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Synthesis and characteristics of curable siloxane-based organic-inorganic hybrid materials modified with vinyl and isopropenoxy

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Abstract

New curable organic-inorganic hybrid materials with a low internal optical attenuation of <0.35 dB/cm at the telecommunication wavelength and high thermal stability (~370 °C) were synthesized by a nonhydrolytic reaction using vinyltriiospropenoxysilane (VTIPS) and diphenylsilanediol (DPSD) in which alcohol condensation takes place without hydrolysis of the starting materials. The molecular structure and the reaction mechanism of the synthesized organic-inorganic hybrid materials were investigated. The nonhydrolytic reaction of VTIPS and DPSD represented a high degree of condensation, and the molecules of the organic-inorganic hybrid materials exhibited the structure of an oligosiloxane modified with diphenyl, vinyl, and isopropenoxy. These organic-inorganic hybrid materials cured by polymerization of vinyl and isopropenoxy groups can be promising candidates for optical applications due to their good optical and thermal properties in addition to the availability of soft-lithography.

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References

  1. C. Sanchez, B. Lebeau, F. Chaput, J. Boilot: Optical properties of functional hybrid organic-inorganic nanocomposites. Adv. Mater. 23, 1969 (2003).

    Article  Google Scholar 

  2. A.O. Karkkainen, J.T. Rantala, A. Maaninen, G.E. Jabbour, M.R. Desour: Siloxane-based hybrid glass materials for binary and grayscale mask photoimaging. Adv. Mater. 7, 535 (2002).

    Article  Google Scholar 

  3. A. Vioux: Nonhydrolytic sol-gel routes to oxides. Chem. Mater. 9, 2292 (1997).

    Article  CAS  Google Scholar 

  4. M. Mennig, M. Zahnhausen, H. Schmidt A novel nonhydrolytic sol-gel route to low–OH and CH-containing organic-inorganic composites, in Organic-Inorganic Hybrid Materials for Photonics, edited by G. Liliane, H.b.r. Pfalzgraf, and S.I. Najafi (SPIE 3469, San Diego, CA, 1998), p. 68.

  5. J.N. Hay, H.N. Raval: Synthesis of organic-inorganic hybrids via the nonhydrolytic sol-gel process. Chem. Mater. 13, 3396 (2001).

    Article  CAS  Google Scholar 

  6. O.V. Mishechkin, D. Lu, M. Fallahi Reliability improvement of hybrid organic-inorganic waveguides by dielectric passivation, in Proceedings of the 16th Annual Meeting of the IEEE Laser and Electro-optics Society, edited by A.E. Willner, L. Esterowitz, P.J. Delfye, H.S. Hinton, M.Y.L. Wisniewski, and N. Dagli (IEEE, Piscataway, NJ, 2003), p. 674.

  7. U. Streppel, P. Dannberg, C. Wachter, A. Brauer, L. Frohlich, R. Houbertz, M. Popall: New wafer-scale fabrication method for stacked optical waveguide interconnects and 3D micro-optic structures using photoresponsive (inorganic-organic hybrid) polymers. Opt. Mater. 21, 475 (2002).

    Article  Google Scholar 

  8. E. Wipfelder, K. Hohn: Epoxysiloxane resins by the condensation of 3-glycidyloxypropyltrimethoxysilane with diphenylsilandiol. Die Ang. Makromol. Chem. 218, 111 (1994).

    Article  CAS  Google Scholar 

  9. R. Buestrich, F. Kahlenberg, M. Popall: ORMORCERs for optical interconnection technology. J. Sol-Gel Sci. Technol. 20, 181 (2001).

    Article  CAS  Google Scholar 

  10. Y.J. Eo, J.H. Kim, J.H. Ko, B.S. Bae: Optical characteristics of photo-curable methacryl-oligosilaxane nano hybrid thick films. J. Mater. Res. 20, 401 (2005).

    Article  CAS  Google Scholar 

  11. R. Houbertz, G. Domann, C. Cronauer, A. Schmitt, H. Martin, J.U. Park, L. Frohlich, R. Buestich, M. Popall, U. Steppel, P. Dannberg, C. Wachter, A. Brauer Inorganic-organic hybrid materials for application in optical devices, in Application, New Markets, Emerging Products, Trends: Optics for Communications, edited by M.A. Aegerter and H.A. Meinema (Proceeding of 4th ICCG, Braunschweig, Germany, 2002), p. 605.

  12. S.Y. Kim, S. Augustine, Y.J. Kim, B.S. Bae, S.I. Woo, J.K. Kang: Mechanism and nanosize products of the sol-gel reaction using diphenylsilanediol and 3-methacryloxypropyltrimethoxysilane as precursors. J. Phys. Chem. B 109, 9397 (2005).

    Article  CAS  Google Scholar 

  13. M.A. Aramendia, V. Borau, C. Jimenez, J.M. Marinas, J.R. Ruiz, F.J. Urbano: a-Arylation of diethyl malonate via enolate with bases in a heterogeneous phase. Tetrahedron Lett. 43, 2847 (2002).

    Article  CAS  Google Scholar 

  14. Y. Dubisky, A. Zaopo, G. Zannoni, L. Zetta: 1H NMR study of the hydrolysis of vinyl trialkoxysilanes. Mater. Chem. Phys. 64, 45 (2000).

    Article  Google Scholar 

  15. D. Hoebbel, T. Reinert, H. Schmidt: Si-29 NMR investigation of condensation reactions of diphenylsilanediol in presence of Ti-, Zr-, Al-, Sn- and Si-alkoxides. J. Sol-Gel. Sci. Technol. 7, 217 (1996).

    Article  CAS  Google Scholar 

  16. I. Yoshinaga, N. Yamada, S. Katayama: Effect of metal alkoxide complexes on condensation reactions of hydrolyzed phenyltriethoxysilane. J. Sol-Gel. Sci. Technol. 28, 65 (2003).

    Article  CAS  Google Scholar 

  17. Y.J. Eo, T.H. Lee, S.Y. Kim, J.K. Kang, Y.S. Han, B.S. Bae: Synthesis and molecular structure analysis of nano-sized methacrylgrafted polysiloxane resin for fabrication of nano hybrid materials. J. Polym. Sci. B 43, 827 (2005).

    Article  CAS  Google Scholar 

  18. F.J. Feher, D.A. Newman, J.F. Walzer: Silsequioxanes as models for silica surfaces. J. Am. Chem. Soc. 111, 1741 (1989).

    Article  CAS  Google Scholar 

  19. M.C. Douskey, M.S. Gebhard, A.V. McCormick, B.C. Lange, D.W. Whitman, M.R. Schure, K. Beshah: Spectroscopic studies of a novel cyclic oligomer with pendant alkoxysilane groups. Prog. Org. Coat. 45, 145 (2002).

    Article  CAS  Google Scholar 

  20. T. Knoche, L. Muller, R. Klein, A. Neyer: Low loss polymer waveguides at 1300 and 1550 nm using halogenated acrylates. Electron. Lett. 32, 1284 (1996).

    Article  CAS  Google Scholar 

  21. M.V. Kunnavakkam, F.M. Houlihan, M. Schlax, J.A. Liddle, P. Kolodner, O. Nalamasu, J.A. Rogers: Low-cost, low-loss microlens arrays fabricated by soft-lithography replication process. Appl. Phys. Lett. 82, 1152 (2003).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Laboratory of Inorganic Photonics Materials, Institute for Chemical Research (ICR), Kyoto University, Uji, Kyoto, 611-0011, Japan

    Eun-Seok Kang, Masahide Takahashi, Yomei Tokuda & Toshinobu Yoko

  2. Precursory Research for Embryonic Science and Technology (PRESTO), Japan Science and Technology Agency, Kawaguchi, Saitama, 332-0012, Japan

    Eun-Seok Kang & Masahide Takahashi

Authors
  1. Eun-Seok Kang
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  2. Masahide Takahashi
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  3. Yomei Tokuda
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  4. Toshinobu Yoko
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Correspondence to Masahide Takahashi.

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Kang, ES., Takahashi, M., Tokuda, Y. et al. Synthesis and characteristics of curable siloxane-based organic-inorganic hybrid materials modified with vinyl and isopropenoxy. Journal of Materials Research 21, 1286–1293 (2006). https://doi.org/10.1557/jmr.2006.0144

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  • DOI: https://doi.org/10.1557/jmr.2006.0144

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