The Halogenation of Poly[Isobutylene-CO-(2,3-Dimethyl-1,3-Butadiene)]

  • Irving Kuntz
  • Boyd E. HudsonJr.
Part of the Polymer Science and Technology book series (POLS, volume 21)

Abstract

This communication describes the halogenation of an isobutylene (B)-2,3-dimethyl-l,3-butadiene (DMB) copolymer (Structure 1) containing 1.7 mole % of units derived from the diolefin. Halogenations were carried out in hexane solutions at ambient temperatures in the dark. 13C and 1H NMR have been used to characterize the molecular details of the halogenated products. Copolymers of isobutylene with small amounts of dienes are butyl rubbers. The halogenation of the isoprene copolymer, the butyl rubber of commerce, has been well studied1,2 and Chlorobutyl and Bromobutyl are commercial products. Throughout this paper, we will compare the results obtained with the DMB and isoprene copolymers. The mechanistic aspects of the halogenations are discussed in Some detail.

Keywords

Rubber Chlorine Diene Copolymerization Bromine 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    F. P. Baldwin, D. J. Buckley, I. Kuntz and S. B. Robison, Rubber Plastics Age, 42, 500 (1961).Google Scholar
  2. 2.
    A. VanTongerloo and R. Vukov, Proc. Int. Rubber Conf., 1979, 70; Chem. Abstr., 92, 130306 (1980).Google Scholar
  3. 3.
    C. Corno, A. Priola and S. Cesca, Macromolecules, 15, 840 (1982).ADSCrossRefGoogle Scholar
  4. 4.
    R. W. Taft, J. Am. Chem. Soc., 70, 3364 (1948).CrossRefGoogle Scholar
  5. 5.
    M. L. Poutsma, Science, 157, 997 (1967).ADSCrossRefGoogle Scholar
  6. 6.
    J. D. Roberts and M. C. Caserio, “Basic Principles of Organic Chemistry” W. A. Benjamin, New York, 1964, p. 326.Google Scholar
  7. 7.
    G. A. Olah and J. M. Bollinger, J. Am. Chem. Soc., 90 6082 (1968).CrossRefGoogle Scholar
  8. 8.
    R. T. Arnold and W. W. Lee, ibid, 75, 5396 (1953).Google Scholar
  9. 9.
    J. W. Larsen and A. V. Metzner, ibid, 94, 1614 (1972).Google Scholar
  10. 10.
    G. A. Olah and T. R. Hockswender, ibid, 96, 3574 (1974).Google Scholar
  11. 11.
    J. Rehner and P. Gray, Ind. Eng. Chem., 17, 367 (1945).Google Scholar
  12. 12.
    P. J. Flory, J. Am. Chem. Soc., 65, 372 (1943).CrossRefGoogle Scholar

Copyright information

© Plenum Press, New York 1983

Authors and Affiliations

  • Irving Kuntz
    • 1
  • Boyd E. HudsonJr.
    • 2
  1. 1.Elastomers Technology Div.Exxon Chemical Co.USA
  2. 2.Analytical and Information Div.Exxon Research and Engineering Co.LindenUSA

Personalised recommendations