On the sulfonation of fluorinated aromatic polymers: Synthesis, characterization and effect of fluorinated side groups on sulfonation degree

Wolska, Joanna; Walkowiak-Kulikowska, Justyna

doi:10.1016/j.eurpolymj.2020.109635

Cited by 15 publications

(5 citation statements)

References 79 publications

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“…This may be indicative of the thioether undergoing oxidation and thus stabilizing the polymers before ultimately affording no residual char and has not been reported previously with PFCP modified polymers. The thermal stability of the polymers was comparable or above average in comparison to other known fluorinated sulfur‐containing polymers 23–25 …”

Section: Resultsmentioning

confidence: 74%

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Synthesis and characterization of perfluorocyclopentene‐thioether polymers

Bishop,

Balmaceda,

Iacono

et al. 2024

Polymer International

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Due to their unique properties and use in high performance materials, the ability to obtain fluorinated polymers utilizing straightforward synthetic methods remains of interest. In this study, we report the facile synthesis of new fluoropolymers via nucleophilic addition of a di‐thiol to perfluorocyclopentene. Initially, model studies were completed with perfluorocyclopentene and benzenethiol and TMS‐protected benzenethiol to identify the optimal reaction conditions for the polymerization. These reaction conditions were then utilized to prepare perfluorocyclopentene‐thioether polymers from perfluorocyclopentene and 4, 4′‐thiobisbenzenethiol. The isolated polymers had molecular weight distributions consistent with step‐growth polymers and 19F NMR spectroscopy revealed that the addition of the nucleophile to perfluorocyclopentene was controlled. Analysis by differential scanning calorimetry showed that the polymers were amorphous with glass transition temperatures around 65 °C. Thermogravimetric analysis in both air and nitrogen showed an initial degradation temperature around 370 °C, while the air analysis produced an additional plateau with a degradation temperature near 592 °C. This is the first known report of utilizing perfluorocyclopentene for the preparation of perfluorinated‐thioether polymers.This article is protected by copyright. All rights reserved.

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Section: Resultsmentioning

confidence: 74%

“…The thermal stability of the polymers was comparable or above average in comparison to other known fluorinated sulfur-containing polymers. [23][24][25]…”

Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of perfluorocyclopentene‐thioether polymers

Bishop,

Balmaceda,

Iacono

et al. 2024

Polymer International

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“…Similarly, comparing the morphology of PPBEK and PPEK, revealed that PPBEK displayed better toughness than PPEK, which was due to the introduction of BP to make the ether bond increase and improve the flexibility of molecular structure. The toughness of PPBESK was lower than that of PPBEK due to the presence of the sulfone group in the molecular chain structure, which increased the rigidity of the molecular chain and made it difficult to rotate internally 34 …”

Section: Resultsmentioning

confidence: 99%

“…The toughness of PPBESK was lower than that of PPBEK due to the presence of the sulfone group in the molecular chain structure, which increased the rigidity of the molecular chain and made it difficult to rotate internally. 34 The specimens before and after impact were observed by SEM, as shown in Figure 3. The nine resin specimens underwent the same polishing treatment before impact, so the SEM images of the impacted specimens before impact were essentially identical with no discernible differences.…”

Section: Oxidation Resistance and Liquid Oxygen Compatibility Of Poly...mentioning

confidence: 99%

Study on liquid oxygen compatibility of poly(phthalazinone ether) resins and their composites

Wang,

Li,

et al. 2024

Polymer Composites

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Nine poly(phthalazinone ether ketone) resins were designed and synthesized using three bisphenol and four halogenated monomers. Poly(phthalazinone bisphenol ether ketone) (PPBEK) and poly(phthalazinone ether sulfone ketone) (PPBESK) demonstrated liquid oxygen compatibility (LOC), with PPBEK maintaining its LOC even after 20 days of immersion in liquid oxygen. The liquid oxygen compatibility mechanism of the polymers in the presence of force‐thermal‐chemical multi‐energy fields was analyzed using techniques such as thermal analysis‐infrared‐gas chromatography (TGA‐IR‐GC), thermogravimetric analysis (TGA), and x‐ray photoelectron spectroscopy (XPS). Carbon fiber (CF) reinforced composites were fabricated using PPBEK and PPBESK as matrices, with CF‐PPBEK composites successfully achieving LOC. The microcracking resistance and mechanical properties of the composites were investigated in liquid oxygen at 90 K. The interaction mechanism between the composites and liquid oxygen was elucidated, providing theoretical guidance and an experimental foundation for the application of resin matrix composites in liquid oxygen storage tanks.Highlights Poly(phthalazinone ether) resins were meticulously designed and synthesized. ·PPBEK and PPBESK exhibited excellent liquid oxygen compatibility. Composites exhibited excellent liquid oxygen compatibility. Composites exhibited excellent low‐temperature performance and heat resistance.

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“…Even though acetylsulfate (ACS) has been known for some time [37,38], this reagent has not been used to sulfonate the PSU, due to a lack of work in the literature. It is mentioned by Smitha et al [33] as a reaction that does not occur due to its incompatibility between PSU and ACS.…”

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confidence: 99%

Polysulfone with Different Degrees of Sulfonation: Simple Method with Acetyl Sulfate

Xavier de Souza,

Frighetto,

Badagnani de Carvalho

et al. 2024

Orbital: Electron. J. Chem.

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In this work, the authors present as an innovation, the homogeneous sulfonation of Udel® polysulfone (PSU) with acetylsulfate (ACS) under reflux at 45°C in dichloromethane and inert N2 atmosphere (g) for 1.5 h. Different proportions of ACS were used, obtaining sulfonated products with varying degrees of sulfonation (DS). Confirmation of sulfonated polysulfone (PSU-S), denominated as PSU-SA (high degree of sulfonation) and PSU-SB (low degree of sulfonation), was carried out by FTIR and 1H NMR. Determination of DS was carried out through thermogravimetric analysis (TGA/DSC), varying indexes between 0.883 and 3.022, which correspond to a sulfonated polymer with ion exchange capacity (IEC) from 1.720 to 4.400 meq/g. The evolution of DS related to methods used was monitored and confirmed by 1H NRM. Sulfonation is undertaken to enhance the suitability of this polymer for future applications in the production of biofuels, targeting its utilization in catalytic processes for esterification and transesterification mechanisms of oils and fats.

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On the sulfonation of fluorinated aromatic polymers: Synthesis, characterization and effect of fluorinated side groups on sulfonation degree

Cited by 15 publications

References 79 publications

Synthesis and characterization of perfluorocyclopentene‐thioether polymers

Synthesis and characterization of perfluorocyclopentene‐thioether polymers

Study on liquid oxygen compatibility of poly(phthalazinone ether) resins and their composites

Polysulfone with Different Degrees of Sulfonation: Simple Method with Acetyl Sulfate

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