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Photopolymerizable Silicone Monomers, Oligomers, and Resins

  • Anthony F. Jacobine
  • Steven T. Nakos
Part of the Topics in Applied Chemistry book series (TAPP)

Abstract

The past fifteen years has witnessed a tremendous resurgence of interest in all types of reactive silicone fluids. Imide functional siloxanes, urethane siloxanes, and a large array of silicone block copolymers are now well known and accessible by standard synthetic techniques.1–4 Research that had been previously limited to a handful of industrial laboratories, most notably General Electric, Dow Corning, and Union Carbide, has attracted the interest of the academic community as well as the interest of a host of smaller industrial organizations.5 This increase in interest in silicones has coincided with the developments in radiation-curable coatings and photopolymerization. Cross-fertilization of these two areas was inevitable.

Keywords

Fumed Silica Silicone Fluid Silicon Hydride Allyl Glycidyl Ether Moisture Cure 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    I. Yilgor, J. S. Riffle, and J. E. McGrath, in: Reactive Oligomers (F. W. Harris, ed.), ACS Symp. Ser. 282, pp. 161–174, Am. Chem. Soc, Washington, D. C. (1985).CrossRefGoogle Scholar
  2. 2.
    E. M. Yorkgitis, N. S. Eiss, C. Tran, G. W. Wilkes, and J. E. McGrath, Adv. Polym. Sci. 72, 1 (1985).CrossRefGoogle Scholar
  3. 3.
    J. D. Summers, C. S. Elsbernd, P. M. Sormani, P. J. A. Brandt, C. A. Arnold, I. Yilgor, J. S. Riffle, S. Kilic, and J. E. McGrath, in: Inorganic and Organometallic Polymers (M. Zeldin, K. Wynne, and H. R. Allcock, eds.), ACS Symp. Ser. 360, pp. 180–198, Am. Chem. Soc, Washington, D. C. (1988).CrossRefGoogle Scholar
  4. 4.
    J. V. Crivello and J. L. Lee, J. Polym. Sci.: Part A Polym. Chem. 28, 479 (1990).CrossRefGoogle Scholar
  5. 5.
    E. G. Rochow, Silicon and Silicones, Springer-Verlag, Berlin (1987).CrossRefGoogle Scholar
  6. J. E. McGrath, A. M. Hellstern, and S. D. Smith, Polym. Prepr. 28, 328 (1987).Google Scholar
  7. 6.
    E. W. Colvin, Silicon in Organic Synthesis, Butterworths, London (1981).Google Scholar
  8. 7.
    W. P. Weber, Silicon Reagents in Organic Synthesis, Springer-Verlag, Berlin (1983).CrossRefGoogle Scholar
  9. 8.
    T. C. Ward, D. P. Sheehy, J. S. Riffle, and J. E. McGrath, Macromolecules 14, 1791 (1981).CrossRefGoogle Scholar
  10. 9.
    Y. Gnanou and P. Rempp, Makromol. Chem. 189, 1997 (1988).CrossRefGoogle Scholar
  11. 10.
    S. W. Bany, R. J. Koshar, and T. R. Williams (Minnesota Mining and Manufacturing Co.) U. S. Patent 4,543,398 (1985).Google Scholar
  12. 11.
    Y. Okamoto, D. Crossan, K. Ferrigno, and S. Nakos, in: Adhesives, Sealants and Coatings for Space and Harsh Environments, Plenum Press, New York (1988).Google Scholar
  13. 12.
    I. D. Grossan and J. J. Heaton, Proceedings of the 20th Annual Connectors and Interconnection Technology Symposium, Philadelphia, October (1987).Google Scholar
  14. 13.
    L. A. Tolentino (General Electric Co.) U. S. Patent 4,568,566 (1986).Google Scholar
  15. 14.
    W. L. Liu and J. D. Rich (General Electric Co.) U. S. Patent 4,563,514 (1986).Google Scholar
  16. 15.
    U. Mueller, H. J. Timpe, and H. Roesler, Plaste Kautsch. 34, 183 (1987).Google Scholar
  17. 16.
    R. Eckberg, Radcure ′84 Conf Proc, p. 2–1, Soc Manuf. Eng., Dearborn, Mich. (1984).Google Scholar
  18. 17.
    P. J. Varaprath and A. P. Wright, Polym. Prepr. 29, 534 (1988).Google Scholar
  19. 18.
    P. J. Varaprath, A. P. Wright, and J. R. Keryk, Radcure ′88 Conf. Proc, p. 16–29, Soc. Manuf. Eng., Dearborn, Mich. (1988).Google Scholar
  20. 19.
    F. S. Kipping and L. L. Loyd, J. Chem. Soc. 79, 449 (1901).CrossRefGoogle Scholar
  21. 20.
    F. S. Kipping, Proc. R. Soc. London Ser. A 159, 139 (1937).CrossRefGoogle Scholar
  22. 21.
    R. J. H. Voorhoere, Organohalosilanes: Precursors to Silicones, Elsevier, Amsterdam (1967).Google Scholar
  23. 22.
    F. O. Stark, J. R. Falender, and A. P. Wright, Comprehensive Organometallic Chemistry 2 (G. Wilkinson, ed.), Pergamon Press, Elmsford, N. Y. (1982).Google Scholar
  24. 23.
    B. B. Hardman and A. Torkelson, Encyclopedia of Chemical Technology, 3rd ed., Vol. 20, Wiley, New York (1982).Google Scholar
  25. 24.
    E. M. Valles and C. W. Macosko, Macromolecules 12, 521 (1979).CrossRefGoogle Scholar
  26. E. M. Valles and C. W. Macosko, Macromolecules 12, 673 (1979)CrossRefGoogle Scholar
  27. W. J. MacKnight and D. Chundury, Polym. Prepr. 24(2), 67 (1983).Google Scholar
  28. 25.
    B. Arkles, Chemtech 13, 542 (1983).Google Scholar
  29. 26.
    S. A. Braley, J. Macromol. Sci. Chem. 4, 529 (1970).CrossRefGoogle Scholar
  30. 27.
    S. A. Braley, Modern Trends in Biomechanics 1, Butterworths, London (1970).Google Scholar
  31. 28.
    N. S. Gaylord [Syntex (USA), Inc.] U. S. Patent 4,120,570 (1978); N. S. Gaylord, (Polycon Laboratories, Inc.) U. S. Patent 3,808,178 (1974).Google Scholar
  32. 29.
    D. B. Bailey, R. C. Daley, T. B. Brust, and J. M. Pearson, Polymers for Advanced Technology, IUPAC Int. Symp. (M. Lewin, ed.), VCH Publishers, New York (1988).Google Scholar
  33. 30.
    J. Ackermann and V. Damrath, Chem. Unserer Zeit 23(3), 86 (1989).CrossRefGoogle Scholar
  34. 31.
    S. Boileau, Anionic Polymerizations of Cyclosiloxanes (J. E. McGrath, ed.), ACS Symp. Ser. 286, p. 94, Am. Chem. Soc, Washington, D. C. (1985).Google Scholar
  35. 32.
    J. E. McGrath, J. S. Riffle, A. K. Banthia, I. Yilgor, and G. W. Wilkes, An Overview of the Polymerization of Cyclosiloxanes (F. E. Bailey, ed.), ACS Symp. Ser. 212, p. 94, Am. Chem. Soc, Washington, D. C. (1983).Google Scholar
  36. 33.
    G. G. Cameron and M. S. Chisholm, Polymer 26, 437 (1985).CrossRefGoogle Scholar
  37. 34.
    A. L. Smith, Analysis of Silicones, Wiley, New York (1974).Google Scholar
  38. 35.
    P. J. Andolino Brandt, R. Subramian, P. M. Sormani, T. C. Ward, and J. E. McGrath, Polym. Prepr. 26(2), 213 (1985).Google Scholar
  39. 36.
    M. D. Beers (General Electric Co.) U. S. Patent 3,382,205 (1968).Google Scholar
  40. 37.
    P. P. Peyrot and L. J. Doumoulin (Rhone-Poulenc, Inc.) U. S. Patent 2,615,861 (1952).Google Scholar
  41. 38.
    D. Golitz, K. Damm, R. Muller, and W. Noll (Farbenfab. Bayer A. G.) U. S. Patent 3,417,047 (1968).Google Scholar
  42. 39.
    A. R. Weyenberg (Dow Corning Corp.) U. S. Patent 3,334,067 (1968).Google Scholar
  43. 40.
    S. D. Smith and S. B. Hamilton, Jr. (General Electric Co.) U. S. Patent 3,689,454 (1972).Google Scholar
  44. 41.
    B. B. Hardman and W. T. Madigan (General Electric Co.) U. S. Patent 4,036,813 (1977).Google Scholar
  45. 42.
    M. D. Beers (General Electric Co.) U. S. Patent 4,100,129 (1978).Google Scholar
  46. 43.
    C. Millet, U. S. Patent 4,849,388 (Rhone-Poulenc Specialties Chimiques) (1989).Google Scholar
  47. 44.
    T. Takago (Shin-Etsu Chemical Co.) U. S. Patent 4,180,642 (1980).Google Scholar
  48. 45.
    R. H. Chung (General Electric Co.) U. S. Patent 4,839,453 (1989).Google Scholar
  49. 46.
    J. E. Mark, Rubber Chem. Technol. 48, 495 (1975).CrossRefGoogle Scholar
  50. 47.
    N. R. Langley and K. E. Polmanteer, J. Polym. Sci. Polym. Phys. Ed. 12, 1023 (1974).CrossRefGoogle Scholar
  51. 48.
    J. R. Falender, Polym. Prepr. 20(2), 467 (1979).Google Scholar
  52. 49.
    S. Nitzsche and M. Wick, Kunststoffe Bd. 47, 431 (1957).Google Scholar
  53. 50.
    M. Hatanaka and A. Kurita (General Electric Co.) U. S. Patent 4,451,634 (1984).Google Scholar
  54. 51.
    T. Komai and M. Shimizu (Nippon Oil and Fats Co., Ltd.) U. S. Patent 4,777,191 (1988).Google Scholar
  55. 52.
    F. Samu, A. Kurita, and Y. Matsumoto (Toshiba Silicone K. K.) Jpn. Kokai Tokkyo Koho 62, 290755 (1987).Google Scholar
  56. 53.
    M. E. Nelson (Dow Corning Corp.) U. S. Patent 3,020,260 (1962).Google Scholar
  57. 54.
    A. E. Chalk (General Electric Co.) U. S. Patent 3,334,111 (1967).Google Scholar
  58. 55.
    M. Gottleib, C. W. Macosko, and T. C. Lepsch, J. Polym. Sci. Polym. Phys. 19, 1603 (1981).CrossRefGoogle Scholar
  59. 56.
    Anon., “Two Component RTV Silicone Rubber Compounds for Industrial Applications, S35-B,” General Electric Co., Waterford, N. Y. (1980).Google Scholar
  60. 57.
    B. Karstedt (General Electric Co.) U. S. Patent 3,775,452 (1973).Google Scholar
  61. 58.
    L. N. Lewis and N. Lewis, J. Am. Chem. Soc. 108, 7228 (1986).CrossRefGoogle Scholar
  62. 59.
    L. N. Lewis (General Electric Co.) U. S. Patent 4,645,815 (1987).Google Scholar
  63. 60.
    J. L. Speier, Adv. Organomet. Chem. 17, 407 (1979).CrossRefGoogle Scholar
  64. 61.
    V. J. Eddy and J. E. Hallgren, J. Org. Chem. 52, 1903 (1987).CrossRefGoogle Scholar
  65. 62.
    E. Lukevics, Russ. Chem. Rev. 46, 264 (1977).CrossRefGoogle Scholar
  66. 63.
    A. E. Chalk and J. F. Harrod, J. Am. Chem. Soc. 86, 1776 (1964).CrossRefGoogle Scholar
  67. 64.
    A. E. Chalk and J. F. Harrod, J. Am. Chem. Soc. 87, 1133 (1965).CrossRefGoogle Scholar
  68. 65.
    K. A. Brady and T. A. Nile, J. Organomet. Chem. 206, 299 (1981).CrossRefGoogle Scholar
  69. 66.
    H. Aoki, Y. Hara, and K. Kondow, Eur. Pat. Appl. 238,033 (Sept. 23, 1987).Google Scholar
  70. 67.
    S. Sasaki and Y. Hamada, Eur. Pat. Appl. 153,700 (Sept. 4, 1985).Google Scholar
  71. 68.
    G. K. Kookotsedes and E. P. Pluddemann (Dow Corning Corp.) U. S. Patent 3,445,420 (1969).Google Scholar
  72. 69.
    T. R. Williams, J. Appl. Polym. Sci. 31, 1293 (1986).CrossRefGoogle Scholar
  73. 70.
    A. F. Jacobine and D. M. Glaser (Loctite Corp.) U. S. Patent 4,640,940 (1987).Google Scholar
  74. 71.
    G. A. Gornowicz, T. A. Tangney, and M. J. Ziemelis (Dow Corning Corp.) U. S. Patent 4,563,539 (1986).Google Scholar
  75. 72.
    E. P. Pluddemann and H. A. Clark (Dow Corning Corp.) Belgian Patent 613,466 (1962).Google Scholar
  76. 73.
    S. Berg, V. Krone, and H. Ringsdorf, Makromol. Chem. Rapid Commun. 7, 381 (1986).CrossRefGoogle Scholar
  77. 74.
    G. W. Gray, D. Lacey, G. Nestor, and C. B. McArdle (General Electric Co.) Eur. Pat. Appl. 260,786 (March 23, 1988).Google Scholar
  78. 75.
    T. Imai and N. Koide (Toray Silicone Co., Ltd.) U. S. Patent 4,774,028 (1988).Google Scholar
  79. 76.
    G. Marignan, D. Teyssie, S. Boileau, J. Malthete, and C. Noel, Polymer 29, 1318 (1988).CrossRefGoogle Scholar
  80. 77.
    J. D. Nordstrom (Ford Werke A. G.) Ger. Offen. DE 2063134 (1971).Google Scholar
  81. 78.
    J. D. Nordstrom and C. Zelek (Ford Werke A. G.) Ger. Offen. DE 32063256 (1971).Google Scholar
  82. 79.
    J. D. Nordstrom and C. Zelek (Ford Werke A. G.) Ger. Offen. DE 2063135 (1971).Google Scholar
  83. 80.
    A. Jaeger, H. Kochs, A. Rosenberg, and H. Heusinger, Farbe Lack 88, 632 (1982).Google Scholar
  84. 81.
    D. J. Cyterski, in Ref. 16, p. 2-19.Google Scholar
  85. 82.
    G. A. H. Kupfer, DPW, Dtsch. Papierwirtsch. 2, 184 (1984).Google Scholar
  86. 83.
    Anon. (Toray Silicone Co., Ltd.) Jpn. Kokai Tokkyo Koho 60,71664 (1985).Google Scholar
  87. 84.
    S. Sasaki and Y. Hamada (Toray Silicone Co., Ltd.) Eur. Pat. Appl. EP 184598 (1986).Google Scholar
  88. 85.
    S. W. Bany and L. E. Wood (Minnesota Mining and Manufacturing Co.) U. S. Patent 4,677,137 (1987).Google Scholar
  89. 86.
    J. P. Cohen-Addad, P. Huchot, P. Jost, and A. Pouchelon, Polymer 30, 143 (1989).CrossRefGoogle Scholar
  90. 87.
    J. E. Mark, Chemtech 19(4), 230 (1989).Google Scholar
  91. 88.
    G. A. L. Gant (Dow Corning Corp.) U. S. Patent 4,064,027 (1977).Google Scholar
  92. 89.
    B. B. Boonstra, H. Cochrane, and E. M. Dannenberg, Rubber Chem. Technol. 48, 558 (1975).CrossRefGoogle Scholar
  93. 90.
    M. D. Beers (General Electric Co.) U. S. Patent 3,837,878 (1984).Google Scholar
  94. 91.
    J. Edwards, S. Lenon, A. F. Toussaint, and B. Vincent, in: Polymer Absorption and Dispersion Stability (E. D. Goddard and B. Vincent, eds.), ACS Symp. Ser. 240, pp. 281–296, Am. Chem. Soc, Washington, D. C. (1984).Google Scholar
  95. 92.
    M. Matsumoto (General Electric Co.) U. S. Patent 4,469,522 (1984).Google Scholar
  96. 93.
    K. M. Lee and K. L. Ulman (Dow Corning Corp.) U. S. Patent 4,454,288 (1984).Google Scholar
  97. 94.
    X. Wu, G. Shubang, and Z. Yuanmin, Acta Mater. Compos. Sin. 2(4), 1 (1985).Google Scholar
  98. 95.
    G. W. Sears, Jr., Anal Chem. 28, 1981 (1956).CrossRefGoogle Scholar
  99. 96.
    K. E. Polmanteer and C. W. Lentz, Rubber Chem. Technol. 48, 558 (1975).CrossRefGoogle Scholar
  100. 97.
    R. Mercier, X. Coqueret, A. Lablache-Combier, and C. Loucheux, Eur. Polym. J. 24(7), 639 (1988).CrossRefGoogle Scholar
  101. 98.
    P. Klemarczyk, S. T. Nakos, and S. Q. S. Lin (Loctite Corp.) U. S. Patent 4,666,953 (1987).Google Scholar
  102. 99.
    S. Q. S. Lin (Loctite Corp.) U. S. Patent 4,477,326 (1984).Google Scholar
  103. 100.
    S. Q. S. Lin and R. W. Humphreys (Loctite Corp.) U. S. Patent 4,587,276 (1986).Google Scholar
  104. 101.
    A. F. Jacobine and S. Q. S. Lin (Loctite Corp.) U. S. Patent 4,507,187 (1985).Google Scholar
  105. 102.
    A. F. Jacobine, S. Q. S. Lin, and L. Fabrizio (Loctite Corp.) U. S. Patent 4,536,265 (1985).Google Scholar
  106. 103.
    S. Q. S. Lin and A. F. Jacobine (Loctite Corp.) U. S. Patent 4,534,838 (1985).Google Scholar
  107. 104.
    A. Shirahata (Toray Silicone Co., Ltd.) U. S. Patent 4,391,963 (1983).Google Scholar
  108. 105.
    B. A. Ashby and S. H. Schroeter (General Electric Co.) U. S. Patent 4,436,924 (1984).Google Scholar
  109. 106.
    A. Shirahata and K. Kishimoto (Toray Silicone Co., Ltd.) Eur. Pat. Appl. EP 88842 (1983).Google Scholar
  110. 107.
    M. Takamizawa and A. Yamamoto (Shin-Etsu Chemical Co., Ltd.) Jpn. Kokai JP 53071199 (1978).Google Scholar
  111. 108.
    H. A. Vaughan, Jr. (General Electric Co.) U. S. Patent 4,436,851 (1984).Google Scholar
  112. 109.
    N. S. Chu and L. Mariin (Union Carbide Corp.) U. S. Patent 4,430,235 (1984).Google Scholar
  113. 110.
    R. P. Eckberg and R. W. LaRochelle (General Electric Co.) U. S. Patent 4,279,717 (1981).Google Scholar
  114. 111.
    R. P. Eckberg (General Electric Co.) U. S. Patent 4,547,431 (1985).Google Scholar
  115. 112.
    R. P. Eckberg (General Electric Co.) U. S. Patent 4,558,082 (1985).Google Scholar
  116. 113.
    R. P. Eckberg (General Electric Co.) U. S. Patent 4,640,967 (1987).Google Scholar
  117. 114.
    R. P. Eckberg and K. D. Riding, in: Radiation Curing of Polymeric Materials (C. E. Hoyle and J. F. Kinstle, eds.), ACS Symp. Ser. 417, p. 382, Am. Chem. Soc, Washington, D. C. (1990).Google Scholar
  118. 115.
    J. V. Crivello and J. L. Lee, Polym. Mater. Sci. Eng. Prepr. 60, 217 (1989).Google Scholar
  119. 116.
    R. P. Eckberg and K. D. Riding, Polym. Mater. Sci. Eng. Prepr. 60, 222 (1989).Google Scholar
  120. 117.
    Y. Kondo (Shin-Etsu Chemical Co, Ltd.) Jpn. Kokai Tokkyo Koho 60,179417 (1985).Google Scholar
  121. 118.
    A. B. Pudder and W. E. Willy (Uvexs Inc.) Eur. Pat. Appl. EP 222582 (1987).Google Scholar
  122. 119.
    I. Ona, M. Ozaki, and T. Fujii (Toray Silicone Co., Ltd.) Eur. Pat. Appl. EP 193402 (1986).Google Scholar
  123. 120.
    R. H. Chung (General Electric Co.) U. S. Patent 4,486,504 (1984).Google Scholar
  124. 121.
    U. Deschler, A. Grund, and G. Prescher (Degussa, A. G.) U. S. Patent 4,705,868 (1987).Google Scholar
  125. 122.
    J. G. Woods and J. M. Rooney (Loctite Corp.) U. S. Patent 4,640,849 (1987).Google Scholar
  126. 123.
    J. G. Woods, J. M. Rooney, and S. J. Harris (Loctite Corp.) U. S. Patent 4,543,397 (1985).Google Scholar
  127. 124.
    J. March, Advanced Organic Chemistry: Reactions, Mechanism, and Structure, McGraw-Hill, New York (1968).Google Scholar
  128. 125.
    W. A. Mazieka and H. M. Neumann, Inorg. Chem. 5, 309 (1966).CrossRefGoogle Scholar
  129. 126.
    G. E. LeGrow (Dow Corning Corp.) U. S. Patent 3,655,713 (1972).Google Scholar
  130. 127.
    G. Preiner, F. Hockemeyer, and C. Burger (Wacker-Chemie GmbH) U. S. Patent 4,861,807 (1989).Google Scholar
  131. 128.
    R. V. Viventi (General Electric Co.) U. S. Patent 3,816,282 (1974).Google Scholar
  132. 129.
    K. W. Michael, A. E. Mink, and D. D. Mitchell (Dow Corning Corp.) U. S. Patent 3,873,499 (1975).Google Scholar
  133. 130.
    Y. Inoue and M. Arai (Shin-Etsu Chemical Co., Ltd.) U. S. Patent 4,742,092 (1988).Google Scholar
  134. 131.
    M. Arai, N. Sato, and I. Fujioka (Shin-Etsu Chemical Co., Ltd.) Jpn. Kokai Tokkyo Koho 63,010632 (1988).Google Scholar
  135. 132.
    W. J. S. Steinkraus, J. G. Woods, J. M. Rooney, A. F. Jacobine, and D. M. Glaser (Loctite Corp.) Int. Pat. Appl. WO 88/02902 (1988).Google Scholar
  136. 133.
    A. F. Jacobine, D. M. Glaser, and S. T. Nakos, Polym. Mater. Sci. Eng. Prepr. 60, 211 (1989).Google Scholar
  137. 134.
    M. A. Lutz, R. S. Reaoch, and P. E. Reedy, Jr. (Dow Corning Corp.) U. S. Patent 4,816,497 (1989).Google Scholar
  138. 135.
    C. L. Lee and M. A. Lutz (Dow Corning Corp.) U. S. Patent 4,780,486 (1988).Google Scholar
  139. 136.
    G. R. Horman and C. L. Lee (Dow Corning Corp.) U. S. Patent 4,066,603 (1978).Google Scholar
  140. 137.
    D. J. Gordon and M. J. Ziemelis (Dow Corning Corp.) U. S. Patent 4,107,390 (1978).Google Scholar
  141. 138.
    C. R. Morgan and D. R. Kyle, J. Radiat. Curing 10(4), 4 (1983).Google Scholar
  142. 139.
    C. R. Morgan, F. Magnotta, and A. D. Ketley, J. Polym. Sci. Polym. Chem. Ed. 15, 627 (1977).CrossRefGoogle Scholar
  143. 140.
    C. L. Lee and M. A. Lutz (Dow Corning Corp.) Eur. Pat. Appl. EP 141380 (1985).Google Scholar
  144. 141.
    C. W. Macosko, Br. Polym. J. 17, 239 (1985).CrossRefGoogle Scholar
  145. 142.
    O. Girard, A. Guillermo, and J. P. Cohen-Addad, Makromol Chem. Macromol. Symp. 30, 69 (1989).CrossRefGoogle Scholar
  146. 143.
    W. Noll, Chemistry and Technology of Silicones, Academic Press, New York (1968).Google Scholar
  147. C. C. Sun and J. E. Mark, Polymer 30, 104 (1989).CrossRefGoogle Scholar
  148. 144.
    E. P. Plueddemann and H. M. Bank (Dow Corning Corp.) U. S. Patent 4,798,889 (1989).Google Scholar
  149. 145.
    U. Muller, B. Strehmel, and J. Neuenfeld, Makromol. Chem. Rapid Comh an. 10, 539 (1989).CrossRefGoogle Scholar
  150. 146.
    S. Q. S. Lin and S. T. Nakos (Loctite Corp.) U. S. Patent 4,675,346 (1987).Google Scholar
  151. 147.
    B. Boutevin, F. Guida-Pietrasanta, and J. J. Robin, Makromol. Chem. 190, 2437 (1989).CrossRefGoogle Scholar
  152. 148.
    J. L. Speier, J. A. Websterr, and G. H. Barnes, J. Am. Chem. Soc. 79, 974 (1957).CrossRefGoogle Scholar
  153. 149.
    M. Kawashima, I. Komura, and J. Yamauchi (Kuraray Co., Ltd.) Jpn. Kokai Tokkyo Koho 01,050888 (1989).Google Scholar
  154. 150.
    H. K. Chu, M. D. Johnson, and C. L. Frye, J. Organomet. Chem. 271, 327 (1984).CrossRefGoogle Scholar
  155. 151.
    S. K. Chaudhary and O. Hernandez, Tetrahedron Lett., 99 (1979).Google Scholar
  156. 152.
    M. J. Ziemelis and J. C. Saam, Macromolecules 22, 2111 (1989).CrossRefGoogle Scholar
  157. 153.
    R. L. Merker (Dow Corning Corp.) U. S. Patent 2,793,223 (1957).Google Scholar
  158. 154.
    E. R. Martin (Stauffer Chemical Co.) U. S. Patent 3,878,263 (1975).Google Scholar
  159. 155.
    W. G. Deichert, Kai C. Su, M. Van Buren (Bausch & Lomb Inc.) U. S. Patent 4,195,030 (1980).Google Scholar
  160. 156.
    J. L. Speier (Dow Corning Corp.) U. S. Patent 2,906,735 (1959).Google Scholar
  161. 157.
    R. L. Merker (Dow Corning Corp.) U. S. Patent 2,922,807 (1960).Google Scholar
  162. 158.
    R. L. Merker (Dow Corning Corp.) U. S. Patent 2,956,044 (1960).Google Scholar
  163. 159.
    G. Koerner, V. Kropac, and C. Weitemeyer (Th. Goldschmidt A. G.) U. S. Patent 4,306,050 (1981).Google Scholar
  164. 160.
    S. Q. S. Lin and S. T. Nakos (Loctite Corp.) U. S. Patent 4,504,629 (1985).Google Scholar
  165. 161.
    J. D. Nordstrom (Ford Motor Co.) U. S. Patent 3,746,567 (1973).Google Scholar
  166. 162.
    A. Noshay and M. Matzner, Angew. Makromol. Chem. 37, 215 (1974).CrossRefGoogle Scholar
  167. 163.
    H. A. Vaughn, Jr. (General Electric Co.) U. S. Patent 3,189,662 (1965).Google Scholar
  168. 164.
    F. D. Mendecino (Union Carbide Corp.) U. S. Patent 4,083,856 (1978).Google Scholar
  169. 165.
    G. C. Johnson and R. B. Meltzer (Union Carbide Corp.) U. S. Patent 4,046,930 (1977).Google Scholar
  170. 166.
    R. G. Carter, A. N. Pines, and S. L. Watson (Union Carbide Corp.) U. S. Patent 4,293,678 (1981).Google Scholar
  171. 167.
    F. Fekete, P. J. Keeman, and W. J. Plant (H. H. Robertson Co.) U. S. Patent 3,373,075 (1968).Google Scholar
  172. 168.
    Y. Sato and H. Inomata (Shin-Etsu Chemical Co.) U. S. Patent 4,293,397 (1981).Google Scholar
  173. 169.
    J. G. Marsden and S. Sterman (Union Carbide Corp.) U. S. Patent 3,555,051 (1971).Google Scholar
  174. 170.
    X. Yu, M. R. Nagarajan, C. Li, T. A. Speckhard, and S. L. Cooper, J. Appl. Polym. Sci. 30, 2115 (1985).CrossRefGoogle Scholar
  175. 171.
    J. K. Rasmussen, S. M. Heilmann, and F. J. Palensky (Minnesota Mining and Manufacturing Co.) U. S. Patent 4,777,276 (1988).Google Scholar
  176. 172.
    J. K. Rasmussen, A. R. Katritzky, L. R. Krepski, H. K. Smith, S. M. Heilmann, and K. Sakizadeh (Minnesota Mining and Manufacturing Co.) U. S. Patent 4,785,070 (1988).Google Scholar
  177. 173.
    W. Y. Chiang and W. J. Shu, Angew. Makromol. Chem. 160, 41 (1988).CrossRefGoogle Scholar
  178. 174.
    R. G. Carter, W. P. Miller, and S. L. Watson (Union Carbide Corp.) U. K. Patent Appl. 2,067,213 (1980).Google Scholar
  179. 175.
    P. Y. K. Lo and M. J. Ziemelis (Dow Corning Corp.) Eur. Patent Appl. 271,979 (1987).Google Scholar
  180. 176.
    R. Wachowiak and K. Connors, Anal. Chem. 57(1), 27 (1979).CrossRefGoogle Scholar
  181. 177.
    S. Q. S. Lin and S. T. Nakos (Loctite Corp.) U. S. Patent 4,503,208 (1985).Google Scholar
  182. 178.
    R. M. Griswold, W. L. Magee, and P. A. Manis (SWS Silicones Corp.) U. S. Patent 4,606,933 (1986).Google Scholar
  183. 179.
    C. Lee and M. A. Lutz (Dow Corning Corp.) U. S. Patent 4,849,461 (1989).Google Scholar
  184. 180.
    P. Y. K. Lo and M. J. Ziemelis (Dow Corning Corp.) Eur. Pat. Appl. 267003 (1988).Google Scholar
  185. 181.
    C. Lee and M. A. Lutz (Dow Corning Corp.) U. S. Patent 4,697,026 (1987).Google Scholar
  186. 182.
    S. T. Nakos and S. Q. S. Lin (Loctite Corp.) U. S. Patent 4,699,802 (1987).Google Scholar
  187. 183.
    Q. S. Lien and S. T. Nakos, U. S. Patent 4,528,081 assigned to Loctite Corp. (1985).Google Scholar
  188. 184.
    N. S. Chu and B. Kanner (Union Carbide Corp.) U. S. Patent 4,709,067 (1987).Google Scholar
  189. 185.
    S. E. Berger and T. C. Williams (Union Carbide Corp.) U. S. Patent 3,726,710 (1973).Google Scholar
  190. 186.
    Y. Sato, H. Inomata, and H. Okinoshima (Shin-Etsu Chemical Co., Ltd.) U. S. Patent 4,364,809 (1982).Google Scholar
  191. 187.
    R. P. Eckberg (General Electric Co.) U. S. Patent 4,585,669 (1986).Google Scholar
  192. 188.
    R. L. Yates, J. Catal. 78, 111 (1982).CrossRefGoogle Scholar
  193. 189.
    R. G. Austin, R. S. Paonessa, P. J. Giordano, and M. S. Wrighton, in: Inorg. Organomet. Photochem., Adv. Chem. Ser. 168, p. 189, Am. Chem. Soc, Washington, D. C. (1978).Google Scholar
  194. 190.
    T. Drahnak (Minnesota Mining and Manufacturing Co.) U. S. Patent 4,510,094 (1985), 4,600,484 (1986).Google Scholar
  195. 191.
    S. Sasaki and Y. Hamada (Toray Silicone Co., Ltd.) Eur. Pat. Appl. EP 153700 (1985).Google Scholar
  196. 192.
    R. P. Eckberg (General Electric Co.) U. K. Pat. Appl. 2,198,740 A (1989).Google Scholar
  197. 193.
    J. Cavezzan (Rhone-Poulenc Specialties Chimiques) U. S. Patent 4,595,739 (1986).Google Scholar
  198. 194.
    W. G. Deichert (Bausch and Lomb, Inc.) U. S. Patent 4,780,515 assigned to (1988).Google Scholar
  199. 195.
    D. J. Ratkowski (Paragon Optical, Inc.) U. S. Patent 4,769,431 (1988).Google Scholar
  200. 196.
    D. J. Ratkowski and P. C. Lue (Paragon Optical, Inc.) U. S. Patent 4,535,138 (1985).Google Scholar
  201. 197.
    D. R. Chapman (Fused Kontacts of Chicago) U. S. Patent 4,709,066 (1987).Google Scholar
  202. 198.
    Y. Mizutani, T. Harata, and G. Tanahashi (Nippon Contact Lens, Inc.) U. S. Patent 4,743,667 (1988).Google Scholar
  203. 199.
    W. M. Foley (John D. McCarry) U. S. Patent 4,507,452 (1985).Google Scholar
  204. 200.
    D. Lim and C. L. Kulkarni (Barnes-Hind, Inc.) U. S. Patent 4,861,840 (1989).Google Scholar
  205. 201.
    E. J. Ellis (Polymer Technology Corp.) U. S. Patent 4,826,936 (1989).Google Scholar
  206. 202.
    W. M. Foley, Jr. (W. M. Foley, Jr.) U. S. Patent 4,780,516 (1988).Google Scholar
  207. 203.
    E. Masuhara, N. Tammi, and M. Tsuchiya (Hoya Lens KK) French Patent Appl. 2,407,232 (1979).Google Scholar
  208. 204.
    R. Chen (Bausch & Lomb, Inc.) U. S. Patent 4,143,949 (1979).Google Scholar
  209. 205.
    B. Deubzer, J. Burkhardt, E. Brunner, and K. Sallersbeck (Wacker Chemie, GmbH) Ger. Offen. DE 2,917,754 (1980).Google Scholar
  210. 206.
    G. D. Friends and J. F. Kunzler (Bausch & Lomb, Inc.) U. S. Patent 4,810,764 (1989).Google Scholar
  211. 207.
    G. D. Friends, J. B. Melpolder, J. F. Kunzler, and J. S. Park (Bausch & Lomb, Inc.) U. S. Patent 4,652,622 (1987).Google Scholar
  212. 208.
    J. J. Falcetta (Alcon Laboratories, Inc.) U. S. Patent 4,737,558 (1988).Google Scholar
  213. 209.
    T. Uemiya, Y. Osawa, S. Niwa, and Y. Shibata (Sumitomo Electric Industries, Ltd.) U. S. Patent 4,780,510 (1988).Google Scholar
  214. 210.
    A. Kobayashi, T. Fujita, T. Saito, H. Kawai, Y. Hosoi, and H. Shibata (Hitachi Chemical Co., Ltd.) U. S. Patent 4,868,261 (1989).Google Scholar
  215. 211.
    W. G. Deichert, K. C. Su, and M. F. Van Buren (Bausch & Lomb, Inc.) U. S. Patent 4,189,546 (1980).Google Scholar
  216. 212.
    K. F. Mueller and P. Harisiades (Ciba-Geigy Corp.) U. S. Patent 4,837,289 (1989).Google Scholar
  217. 213.
    R. Pierson, Adhes. Age 52(4), 28 (1989).Google Scholar
  218. 214.
    J. G. Kloosterboer, Adv. Polym. Sci. 84(1), 18 (1987).Google Scholar
  219. 215.
    C. L. Lee and M. A. Lutz (Dow Corning Corp.) U. S. Patent 4,780,486 (1988).Google Scholar
  220. 216.
    G. J. Dehli, C. L. Lee, M. A. Lutz, and T. Suzuki, Mater. Res. Soc. Symp. Proc. 88 (Opt. Fiber Mater. Prop.), 11 (1987).Google Scholar
  221. 217.
    F. Zapf, H. Markert, B. Stapp, C. Weitemeyer, and D. Wewers, Polym. Prepr. 30(2), 107 (1989).Google Scholar
  222. 218.
    J. N. Clark, C. L. Lee, and M. A. Lutz, Polym. Mater. Sci. Eng. Prepr. 52, 442 (1985).Google Scholar
  223. 219.
    S. Okagawa and M. Nishimura (Furukawa Electric Co.) Jpn. Kokai JP 61170711 (1986).Google Scholar
  224. 220.
    M. A. Lutz and K. A. Scheibert, in: Polymeric Materials for Electronics Packaging and Interconnection (J. H. Lupinski and R. S. Moore, eds.), ACS Symp. Ser. 407, p. 275, Am. Chem. Soc, Washington, D. C. (1989).Google Scholar
  225. 221.
    G. Priener and K. Matejcek (Wacker-Chemie GmbH) Ger. Offen. DE 3,433,654 (1986).Google Scholar
  226. 222.
    N. Hayashi (Toshiba Silicone K. K.) Jpn. Kokai Tokkyo Koho 62,292867 (1987).Google Scholar
  227. 223.
    R. Pigeon (Rhone-Poulenc Specialties Chimiques) U. K. Patent Appl. GB 2,101,150 (1983).Google Scholar
  228. 224.
    T. Suzuki and M. Yoshitake (Toray Silicone Co., Ltd.) U. S. Patent 4,777,233 (1988).Google Scholar
  229. 225.
    M. Takamizawa (Shinetsu Kagaku Kogyo K. K.) Jpn. Patent Appl. Kokai 34,291/76 (1976).Google Scholar
  230. 226.
    C. B. Friedlander and J. C. McMullen (PPG Industries, Inc.) U. S. Patent 4,130,708 (1978).Google Scholar
  231. 227.
    C. L. Lee and W. B. Shyu (Dow Corning Corp.) U. S. Patent 4,600,751 (1986).Google Scholar
  232. 228.
    Y. Yamamoto, H. Fujiki, H. Kato, and A. Yoshida (Shin-Etsu Chemical Co., Ltd.) U. S. Patent 4,742,177 (1988).Google Scholar
  233. 229.
    T. Kajima, T. Swada, S. Ryuzaki, and Y. Yoshino (Matsushita Electric Industrial Co., Ltd.) Jpn. Kokai JP 62125825 (1987).Google Scholar
  234. 230.
    C. Weitemeyer, J. Jachmann, D. Allstadt, and H. Brus, Pigm. Resin Technol. 17(11), 7 (1988).CrossRefGoogle Scholar
  235. 231.
    M. Cully, A. N. Pines, R. B. Metzler, and G. W. Babian (Union Carbide Corp.) U. S. Patent 4,201,808 (1980).Google Scholar
  236. 232.
    J. E. Gaske and N. T. Georgas (DeSoto, Inc.) U. S. Patent 4,016,333 (1977).Google Scholar
  237. 233.
    R. J. Koshar and S. W. Bany (Minnesota Mining and Manufacturing Co.) U. S. Patent 4,313,988 (1982).Google Scholar
  238. 234.
    J. D. Blizzard and T. J. Swihart (Dow Corning Corp.) U. S. Patent 4,591,622 (1986). 235. W. H. Daudt and L. J. Tyler (Dow Corning Corp.) U. S. Patent 2,676,182 (1954).Google Scholar
  239. 236.
    D. O. Ethier (LecTec Corp.) U. S. Patent 4,696,854 (1987).Google Scholar

Copyright information

© Springer Science+Business Media New York 1992

Authors and Affiliations

  • Anthony F. Jacobine
    • 1
  • Steven T. Nakos
    • 1
  1. 1.Chemical and Materials Science GroupLoctite CorporationNewingtonUSA

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