Synthesis of α,β-unsaturated esters of perfluoropolyalkylethers (PFPAEs) based on hexafluoropropylene oxide units for photopolymerization

Bonneaud, Céline; Decostanzi, Mélanie; Burgess, Julia; Trusiano, Giuseppe; Burgess, Trevor; Bongiovanni, Roberta Maria; Joly‐Duhamel, Christine; Friesen, Chadron M.

doi:10.1039/c8ra06354k

Cited by 11 publications

(15 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…These degradation temperatures demonstrate a good thermal resistance in comparison to a previous study about the copolymers (maleate‐ alt ‐vinyl ether) PFPAEs . The most thermally stable homopolymer M2 C10 ( T 10% ‐ 10 K/min: 360 °C in N 2 and 292 °C in air—Figure ) showed higher thermal stability than crosslinked PFPAEs with acrylate bonds ( T 10% ‐ N 2 = 256–280 °C) .…”

Section: Resultssupporting

confidence: 50%

See 1 more Smart Citation

Photopolymerization of maleimide perfluoropolyalkylethers without a photoinitiator

Bonneaud

Burgess

Bongiovanni

et al. 2018

J. Polym. Sci. Part A: Polym. Chem.

Self Cite

View full text Add to dashboard Cite

Perfluoropolyalkylethers derived from hexafluoropropylene oxide were functionalized with maleimide groups. Irradiated by UV‐light, the new maleimide macromonomers demonstrated very fast polymerization kinetics with a curing time as fast as 8 s. The effect on photopolymerization of different features such as the molecular weight of the fluorinated chain and the chain length of the hydrogenated spacer were studied, as well as the influence of the type of photoinitiator and the presence of air. Thermal and surface properties of the UV‐cured polymers were examined and were typical to fluoropolymers in view of water–oil repellent coatings. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 699–707

show abstract

Section: Resultssupporting

confidence: 50%

“…However, 4a‐c (containing the longer fluorinated chains) did not reach complete conversion by Route A. Previous work has shown Steglich esterification to provide a facile route for oligo (HFPO) methylene alcohol esterification, and this method enabled the successful synthesis of 4a‐c (Route B) …”

Section: Resultsmentioning

confidence: 99%

Photopolymerization of maleimide perfluoropolyalkylethers without a photoinitiator

Bonneaud

Burgess

Bongiovanni

et al. 2018

J. Polym. Sci. Part A: Polym. Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

“…PFPAEs can also be used as interesting building blocks for preparing monomers reactive in photopolymerization [8,16,20,21]. In this work, new PFPAE oligomers were synthesized by the anionic ring-opening reaction of hexafluoropropylenoxide (HFPO) with cesium fluoride and functionalized with an -OH end group [22].…”

Section: Introductionmentioning

confidence: 99%

Modification of photocurable epoxides by new perfluoropolyalkylether alcohols for obtaining self-cleaning coatings

Trusiano

Rizzello

Vitale

et al. 2019

Progress in Organic Coatings

Self Cite

View full text Add to dashboard Cite

Perfluoropolyalkylether (PFPAE) structures can be functionalized with alcoholic groups using an appropriate synthetic pathway: these new fluorinated alcohols can be used as surface modifying agents, through chain transfer mechanism in cationic UV-curing of an epoxy system. Notwithstanding their very low concentration (only ≤5 wt%), the fluorinated alcohols are able to induce a dramatic improvement to the surface properties of the films, without substantially modifying their curing conditions and their bulk properties, neither their transparency. As confirmed by Fourier Transform-Infra Red (FT-IR) spectroscopy and X-ray photoelectron spectroscopy (XPS) measurements, the fluorinated comonomers tend to concentrate selectively at the outermost layer of the epoxy UVcured coatings, by spontaneously migrating to the free surface due to their low surface tension. The surface modification of the films depends on the concentration of the fluoroalcohols: coatings

show abstract

“…For these reasons, PFPAEs have previously been explored containing functionalization with acrylic [23,24], methacrylic [10,[25][26][27][28], or maleimidic [29,30] end-groups to be used in radical photopolymerization. It is well known that this process suffers from oxygen inhibition; this drawback is even more severe for fluorinated products, as they show a high oxygen solubility.…”

Section: Introductionmentioning

confidence: 99%

Novel perfluoropolyalkylethers monomers: synthesis and photo-induced cationic polymerization

et al. 2021

Self Cite

View full text Add to dashboard Cite

Several difunctional oligomers were synthesized by functionalizing perfluoropolyalkylether (PFPAE) chains with different vinyl ethers and epoxides end-groups. Due to their innate synthetic challenges and demanding purification protocols, the PFPAE derivatives were obtained in low yield and with an average functionality lower than 2. However, the functionalized PFPAE oligomers were successful in being used in photo-induced cationic polymerization processes, obtaining transparent and soft films. The influences of the fluorinated chains, and various end-groups on the photopolymerization process were investigated, as well their chemical stability, thermal degradation, and surface properties. Graphical abstract

show abstract

Synthesis of α,β-unsaturated esters of perfluoropolyalkylethers (PFPAEs) based on hexafluoropropylene oxide units for photopolymerization

Abstract: Hydrophobic macromonomers synthesized by Steglich esterification to generate UV-curable materials.

Cited by 11 publications

References 31 publications

Photopolymerization of maleimide perfluoropolyalkylethers without a photoinitiator

Photopolymerization of maleimide perfluoropolyalkylethers without a photoinitiator

Modification of photocurable epoxides by new perfluoropolyalkylether alcohols for obtaining self-cleaning coatings

Novel perfluoropolyalkylethers monomers: synthesis and photo-induced cationic polymerization

Contact Info

Product

Resources

About