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The role played by different active hydrogen sources in the microencapsulation of a commercial oligomeric diisocyanate

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Abstract

The present paper regards the development of polyurea/polyurethane (PUa/PU) and PUa/PU–silica hybrid shell microcapsules (MCs), loaded with Ongronat®2500, a commercial type of oligomeric methylene diphenyl diisocyanate with increased functionality, as core material. Ongronat® 2500 has a wide range of applications either for the production of rigid polyurethane foams and as cross-linking or self-healing agent. The MCs were achieved by a facile, one-pot process, consisting of an oil-in-water microemulsion system combined with interfacial polymerization processing, employing a higher reactivity isocyanate, toluene diisocyanate, to competitively contribute to the shell formation. Ethylenediamine, polyethylenimine (PEI), triethoxy(octyl)silane (n-OTES) and 3-(2-aminoethylamino) propyltrimethoxysilane (aminosilane) were tested as active, or “latent” active hydrogen (H) sources, and their effect on the MCs morphology, encapsulation yield, shelf life, shell’s chemical structure and thermal stability was assessed. The MCs are aimed at the development of a new generation of adhesive formulations, which are mono-component, self-reactive, eco-friendly and with low health hazards, for industries such as the footwear, construction, aerospace and automotive. MCs’ characterization was performed using Fourier transformed infrared spectroscopy, thermogravimetric analysis and scanning electron microscopy. It was possible to obtain MCs with a high loading of Ongronat®2500, exhibiting a core–shell morphology, an increased shell resistance to temperature and improved shelf life. The combination of PEI and n-OTES led to the best compromise between encapsulation yield and shelf life. Finally, a confinement effect of the encapsulated macromolecules is herein shown for the first time, by the drastic narrowing of the NCO peak at the FTIR spectrum of the MCs.

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Acknowledgements

This research was funded by FEDER through the COMPETE 2020 program and the Regional Operational Program of Lisbon—LISBOA2020, in the scope of the Portugal2020 Project 17930, “ECOBOND—Development of new ecological, self-reactive, monocomponent adhesives”. The authors gratefully acknowledge Fundação para a Ciência e a Tecnologia (FCT) through the support of CERENA (Strategic Project FCT-UID/ECI/04028/2019) and the Grants SFRH/BD/140700/2018 (Mónica V. Loureiro) and SFRH/BD/138717/2018 (Mário Vale).

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Authors and Affiliations

  1. CERENA, Departamento de Engenharia Química, Instituto Superior Técnico, Universidade de Lisboa, Avenida Rovisco Pais, 1049-001, Lisbon, Portugal

    Mónica V. Loureiro, Sofia Rocha, Mário Vale, João C. Bordado & Ana C. Marques

  2. CQE, Departamento de Engenharia Química, Instituto Superior Técnico, Universidade de Lisboa, Avenida Rovisco Pais, 1049-001, Lisbon, Portugal

    Mahboobeh Attaei

  3. Instituto Politécnico do Cávado e do Ave – IPCA, Campus do IPCA, Barcelos, Portugal

    Ricardo Simões

  4. CIPADE-Indústria e Investigação de Produtos Adesivos, SA. Av. Primeiro de Maio 121, São João da Madeira, Portugal

    Isabel Pinho

Authors
  1. Mónica V. Loureiro
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  3. Sofia Rocha
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Correspondence to Ana C. Marques.

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Electronic supplementary material

The supplementary file S1 shows the MCs size distribution bar chart, for each MCs’ sample. The value of the predominant MCs’ diameter value is provided in the main body of the manuscript. The distribution chart enables a clearer vision of the MCs’ size distribution. The supplementary file S2 shows the bar charts representing the NCO FTIR’ peaks narrowing and shifting effect for the encapsulated isocyanate species. These effects, as well as a hypothesis for these observations are explained in the main body of the manuscript. The FTIR peaks, used to draw the bar charts are also provided in the paper. The supplementary file 2 enables a clearer vision of the referred effect.

Supplementary material 1 (DOCX 662 kb)

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Loureiro, M.V., Attaei, M., Rocha, S. et al. The role played by different active hydrogen sources in the microencapsulation of a commercial oligomeric diisocyanate. J Mater Sci 55, 4607–4623 (2020). https://doi.org/10.1007/s10853-019-04301-1

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