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International Journal of Polymer Science
Volume 2012 (2012), Article ID 526795, 17 pages
Characterization and Some Insights into the Reaction Chemistry of Polymethylsilsesquioxane or Methyl Silicone Resins
1Electronics Solutions S&T, Dow Corning Toray Co., Ltd., 2-2 Chigusa-Kaigan, Chiba Ichihara 299-0108, Japan
2Analytical Sciences, Dow Corning Corporation, 2200 W. Salzburg Road, Midland, MI 48686-0994, USA
3Institute for Inorganic and Analytical Chemistry, Goethe University Frankfurt, Max-von-Laue-Straße 7, 60438 Frankfurt am Main, Germany
Received 15 June 2012; Accepted 17 August 2012
Academic Editor: Takahiro Gunji
Copyright © 2012 Maki Itoh et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
- L. H. Brown, “Silicones in protective coatings,” in Treatise on Coatings, R. Myers and J. S. Long, Eds., vol. 1, part 3, chapter 13, pp. 513–563, Marcel Dekker, New York, NY, USA, 1972.
- R. H. Baney, M. Itoh, A. Sakakibara, and T. Suzuki, “Silsesquioxanes,” Chemical Reviews, vol. 95, no. 5, pp. 1409–1430, 1995.
- M. G. Voronkov and V. I. Lavrent'yev, “Polyhedral oligosilsesquioxanes and their homo delivatives,” Topics in Current Chemistry, vol. 102, pp. 199–236, 1982.
- P. G. Harrison, “Silicate cages: precursors to new materials,” Journal of Organometallic Chemistry, vol. 542, no. 2, pp. 141–183, 1997.
- V. Chandrasekhar, R. Boomishankar, and S. Nagendran, “Recent developments in the synthesis and structure of organosilanols,” Chemical Reviews, vol. 104, no. 12, pp. 5847–5910, 2004.
- D. B. Cordes, P. D. Lickiss, and F. Rataboul, “Recent developments in the chemistry of cubic polyhedral oligosilsesquioxanes,” Chemical Reviews, vol. 110, no. 4, pp. 2081–2173, 2010.
- E. L. Warrick, Forty Years of Firsts: The Recollections of a Dow Corning Pioneer, chapter 1, McGraw-Hill, New York, NY, USA, 1990.
- J. F. Brown Jr., J. H. Vogt Jr., A. Katchman, J. W. Eustance, K. M. Kiser, and K. W. Krantz, “Double chain polymers of phenylsilsesquioxane,” Journal of the American Chemical Society, vol. 82, no. 23, pp. 6194–6195, 1960.
- J. F. Brown, “Double chain polymers and nonrandom crosslinking,” Journal of Polymer Science C, vol. 1, no. 1, pp. 83–97, 1963.
- K. A. Andrianov, A. A. Zhdanov, and V. Yu Levin, “Some physical properties of organosilicon ladder polymers,” Annual Review of Materials Science, vol. 8, pp. 313–326, 1978.
- D. Ya Tsvankin, V. Yu Levin, V. S. Pankov, V. P. Zhukov, A. A. Zhdanov, and K. A. Andrianov, “New type of temperature variation of X-ray diffraction from a number of polymers,” Polymer Science U.S.S.R., vol. 21, no. 9, pp. 2348–2358, 1979.
- E. S. Park, H. W. Ro, C. V. Nguyen, R. L. Jaffe, and D. Y. Yoon, “Infrared spectroscopy study of microstructures of poly(silsesquioxane)s,” Chemistry of Materials, vol. 20, no. 4, pp. 1548–1554, 2008.
- T. E. Helminiak, C. L. Benner, and W. E. Gibbs, “Some solution properties of the ladder polymer cis-syndiotactic poly-phenylsilsesquioxane,” ACS Polymer Preprints, vol. 8, pp. 284–291, 1967.
- V. N. Tsvetkov, K. A. Andrianov, G. I. Okhrimenko, and M. G. Vitovskaya, “Conformation and rigidity of ladder polymer molecules,” European Polymer Journal, vol. 7, no. 9, pp. 1215–1230, 1971.
- L. Shi, X. Zhang, Y. Si, M. Ye, and D. Li, “Solution properties of ladder-like polymer polyphenylsilsesquioxanes,” Chinese Journal of Polymer Science, vol. 5, no. 4, pp. 359–365, 1987.
- T. E. Helminiak and G. C. Berry, “Properties of the ladder polymer cis-syndiotactic poly(phenylsilsesquioxane) in solution,” Journal of Polymer Science, vol. 65, no. 1, pp. 107–123, 1978.
- C. L. Frye and J. M. Klosowski, “Concerning the so-called “ladder structure” of equilibrated phenylsilsesquioxane,” Journal of the American Chemical Society, vol. 93, no. 18, pp. 4599–4601, 1971.
- M. Unno, A. Suto, K. Takada, and H. Matsumoto, “Synthesis of ladder and cage silsesquioxanes from 1,2,3,4- tetrahydroxycyclotetrasiloxane,” Bulletin of the Chemical Society of Japan, vol. 73, no. 1, pp. 215–220, 2000.
- M. Unno, A. Suto, and H. Matsumoto, “Pentacyclic laddersiloxane,” Journal of the American Chemical Society, vol. 124, no. 8, pp. 1574–1575, 2002.
- M. Unno, T. Matsumoto, and H. Matsumoto, “Synthesis of laddersiloxanes by novel stereocontrolled approach,” Journal of Organometallic Chemistry, vol. 692, no. 1–3, pp. 307–312, 2007.
- S. Chang, T. Matsumoto, H. Matsumoto, and M. Unno, “Synthesis and characterization of heptacyclic laddersiloxanes and ladder polysilsesquioxane,” Applied Organometallic Chemistry, vol. 24, no. 3, pp. 241–246, 2010.
- S. Kyushin, R. Tanaka, K. Arai, A. Sakamoto, and H. Matsumoto, “Domino oxidation of ladder oligosilanes: formation of novel ladder frameworks containing oligosiloxane and oligosilane chains,” Chemistry Letters, no. 12, pp. 1297–1298, 1999.
- H. Seki, T. Kajiwara, Y. Abe, and T. Gunji, “Synthesis and structure of ladder polymethylsilsesquioxanes from sila-functionalized cyclotetrasiloxanes,” Journal of Organometallic Chemistry, vol. 695, no. 9, pp. 1363–1369, 2010.
- A. J. Barry, W. H. Daudt, J. J. Domicone, and J. W. Gilkey, “Crystalline organosilsesquioxanes,” Journal of the American Chemical Society, vol. 77, no. 16, pp. 4248–4252, 1955.
- K. A. Andrianov and B. A. Lzmaylov, “Hydrolytic poly-condensation of higher alkyltrichlorosilanes,” Journal of Organometallic Chemistry, vol. 8, no. 3, pp. 435–441, 1967.
- C. L. Frye and W. T. Collins, “The oligomeric silsesquioxanes, (HSiO3/2)n,” Journal of the American Chemical Society, vol. 92, no. 19, pp. 5586–5588, 1970.
- P. A. Agaskar and W. G. Klemperer, “The higher hydridospherosiloxanes: synthesis and structures of (),” Inorganica Chimica Acta, vol. 229, no. 1-2, pp. 355–364, 1995.
- F. J. Feher, D. A. Newman, and J. F. Walzer, “Silsesquioxanes as models for silica surfaces,” Journal of the American Chemical Society, vol. 111, no. 5, pp. 1741–1748, 1989.
- T. Kondo, K. Yoshii, K. Horie, and M. Itoh, “Photoprobe study of siloxane polymers. 3. Local free volume of polymethylsilsesquioxane probed by photoisomerization of azobenzene,” Macromolecules, vol. 33, no. 10, pp. 3650–3658, 2000.
- Z. Xie, Z. He, D. Dai, and R. Zhang, “Study on the synthesis and characterization of the soluble, high molecular weight and ladderlike polymethylsilsesquioxane,” Chinese Journal of Polymer Science, vol. 7, no. 2, pp. 183–188, 1989.
- G. E. Maciel, M. J. Sullivan, and D. W. Sindorf, “Carbon-13 and silicon-29 nuclear magnetic resonance spectra of solid poly(methylsiloxane) polymers,” Macromolecules, vol. 14, no. 5, pp. 1607–1608, 1981.
- G. Engelhardt, H. Jancke, E. Lippmaa, and A. Samoson, “Structure investigations of solid organosilicon polymers by high resolution solid state 29Si NMR,” Journal of Organometallic Chemistry, vol. 210, no. 3, pp. 295–301, 1981.
- E. D. Lipp, “Deuteration technique to detect trace silanol by IR spectroscopy,” Personal communication to M. Itoh, March 2000.
- F. J. Feher, D. Soulivong, and G. T. Lewis, “Facile framework cleavage reactions of a completely condensed silesquioxane framework,” Journal of the American Chemical Society, vol. 119, no. 46, pp. 11323–11324, 1997.
- M. Unno, S. B. Alias, H. Saito, and H. Matsumoto, “Synthesis of hexasilsesquioxanes bearing bulky substituents: hexakis((1,1,2-trimethylpropyl)silsesquioxane) and hexakis (tert-butylsilsesquioxane),” Organometallics, vol. 15, no. 9, pp. 2413–2414, 1996.
- R. B. Taylor, B. Parbhoo, and D. M. Fillmore, “Muclear magnetic resonance spectroscopy,” in The Analytical Chemistry of Silicones, A. Lee Smith, Ed., pp. 382–383, John Wiley & Sons, New York, NY, USA, 1991.
- I. Hasegawa, S. Sakka, K. Kuroda, and C. Kato, “Trimethylsilylation of the hydrolysed and polycondensed products of methyltriethoxysilane,” Journal of Chromatography A, vol. 410, pp. 137–143, 1987.
- R. E. Tecklenburg, W. E. Wallace, and H. Chen, “Characterization of a [(O3/2SiMe)×(OSi(OH)Me)y(OSiMe2)z] silsesquioxane copolymer resin by mass spectrometry,” Rapid Communications in Mass Spectrometry, vol. 15, no. 22, pp. 2176–2185, 2001.
- H.-J. Kim, J.-K. Lee, S.-J. Park, H. W. Ro, D. Y. Yoo, and D. Y. Yoon, “Observation of low molecular weight poly(methylsilsesquioxane)s by graphite plate laser desorption/ionization time-of-flight mass spectrometry,” Analytical Chemistry, vol. 72, no. 22, pp. 5673–5678, 2000.
- H. W. Ro, E. S. Park, C. L. Soles, and D. Y. Yoon, “Structure-property relationships for methylsilsesquioxanes,” Chemistry of Materials, vol. 22, no. 4, pp. 1330–1339, 2010.
- R. E. Tecklenburg, “Electrospray mass spectrometry data,” Personal communication to M. Itoh, March 2000.
- N. Auner, B. Ziemer, B. Herrschaft, W. Ziche, P. John, and J. Weis, “Structural studies of novel siloxysilsesquioxanes,” European Journal of Inorganic Chemistry, vol. 1999, no. 7, pp. 1087–1094, 1999.
- T. Kudo and M. S. Gordon, “Theoretical studies of the mechanism for the synthesis of silsesquioxanes. 2. Cyclosiloxanes ( and ),” The Journal of Physical Chemistry A, vol. 104, no. 17, pp. 4058–4063, 2000.
- T. Kudo and M. S. Gordon, “Exploring the mechanism for the synthesis of silsesquioxanes. 3. The effect of substituents and water,” The Journal of Physical Chemistry A, vol. 106, no. 46, pp. 11347–11353, 2002.
- L. W. Kelts and N. J. Armstrong, “A silicon-29 NMR study of the structural intermediates in low pH sol-gel reactions,” Journal of Materials Research, vol. 4, no. 2, pp. 423–433, 1989.
- F. Brunet, “Polymerization reactions in methyltriethoxysilane studied through 29Si NMR with polarization transfer,” Journal of Non-Crystalline Solids, vol. 231, no. 1-2, pp. 58–77, 1998.
- J. F. Brown Jr., “The polycondensation of phenylsilanetriol,” Journal of the American Chemical Society, vol. 87, no. 19, pp. 4317–4324, 1965.
- D. W. Lee and Y. Kawakam, “Incompletely condensed silsesquioxanes: formation and reactivity,” Polymer Journal, vol. 39, no. 3, pp. 230–238, 2007.
- L. V. Ng, P. Thompson, J. Sanchez, C. W. Macosko, and A. V. McCormick, “Formation of cagelike intermediates from nonrandom cyclization during acid-catalyzed sol-gel polymerization of tetraethyl orthosilicate,” Macromolecules, vol. 28, no. 19, pp. 6471–6476, 1995.
- S. E. Rankin, C. W. Macosko, and A. V. McCormick, “Importance of cyclization during the condensation of hydrolyzed alkoxysilanes,” Chemistry of Materials, vol. 10, no. 8, pp. 2037–2040, 1998.