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Debondable Epoxy-Acrylate Adhesives using β-Amino Ester Chemistry

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Download Hi-Res ImageDownload to MS-PowerPointCite This:ACS Appl. Mater. Interfaces 2024, 16, 46, 64050-64057
    Applications of Polymer, Composite, and Coating Materials

    Debondable Epoxy-Acrylate Adhesives using β-Amino Ester Chemistry
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    • Tim Maiheu
      Tim Maiheu
      Polymer Chemistry Research group, Centre of Macromolecular Chemistry (CMaC), Department of Organic and Macromolecular Chemistry, Faculty of Sciences, Ghent University, Krijgslaan 281-S4, Ghent 9000, Belgium
      More by Tim Maiheu
      Orcidhttps://orcid.org/0000-0003-3096-5412
    • Erica Laguzzi
      Erica Laguzzi
      Polymer Chemistry Research group, Centre of Macromolecular Chemistry (CMaC), Department of Organic and Macromolecular Chemistry, Faculty of Sciences, Ghent University, Krijgslaan 281-S4, Ghent 9000, Belgium
      Dipartimento di Scienze e Innovazione Tecnologica (DISIT), Università del Piemonte Orientale “A. Avogadro”, Viale T. Michel 11, 15121 Alessandria (AL), Italy
      More by Erica Laguzzi
      Orcidhttps://orcid.org/0009-0001-5637-9174
    • Andrew T. Slark
      Andrew T. Slark
      Department of Chemistry, University of Sheffield, Brook Hill, Sheffield S3 7HF, United Kingdom
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      Orcidhttps://orcid.org/0000-0001-7809-0139
    • Filip E. Du Prez*
      Filip E. Du Prez
      Polymer Chemistry Research group, Centre of Macromolecular Chemistry (CMaC), Department of Organic and Macromolecular Chemistry, Faculty of Sciences, Ghent University, Krijgslaan 281-S4, Ghent 9000, Belgium
      *Email: [email protected]
      More by Filip E. Du Prez
      Orcidhttps://orcid.org/0000-0001-7727-4155
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    ACS Applied Materials & Interfaces

    Cite this: ACS Appl. Mater. Interfaces 2024, 16, 46, 64050–64057
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    https://doi.org/10.1021/acsami.4c15346
    Published November 8, 2024
    Copyright © 2024 American Chemical Society
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    Abstract

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    The reuse of multilayered materials, which are held together by structural epoxy adhesives, is a major challenge since the bonded substrates cannot be easily separated for recycling. In this research, we explore a one-pot strategy based on β-amino ester chemistry for the development of modified epoxy adhesives with on-demand debonding potential. For this, a formulation of commercially available acrylate, epoxy and amine compounds is used. The research starts with a systematic study, demonstrating the influence of the different compounds on the thermal and adhesive properties of the materials. Subsequently, the potential for debonding is demonstrated using rheological measurements and tensile tests. The fast, catalyst-free Aza-Michael reaction enables the straightforward preparation of such epoxy-based adhesives, while the reverse reaction allows for debonding at 120 °C. In general, a chemical design is demonstrated for producing an industrially attractive generation of debondable epoxy-based adhesives.

    Copyright © 2024 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acsami.4c15346.

    • Characterization of the networks; additional IR spectra, DSC, and TGA thermograms; rheological data including amplitude sweeps, stress relaxation data and creep measurements; adhesive analysis including lap shear data and pictures of the debonded surfaces (PDF)

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    This article is cited by 3 publications.

    1. Ganapathy Ranjani, Sathiyaraj Subramaniyan, Ximena Lopez-Lorenzo, Minna Hakkarainen, Per-Olof Syrén. Chemically Recyclable and Enzymatically Degradable Thermostable Polyesters with Inherent Strain from α-Pinene-Derived Chiral Diols. ACS Sustainable Chemistry & Engineering 2025, Article ASAP.
    2. Peixin Niu, Zhiying Zhao, Yifang Zhao, Jun Zhu, Liuhe Wei, Yuhan Li. Hyperbranched Thiol-Capped Polyurethane: A Toughening Curing Agent for High-Performance Epoxy Adhesives. Langmuir 2025, 41 (12) , 8279-8289. https://doi.org/10.1021/acs.langmuir.5c00102
    3. Francesca Portone, Loc Tan Nguyen, Roberta Pinalli, Alessandro Pedrini, Filip E. Du Prez, Enrico Dalcanale. Debondable phenoxy-based structural adhesives with β-amino amide containing reversible crosslinkers. RSC Applied Polymers 2025, 13 https://doi.org/10.1039/D4LP00369A
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    ACS Applied Materials & Interfaces

    Cite this: ACS Appl. Mater. Interfaces 2024, 16, 46, 64050–64057
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acsami.4c15346
    Published November 8, 2024
    Copyright © 2024 American Chemical Society
    Request reuse permissions

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