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Continuous Flow Synthesis of Functional Isocyanate-Free Poly(oxazolidone)s by Step-Growth Polymerization

  • Fabiana Siragusa
    Fabiana Siragusa
    Center for Education and Research on Macromolecules (CERM), CESAM Research Unit, University of Liège, Sart-Tilman B6a, 4000 Liège, Belgium
  • Lionel Crane
    Lionel Crane
    Center for Education and Research on Macromolecules (CERM), CESAM Research Unit, University of Liège, Sart-Tilman B6a, 4000 Liège, Belgium
    Center for Integrated Technology and Organic Synthesis (CiTOS), MolSys Research Unit, University of Liège, Sart-Tilman B6a, 4000 Liège, Belgium
    More by Lionel Crane
  • Pierre Stiernet
    Pierre Stiernet
    Center for Education and Research on Macromolecules (CERM), CESAM Research Unit, University of Liège, Sart-Tilman B6a, 4000 Liège, Belgium
  • Thomas Habets
    Thomas Habets
    Center for Education and Research on Macromolecules (CERM), CESAM Research Unit, University of Liège, Sart-Tilman B6a, 4000 Liège, Belgium
  • Bruno Grignard
    Bruno Grignard
    Center for Education and Research on Macromolecules (CERM), CESAM Research Unit, University of Liège, Sart-Tilman B6a, 4000 Liège, Belgium
    FRITCO2T Platform, CESAM Research Unit, University of Liège, Sart-Tilman B6a, 4000 Liège, Belgium
  • Jean-Christophe M. Monbaliu*
    Jean-Christophe M. Monbaliu
    Center for Integrated Technology and Organic Synthesis (CiTOS), MolSys Research Unit, University of Liège, Sart-Tilman B6a, 4000 Liège, Belgium
    WEL Research Institute, 1300 Wavre, Belgium
    *E-mail: [email protected]
  • , and 
  • Christophe Detrembleur*
    Christophe Detrembleur
    Center for Education and Research on Macromolecules (CERM), CESAM Research Unit, University of Liège, Sart-Tilman B6a, 4000 Liège, Belgium
    WEL Research Institute, 1300 Wavre, Belgium
    *E-mail: [email protected]
Cite this: ACS Macro Lett. 2024, 13, 5, 644–650
Publication Date (Web):May 8, 2024
https://doi.org/10.1021/acsmacrolett.4c00203
Copyright © 2024 American Chemical Society

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    Abstract

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    Flow chemistry presents many advantages over batch processes for the fast and continuous production of polymers under more robust, safer, and easily scalable conditions. Although largely exploited for chain-growth polymerizations, it has rarely been applied to step-growth polymerizations (SGP) due to their inherent limitations. Here, we report the facile and fast preparation of an emerging class of nonisocyanate polyurethanes, i.e., CO2-based poly(oxazolidone)s, by SGP in continuous flow reactors. Importantly, we also demonstrate that functional poly(oxazolidone)s are easily prepared by telescoping a flow module where SGP occurs with reagents able to simultaneously promote two polymer derivatizations in a second module, i.e., dehydration followed by cationic thiol–ene to yield poly(N,S-acetal oxazolidone)s. The functional polymer is produced at a high rate and functionalization degree, without requiring the isolation of any intermediates. This work demonstrates the enormous potential of flow technology for the facile and fast continuous production of functional polymers by SGP.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acsmacrolett.4c00203.

    • Material and methods, SEC chromatograms, 1H and 13C NMR spectra, TGA–DTG curves, and modulated DSC plots for all polymers (PDF)

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