Biobased Cationically Polymerizable Epoxy Thermosets from Furan and Fatty Acid Derivatives

Samer Nameer, Daniel B. Larsen, Jens Ø. Duus, Anders E. Daugaard, Mats Johansson*

*Corresponding author for this work

Research output: Contribution to journalJournal articleResearchpeer-review

131 Downloads (Pure)

Abstract

In the pursuit of environmentally friendly building blocks in polymer chemistry the utilization of biobased monomers is highly desired. In the present study, the biobased monomer 2,5-furandicarboxylic acid (FDCA) has been extended into epoxy thermosets. The study presents the synthesis of diallyl furan-2,5-dicarboxylate (DAFDC) followed by an epoxidation of the allyls to form diglycidyl furan-2,5-dicarboxylate (DGFDC). DGFDC was then copolymerized in both stoichiometric and off-stoichiometric ratios with epoxidized fatty methyl esters to form a range of thermosets. The cross-linking reaction was either thermally or UV-induced cationic polymerization utilizing onium salt initiators where the reactivity was studied by DSC and real-time fourier transform infrared analysis. Furthermore, the structure–property relationships of the final thermosets were determined by dynamic mechanical thermal analysis revealing a possibility to tune the properties over a wide range. In addition thermosets were made from diglycidyl Bisphenol-A (DGEBA) with epoxidized fatty methyl esters made for comparative purposes.
Original languageEnglish
JournalA C S Sustainable Chemistry & Engineering
Volume6
Issue number7
Pages (from-to)9442-9450
ISSN2168-0485
DOIs
Publication statusPublished - 2018

Keywords

  • Renewable
  • Epoxy
  • FDCA
  • UV
  • Thermoset

Cite this

@article{e146631001cc43ccb9dccd455caa9eed,
title = "Biobased Cationically Polymerizable Epoxy Thermosets from Furan and Fatty Acid Derivatives",
abstract = "In the pursuit of environmentally friendly building blocks in polymer chemistry the utilization of biobased monomers is highly desired. In the present study, the biobased monomer 2,5-furandicarboxylic acid (FDCA) has been extended into epoxy thermosets. The study presents the synthesis of diallyl furan-2,5-dicarboxylate (DAFDC) followed by an epoxidation of the allyls to form diglycidyl furan-2,5-dicarboxylate (DGFDC). DGFDC was then copolymerized in both stoichiometric and off-stoichiometric ratios with epoxidized fatty methyl esters to form a range of thermosets. The cross-linking reaction was either thermally or UV-induced cationic polymerization utilizing onium salt initiators where the reactivity was studied by DSC and real-time fourier transform infrared analysis. Furthermore, the structure–property relationships of the final thermosets were determined by dynamic mechanical thermal analysis revealing a possibility to tune the properties over a wide range. In addition thermosets were made from diglycidyl Bisphenol-A (DGEBA) with epoxidized fatty methyl esters made for comparative purposes.",
keywords = "Renewable, Epoxy, FDCA, UV, Thermoset",
author = "Samer Nameer and Larsen, {Daniel B.} and Duus, {Jens {\O}.} and Daugaard, {Anders E.} and Mats Johansson",
year = "2018",
doi = "10.1021/acssuschemeng.8b01817",
language = "English",
volume = "6",
pages = "9442--9450",
journal = "A C S Sustainable Chemistry & Engineering",
issn = "2168-0485",
publisher = "American Chemical Society",
number = "7",

}

Biobased Cationically Polymerizable Epoxy Thermosets from Furan and Fatty Acid Derivatives. / Nameer, Samer; Larsen, Daniel B.; Duus, Jens Ø.; Daugaard, Anders E.; Johansson, Mats.

In: A C S Sustainable Chemistry & Engineering, Vol. 6, No. 7, 2018, p. 9442-9450.

Research output: Contribution to journalJournal articleResearchpeer-review

TY - JOUR

T1 - Biobased Cationically Polymerizable Epoxy Thermosets from Furan and Fatty Acid Derivatives

AU - Nameer, Samer

AU - Larsen, Daniel B.

AU - Duus, Jens Ø.

AU - Daugaard, Anders E.

AU - Johansson, Mats

PY - 2018

Y1 - 2018

N2 - In the pursuit of environmentally friendly building blocks in polymer chemistry the utilization of biobased monomers is highly desired. In the present study, the biobased monomer 2,5-furandicarboxylic acid (FDCA) has been extended into epoxy thermosets. The study presents the synthesis of diallyl furan-2,5-dicarboxylate (DAFDC) followed by an epoxidation of the allyls to form diglycidyl furan-2,5-dicarboxylate (DGFDC). DGFDC was then copolymerized in both stoichiometric and off-stoichiometric ratios with epoxidized fatty methyl esters to form a range of thermosets. The cross-linking reaction was either thermally or UV-induced cationic polymerization utilizing onium salt initiators where the reactivity was studied by DSC and real-time fourier transform infrared analysis. Furthermore, the structure–property relationships of the final thermosets were determined by dynamic mechanical thermal analysis revealing a possibility to tune the properties over a wide range. In addition thermosets were made from diglycidyl Bisphenol-A (DGEBA) with epoxidized fatty methyl esters made for comparative purposes.

AB - In the pursuit of environmentally friendly building blocks in polymer chemistry the utilization of biobased monomers is highly desired. In the present study, the biobased monomer 2,5-furandicarboxylic acid (FDCA) has been extended into epoxy thermosets. The study presents the synthesis of diallyl furan-2,5-dicarboxylate (DAFDC) followed by an epoxidation of the allyls to form diglycidyl furan-2,5-dicarboxylate (DGFDC). DGFDC was then copolymerized in both stoichiometric and off-stoichiometric ratios with epoxidized fatty methyl esters to form a range of thermosets. The cross-linking reaction was either thermally or UV-induced cationic polymerization utilizing onium salt initiators where the reactivity was studied by DSC and real-time fourier transform infrared analysis. Furthermore, the structure–property relationships of the final thermosets were determined by dynamic mechanical thermal analysis revealing a possibility to tune the properties over a wide range. In addition thermosets were made from diglycidyl Bisphenol-A (DGEBA) with epoxidized fatty methyl esters made for comparative purposes.

KW - Renewable

KW - Epoxy

KW - FDCA

KW - UV

KW - Thermoset

U2 - 10.1021/acssuschemeng.8b01817

DO - 10.1021/acssuschemeng.8b01817

M3 - Journal article

VL - 6

SP - 9442

EP - 9450

JO - A C S Sustainable Chemistry & Engineering

JF - A C S Sustainable Chemistry & Engineering

SN - 2168-0485

IS - 7

ER -