter, Gert Jan M ^c   Coelho, Jorge F J ^b   Silvestre, Armando J D ^a  

^a UNIVERSITY OF AVEIRO   (Portugal)

^b UNIVERSITY OF COIMBRA   (Portugal)

^c Avantium Chemicals BV   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

BIODEGRADABLE POLYMERS; BIODEGRADATION; MONOMERS; PACKAGING MATERIALS; PATENTS AND INVENTIONS; POLYESTERS; SUSTAINABLE DEVELOPMENT; TEXTILES;

2 ,5-FURANDICARBOXYLIC ACIDS; BIOBASED POLYESTERS; ENVIRONMENTAL ISSUES; INNOVATIVE MATERIALS; LIQUID CRYSTALLINE PROPERTIES; MONOMER SYNTHESIS; SYNTHETIC APPROACH; TEREPHTHALIC ACIDS;

POLYMERS;

EID: 84939167511     PISSN: 17599954     EISSN: 17599962     Source Type: Journal    
DOI: 10.1039/c5py00686d     Document Type: Review

References (165)

1. A. J. Ragauskas C. K. Williams B. H. Davison G. Britovsek J. Cairney C. A. Eckert W. J. Frederick Jr. J. P. Hallett D. J. Leak C. L. Liotta et al., The Path Forward for Biofuels and Biomaterials Science 2006 311 484 489
2. BioPreferred-Directives for the mandatory purchasing of biobased products http://www.biopreferred.gov/BioPreferred/faces/pages/AboutBioPreferred.xhtml
3. Industrial Sustainability-European Commission http://ec.europa.eu/growth/industry/sustainability/index-en.htm
4. A. Gandini Furans in polymer chemistry Prog. Polym. Sci. 1997 22 1203 1379
5. C. Vilela A. F. Sousa A. C. Fonseca A. C. Serra J. F. J. Coelho C. S. R. Freire A. J. D. Silvestre The quest for sustainable polyesters-insights into the future Polym. Chem. 2014 5 3119
6. A. Gandini The irruption of polymers from renewable resources on the scene of macromolecular science and technology Green Chem. 2011 13 1061 1083
7. A. Gandini A. J. D. Silvestre C. Pascoal Neto A. F. Sousa M. Gomes The furan counterpart of poly (ethylene terephthalate): An alternative material based on renewable resources J. Polym. Sci., Part A: Polym. Chem. 2009 5 295 298
8. PEF: game-changing plastic http://avantium.com/yxy/products-applications/fdca/applications.html
9. M. Gomes A. Gandini A. J. D. Silvestre B. Reis Synthesis and characterization of poly(2,5-furan dicarboxylate)s based on a variety of diols J. Polym. Sci., Part A: Polym. Chem. 2011 49 3759 3768
10. A. Gandini D. Coelho M. Gomes B. Reis A. Silvestre Materials from renewable resources based on furan monomers and furan chemistry: work in progress J. Mater. Chem. 2009 19 8656
11. M. Jiang Q. Liu Q. Zhang C. Ye G. Zhou A series of furan-aromatic poyesters synthesized via direct esterification method based on renewable resources J. Polym. Sci., Part A: Polym. Chem. 2012 50 1026 1036
12. R. J. I. Knoop W. Vogelzang J. van Haveren D. S. van Es High molecular weight poly(ethylene-2,5-furanoate); critical aspects in synthesis and mechanical property determination J. Polym. Sci., Part A: Polym. Chem. 2013 51 4191 4199
13. S. K. Burgess J. E. Leisen B. E. Kraftschik C. R. Mubarak R. M. Kriegel W. J. Koros Chain Mobility, Thermal, and Mechanical Properties of Poly(ethylene furanoate) Compared to Poly(ethylene terephthalate) Macromolecules 2014 47 1383 1391
14. E. de Jong, M. A. Dam, L. Sipos and G.-J. M. Gruter, Furandicarboxylic acid (FDCA), a versatile building block for a very interesting class of polyesters, in Biobased Monomers, Polymers, and Materials, ed., P. B. Smith, and, R. A. Gross, ACS Symposium Series, American Chemical Society, Washington, 2012, vol. 1105, pp. 1-13
15. C. Saywell, S. Mai, R. C. Capelas, N. J. C. Legramanti and J. C. N. Legramanti, Process for the production of poly (ethylene 2,5-furandicarboxylate) from 2,5-furandicarboxylic acid and use thereof, polyester compound and blends thereof, WO2013097013A1, 2013
16. A. Gandini A. J. D. Silvestre C. P. Neto A. F. Sousa M. Gomes The furan counterpart of poly(ethylene terephthalate): An alternative material based on renewable resources J. Polym. Sci., Part A: Polym. Chem. 2009 47 295 298
17. Y. Jiang A. J. J. Woortman G. O. R. Alberda van Ekenstein D. M. Petrović K. Loos Enzymatic synthesis of biobased polyesters using 2,5-bis(hydroxymethyl)furan as the building block Biomacromolecules 2014 15 2482 2493
18. Á. Cruz-Izquierdo L. A. M. van den Broek J. L. Serra M. J. Llama C. G. Boeriu Lipase-catalyzed synthesis of oligoesters of 2,5-furandicarboxylic acid with aliphatic diols Pure Appl. Chem. 2015 87
19. L. Sipos and M. L. Olson, Process for the depolymerization of a furandicarboxylate-containing polyester, WO2012091573A1, 2012
20. Avantium-markets & partnerships http://avantium.com/yxy/markets-partnerships.html
21. PEF and Avantium towards replacement of PET http://bioplasticsnews.com/2014/06/23/pef-and-avantium-towards-replacement-of-pet/
22. M.-B. Bouffand, A. Colloud and P. Reutenauer, Bottle, method of making the same and use of FDCA and diol monomers in such bottle, WO2014032730A1, 2014
23. A. J. J. E. Eerhart A. P. C. Faaij M. K. Patel Replacing fossil based PET with biobased PEF; process analysis, energy and GHG balance Energy Environ. Sci. 2012 5 6407
24. A. F. Sousa M. Matos C. S. R. R. Freire A. J. D. D. Silvestre J. F. J. J. Coelho New copolyesters derived from terephthalic and 2,5-furandicarboxylic acids: A step forward in the development of biobased polyesters Polymer 2013 54 513 519
25. L. Sipos, A Process for preparing a polymer having a 2,5-furandicarboxylate moiety within the polymer backbone and such (co)polymers, WO2010077133A1, 2010
26. J. Zhu J. Cai W. Xie P.-H. Chen M. Gazzano M. Scandola R. A. Gross Poly(butylene 2,5-furan dicarboxylate), a Biobased Alternative to PBT: Synthesis, Physical Properties, and Crystal Structure Macromolecules 2013 46 796 804
27. G. Z. Papageorgiou V. Tsanaktsis D. G. Papageorgiou S. Exarhopoulos M. Papageorgiou D. N. Bikiaris Evaluation of polyesters from renewable resources as alternatives to the current fossil-based polymers. Phase transitions of poly(butylene 2,5-furan-dicarboxylate) Polymer 2014 55 3846 3858
28. J. Ma X. Yu J. Xu Y. Pang Synthesis and crystallinity of poly(butylene 2,5-furandicarboxylate) Polymer 2012 53 4145 4151
29. T. Pan J. Deng Q. Xu Y. Zuo Q.-X. Guo Y. Fu Catalytic conversion of furfural into a 2,5-furandicarboxylic acid-based polyester with total carbon utilization ChemSusChem 2013 6 47 50
30. S. Thiyagarajan W. Vogelzang J. R. I. Knoop A. E. Frissen J. van Haveren D. S. van Es Biobased furandicarboxylic acids (FDCAs): effects of isomeric substitution on polyester synthesis and properties Green Chem. 2014 16 1957
31. J. Ma Y. Pang M. Wang J. Xu H. Ma X. Nie The copolymerization reactivity of diols with 2,5-furandicarboxylic acid for furan-based copolyester materials J. Mater. Chem. 2012 22 3457 3461
32. J. E. Kelly, Polyesters based on 2,5-disubstituted furans in various states reduction, Ph.D. Thesis, Rensselaer Polytechnic Institute, 1975
33. J. A. Moore J. E. Kelly Polyesters derived from furan and tetrahydrofuran nuclei Macromolecules 1978 11 568 573
34. G. Z. Papageorgiou N. Guigo V. Tsanaktsis D. G. Papageorgiou S. Exarhopoulos N. Sbirrazzuoli D. N. Bikiaris On the bio-based furanic polyesters: Synthesis and thermal behavior study of Poly(octylene furanoate) using Fast and Temperature Modulated Scanning Calorimetry Eur. Polym. J. 2015 68 115 127
35. R. Storbeck M. Ballauff Synthesis and properties of polyesters based on 2,5-furandicarboxylic acid and 1,4:3,6-dianhydrohexitols Polym. Rep. 1993 34 5003 5006
36. J. Pretula K. Kaluzynski B. Wisniewski R. Szymanski T. Loontjens S. Penczek Formation of poly(ethylene phosphates) in polycondensation of H3PO4 with ethylene glycol. Kinetic and mechanistic study J. Polym. Sci., Part A: Polym. Chem. 2008 46 830 843
37. J. Wu P. Eduard S. Thiyagarajan B. A. J. Noordover D. S. van Es C. E. Koning Semi-Aromatic Polyesters Based on a Carbohydrate-Derived Rigid Diol for Engineering Plastics ChemSusChem 2015 8 67 72
38. M. Okada K. Tachikawa K. Aoi Biodegradable polymers based on renewable resources. II. Synthesis and biodegradability of polyesters containing furan rings J. Polym. Sci., Part A: Polym. Chem. 1997 35 2729
39. G. Z. Papageorgiou D. G. Papageorgiou V. Tsanaktsis D. N. Bikiaris Synthesis of the bio-based polyester poly(propylene 2,5-furan dicarboxylate). Comparison of thermal behavior and solid state structure with its terephthalate and naphthalate homologues Polymer 2015 62 28 38
40. A. Codou N. Guigo J. van Berkel E. de Jong N. Sbirrazzuoli Non-isothermal Crystallization Kinetics of Biobased Poly(ethylene 2,5-furandicarboxylate) Synthesized via the Direct Esterification Process Macromol. Chem. Phys. 2014 215 2065 2074
41. M. Matos A. F. Sousa A. C. Fonseca C. S. R. Freire J. F. J. Coelho A. J. D. Silvestre A new generation of furanic copolyesters with enhanced degradability: poly(ethylene 2,5-furandicarboxylate)-co-poly(lactic acid) copolyesters Macromol. Chem. Phys. 2014 215 2175 2184
42. Z. Yu J. Zhou F. Cao B. Wen X. Zhu P. Wei Chemosynthesis and characterization of fully biomass-based copolymers of ethylene glycol, 2,5-furandicarboxylic acid, and succinic acid J. Appl. Polym. Sci. 2013 130 1415 1420
43. Y. Tsai C. Tai S.-J. Tsai F.-J. Tsai Shape memory effects of poly(ethylene terephthalate-co-ethylene succinate) random copolymers Eur. Polym. J. 2008 44 550 554
44. Z. Gan H. Abe Y. Doi Biodegradable Poly(ethylene succinate) (PES). 1. Crystal Growth Kinetics and Morphology Biomacromolecules 2000 1 704 712
45. C. H. R. M. Wilsens B. A. J. Noordover S. Rastogi Aromatic thermotropic polyesters based on 2,5-furandicarboxylic acid and vanillic acid Polymer 2014 55 2432 2439
46. C. H. R. M. Wilsens J. M. G. A. Verhoeven B. A. J. Noordover M. R. Hansen D. Auhl S. Rastogi Thermotropic Polyesters from 2,5-Furandicarboxylic Acid and Vanillic Acid: Synthesis, Thermal Properties, Melt Behavior, and Mechanical Performance Macromolecules 2014 47 3306 3316
47. B. K. Vriesema and F. Miniaci, Aromatic Polyesters, EP88200912.9, 1988
48. Y. Fujioka, M. Mochizuki and Y. Nagara, Liquid Crystalline Polyester, JP2010000275036, 2012
49. C. H. R. M. Wilsens, S. Rastogi, M. A. J. Veld, E. A. Klop and B. A. J. Noordover, Liquid crystalline furandicarboxylic acid based aromatic polyesters, WO2013092667A1, 2013
50. Y. Kanetaka, K. Kimura, T. Uchida and S. Yamasaki, Manufacture of polyester involves mixing and polymerizing furan-dicarboxylic acid, (formyloxy)phenyl formate-containing compound, and (formyloxy) phenyl formate containing compound, and obtaining polyester having liquid crystallinity, JP2014034611-A, 2014
51. D. Smith, J. Flores, R. Aberson, M. A. Dam, A. Duursma and G. J. M. Gruter, Polyamides containing the bio-based 2,5-furandicarboxylic acid, WO2015059047, 2014
52. A. Duursma, R. Aberson, D. Smith, J. Flores, M. A. Dam and G. J. M. Gruter, Process for preparing a furan-based polyamide, a furan-based oligomer and compositions and articles comprising the furan-based polyamide, WO2015060718, 2014
53. I.-C. Yeh B. C. Rinderspacher J. W. Andzelm L. T. Cureton J. La Scala Computational study of thermal and mechanical properties of nylons and bio-based furan polyamides Polymer 2014 55 166 174
54. U. Fehrenbacher O. Grosshardt K. Kowollik B. Tübke N. Dingenouts M. Wilhelm Synthese und Charakterisierung von Polyestern und Polyamiden auf der Basis von Furan-2,5-dicarbonsäure Chem.-Ing.-Tech. 2009 81 1829 1835
55. H. P. Benecke, A. W. Kawczak and D. B. Garbark, Furanic-modified amine-based curatives, US20100280186, 2010
56. H. P. Benecke, A. W. Kawczak and D. B. Garbark, Furanic-modified amine-based curatives, US20080207847, 2008
57. C. H. R. M. Wilsens N. J. M. Wullems E. Gubbels Y. Yao S. Rastogi B. A. J. Noordover Synthesis, kinetics, and characterization of bio-based thermosets obtained through polymerization of a 2,5-furandicarboxylic acid-based bis(2-oxazoline) with sebacic acid Polym. Chem. 2015 6 2707 2716
58. C. H. R. M. Wilsens Y. S. Deshmukh B. A. J. Noordover S. Rastogi Influence of the 2,5-Furandicarboxamide Moiety on Hydrogen Bonding in Aliphatic-Aromatic Poly(ester amide)s Macromolecules 2014 47 6196 6206
59. A. M. J. A. L. P. Zagalaz and L. M. Á. Caballero, Biodegradable polyesteretheramide, EP2628761A1, 2013
60. R. Fittig H. Heinzelman Ber. Dtsch. Chem. Ges. 1876 9 1198
61. O. Sohst B. Tollens Liebigs Ann. 1888 245 1
62. H. J. H. Fenton M. Gostling Bromomethylfurfuraldehyde J. Chem. Soc. Trans. 1899 75 423
63. W. Hoehn Iowa State Coll. J. Sci. 1936 11 66
64. B. Kamm M. Kamm Principles of biorefineries Appl. Microbiol. Biotechnol. 2004 64 137 145
65. S. Fernando S. Adhikari C. Chandrapal N. Murali Biorefineries: Current Status, Challenges, and Future Direction Energy Fuels 2006 20 1727 1737
66. T. Werpy and G. Petersen, Top Value Added Chemicals from Biomass. Volume I - Results of Screening for Potential Candidates from Sugars and Synthesis Gas, Pacific Northwest National Laboratory, 2004
67. A. Corma S. Iborra A. Velty Chemical routes for the transformation of biomass into chemicals Chem. Rev. 2007 107 2411 2502
68. J. J. Bozell G. R. Petersen Technology development for the production of biobased products from biorefinery carbohydrates - the US Department of Energy's "Top 10" revisited Green Chem. 2010 12 539 554
69. J. F. Jenck F. Agterberg M. J. Droescher Products and processes for a sustainable chemical industry: a review of achievements and prospects Green Chem. 2004 6 544
70. X. Tong Y. Ma Y. Li Biomass into chemicals: conversion of sugars to furan derivatives by catalytic processes Appl. Catal., A 2010 385 1 13
71. S. P. Teong G. Yi Y. Zhang Hydroxymethylfurfural production from bioresources: past, present and future Green Chem. 2014 16 2015
72. R.-J. Van Putten J. C. van der Waal E. de Jong C. B. Rasrendra H. J. Heeres J. G. de Vries Hydroxymethylfurfural, a versatile platform chemical made from renewable resources Chem. Rev. 2013 113 1499 1597
73. K. D. O. Vigier G. Chatel F. Jérôme Contribution of Deep Eutectic Solvents for Biomass Processing: Opportunities, Challenges, and Limitations ChemCatChem 2015 7 1250 1260
74. CEPI /Unfold The Future. The Two Team Project report http://www.unfoldthefuture.eu/uploads/report-final-for-emailing-latestv08.pdf
75. B. W. Lew, Method of producing dehydromucic acid, 1967
76. S. Siankevich G. Savoglidis Z. Fei G. Laurenczy D. T. L. Alexander N. Yan P. J. Dyson A novel platinum nanocatalyst for the oxidation of 5-Hydroxymethylfurfural into 2,5-Furandicarboxylic acid under mild conditions J. Catal. 2014 315 67 74
77. B. Siyo M. Schneider J. Radnik M. M. Pohl P. Langer N. Steinfeldt Influence of support on the aerobic oxidation of HMF into FDCA over preformed Pd nanoparticle based materials Appl. Catal., A 2014 478 107 116
78. D. J. Chadderdon L. Xin J. Qi Y. Qiu P. Krishna K. L. More W. Li Electrocatalytic oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid on supported Au and Pd bimetallic nanoparticles Green Chem. 2014 3778 3786
79. R. Sahu P. L. Dhepe Synthesis of 2,5-furandicarboxylic acid by the aerobic oxidation of 5-hydroxymethyl furfural over supported metal catalysts React. Kinet., Mech. Catal. 2014 112 173 187
80. H. Ait Rass N. Essayem M. Besson Selective aqueous phase oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid over Pt/C catalysts: influence of the base and effect of bismuth promotion Green Chem. 2013 15 2240
81. A. Villa M. Schiavoni S. Campisi G. M. Veith L. Prati Pd-modified Au on carbon as an effective and durable catalyst for the direct oxidation of HMF to 2,5-furandicarboxylic acid ChemSusChem 2013 6 609 612
82. S. Albonetti T. Pasini A. Lolli M. Blosi M. Piccinini N. Dimitratos J. a. Lopez-Sanchez D. J. Morgan A. F. Carley G. J. Hutchings et al., Selective oxidation of 5-hydroxymethyl-2-furfural over TiO 2-supported gold-copper catalysts prepared from preformed nanoparticles: Effect of Au/Cu ratio Catal. Today 2012 195 120 126
83. M. Krystof M. Pérez-Sánchez P. D. de María Lipase-mediated selective oxidation of furfural and 5-hydroxymethylfurfural ChemSusChem 2013 6 826 830
84. W. P. Dijkman D. E. Groothuis M. W. Fraaije Enzyme-catalyzed oxidation of 5-hydroxymethylfurfural to furan-2,5-dicarboxylic acid Angew. Chem., Int. Ed. 2014 53 6515 6518
85. G. Yi S. P. Teong Y. Zhang The Direct Conversion of Sugars into 2,5-Furandicarboxylic Acid in a Triphasic System ChemSusChem 2015 1151 1155
86. G. Yi S. P. Teong X. Li Y. Zhang Purification of biomass-derived 5-hydroxymethylfurfural and its catalytic conversion to 2,5-furandicarboxylic acid ChemSusChem 2014 7 2131 2135
87. L. Lai Y. Zhang The production of 5-hydroxymethylfurfural from fructose in isopropyl alcohol: a green and efficient system ChemSusChem 2011 4 1745 1748
88. N. K. Gupta S. Nishimura A. Takagaki K. Ebitani Hydrotalcite-supported gold-nanoparticle-catalyzed highly efficient base-free aqueous oxidation of 5-hydroxymethylfurfural into 2,5-furandicarboxylic acid under atmospheric oxygen pressure Green Chem. 2011 13 824
89. E.-S. Kang Y.-W. Hong D. W. Chae B. Kim B. Kim Y. J. Kim J. K. Cho Y. G. Kim From Lignocellulosic Biomass to Furans via 5-Acetoxymethylfurfural as an Alternative to 5-Hydroxymethylfurfural ChemSusChem 2015 8 1098
90. E. I. Leupold, M. Wiesner, M. Schlingmann and R. Knut, Process for the oxidation of 5-hydroxymethylfurfural, EP0356703A3, 1990
91. V. Grushin, L. E. Manzer and W. Partenheimer, Processes for preparing diacids, dialdehydes and polymers, US8748637B2, 2013
92. A. Sanborn, Oxidation of furfural compounds, WO2010132740, 2013
93. C. de D. Muñoz, P. W. Schammel, A. D. Matheus and G. J. M. Gruter, Method for the preparation of 2,5-furandicarboxylic acid and esters thereof, 2013
94. H. S. Carman Jr., J. I. Killman Jr., E. D. Crawford and J. C. Jenkins, Polyester compositions containing furandicarboxylic acid or an ester thereof and cyclohexanedimethanol, US20130095268A1, 2013
95. W. Zhou X. Wang B. Yang Y. Xu W. Zhang Y. Zhang J. Ji Synthesis, physical properties and enzymatic degradation of bio-based poly(butylene adipate-co-butylene furandicarboxylate) copolyesters Polym. Degrad. Stab. 2013 98 2177 2183
96. N. Jacquel R. Saint-Loup J.-P. Pascault A. Rousseau F. Fenouillot Bio-based alternatives in the synthesis of aliphatic-aromatic polyesters dedicated to biodegradable film applications Polymer 2015 59 234 242
97. B. Wu Y. Xu Z. Bu L. Wu B.-G. Li P. Dubois Biobased poly(butylene 2,5-furandicarboxylate) and poly(butylene adipate-co-butylene 2,5-furandicarboxylate)s: From synthesis using highly purified 2,5-furandicarboxylic acid to thermo-mechanical properties Polymer 2014 55 3648 3655
98. L. Wu R. Mincheva Y. Xu J.-M. Raquez P. Dubois High molecular weight poly(butylene succinate-co-butylene furandicarboxylate) copolyesters: from catalyzed polycondensation reaction to thermomechanical properties Biomacromolecules 2012 13 2973 2981
99. V. Tsanaktsis E. Vouvoudi G. Z. Papageorgiou D. G. Papageorgiou K. Chrissafis D. N. Bikiaris Thermal degradation kinetics and decomposition mechanism of polyesters based on 2,5-furandicarboxylic acid and low molecular weight aliphatic diols J. Anal. Appl. Pyrolysis 2014 112 369 378
100. D. I. Collias A. M. Harris V. Nagpal I. W. Cottrell M. W. Schultheis Biobased Terephthalic Acid Technologies: A Literature Review Ind. Biotechnol. 2014 10 91 105
101. S. Tavener J. Hardy N. Hart Teaching green chemistry: from lemons to lemonade bottles Green Chem. 2003 5 G46
102. J. G. N. Drewitt and J. Lincocoln
103. Y. Hachihama T. Shono K. Hyono Technol. Rep. Osaka Univ. 1958 8 475 480
104. L. G. Kazaryan F. M. Medvedeva X-Ray study of the structure of the polyester of furan-2,5-dicarboxylic acid Vysokomol. Soedin., Ser. B 1968 10
105. S. K. Burgess D. S. Mikkilineni D. B. Yu D. J. Kim C. R. Mubarak R. M. Kriegel W. J. Koros Water sorption in poly(ethylene furanoate) compared to poly(ethylene terephthalate). Part 2: Kinetic sorption Polymer 2014 55 6870 6882
106. S. K. Burgess D. S. Mikkilineni D. B. Yu D. J. Kim C. R. Mubarak R. M. Kriegel W. J. Koros Water sorption in poly(ethylene furanoate) compared to poly(ethylene terephthalate). Part 1: Equilibrium sorption Polymer 2014 55 6861 6869
107. G.-J. Gruter, European green chemistry in action: PEF, a 100% bio-based polyester: Synthesis, Properties & Sustainability, In EuroNanoForum, Riga, 2015
108. C. Muñoz de Diego, M. A. Dam and G. J. M. Gruter, Method for the preparation of 2,5-furandicarboxylic acid and for the preparation of the dialkyl ester of 2,5-furandicarboxylic acid, WO2011043661, 2011
109. G.-J. M. Gruter L. Sipos M. AdrianusDam Accelerating Research into Bio-Based FDCA-Polyesters by Using Small Scale Parallel Film Reactors Comb. Chem. High Throughput Screening 2012 15 180 188
110. G. Z. Papageorgiou V. Tsanaktsis D. N. Bikiaris Synthesis of poly(ethylene furandicarboxylate) polyester using monomers derived from renewable resources: thermal behavior comparison with PET and PEN Phys. Chem. Chem. Phys. 2014 16 7946 7958
111. T. Matsuo, M. Kamikawa, T. Kondo and N. Maeda, Polyester production process and apparatus, US20140024793A1, 2014
112. E. Gubbels L. Jasinska-Walc B. A. J. Noordover C. E. Koning Linear and branched polyester resins based on dimethyl-2,5-furandicarboxylate for coating applications Eur. Polym. J. 2013 49 3188 3198
113. A. J. J. E. Eerhart M. K. Patel A. P. C. Faaij Fuels and plastics from lignocellulosic biomass via the furan pathway: an economic analysis Biofuels, Bioprod. Biorefin. 2015 9 307 325
114. G. Z. Papageorgiou V. Tsanaktsis D. G. Papageorgiou K. Chrissafis S. Exarhopoulos D. N. Bikiaris Furan-based polyesters from renewable resources: Crystallization and thermal degradation behavior of poly(hexamethylene 2,5-furan-dicarboxylate) Eur. Polym. J. 2015 67 383 396
115. V. Tsanaktsis G. Z. Papageorgiou D. N. Bikiaris A facile method to synthesize high molecular weight biobased polyesters from 2,5-furandicarboxylic acid and long chain diols J. Polym. Sci., Part A: Polym. Chem. 2015 10.1002/pola.27730
116. E. Gubbels L. Jasinska-Walc C. E. Koning Synthesis and characterization of novel renewable polyesters based on 2,5-furandicarboxylic acid and 2,3-butanediol J. Polym. Sci., Part A: Polym. Chem. 2013 51 890 898
117. S. Eritate, Polyester resin, method of producing the same, composition for molded article and molded article, WO2009104780A1, 2009
118. T. M. Research, Bio-succinic acid plant commissioned, 2015
119. B. D. Ahn S. H. Kim Y. H. Kim J. S. Yang Synthesis and characterization of the biodegradable copolymers from succinic acid and adipic acid with 1, 4-butanediol J. Appl. Polym. Sci. 2001 82 2808 2826
120. M. S. Nikolic J. Djonlagic Synthesis and characterization of biodegradable poly (butylene succinate- co -butylene adipate) Polym. Degrad. Stab. 2001 74 263 270
121. V. Tserki P. Matzinos E. Pavlidou D. Vachliotis C. Panayiotou Biodegradable aliphatic polyesters. Part I. Properties and biodegradation of poly(butylene succinate-co-butylene adipate) Polym. Degrad. Stab. 2006 91 367 376
122. H. Wu Z. Qiu Synthesis, crystallization kinetics and morphology of novel poly(ethylene succinate-co-ethylene adipate) copolymers CrystEngComm 2012 14 3586 3595
123. R. Ishioka, E. Kitakuni and Y. Ichikawa, Aliphatic polyesters: "Bionolle". Biopolymers online. 4, ed., A. Steinbüchel, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2005
124. S. Lai Y. Gao L. Yue Heterogeneous catalytic synthesis of poly(butylene succinate) by attapulgite-supported Sn catalyst J. Appl. Polym. Sci. 2015 132 1 9
125. J. Xu B.-H. Guo Poly(butylene succinate) and its copolymers: research, development and industrialization Biotechnol. J. 2010 5 1149 1163
126. W. Pivsa-Art A. Chaiyasat S. Pivsa-Art H. Yamane H. Ohara Preparation of Polymer Blends between Poly(Lactic Acid) and Poly(Butylene adipate-co-terephthalate) and Biodegradable Polymers as Compatibilizers Energy Procedia 2013 34 549 554
127. F. Fenouillot a. Rousseau G. Colomines R. Saint-Loup J.-P. Pascault Polymers from renewable 1,4:3,6-dianhydrohexitols (isosorbide, isomannide and isoidide): A review Prog. Polym. Sci. 2010 35 578 622
128. X. Feng, A. East, W. Hammond and M. Jaffe, Sugar-Based Chemicals for Environmentally Sustainable Applications, in Contemporary Science of Polymeric Materials, ed., L. Korugic-Karasz, American Chemical Society, Washington, 2010, pp. 3-27
129. H. R. Kricheldorf S. Chatti G. Schwarz R.-P. Krüger Macrocycles 27: Cyclic aliphatic polyesters of isosorbide J. Polym. Sci., Part A: Polym. Chem. 2003 41 3414
130. W. J. Yoon K. S. Oh J. M. Koo J. R. Kim K. J. Lee S. S. Im Advanced Polymerization and Properties of Biobased High Tg polyester of Isosorbide and 1,4-Cyclohexanedicarboxylic Acid through in Situ Acetylation Macromolecules 2013 46 2930
131. M. Garaleh T. Yashiro H. R. Kricheldorf P. Simon S. Chatti (Co-)Polyesters Derived from Isosorbide and 1,4-Cyclohexane Dicarboxylic Acid and Succinic Acid Macromol. Chem. Phys. 2010 211 1206
132. O. Goerz H. Ritter Polymers with shape memory effect from renewable resources: crosslinking of polyesters based on isosorbide, itaconic acid and succinic acid Polym. Int. 2013 62 709 712
133. I. S. Ristić N. Vukić S. Cakić V. Simendić O. Ristić J. Budinski-Simendić Synthesis and Characterisation of Polyester Based on Isosorbide and Butanedioic Acid J. Polym. Environ. 2012 20 519 527
134. Q. Lin J. Pasatta T. E. Long Synthesis and characterization of chiral liquid-crystalline polyesters containing sugar-based diols via melt polymerization J. Polym. Sci., Part A: Polym. Chem. 2003 41 2512 2520
135. H. R. Kricheldorf G. Behnken M. Sell Influence of Isosorbide on Glass Transition Temperature and Crystallinity of Poly(butylene terephthalate) J. Macromol. Sci., Part A: Pure Appl. Chem. 2007 44 679 684
136. H. B. Abderrazak A. Fildier S. Marque D. Prim H. B. Romdhane H. R. Kricheldorf S. Chatti Cyclic and non cyclic aliphatic-aromatic polyesters derived from biomass: Study of structures by MALDI-ToF and NMR Eur. Polym. J. 2011 47 2097
137. H. Bengs, A. Schoenfeld, G. Boehm, S. Weis and J. Clauss, Biodegradable polymers based on natural and renewable raw materials especially isosorbide, US6342300B1, 2002
138. T. Ghosh, K. Mahajan, S. Narayan-Sarathy, M. N. Balgacem and P. Gopalakrishnan, 2,5-Furan dicarboxylic acid-based polyesters prepared from biomass, US20130171397A1, 2013
139. M. Chen, H. Yin, W. Dong, Z. Ni, D. Lan and X. Li, Preparation method of low-yellowing 2,5-furandicarboxylic acid-based polyester, CN102516513-A, 2011
140. H. S. Carman Jr., J. I. Killman Jr., E. D. Crawford and J. C. Jenkins, Polyester compositions containing furandicarboxylic acid or an ester thereof, and 2,2,4,4-tetramethyl-1,3-cyclobutanediol, US20130095263 A1, 2013
141. H. S. Carman Jr., J. I. Killman Jr., E. D. Crawford and J. C. Jenkins, Polyester compositions containing furandicarboxylic acid or an ester thereof, cyclobutanediol and cyclohexanedimethanol, US20130095270A1, 2013
142. H. S. Carman Jr., J. I. Killman Jr., E. D. Crawford and J. C. Jenkins, Polyester composition containing furandicarboxylic acid or an ester thereof and ethylene glycol, US20130095269A1, 2013
143. H. S. Carman Jr., J. I. Killman Jr., E. D. Crawford and J. C. Jenkins, Polyester composition containing furandicarboxylic acid or an ester thereof, ethylene glycol and cyclohexanedimethanol, US20130095271A1, 2013
144. H. S. Carman Jr., J. I. Killman Jr., E. D. Crawford and J. C. Jenkins, Polyester compositions containing furandicarboxylic acid or an ester thereof, cyclobutanediol and ethylene glycol, US20130095272A1, 2013
145. R. T. Mathers How well can renewable resources mimic commodity monomers and polymers? J. Polym. Sci., Part A: Polym. Chem. 2012 50 1 15
146. G.-Q. Chen M. K. Patel Plastics Derived from Biological Sources: Present and Future: A Technical and Environmental Review Chem. Rev. 2011 112 2082 2099
147. R. J. Gaymans, Polyamides, in Synthetic methods in step-growth polymers, ed., M. E. Rogers, and, T. E. Long, Wiley, 2003, pp. 135-195
148. V. H. Hopff A. Krieger Über polyamide aus heterocyclischen dicarbonsäuren Die Makromol. Chem. 1961 47 93 113
149. H. Hopff A. Krieger Über decarboxylierung und dissoziation heterocyclischer dicarbonsäuren Helv. Chim. Acta 1961 44 1058 1063
150. P. M. Heertjes G. J. Kok Polycondensation products of 2,5-furandicarboxylic acid Delft Prog. Rep., Ser. A 1974 1 59 63
151. J. C. Salamone, Concise Polymeric Materials Encyclopedia, CRC Press, Boca Raton, 1998
152. M. Russo Ñew heterocyclic polyamides with high heat resistance and mechanical strength Kunststoffe 1975 65 346 352
153. L. Credali and V. Guidotti, Polymeric piperazinamides and membranes for reverse osmosis made therefrom, US4123424, 1978
154. J. A. Moore W. W. Bunting Adv. Polym. Synth. Polym. Sci. Technol. 1985 31 51 91
155. V. P. Sarhevskaya K. A. Kornev S. E. Zmirnova-Zamkova Ukr. Khim. Zh. 1964 30 499
156. A. Mitiakoudis A. Gandini Synthesis and characterization of furanic polyamides Macromolecules 1991 24 830 835
157. A. Mitiakoudis A. Gandini H. Cheradame Polym. Commun. 1985 26 246
158. A. Mitiakoudis and A. Gandini, Poly(p-phenylene-2,5-furandicarbonamide) and anisotropic solutions thereof, their conversion into filaments and films, EP0256606, 1988
159. A. Kehayoglou G. Karayannidis I. Sideridou-Karayannidou Aromatic poly[(amino)amide]s and poly(imidazo[4,5-f]benzimidazole)s derived from poly[(tosylamino)amide]s, 1 Die Makromol. Chem. 1982 183 293 302
160. G. Karayannidis A. Kehayoglou Chim. Chron. New Ser. 1982 11 149 157
161. Avantium-Teijin Aramid and Avantium enter partnership to explore green high-performance polymers http://www.avantium.com/news-events/press-releases/Teijin-Aramid-and-Avantium-enter-partnership-to-explore-green-high-performance-polymers/
162. J. E. Flannigan G. A. Mortimer General molecular weight-lowering side reaction in the thermal condensation of aromatic methyl esters with aromatic amines and hydrazides J. Polym. Sci., Polym. Chem. Ed. 1978 16 1221 1228
163. J. Deng X. Liu C. Li Y. Jiang J. Zhu Synthesis and properties of a bio-based epoxy resin from 2,5-furandicarboxylic acid (FDCA) RSC Adv. 2015 5 15930 15939
164. V. M. Farrugia, G. G. Sacripante, K. Zhou and S. Hadzidedic, Polyester EA Toner Comprising Furan, US 20140170547, 2014
165. D. S. van Es S. Marinkovic X. Oduber B. Estrine Use of Furandicarboxylic Acid and Its Decyl Ester as Additives in the Fischer's Glycosylation of Decanol by d-Glucose: Physicochemical Properties of the Surfactant Compositions Obtained J. Surfactants Deterg. 2012 147 154