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Chain-End Functional di-Sorbitan Oleate Monomer Obtained from Renewable Resources as Precursors for Bio-Based Polyurethanes

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Abstract

A three-step synthetic route was proposed and tested to obtain a chain-end functional di-sorbitan oleate monomer: First, 1,18-octadec-9-enedioic acid compound was produced by self-metathesis reaction of an oleic acid; then, the 1,18-octadec-9-enoyl dichloride compound was yielded by chlorination of the di-acid with thionyl chloride, and finally, the 1,18-di-sorbitan oleate monomer was yielded by esterification of the dichloride with 1,4-sorbitan. The di-sorbitan oleate monomer was purified and then characterized by FTIR, 1H-NMR, DSC and TGA to establish its structure and properties. A bio-based polyurethane (PU) was synthesized by reacting the obtained 1,18-di-sorbitan oleate monomer and MDI. Rheological analysis showed that a curing reaction occurs as a significant increase of the storage modulus (G’) and the complex viscosity (η*) at 100 °C. The obtained bio-based PU was characterized by FTIR, TGA and DMA, confirming that 1,18-di-sorbitan oleate is a feasible monomer for synthesizing polyurethanes.

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Acknowledgements

The authors wish to thank the National Council of Science and Technology of Mexico (CONACYT) for supporting this research work through the project CB-2015–01-257591.

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Authors and Affiliations

  1. UAEMEX, Universidad Autónoma del Estado de México, Carretera Toluca - Atlacomulco Km. 14.5, San Cayetano de Morelos, Toluca de Lerdo Edo, 50200, México

    Susana Valencia-Bermudez & Susana Hernández-López

  2. CIATEQ, A.C, Centro de Tecnología Avanzada, Circuito de la Industria Pte Lte, 11 Mza 3 No 11, Parque Industrial Ex Hacienda Doña Rosa, de México, Lerma Edo, 52004, México

    Manuel Gutiérrez-Nava, José-Manuel Rojas-García & Luis-Edmundo Lugo-Uribe

Authors
  1. Susana Valencia-Bermudez
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  2. Susana Hernández-López
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  3. Manuel Gutiérrez-Nava
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  4. José-Manuel Rojas-García
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  5. Luis-Edmundo Lugo-Uribe
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Correspondence to Luis-Edmundo Lugo-Uribe.

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Valencia-Bermudez, S., Hernández-López, S., Gutiérrez-Nava, M. et al. Chain-End Functional di-Sorbitan Oleate Monomer Obtained from Renewable Resources as Precursors for Bio-Based Polyurethanes. J Polym Environ 28, 1406–1419 (2020). https://doi.org/10.1007/s10924-020-01692-0

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  • DOI: https://doi.org/10.1007/s10924-020-01692-0

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