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Photocrosslinkable Antibacterial Bioadhesives Derived from Soybean Oil-Based Hydroxyurethane Methacrylates

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Abstract

Compared to traditional invasive techniques for wound closure, photocrosslinkable surgical adhesives with antibacterial properties offer significant advantages. These include ease of application, a controllable and efficient curing reaction, reduced risk of pain and infection, and effective leakage prevention. This study introduces a novel soybean oil-based nonisocyanate polyurethane prepolymer for use in such adhesives. The prepolymer, a hydroxyurethane functionalized with methacrylate and quaternary ammonium groups (QAs), was characterized through spectroscopic methods. The resulting UV-curable bioadhesives, synthesized via thiol-ene-methacrylate click-photopolymerization, incorporated limonene as a reactive diluent, a tetra-functional thiol crosslinker, and a photoinitiator. Elemental analysis confirmed the uniform distribution of QAs and sulfur atoms, indicating a homogeneous network structure, corroborated by high gel content values in both organic (84–92%) and aqueous media (91–99%), and a consistent tan δ peak as per DMTA. The optimized adhesives exhibited strong adhesion (up to 377 kPa) to gelatin sheets—a tissue-analogous substrate—and displayed suitable surface free energy (45–52 mN/m) as determined by contact angle measurements, suggesting favorable thermodynamic adhesion to skin. Additionally, the adhesives showed satisfactory cytocompatibility with L-929 fibroblast cells and antimicrobial efficacy against two gram-positive and gram-negative bacterial strains, indicating promising biological activity.

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Authors and Affiliations

  1. Department of Chemical Engineering, Isfahan University of Technology, Isfahan, 8415683111, Iran

    Tina Rabiee & Saied Nouri Khorasani

  2. Iran Polymer and Petrochemical Institute, Tehran, P.O. Box: 14965/115, Iran

    Hamid Yeganeh

  3. Catalysis Division, Department of Chemistry, University of Isfahan, Isfahan, 8174673441, Iran

    Iraj Mohammadpoor-Baltork

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  1. Tina Rabiee
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Contributions

T.R contributed to the acquisition, analysis, and interpretation of data; drafted the work; approved the version to be published; and agreed to be accountable for all aspects of the work in ensuring that questions related to the accuracy or integrity of any partof the work are appropriately investigated and resolved. H.Y. and S.N.K. contributed to the conception and design of the work; and interpretation of data; drafted the work, revised it critically for important intellectual content; approved the version to be submitted; and agreed to be accountable for all aspects of the work to ensure that questions related to the accuracy or integrity of any part of the work are appropriately investigated and resolved. I.M.B. contributed to the interpretation of data; approved the version to be published; and agreed to be accountable for all aspects of the work in ensuring that questions related to the accuracy or integrity of any part of the work are appropriately investigated and resolved.

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Correspondence to Hamid Yeganeh or Saied Nouri Khorasani.

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Rabiee, T., Yeganeh, H., Khorasani, S.N. et al. Photocrosslinkable Antibacterial Bioadhesives Derived from Soybean Oil-Based Hydroxyurethane Methacrylates. J Polym Environ (2024). https://doi.org/10.1007/s10924-024-03333-2

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