Tunable poly(hydroxyl urethane) from CO2-Based intermediates using thiol-ene chemistry

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 49, Issue 9, 2011, Pages 2024-2032

  Tang, Chau N ^a   Nulwala, Hunaid B ^a   Damodaran, Krishnan ^b   Kaur, Palwinder ^c   Luebke, David R ^a  

^a NATIONAL ENERGY TECHNOLOGY LABORATORY   (United States)

^b UNIVERSITY OF PITTSBURGH   (United States)

^c University of Pittsburgh   (United States)

Author keywords

amine; carbonate; crosslinked polyurethanes; poly(hydroxyl urethane)s; thiol ene chemistry

Indexed keywords

CROSSLINKED; CROSSLINKED POLYURETHANES; CYCLIC CARBONATES; DIETHYLENETRIAMINE; GLASS TRANSITION TEMPERATURE; MULTI-FUNCTIONAL; POLY(HYDROXYL URETHANE)S; QUANTITATIVE YIELDS; SCALE-UP; TETRAKIS; THERMAL DECOMPOSITION TEMPERATURE; THIOL-ENE CHEMISTRY; THIOL-ENE REACTIONS; THIOL-ENES;

AMINES; BINDERS; CARBONATES; CARBONATION; GLASS TRANSITION; POLYURETHANES; PYROLYSIS; RESINS;

CROSSLINKING;

EID: 79953058499     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.24631     Document Type: Article

References (69)

1. Haszeldine, R. S., Science 2009, 325, 1647-1652.
2. Melillo, J. M.,;, McGuire, A. D.,;, Kicklighter, D. W.,;, Moore, B.,;, Vorosmarty, C. J.,;, Schloss, A. L., Nature 1993, 363, 234-240.
3. Sarmiento, J. L.,;, Le Quéré, C., Science 1996, 274, 1346-1350.
4. Hansen, J.,;, Johnson, D.,;, Lacis, A.,;, Lebedeff, S.,;, Lee, P.,;, Rind, D.,;, Russell, G., Science 1981, 213, 957-966.
5. Song, C., Catal Today 2006, 115, 2-32.
6. Kihara, N.,;, Endo, T., J Polym Sci Part A: Polym Chem 1993, 31, 2765-2773.
7. Tomita, H.,;, Sanda, F.,;, Endo, T., J Polym Sci Part A: Polym Chem 2001, 39, 860-867.
8. Webster, D., Prog Org Coat 2003, 47, 77.
9. Allen, S. D.,;, Byrne, C. M.,;, Coates, G. W., In Feedstocks for the Future;, Bozell, J. J.,;, Patel, M. K., Eds.; ACS Symposium Series 921; American Chemical Society: Washington, DC, 2006; pp 116-129.
10. Darensbourg, D., J Chem Rev 2007, 107, 2388-2410.
11. Belliveau, B. P.,;, Downie, R. B., U.S. Patent 7,588,707, September 15, 2009.
12. Zhu, Z.,;, Einset, A. G.,;, Yang, C.-Y.,;, Chen, W.-X.,;, Wnek, G. E., Macromolecules 1994, 27, 4076-4079.
13. Sakakura, T.,;, Choi, J.-C.,;, Yasuda, H., Chem Rev 2007, 107, 2365-2387.
14. Vora, A.,;, Nasrullah, M.,;, Webster, D., J Coat Technol Res 2010, 7, 409-417.
15. Anderson, A. G., U.S. Patent 5,977,262, November 2, 1999.
16. December, T. S.,;, Harris, P. J., U.S. Patent 5,431,791, July 11, 1995.
17. Frishchinger, I.,;, Cotting, J.,;, Finter, J.,;, Francois, J., U.S. Patent 6,090,891, July 18, 2000.
18. Pacheco, M. A.,;, Marshall, C. L., Energy Fuels 1997, 11, 2-29.
19. Steblyanko, A.,;, Choi, W.,;, Sanda, F.,;, Endo, T., J Polym Sci Part A: Polym Chem 2000, 38, 2375-2380.
20. Shaikh, A.-A. G.,;, Sivaram, S., Chem Rev 1996, 96, 951-976.
21. Buchard, A.,;, Kember, M. R.,;, Sandeman, K. G.,;, Williams, C. K., Chem Commun 2011, 47, 212-214.
22. North, M.,;, Pasquale, R.,;, Young, C., Green Chem 2010, 12, 1514-1539.
23. Darensbourg, D. J.,;, Horn, A., Jr.,;, Moncada, A. I., Green Chem 2010, 12, 1376-1379.
24. Ji, D.,;, Lu, X.,;, He, R., Appl Catal A: Gen 2000, 203, 329-333.
25. Rokicki, G.,;, Rakoczy, P.,;, Parzuchowski, P.,;, Sobiecki, M., Green Chem 2005, 7, 529-539.
26. Aresta, M.,;, Dibenedetto, A., J Mol Catal A: Chem 2002, 182-183, 399-409.
27. Eghbali, N.,;, Li, C.-J., Green Chem 2007, 9, 213-215.
28. Huang, S.,;, Liu, S.,;, Li, J.,;, Zhao, N.,;, Wei, W.,;, Sun, Y., J Fuel Chem Technol 2007, 35, 701-705.
29. Decortes, A.,;, Martinez Belmonte, M.,;, Benet-Buchholz, J.,;, Kleij, A. W., Chem Commun 2010, 46, 4580-4582.
30. Paddock, R. L.,;, Nguyen, S. T., J Am Chem Soc 2001, 123, 11498-11499.
31. Trost, B. M.,;, Angle, S. R., J Am Chem Soc 1985, 107, 6123-6124.
32. Fujinami, T.,;, Suzuki, T.,;, Kamiya, M.,;, Fukuzawa, S.-i.,;, Sakai, S., Chem Lett 1985, 14, 199-200.
33. Bai, D.,;, Jing, H.,;, Liu, Q.,;, Zhu, Q.,;, Zhao, X., Catal Commun 2009, 11, 155-157.
34. Bai, D.,;, Jing, H., Green Chem 2010, 12, 39-41.
35. Xiong, Y.,;, Wang, H.,;, Wang, R.,;, Yan, Y.,;, Zheng, B.,;, Wang, Y., Chem Commun 2010, 46, 3399-3401.
36. Paddock, R. L.,;, Nguyen, S. T., Chem Commun 2004, 1622-1623.
37. Jing, H.,;, Nguyen, S. T., J Mol Catal A: Chem 2007, 261, 12-15.
38. Sun, J.,;, Wang, L.,;, Zhang, S.,;, Li, Z.,;, Zhang, X.,;, Dai, W.,;, Mori, R., J Mol Catal A: Chem 2006, 256, 295-300.
39. Li, F.,;, Xiao, L.,;, Xia, C.,;, Hu, B., Tetrahedron Lett 2004, 45, 8307-8310.
40. Barkakaty, B.,;, Morino, K.,;, Sudo, A.,;, Endo, T., Green Chem 2010, 12, 42-44.
41. Wang, J.-L.,;, Wang, J.-Q.,;, He, L.-N.,;, Dou, X.-Y.,;, Wu, F., Green Chem 2008, 10, 1218-1223.
42. Gesser, H. D.,;, Lafreniere, D. R. T., Prog Org Coat 2004, 49, 372-374.
43. Fukuoka, S.,;, Kawamura, M.,;, Komiya, K.,;, Tojo, M.,;, Hachiya, H.,;, Hasegawa, K.,;, Aminaka, M.,;, Okamoto, H.,;, Fukawa, I.,;, Konno, S., Green Chem 2003, 5, 497-507.
44. Takizawa, K.,;, Nulwala, H.,;, Thibault, R. J.,;, Lowenhielm, P.,;, Yoshinaga, K.,;, Wooley, K. L.,;, Hawker, C. J., J Polym Sci Part A: Polym Chem 2008, 46, 2897-2912.
45. Nulwala, H.,;, Burke, D. J.,;, Khan, A.,;, Serrano, A.,;, Hawker, C. J., Macromolecules 2010, 43, 5474-5477.
46. Nulwala, H.,;, Takizawa, K.,;, Odukale, A.,;, Khan, A.,;, Thibault, R. J.,;, Taft, B. R.,;, Lipshutz, B. H.,;, Hawker, C. J., Macromolecules 2009, 42, 6068-6074.
47. Campos, L. M.,;, Truong, T. T.,;, Shim, D. E.,;, Dimitriou, M. D.,;, Shir, D.,;, Meinel, I.,;, Gerbec, J. A.,;, Hahn, H. T.,;, Rogers, J. A.,;, Hawker, C., J Chem Mater 2009, 21, 5319-5326.
48. Campos, L. M.,;, Meinel, I.,;, Guino, R. G.,;, Schierhorn, M.,;, Gupta, N.,;, Stucky, G. D.,;, Hawker, C. J., Adv Mater 2008, 20, 3728-3733.
49. Campos, L. M.,;, Killops, K. L.,;, Sakai, R.,;, Paulusse, J. M. J.,;, Damiron, D.,;, Drockenmuller, E.,;, Messmore, B. W.,;, Hawker, C. J., Macromolecules 2008, 41, 7063-7070.
50. Killops, K. L.,;, Campos, L. M.,;, Hawker, C. J., J Am Chem Soc 2008, 130, 5062-5064.
51. Montanez, M. I.,;, Campos, L. M.,;, Antoni, P.,;, Hed, Y.,;, Walter, M. V.,;, Krull, B. T.,;, Khan, A.,;, Hult, A.,;, Hawker, C. J.,;, Malkoch, M., Macromolecules 2010, 43, 6004-6013.
52. Hagberg, E. C.,;, Malkoch, M.,;, Ling, Y.,;, Hawker, C. J.,;, Carter, K. R., Nano Lett 2007, 7, 233-237.
53. Antoni, P.,;, Robb, M. J.,;, Campos, L.,;, Montanez, M.,;, Hult, A.,;, Malmström, E.,;, Malkoch, M.,;, Hawker, C., J Macromolecules 2010, 43, 6625-6631.
54. Iha, R. K.,;, Wooley, K. L.,;, Nyström, A. M.,;, Burke, D. J.,;, Kade, M. J.,;, Hawker, C., J Chem Rev 2009, 109, 5620-5686.
55. Joralemon, M. J.,;, O'Reilly, R. K.,;, Hawker, C. J.,;, Wooley, K. L., J Am Chem Soc 2005, 127, 16892-16899.
56. Malkoch, M.,;, Thibault, R. J.,;, Drockenmuller, E.,;, Messerschmidt, M.,;, Voit, B.,;, Russell, T. P.,;, Hawker, C. J., J Am Chem Soc 2005, 127, 14942-14949.
57. O'Reilly, R. K.,;, Joralemon, M. J.,;, Wooley, K. L.,;, Hawker, C. J., Chem Mater 2005, 17, 5976-5988.
58. Thibault, R. J.,;, Takizawa, K.,;, Lowenheilm, P.,;, Helms, B.,;, Mynar, J. L.,;, Fréchet, J. M. J.,;, Hawker, C. J., J Am Chem Soc 2006, 128, 12084-12085.
59. Hein, J. E.,;, Tripp, J. C.,;, Krasnova, L. B.,;, Sharpless, K. B.,;, Fokin, V. V., Angew Chem Int Ed 2009, 48, 8018-8021.
60. Díaz, D. D.,;, Punna, S.,;, Holzer, P.,;, McPherson, A. K.,;, Sharpless, K. B.,;, Fokin, V. V.,;, Finn, M. G., J Polym Sci Part A: Polym Chem 2004, 42, 4392-4403.
61. Hawker, C. J.,;, Wooley, K. L., Science 2005, 309, 1200-1205.
62. Malkoch, M.,;, Vestberg, R.,;, Gupta, N.,;, Mespouille, L.,;, Dubois, P.,;, Mason, A. F.,;, Hedrick, J. L.,;, Liao, Q.,;, Frank, C. W.,;, Kingsbury, K.,;, Hawker, C. J., Chem Commun 2006, 2774-2776.
63. van Berkel, K. Y.,;, Hawker, C. J., J Polym Sci Part A: Polym Chem 2010, 48, 1594-1606.
64. Kade, M. J.,;, Burke, D. J.,;, Hawker, C. J., J Polym Sci Part A: Polym Chem 2010, 48, 743-750.
65. Boyer, C.,;, Granville, A.,;, Davis, T. P.,;, Bulmus, V., J Polym Sci Part A: Polym Chem 2009, 47, 3773-3794.
66. Yu, B.,;, Chan, J. W.,;, Hoyle, C. E.,;, Lowe, A. B., J Polym Sci Part A: Polym Chem 2009, 47, 3544-3557.
67. Van Holen, J., U.S. Patent 0,113,594 A1, May 26, 2005.
68. Tomita, H.,;, Sanda, F.,;, Endo, T., J Polym Sci Part A: Polym Chem 2001, 39, 3678-3685.
69. Rousseau, J.,;, Rousseau, C.,;, Lynikaite, B.,;, Sackus, A.,;, de Leon, C.,;, Rollin, P.,;, TatibouÃt, A., Tetrahedron 2009, 65, 8571-8581.