Cyclic guanidines as efficient organocatalysts for the synthesis of polyurethanes

Macromolecules

Volumn 45, Issue 5, 2012, Pages 2249-2256

  Alsarraf, Jérome ^a,b   Ammar, Yacine Ait ^a,b   Robert, Frédéric ^a,b   Cloutet, Eric ^a,c   Cramail, Henri ^a,c   Landais, Yannick ^a,b  

^a UNIVERSITÉ DE BORDEAUX   (France)

^b CNRS   (France)

^c UNIVERSITÉ BORDEAUX 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BASE CATALYST; DISPERSITY; EFFICIENT CATALYSTS; HIGH REACTIVITY; ISOPHORONE DIISOCYANATE; ORGANOCATALYSTS; POLYADDITION; URETHANE LINKAGE;

CATALYSTS; POLYURETHANES; TIN; UREA;

SELF ASSEMBLY;

EID: 84858234348     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma2026258     Document Type: Article

References (49)

1. Oertel, G. Polyurethane Handbook; Hanser Publishers: Munich, Germany, 1985.
2. Wirpska, Z. Poly(urethane)s: Chemistry, Technology, and Application: Ellis Horwood: London, 1993.
3. Becker, R. L. Thiele, Isocyanate reactions in Polyurethane catalysis: CRC Press, Inc.: Boca Raton, FL, 1996; p 6940.
4. Hepburn, C. Polyurethane Elastomers; Springer: Berlin, 1992.
5. Bayer, O. Angew. Chem. 1947, 59, 257-272
6. Bayer, O.; Müller, E. Angew. Chem. 1960, 72, 934-939
7. Lipatova, T. E.; Bakalo, L. A.; Niselsky, Yu N.; Sirotinskaya, A. L. J. Macromol. Sci.-Chem. 1970, A4 (8) 1743-1758
8. Frisch, K. C.; Rumao, L. P. J. Macromol. Sci.-Rev. Macromol. Chem. 1970, 5c, 103-149
9. Luo, S. G.; Tan, H. M.; Zhang, J. G.; Wu, Y. J.; Pei, F. K.; Meng, X. H. J. Appl. Polymer Sci. 1997, 65, 1217-1225
10. Majundar, K. K.; Kundu, A.; Das, I.; Roy, S. Appl. Organomet. Chem. 2000, 14, 79-85
11. Toxicological Profile for Tin and Tin compounds, ATSDR (Agency for Toxic Substances and Disease Registry), 2005.
12. Revised assessment of the risks to health and the environment associated with the use of the four organotin compounds TBT, DBT, DOT and TPT, The Scientific Committee on Health and Environmental Risks (SCHER), 2006.
13. Kamber, N. E.; Jeong, W.; Waymouth, R. M.; Pratt, R. C.; Lohmeijer, B. G. G.; Hedrick, J. L. Chem. Rev. 2007, 107, 5813-5840
14. Raynaud, J.; Ciolino, A.; Baceiredo, A.; Destarac, M.; Bonnette, F.; Kato, T.; Gnanou, Y.; Taton, D. Angew. Chem., Int. Ed. 2008, 47, 5390-5393
15. Raynaud, J.; Gnanou, Y.; Taton, D. Macromolecules 2009, 42, 5996-6005
16. For the observations of similar reaction rates between organo- and metal-based catalysts, see: McLaughlin, M.; Garcia Rubio, S.; Muthyala, R.; Antunes, O. A. C.; Tilstam, U.; Zlota, A.; Yadav, G. D.; Laird, T. Org. Process Res. Dev. 2006, 10, 853-865
17. Silva, A. L.; Bordado, J. C. Catal. Rev. 2004, 46, 31-51
18. Bantu, B.; Manohar Pawar, G.; Decker, U.; Wurst, K.; Schmidt, A. M.; Buchmeiser, M. R. Chem.-Eur. J. 2009, 15, 3103-3109
19. Bantu, B.; Manohar Pawar, G.; Wurst, K.; Decker, U.; Schmidt, A. M.; Buchmeiser, M. R. Eur. J. Inorg. Chem. 2009, 15, 1970-1976
20. Cramail, H.; Boyer, A.; Cloutet, E.; Bakhiyi, R.; Alfos, C. WO 2011030076, FR2950051.
21. Cramail, H.; Boyer, A.; Cloutet, E.; Alfos, C. WO 2011030075, FR2950052.
22. Cramail, H.; Boyer, A.; Cloutet, E.; Alfos, C. WO 2011045536, FR2951166.
23. Palaskar, D. V.; Boyer, A.; Cloutet, E.; Alfos, C.; Cramail, H. Biomacromolecules 2010, 11, 1202-1211
24. Boyer, A.; Cloutet, E.; Tassaing, T.; Gadenne, B.; Alfos, C.; Cramail, H. Green Chem. 2010, 12, 2205-2213
25. Palaskar, D. V.; Boyer, A.; Cloutet, E.; Le Meins, J. F.; Gadenne, B.; Alfos, C.; Farcet, C.; Cramail, H. J. Polym. Sci., Part A: Polym. Chem. 2012, 10.1002
26. Lohmeijer, B. G. G.; Pratt, R. C.; Leibfarth, F.; Logan, J. W.; Long, D. A.; Dove, A. P.; Nederberg, F.; Choi, J.; Wade, C.; Waymouth, R. M.; Hedrick, J. L. Macromolecules 2006, 39, 8574-8583
27. Chuma, A.; Horn, H. W.; Swope, W. C.; Pratt, R. C.; Zhang, L.; Lohmeijer, B. G. G.; Wade, C. G.; Waymouth, R. M.; Hedrick, J. L.; Rice, J. E. J. Am. Chem. Soc. 2008, 130, 6749-6754
28. Tang, D.; Mulder, D.-J.; Noordover, B. A. J.; Koning, C. E. Macromol. Rapid Commun. 2011, 32, 1379-1385
29. Zhang, L.; Pratt, R. C.; Nederberg, F.; Horn, H. W.; Rice, J. E.; Waymouth, R. M.; Wade, C. G.; Hedrick, J. L. Macromolecules 2010, 43, 1660-1664
30. Kiesewetter, M. K.; Scholten, M. D.; Kirn, N.; Weber, R. L.; Hedrick, J. L.; Waymouth, R. M. J. Org. Chem. 2009, 74, 9490-9496
31. Maliverney, C.; Saint-Jalmes, L. Patent, WO 2010/043353 A1.
32. Raab, V.; Kipke, J.; Gschwind, R. M.; Sundermyer, J. Chem.-Eur. J. 2002, 8, 1682-1693
33. Ishikawa, T. Guanidines in Organic Synthesis in Guanidines, amidines, phosphazenes and related organocatalysts. Superbases for organic synthesis, Ed. J. Wiley & Sons: Chichester, U.K., 2009, p Chapter 4, pp 93-143.
34. Baker, J.; Holsworth, J. B. J. Chem. Soc. 1947, 713-726
35. Schwetlick, K.; Noak, R.; Stebner, F. J. Chem. Soc., Perkin Trans. 2 1994, 599-608
36. Similar mechanisms have been proposed for base-catalyzed alcoholysis of anhydrides, see: Chen, Y.; McDaid, P.; Deng, L. Chem. Rev. 2003, 103, 2965-2983
37. Bonduelle, C.; MartinVaca, B.; Cossio, F. P.; Bourissou, D. Chem.-Eur. J. 2008, 14, 5304-5312
38. Rappo-Abiuso, M.; Llauro, M.-F.; Chevalier, Y.; Le Perchec, P. Phys. Chem. Chem. Phys. 2001, 3, 99-106
39. Bacaloglu, R.; Cotarga, L.; Marcu, N.; Tolgyi, S. J. Prakt. Chem. 1988, 330, 530-540
40. 3CN, see: Kajjurand, I.; Kütt, A.; Sooväli, L.; Rodima, T.; Mäemets, V.; Leito, I.; Koppel, I. A. J. Org. Chem. 2005, 70, 1019-1028
41. Deutsch, J.; Eckelt, R.; Köckritz, A.; Martin, A. Tetrahedron 2009, 65, 10365-10369
42. Pereira, F. S.; deAzevedo, E. R.; da Silva, E. F.; Bonagamba, T. J.; da Silva Agostini, D. L.; Magalhaes, A.; Job, A. E.; Pérez Gonzalez, E. R. Tetrahedron 2008, 64, 10097-10106
43. Oediger, H.; Moeller, F. Ger. Offen. DE 2640964, 1978.
44. Richter, R. Tetrahedron Lett. 1968, 48, 5037-5039
45. Coles, M. P. Chem. Commun. 2009, 3659-3676
46. Barbarini, A.; Maggi, R.; Mazzacani, A.; Mori, G.; Sartori, G.; Sartorio, R. Tetrahedron Lett. 2003, 44, 2931-2934
47. Villers, C.; Dognon, J.-P.; Pollet, R.; Thuéry, P.; Ephritikhine, M. Angew. Chem., Int. Ed. 2010, 49, 3465-3468
48. Das Neves Gomes, C.; Jacquet, O.; Villers, C.; Thuéry, P.; Ephritikhine, M.; Cantat, T. Angew. Chem., Int. Ed. 2012, 51, 187-190
49. Nederberg, F.; Connor, E. F.; Möller, M.; Glauser, T.; Hedrick, J. L. Angew. Chem., Int. Ed. 2001, 40, 2712-2715