Skip to main content
SpringerLink
Log in

Synthesis of siloxanes containing reactive side chains

  • Symposium Paper
  • Published:
Journal of Inorganic and Organometallic Polymers Aims and scope Submit manuscript

Abstract

The synthesis and characterization of siloxanes containing methacrylate, epoxy, and amino side chains are described. Direct hydrosilylation of unsaturated methacrylate or epoxy compounds with methyl hydrogen siloxanes resulted in the attachment of methacrylate or epoxy groups as side chains on the siloxane in good yields. Amino side chains on siloxanes were formed by acidic hydrolysis of the ketenimine side chains, obtained by hydrosilylation of unsaturated ketenimines with methyl hydrogen siloxanes. Details of the preparation and characterization of such unsaturated ketenimines are reported.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. E. P. Plueddemann,Silane Coupling Agents (Plenum Press, New York, 1982).

    Google Scholar 

  2. E. P. Plueddemann,J. Adhesion 2, 184 (1970).

    Google Scholar 

  3. E. P. Plueddemann (ed.),Composite Materials, Vol. 6. Interfaces in Polymer Matrix Composites (Academic Press, New York, 1974).

    Google Scholar 

  4. P. Walker,J. Coat. Technol. 52(670), 49 (1980).

    Google Scholar 

  5. H. Ishida, inAdhesion Aspects of Polymeric Coatings, K. L. Mittal, ed. (Plenum Press, New York, 1983), pp. 45–106.

    Google Scholar 

  6. D. E. Leyden and W. Collins (eds.),Silylated Surfaces (Gordon and Breach, New York, 1980).

    Google Scholar 

  7. U. Muller, H. J. Timpe, and H. Rosler,Plaste Kautsch 34, 1134 (1987).

    Google Scholar 

  8. W. Noll,The Chemistry and Technology of Silicones (Academic Press, New York, 1968), Chap. 10.

    Google Scholar 

  9. B. Arkles,Chemtech 542 (1983).

  10. A. Berger, European Patent No. EP 14, 599 (1980).

  11. H. S. Ryang, European Patent No. EP 321, 771 (1988).

  12. K. A. Kasprzak and J. D. Blizzard, Canadian Patent No. CA 1,243,805 (1988).

  13. J. D. Cooke, B. J. Griffiths, V. B. John, and C. G. Sawicki, United States Patent No. US 4,623,794 (1986).

  14. Dow Corning, United States Patent No. US 4,290,896 (1981).

  15. R. E. Kalinowski, United States Patent No. US 4,247,592 (1981).

  16. Procter Gamble, Belgian Patent No. BE 844,200 (1977).

  17. Dow Corning, Canadian Patent No. CA 884,390 (1968).

  18. S. L. Buchwalter, R. D. Jerabek, and L. P. H. Chou, West German Patent No. DE 2,934,485 (1980).

  19. E. J. Pepe, West German Patent No. DE 2, 962, 740 (1982).

  20. F. Sardo,Am. Cosmet. Perfum. 87, 43 (1972).

    Google Scholar 

  21. Dow Corning, United States Patent No. US 3,832,203 (1974).

  22. Toray Silicones, Japanese Patent No. JP 57,11,354 (1982).

  23. E. Tolgyesi and A. F. Bresak, United States Patent No. US 4, 344, 763 (1982).

  24. G. R. Homan and J. T. Swihart, European Patent No. EP 113,992 (1983).

  25. M. H. Yang and W. C. Liaw,J. Chin. Chem. Soc. (Taipei) 35(2), 147 (1988).

    Google Scholar 

  26. P. D. George and J. R. Elliot,J. Am. Chem. Soc. 77, 3493 (1955).

    Google Scholar 

  27. E. Larsson and B. Smith,Acta Chem. Scand. 3, 487 (1949).

    Google Scholar 

  28. E. Larsson and R. Marin,Acta Chem. Scand. 5, 1173 (1951).

    Google Scholar 

  29. E. Larsson,Acta Chem. Scand. 8, 898 (1954).

    Google Scholar 

  30. K. Itoh, T. Shiobara, K. Futatsumor, K. Tomiyoshi, and H. Schimizu, European Patent No. EP 218,228 (1987).

  31. C. E. Monnier, S. A. C. Zahir, and S. H. Eldin, European Patent No. EP 205,402 (1986).

  32. A. Berger, European Patent No. EP 54,426 (1982).

  33. J. L. Webb, H. V. Ritschard, and J. M. Lambert, European Patent No. EP 342,518 (1989).

  34. T. J. Tangney and M. J. Ziemelis, United States Patent No. US 4,507,455 (1985).

  35. C. L. Lee and M. A. Lutz, European Patent No. EP 230,342 (1987).

  36. K. W. Lee, J. R. Peffer, R. Piccierilla, and W. H. Change, United States Patent No. US 4,429,082 (1984).

  37. M. J. Ziemelis, West German Patent No., DE 2,925,305 (1980).

  38. R. P. Eckberg, United States Patent No. US 4,348,454 (1982).

  39. Y. Sato and H. Inomata, West German Patent No. DE 3,006,167 (1980).

  40. G. W. Babian, M. Cully, and R. B. Metzler, European Patent No. EP 6,705 (1980).

  41. K. Shiozawa, N. Okamoto, H. Takai, Y. Okumura, K. Takatsuna, and C. Imai, European Patent No. EP 284,447 (1988).

  42. General Electric, British Patent No. GB 1,282,473 (1969).

  43. D. A. Jonas, W. J. Owen, and D. J. Cooke, British Patent No. GB 1,286,077 (1969).

  44. Stauffer Chemicals, British Patent No. GB 1,439,037 (1973).

  45. R. S. Neale,Ind. Eng. Chem. Prod. Res. Dev. 19, 639, 648 (1980).

    Google Scholar 

  46. J. S. Riffle, I. Yilgor, C. Tran, G. L. Wilkes, J. E. McGrath, and A. K. Banthia, inEpoxy Resin Chemistry II, ACS Symp. Series No. 221, R. S. Bauer (ed.), 21 (1983).

  47. W. Noll,The Chemistry and Technology of Silicones (Academic Press, New York, 1968), pp. 211–226.

    Google Scholar 

  48. S. W. Kantor, W. T. Grubb, and R. C. Osthoff,J. Am. Chem. Soc. 76, 5190 (1954).

    Google Scholar 

  49. E. P. Plueddemann and G. Fanger,J. Am. Chem. Soc. 81, 2632, (1959).

    Google Scholar 

  50. J. L. Speier, J. A. Webster, and G. H. Barnes,J. Am. Chem. Soc. 79, 974 (1957).

    Google Scholar 

  51. E. P. Plueddemann,J. Chem. Eng. Data 5, 59 (1960).

    Google Scholar 

  52. Bayer AG, French Patent No. 2, 012, 012 (1968).

  53. R. P. Eckberg and K. D. Riding, United States Patent No. US 4,783,490 (1988).

  54. R. P. Eckberg, Canadian Patent No. CA 1,218,494 (1987).

  55. L. A. Tolentino, United States Patent No. US 4,568,566 (1986).

  56. R. P. Eckberg, United States Patent No. US 4,558,082 (1985).

  57. R. H. Chung, French Patent No. FR 2,496,679 (1982).

  58. J. S. Humphrey, United States Patent No. US 4,232,088 (1980).

  59. R. L. Merker, United States Patent No. 2,833,802 (1956).

  60. R. L. Merker and J. E. Noll,J. Org. Chem. 21, 1537 (1956).

    Google Scholar 

  61. P. Rempp and E. Franta,Adv. Polym. Sci. 58, 1 (1984).

    Google Scholar 

  62. S. D. Smith, G. York, D. W. Dwight, J. E. McGrath, J. Stejskal, and P. Kratochvil,Polym. Prepr. 28(1), 458 (1987).

    Google Scholar 

  63. C. L. Lee and M. A. Lutz, European Patent No. EP 230,242 (1987).

  64. R. M. Griswold and D. G. Vanderlaan, European Patent No. EP 274,699 (1987).

  65. A. D. Petrov and S. I. Sadykh-Sade,Bull. Chim. Soc. Fr. 1932 (1959).

  66. L. Goodman, R. M. Silverstein, and A. Benitez,J. Am. Chem. Soc. 79, 3073 (1957).

    Google Scholar 

  67. B. N. Dolgov, N. P. Kharitonov, and M. G. Voronkov,J. Gen. Chem. USSR (Engl. Trans.)24, 859 (1954).

    Google Scholar 

  68. N. F. Orlov, R. A. Bogatkin, Z. I. Sergeeva, and M. G. Voronkov,J. Gen. Chem. USSR (Engl. Trans.)32, 2526 (1962).

    Google Scholar 

  69. R. N. Hazelwood, United States Patent No. US 2,727,880 (1953).

  70. R. Calas and N. Duffaunt,C.R. Hebd. Seances Acad. Sci. 245, 906 (1957).

    Google Scholar 

  71. R. Calas, E. Frainet, and J. Bonastre,C.R. Hebd. Seances Acad. Sci. 251, 2987 (1960).

    Google Scholar 

  72. R. N. Meals,Pure Appl. Chem. 13, 141 (1966).

    Google Scholar 

  73. J. L. Speier,Adv. Organomet. Chem. 17, 407 (1979).

    Google Scholar 

  74. N. S. Chu, B. Kanner, and C. L. Schilling, United States Patent No. US 4,481,364 (1984).

  75. J. M. Quirk and S. Turner, United States Patent No. US 4,556,722 (1985).

  76. G. K. I. Magomedor, K. A. Adrianov, O. V. Shkolinik, B. A. Izmailov, and V. N. Kalinin,J. Organometal. Chem. 149, 29 (1978).

    Google Scholar 

  77. V. G. Von Greber and S. Jager,Makromol. Chem. 57, 150 (1962).

    Google Scholar 

  78. M. Bergmann and A. Mickeley,Ber. Dtsch. Chem. Ges. 57, 664 (1924).

    Google Scholar 

  79. T. W. Wehrli and T. Wirthlin,Interpretation of Carbon-13 NMR Spectra (Heyden, London, 1980), pp. 174–178.

    Google Scholar 

  80. N. H. Turner, B. I. Dunlop, and R. J. Colton,Anal. Chem. 56, 373 (1984).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. School of Chemical Technology, University of South Australia, 5095, The Levels, S.A., Australia

    S. K. Duplock, J. G. Matisons, A. G. Swincer & R. F. O. Warren

Authors
  1. S. K. Duplock
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. J. G. Matisons
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. G. Swincer
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. R. F. O. Warren
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

This paper is from the Second International Topical Workshop, “Advances in Silicon-Based Polymer Science.”

Rights and permissions

Reprints and permissions

About this article

Cite this article

Duplock, S.K., Matisons, J.G., Swincer, A.G. et al. Synthesis of siloxanes containing reactive side chains. J Inorg Organomet Polym 1, 361–375 (1991). https://doi.org/10.1007/BF00702499

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00702499

Key words

Search

Navigation