Novel Bio-Based Epoxy Thermosets Based on Triglycidyl Phloroglucinol Prepared by Thiol-Epoxy Reaction
The pure trifunctional glycidyl monomer from phloroglucinol (3EPO-Ph) was synthesized and used as feedstock in the preparation of novel bio-based thermosets by thiol-epoxy curing. The monomer was crosslinked with different commercially available thiols: tetrafunctional thiol (PETMP), trifunctional t...
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doaj-12fbf460fc934d2fb641ccab26a745182020-11-25T01:27:38ZengMDPI AGPolymers2073-43602020-02-0112233710.3390/polym12020337polym12020337Novel Bio-Based Epoxy Thermosets Based on Triglycidyl Phloroglucinol Prepared by Thiol-Epoxy ReactionDailyn Guzmán0David Santiago1Àngels Serra2Francesc Ferrando3Eurecat–Chemical Technology Unit, c/Marcel·lí Domingo 2, Edif. N5, 43007 Tarragona, SpainEurecat–Chemical Technology Unit, c/Marcel·lí Domingo 2, Edif. N5, 43007 Tarragona, SpainDepartment of Analytical and Organic Chemistry, Universitat Rovira i Virgili, c/Marcel·lí Domingo 1, Edif. N4, 43007 Tarragona, SpainDepartment of Mechanical Engineering, Universitat Rovira i Virgili, Av. Països Catalans 26, 43007 Tarragona, SpainThe pure trifunctional glycidyl monomer from phloroglucinol (3EPO-Ph) was synthesized and used as feedstock in the preparation of novel bio-based thermosets by thiol-epoxy curing. The monomer was crosslinked with different commercially available thiols: tetrafunctional thiol (PETMP), trifunctional thiol (TTMP) and an aromatic dithiol (TBBT) as curing agents in the presence of a base. As catalyst, two different commercial catalysts: LC-80 and 4-(<i>N</i>,<i>N</i>-dimethylamino) pyridine (DMAP) and a synthetic catalyst, imidazolium tetraphenylborate (base generator, BG) were employed. The curing of the reactive mixtures was studied by using DSC and the obtained materials by means of differential scanning calorimetry (DSC), thermogravimetric analysis (TGA) and dynamic mechanical thermal analysis (DMTA). The results revealed that only the formulations catalyzed by BG showed a latent character. Already prepared thermosetting materials showed excellent thermal, thermomechanical and mechanical properties, with a high transparency. In addition to that, when compared with the diglycidyl ether of bisphenol A (DGEBA)/PETMP material, the thermosets prepared from the triglycidyl derivative of phloroglucinol have better final characteristics and therefore this derivative can be considered as a partial or total renewable substitute of DGEBA in technological applications.https://www.mdpi.com/2073-4360/12/2/337epoxy thermosetphloroglucinolthiol-epoxylatent catalystsustainability |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Dailyn Guzmán David Santiago Àngels Serra Francesc Ferrando |
spellingShingle |
Dailyn Guzmán David Santiago Àngels Serra Francesc Ferrando Novel Bio-Based Epoxy Thermosets Based on Triglycidyl Phloroglucinol Prepared by Thiol-Epoxy Reaction Polymers epoxy thermoset phloroglucinol thiol-epoxy latent catalyst sustainability |
author_facet |
Dailyn Guzmán David Santiago Àngels Serra Francesc Ferrando |
author_sort |
Dailyn Guzmán |
title |
Novel Bio-Based Epoxy Thermosets Based on Triglycidyl Phloroglucinol Prepared by Thiol-Epoxy Reaction |
title_short |
Novel Bio-Based Epoxy Thermosets Based on Triglycidyl Phloroglucinol Prepared by Thiol-Epoxy Reaction |
title_full |
Novel Bio-Based Epoxy Thermosets Based on Triglycidyl Phloroglucinol Prepared by Thiol-Epoxy Reaction |
title_fullStr |
Novel Bio-Based Epoxy Thermosets Based on Triglycidyl Phloroglucinol Prepared by Thiol-Epoxy Reaction |
title_full_unstemmed |
Novel Bio-Based Epoxy Thermosets Based on Triglycidyl Phloroglucinol Prepared by Thiol-Epoxy Reaction |
title_sort |
novel bio-based epoxy thermosets based on triglycidyl phloroglucinol prepared by thiol-epoxy reaction |
publisher |
MDPI AG |
series |
Polymers |
issn |
2073-4360 |
publishDate |
2020-02-01 |
description |
The pure trifunctional glycidyl monomer from phloroglucinol (3EPO-Ph) was synthesized and used as feedstock in the preparation of novel bio-based thermosets by thiol-epoxy curing. The monomer was crosslinked with different commercially available thiols: tetrafunctional thiol (PETMP), trifunctional thiol (TTMP) and an aromatic dithiol (TBBT) as curing agents in the presence of a base. As catalyst, two different commercial catalysts: LC-80 and 4-(<i>N</i>,<i>N</i>-dimethylamino) pyridine (DMAP) and a synthetic catalyst, imidazolium tetraphenylborate (base generator, BG) were employed. The curing of the reactive mixtures was studied by using DSC and the obtained materials by means of differential scanning calorimetry (DSC), thermogravimetric analysis (TGA) and dynamic mechanical thermal analysis (DMTA). The results revealed that only the formulations catalyzed by BG showed a latent character. Already prepared thermosetting materials showed excellent thermal, thermomechanical and mechanical properties, with a high transparency. In addition to that, when compared with the diglycidyl ether of bisphenol A (DGEBA)/PETMP material, the thermosets prepared from the triglycidyl derivative of phloroglucinol have better final characteristics and therefore this derivative can be considered as a partial or total renewable substitute of DGEBA in technological applications. |
topic |
epoxy thermoset phloroglucinol thiol-epoxy latent catalyst sustainability |
url |
https://www.mdpi.com/2073-4360/12/2/337 |
work_keys_str_mv |
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1725104103467515904 |