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Non-isocyanate epoxy vinyl ester urethane prepolymer based on diglycidyl ether of bisphenol-A

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Abstract

Vinyl ester resins (VERs) are one of the main categories of polymeric matrices for fabrication of high-performance commercial composites. They have more desirable properties compared with unsaturated polyester resins. Inserting urethane functional groups in the structure of VERs and producing urethane vinyl ester resin (UVER) improve its impact and chemical resistance, enlongation and toughness. The use of isocyanate as the primary resource in urethane preparation, which is derived from phosgene toxic material, may be associated with environmental hazards; as a result, non-isocyanate polyurethane (NIPU) methods have been developed. Herein, we have described the preparation and characterization of UVER by isocyanate-free system. First, cyclic carbonates of epoxides, 2-hydroxy-3-(4-(oxiran-2-ylmethoxy)butoxy)propyl methacrylate (HOMBPM) and diglycidyl ether of bisphenol-A epoxy resin (DGEBA) were synthesized by treatment of the corresponding epoxides with atmospheric pressure of carbon dioxide and tetrabutylammonium bromide (TBAB) as a catalyst. Then, the as-prepared cyclic carbonates were reacted with ethylenediamine in the presence of different catalysts to produce non-isocyanate epoxy vinyl ester urethane prepolymer. UVER is a potential compound for curing with VERs and fabricating materials with superior mechanical features such as elongation and tensile strength in comparison to VERs. Characterization techniques such as FTIR, 1H and 13C NMR spectroscopy and titration methods for measurements of epoxy equivalent weight (EEW), acid number and amine value are used in the synthesis of the desired compounds.

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Acknowledgements

The authors greatly acknowledge the partial support of this study by the Research Council of Shiraz University. Farassan Manufacturing and Industrial Company is gracefully appreciated.

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Authors and Affiliations

  1. Department of Chemistry, College of Science, Shiraz University, Shiraz, 7194684795, Iran

    Soheila Ghasemi, Milad Ghezelsofloo, Mahsa Naeimi, Bahman Tamami & Hamed Allahyari

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  1. Soheila Ghasemi
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  2. Milad Ghezelsofloo
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  3. Mahsa Naeimi
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  5. Hamed Allahyari
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Correspondence to Soheila Ghasemi.

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Ghasemi, S., Ghezelsofloo, M., Naeimi, M. et al. Non-isocyanate epoxy vinyl ester urethane prepolymer based on diglycidyl ether of bisphenol-A. Iran Polym J (2024). https://doi.org/10.1007/s13726-024-01289-7

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