Polyesters and Poly(ester-urethane)s from Biobased Difuranic Polyols

ACS Sustainable Chemistry and Engineering

Volumn 4, Issue 12, 2016, Pages 7118-7129

  Mou, Zehuai ^a   Chen, Eugene Y X ^a  

^a Veterinary Dentistry and Oral Surgery   (United States)

Author keywords

5 Hydroxymethylfurfural; Poly(ester urethane); Polyaddition; Polycondensation; Polyester; Polyurethane

Indexed keywords

ALCOHOLS; CHEMICAL BONDS; CHLORINE COMPOUNDS; CROSSLINKING; POLYCONDENSATION; POLYESTERS; POLYOLS; POLYURETHANES;

5 HYDROXYMETHYL FURFURALS; DIELS-ALDER REACTION; HEXAMETHYLENE DIISOCYANATE; PLATFORM CHEMICALS; POLYADDITION; POLYCONDENSATIONS; POLYESTERURETHANES; SEMICRYSTALLINE MATERIALS;

ESTERS;

EID: 85002271218     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/acssuschemeng.6b02007     Document Type: Article

References (71)

1. Gandini, A.; Lacerda, T. M.; Carvalho, A. J.; Trovatti, E. Progress of Polymers from Renewable Resources: Furans, Vegetable Oils, and Polysaccharides Chem. Rev. 2016, 116, 1637-1669 10.1021/acs.chemrev.5b00264
2. Galbis, J. A.; de Gracia Garcia-Martin, M.; de Paz, M. V.; Galbis, E. Synthetic Polymers from Sugar-Based Monomers Chem. Rev. 2016, 116, 1600-1636 10.1021/acs.chemrev.5b00242
3. Mirzaei, H. M.; Karimi, B. Sulphanilic Acid as ARecyclable Bifunctional Organocatalyst in the Selective Conversion of Lignocellulosic Biomass to 5-HMF Green Chem. 2016, 18, 2282-2286 10.1039/C5GC02440D
4. Wrigstedt, P.; Keskivali, J.; Leskela, M.; Repo, T. The Role of Salts and Bronsted Acids in Lewis Acid-Catalyzed Aqueous-Phase Glucose Dehydration to 5-Hydroxymethylfurfural ChemCatChem 2015, 7, 501-507 10.1002/cctc.201402941
5. 6 Carbohydrates for the Production of Hydroxymethylfurfural (HMF) as A Versatile Platform Chemical Green Chem. 2014, 16, 548-572 10.1039/C3GC41365A
6. Teong, S. P.; Yi, G.; Zhang, Y. Hydroxymethylfurfural Production from Bioresources: Past, Present and Future Green Chem. 2014, 16, 2015-2026 10.1039/c3gc42018c
7. He, J.; Zhang, Y.; Chen, E. Y. X. Chromium(0) Nanoparticles as Effective Catalyst for the Conversion of Glucose into 5-Hydroxymethylfurfural ChemSusChem 2013, 6, 61-64 10.1002/cssc.201200795
8. 12Furoin and Alkane Fuel ACS Catal. 2014, 4, 1302-1310 10.1021/cs500058p
9. Zuo, X.; Venkitasubramanian, P.; Busch, D. H.; Subramaniam, B. Optimization of Co/Mn/Br-Catalyzed Oxidation of 5-Hydroxymethylfurfural to Enhance 2,5-Furandicarboxylic Acid Yield and Minimize Substrate Burning ACS Sustainable Chem. Eng. 2016, 4, 3659 10.1021/acssuschemeng.6b00174
10. Zhang, Z. H.; Zhen, J. D.; Liu, B.; Lv, K. L.; Deng, K. J. Selective Aerobic Oxidation of the Biomass-Derived Precursor 5-Hydroxymethylfurfural to 2,5-Furandicarboxylic Acid under Mild Conditions over AMagnetic Palladium Nanocatalyst Green Chem. 2015, 17, 1308-1317 10.1039/C4GC01833H
11. 4-CoOxMagnetite Nanocatalyst ACS Sustainable Chem. Eng. 2015, 3, 406-412 10.1021/sc500702q
12. Han, X.; Geng, L.; Guo, Y.; Jia, R.; Liu, X.; Zhang, Y.; Wang, Y. Base-Free Aerobic Oxidation of 5-Hydroxymethylfurfural to 2,5-Furandicarboxylic Acid over a Pt/C-O-Mg catalyst Green Chem. 2016, 18, 1597-1604 10.1039/C5GC02114F
13. Yi, G.; Teong, S. P.; Li, X.; Zhang, Y. Purification of Biomass-Derived 5-Hydroxymethylfurfural and Its Catalytic Conversion to 2,5-Furandicarboxylic Acid ChemSusChem 2014, 7, 2131-2135 10.1002/cssc.201402105
14. Yi, G.; Teong, S. P.; Zhang, Y. Base-Free Conversion of 5-Hydroxymethylfurfural to 2,5-Furandicarboxylic Acid over a Ru/C Catalyst Green Chem. 2016, 18, 979-983 10.1039/C5GC01584G
15. Hao, W.; Li, W.; Tang, X.; Zeng, X.; Sun, Y.; Liu, S.; Lin, L. Catalytic Transfer Hydrogenation of Biomass-Derived 5-Hydroxymethyl Furfural to the Building Block 2,5-Bishydroxymethyl Furan Green Chem. 2016, 18, 1080-1088 10.1039/C5GC01221J
16. De, S.; Kumar, T.; Bohre, A.; Singh, L. R.; Saha, B. Furan-Based Acetylating Agent for the Chemical Modification of Proteins Bioorg. Med. Chem. 2015, 23, 791-796 10.1016/j.bmc.2014.12.053
17. Chatterjee, M.; Ishizaka, T.; Kawanami, H. Selective Hydrogenation of 5-Hydroxymethylfurfural to 2,5-Bis-(hydroxymethyl)furan Using Pt/MCM-41 in An Aqueous Medium: A Simple Approach Green Chem. 2014, 16, 4734-4739 10.1039/C4GC01127A
18. Cao, Q.; Liang, W.; Guan, J.; Wang, L.; Qu, Q.; Zhang, X.; Wang, X.; Mu, X. Catalytic Synthesis of 2,5-Bis-methoxymethylfuran: A Promising Cetane Number Improver for Diesel Appl. Catal., A 2014, 481, 49-53 10.1016/j.apcata.2014.05.003
19. Cottier, L.; Descotes, G.; Soro, Y. Heteromacrocycles from Ring-Closing Metathesis of Unsaturated Furanic Ethers Synth. Commun. 2003, 33, 4285-4295 10.1081/SCC-120026858
20. Jiang, M.; Liu, Q.; Zhang, Q.; Ye, C.; Zhou, G. Y. A Series of Furan-Aromatic Polyesters Synthesized via Direct Esterification Method Based on Renewable Resources J. Polym. Sci., Part A: Polym. Chem. 2012, 50, 1026-1036 10.1002/pola.25859
21. Ma, J. P.; Pang, Y.; Wang, M.; Xu, J.; Ma, H.; Nie, X. The Copolymerization Reactivity of Diols with 2,5-Furandicarboxylic Acid for Furan-Based Copolyester Materials J. Mater. Chem. 2012, 22, 3457-3461 10.1039/c2jm15457a
22. Wu, L. B.; Mincheva, R.; Xu, Y. T.; Raquez, J. M.; Dubois, P. High Molecular Weight Poly(butylene succinate-co-butylene furandicarboxylate) Copolyesters: From Catalyzed Polycondensation Reaction to Thermomechanical Properties Biomacromolecules 2012, 13, 2973-2981 10.1021/bm301044f
23. Zhu, J.; Cai, J.; Xie, W.; Chen, P.-H.; Gazzano, M.; Scandola, M.; Gross, R. A. Poly(butylene 2,5-furan dicarboxylate), A Biobased Alternative to PBT: Synthesis, Physical Properties, and Crystal Structure Macromolecules 2013, 46, 796-804 10.1021/ma3023298
24. Tsanaktsis, V.; Terzopoulou, Z.; Exarhopoulos, S.; Bikiaris, D. N.; Achilias, D. S.; Papageorgiou, D. G.; Papageorgiou, G. Z. Sustainable, Eco-Friendly Polyesters Synthesized from Renewable Resources: Preparation and Thermal Characteristics of Poly(dimethyl-propylene furanoate) Polym. Chem. 2015, 6, 8284-8296 10.1039/C5PY01367D
25. Gandini, A.; Silvestre, A. J. D.; Neto, C. P.; Sousa, A. F.; Gomes, M. 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 10.1002/pola.23130
26. Jiang, Y.; Woortman, A. J.; Alberda van Ekenstein, G. O.; Petrovic, D. M.; Loos, K. Enzymatic Synthesis of Biobased Polyesters Using 2,5-Bis(hydroxymethyl)furan as the Building Block Biomacromolecules 2014, 15, 2482-2493 10.1021/bm500340w
27. Zeng, C.; Seino, H.; Ren, J.; Hatanaka, K.; Yoshie, N. Bio-Based Furan Polymers with Self-Healing Ability Macromolecules 2013, 46, 1794-1802 10.1021/ma3023603
28. Gomes, M.; Gandini, A.; Silvestre, A. J. D.; Reis, B. Synthesis and Characterization of Poly(2,5-furan dicarboxylate)s Based on AVariety of Diols J. Polym. Sci., Part A: Polym. Chem. 2011, 49, 3759-3768 10.1002/pola.24812
29. Wang, H.; Wang, Y.; Deng, T.; Chen, C.; Zhu, Y.; Hou, X. Carbocatalyst in Biorefinery: Selective Etherification of 5-Hydroxymethylfurfural to 5,5 '(oxy-bis(methylene)bis-2-furfural over Graphene Oxide Catal. Commun. 2015, 59, 127-130 10.1016/j.catcom.2014.10.009
30. Chang, C.-C.; Cho, H. J.; Yu, J.; Gorte, R. J.; Gulbinski, J.; Dauenhauer, P.; Fan, W. Lewis Acid Zeolites for Tandem Diels-Alder Cycloaddition and Dehydration of Biomass-Derived Dimethylfuran and Ethylene to Renewable p-Xylene Green Chem. 2016, 18, 1368-1376 10.1039/C5GC02164B
31. Foster, R. W.; Benhamou, L.; Porter, M. J.; Bucar, D.-K.; Hailes, H. C.; Tame, C. J.; Sheppard, T. D. Irreversible Endo-Selective Diels-Alder Reactions of Substituted Alkoxyfurans: A General Synthesis of Endo-Cantharimides Chem.-Eur. J. 2015, 21, 6107-6114 10.1002/chem.201406286
32. Xue, Y.-P.; Li, W.-D. Z. Formal Total Synthesis of (±)-Estrone via the Furano Diene Approach J. Org. Chem. 2011, 76, 57-64 10.1021/jo1015486
33. Shiramizu, M.; Toste, F. D. On the Diels-Alder Approach to Solely Biomass-Derived Polyethylene Terephthalate (PET): Conversion of 2,5-Dimethylfuran and Acrolein into p-Xylene Chem.-Eur. J. 2011, 17, 12452-12457 10.1002/chem.201101580
34. Sim, J. Y.; Hwang, G.-S.; Kim, K. H.; Ko, E. M.; Ryu, D. H. Asymmetric Synthesis of (+)-Cis-nemorensic Acid from A Chiral Diels-Alder Adduct of 2,5-Dimethylfuran Chem. Commun. 2007, 5064-5065 10.1039/b710537a
35. Griffith, G. A.; Hillier, I. H.; Moralee, A. C.; Percy, J. M.; Roig, R.; Vincent, M. A. Interplay of Structure and Reactivity in AMost Unusual Furan Diels-Alder Reaction J. Am. Chem. Soc. 2006, 128, 13130-13141 10.1021/ja061458p
36. Petronijevic, F.; Timmons, C.; Cuzzupe, A.; Wipf, P. A Microwave Assisted Intramolecular-Furan-Diels-Alder Approach to 4-Substituted Indoles Chem. Commun. 2008, 104-106 10.1039/B816989F
37. 4-Mediated Diels-Alder Reaction of Furan Angew. Chem., Int. Ed. 2002, 41, 4079-4082 10.1002/1521-3773(20021104)41:21<4079::AID-ANIE4079>3.0.CO;2-N
38. Gandini, A. The Furan/Maleimide Diels-Alder Reaction: A Versatile Click-Unclick Tool in Macromolecular Synthesis Prog. Polym. Sci. 2013, 38, 1-29 10.1016/j.progpolymsci.2012.04.002
39. Liu, Y.-L.; Chuo, T.-W. Self-Healing Polymers Based on Thermally Reversible Diels-Alder Chemistry Polym. Chem. 2013, 4, 2194-2205 10.1039/c2py20957h
40. Watanabe, M.; Yoshie, N. Synthesis and Properties of Readily Recyclable Polymers from Bisfuranic Terminated Poly(ethylene adipate) and Multi-Maleimide Linkers Polymer 2006, 47, 4946-4952 10.1016/j.polymer.2006.05.036
41. Yamashiro, M.; Inoue, K.; Iji, M. Recyclable Shape-Memory and Mechanical Strength of Poly(lactic acid) Compounds Cross-Linked by Thermo-Reversible Diels-Alder Reaction Polym. J. 2008, 40, 657-662 10.1295/polymj.PJ2008042
42. Defize, T.; Riva, R.; Thomassin, J. M.; Jerome, C.; Alexandre, M. Thermo-Reversible Reactions for the Preparation of Smart Materials: Recyclable Covalently-Crosslinked Shape Memory Polymers Macromol. Symp. 2011, 309-310, 154-161 10.1002/masy.201100036
43. Defize, T.; Riva, R.; Raquez, J. M.; Dubois, P.; Jerome, C.; Alexandre, M. Thermoreversibly Crosslinked Poly(epsilon-caprolactone) as Recyclable Shape-Memory Polymer Network Macromol. Rapid Commun. 2011, 32, 1264-1269 10.1002/marc.201100250
44. Zeng, C.; Seino, H.; Ren, J.; Yoshie, N. Polymers with Multishape Memory Controlled by Local Glass Transition Temperature ACS Appl. Mater. Interfaces 2014, 6, 2753-2758 10.1021/am405287p
45. Kavitha, A. A.; Singha, N. K. Click Chemistry in Tailor-Made Polymethacrylates Bearing Reactive Furfuryl Functionality: A New Class of Self-Healing Polymeric Material ACS Appl. Mater. Interfaces 2009, 1, 1427-1436 10.1021/am900124c
46. Peterson, A. M.; Jensen, R. E.; Palmese, G. R. Room-Temperature Healing of A Thermosetting Polymer Using the Diels-Alder Reaction ACS Appl. Mater. Interfaces 2010, 2, 1141-1149 10.1021/am9009378
47. He, J. H.; Zhang, Y. T.; Chen, E. Y. X. Anionic Polymerization of Biomass-Derived Furfuryl Methacrylate: Controlling Polymer Tacticity and Thermoreversibility J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 2793-2803 10.1002/pola.26679
48. Chen, X. X.; Dam, M. A.; Ono, K.; Mal, A.; Shen, H. B.; Nutt, S. R.; Sheran, K.; Wudl, F. A Thermally Re-mendable Cross-Linked Polymeric Material Science 2002, 295, 1698-1702 10.1126/science.1065879
49. Zeng, C.; Seino, H.; Ren, J.; Hatanaka, K.; Yoshie, N. Self-Healing Bio-Based Furan Polymers Cross-Linked with Various Bis-Maleimides Polymer 2013, 54, 5351-5357 10.1016/j.polymer.2013.07.059
50. Ikezaki, T.; Matsuoka, R.; Hatanaka, K.; Yoshie, N. Biobased Poly(2,5-furandimethylene succinate-co-butylene succinate) Crosslinked by Reversible Diels-Alder Reaction J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 216-222 10.1002/pola.26990
51. Hong, M.; Tang, X.; Falivene, L.; Caporaso, L.; Cavallo, L.; Chen, E. Y. X. Proton-Transfer Polymerization by N-Heterocyclic Carbenes: Monomer and Catalyst Scopes and Mechanism for Converting Dimethacrylates into Unsaturated Polyesters J. Am. Chem. Soc. 2016, 138, 2021-2035 10.1021/jacs.5b13019
52. Liu, D. J.; Zhang, Y. T.; Chen, E. Y. X. Organocatalytic Upgrading of the Key Biorefining Building Block by A Catalytic Ionic Liquid and N-heterocyclic Carbenes Green Chem. 2012, 14, 2738-2746 10.1039/c2gc36265a
53. Mou, Z. H.; Feng, S.; Chen, E. Y. X. Bio-Based Difuranic Polyol Monomers and Their Derived Linear and Cross-Linked Polyurethanes Polym. Chem. 2016, 7, 1593-1602 10.1039/C5PY02032H
54. Liu, D.; Chen, E. Y. X. Organocatalysis in Biorefining for Biomass Conversion and Upgrading Green Chem. 2014, 16, 964-981 10.1039/C3GC41934G
55. Liu, D.; Chen, E. Y. Diesel and Alkane Fuels from Biomass by Organocatalysis and Metal-Acid Tandem Catalysis ChemSusChem 2013, 6, 2236-2239 10.1002/cssc.201300476
56. Yan, Y.; Siegwart, D. J. Scalable Synthesis and Derivation of Functional Polyesters Bearing Ene and Epoxide Side Chains Polym. Chem. 2014, 5, 1362-1371 10.1039/C3PY01474F
57. Canadell, J.; Fischer, H.; De With, G.; van Benthem, R. A. T. M. Stereoisomeric Effects in Thermo-Remendable Polymer Networks Based on Diels-Alder Crosslink Reactions J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 3456-3467 10.1002/pola.24134
58. Hager, M. D.; Bode, S.; Weber, C.; Schubert, U. S. Shape Memory Polymers: Past, Present and Future Developments Prog. Polym. Sci. 2015, 49-50, 3-33 10.1016/j.progpolymsci.2015.04.002
59. Genovese, L.; Soccio, M.; Gigli, M.; Lotti, N.; Gazzano, M.; Siracusa, V.; Munari, A. Gas Permeability, Mechanical Behaviour and Compostability of Fully-Aliphatic Bio-Based Multiblock Poly(ester urethane)s RSC Adv. 2016, 6, 55331-55342 10.1039/C6RA08882A
60. Oulame, M. Z.; Pion, F.; Allauddin, S.; Raju, K. V. S. N.; Ducrot, P.-H.; Allais, F. Renewable Alternating Aliphatic-Aromatic Poly(ester-urethane)s Prepared from Ferulic Acid and Bio-Based Diols Eur. Polym. J. 2015, 63, 186-193 10.1016/j.eurpolymj.2014.11.031
61. Yao, X.; Wu, G.; Xu, L.; Zhang, H.; Yan, Y. Enzyme-Catalyzed Preparation of Dimeric Acid Polyester Polyol from Biodiesel and Its Further Use in the Synthesis of Polyurethane RSC Adv. 2014, 4, 31062 10.1039/C4RA03286A
62. Bothe, M.; Emmerling, F.; Pretsch, T. Poly(ester urethane) with Varying Polyester Chain Length: Polymorphism and Shape-Memory Behavior Macromol. Chem. Phys. 2013, 214, 2683-2693 10.1002/macp.201300464
63. Fritzsche, N.; Pretsch, T. Programming of Temperature-Memory Onsets in a Semicrystalline Polyurethane Elastomer Macromolecules 2014, 47, 5952-5959 10.1021/ma501171p
64. Bothe, M.; Pretsch, T. Two-Way Shape Changes of a Shape-Memory Poly(ester urethane) Macromol. Chem. Phys. 2012, 213, 2378-2385 10.1002/macp.201200096
65. Wang, W.; Jin, Y.; Ping, P.; Chen, X.; Jing, X.; Su, Z. Structure Evolution in Segmented Poly(ester urethane) in Shape-Memory Process Macromolecules 2010, 43, 2942-2947 10.1021/ma902781e
66. Shetranjiwalla, S.; Li, S. J.; Bouzidi, L.; Narine, S. S. Imparting Elastomeric Properties to Entirely Lipid-Derived Thermoplastic Poly(ester urethane)s: Molecular Weight Control Polymer 2016, 92, 140-152 10.1016/j.polymer.2016.04.004
67. Pretsch, T.; Jakob, I.; Müller, W. Hydrolytic Degradation and Functional Stability of A Segmented Shape Memory Poly(ester urethane) Polym. Degrad. Stab. 2009, 94, 61-73 10.1016/j.polymdegradstab.2008.10.012
68. Zha, L.; Wu, M.; Yang, J. Hydrogen Bonding and Morphological Structure of Segmented Polyurethanes Based on Hydroquinone- Bis(β-hydroxyethy)ether as A Chain Extender J. Appl. Polym. Sci. 1999, 73, 2895-2902 10.1002/(SICI)1097-4628(19990929)73:14<2895::AID-APP13>3.0.CO;2-E
69. Wang, Z.; Zhang, X.; Zhang, L.; Tan, T.; Fong, H. Nonisocyanate Biobased Poly(ester urethanes) with Tunable Properties Synthesized via an Environment-Friendly Route ACS Sustainable Chem. Eng. 2016, 4, 2762-2770 10.1021/acssuschemeng.6b00275
70. Zeng, J.-B.; Li, Y.-D.; Zhu, Q.-Y.; Yang, K.-K.; Wang, X.-L.; Wang, Y.-Z. A Novel Biodegradable Multiblock Poly(ester urethane) Containing Poly(l-lactic acid) and Poly(butylene succinate) Blocks Polymer 2009, 50, 1178-1186 10.1016/j.polymer.2009.01.001
71. Caracciolo, P. C.; Thomas, V.; Vohra, Y. K.; Buffa, F.; Abraham, G. A. Electrospinning of Novel Biodegradable Poly(ester urethane)s and Poly(ester urethane urea)s for Soft Tissue-Engineering Applications J. Mater. Sci.: Mater. Med. 2009, 20, 2129-2137 10.1007/s10856-009-3768-3