The Application of the Diels-Alder Reaction to Polymer Syntheses Based on Furan/Maleimide Reversible Couplings
Gandini, Alessandro
http://dx.doi.org/10.1590/S0104-14282005000200007
Polímeros: Ciência e Tecnologia, vol.15, n2, p.95-101, 2005
Abstract
The furan heterocycle is a dienic reagent particularly suitable for the Diels-Alder reaction and maleimides represent a typical family of complementary reagents because of their strong dienophilic character. This paper reviews critically the studies devoted to the exploitation of the Diels Alder reaction between those moieties to synthesise macromolecular materials possessing different structures and properties. The most relevant approaches in this field are (i) polycondensation reactions calling upon A-A and B-B monomers and (ii) reversible cross-linking of linear polymers bearing pendant furan or maleimide moieties, based on the temperature sensitivity of the Diels-Alder equilibrium.
Keywords
Diels-Alder reaction, furan polymers, maleimides, polycondensation, reversible cross-linking
References
1. Moreau, C.; Gandini, A.; Belgacem, M.N. - Topics Catalysis 27 11 (2004).
2. Gandini, A.; Belgacem, M. N. - Prog. Polym. Sci. 22, 1203 (1997).
3. G.C. Tesoro, V.R. Sastri, Ind. Eng. Chem. Prod. Res. Dev. , 25, 444 (1986).
4. He, X.; Sastri, V.R.; Tesoro, G. C. - Makromol. Chem. Rapid. Comm. 9, 191 (1989).
5. O’Dell, R. - PhD Thesis, Lancaster University, UK (1990).
6. Kuramoto, N.; Hayashi, K.; Nagai, K. - J. Polym. Sci. Polym. Chem. 30, 2501 (1992).
7. Diakoumakos, C. D.; Microyannidis, J.A. - J. Polym. Sci. Polym. Chem. 30, 2559 (1992).
8. Diakoumakos, C. D.; Microyannidis, J.A. - Eur. Poly. J. 30, 465 (1994).
9. Goussé, C.; Gandini, A. - Polym. Intern. 48, 723 (1999).
10. Pérez-Berumen, C.; Gandini, A. - unpublished results; C. Pérez-Berumen, Doctorate Thesis, National Polytechnic Institute, Grenoble, France (2003),
11. Kamahori, K.; Tada, S.; Ito, K.; Itsuno, S. - Macromolecules 32, 541 (1999).
12. Mikroyannidis, J. A. - J. Polym. Sci. Polym. Chem. 30, 125 (1992).
13. Mikroyannidis, J. A. - J. Polym. Sci. Polym. Chem. 30, 2017 (1992).
14. Goussé, C.; Gandini, A. - Polym Bull. 40, 389 (1998).
15. McElhanon, J. R.; Wheeler, D.R. - Org. Lett. 3, 2681 (2001).
16. Chen, X.; Dam, M. A.; Ono, K.; Mal, A.K.; Shen, H.; Nutt, S. R.; Sheran, K.; Wudl, F. - Science, 295, 1698 (2002).
17. Chen, X.; Wudl, F.; Mal, A. K.; Shen, H.; Nutt, S. R. - Macrolmolecules, 36, 1802 (2003).
18. Stevens, M.; Jenkins, A. - J. Polym. Sci, 17, 3675 (1979).
19. Chujo, Y.; Sada, K.; Saegusa, T. - Macromolecules 23, 2636 (1990).
20. Canary, S. A.; Stevens, M. P. - J. Polym. Sci. Polym. Chem. 30, 1755 (1992).
21. Imai, Y.; Itoh, H.; Naka, K.; Chujo, Y. - Macromolecules, 33, 4343 (2000).
22. Laita, H.; Boufi, S.; Gandini, A. - Eur. Polym. J. 33, 1203 (1997).
23. Goussé, C.; Gandini, A.; Hodge, P. - Macromolecules, 31, 314 (1998).
24. Gheneim, R.; Pérez-Brumen, C.; Gandini, A. - Macromolecules, 35, 7246 (2002).
25. Gheneim, R. - Doctorate Thesis, National Polytechnic Institute, Grenoble, France (2003),
26. Goiti, E.; Huglin, M. B.; Rego, J. M. - Polymer, 42, 10187 (2001).
27. Goiti, E.; Huglin, M. B.; Rego, J. M. - Macromol. Rapid Comm., 24, 692 (2003).
28. Goiti, E.; Huglin, M. B.; Rego, J. M. - Eur. Polym. J. 40, 219 (2004).
29. Goiti, E.; Huglin, M. B.; Rego, J. M. - Eur. Polym. J. 40, 1451 (2004).
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