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High Performance Photo-curable Polymers and Oligomers Based on Novel Ring-opening Reactions of Oxetanes

Published online by Cambridge University Press:  15 March 2011

Tadatomi Nishikubo  and
Hiroto Kudo
Tadatomi Nishikubo
Affiliation:
Material and Life Chemistry, Kanagawa University, 3-27-1, Rokkakubashi, Kanagawa-ku, Yokohama, 221-8686, Japan
Hiroto Kudo
Affiliation:
Material and Life Chemistry, Kanagawa University, 3-27-1, Rokkakubashi, Kanagawa-ku, Yokohama, 221-8686, Japan
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Abstract

We found new reactionsof oxetanes with many reagents such as acyl chlorides, silyl chlorides, phosphonyl chlorides, alkyl chlorides, aryl esters, thio esters, phosphonic acids, carboxylic acids, thiols, and phenols using suitable quaternary onium salts or crown ether complexes as catalysts. More recently, we also found an anionic ring-opening polymerization of certain oxetane monomers such as (3-methyl-3-hydroxymethyl)oxetane and (3-ethyl-3-hydroxymethyl)oxetane, which have hydroxyl groups, catalyzed by potassium tert-butoxide and 18-crown-6-ether complex, and an anionic ring-opening alternating co-polymerization of oxetane monomers with cyclic carboxylic anhydrides. These reaction systems have also been applied to the synthesis of new functional polymers. In this article, we would like to introduce the application of these reaction systems for the synthesis of high performance new photo-curable polymers and oligomers containing pendant or terminal (meth)acryloyl groups.

Type
Research Article
Information
MRS Online Proceedings Library (OPL) , Volume 1005: Symposium Q – Advances In Photo-Initiated Polymer Processes and Materials , 2007 , 1005-Q02-04
Copyright
Copyright © Materials Research Society 2007

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References

References And Notes

1.For example; Iwakura, Y. and Kurita, K., “Reactive Polymers”, Kodannsha: Tokyo (1977).Google Scholar
2.For example; Kakiuti, H. Ed., “Epoxy Resin”, Shokodo: Tokyo (1985).Google Scholar
3. NOK Co. Ltd., (Inv. Nishikubo, T., Kishida, M., and Inaura, M.), Japan Kokai Koho 49–20292 (1974).Google Scholar
4.(a) Nishikubo, T., Ibuki, S., Mizuko, T., and Takaoka, T., Kobunshi Ronbunshu, 32, 604 (1975).Google Scholar
(b) Nishikubo, T., Kawashima, T., and Watanabe, S., J. Polym. Sci: Part A: Polym. Chem., 31, 1659 (1993).Google Scholar
5. Nishikubo, T., J. Syn. Org. Chem. Jpn., 49, 218 (1991).Google Scholar
6. Nishikubo, T. and Kameyama, A., Prog. Polym. Sci., 18, 963 (1993).Google Scholar
7.For example: Inoue, S. and Aida, T., “Ring-Opening Polymerization”, Ivin, K. J. and Saegusa, T. Eds., Elsevior Applied Science Publishers: London, Vol. 1, pp. 185–298 (1984).Google Scholar
8. Crivello, J. V., “Advance in Polymer Science 62”, Springer-Verlag, Berline, pp. 1–48 (1984).Google Scholar
9. Sasaki, H. and Crivello, J. V., J. Macromol. Sci., A29, 915 (1992).Google Scholar
10.(a) Sasaki, H., Kuriyama, A., and Kakuchi, T., Macromol. Rep., A31, (Suppl. 5), 635 (1994).Google Scholar
(b) Sasaki, H., Kuriyama, A., and Kakuchi, T., Macromol. Rep., A32, 1699 (1995).Google Scholar
11.(a) Yamamura, T., Watanabe, T., Tagami, E., and Ukaji, T., Proceedings of RadTech Asia 97, p. 598 (1997).Google Scholar
(b) Yamamura, T., Tanabe, T., and Ukaji, T., Proceedings of RadTech Asia 99, p. 53 (1999).Google Scholar
12. Nishikubo, T. and Sato, K., Chem. Lett., 1991, 697.Google Scholar
13. Sato, K., Kameyama, A., and Nishikubo, T., Macromolecules, 25, 1198 (1992).Google Scholar
14.For example; (a) Nishikubo, T. and Kameyama, A., Kobunshi Kakou, 52, 16 (2003).Google Scholar
(b) Nishikubo, T. and Kameyama, A., Chemistry and Chemical Industry, 57, 225 (2004).Google Scholar
15. Nishikubo, T., Kameyama, A., and Suzuki, A., Reactive & Functional Polymers, 37, 19–25 (1998).Google Scholar
16. Nishikubo, T., Kameyama, A., Ito, M., and Suzuki, A., J. Polym. Sci. Part A. Polym. Chem., 36, 2873 (1998).Google Scholar
17. Nishikubo, T., Kameyama, A., Ito, M., Nakajima, T., and Miyazaki, H., J. Polym. Sci. Part A. Polym. Chem., 37, (15), 2781 (1999).Google Scholar
18. Nishikubo, T., Kudo, H., Yoshihara, M., and Maruyama, K., J. Polym. Sci. Part A. Polym. Chem., 43, (10), 2028 (2005).Google Scholar
19. Kudo, H., Morita, A., and Nishikubo, T., Polym. J., 35, 88 (2003).Google Scholar
20. Morita, A., Kudo, H., and Nishikubo, T., Polym. J., 36, 413 (2004).Google Scholar
21. Morita, A., Kudo, H., and Nishikubo, T., J. Polym. Sci. Part A. Polym. Chem., 42, 3739 (2004).Google Scholar
22. Kameyama, A., Ueda, K., Kudo, H., and Nishikubo, T., Macromolecules, 35, (10), 3792 (2002).Google Scholar
23. Kudo, H., Ueda, K., Sano, N., and Nishikubo, T., J. Polym. Sci. Part A. Polym. Chem., 41, (13), 1952 (2003).Google Scholar
24. Nishikubo, T., Kameyama, A., and Tsutsui, K., J. Polym. Sci. Part A. Polym. Chem., 39, 1169 (2001).Google Scholar
25. Kameyama, A. and Nishikubo, T., J. Photopolymer Sci. Tech., 17, (1), 45 (2004).Google Scholar
26. Sasaki, M., Kusama, M., Ushiki, S., Kakinuma, M., and Nishikubo, T., 9th International Conference on Radiation Curing, RadTech Asia '03, Proceeding, 600, December 9-12, 2003 (Yokohama).Google Scholar
27.(a) Nishikubo, Tadatomi, Kudo, Hiroto, and Nakagami, Takehiko, Polym. J., 38, 145 (2006).Google Scholar
(b) Nishikubo, T., Kudo, H., Maruyama, K., Nakagami, T., and Miyabe, H., Polym. J., 38, 447 (2006).Google Scholar
28. Nakagami, T., Kudo, H., and Nishikubo, T., Polym. Preprints, Jpn., 52, (2), 255 (2003).Google Scholar
29. Nakagami, T., Iijima, E., Kudo, H., and Nishikubo, T., Polym. Preprints, Jpn., 52, (2), 254 (2003).Google Scholar
30. Morita, A., Kudo, H., and Nishikubo, T., Polym. Preprints, Jpn., 52, (7), 1453 (2003).Google Scholar
31. Morita, A., Sugii, K., Kudo, H., and Nishikubo, T., Polym. Preprints, Jpn., 53, (1), 340 (2004).Google Scholar
32. Kudo, H., Aoki, H., Morita, A., and Nishikubo, T., Polym. Preprints, Jpn., 54, (1), 1327 (2005).Google Scholar