Get access

Selective polymerization of functional monomers with Novozym 435

Authors

  • Martijn A. J. Veld,

    1. Laboratory of Macromolecular and Organic Chemistry, Technische Universiteit Eindhoven, P.O. Box 513, 5600 MB Eindhoven, The Netherlands
    Search for more papers by this author
  • Anja R. A. Palmans,

    Corresponding author
    1. Laboratory of Macromolecular and Organic Chemistry, Technische Universiteit Eindhoven, P.O. Box 513, 5600 MB Eindhoven, The Netherlands
    • Laboratory of Macromolecular and Organic Chemistry, Technische Universiteit Eindhoven, P.O. Box 513, 5600 MB Eindhoven, The Netherlands
    Search for more papers by this author
  • E. W. Meijer

    Corresponding author
    1. Laboratory of Macromolecular and Organic Chemistry, Technische Universiteit Eindhoven, P.O. Box 513, 5600 MB Eindhoven, The Netherlands
    • Laboratory of Macromolecular and Organic Chemistry, Technische Universiteit Eindhoven, P.O. Box 513, 5600 MB Eindhoven, The Netherlands
    Search for more papers by this author

Abstract

Two novel monomers, ambrettolide epoxide and isopropyl aleuriteate, encompassing functional groups, were obtained in a single step from commercially available materials. Novozym 435 catalyzed ring opening polymerization of ambrettolide epoxide furnished a polymer of Mn = 9.7 kg/mol and PDI = 1.9 while the epoxide groups remained unaffected during the polymerization. Selective polymerization of the primary hydroxyl groups of isopropyl aleuriteate using Novozym 435 was feasible and a polymer with moderate molecular weight (Mn = 5.6 kg/mol, PDI = 3.2) was isolated in moderate yield (43%). Subsequently, copolymerization of isopropyl aleuriteate with ε-CL in different ratios was performed, resulting in soluble, hydroxy functional polymers with good molecular weights (Mn = 10.4–27.2 kg/mol) in good yield (71–78%). The secondary hydroxy groups in the polymer reacted easily with hexyl isocyanate, showing the potential of isopropyl aleuriteate as a comonomer for the synthesis of functional polyesters. © 2007 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 5968–5978, 2007

Get access to the full text of this article

Ancillary