Synthesis and characterization of a biphenyl perfluorocyclobutyl (BP‐PFCB) polyethylene glycol (PEG) blend compatibilizer

Brown, Dakarai K.; Iacono, Scott T.; Cracowski, Jean Marc; Christensen, Kenneth A.; Smith, Dennis W.

doi:10.1002/pat.3808

Cited by 3 publications

(6 citation statements)

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“…Over the past decades, many researchers around the world have been focused on the preparation of PFCB polymers [ 27 , 31 , 32 , 33 , 44 , 45 , 46 , 47 , 48 , 49 , 60 , 61 , 62 , 63 , 64 ]. Monomers containing TFVE moieties have been developed and used to obtain PFCB polymers [ 31 , 60 , 61 , 62 ].…”

Section: Synthesis Of Pfcb Polymersmentioning

confidence: 99%

“…The interest in polymer blend systems with minimum preparation steps for cost-effective processes and applications has rapidly increased over the last decades [ 44 , 46 , 67 ]. Polymer blend systems, which result in new materials with properties different from their parent components, are based on the physical combination of different polymers [ 44 , 67 ].…”

Section: Synthesis Of Pfcb Polymersmentioning

confidence: 99%

“…Polymer blend systems, which result in new materials with properties different from their parent components, are based on the physical combination of different polymers [ 44 , 67 ]. Although PFCB aryl ether polymers blended with fluorinated materials have been studied in the literature, less work on PFCB aryl ether blended with nonfluorinated monomers has been reported [ 44 , 46 ]. Brown et al [ 46 ] reported the compatibilization of PEG with a biphenyl perfluorocyclobutyl (BP-PFCB) aryl ether polymers ( Scheme 3 ).…”

Section: Synthesis Of Pfcb Polymersmentioning

confidence: 99%

“…Although PFCB aryl ether polymers blended with fluorinated materials have been studied in the literature, less work on PFCB aryl ether blended with nonfluorinated monomers has been reported [ 44 , 46 ]. Brown et al [ 46 ] reported the compatibilization of PEG with a biphenyl perfluorocyclobutyl (BP-PFCB) aryl ether polymers ( Scheme 3 ). Monomer 9 was synthesized in a one-step fashion via esterification of 4-(trifluorovinyloxy)benzoic acid (7) with PEG (8).…”

Section: Synthesis Of Pfcb Polymersmentioning

confidence: 99%

“…The cycloaddition of the fluoroolefins produces fluorinated cyclobutane rings, giving an overall amorphous PFCB polyaryl ethers with good solubility and solution processability for an array of new applications [ 9 , 11 , 12 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 ]. In the past decades, our group has been dedicated to the synthesis and applications of tailored PFCB polymers [ 12 , 20 , 44 , 45 , 46 , 47 , 48 , 49 ].…”

Section: Introductionmentioning

confidence: 99%

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Ring-Forming Polymerization toward Perfluorocyclobutyl and Ortho-Diynylarene-Derived Materials: From Synthesis to Practical Applications

et al. 2021

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Many desirable characteristics of polymers arise from the method of polymerization and structural features of their repeat units, which typically are responsible for the polymer’s performance at the cost of processability. While linear alternatives are popular, polymers composed of cyclic repeat units across their backbones have generally been shown to exhibit higher optical transparency, lower water absorption, and higher glass transition temperatures. These specifically include polymers built with either substituted alicyclic structures or aromatic rings, or both. In this review article, we highlight two useful ring-forming polymer groups, perfluorocyclobutyl (PFCB) aryl ether polymers and ortho-diynylarene- (ODA) based thermosets, both demonstrating outstanding thermal stability, chemical resistance, mechanical integrity, and improved processability. Different synthetic routes (with emphasis on ring-forming polymerization) and properties for these polymers are discussed, followed by their relevant applications in a wide range of aspects.

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Section: Synthesis Of Pfcb Polymersmentioning

confidence: 99%

Section: Synthesis Of Pfcb Polymersmentioning

confidence: 99%

Section: Synthesis Of Pfcb Polymersmentioning

confidence: 99%

Section: Synthesis Of Pfcb Polymersmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Ring-Forming Polymerization toward Perfluorocyclobutyl and Ortho-Diynylarene-Derived Materials: From Synthesis to Practical Applications

et al. 2021

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Thiol–Trifluorovinyl Ether (TFVE) Photopolymerization: An On-Demand Synthetic Route to Semifluorinated Polymer Networks

2016

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We report a first example of thiol−trifluorovinyl ether (thiol−TFVE) photopolymerization as a facile, cure-ondemand synthetic route to semifluorinated polymer networks. The thiol−TFVE reactionwhich proceeds via anti-Markovnikov addition of a thiyl radial to the TFVE groupwas elucidated using model small molecule reactions between phenyl trifluorovinyl ether and thiols with varying reactivity. These model reactions, characterized by 19 F NMR, 1 H NMR, and FTIR, also provided evidence of an oxygen-induced degradation pathway that may be circumvented by performing the reactions under an inert gas atmosphere. Photopolymerization of difunctional TFVE monomers with multifunctional thiols occurred with rapid kinetics and high conversions as observed with real-time FTIR and provided homogeneous semifluorinated polymer networks with narrow glass transitions as observed with dynamic mechanical analysis. The semifluorinated ether/thioether linkage incorporated into the polymer network yielded hydrophobic materials with increased and tunable T g , a 2-fold increase in strain at break, 4-fold increase in stress at break, and more than 5-fold increase in toughness relative to a thiol−ene material composed of a structurally similar hydrogenated ether/thioether linkage. The increased T g and mechanical toughness are attributed to the higher rigidity, hydrogenbonding capacity, and stronger carbon−carbon bonds of the semifluorinated ether/thioether relative to the hydrogenated ether/ thioether.

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Perfluorocyclobutyl-based polymers for functional materials

Zhou¹,

Tao²,

Chen³

et al. 2019

Mater. Chem. Front.

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Synthesis and characterization of a biphenyl perfluorocyclobutyl (BP‐PFCB) polyethylene glycol (PEG) blend compatibilizer

Cited by 3 publications

References 29 publications

Ring-Forming Polymerization toward Perfluorocyclobutyl and Ortho-Diynylarene-Derived Materials: From Synthesis to Practical Applications

Ring-Forming Polymerization toward Perfluorocyclobutyl and Ortho-Diynylarene-Derived Materials: From Synthesis to Practical Applications

Thiol–Trifluorovinyl Ether (TFVE) Photopolymerization: An On-Demand Synthetic Route to Semifluorinated Polymer Networks

Perfluorocyclobutyl-based polymers for functional materials

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