Synthesis of Multifunctional Epoxy Monomers and their Potential Application in the Production of Holographic Photopolymers

Dae-won Chung; Jung Pyo Kim; Daeheum Kim; Jiyun Lim

Journal of Industrial and Engineering Chemistry, Vol.12, No.5, 783-789, September, 2006

Dae-won Chung^†, Jung Pyo Kim, Daeheum Kim¹, and Jiyun Lim¹

Department of Polymer Engineering, University of Suwon, Bongdam-eup, Hwaseong-si, Gyeonggi-do 445-743, Korea
¹Chemical Engineering Department, Kwangwoon University, Wolgye, Nowon, Seoul 139-701, Korea

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Polydimethylsiloxanes having four epoxide functionalities (Multi) were synthesized through hydrosilylation of polydimethylsiloxane-co-polymethylhydrogensiloxane with 4-vinyl-1-cyclohexene 1,2-epoxide and were characterized using FT-IR, 1H-NMR, and 29Si-NMR spectroscopy. Diffraction efficiency studies on the use of Multi as a co-monomer for holographic photopolymerization of 1,3-bis[2-(3-{7-oxabicyclo[4.1.0]heptyl}-tetramethyldisiloxane, based on cationic ring opening polymerization, were undertaken; a fast response time (3 sec) was observed. The effects of the amount of photo-acid generator and chain length of Multi are described.

Keywords:photopolymer;cationic polymerization;polydimethylsiloxane;epoxide;hydrosilylation

[References]

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Sugawara S, Murase K, Kitayama T, Appl. Optics, 14, 378 (1975)
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Blaya S, Mallavia R, Carretero L, Fimia A, Madrigal RF, Appl. Phys. Lett., 75, 1628 (1998)
Ingwall RT, Troll M, Opt. Eng., 28, 586 (1989)
Booth BL, Appl. Optics, 14, 593 (1975)
Monroe BM, J. Imaging Sci., 35, 25 (1991)
Moreau V, Renotte Y, Lion Y, Proc. SPIE, 3951, 108 (1999)
Lawrence JR, O’Neill FT, Sheridan JT, Appl. Optics, 112, 449 (2001)
Crivello JV, Mao Z, Chem. Mater., 9, 1554 (1997)
Crivello JV, Radiat. Phys. Chem., 63, 21 (2002)
Crivello JV, Lam JHW, Macromolecules, 10, 1307 (1977)
Crivello JV, Nucl. Instrum. Methods, B151, 8 (1999)
Kim WG, Ahn HK, Lee HW, Kim SH, Crivello JV, Opt. Mater., 21, 343 (2002)
Crivello JV, Radiat. Phys. Chem., 63, 21 (2002)
Crivello JV, Jang M, J. Photochem. Photobiol. A-Chem., 159, 173 (2003)
Blaya S, Acebal P, Carretero L, Fimia A, Opt. Commun., 228, 55 (2003)
Cetin EA, Minns RA, Waldman DA, U.S. Patent 6,784,300 (2004)
Dhal PK, Horner MG, Ingwall RT, Kolb ES, Mehta PG, Minns RA, Schild HG, Waldman DA, U.S. Patent 5,759,721 (1998)
Kim D, Kim Y, Nam S, Lim J, J. Ind. Eng. Chem., 12(5), 762 (2006)
Phan ST, Lim WC, Han JS, Jung IN, Yoo BR, J. Organomet. Chem., 691, 604 (2006)
Hou SS, Chung YP, Chan CK, Kuo PL, Polymer, 41(9), 3263 (2000)
Rutnakornpituk M, Eur. Polym. J., 41, 1043 (2005)
Vadala ML, Rutnakornpituk M, Zalich MA, St Pierre TG, Riffle JS, Polymer, 45(22), 7449 (2004)
Kim D, Kim Y, Park S, Nam S, J. Polymer Soc. Korea, 8, 515 (2004)
Eckberg RP, LaRocelle RW, U.S. Patent 4,279,717 (1981)
Karstedt BD, Scotia NY, U.S. Patent 3,775,452 (1973)

[Referenced By]

[Related Articles]

[1] Close DH, Jacobson AD, Margerum ID, Brault RG, McClung FJ, Appl. Phys. Lett., 14, 159 (1969)

[2] Sugawara S, Murase K, Kitayama T, Appl. Optics, 14, 378 (1975)

[3] Sukegawa K, Sugawara S, Murase K, Electron. Commun. Jpn., 58-C, 132 (1975)

[4] Blaya S, Mallavia R, Carretero L, Fimia A, Madrigal RF, Appl. Phys. Lett., 75, 1628 (1998)

[5] Ingwall RT, Troll M, Opt. Eng., 28, 586 (1989)

[6] Booth BL, Appl. Optics, 14, 593 (1975)

[7] Monroe BM, J. Imaging Sci., 35, 25 (1991)

[8] Moreau V, Renotte Y, Lion Y, Proc. SPIE, 3951, 108 (1999)

[9] Lawrence JR, O’Neill FT, Sheridan JT, Appl. Optics, 112, 449 (2001)

[10] Crivello JV, Mao Z, Chem. Mater., 9, 1554 (1997)

[11] Crivello JV, Radiat. Phys. Chem., 63, 21 (2002)

[12] Crivello JV, Lam JHW, Macromolecules, 10, 1307 (1977)

[13] Crivello JV, Nucl. Instrum. Methods, B151, 8 (1999)

[14] Kim WG, Ahn HK, Lee HW, Kim SH, Crivello JV, Opt. Mater., 21, 343 (2002)

[15] Crivello JV, Radiat. Phys. Chem., 63, 21 (2002)

[16] Crivello JV, Jang M, J. Photochem. Photobiol. A-Chem., 159, 173 (2003)

[17] Blaya S, Acebal P, Carretero L, Fimia A, Opt. Commun., 228, 55 (2003)

[18] Cetin EA, Minns RA, Waldman DA, U.S. Patent 6,784,300 (2004)

[19] Dhal PK, Horner MG, Ingwall RT, Kolb ES, Mehta PG, Minns RA, Schild HG, Waldman DA, U.S. Patent 5,759,721 (1998)

[20] Kim D, Kim Y, Nam S, Lim J, J. Ind. Eng. Chem., 12(5), 762 (2006)

[21] Phan ST, Lim WC, Han JS, Jung IN, Yoo BR, J. Organomet. Chem., 691, 604 (2006)

[22] Hou SS, Chung YP, Chan CK, Kuo PL, Polymer, 41(9), 3263 (2000)

[23] Rutnakornpituk M, Eur. Polym. J., 41, 1043 (2005)

[24] Vadala ML, Rutnakornpituk M, Zalich MA, St Pierre TG, Riffle JS, Polymer, 45(22), 7449 (2004)

[25] Kim D, Kim Y, Park S, Nam S, J. Polymer Soc. Korea, 8, 515 (2004)

[26] Eckberg RP, LaRocelle RW, U.S. Patent 4,279,717 (1981)

[27] Karstedt BD, Scotia NY, U.S. Patent 3,775,452 (1973)