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Synthesis of tetraallylated cystamine and the study of its performance as a curing agent for the epoxy/thiol-ene photopolymerization of biobased nopol epoxy resins

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Abstract

This article reports the synthesis of a bio-inspired curing agent, the tetraallyl cystamine (TAC) and the evaluation of its performance to photocure two epoxy resins derived from the terpenoid nopol, by using the epoxy/thiol-ene photopolymerization technique. The curing agent was prepared in two stages: a) reaction of the diallylamine with ethylene disulfide, through a mercaptoethylation reaction and b) oxidation of the obtained thiol to disulfide, using dimethylsulfoxide as an oxidizing agent. To the epoxy resins was added the curing agent TAC, pentaerythritol tetrakis (3-mercaptopropionate) and dimethoxyphenylacetophenone, to obtain cross-linked co-networks of the polyether-polythioether type. A trifunctional nopol epoxycycloaliphatic epoxy resin and an epoxycycloaliphatic-glycidyl nopol epoxy resin were evaluated, with the former displaying higher reactivity, higher modulus and higher thermal stability.

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Acknowledgements

The support of the Mexican National Council of Science and Technology (CONACYT) through grant 282882 (Fundamental Science) is greatly appreciated. We gratefully acknowledge María Guadalupe Méndez, Myrna Salinas, José Guadalupe Tellez, Jorge Felix Espinoza, and Judith Cabello for their assistance regarding the study analysis

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  1. Centro de Investigación en Química Aplicada, Blvd Enrique Reyna # 140, 25294, Saltillo, Coahuila, Mexico

    Ricardo Acosta Ortiz, Alan Isaac Hernández Jiménez & Aida Esmeralda García Valdez

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  1. Ricardo Acosta Ortiz
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  2. Alan Isaac Hernández Jiménez
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  3. Aida Esmeralda García Valdez
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Correspondence to Ricardo Acosta Ortiz.

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Acosta Ortiz, R., Hernández Jiménez, A.I. & García Valdez, A.E. Synthesis of tetraallylated cystamine and the study of its performance as a curing agent for the epoxy/thiol-ene photopolymerization of biobased nopol epoxy resins. J Polym Res 28, 366 (2021). https://doi.org/10.1007/s10965-021-02725-5

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