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Direct functionalization of polyisobutylene by living initiation with α-methylstyrene epoxide

Authors

  • J. Song,

    1. Macromolecular Engineering Research Center, Department of Chemical and Biochemical Engineering, University of Western Ontario, London, Ontario, Canada N6A 5B9
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  • J. Bódis,

    1. Macromolecular Engineering Research Center, Department of Chemical and Biochemical Engineering, University of Western Ontario, London, Ontario, Canada N6A 5B9
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    • J. Bódis is a visiting professor from the Department of Organic Chemistry of the Faculty of Chemistry and Chemical Engineering at Babes-Bolyai University, Arany János St. no. 11, 3400 Cluj, Romania.

  • J. E. Puskas

    Corresponding author
    1. Macromolecular Engineering Research Center, Department of Chemical and Biochemical Engineering, University of Western Ontario, London, Ontario, Canada N6A 5B9
    • Macromolecular Engineering Research Center, Department of Chemical and Biochemical Engineering, University of Western Ontario, London, Ontario, Canada N6A 5B9
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Abstract

This article describes the synthesis and characterization of polyisobutylene (PIB) carrying one primary hydroxyl head group and a tertiary chloride end group, [Ph[BOND]C(CH3)(CH2OH)–PIB–CH2[BOND]C(CH3)2Cl] prepared with direct functionalization via initiation. The polymerization of isobutylene was initiated with the α-methylstyrene epoxide/titanium tetrachloride system. Living conditions were obtained from −75 to −50 °C (198–223 K). Low molecular weight samples (number-average molecular weight ∼ 4000 g/mol) were prepared under suitable conditions and characterized by Fourier transform infrared and 1H NMR spectroscopy. The presence of primary hydroxyl head groups in PIB was verified by both methods. Quantitative Fourier transform infrared with 2-phenyl-1-propanol calibration and 1H NMR performed on both the hydroxyl-functionalized PIB and its reaction product with trimethylchlorosilane showed that each polymer chain carried one primary hydroxyl head group. The synthetic methodology presented here is an effective and simple route for the direct functionalization of PIB. © 2002 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 40: 1005–1015, 2002

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