Abstract
Multifunctional crosslinkers having two, three, four and six functionalities were synthesized using a convergent method and were applied to a photocrosslinking system having thermally degradable properties. The multifunctional crosslinkers contained epoxy units and tertiary ester linkages. When the blended films of epoxides/poly(p-vinylphenol) with a photoacid generator were irradiated and followed by baking at relatively lower temperatures (<100 °C), the films became insoluble in solvents. Heating conditions strongly affected the insoluble fraction of the blends. Insoluble fraction of the blended films increased with the number of the epoxy unit of a molecule. The crosslinked films became soluble after prolonged bake at relatively higher treatments (>120 °C). The reaction pathway of the blended system was studied by in situ FT-IR measurements.
Similar content being viewed by others
Article PDF
References
G. C. Tesero and V. Sastri, J. Appl. Polym. Sci., 39, 1425 (1990).
V. Sastri and G. C. Tesero, J. Appl. Polym. Sci., 39, 1439 (1990).
S. L. Buchwalter and L. L. Kosber, J. Polym. Sci., Part A: Polym. Chem., 34, 249 (1996).
S. Yang, J.-S. Chen, H. Korner, T. Breiner, and C. K. Ober, Chem. Mater., 10, 1475 (1998).
J.-S. Chen, C. K. Ober, and M. D. Poliks, Polymer, 43, 131 (2002).
K. Ogino, J.-S. Chen, and C. K. Ober, Chem. Mater., 10, 3833 (1998).
L. Wang, H. Li, and C. P. Wong, J. Polym. Sci., Part A: Polym. Chem., 38, 3771 (2000).
L. Wang and C. P. Wong, J. Polym. Sci., Part A: Polym. Chem., 37, 2991 (1999).
J. Malik and S. J. Clarson, Polym. Degrad. Stab., 76, 241 (2002).
J. Malik and S. J. Clarson, Polymer, 43, 2561 (2002).
Z. G. Wang, M. R. Xie, Y. F. Zhao, Y. Z. Yu, and S. B. Fang, Polymer, 44, 923 (2003).
M. Shirai, S. Morishita, H. Okamura, and M. Tsunooka, Chem. Mater., 14, 334 (2002).
H. Okamura, S. Toda, M. Tsunooka, and M. Shirai, J. Polym. Sci., Part A: Polym. Chem., 40, 3055 (2002).
M. Shirai, A. Kawaue, H. Okamura, and M. Tsunooka, Chem. Lett., 31, 940 (2002).
M. Shirai, A. Kawaue, H. Okamura, and M. Tsunooka, Chem. Mater., 15, 4075 (2003).
Y.-D. Shin, A. Kawaue, H. Okamura, and M. Shirai, Polym. Degrad. Stab., 86, 153 (2004).
Y.-D. Shin, A. Kawaue, H. Okamura, and M. Shirai, React. Funct. Polym., 61, 293 (2004).
H. Okamura, K. Shin, M. Tsunooka, and M. Shirai, J. Polym. Sci., Part A: Polym. Chem., 42, 3685 (2004).
M. Shirai, H. Kinoshita, and M. Tsunooka, Eur. Polym. J., 28, 379 (1992).
W. Offermann and F. Vogtle, Synthesis, 4, 273 (1977).
M. McWatt and G. J. Boons, Eur. J. Org. Chem., 2535 (2001).
N. Nemoto, F. Miyata, and Y. Nagase, Macromolecules, 29, 2365 (1996).
C.-A. Fustin, C. Bailly, G. J. Clarkson, P. De Groote, T. H. Galow, D. A. Leigh, D. Robertson, A. M. Z. Slawin, and J. K. Y. Wong, J. Am. Chem. Soc., 125, 2200 (2003).
H. Ito and M. Ueda, Macromolecules, 21, 1475 (1998).
M. Shirai and M. Tsunooka, Bull. Chem. Soc. Jpn., 71, 2483 (1998).
J. Lalevee, X. Allonas, J. P. Fouassier, M. Shirai, and M. Tsunooka, Chem. Lett., 32, 178 (2003).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Okamura, H., Shin, K. & Shirai, M. Photocrosslinking System Using Highly-Functionalized Epoxy Crosslinkers Having Degradable Property. Polym J 38, 1237–1244 (2006). https://doi.org/10.1295/polymj.PJ2006007
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1295/polymj.PJ2006007
Keywords
This article is cited by
-
Photocrosslinkable polymers with degradable properties
Polymer Journal (2014)
-
Photo- and thermal curing of tri-functional methacrylate with degradable property
Research on Chemical Intermediates (2009)