Perfluorocyclobutyl-based methacrylate monomers: Synthesis and radical polymerization

Li, Yongjun; Zhang, Sen; Tong, Lewei; Li, Qingnuan; Li, Wenxin; Lu, Guolin; Líu, Hao; Huang, Xiaoyu

doi:10.1016/j.jfluchem.2008.12.012

Cited by 21 publications

(13 citation statements)

References 21 publications

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“…4-(2-(p-Tolyloxy)perfluorocyclobutoxy)phenol (2) was prepared according to the following procedures: 10 cross-dimerizatin of p-(trifluorovinyloxy)toluene and p-(trifluorovinyloxy)anisole and then the demethylation of the cross-dimer treated with BBr 3 . p-(2-(p-Tolyloxy)perfluorocyclobutoxy)phenyl acrylate (3) was prepared via the esterification of 4-(2-(p-tolyloxy)perfluorocyclobutoxy)phenol (2) and acrylic chloride.…”

Section: Preparation Of P-(2-(p-tolyloxy)perfluorocyclobutoxy)phenyl mentioning

confidence: 99%

“…10 The PFCBcontaining anisole 1, 4-(2-(p-tolyloxy)perfluorocyclobutoxy)anisole, was first prepared via the cross-coupling reaction between p-(trifluorovinyloxy)toluene and p-(trifluorovinyloxy)anisole, and then the anisole was demethylated by BBr 3 to give phenol 2 with an almost quantitative yield. Finally, acryloyl chloride was used to esterify 2 to provide the targeted PFCB-containing monomer 3, p-(2-(p-tolyloxy)perfluorocyclobutoxy)phenyl acrylate (TPFCBPA).…”

Section: Synthesis Of Tpfcbpa and Its Free Radical Homopolymerizationmentioning

confidence: 99%

“…[9][10][11] Compared with normal TFVE monomers, this kind of monomers can be polymerized via the traditional free radical polymerization as well as the living radical polymerization such as atom transfer radical polymerization (ATRP) and therefore, it enables direct chain copolymerization of this type of PFCB-containing monomers with usual vinyl monomers to afford the tailor-made polymers or copolymers with well-defined architecture and function, which has certainly widened the application of PFCB-based fluoropolymers.…”

Section: Introductionmentioning

confidence: 99%

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Perfluorocyclobutyl‐containing Amphiphilic Block Copolymers Synthesized by RAFT Polymerization

et al. 2009

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Amphiphilic block copolymers containing hydrophobic perfluorocyclobutyl-based (PFCB) polyacrylate and hydrophilic poly(ethylene glycol) (PEG) segments were prepared via reversible addition-fragmentation chain transfer (RAFT) polymerization. The PFCB-containing acrylate monomer, p-(2-(p-tolyloxy)perfluorocyclobutoxy)phenyl acrylate, was first synthesized from commercially available compounds in good yields, and this kind of acrylate monomer can be homopolymerized by free radical polymerization or RAFT polymerization. Kinetic study showed the 2,2'-azobis(isobutyronitrile) (AIBN) initiated and cumyl dithiobenzoate (CDB) mediated RAFT polymerization was in a living fashion, as suggested by the fact that the number-average molecular weights (M n ) increased linearly with the conversions of the monomer, while the polydispersity indices kept less than 1.10. The block polymers with narrow molecular weight distributions (M w /M n ≤1.21) were prepared through RAFT polymerization using PEG monomethyl ether capped with 4-cyanopentanoic acid dithiobenzoate end group as the macro chain transfer agent (mPEG-CTA). The length of the hydrophobic segment can be tuned by the feed ratio of the PFCB-based acrylate monomer and the extending of the polymerization time. The micellization behavior of the block copolymers in aqueous media was investigated by the fluorescence probe technique.

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Section: Preparation Of P-(2-(p-tolyloxy)perfluorocyclobutoxy)phenyl mentioning

confidence: 99%

Section: Synthesis Of Tpfcbpa and Its Free Radical Homopolymerizationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Perfluorocyclobutyl‐containing Amphiphilic Block Copolymers Synthesized by RAFT Polymerization

et al. 2009

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“…基间位质子峰, δ 7.03 处的 b 峰归属于苯环上羟基邻位质子峰 [19] , δ 9.64 处的 a 峰归属于羟基的质子峰. 从 PFCB2OH 的 19 F NMR 谱图(图 3)中可以看到, PFCB 的特征峰出现在 δ -128.08～-132.51 之间 [20,21] .…”

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“…通过 1 H NMR,19 F NMR, FT-IR 和 GPC 等手段对合成的聚合物进行表征. 图 5 为聚合物 PFCBPC 的核磁氢谱, δ 7.11～7.25 处的特征峰归属于苯环上羟基邻间位质子峰.…”

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Synthesis and Properties of Perfluorocyclobutyl Aryl Ether-Based Hydrophobic Polycarbonate

Hu¹,

Zhao²,

Tong³

et al. 2019

Chin. J. Org. Chem.

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A novel hydrophobic polycarbonate containing perfluorocyclobutyl (PFCB) aryl ether was synthesized from commercially available p-methoxyphenol. The polymer exhibited excellent thermal stability and hydrophobicity without reducing the transparency of the material. The thermal decomposition temperature was 351 ℃ and the contact angle between the film and water was 110°. In order to further explore the effect of PFCB aryl ether structure on the properties of polycarbonate, a series of polycarbonates with different PFCB aryl ether group contents were synthesized from PFCB aryl ether monomer and bisphenol A monomer. By comparing their properties, the introduction of PFCB aryl ether structure into polycarbonate can reduce its dispersion and improve its thermal stability and hydrophobicity.

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Preparation of segmented semifluorinated poly(aryl ether)s from aromatic trifluorovinyl ethers and oligo(ethylene glycol)s

Brown

Cracowski

Iacono

et al. 2015

J of Applied Polymer Sci

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A series of new segmented semifluorinated polyaryl ethers (PAEs) containing a biphenyl segmented by semifluorinated oligoethylene (SFE) units were prepared by nucleophilic addition of a commercial oligo(ethylene glycol)s to 4,4 0 -bis(4-trifluorovinyloxy)biphenyl. These new thermoplastics were characterized by 1 H and F 19 nuclear magnetic resonance (NMR) and attenuated total reflectance Fourier transform infrared (ATR-FTIR). Gel permeation chromatography (GPC) analysis displayed number average molecular weights (M n s) from 9000 to 13,000. Thermal properties of the polymers were studied by differential scanning calorimetry (DSC) and thermal gravimetric analysis (TGA). DSC chromatograms displayed glass transition temperatures (T g s) from 11 to 1 C. The onsets of degradations were observed by TGA analysis between 313 to 333 C in air and 326 to 363 C in nitrogen, respectively. A second onset of degradation was observed from 452 to 470 C for all polymers. In addition, crystalline morphologies were studied by tapping mode atomic force microscopy (TM-AFM) and showed needle-like crystallites.

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Perfluorocyclobutyl-based methacrylate monomers: Synthesis and radical polymerization

Cited by 21 publications

References 21 publications

Perfluorocyclobutyl‐containing Amphiphilic Block Copolymers Synthesized by RAFT Polymerization

Perfluorocyclobutyl‐containing Amphiphilic Block Copolymers Synthesized by RAFT Polymerization

Synthesis and Properties of Perfluorocyclobutyl Aryl Ether-Based Hydrophobic Polycarbonate

Preparation of segmented semifluorinated poly(aryl ether)s from aromatic trifluorovinyl ethers and oligo(ethylene glycol)s

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