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Polymers 2018, 10(4), 439; https://doi.org/10.3390/polym10040439

Effect of Selected Thiols on Cross-Linking of Acrylated Epoxidized Soybean Oil and Properties of Resulting Polymers

1
Department of Polymer Chemistry and Technology, Kaunas University of Technology, Radvilenu rd. 19, 50254 Kaunas, Lithuania
2
Department of Mechanical Engineering, Universitat Rovira i Virgili, C/Països Catalans 26, 43007 Tarragona, Spain
3
Department of Analytical and Organic Chemistry, Universitat Rovira i Virgili, C/Marcel·lí Domingo s/n, Edifici N4, 43007 Tarragona, Spain
*
Author to whom correspondence should be addressed.
Received: 28 March 2018 / Revised: 10 April 2018 / Accepted: 12 April 2018 / Published: 14 April 2018
(This article belongs to the Special Issue Bio-Based Resins and Crosslinked Polymers from Renewable Resources)
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Abstract

The effect of the chemical structure and functionality of three structurally different thiols on the cross-linking of acrylated epoxidized soybean oil and on the properties of the resulting polymers was investigated in this study. 1,3-Benzenedithiol, pentaerythritol tetra(3-mercaptopropionate), and an hexathiol synthesized from squalene were used in the cross-linking of acrylated epoxidized soybean oil by thiol–Michael addition reaction. The reactivity of thiols determined from calorimetric curves followed the order: 1,3-benzenedithiol > pentaerythritol tetra(3-mercaptopropionate) > hexathiolated squalene. Thermal and mechanical properties and the swelling in different solvents of the cross-linked polymers were studied. The cross-linked polymer obtained from 1,3-benzenedithiol showed the highest swelling values in chloroform and toluene. The cross-linked polymer with pentaerythritol tetra(3-mercaptopropionate) fragments showed the best mechanical performance (highest mechanical strength and Young’s modulus) and thermal stability. The cross-linked polymers from hexathiolated squalene showed the highest glass transition temperature. View Full-Text
Keywords: cross-linking; thiol–Michael; soybean oil; bio-based polymer cross-linking; thiol–Michael; soybean oil; bio-based polymer
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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Kasetaite, S.; De la Flor, S.; Serra, A.; Ostrauskaite, J. Effect of Selected Thiols on Cross-Linking of Acrylated Epoxidized Soybean Oil and Properties of Resulting Polymers. Polymers 2018, 10, 439.

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