Isocyanate-Free Routes to Polyurethanes and Poly(hydroxy Urethane)s

Chemical Reviews

Volumn 115, Issue 22, 2015, Pages 12407-12439

  Maisonneuve, Lise ^a,b   Lamarzelle, Océane ^a,b   Rix, Estelle ^a,b   Grau, Etienne ^a,b   Cramail, Henri ^a,b  

^a UNIVERSITÉ DE BORDEAUX   (France)

^b UNIVERSITÉ BORDEAUX 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCONDENSATION;

ISOCYANATE-FREE; POLYADDITION; POLYISOCYANATES; SYNTHETIC ROUTES;

POLYURETHANES;

EID: 84948679700     PISSN: 00092665     EISSN: 15206890     Source Type: Journal    
DOI: 10.1021/acs.chemrev.5b00355     Document Type: Review

References (232)

1. PlasticsEurope. Plastics: The Facts 2013. www.plasticseurope.org/Document/plastics-the-facts-2013.aspx (accessed October 22, 2015).
2. Kreye, O.; Mutlu, H.; Meier, M. A. R. Sustainable routes to polyurethane precursors Green Chem. 2013, 15, 1431-1455 10.1039/c3gc40440d
3. Ihata, O.; Kayaki, Y.; Ikariya, T. Synthesis of Thermoresponsive Polyurethane from 2-Methylaziridine and Supercritical Carbon Dioxide Angew. Chem., Int. Ed. 2004, 43, 717-719 10.1002/anie.200352215
4. Palaskar, D. V.; Boyer, A.; Cloutet, E.; Alfos, C.; Cramail, H. Synthesis of biobased polyurethane from oleic and ricinoleic acids as the renewable resources via the AB-type self-condensation approach Biomacromolecules 2010, 11, 1202-1211 10.1021/bm100233v
5. More, A. S.; Gadenne, B.; Alfos, C.; Cramail, H. AB type polyaddition route to thermoplastic polyurethanes from fatty acid derivatives Polym. Chem. 2012, 3, 1594-1605 10.1039/c2py20123b
6. Hahn, C.; Keul, H.; Möller, M. Hydroxyl-functional polyurethanes and polyesters: synthesis, properties and potential biomedical application Polym. Int. 2012, 61, 1048-1060 10.1002/pi.4242
7. Delebecq, E.; Pascault, J.-P.; Boutevin, B.; Ganachaud, F. On the Versatility of Urethane/Urea Bonds: Reversibility, Blocked Isocyanate, and Non-isocyanate Polyurethane Chem. Rev. 2013, 113, 80-118 10.1021/cr300195n
8. Guan, J.; Song, Y.; Lin, Y.; Yin, X.; Zuo, M.; Zhao, Y.; Tao, X.; Zheng, Q. Progress in Study of Non-Isocyanate Polyurethane Ind. Eng. Chem. Res. 2011, 50, 6517-6527 10.1021/ie101995j
9. Kathalewar, M. S.; Joshi, P. B.; Sabnis, A. S.; Malshe, V. C. Non-isocyanate polyurethanes: from chemistry to applications RSC Adv. 2013, 3, 4110-4129 10.1039/c2ra21938g
10. Pyo, S.-H.; Persson, P.; Mollaahmad, M. A.; Sörensen, K.; Lundmark, S.; Hatti-Kaul, R. Cyclic carbonates as monomers for phosgene and isocyanate-free polyurethanes and polycarbonates Pure Appl. Chem. 2011, 84, 411-860 10.1351/PAC-CON-11-06-14
11. Nohra, B.; Candy, L.; Blanco, J.-F.; Guerin, C.; Raoul, Y.; Mouloungui, Z. From Petrochemical Polyurethanes to Biobased Polyhydroxyurethanes Macromolecules 2013, 46, 3771-3792 10.1021/ma400197c
12. Blattmann, H.; Fleischer, M.; Bähr, M.; Mülhaupt, R. Isocyanate- and Phosgene-Free Routes to Polyfunctional Cyclic Carbonates and Green Polyurethanes by Fixation of Carbon Dioxide Macromol. Rapid Commun. 2014, 35, 1238-1254 10.1002/marc.201400209
13. Jayakannan, M.; Puthanparambil, D. U.S. Patent US20070117950, 2007.
14. Chem. Abstr. 2007, 146, 522671.
15. Romano, U.; Tesel, R.; Mauri, M. M.; Rebora, P. Synthesis of Dimethyl Carbonate from Methanol, Carbon Monoxide, and Oxygen Catalyzed by Copper Compounds Ind. Eng. Chem. Prod. Res. Dev. 1980, 19, 396-403 10.1021/i360075a021
16. Sakai, S.; Fujinami, T.; Yamada, T.; Furusawa, S. Reaction of Organotin Alkoxides with Carbon Disulfide, Carbony Sulfide or Carbon Dioxide Nippon Kagaku Kaishi 1975, 19, 1789-1794 10.1246/nikkashi.1975.1789
17. Peng, W.; Zhao, N.; Xiao, F.; Wei, W.; Sun, Y. Recent progress in phosgene-free methods for synthesis of dimethyl carbonate Pure Appl. Chem. 2011, 84, 603-620 10.1351/PAC-CON-11-06-02
18. Ono, Y. Dimethyl carbonate for environmentally benign reactions Catal. Today 1997, 35, 15-25 10.1016/S0920-5861(96)00130-7
19. Buysch, H. J.; Krimm, H.; Richter, W. Canadian Patent CA1166649, 1982.
20. Chem. Abstr. 1982, 97, 55505.
21. Baba, T.; Kobayashi, A.; Yamauchi, T.; Tanaka, H.; Aso, S.; Inomata, M.; Kawanami, Y. Catalytic Methoxycarbonylation of Aromatic Diamines with Dimethyl Carbonate to Their Dicarbamates Using Zinc Acetate Catal. Lett. 2002, 82, 193-197 10.1023/A:1020566928295
22. Baba, T.; Fujiwara, M.; Oosaku, A.; Kobayashi, A.; Deleon, R. G.; Ono, Y. Catalytic synthesis of N -alkyl carbamates by methoxycarbonylation of alkylamines with dimethyl carbonate using Pb(NO3)2 Appl. Catal., A 2002, 227, 1-6 10.1016/S0926-860X(01)00939-5
23. Deleon, R. G.; Kobayashi, A.; Yamauchi, T.; Ooishi, J.; Baba, T.; Sasaki, M.; Hiarata, F. Catalytic methoxycarbonylation of 1,6-hexanediamine with dimethyl carbonate to dimethylhexane-1,6-dicarbamate using Bi(NO3)3 Appl. Catal., A 2002, 225, 43-49 10.1016/S0926-860X(01)00692-5
24. Deepa, P.; Jayakannan, M. Solvent-Free and Nonisocyanate Melt Transurethane Reaction for Aliphatic Polyurethanes and Mechanistic Aspects J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 2445-2458 10.1002/pola.22578
25. Deepa, P.; Jayakannan, M. Solvent-induced self-organization approach for polymeric architectures of micropores, hexagons and spheres based on polyurethanes prepared via novel melt transurethane methodology J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 2351-2366 10.1002/pola.22058
26. Deepa, P.; Jayakannan, M. Polyurethane-oligo(phenylenevinylene) random copolymers: π-Conjugated pores, vesicles, and nanospheres via solvent-induced self-organization J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 5897-5915 10.1002/pola.22907
27. Duval, C.; Kébir, N.; Charvet, A.; Martin, A.; Burel, F. Synthesis and properties of renewable nonisocyanate polyurethanes (NIPUs) from dimethylcarbonate J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 1351-1359 10.1002/pola.27568
28. Firdaus, M.; Meier, M. A. R. Renewable polyamides and polyurethanes derived from limonene Green Chem. 2013, 15, 370-380 10.1039/C2GC36557J
29. Tang, D.; Mulder, D.-J.; Noordover, B. A. J.; Koning, C. E. Well-defined Biobased Segmented Polyureas Synthesis via a TBD-catalyzed Isocyanate-free Route Macromol. Rapid Commun. 2011, 32, 1379-1385 10.1002/marc.201100223
30. Distaso, M.; Quaranta, E. Highly selective carbamation of aliphatic diamines under mild conditions using Sc(OTf)3 as catalyst and dimethyl carbonate as a phosgene substitute Appl. Catal., B 2006, 66, 72-80 10.1016/j.apcatb.2006.02.019
31. Kumar, S.; Jain, S. L. l-Proline-TBAB-catalyzed phosgene free synthesis of methyl carbamates from amines and dimethyl carbonate New J. Chem. 2013, 37, 2935-2935 10.1039/c3nj00643c
32. Zhou, H.; Shi, F.; Tian, X.; Zhang, Q.; Deng, Y. Synthesis of carbamates from aliphatic amines and dimethyl carbonate catalyzed by acid functional ionic liquids J. Mol. Catal. A: Chem. 2007, 271, 89-92 10.1016/j.molcata.2007.02.017
33. Margetić, D.; Antonac, I. Z.; Glasovac, Z.; Eckert-Maksić, M.; Maksimović, L. Reactions of Dimethyl Carbonate with Aliphatic Amines Under High Pressure Synth. Commun. 2011, 41, 2283-2289 10.1080/00397911.2010.501644
34. Selva, M.; Tundo, P.; Perosa, A. The synthesis of alkyl carbamates from primary aliphatic amines and dialkyl carbonates in supercritical carbon dioxide Tetrahedron Lett. 2002, 43, 1217-1219 10.1016/S0040-4039(01)02390-5
35. Carloni, S.; De Vos, D. E.; Jacobs, P. A.; Maggi, R.; Sartori, G.; Sartorio, R. Catalytic Activity of MCM-41-TBD in the Selective Preparation of Carbamates and Unsymmetrical Alkyl Carbonates from Diethyl Carbonate J. Catal. 2002, 205, 199-204 10.1006/jcat.2001.3439
36. Sharma, B.; Keul, H.; Höcker, H.; Loontjens, T.; Benthem, R. v. Synthesis and characterization of alternating poly(amide urethane)s from ε-caprolactone, diamines and diphenyl carbonate Polymer 2005, 46, 1775-1783 10.1016/j.polymer.2004.11.024
37. Sharma, B.; Ubaghs, L.; Keul, H.; Höcker, H.; Loontjens, T.; Benthem, R. v. Synthesis and characterization of alternating poly(amide urethane)s from ε-caprolactam, amino alcohols, and diphenyl carbonate Polymer 2004, 45, 5427-5440 10.1016/j.polymer.2004.05.046
38. Blank, W. J. U.S. Patent US4820830, 1989. Chem. Abstr. 1989, 110, 116822.
39. Coury, J. A.; Hobot, C. M. U.S. Patent US4883854, 1989. Chem. Abstr. 1989, 114, 7398.
40. McCabe, R. W.; Taylor, A. Synthesis of novel polyurethane polyesters using the enzyme Candida antarctica lipase B Green Chem. 2004, 6, 151 10.1039/b400372c
41. Rokicki, G.; Piotrowska, A. A new route to polyurethanes from ethylene carbonate, diamines and diols Polymer 2002, 43, 2927-2935 10.1016/S0032-3861(02)00071-X
42. Deng, Y.; Li, S.; Zhao, J. B.; Zhang, Z.; Zhang, J.; Yang, W. Crystallizable and tough aliphatic thermoplastic poly(ether urethane)s synthesized through a non-isocyanate route RSC Adv. 2014, 4, 43406-43414 10.1039/C4RA05880A
43. Li, C.; Li, S.; Zhao, J.; Zhang, Z.; Zhang, J.; Yang, W. Synthesis and characterization of aliphatic poly(amide urethane)s having different nylon 6 segments through non-isocyanate route J. Polym. Res. 2014, 21. 10.1007/s10965-014-0498-0
44. Sharma, B.; Ubaghs, L.; Keul, H.; Höcker, H.; Loontjens, T.; van Benthem, R. Microstructure and Properties of Poly(amide urethane)s: Comparison of the Reactivity of α-Hydroxy-ω-O-phenyl Urethanes and α-Hydroxy-ω-O-hydroxyethyl Urethanes Macromol. Chem. Phys. 2004, 205, 1536-1546 10.1002/macp.200400056
45. Unverferth, M.; Kreye, O.; Prohammer, A.; Meier, M. A. R. Renewable Non-Isocyanate Based Thermoplastic Polyurethanes via Polycondensation of Dimethyl Carbamate Monomers with Diols Macromol. Rapid Commun. 2013, 34, 1569-1574 10.1002/marc.201300503
46. Dongdong, P.; Hengshui, T. Polycarbonate polyurethane elastomers synthesized via a solvent-free and nonisocyanate melt transesterification process J. Appl. Polym. Sci. 2015, 132, 41377 10.1002/app.41377
47. Dyer, E.; Scott, H. The Preparation of Polymeric and Cyclic Urethans and Ureas from Ethylene Carbonate and Amines J. Am. Chem. Soc. 1957, 79, 672-675 10.1021/ja01560a045
48. Li, S.; Zhao, J.; Zhang, Z.; Zhang, J.; Yang, W. Synthesis and characterization of aliphatic segmented poly(ether amide urethane)s through a non-isocyanate route RSC Adv. 2014, 4, 23720 10.1039/c4ra02325k
49. Ochiai, B.; Utsuno, T. Non-isocyanate synthesis and application of telechelic polyurethanes via polycondensation of diurethanes obtained from ethylene carbonate and diamines J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 525-533 10.1002/pola.26418
50. Neffgen, S.; Keul, H.; Höcker, H. Polymerization of 2,2-dimethyltrimethylene urethane; a disfavoured process Macromol. Chem. Phys. 1998, 199, 197-206 10.1002/(SICI)1521-3935(19980201)199:2197::AID-MACP1973.0.CO;2-U
51. Hablot, E.; Graiver, D.; Narayan, R. Efficient synthesis of biobased poly(amide urethane)s via non-isocyanate route PU Magazine International 2012, 9, 255-257
52. Firdaus, M.; Meier, M. a. R. Renewable polyamides and polyurethanes derived from limonene Green Chem. 2013, 15, 370-380 10.1039/C2GC36557J
53. Palaskar, D. V.; Boyer, A. l.; Cloutet, E.; Alfos, C.; Cramail, H. Synthesis of Biobased Polyurethane from Oleic and Ricinoleic Acids as the Renewable Resources via the AB-Type Self-Condensation Approach Biomacromolecules 2010, 11, 1202-1211 10.1021/bm100233v
54. Deng, Y.; Li, S.-q.; Zhao, J.-b.; Zhang, Z.-y.; Zhang, J.-y.; Yang, W.-t. Aliphatic thermoplastic poly(ether urethane)s having long PEG sequences synthesized through a non-isocyanate route Chin. J. Polym. Sci. 2015, 33, 880-889 10.1007/s10118-015-1638-7
55. Kreye, O.; Wald, S.; Meier, M. A. R. Introducing Catalytic Lossen Rearrangements: Sustainable Access to Carbamates and Amines Adv. Synth. Catal. 2013, 355, 81-86 10.1002/adsc.201200760
56. Groszos, S. J.; Drechsel, D. a. E. K. U.S. Patent US2802022, 1957.
57. Chem. Abstr. 1957, 51, 99381.
58. Webster, D. C. Cyclic carbonate functional polymers and their applications Prog. Org. Coat. 2003, 47, 77-86 10.1016/S0300-9440(03)00074-2
59. Rokicki, G.; Parzuchowski, P. Polymer Science: A Comprehensive Reference; Elsevier: Amsterdam, 2012; Vol. 4.
60. Besse, V.; Camara, F.; Voirin, C.; Auvergne, R.; Caillol, S.; Boutevin, B. Synthesis and applications of unsaturated cyclocarbonates Polym. Chem. 2013, 4, 4545-4561 10.1039/c3py00343d
61. Figovsky, O.; Shapovalov, L.; Leykin, A.; Birukova, O.; Potashnikova, R. Progress in elaboration of nonisocyanate polyurethanes based on cyclic carbonates Int. Lett. Chem., Phys. Astron. 2013, 3, 52-66 10.18052/www.scipress.com/ILCPA.3.52
62. Rokicki, G.; Parzuchowski, P. G.; Mazurek, M. Non-isocyanate polyurethanes: synthesis, properties, and applications Polym. Adv. Technol. 2015, 26, 707-761 10.1002/pat.3522
63. Figovsky, O.; Shapovalov, L.; Leykin, A.; Birukova, O.; Potashnikova, R. Advances in the field of nonisocyanate polyurethanes based on cyclic carbonates Chem. Chem. Technol. 2013, 7, 79-87
64. Tomita, H.; Sanda, F.; Endo, T. Polyaddition behavior of bis(five- and six-membered cyclic carbonate)s with diamine J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 860-867 10.1002/1099-0518(20010315)39:6860::AID-POLA10593.0.CO;2-2
65. Ochoa-Gómez, J. R.; Gómez-Jiménez-Aberasturi, O.; Ramírez-López, C.; Belsué, M. A Brief Review on Industrial Alternatives for the Manufacturing of Glycerol Carbonate, a Green Chemical Org. Process Res. Dev. 2012, 16, 389-399 10.1021/op200369v
66. Behr, A.; Eilting, J.; Irawadi, K.; Leschinski, J.; Lindner, F. Improved utilisation of renewable resources: New important derivatives of glycerol Green Chem. 2008, 10, 13-30 10.1039/B710561D
67. Sonnati, M. O.; Amigoni, S.; Taffin de Givenchy, E. P.; Darmanin, T.; Choulet, O.; Guittard, F. Glycerol carbonate as a versatile building block for tomorrow green chemistry: synthesis, reactivity, properties and applications Green Chem. 2013, 15, 283-306 10.1039/C2GC36525A
68. Shaikh, A.-A. G.; Sivaram, S. Organic Carbonates Chem. Rev. 1996, 96, 951-976 10.1021/cr950067i
69. Rokicki, G. Aliphatic cyclic carbonates and spiroorthocarbonates as monomers Prog. Polym. Sci. 2000, 25, 259-342 10.1016/S0079-6700(00)00006-X
70. Xu, B.-H.; Wang, J.-Q.; Sun, J.; Huang, Y.; Zhang, J.-P.; Zhang, X.-P.; Zhang, S.-J. Fixation of CO2 into cyclic carbonates catalyzed by ionic liquids: a multi-scale approach Green Chem. 2015, 17, 108-122 10.1039/C4GC01754D
71. Carothers, W. H.; Natta, F. J. V. Studies of Polymerization and Ring Formation. III. Glycol esters of carbonic acid J. Am. Chem. Soc. 1930, 52, 314-326 10.1021/ja01364a045
72. Hill, J. W.; Carothers, W. H. Studies of Polymerization and Ring Formation. XX. Many-Membered Cyclic Esters J. Am. Chem. Soc. 1933, 55, 5031-5039 10.1021/ja01339a055
73. Hill, J. W.; Carothers, W. H. Studies of Polymerization and Ring Formation. XXI. Physical Properties of Macrocyclic Esters and Anhydrides. New Types of Synthetic Musks J. Am. Chem. Soc. 1933, 55, 5039-5043 10.1021/ja01339a056
74. Spanagel, E. W.; Carothers, W. H. Macrocyclic esters J. Am. Chem. Soc. 1935, 57, 929-934 10.1021/ja01308a046
75. Nemirowsky, J. Ueber die Einwirkung von Chlorkohlenoxyd auf Aethylenglycol; vorläufige Mittheilung J. Prakt. Chem. 1883, 28, 439-440 10.1002/prac.18830280136
76. Burk, R. M.; Roof, M. B. A safe and efficient method for conversion of 1,2- and 1,3-diols to cyclic carbonates utilizing triphosgene Tetrahedron Lett. 1993, 34, 395-398 10.1016/0040-4039(93)85085-B
77. Tomita, H.; Sanda, F.; Endo, T. Reactivity comparison of five- and six-membered cyclic carbonates with amines: Basic evaluation for synthesis of poly(hydroxyurethane) J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 162-168 10.1002/1099-0518(20010101)39:1162::AID-POLA1803.0.CO;2-O
78. Caló, V.; Nacci, A.; Monopoli, A.; Fanizzi, A. Cyclic Carbonate Formation from Carbon Dioxide and Oxiranes in Tetrabutylammonium Halides as Solvents and Catalysts Org. Lett. 2002, 4, 2561-2563 10.1021/ol026189w
79. Huang, S.-y.; Liu, S.-g.; Li, J.-p.; Zhao, N.; Wei, W.; Sun, Y.-h. Synthesis of cyclic carbonate from carbon dioxide and diols over metal acetates J. Fuel Chem. Technol. 2007, 35, 701-705 10.1016/S1872-5813(08)60005-5
80. Wang, H.; Wu, L.-X.; Lan, Y.-C.; Zhao, J.-Q.; Lu, J.-X. Electrosynthesis of Cyclic Carbonates From CO2 and Diols in Ionic Liquids Under Mild Conditions Int. J. Electrochem. Sci. 2011, 6, 4218-4227
81. Wang, H.; Wu, L.-X.; Zhao, J.-Q.; Li, R.-N.; Zhang, A.-J.; Kajiura, H.; Li, Y.-M.; Lu, J.-X. Synthesis of cyclic carbonates from CO2 and diols via electrogenerated cyanomethyl anion Greenhouse Gases: Sci. Technol. 2012, 2, 59-65 10.1002/ghg.42
82. Gabriele, B.; Mancuso, R.; Salerno, G.; Ruffolo, G.; Costa, M.; Dibenedetto, A. A novel and efficient method for the catalytic direct oxidative carbonylation of 1,2- and 1,3-diols to 5-membered and 6-membered cyclic carbonates Tetrahedron Lett. 2009, 50, 7330-7332 10.1016/j.tetlet.2009.10.054
83. Pearson, D. M.; Conley, N. R.; Waymouth, R. M. Palladium-Catalyzed Carbonylation of Diols to Cyclic Carbonates Adv. Synth. Catal. 2011, 353, 3007-3013 10.1002/adsc.201100240
84. Aresta, M.; Dibenedetto, A.; Dileo, C.; Tommasi, I.; Amodio, E. The first synthesis of a cyclic carbonate from a ketal in SC-CO2 J. Supercrit. Fluids 2003, 25, 177-182 10.1016/S0896-8446(02)00095-5
85. Komura, H.; Yoshino, T.; Ishido, Y. Synthetic Studies by the Use of Carbonates, II. An Easy Method of Preparing Cyclic Carbonates of Polyhydroxy Compounds by Transesterification with Ethylene Carbonate Bull. Chem. Soc. Jpn. 1973, 46, 550-553 10.1246/bcsj.46.550
86. Yeo, I.-S.; Woo, B.-W.; Yoon, S.-W.; Lee, J.-H.; Park, S.-H.; Jang, N.-J. U.S. Patent US20100048918, 2010.
87. Chem. Abstr. 2010, 152, 288039.
88. Takagaki, A.; Iwatani, K.; Nishimura, S.; Ebitani, K. Synthesis of glycerol carbonate from glycerol and dialkyl carbonates using hydrotalcite as a reusable heterogeneous base catalyst Green Chem. 2010, 12, 578-581 10.1039/b925404h
89. Mouloungui, Z.; Yoo, J.-W.; Gachen, C.-A.; Gaset, A.; Vermeersch, G. Eurepean Patent EP739888, 1996.
90. Chem. Abstr. 1996, 126, 19166.
91. Mignani, G.; Debray, J.; Da Silva, E.; Lemaire, M.; Raoul, Y. World Patent WO2014009421, 2013.
92. Chem. Abstr. 2013, 160, 219197.
93. Su, W.-Y.; Speranza, G. P. U.S. Patent US5003084, 1991.
94. Chem. Abstr. 1991, 114, 247258.
95. Bhanage, B. M.; Fujita, S.-i.; Ikushima, Y.; Arai, M. Transesterification of urea and ethylene glycol to ethylene carbonate as an important step for urea based dimethyl carbonate synthesis Green Chem. 2003, 5, 429-432 10.1039/b304182d
96. Lim, Y. N.; Lee, C.; Jang, H.-Y. Metal-Free Synthesis of Cyclic and Acyclic Carbonates from CO2 and Alcohols Eur. J. Org. Chem. 2014, 2014, 1823-1826 10.1002/ejoc.201400031
97. Whelan, J. M. U.S. Patent US2935494, 1960.
98. Chem. Abstr. 1960, 54, 94907.
99. Reithofer, M. R.; Sum, Y. N.; Zhang, Y. Synthesis of Cyclic Carbonates with Carbon Dioxide and Cesium Carbonate Green Chem. 2013, 15, 2086-2090 10.1039/c3gc40790j
100. Sun, J.; Liang, L.; Jiang, Y.; Lin, K.; Xu, X.; Wang, R.; Sun, J. Direct Synthetic Processes for Cyclic Carbonates from Olefins and CO2 Catal. Surv. Asia 2011, 15, 49-54 10.1007/s10563-010-9106-4
101. Chen, F.; Dong, T.; Xu, T.; Li, X.; Hu, C. Direct synthesis of cyclic carbonates from olefins and CO2 catalyzed by a MoO2(acac)2-quaternary ammonium salt system Green Chem. 2011, 13, 2518-2524 10.1039/c1gc15549k
102. Ca, N. D.; Gabriele, B.; Ruffolo, G.; Veltri, L.; Zanetta, T.; Costa, M. Effective Guanidine-Catalyzed Synthesis of Carbonate and Carbamate Derivatives from Propargyl Alcohols in Supercritical Carbon Dioxide Adv. Synth. Catal. 2011, 353, 133-146 10.1002/adsc.201000607
103. Bruneau, C.; Dixneuf, P. H. Catalytic incorporation of CO2 into organic substrates: Synthesis of unsaturated carbamates, carbonates and ureas J. Mol. Catal. 1992, 74, 97-107 10.1016/0304-5102(92)80227-8
104. Renga, J. M.; Periana-Pillai, R. A. U.S. Patent US4332729, 1982.
105. Chem. Abstr. 1982, 97, 127627.
106. Pews, R. G. Synthesis of Cyclic Carbonates by a Novel Carbonate Rearrangement J. Chem. Soc., Chem. Commun. 1974, 4, 119a 10.1039/c3974000119a
107. Nishikubo, T.; Iizawa, T.; Iida, M.; Isobe, N. Convenient syntheses of cyclic carbonates by new reaction of oxiranes with β-butyrolactone Tetrahedron Lett. 1986, 27, 3741-3744 10.1016/S0040-4039(00)83868-X
108. Olah, G. A.; Prakash, G. K. S.; Goeppert, A. Anthropogenic Chemical Carbon Cycle for a Sustainable Future J. Am. Chem. Soc. 2011, 133, 12881-12898 10.1021/ja202642y
109. Beckman, E. J. Supercritical and near-critical CO2 in green chemical synthesis and processing J. Supercrit. Fluids 2004, 28, 121-191 10.1016/S0896-8446(03)00029-9
110. Dai, W.-L.; Luo, S.-L.; Yin, S.-F.; Au, C.-T. The direct transformation of carbon dioxide to organic carbonates over heterogeneous catalysts Appl. Catal., A 2009, 366, 2-12 10.1016/j.apcata.2009.06.045
111. Sun, J.; Fujita, S.-i.; Arai, M. Development in the green synthesis of cyclic carbonate from carbon dioxide using ionic liquids J. Organomet. Chem. 2005, 690, 3490-3497 10.1016/j.jorganchem.2005.02.011
112. North, M.; Pasquale, R.; Young, C. Synthesis of cyclic carbonates from epoxides and CO2 Green Chem. 2010, 12, 1514-1539 10.1039/c0gc00065e
113. Yang, X.; Wu, J.; Mao, X.; Jamison, T. F.; Hatton, T. A. Microwave assisted synthesis of cyclic carbonates from olefins with sodium bicarbonates as the C1 source Chem. Commun. 2014, 50, 3245-3248 10.1039/c4cc00252k
114. Tomita, H.; Sanda, F.; Endo, T. Polyaddition of bis(seven-membered cyclic carbonate) with diamines: A novel and efficient synthetic method for polyhydroxyurethanes J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 4091-4100 10.1002/pola.10058
115. Sarel, S.; Pohoryles, L. A. The Stereochemistry and Mechanism of Reversible Polymerization of 2,2-Disubstituted 1,3-Propanediol Carbonates J. Am. Chem. Soc. 1958, 80, 4596-4599 10.1021/ja01550a044
116. Hu, B.; Zhuo, R.; Fan, C. Synthesis of copolymer of 1,3-dioxan-2-one and 2-hydro-2-oxo-1,3,2-dioxaphosphorinane Polym. Adv. Technol. 1998, 9, 145-149 10.1002/(SICI)1099-1581(199802)9:2145::AID-PAT7423.0.CO;2-C
117. Clements, J.; Klein, H.; Marquis, T. World Patent WO089424, 2003.
118. Chem. Abstr. 2003, 148, 169160.
119. Albertson, A. C.; Ann, C.; Sjoling, M. Homopolymerization of 1,3-dioxan-2-one to high-molecular-weight poly(trimethylene carbonate) J. Macromol. Sci., Part A: Pure Appl.Chem. 1992, 29, 43-54 10.1080/10101329208054106
120. Clements, J. H. Reactive Applications of Cyclic Alkylene Carbonates Ind. Eng. Chem. Res. 2003, 42, 663-674 10.1021/ie020678i
121. Pyo, S.-H.; Persson, P.; Lundmark, S.; Hatti-Kaul, R. Solvent-free lipase-mediated synthesis of six-membered cyclic carbonates from trimethylolpropane and dialkyl carbonates Green Chem. 2011, 13, 976-982 10.1039/c0gc00783h
122. Pyo, S.-H.; Hatti-Kaul, R. Selective, Green Synthesis of Six-Membered Cyclic Carbonates by Lipase-Catalyzed Chemospecific Transesterification of Diols with Dimethyl Carbonate Adv. Synth. Catal. 2012, 354, 797-802 10.1002/adsc.201100822
123. Nohra, B.; Candy, L.; Blanco, J.-F.; Raoul, Y.; Mouloungui, Z. Synthesis of Five and Six-membered Cyclic Glycerilic Carbonates bearing Exocyclic Urethane Functions Eur. J. Lipid Sci. Technol. 2013, 115, 111-122 10.1002/ejlt.201200082
124. Honda, M.; Tamura, M.; Nakao, K.; Suzuki, K.; Nakagawa, Y.; Tomishige, K. Direct Cyclic Carbonate Synthesis from CO2 and Diol over Carboxylation/Hydration Cascade Catalyst of CeO2 with 2-Cyanopyridine ACS Catal. 2014, 4, 1893-1896 10.1021/cs500301d
125. Baba, A.; Kashiwagi, H.; Matsuda, H. Cycloaddition of oxetane and carbon dioxide catalyzed by tetraphenylstibonium iodide Tetrahedron Lett. 1985, 26, 1323-1324 10.1016/S0040-4039(00)94883-4
126. Darensbourg, D. J.; Moncada, A. I. Tuning the Selectivity of the Oxetane and CO2 Coupling Process Catalyzed by (Salen)CrCl/n-Bu4NX: Cyclic Carbonate Formation vs Aliphatic Polycarbonate Production Macromolecules 2010, 43, 5996-6003 10.1021/ma100896x
127. Besse, V.; Foyer, G.; Auvergne, R.; Caillol, S.; Boutevin, B. Access to nonisocyanate poly(thio)urethanes: A comparative study J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 3284-3296 10.1002/pola.26722
128. Benyahya, S.; Habas, J.-P.; Auvergne, R.; Lapinte, V.; Caillol, S. Structure-property relationships in polyhydroxyurethanes produced from terephthaloyl dicyclocarbonate with various polyamines Polym. Int. 2012, 61, 1666-1674 10.1002/pi.4257
129. Carré, C.; Bonnet, L.; Averous, L. Original biobased nonisocyanate polyurethanes: Solvent- and catalyst-free synthesis, thermal properties and rheological behaviour RSC Adv. 2014, 4, 54018-54025 10.1039/C4RA09794G
130. Helou, M.; Carpentier, J.-F.; Guillaume, S. M. Poly(carbonate-urethane): an isocyanate-free procedure from [small alpha],[small omega]-di(cyclic carbonate) telechelic poly(trimethylene carbonate)s Green Chem. 2011, 13, 266-271 10.1039/C0GC00686F
131. Benyahya, S.; Desroches, M.; Auvergne, R.; Carlotti, S.; Caillol, S.; Boutevin, B. Synthesis of glycerin carbonate-based intermediates using thiol-ene chemistry and isocyanate free polyhydroxyurethanes therefrom Polym. Chem. 2011, 2, 2661-2667 10.1039/c1py00289a
132. Tang, C. N.; Nulwala, H. B.; Damodaran, K.; Kaur, P.; Luebke, D. R. Tunable poly(hydroxyl urethane) from CO2-Based intermediates using thiol-ene chemistry J. Polym. Sci., Part A: Polym. Chem. 2011, 49, 2024-2032 10.1002/pola.24631
133. Kihara, N.; Endo, T. Synthesis and properties of poly(hydroxyurethane)s J. Polym. Sci., Part A: Polym. Chem. 1993, 31, 2765-2773 10.1002/pola.1993.080311113
134. Steblyanko, A.; Choi, W.; Sanda, F.; Endo, T. Addition of five-membered cyclic carbonate with amine and its application to polymer synthesis J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 2375-2380 10.1002/1099-0518(20000701)38:132375::AID-POLA1003.0.CO;2-U
135. Kim, M.-R.; Kim, H.-S.; Ha, C.-S.; Park, D.-W.; Lee, J.-K. Syntheses and thermal properties of poly(hydroxy)urethanes by polyaddition reaction of bis(cyclic carbonate) and diamines J. Appl. Polym. Sci. 2001, 81, 2735-2743 10.1002/app.1719
136. Brocas, A.-L.; Cendejas, G.; Caillol, S.; Deffieux, A.; Carlotti, S. Controlled synthesis of polyepichlorohydrin with pendant cyclic carbonate functions for isocyanate-free polyurethane networks J. Polym. Sci., Part A: Polym. Chem. 2011, 49, 2677-2684 10.1002/pola.24699
137. Sprott, K. T.; Corey, E. J. A New Cationic, Chiral Catalyst for Highly Enantioselective Diels-Alder Reactions Org. Lett. 2003, 5, 2465-2467 10.1021/ol034706k
138. Rannard, S. P.; Davis, N. J. Controlled Synthesis of Asymmetric Dialkyl and Cyclic Carbonates Using the Highly Selective Reactions of Imidazole Carboxylic Esters Org. Lett. 1999, 1, 933-936 10.1021/ol9908528
139. Vriet, C. Généralisation de la carbonatation aux substrats polyhydroxylés. Synthèse de carbonates cycliques, linéaires, et mixtes, à partir d'érythritol, de xylitol, et de sorbitol; PhD Thesis, Institut National Polytechnique de Toulouse: Toulouse, France, 2005.
140. Fache, M.; Darroman, E.; Besse, V.; Auvergne, R.; Caillol, S.; Boutevin, B. Vanillin, a promising biobased building-block for monomer synthesis Green Chem. 2014, 16, 1987-1998 10.1039/c3gc42613k
141. Tomita, H.; Sanda, F.; Endo, T. Model reaction for the synthesis of polyhydroxyurethanes from cyclic carbonates with amines: Substituent effect on the reactivity and selectivity of ring-opening direction in the reaction of five-membered cyclic carbonates with amine J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 3678-3685 10.1002/pola.10009
142. Garipov, R. M.; Sysoev, V. A.; Mikheev, V. V.; Zagidullin, A. I.; Deberdeev, R. Y.; Irzhak, V. I.; Berlin, A. A. Reactivity of Cyclocarbonate Groups in Modified Epoxy-Amine Compositions Dokl. Phys. Chem. 2003, 393, 289-292 10.1023/B:DOPC.0000003463.07883.c9
143. Garipov, R. M.; Mikheev, V. V.; Deberdeev, T. R.; Irzhak, V. I.; Berlin, A. A. Study of the Curing Kinetics for Modified Epoxy Amine Systems Using Model Compounds Dokl. Phys. Chem. 2003, 392, 268-271 10.1023/A:1026190529702
144. Zabalov, M. V.; Tiger, R. P.; Berlin, A. A. Mechanism of urethane formation from cyclocarbonates and amines: a quantum chemical study Russ. Chem. Bull. 2012, 61, 518-527 10.1007/s11172-012-0076-8
145. Bürgel, T.; Fedtke, M. Epoxy resins with cyclic carbonate structures Polym. Bull. 1993, 30, 61-68
146. Bürgel, T.; Fedtke, M. Epoxy resins with cyclic carbonate structures Polym. Bull. 1993, 30, 61-68 10.1007/BF00296235
147. Tomita, H.; Sanda, F.; Endo, T. Structural analysis of polyhydroxyurethane obtained by polyaddition of bifunctional five-membered cyclic carbonate and diamine based on the model reaction J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 851-859 10.1002/1099-0518(20010315)39:6851::AID-POLA10583.0.CO;2-3
148. Couvret, D.; Brosse, J.-C.; Chevalier, S.; Senet, J.-P. Monomères acryliques à fonction carbonate cyclique, 2 Modification chimique de copolymères à groupements carbonate cyclique lateraux Makromol. Chem. 1990, 191, 1311-1319 10.1002/macp.1990.021910610
149. Nemirovsky, V. C.; Skorokhodov, S. S. Kinetic Study of Aminolysis of Poly(vinylene Carbonate) and Related Model Compounds J. Polym. Sci., Part C: Polym. Symp. 1967, 16, 1471-1478 10.1002/polc.5070160324
150. Bürgel, T.; Fedtke, M. Reactions of cyclic carbonates with amines: Model studies for curing process Polym. Bull. 1991, 27, 171-177 10.1007/BF00296027
151. Ochiai, B.; Matsuki, M.; Miyagawa, T.; Nagai, D.; Endo, T. Kinetic and computational studies on aminolysis of bicyclic carbonates bearing alicyclic structure giving alicyclic hydroxyurethanes Tetrahedron 2005, 61, 1835-1838 10.1016/j.tet.2004.12.014
152. He, Y.; Goel, V.; Keul, H.; Möller, M. Synthesis, Characterization, and Selectivity of Bifunctional Couplers Macromol. Chem. Phys. 2010, 211, 2366-2381 10.1002/macp.201000340
153. Blain, M.; Jean-Gerard, L.; Auvergne, R.; Benazet, D.; Caillol, S.; Andrioletti, B. Rational investigations in the ring opening of cyclic carbonates by amines Green Chem. 2014, 16, 4286-4291 10.1039/C4GC01032A
154. Maisonneuve, L.; Wirotius, A.-L.; Alfos, C.; Grau, E.; Cramail, H. Fatty acid-based (bis) 6-membered cyclic carbonates as efficient isocyanate free poly(hydroxyurethane) precursors Polym. Chem. 2014, 5, 6142-6147 10.1039/C4PY00922C
155. Nohra, B.; Candy, L.; Blanco, J.-F.; Raoul, Y.; Mouloungui, Z. Aminolysis Reaction of Glycerol Carbonate in Organic and Hydroorganic Medium J. Am. Oil Chem. Soc. 2012, 89, 1125-1133 10.1007/s11746-011-1995-5
156. Iwasaki, T.; Kihara, N.; Endo, T. Reaction of Various Oxiranes and Carbon Dioxide. Synthesis and Aminolysis of Five-Membered Cyclic Carbonates Bull. Chem. Soc. Jpn. 2000, 73, 713-719 10.1246/bcsj.73.713
157. Ochiai, B.; Koda, K.; Endo, T. Branched cationic polyurethane prepared by polyaddition of chloromethylated five-membered cyclic carbonate and diethylenetriamine in molten salts J. Polym. Sci., Part A: Polym. Chem. 2012, 50, 47-51 10.1002/pola.24969
158. Rokicki, G.; Aaziński, R. Polyamines containing β-hydroxyurethane linkages as curing agents for epoxy resin Angew. Makromol. Chem. 1989, 170, 211-225 10.1002/apmc.1989.051700117
159. Camara, F.; Benyahya, S.; Besse, V.; Boutevin, G.; Auvergne, R.; Boutevin, B.; Caillol, S. Reactivity of secondary amines for the synthesis of non-isocyanate polyurethanes Eur. Polym. J. 2014, 55, 17-26 10.1016/j.eurpolymj.2014.03.011
160. Diakoumakos, C. D.; Kotzev, D. L. Non-Isocyanate-Based Polyurethanes Derived upon the Reaction of Amines with Cyclocarbonate Resins Macromol. Symp. 2004, 216, 37-46 10.1002/masy.200451205
161. Webster, D. C.; Crain, A. L. Synthesis and applications of cyclic carbonate functional polymers in thermosetting coatings Prog. Org. Coat. 2000, 40, 275-282 10.1016/S0300-9440(00)00114-4
162. He, Y.; Keul, H.; Möller, M. Synthesis, characterization, and application of a bifunctional coupler containing a five- and a six-membered ring carbonate React. Funct. Polym. 2011, 71, 175-186 10.1016/j.reactfunctpolym.2010.11.031
163. Honel, M.; Sprenger, W.; Wendt, W.; Ziegler, P. U.S. Patent US5055542, 1991.
164. Chem. Abstr. 1991, 113, 193529.
165. Honel, M.; Ziegler, P.; Foedde, H. U.S. Patent US5132458, 1992.
166. Chem. Abstr. 1992, 111, 800018.
167. Fleischer, M.; Blattmann, H.; Mulhaupt, R. Glycerol-, pentaerythritol- and trimethylolpropane-based polyurethanes and their cellulose carbonate composites prepared via the non-isocyanate route with catalytic carbon dioxide fixation Green Chem. 2013, 15, 934-942 10.1039/c3gc00078h
168. Lambeth, R. H.; Henderson, T. J. Organocatalytic Synthesis of (Poly)hydroxyurethanes from Cyclic Carbonates and Amines Polymer 2013, 54, 5568-5573 10.1016/j.polymer.2013.08.053
169. Anderson, A. G. U.S. Patent US5977262, 1999.
170. Chem. Abstr. 1999, 129, 315972.
171. Holen, J. V. U.S. Patent US20040236119, 2004.
172. Chem. Abstr. 2004, 141, 366216.
173. Holen, J. V. U.S. Patent US20050113594, 2005.
174. Chem. Abstr. 2005, 139, 180490.
175. Ochiai, B.; Inoue, S.; Endo, T. Salt effect on polyaddition of bifunctional cyclic carbonate and diamine J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 6282-6286 10.1002/pola.21081
176. Gurgiolo, A. E. U.S. Patent US4268684, 1981.
177. Chem. Abstr. 1981, 95, 97407.
178. Soules, A.; Caillol, S.; Joubert, J.-P.; Martins, J.; Boutevin, B. World Patent WO2013060950, 2013.
179. Chem. Abstr. 2013, 158, 622519.
180. Diakoumakos, C. D.; Kotzev, D. L. World Patent WO2005016993, 2005.
181. Chem. Abstr. 2005, 142, 622519.
182. Ochiai, B.; Inoue, S.; Endo, T. One-pot non-isocyanate synthesis of polyurethanes from bisepoxide, carbon dioxide, and diamine J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 6613-6618 10.1002/pola.21103
183. Maisonneuve, L.; More, A. S.; Foltran, S.; Alfos, C.; Robert, F.; Landais, Y.; Tassaing, T.; Grau, E.; Cramail, H. Novel green fatty acid-based bis-cyclic carbonates for the synthesis of isocyanate-free poly(hydroxyurethane amide)s RSC Adv. 2014, 4, 25795-25803 10.1039/c4ra03675a
184. Lombardo, V. M.; Dhulst, E. A.; Leitsch, E. K.; Wilmot, N.; Heath, W. H.; Gies, A. P.; Miller, M. D.; Torkelson, J. M.; Scheidt, K. A. Cooperative Catalysis of Cyclic Carbonate Ring Opening: Application Towards Non-Isocyanate Polyurethane Materials Eur. J. Org. Chem. 2015, 2015, 2791-2795 10.1002/ejoc.201500313
185. Bürgel, T.; Fedtke, M.; Franzke, M. Reaction of cyclic carbonates with amines: Linear telechelic oligomers Polym. Bull. 1993, 30, 155-162 10.1007/BF00296844
186. Kihara, N.; Kushida, Y.; Endo, T. Optically active poly(hydroxyurethane)s derived from cyclic carbonate and L-lysine derivatives J. Polym. Sci., Part A: Polym. Chem. 1996, 34, 2173-2179 10.1002/(SICI)1099-0518(199608)34:112173::AID-POLA103.0.CO;2-C
187. Tomita, H.; Sanda, F.; Endo, T. Self-Polyaddition of Six-Membered Cyclic Carbonate Having Fmoc-Protected Amino Group: Novel Synthetic Method of Polyhydroxyurethane Macromolecules 2001, 34, 7601-7607 10.1021/ma010622k
188. Ochiai, B.; Satoh, Y.; Endo, T. Nucleophilic polyaddition in water based on chemo-selective reaction of cyclic carbonate with amine Green Chem. 2005, 7, 765-767 10.1039/b511019j
189. Ochiai, B.; Sato, S.-I.; Endo, T. Synthesis and properties of polyurethanes bearing urethane moieties in the side chain J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 3408-3414 10.1002/pola.22093
190. Ochiai, B.; Satoh, Y.; Endo, T. Polyaddition of bifunctional cyclic carbonate with diamine in ionic liquids: In situ ion composite formation and simple separation of ionic liquid J. Polym. Sci., Part A: Polym. Chem. 2009, 47, 4629-4635 10.1002/pola.23514
191. Benyahya, S.; Boutevin, B.; Caillol, S.; Lapinte, V.; Habas, J.-P. Optimization of the synthesis of polyhydroxyurethanes using dynamic rheometry Polym. Int. 2012, 61, 918-925 10.1002/pi.4159
192. Hwang, J.-Z.; Chen, C.-L.; Huang, C.-Y.; Yeh, J.-T.; Chen, K.-N. Green PU resin from an accelerated Non-isocyanate process with microwave radiation J. Polym. Res. 2013, 20, 1-10 10.1007/s10965-013-0195-4
193. Lambeth, R. H.; Henderson, T. J. Organocatalytic synthesis of (poly)hydroxyurethanes from cyclic carbonates and amines Polymer 2013, 54, 5568-5573 10.1016/j.polymer.2013.08.053
194. Ochiai, B.; Kojima, H.; Endo, T. Synthesis and properties of polyhydroxyurethane bearing silicone backbone J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 1113-1118 10.1002/pola.27091
195. Sheng, X.; Ren, G.; Qin, Y.; Chen, X.; Wang, X.; Wang, F. Quantitative synthesis of bis(cyclic carbonate)s by iron catalyst for non-isocyanate polyurethane synthesis Green Chem. 2015, 17, 373-379 10.1039/C4GC01294A
196. Matsukizono, H.; Endo, T. Synthesis of polyhydroxyurethanes from di(trimethylolpropane) and their application to quaternary ammonium chloride-functionalized films RSC Adv. 2015, 5, 71360-71369 10.1039/C5RA09885H
197. Ubaghs, L.; Fricke, N.; Keul, H.; Höcker, H. Polyurethanes with Pendant Hydroxyl Groups: Synthesis and Characterization Macromol. Rapid Commun. 2004, 25, 517-521 10.1002/marc.200300064
198. Carpentier, J.-F.; Guillaume, S.; Helou, M.; Slawinski, M. World Patent WO2012007254, 2012.
199. Chem. Abstr. 2012, 156, 176183.
200. Annunziata, L.; Diallo, A. K.; Fouquay, S.; Michaud, G.; Simon, F.; Brusson, J.-M.; Carpentier, J.-F.; Guillaume, S. M. [small alpha],[small omega]-Di(glycerol carbonate) telechelic polyesters and polyolefins as precursors to polyhydroxyurethanes: an isocyanate-free approach Green Chem. 2014, 16, 1947-1956 10.1039/C3GC41821A
201. Besse, V.; Camara, F.; Méchin, F.; Fleury, E.; Caillol, S.; Pascault, J.-P.; Boutevin, B. How to explain low molar masses in PolyHydroxyUrethanes (PHUs) Eur. Polym. J. 2015, 71, 1-11 10.1016/j.eurpolymj.2015.07.020
202. Keul, H.; Mommer, S.; Möller, M. Poly(amide urethane)s with functional/reactive side groups based on a bis-cyclic bio-based monomer/coupling agent Eur. Polym. J. 2013, 49, 853-864 10.1016/j.eurpolymj.2012.10.024
203. Proempers, G.; Keul, H.; Hoecker, H. Polyurethanes with pendant hydroxy groups: Polycondensation of D-mannitol-1,2:5,6-dicarbonate with diamines Des. Monomers Polym. 2005, 8, 547-569 10.1163/156855505774597830
204. Bahr, M.; Bitto, A.; Mülhaupt, R. Cyclic limonene dicarbonate as new monomer for non-isocyanate oligo- and polyurethanes (NIPU) based upon terpenes Green Chem. 2012, 14, 1447-1454 10.1039/c2gc35099h
205. Besse, V.; Auvergne, R.; Carlotti, S.; Boutevin, G.; Otazaghine, B.; Caillol, S.; Pascault, J.-P.; Boutevin, B. Synthesis of isosorbide based polyurethanes: An isocyanate free method React. Funct. Polym. 2013, 73, 588-594 10.1016/j.reactfunctpolym.2013.01.002
206. Boyer, A.; Cloutet, E.; Tassaing, T.; Gadenne, B.; Alfos, C.; Cramail, H. Solubility in CO2 and carbonation studies of epoxidized fatty acid diesters: towards novel precursors for polyurethane synthesis Green Chem. 2010, 12, 2205-2213 10.1039/c0gc00371a
207. Chen, Q.; Gao, K.; Peng, C.; Xie, H.; Zhao, Z. K.; Bao, M. Preparation of lignin/glycerol-based bis(cyclic carbonate) for the synthesis of polyurethanes Green Chem. 2015, 17, 4546-4551 10.1039/C5GC01340B
208. van Velthoven, J. L. J.; Gootjes, L.; van Es, D. S.; Noordover, B. A. J.; Meuldijk, J. Poly(hydroxy urethane)s based on renewable diglycerol dicarbonate Eur. Polym. J. 2015, 70, 125-135 10.1016/j.eurpolymj.2015.07.011
209. Fricke, N.; Keul, H.; Möller, M. Carbonate Couplers and Functional Cyclic Carbonates from Amino Acids and Glucosamine Macromol. Chem. Phys. 2009, 210, 242-255 10.1002/macp.200800497
210. Moriguchi, T.; Endo, T. Polyaddition of Bifunctional Dithiocarbonates Derived from Epoxides and Carbon Disulfide. Synthesis of Novel Poly(thiourethanes) Macromolecules 1995, 28, 5386-5387 10.1021/ma00119a035
211. Gilbeau, P. World Patent WO2006100311, 2006.
212. Chem. Abstr. 2006, 145, 357239.
213. Foltran, S.; Maisonneuve, L.; Cloutet, E.; Gadenne, B.; Alfos, C.; Tassaing, T.; Cramail, H. Solubility in CO2 and swelling studies by in situ IR spectroscopy of vegetable-based epoxidized oils as polyurethane precursors Polym. Chem. 2012, 3, 525-532 10.1039/C2PY00476C
214. Cramail, H.; Boyer, A.; Cloutet, E.; Gadenne, B.; Alfos, C. World Patent WO2011061452, 2011.
215. Chem. Abstr. 2011, 154, 591358.
216. Desroches, M.; Benyahya, S.; Besse, V.; Auvergne, R.; Boutevin, B.; Caillol, S. Synthesis of bio-based building blocks from vegetable oils: A platform chemicals approach Lipid Technol. 2014, 26, 35-38 10.1002/lite.201400014
217. Turunc, O.; Firdaus, M.; Klein, G.; Meier, M. A. R. Fatty acid derived renewable polyamides via thiol-ene additions Green Chem. 2012, 14, 2577-2583 10.1039/c2gc35982k
218. Harry-O'kuru, R. E.; Gordon, S. H.; Biswas, A. A facile synthesis of aminohydroxy triglycerides from new crop oils J. Am. Oil Chem. Soc. 2005, 82, 207-212 10.1007/s11746-005-1058-5
219. Miao, X.; Malacea, R.; Fischmeister, C.; Bruneau, C.; Dixneuf, P. H. Ruthenium-alkylidene catalysed cross-metathesis of fatty acid derivatives with acrylonitrile and methyl acrylate: a key step toward long-chain bifunctional and amino acid compounds Green Chem. 2011, 13, 2911-2919 10.1039/c1gc15569e
220. Miao, X.; Fischmeister, C.; Dixneuf, P. H.; Bruneau, C.; Dubois, J. L.; Couturier, J. L. Polyamide precursors from renewable 10-undecenenitrile and methyl acrylate via olefin cross-metathesis Green Chem. 2012, 14, 2179-2183 10.1039/c2gc35648a
221. He, J.; Samanta, S.; Selvakumar, S.; Lattimer, J.; Ulven, C.; Sibi, M.; Bahr, J.; Chisholm, B. J. Green Mater. 2013, 1, 114-124
222. Stempfle, F.; Quinzler, D.; Heckler, I.; Mecking, S. Long-Chain Linear C19 and C23 Monomers and Polycondensates from Unsaturated Fatty Acid Esters Macromolecules 2011, 44, 4159-4166 10.1021/ma200627e
223. Winkler, M.; Meier, M. A. R. Highly efficient oxyfunctionalization of unsaturated fatty acid esters: an attractive route for the synthesis of polyamides from renewable resources Green Chem. 2014, 16, 1784-1788 10.1039/C3GC41921E
224. Baumann, H.; Bühler, M.; Fochem, H.; Hirsinger, F.; Zoebelein, H.; Falbe, J. Natural Fats and Oils-Renewable Raw Materials for the Chemical Industry Angew. Chem., Int. Ed. Engl. 1988, 27, 41-62 10.1002/anie.198800411
225. Genas, M. Rilsan (Polyamid 11), Synthese und Eigenschaften Angew. Chem. 1962, 74, 535-540 10.1002/ange.19620741504
226. Ogunniyi, D. S. Castor oil: A vital industrial raw material Bioresour. Technol. 2006, 97, 1086-1091 10.1016/j.biortech.2005.03.028
227. Darroman, E.; Balbusquier, C.; Caillol, S.; Boutevin, B.; Auvergne, R.; Loisel, C.; Tourneix, D. World Patent WO2015107113, 2015, Chem. Abstr. 2015, 163, 219043.
228. Hsueh, M.-L.; Chen, Y.-Z.; Yeh, C.-W.; Liu, C.-W.; Hsieh, F.-M.; Shih, H.-H.; Shih, K.-C. European Patent EP2889359, 2015.
229. Chem. Abstr. 2015, 163, 147958.
230. EPA, 2015 Designing Greener Chemicals Award. http://www2.epa.gov/greenchemistry/2015-designing-greener-chemicals-award (accessed: July 24, 2015).
231. Trub, E.; Sonnati, M.; Choulet, O. World Patent WO2012130998, 2012.
232. Chem. Abstr. 2012, 157, 522588.