[en] Star-shaped poly(e-caprolactone)s are functionalized by various dienes (furan and anthracene) and a dienophile (maleimide), and the kinetics of network formation by melt-blending is compared for both Diels–Alder adducts. When curing at 60 °C, the anthracene–maleimide network forms more rapidly and gives rise to a more crosslinked material than with the furan–maleimide adduct. Shape-memory properties of the networks are compared in terms of Diels–Alder adduct stability. Both materials exhibit excellent fixity and recovery ratios, but the relatively low retro Diels–Alder temperature of the furan–maleimide adduct perturbs the mechanical stability of the network during cyclic tensile testing between 0 and 60 °C, whereas the anthracene–maleimide adduct is shown to be stable up to 150 °C.
Research center :
Center for Education and Research on Macromolecules (CERM)
Disciplines :
Chemistry Materials science & engineering
Author, co-author :
Defize, Thomas ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Riva, Raphaël ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Jérôme, Christine ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Alexandre, Michaël ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Language :
English
Title :
Multifunctional poly( ε-caprolactone)-forming networks by Diels–Alder cycloaddition: effect of the adduct on the shape-memory properties
F.R.S.-FNRS - Fonds de la Recherche Scientifique [BE] BELSPO - SPP Politique scientifique - Service Public Fédéral de Programmation Politique scientifique
H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. Int. Ed. 2001, 40, 2004.
C. R. Becer, R. Hoogenboom, U. S. Schubert, Angew. Chem. Int. Ed. 2009, 48, 4900.
M. A. Gauthier, M. I. Gibson, H.-A. Klok, Angew. Chem. Int. Ed. 2009, 48, 48.
W. H. Binder, R. Sachsenhofer, Macromol. Rapid Commun. 2008, 29, 952.
P. Lecomte, R. Riva, C. Jérôme, R. Jérôme, Macromol. Rapid Commun. 2008, 29, 982.
R. J. Pounder, M. J. Stanford, P. Brooks, S. P. Richards, A. P. Dove, Chem. Commun. 2008, 5158.
H. Durmaz, A. Dag, A. Hizal, G. Hizal, U. Tunca, J. Polym. Sci. Part A: Polym. Chem. 2008, 46, 7091.
J. R. Jones, C. L. Liotta, D. M. Collard, D. A. Schiraldi, Macromolecules 1999, 32, 5786.
H. Durmaz, A. Dag, G. Hizal, U. Tunca, J. Polym. Sci. Part A: Polym. Chem. 2011, 49, 1195.
B. Gacal, H. Durmaz, M. A. Tasdelen, G. Hizal, U. Tunca, Y. Yagci, A. L. Demirel, Macromolecules 2006, 39, 5330.
K. Masutani, S. Kawabata, T. Aoki, Y. Kimura, Polym. Int. 2010, 59, 1526.
S. D. Bergman, F. Wudl, in Self Healing Materials. An Alternative Approach to 20 Centuries of Materials Science (Ed:, S. van der Zwaag,), Springer, Heidelberg 2007, p. 45.
J. A. Syrett, G. Mantovani, W. R. S. Barton, D. Price, D. M. Haddleton, Polym. Chem. 2010, 1, 102.
K. Ishida, N. Yoshie, Macromol. Biosci. 2008, 8, 916.
X. Chen, F. Wudl, A. K. Mal, H. Shen, S. R. Nutt, Macromolecules 2003, 36, 1802.
Q. Tian, Y. C. Yuan, M. Z. Rong, M. Q. Zhang, J. Mater. Chem. 2009, 19, 1289.
R. Gheneim, C. Perez-Berumen, A. Gandini, Macromolecules 2002, 35, 7246.
K. Inoue, M. Yamashiro, M. Iji, J. Appl. Polym. Sci. 2009, 112, 876.
T. Defize, R. Riva, J.-M. Raquez, P. Dubois, C. Jérôme, M. Alexandre, Macromol. Rapid Commun. 2011, 32, 1264.
M. Behl, M. Y. Razzaq, A. Lendlein, Adv. Mater. 2010, 22, 3388.
A. Lendlein, H. Jiang, O. Juenger, R. Langer, Nature 2005, 434, 879.
I. A. Rousseau, Polym. Eng. Sci. 2008, 48, 2075.
M. Behl, J. Zotzmann, A. Lendlein, Adv. Polym. Sci. 2010, 226, 1.
T. Defize, R. Riva, J.-M. Thomassin, C. Jérôme, M. Alexandre, Macromol. Symp. 2011.
W. H. Heath, F. Palmieri, J. R. Adams, B. K. Long, J. Chute, T. W. Holcombe, S. Zieren, M. J. Truitt, J. L. White, C. G. Willson, Macromolecules 2008, 41, 719.
K. Ishida, V. Weibel, N. Yoshie, Polymer 2011, 52, 2877.
B. Rickborn, The Retro-Diels-Alder Reaction Part I. C-C Dienophiles, John Wiley & Sons, Inc., New York 2004.