Renewable non-isocyanate based thermoplastic polyurethanes via polycondensation of dimethyl carbamate monomers with diols

Macromolecular Rapid Communications

Volumn 34, Issue 19, 2013, Pages 1569-1574

  Unverferth, Maike ^a   Kreye, Oliver ^a   Prohammer, Alexander ^a   Meier, Michael A R ^a  

^a KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

Author keywords

fatty acids; non isocyanate polyurethanes; polycondensation; polyurethanes; renewable resources

Indexed keywords

1 ,5 ,7-TRIAZABICYCLO[4.4.0]DEC-5-ENE; DICARBOXYLIC ACID; GREEN CHEMISTRY; MONOMER SYNTHESIS; NONISOCYANATE POLYURETHANE; POLYCONDENSATION REACTIONS; RENEWABLE RESOURCE; THERMOPLASTIC POLYURETHANES;

CATALYSIS; FATTY ACIDS; MOLECULAR WEIGHT; MONOMERS; POLYCONDENSATION; SYNTHESIS (CHEMICAL);

POLYURETHANES;

CARBAMIC ACID DERIVATIVE; DICARBOXYLIC ACID; FATTY ACID; ISOCYANIC ACID DERIVATIVE; POLYURETHAN; VEGETABLE OIL;

ARTICLE; CATALYSIS; CHEMISTRY; ESTERIFICATION; GREEN CHEMISTRY; NON-ISOCYANATE POLYURETHANES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYCONDENSATION; POLYMERIZATION; RENEWABLE RESOURCES;

FATTY ACIDS; NON-ISOCYANATE POLYURETHANES; POLYCONDENSATION; POLYURETHANES; RENEWABLE RESOURCES;

CARBAMATES; CATALYSIS; DICARBOXYLIC ACIDS; ESTERIFICATION; GREEN CHEMISTRY TECHNOLOGY; ISOCYANATES; MAGNETIC RESONANCE SPECTROSCOPY; PLANT OILS; POLYMERIZATION; POLYURETHANES;

EID: 84885314646     PISSN: 10221336     EISSN: 15213927     Source Type: Journal    
DOI: 10.1002/marc.201300503     Document Type: Article

References (55)

1. T. Thomson, Polyurethanes as Specialty Chemicals: Principles and Applications, CRC Press, Boca Raton, FL 2004.
2. K. C. Frisch, D. Klempner, in Comprehensive Polymer Science: The Synthesis, Characterization, Reaction & Application of Polymers, Vol. 5. (Eds:, G. Allen, J. C. Berington,), Pergamon Press, Oxford 1990.
3. a) H. Tomita, F. Sanda, T. Endo, J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 851
4. b) G. Rokicki, A. Piotrowska, Polymer 2002, 43, 2927
5. c) B. Tamami, S. Sohn, G. L. Wilkes, J. Appl. Polym. Sci. 2004, 92, 883
6. d) S. Foltran, L. Maisonneuve, E. Cloutet, B. Gadenne, C. Alfos, T. Tassaing, H. Cramail, Polym. Chem. 2012, 3, 525
7. e) M. Bähr, A. Bitto, R. Mülhaupt, Green Chem. 2012, 14, 1447
8. f) S. J. Grozos, E. K. Drechsel, U.S. Pat. 2802022, 1957
9. g) C. Hahn, H. Keul, M. Möller, Polym. Int. 2012, 61, 1048
10. h) O. L. Figovsky, L. D. Shapovalov, Macromol. Symp. 2002, 187, 325
11. i) J. Guan, Y. H. Song, Y. Lin, X. Z. Yin, M. Zuo, Y. H. Zhao, X. L. Tao, Q. Zheng, Ind. Eng. Chem. Res. 2011, 50, 6517
12. j) Y. Yanagishita, M. Kato, K. Toshima, S. Matsumura, ChemSusChem 2008, 1, 133
13. k) E. Dyer, H. Scott, J. Am. Chem. Soc. 1957, 79, 672
14. l) B. Oichai, T. Utsuno, J. Polym. Sci., Part A: Polym. Chem. 2012, 51, 525
15. m) W. Blank, U.S. Patent 4820830 A, 1989
16. n) E. Hablot, D. Graiver, R. Narayan, PU Mag. Int. 2012, 255.
17. a) D. V. Palaskar, A. Boyer, E. Cloutet, C. Alfos, H. Cramail, Biomacromolecules 2010, 11, 1202
18. b) A. S. More, B. Gadenne, C. Alfos, H. Cramail, Polym. Chem. 2012, 3, 1594
19. c) A. S. More, T. Lebarbé, L. Maisonneuve, B. Gadenne, C. Alfos, H. Cramail, Eur. Polym. J. 2013, 49, 823
20. d) A. S. More, L. Maisonneuve, T. Lebarbé, B. Gadenne, C. Alfos, H. Cramail, Eur. J. Lipid Sci. Technol. 2013, 115, 61.
21. a) S. Neffgen, J. Kušan, T. Fey, H. Keul, H. Höcker, Macromol. Chem. Phys. 2000, 201, 2108
22. b) T. Baba, A. Kobayashi, T. Yamauchi, H. Tanaka, S. Aso, M. Inomata, Y. Kawanami, Catal. Lett. 2002, 82, 193
23. c) B. M. Bhanage, S. Fujita, Y. Ikushima, M. Arai, Green Chem. 2003, 5, 340
24. d) R. D. Lundberg, S. Albans, D. R. Montgomery, U.S. Pat. 3523924, 1970.
25. a) D. S. Ogunniyi, Bioresour. Technol. 2006, 97, 1086
26. b) H. Mutlu, M. A. R. Meier, Eur. J. Lipid Sci. Technol. 2010, 112, 10.
27. M. van Steen, C. V. Stevens, ChemSusChem 2009, 2, 692.
28. a) H. L. Ngo, K. Jones, T. A. Foglia, J. Am. Oil Chem. Soc. 2006, 83, 629
29. b) G. B. Djigoué, M. A. R. Meier, Appl. Catal., A 2009, 368, 158
30. c) M. A. R. Meier, Macromol. Chem. Phys. 2009, 210, 1073.
31. F. Gunstone, Fatty Acid and Lipid Chemistry, Chapmen & Hall, New York 1996.
32. a) P. Deepa, M. Jayakannan, J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 2445
33. b) P. Deepa, M. Jayakannan, J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 2351
34. c) H. Y. Chen, W. C. Pan, C. H. Lin, C. Y. Huang, S. A. Dai, J. Polym. Res. 2012, 19, 9754
35. d) M. Firdaus, M. A. R. Meier, Green Chem. 2013, 15, 370.
36. O. Kreye, H. Mutlu, M. A. R. Meier, Green Chem. 2013, 15, 1431.
37. D. Chaturvedi, Tetrahedron 2012, 68, 15.
38. a) H. L. Yale, Chem. Rev. 1943, 33, 209
39. b) L. Bauer, O. Exner, Angew. Chem Int. Ed. 1974, 13, 376.
40. a) B. Vasantha, H. P. Hemantha, V. V. Sureshbabu, Synthesis 2010, 2990
41. b) S. Pichette, S. Aubert-Nicol, J. Lessard, C. Spino, Eur. J. Org. Chem. 2012, 1328
42. c) L. Jašíková, E. Hanikýrová, A. Škríba, J. Jašík, J. Roithová, J. Org. Chem. 2012, 77, 2829.
43. O. Kreye, S. Wald, M. A. R. Meier, Adv. Synth. Catal. 2013, 355, 81.
44. a) A. Mohammad Inamuddin, Green Solvents I: Properties and Applications in Chemistry, Springer, New York 2012, Ch. 12, p. 363
45. b) A.-A. G. Shaikh, S. Sivaram, Chem. Rev. 1996, 96, 951
46. c) P. Tundo, M. Selva, Acc. Chem. Res. 2002, 35, 706.
47. M. Firdaus, L. M. de Espinosa, M. A. R. Meier, Macromolecules 2011, 44, 7253.
48. G. F. Rouault, H. D. Rhodes, U.S. Patent 2397508, 1946.
49. a) B. Kovacevic, Z. B. Maksic, Org. Lett. 2001, 3, 1523
50. b) M. K. Kiesewetter, E. J Shin, J. L. Hedrick, R. M. Waymouth, Macromolecules 2010, 43, 2093
51. c) J. E. Taylor, S. D. Bull, J. M. J. Williams, Chem. Soc. Rev. 2012, 41, 2109
52. d) D. Tang, D. Mulder, B. A. J. Noordover, C. E. Koning, Macromol. Rapid Commun. 2011, 32, 1379
53. e) J. Alsarraf, Y. A. Ammar, F. Robert, E. Cloutet, H. Cramail, Y. Landais, Macromolecules 2012, 45, 2249.
54. R. Mahrwald, J. Prakt. Chem. 1999, 341, 191.
55. A. Casas, M. J. Ramos, J. F. Rodriguez, A. Perez, Fuel Process. Technol. 2013, 106, 321.