Synthesis and Photopolymerization of Vinyl Ether and Epoxy-Functionalized Silicones

Sang Yong Pyun; Whan Gi Kim

Macromolecular Research, Vol.11, No.3, 202-205, June, 2003

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Synthesis and Photopolymerization of Vinyl Ether and Epoxy-Functionalized Silicones

Sang Yong Pyun, and Whan Gi Kim^{1, †}

Department of Chemistry, Pukyung National University, Busan 608-737, Korea
¹Department of Applied Chemistry, Konkuk University, 322 Danwol, Chungju 380-701, Korea

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The reactive precursors, vinyl ethers, and epoxy-silicones, were synthesized. The vinyl ether monomers were prepared from primary alcohol and ethyl vinyl ether with mercury (II) acetate. The epoxy-functionalized silicones have been achieved by the controlled, rhodium-catalyzed, chemoselective hydrosilation of vinyl ether with siloxanes or silane. It was shown that the hydrosilation proceeds exclusively at the vinyl ether group of alkenyl vinyl ether without participation at the alkenyl group. The photoinduced cationic polymerization of these monomers was studied and found to be all highly reactive.

Keywords:cationic polymerization;siloxane;silicone;uv-curing;vinyl ether;epoxy;hydrosilation

[References]

Kricheldorf HR, Silicon in Polymer Synthesis, Springer, Berlin (1996)
Fouassier JP, Rabek JF, Radiation Curing in Polymer Science and Technology, Elsevier Applied Science, London and New York (1993)
Pappas SP, RAdiation Curing Science Technology, Plenum Press, London and New York (1992)
Rajaraman SK, Mowers WA, Crivello JV, J. Polym. Sci. A: Polym. Chem., 37(21), 4007 (1999)
Crivello JV, J. Polym. Sci. A: Polym. Chem., 37(23), 4241 (1999)
Crivello JV, Yang B, Kim WG, J. Polym. Sci. A: Polym. Chem., 33(14), 2415 (1995)
Lee JK, Choi Y, Lee JR, Park J, Macromol. Res., 10(1), 34 (2002)
Park J, Korea Polym. J., 9(4), 206 (2001)
Yasuda N, Yamamoto S, Wada Y, Yanagida S, J. Polym. Sci. A: Polym. Chem., 39(24), 4196 (2001)
Malik R, Crivello JV, J. Macromol. Sci.-Pure Appl. Chem., A34(2), 247 (1997)
Furuzono T, Seki K, Kishida A, Ohshige TA, Waki K, Maruyama I, Akashi M, J. Appl. Polym. Sci., 59(7), 1059 (1996)
Lohse F, Zweifel H, Adv. Polym. Sci., 78, 61 (1986)
Okuyama T, Fueno T, Furukawa J, J. Polym. Sci. A: Polym. Chem., 6, 993 (1968)
Eckberg RP, LaRochelle RW, U.S. Patent, 4,279,717 (Chem Abstr 94:158502) (1981)
Crivello JV, Yang B, Kim WG, J. Macromol. Sci.-Pure Appl. Chem., A33(4), 399 (1996)
Brook ML, Silicon in Organic, Organometallic, and Polymer Chemistry, John Wiley & Sons, New York (2000)
Crivello JV, Bi D, J. Polym. Sci. A: Polym. Chem., 31, 3109 (1993)
Crivello JV, Lee JL, J. Polym. Sci. A: Polym. Chem., 27, 3951 (1989)
Guy RK, Dipietro RA, Synth. Commun., 22(5), 687 (1992)
Dektar JL, Hacker NP, J. Org. Chem., 56, 1838 (1991)

[Referenced By]

[1] Kricheldorf HR, Silicon in Polymer Synthesis, Springer, Berlin (1996)

[2] Fouassier JP, Rabek JF, Radiation Curing in Polymer Science and Technology, Elsevier Applied Science, London and New York (1993)

[3] Pappas SP, RAdiation Curing Science Technology, Plenum Press, London and New York (1992)

[4] Rajaraman SK, Mowers WA, Crivello JV, J. Polym. Sci. A: Polym. Chem., 37(21), 4007 (1999)

[5] Crivello JV, J. Polym. Sci. A: Polym. Chem., 37(23), 4241 (1999)

[6] Crivello JV, Yang B, Kim WG, J. Polym. Sci. A: Polym. Chem., 33(14), 2415 (1995)

[7] Lee JK, Choi Y, Lee JR, Park J, Macromol. Res., 10(1), 34 (2002)

[8] Park J, Korea Polym. J., 9(4), 206 (2001)

[9] Yasuda N, Yamamoto S, Wada Y, Yanagida S, J. Polym. Sci. A: Polym. Chem., 39(24), 4196 (2001)

[10] Malik R, Crivello JV, J. Macromol. Sci.-Pure Appl. Chem., A34(2), 247 (1997)

[11] Furuzono T, Seki K, Kishida A, Ohshige TA, Waki K, Maruyama I, Akashi M, J. Appl. Polym. Sci., 59(7), 1059 (1996)

[12] Lohse F, Zweifel H, Adv. Polym. Sci., 78, 61 (1986)

[13] Okuyama T, Fueno T, Furukawa J, J. Polym. Sci. A: Polym. Chem., 6, 993 (1968)

[14] Eckberg RP, LaRochelle RW, U.S. Patent, 4,279,717 (Chem Abstr 94:158502) (1981)

[15] Crivello JV, Yang B, Kim WG, J. Macromol. Sci.-Pure Appl. Chem., A33(4), 399 (1996)

[16] Brook ML, Silicon in Organic, Organometallic, and Polymer Chemistry, John Wiley & Sons, New York (2000)

[17] Crivello JV, Bi D, J. Polym. Sci. A: Polym. Chem., 31, 3109 (1993)

[18] Crivello JV, Lee JL, J. Polym. Sci. A: Polym. Chem., 27, 3951 (1989)

[19] Guy RK, Dipietro RA, Synth. Commun., 22(5), 687 (1992)

[20] Dektar JL, Hacker NP, J. Org. Chem., 56, 1838 (1991)