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Novel one-pot synthesis of polymeric hydrogels based on isocyanate click chemistry: Structural and functional characterization

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Abstract

In this work, a novel one-pot synthesis of polymeric hydrogels (HGs) based on isocyanate click chemistry is proposed and evaluated. In particular, the proposed synthetic route allows to easily and effectively obtain HGs with different types of carbonyl groups, such as urea, urethane, thiourethane, and amide groups, as an approach to impact and modulate the structural, thermal, and functional behavior of the crosslinked networks. To carry out the above, the proposed methodology was employed to prepare HGs from hexamethylene diisocyanate, sorbitol, L-cysteine ​​and water, under moderate conditions (60° C for 24 h). Using FTIR-ATR, FEDS, and solid-state 13C CP/MAS NMR, it was possible to determine the presence and the relative amounts of different carbonyl groups in the obtained HGs, which can be modulated by varying the amounts of diisocyanate, L-cysteine, ​​and sorbitol employed in their synthesis. In addition, TGA and DSC analysis corroborated the influence of these carbonyl groups in the thermal properties of the HGs, i.e., thermal stability and glass transition. It was observed that an increase in L-cysteine and sorbitol amount in the HGs improved their thermal stability (> 200 °C) and increased their Tg values (55–68 °C) due to factors associated with crosslinking degree and intermolecular interactions. On the other hand, in terms of their functional behavior, HGs presented a good water absorption capacity at different pH values ​​(1.0, 7.0 and 12.0), being higher than 300% and enhanced by the presence of L-cysteine and sorbitol in the polymeric structures. Likewise, the HGs were able to retain and release an alkaline medium, in a controlled way, into a neutral and acidic environment, which points to the possibility of implementing this type of HGs in the design and development of novel drug delivery systems. Finally, an inhibitory effect (up to 40%) on the growth of gram-positive bacteria, such as S. aureus, by the HGs reflected their ability to effectively interact with these microorganisms by means of their polymeric structures and functional groups. In this sense, this work represents an important step in the designing and preparation of polymeric HGs based on isocyanate click chemistry, with modulated structural, thermal, and functional properties, that could be applied in different fields, including those of biomedical nature.

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Acknowledgements

The authors acknowledge to Universidad del Valle and Mindtech s.a.s for the financial support to carry out this research work.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Natural and Exact Sciences, Research Group in Sciences with Technological Applications (GI-CAT), Universidad del Valle, Street 13 # 100-00, Campus Melendez, Building E20, 760032, Cali, Colombia

    Andrés Otálora, Tulio A. Lerma & Manuel Palencia

  2. Mindtech Research Group (Mindtech-RG), Mindtech S.A.S, 760026, Cali, Colombia

    Andrés Otálora & Tulio A. Lerma

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  2. Tulio A. Lerma
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  3. Manuel Palencia
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Contributions

All authors contributed with the experimental design, analysis, and manuscript writing. In addition, M. Palencia introduced the main idea and supervised the work, A. Otálora contributed with the preparation and characterization of the materials, and T. A. Lerma contributed with the experimental analysis.

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Correspondence to Manuel Palencia.

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Otálora, A., Lerma, T.A. & Palencia, M. Novel one-pot synthesis of polymeric hydrogels based on isocyanate click chemistry: Structural and functional characterization. J Polym Res 29, 491 (2022). https://doi.org/10.1007/s10965-022-03331-9

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