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Step-Growth Copolymerization of Cyclic and Acyclic Perfluoroolefins with Bisphenols

lssue 4, Volume 4
Part of Special Issue Polymer Materials Synthesis, Design and Applications
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Step-Growth Copolymerization of Cyclic and Acyclic Perfluoroolefins with Bisphenols

Erfan Masaeli 1 Maxim E. Solovyev 1 Gustavo Muñoz 1 William W. Johnson 1 Elnaz Janghorban 2 Giovanni Octavio Martinez Ortega 1 Charles U. Pittman, Jr. 1 Dennis W. Smith, Jr. 1,*

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1
Department of Chemistry, Mississippi State University, Mississippi State, MS 39762, USA
2
Department of Sustainable Bioproducts, Mississippi State University, Starkville, MS 39759, USA
*
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Received: 22 July 2026 Revised: 06 August 2026 Accepted: 22 September 2026 Published: 12 October 2026

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© 2026 The authors. This is an open access article under the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0/).

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Sustain. Polym. Energy 2026, 4(4), 10017; DOI: 10.70322/spe.2026.10017
ABSTRACT: Base-initiated copolymerization of bisphenols with cyclic and acyclic perfluoroolefins was investigated as an extension of addition–elimination polymerization toward compositionally variable feedstocks that model (per-and polyfluoroalkyl substances) PFAS waste. Perfluoro-4-methylpent-2-ene (PFP), perfluorohept-1-ene (PFH), perfluorocyclohexene (PFCH), and perfluorocyclopentene (PFCP) were paired in selected combinations and reacted in the presence of bisphenol-A (BPA) and bisphenol-AF (BPF), respectively, under basic conditions to generate a series of semi-fluorinated copolymers. These reactions yielded copolymers containing fluorinated segments derived from both cyclic and acyclic olefin comonomers. Structural incorporation and copolymer compositions were evaluated by nuclear magnetic resonance and infrared spectroscopy, while molecular mass and thermal behavior were examined by gel permeation chromatography, differential scanning calorimetry, and thermogravimetric analysis. The resulting copolymers exhibited broad compositional and thermal variability while retaining unsaturated fluorinated sites capable of further reaction, such as capable of further thermal reactivity. These results establish structurally distinct perfluoroolefins as model fluorinated feedstocks for investigating addition–elimination polymerization and provide a foundation for future studies using more compositionally complex fluorinated feedstocks.
Keywords: Fluoropolymers; PFAS derivatives; Perfluoro cycloolefin copolymerization; Addition–elimination chemistry; Bisphenols; Thermal reactivity
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