Regioisomer-Specific Crystallization of Diglycidyl Ether of Bisphenol F Epoxy Resin

Jennifer Neu; Sara B. Isbill; Derek B. Dwyer; Joshua T. Damron; Andrew J. Miskowiec; Jennifer L. Niedziela

doi:10.1021/acs.chemmater.5c00723

Regioisomer-Specific Crystallization of Diglycidyl Ether of Bisphenol F Epoxy Resin

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Abstract

Diglycidyl ether of bisphenol F (DGEBF) is a common industrial epoxy resin, desired for its possible replacement of the bisphenol A (BPA) analogue DGEBA because of the potential health hazards of BPA. During curing, crystallization of the DGEBF resin can cause inaccurate resin-to-hardener ratios, resulting in incomplete cross-linking; therefore, understanding the crystallization of DGEBF is important for proper industrial control of the material. This work involved using a combination of single-crystal X-ray diffraction, Raman spectroscopy, and¹H NMR to investigate the crystallization of DGEBF. This report details the observed crystallization and crystal structures of two DGEBF regioisomers: ortho-ortho′-DGEBF and ortho-para′-DGEBF. Notably, para-para′-DGEBF crystallization was not observed, indicating that crystallization of this regioisomer does not occur under ambient conditions. Density functional theory calculations were performed to describe the phonon modes of the ortho-ortho′- and ortho-para′-DGEBF structures, corroborating Raman signatures for the respective isomers. Using a phonon mode analysis, three specific optical vibrational modes were identified at 631.3, 344.1, and 345.6 cm^–1that are unique to the para-monomer. This work offers insights into the crystallization behavior of DGEBF resins under ambient conditions and may inform potential industrial applications of this material.

Original language	English
Pages (from-to)	9037-9047
Number of pages	11
Journal	Chemistry of Materials
Volume	37
Issue number	22
DOIs	https://doi.org/10.1021/acs.chemmater.5c00723
State	Published - Nov 25 2025

Funding

This work was sponsored by the National Nuclear Security Administration. This research used resources of the Compute and Data Environment for Science (CADES) at Oak Ridge National Laboratory, which is supported by the US Department of Energy Office of Science under Contract number DE-AC05-00OR22725. This manuscript has been authored by UT-Battelle, LLC, under contract DE-AC05-00OR22725 with the US Department of Energy (DOE). The US government retains, and the publisher, by accepting the work for publication, acknowledges that the US government retains a nonexclusive, paid-up, irrevocable, worldwide license to publish or reproduce the submitted manuscript version of this work, or allow others to do so, for US government purposes. DOE will provide public access to these results of federally sponsored research in accordance with the DOE Public Access Plan (https://energy.gov/doe-public-access-plan).

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10.1021/acs.chemmater.5c00723

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title = "Regioisomer-Specific Crystallization of Diglycidyl Ether of Bisphenol F Epoxy Resin",

abstract = "Diglycidyl ether of bisphenol F (DGEBF) is a common industrial epoxy resin, desired for its possible replacement of the bisphenol A (BPA) analogue DGEBA because of the potential health hazards of BPA. During curing, crystallization of the DGEBF resin can cause inaccurate resin-to-hardener ratios, resulting in incomplete cross-linking; therefore, understanding the crystallization of DGEBF is important for proper industrial control of the material. This work involved using a combination of single-crystal X-ray diffraction, Raman spectroscopy, and1H NMR to investigate the crystallization of DGEBF. This report details the observed crystallization and crystal structures of two DGEBF regioisomers: ortho-ortho′-DGEBF and ortho-para′-DGEBF. Notably, para-para′-DGEBF crystallization was not observed, indicating that crystallization of this regioisomer does not occur under ambient conditions. Density functional theory calculations were performed to describe the phonon modes of the ortho-ortho′- and ortho-para′-DGEBF structures, corroborating Raman signatures for the respective isomers. Using a phonon mode analysis, three specific optical vibrational modes were identified at 631.3, 344.1, and 345.6 cm{\textendash}1that are unique to the para-monomer. This work offers insights into the crystallization behavior of DGEBF resins under ambient conditions and may inform potential industrial applications of this material.",

author = "Jennifer Neu and Isbill, \{Sara B.\} and Dwyer, \{Derek B.\} and Damron, \{Joshua T.\} and Miskowiec, \{Andrew J.\} and Niedziela, \{Jennifer L.\}",

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T1 - Regioisomer-Specific Crystallization of Diglycidyl Ether of Bisphenol F Epoxy Resin

AU - Neu, Jennifer

AU - Isbill, Sara B.

AU - Dwyer, Derek B.

AU - Damron, Joshua T.

AU - Miskowiec, Andrew J.

AU - Niedziela, Jennifer L.

PY - 2025/11/25

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N2 - Diglycidyl ether of bisphenol F (DGEBF) is a common industrial epoxy resin, desired for its possible replacement of the bisphenol A (BPA) analogue DGEBA because of the potential health hazards of BPA. During curing, crystallization of the DGEBF resin can cause inaccurate resin-to-hardener ratios, resulting in incomplete cross-linking; therefore, understanding the crystallization of DGEBF is important for proper industrial control of the material. This work involved using a combination of single-crystal X-ray diffraction, Raman spectroscopy, and1H NMR to investigate the crystallization of DGEBF. This report details the observed crystallization and crystal structures of two DGEBF regioisomers: ortho-ortho′-DGEBF and ortho-para′-DGEBF. Notably, para-para′-DGEBF crystallization was not observed, indicating that crystallization of this regioisomer does not occur under ambient conditions. Density functional theory calculations were performed to describe the phonon modes of the ortho-ortho′- and ortho-para′-DGEBF structures, corroborating Raman signatures for the respective isomers. Using a phonon mode analysis, three specific optical vibrational modes were identified at 631.3, 344.1, and 345.6 cm–1that are unique to the para-monomer. This work offers insights into the crystallization behavior of DGEBF resins under ambient conditions and may inform potential industrial applications of this material.

AB - Diglycidyl ether of bisphenol F (DGEBF) is a common industrial epoxy resin, desired for its possible replacement of the bisphenol A (BPA) analogue DGEBA because of the potential health hazards of BPA. During curing, crystallization of the DGEBF resin can cause inaccurate resin-to-hardener ratios, resulting in incomplete cross-linking; therefore, understanding the crystallization of DGEBF is important for proper industrial control of the material. This work involved using a combination of single-crystal X-ray diffraction, Raman spectroscopy, and1H NMR to investigate the crystallization of DGEBF. This report details the observed crystallization and crystal structures of two DGEBF regioisomers: ortho-ortho′-DGEBF and ortho-para′-DGEBF. Notably, para-para′-DGEBF crystallization was not observed, indicating that crystallization of this regioisomer does not occur under ambient conditions. Density functional theory calculations were performed to describe the phonon modes of the ortho-ortho′- and ortho-para′-DGEBF structures, corroborating Raman signatures for the respective isomers. Using a phonon mode analysis, three specific optical vibrational modes were identified at 631.3, 344.1, and 345.6 cm–1that are unique to the para-monomer. This work offers insights into the crystallization behavior of DGEBF resins under ambient conditions and may inform potential industrial applications of this material.

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DO - 10.1021/acs.chemmater.5c00723

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JO - Chemistry of Materials

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ER -

Regioisomer-Specific Crystallization of Diglycidyl Ether of Bisphenol F Epoxy Resin

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