Advances in the (co)polymerization of alkyl 2-trifluoromethacrylates and 2-(trifluoromethyl)acrylic acid

Patil, Yogesh; Améduri, Bruno

doi:10.1016/j.progpolymsci.2012.09.005

Cited by 65 publications

(88 citation statements)

References 162 publications

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“…The homopolymerization of VAc initiated by 2,2′‐azobis (4‐methoxy‐2,4‐dimethylvaleronitrile) (V‐70) in the presence of [Co(acac) 2 ] at 40 °C produced PVAc with controlled molar mass ( M n = 28 200 g mol −1 ) and low dispersity ( Đ = 1.16), as previously described (entry 1 in Table S1 and Figure S1, Supporting Information). In contrast, attempts to obtain a MAF‐TBE homopolymer under the same conditions failed (entry 2, Table S1, Supporting Information), as expected, since MAF‐TBE does not homopolymerize under radical conditions …”

Section: Resultssupporting

confidence: 52%

“…Although homopolymers can be produced anionically, these monomers do not homopolymerize under radical conditions, but can be copolymerized together with electron‐donating monomers such as vinyl ethers . MAF‐ and MAF‐esters containing fluorinated copolymers led to suitable materials for molecularly imprinted polymers, microlithography, polymer electrolyte membranes for fuel cells and for Li‐ion batteries . Recently, a nitroxide‐mediated alternating copolymerization of VAc and MAF‐TBE has been achieved .…”

Section: Introductionmentioning

confidence: 99%

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Organometallic‐Mediated Alternating Radical Copolymerization of tert‐Butyl‐2‐Trifluoromethacrylate with Vinyl Acetate and Synthesis of Block Copolymers Thereof

Banerjee

Ladmiral

Debuigne

et al. 2017

Macromol. Rapid Commun.

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Organometallic-mediated radical polymerization (OMRP) has given access to well-defined poly(vinyl acetate-alt-tert-butyl-2-trifluoromethacrylate)-b-poly(vinyl acetate) and poly(VAc-alt-MAF-TBE) copolymers composed of two electronically distinct monomers: vinyl acetate (VAc, donor, D) and tert-butyl-2-trifluoromethacrylate (MAF-TBE, acceptor, A), with low dispersity (≤1.24) and molar masses up to 57 000 g mol . These copolymers have a precise 1:1 alternating structure over a wide range of comonomer feed compositions. The reactivity ratios are determined as r = 0.01 ± 0.01 and r = 0 at 40 °C. Remarkably, from a feed containing >50% molar VAc content, poly(VAc-alt-MAF-TBE)-b-PVAc block copolymers are produced via a one-pot synthesis. Such diblock copolymers exhibit two glass transition temperatures attributed to the alternating and homopolymer sequences. The OMRP of this fluorine-containing alternating monomer system may provide access to a wide range of new polymer materials.

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Section: Resultssupporting

confidence: 52%

Section: Introductionmentioning

confidence: 99%

Organometallic‐Mediated Alternating Radical Copolymerization of tert‐Butyl‐2‐Trifluoromethacrylate with Vinyl Acetate and Synthesis of Block Copolymers Thereof

Banerjee

Ladmiral

Debuigne

et al. 2017

Macromol. Rapid Commun.

Self Cite

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“… Synthesis of different functional 2‐trifluoromethacrylates (MAF‐esters) from 2‐trifluoromethacrylic acid and their radical copolymerizations for specific materials …”

Section: Applicationsmentioning

confidence: 99%

“…[20,21] Scheme2.Synthesis of different functional 2-trifluoromethacrylates (MAFesters) from 2-trifluoromethacrylic acid andtheir radical copolymerizations for specific materials. [23][24][25][26][27] Figure 2. Original Lumiflon (X = Cl) or Zeffle (X = F) resins/paintsb ased on an alternatedstructure containingC TFE or TFE and functional vinyl ether units.…”

Section: Coatingsmentioning

confidence: 99%

Fluoropolymers: The Right Material for the Right Applications

Améduri

2018

Chemistry A European J

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135

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An overview on the synthesis, properties, and applications of fluoropolymers (PFs) is presented. First, a non-exhaustive summary on the homopolymers from conventional radical polymerization of fluoromonomers is proposed. FPs are interesting materials thanks to their outstanding properties such as thermal, oxidative and chemical resistances, low dissipation factor, refractive index, permittivity, and water absorptivity, as well as excellent durability and weatherability. Various strategies of synthesis are proposed, especially on recent studies on radical (co)polymerization of fluoroalkenes, just like their properties and applications ranging from coatings and energy-related materials (e.g. fuel cell membranes, components for lithium ion batteries, electroactive devices, and photovoltaics) to original fluorinated elastomers, surfactants, thermoplastic elastomers, thermostables, and optical devices.

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“…Owing to the unique structure and superior performances, methacrylate-based monomers and polymers have attracted much attentions [1][2][3], especially for the fluorinated ones. For example, it was reported that fluorinated methacrylate polymers have excellent surface properties, impressive optical performances [4,5] and thus are extensively applied in the fields of ice-phobic coatings, functional thin film, medical materials, optical devices/fiber and nanocomposites [6][7][8][9][10]. Among the methacrylates, alkyl 2-trifluoromethacrylate(s) is suggested to be less active since a strong inductive electron-withdrawing trifluoromethyl group (-CF 3 ) is connected to the α position [11].…”

Section: Introductionmentioning

confidence: 99%

Insight into the Intermolecular Interaction and Free Radical Polymerizability of Methacrylates in Supercritical Carbon Dioxide

Wang

Zhang

et al. 2020

Polymers

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High pressure in situ Fourier transfer infrared/near infrared technology (HP FTIR/NIR) along with theoretical calculation of density functional theory (DFT) method was employed. The solvation behaviors and the free radical homopolymerization of methyl methacrylate (MMA), methacrylate acid (MAA), trifluoromethyl methacrylate (MTFMA) and trifluoromethyl methacrylate acid (TFMAA) in scCO2 were systematically investigated. Interestingly, the previously proposed mechanism of intermolecular-interaction dynamically-induced solvation effect (IDISE) of monomer in scCO2 is expected to be well verified/corroborated in view that the predicted solubility order of the monomers in scCO2 via DFT calculation is ideally consistent with that observed via HP FTIR/NIR. It is shown that MMA and MAA can be easily polymerized, while the free radical polymerizability of MTFMA is considerably poor and TFMAA cannot be polymerized via the free radical initiators. The α trifluoromethyl group (–CF3) may effectively enhance the intermolecular hydrogen bonding and restrain the diffusion of the monomer in scCO2. More importantly, the strong electron-withdrawing inductive effect of –CF3 to C=C may distinctly decrease the atomic charge of the carbon atom in the methylene (=CH2). These two factors are believed to be predominantly responsible for the significant decline of the free radical polymerizability of MTFMA and the other alkyl 2-trifluoromethacrylates in scCO2.

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Advances in the (co)polymerization of alkyl 2-trifluoromethacrylates and 2-(trifluoromethyl)acrylic acid

Cited by 65 publications

References 162 publications

Organometallic‐Mediated Alternating Radical Copolymerization of tert‐Butyl‐2‐Trifluoromethacrylate with Vinyl Acetate and Synthesis of Block Copolymers Thereof

Organometallic‐Mediated Alternating Radical Copolymerization of tert‐Butyl‐2‐Trifluoromethacrylate with Vinyl Acetate and Synthesis of Block Copolymers Thereof

Fluoropolymers: The Right Material for the Right Applications

Insight into the Intermolecular Interaction and Free Radical Polymerizability of Methacrylates in Supercritical Carbon Dioxide

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