Synthesis of an acid-labile diacrylate crosslinker for cleavable michael addition networks

Macromolecular Chemistry and Physics

Volumn 208, Issue 18, 2007, Pages 1949-1955

  Mather, Brian D ^a   Williams, Sharlene R ^a   Long, Timothy E ^a  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

Author keywords

Acetoacetate; Acid cleavable; Acrylate; Michael addition; Networks; TGA

Indexed keywords

CATALYSIS; CONCENTRATION (PROCESS); CROSSLINKING; SYNTHESIS (CHEMICAL); THERMOGRAVIMETRIC ANALYSIS;

ACETOACETATE; ACID-CLEAVABLE; MICHAEL ADDITION;

NEGATIVE IONS;

EID: 34848817403     PISSN: 10221352     EISSN: 15213935     Source Type: Journal    
DOI: 10.1002/macp.200700221     Document Type: Article

References (32)

1. T. Greene, "Protective Groups in Organic Synthesis", Wiley, New York 1999.
2. J. P. Pellois, W. Wang, X. Gao, J. Comb. Chem. 2000, 2, 355.
3. G. Reginato, A. Mordini, M. Caracciolo, J. Org. Chem. 1997, 62, 6187.
4. J.-R. Hwu, M. Jain, S.-C. Tsay, G. Hakimelahi, Tetrahedron Lett. 1996, 37, 2035.
5. K.-D. Ahn, D.-I. Koo, C. Willson, Polymer 1995, 36, 2621.
6. R. B. Merrifield, J. Am. Chem. Soc. 1964, 86, 304.
7. J.-H. Yoo, S.-Y. Kim, I. Cho, J.-M. Kim, K.-D. Ahn, J.-H. Lee, Polymer 2004, 45, 5391.
8. I.M.J. Fréchet,E. Eichler, H. Ito, C. G. Willson, Polymer 1983, 24, 995.
9. S. Q. Chang, R. Ayothi, D. Bratton, D. Yang, N. Felix, H. B. Cao, H. Deng, C. K. Ober, J. Mater. Chem. 2006, 16, 1470.
10. A. H. Gabor, L. C. Pruette, C. K. Ober, Chem. Mater. 1996, 8, 2282.
11. B.D. Mather, K. Viswanathan, K. M. Miller, T. E. Long, Prog. Polym. Sci. 2006, 31, 487.
12. D. B. Curliss, B. A. Cowans, J. M. Caruthers, Macromolecules 1998, 31, 6776.
13. R. J. Clemens, F. D. Rector, J. Coating, Techol. 1989, 61, 83.
14. A. Metters, J. A. Hubbell, Biomacromolecules 2005, 6, 290.
15. R. I. Clemens, J. A. Hyatt, J. Org. Chem. 1985, 50, 2431.
16. J. S. Witzeman, W. D. Nottingham, J. Org. Chem. 1991, 56, 1713.
17. L. Kilian, Z.-H. Wang, T. E. Long, J. Polym. Sci: Part A: Polym. Chem. 2003, 41, 3083.
18. D. Kafouris, E. Themistou, C. S. Patrickios, Chem. Mater. 2006, 18, 85.
19. E. Themistou, C. S. Patrickios, Macromolecules 2006, 39, 73.
20. K. Ogino, J.-S. Chen, C. K. Ober, Chem. Mater. 1998, 10, 3833.
21. E. Ruckenstein, H. M. Zhang, Macromolecules 1999, 32, 3979.
22. N. Murthy, Y. X. Thng, S. Schuck, M. C. Xu, J. M. J. Frechet, J. Am. Chem. Soc. 2002, 124, 12398.
23. D. L. Elbert, A. B. Pratt, M. P. Lutolf, S. Halstenberg, J. A. Hubbell, J. Controlled Release 2001, 76, 11.
24. D. L. Elbert, J. A. Hubbell, Biomacromolecules 2001, 2, 430.
25. B. Vernon, N. Tirelli, T. Bachi, D. Haldimann, J. A. Hubbell, J. Biomed. Mater. Res. 2003, 64, 447.
26. M. Y. Li, R. C. Liang, F. Raymond, A. Reiser, J. Imaging Sci. 1990, 34, 259.
27. S. Yamada, D. R. Medeiros, K. Patterson, W.-L. K. Jen, T. Rager, Q. Lin, C. Lenci, J. D. Byers, J. M. Havard, D. Pasini, J. M. J. Frechet, C. G. Willson, SPIE Proc.: Adv. Resist Technol. Process. 1998, 3333, 245.
28. B. D. Mather, K. M. Miller, T. E. Long, Macromol. Chem. Phys. 2006, 207, 1324.
29. P. Tormala, Eur. Polym. J. 1974, 10, 519.
30. A. Priola, G. Gozzelino, F. Ferrero, G. Malucelli, Polymer 1993, 34, 3653.
31. T. F. Scott, W. D. Cook, J. S. Forsythe, Eur. Polym. J. 2002, 38, 705.
32. C. S. Tyberg, K. Bergeron, M. Sankarapandian, P. Shih, A. C. Loos, D. A. Dillard, J. E. McGrath, J. S. Riffle, U. Sorathia, Polymer 2000, 41, 5053.