Aromatic tetra-glycidyl ether versus tetra-glycidyl amine epoxy networks: Influence of monomer structure and epoxide conversion

Samuel Swan; Claudia Creighton; James M. Griffin; Bekim V Gashi; Russell J. Varley

doi:10.1016/j.polymer.2021.124401

Aromatic tetra-glycidyl ether versus tetra-glycidyl amine epoxy networks: Influence of monomer structure and epoxide conversion

Samuel Swan, Claudia Creighton, James M. Griffin, Bekim V Gashi, Russell J. Varley

Deakin University

Research output: Contribution to journal › Article › peer-review

15 Citations (Scopus)

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Abstract

In this work, two epoxy resins, bis(2,7 glycidyl ether naphthalenediol) methane (NNE), tetraglycidyl diaminodiphenylmethane (TGDDM) and a miscible blend of the two are cured with 4,4′-diaminodiphenylsulfone (DDS) to investigate the differences between glycidyl ether and glycidyl amine crosslinked networks. This work explores in depth, and directly compares for the first time, the structure/property relationships of a highly aromatic and thermally stable glycidyl ether epoxy network with a well-known highly aromatic and thermally stable glycidyl amine epoxy network. The highly aromatic naphthalene motif of NNE imparts improved thermal stability and a significantly higher glass transition temperature, above 340 °C depending on the measurement technique. However, it also produces comparatively lower epoxide conversion, higher moisture ingress and lower flexural properties. These properties are attributed to the NNE having higher free volume and glassy state mobility as suggested by the sub-ambient β relaxations. The glycidyl ether groups react primarily via epoxide amino addition displaying only very minor evidence of homopolymerisation or other side reactions even at 240 °C. This contrasts with the glycidyl amine groups of TGDDM which exhibit a much higher degree of non-epoxy amine addition. Increasing cure conversion also increases the glass transition temperature, fracture toughness and reduced coefficient of thermal expansion. Overall, the results show that despite some reduced mechanical and thermal properties the NNE epoxy resin system is a very thermally stable high temperature epoxy resin based upon glycidyl ether functional groups suitable for a wide range of new applications.

Original language	English
Article number	124401
Number of pages	11
Journal	Polymer
Volume	239
Early online date	29 Nov 2021
DOIs	https://doi.org/10.1016/j.polymer.2021.124401
Publication status	Published - 17 Jan 2022

Bibliographical note

© 2022, Elsevier. Licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/

Copyright © and Moral Rights are retained by the author(s) and/ or other copyright owners. A copy can be downloaded for personal non-commercial research or study, without prior permission or charge. This item cannot be reproduced or quoted extensively from without first obtaining permission in writing from the copyright holder(s). The content must not be changed in any way or sold commercially in any format or medium without the formal permission of the copyright holders.

This document is the author’s post-print version, incorporating any revisions agreed during the peer-review process. Some differences between the published version and this version may remain and you are advised to consult the published version if you wish to cite from it.

Funder

Professor Russell J. Varley gratefully acknowledges support by the Australian Research Council (DP1801 00094) and the Office of Naval Research Global (N62909-18-1-2024).

Keywords

epoxy resins
Structure-property relations
Thermal stability
Moisture ingress

ASJC Scopus subject areas

Materials Science(all)

Access to Document

10.1016/j.polymer.2021.124401

Post-PrintAccepted author manuscript, 2.59 MBLicence: CC BY-NC-ND

Cite this

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abstract = "In this work, two epoxy resins, bis(2,7 glycidyl ether naphthalenediol) methane (NNE), tetraglycidyl diaminodiphenylmethane (TGDDM) and a miscible blend of the two are cured with 4,4′-diaminodiphenylsulfone (DDS) to investigate the differences between glycidyl ether and glycidyl amine crosslinked networks. This work explores in depth, and directly compares for the first time, the structure/property relationships of a highly aromatic and thermally stable glycidyl ether epoxy network with a well-known highly aromatic and thermally stable glycidyl amine epoxy network. The highly aromatic naphthalene motif of NNE imparts improved thermal stability and a significantly higher glass transition temperature, above 340 °C depending on the measurement technique. However, it also produces comparatively lower epoxide conversion, higher moisture ingress and lower flexural properties. These properties are attributed to the NNE having higher free volume and glassy state mobility as suggested by the sub-ambient β relaxations. The glycidyl ether groups react primarily via epoxide amino addition displaying only very minor evidence of homopolymerisation or other side reactions even at 240 °C. This contrasts with the glycidyl amine groups of TGDDM which exhibit a much higher degree of non-epoxy amine addition. Increasing cure conversion also increases the glass transition temperature, fracture toughness and reduced coefficient of thermal expansion. Overall, the results show that despite some reduced mechanical and thermal properties the NNE epoxy resin system is a very thermally stable high temperature epoxy resin based upon glycidyl ether functional groups suitable for a wide range of new applications.",

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AU - Varley, Russell J.

N1 - © 2022, Elsevier. Licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ Copyright © and Moral Rights are retained by the author(s) and/ or other copyright owners. A copy can be downloaded for personal non-commercial research or study, without prior permission or charge. This item cannot be reproduced or quoted extensively from without first obtaining permission in writing from the copyright holder(s). The content must not be changed in any way or sold commercially in any format or medium without the formal permission of the copyright holders. This document is the author’s post-print version, incorporating any revisions agreed during the peer-review process. Some differences between the published version and this version may remain and you are advised to consult the published version if you wish to cite from it.

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Aromatic tetra-glycidyl ether versus tetra-glycidyl amine epoxy networks: Influence of monomer structure and epoxide conversion

Abstract

Bibliographical note

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Keywords

ASJC Scopus subject areas

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