Preparation of methacrylate End-functionalized Poly(2-ethyl-2-oxazoline) macromonomers

C. Weber, C.R. Becer, A. Baumgaertel, R. Hoogenboom, U.S. Schubert (Corresponding author)

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    Abstract

    Three methods for the functionalization of 2-ethyl-2-oxazoline (EtOx) oligomers with a methacrylate or methacrylamide unit are compared to identify the best suitable route to obtain such macromolecules. In the first method, a functional initiator, namely methacryloyl chloride, was used for the cationic ring-opening polymerization of EtOx, which proceeded in a living manner. However, the formation of a large amount of hydrogen initiated chains resulted in a low degree of functionalization (21%). The second method was based on the termination of active oligo(EtOx) chains with an aqueous sodium carbonate solution yielding hydroxyl-terminated oligomers. These end-groups were subsequently modified by an esterification reaction with methacryloyl chloride yielding oligomers with a large variety of different end-groups, as demonstrated by MALDI-TOF-MS. In the last method, the living chain ends were reacted with in situ formed triethyl ammonium methacrylate yielding macromonomers with a high degree of functionalization (>80%). Besides, MALDI-TOF-MS analysis revealed only a single oligomer distribution with the desired end-groups. Furthermore, these directly end-capped oligomers revealed narrow molar mass distributions with PDI values below 1.2 making this the best method for macromomonomer synthesis.
    Original languageEnglish
    Pages (from-to)149-165
    Number of pages17
    JournalDesigned Monomers and Polymers
    Volume12
    Issue number2
    DOIs
    Publication statusPublished - 2009

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