Investigation of curing rates of bio-based thiol-ene films from diallyl 2,5-furandicaboxylate

Daniel Bo Larsen, Rene Sønderbæk-Jørgensen, Jens Ø. Duus, Anders E. Daugaard*

*Corresponding author for this work

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

The bio-based monomer, 2,5-furandicarboxylic acid, has been adapted to classic thiol-ene chemistry by derivatization of the acid with allyl alcohol. This new monomer has allowed for the synthesis of new thermoset systems, capable of forming green, sustainable materials through UV-crosslinking. In this study, the synthesis of the new monomer along with thorough kinetic studies of the new thermoset systems are presented. In order to determine kinetic values for the systems, all reactions have been followed by real-time FT-IR. Initially, a study of three different photoinitiators is performed on a classic TEMPIC-TATATO system, in order to determine the superior initiator for the new systems. The new monomer is crosslinked with five different thiol compounds in both stoichiometric and off-stoichiometric ratios, yielding an array of bio-based thermosets. The properties of these systems are determined through DSC, TGA and tensile testing, allowing determination of the systems with superior properties. In general, most systems proved to cure fully, with the exception of issues encountered from thiols with long ethoxylated chains.
Original languageEnglish
JournalEuropean Polymer Journal
Volume102
Pages (from-to)1-8
ISSN0014-3057
DOIs
Publication statusPublished - 2018

Cite this

@article{2c3ce54ccf9c4e10893dc4527fceb066,
title = "Investigation of curing rates of bio-based thiol-ene films from diallyl 2,5-furandicaboxylate",
abstract = "The bio-based monomer, 2,5-furandicarboxylic acid, has been adapted to classic thiol-ene chemistry by derivatization of the acid with allyl alcohol. This new monomer has allowed for the synthesis of new thermoset systems, capable of forming green, sustainable materials through UV-crosslinking. In this study, the synthesis of the new monomer along with thorough kinetic studies of the new thermoset systems are presented. In order to determine kinetic values for the systems, all reactions have been followed by real-time FT-IR. Initially, a study of three different photoinitiators is performed on a classic TEMPIC-TATATO system, in order to determine the superior initiator for the new systems. The new monomer is crosslinked with five different thiol compounds in both stoichiometric and off-stoichiometric ratios, yielding an array of bio-based thermosets. The properties of these systems are determined through DSC, TGA and tensile testing, allowing determination of the systems with superior properties. In general, most systems proved to cure fully, with the exception of issues encountered from thiols with long ethoxylated chains.",
author = "Larsen, {Daniel Bo} and Rene S{\o}nderb{\ae}k-J{\o}rgensen and Duus, {Jens {\O}.} and Daugaard, {Anders E.}",
year = "2018",
doi = "10.1016/j.eurpolymj.2018.03.005",
language = "English",
volume = "102",
pages = "1--8",
journal = "European Polymer Journal",
issn = "0014-3057",
publisher = "Pergamon Press",

}

Investigation of curing rates of bio-based thiol-ene films from diallyl 2,5-furandicaboxylate. / Larsen, Daniel Bo; Sønderbæk-Jørgensen, Rene; Duus, Jens Ø.; Daugaard, Anders E.

In: European Polymer Journal, Vol. 102, 2018, p. 1-8.

Research output: Contribution to journalJournal articleResearchpeer-review

TY - JOUR

T1 - Investigation of curing rates of bio-based thiol-ene films from diallyl 2,5-furandicaboxylate

AU - Larsen, Daniel Bo

AU - Sønderbæk-Jørgensen, Rene

AU - Duus, Jens Ø.

AU - Daugaard, Anders E.

PY - 2018

Y1 - 2018

N2 - The bio-based monomer, 2,5-furandicarboxylic acid, has been adapted to classic thiol-ene chemistry by derivatization of the acid with allyl alcohol. This new monomer has allowed for the synthesis of new thermoset systems, capable of forming green, sustainable materials through UV-crosslinking. In this study, the synthesis of the new monomer along with thorough kinetic studies of the new thermoset systems are presented. In order to determine kinetic values for the systems, all reactions have been followed by real-time FT-IR. Initially, a study of three different photoinitiators is performed on a classic TEMPIC-TATATO system, in order to determine the superior initiator for the new systems. The new monomer is crosslinked with five different thiol compounds in both stoichiometric and off-stoichiometric ratios, yielding an array of bio-based thermosets. The properties of these systems are determined through DSC, TGA and tensile testing, allowing determination of the systems with superior properties. In general, most systems proved to cure fully, with the exception of issues encountered from thiols with long ethoxylated chains.

AB - The bio-based monomer, 2,5-furandicarboxylic acid, has been adapted to classic thiol-ene chemistry by derivatization of the acid with allyl alcohol. This new monomer has allowed for the synthesis of new thermoset systems, capable of forming green, sustainable materials through UV-crosslinking. In this study, the synthesis of the new monomer along with thorough kinetic studies of the new thermoset systems are presented. In order to determine kinetic values for the systems, all reactions have been followed by real-time FT-IR. Initially, a study of three different photoinitiators is performed on a classic TEMPIC-TATATO system, in order to determine the superior initiator for the new systems. The new monomer is crosslinked with five different thiol compounds in both stoichiometric and off-stoichiometric ratios, yielding an array of bio-based thermosets. The properties of these systems are determined through DSC, TGA and tensile testing, allowing determination of the systems with superior properties. In general, most systems proved to cure fully, with the exception of issues encountered from thiols with long ethoxylated chains.

U2 - 10.1016/j.eurpolymj.2018.03.005

DO - 10.1016/j.eurpolymj.2018.03.005

M3 - Journal article

VL - 102

SP - 1

EP - 8

JO - European Polymer Journal

JF - European Polymer Journal

SN - 0014-3057

ER -