Membranes for gas separation based on silylated polyphenylene oxide

Perego, G.; Roggero, A.; Sisto, R.; Valentini, C.

doi:10.1016/s0376-7388(00)80586-4

Cited by 26 publications

(16 citation statements)

References 7 publications

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“…Nuclear magnetic resonance spectra were recorded on a Varian Unity Inova spectrometer at a resonance frequency of 399.961 MHz for 1 H and 100.579 MHz for 13 C. Polymer samples were prepared using CDCl3 as the NMR solvent, and the chloroform signals were used as the chemical shift reference ( 1 HCHCl3 7.25 ppm, 13 C CDCl3 77.00 ppm). 2D carbon-hydrogen correlation (HETCOR) spectra were recorded for one-bond 1 J C-H (140 Hz) and three-bond 3 J C-H (7.5 Hz) spin correlations.…”

Section: Synthesis Of Tm6fpsf-s-tms (Ortho Sulfone)mentioning

confidence: 99%

Preparation and Characterization of Polysulfones Containing Both Hexafluoroisopropylidene and Trimethylsilyl Groups as Gas Separation Membrane Materials

Dai¹,

Guiver²,

Robertson³

et al. 2004

Macromolecules

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/npsi/ctrl?action=rtdoc&an=8906267&lang=en http://nparc.cisti-icist.nrc-cnrc.gc.ca/npsi/ctrl?action=rtdoc&an=8906267&lang=frAccess and use of this website and the material on it are subject to the Terms and Conditions set forth at http://nparc.cisti-icist.nrc-cnrc.gc.ca/npsi/jsp/nparc_cp.jsp?lang=en NRC Publications Archive Archives des publications du CNRCThis publication could be one of several versions: author's original, accepted manuscript or the publisher's version. / La version de cette publication peut être l'une des suivantes : la version prépublication de l'auteur, la version acceptée du manuscrit ou la version de l'éditeur. For the publisher's version, please access the DOI link below./ Pour consulter la version de l'éditeur, utilisez le lien DOI ci-dessous.http://dx.doi.org/10.1021/ma035739i Macromolecules, 37, 4, pp. 1403Macromolecules, 37, 4, pp. -1410Macromolecules, 37, 4, pp. , 2004 Preparation and characterization of polysulfones containing both hexafluoroisopropylidene and trimethylsilyl groups as gas separation membrane materials Dai, Y.; Guiver, Michael; Robertson, Gilles; Kang, Y.; Lee, Kunchan; Jho, J. Science and Technology, P.O. Box 131, Cheongryang, Seoul 130-650, Korea; and Hyperstructured Organic Materials Research Center and School of Chemical Engineering, Seoul National University, Seoul 151-744, Korea Received November 19, 2003; Revised Manuscript Received December 16, 2003 ABSTRACT: Trimethylsilylated derivatives of hexafluoropolysulfone (6FPSf) and tetramethylhexafluoropolysulfone (TM6FPSf) were prepared by reaction of lithiated polymer intermediates with halotrimethylsilane electrophiles for a membrane gas separation study to compare improvements in gas permeabilities with those of unmodified polymers. Ortho sulfone substituted 6FPSf and TM6FPSf having pendant trimethylsilyl (TMS) groups were obtained by a two-step process involving first direct lithiation of 6FPSf and TM6FPSf solutions with n-butyllithium to afford ortho sulfone dilithiated intermediates, followed by reaction with a TMS electrophile. The corresponding ortho ether 6FPSf derivative was obtained by lithiation of dibrominated 6FPSf at the bromine sites, followed by reaction with a TMS electrophile. The degree of substitution (DS) of the TMS groups was g2.0 and was dependent on the molar ratio of n-butyllithium and electrophile quantity, electrophile reactivity, and reaction conditions. Detailed structural characterization and DS of the modified polymers were obtained by nuclear magnetic resonance spectroscopy. The glass transition temperatures and thermal stabilities were determined by differential scanning calorimetry and thermogravimetric analysis, respectively. Polymer chain d-spacing was investigated using wide-angle X-ray diffraction. Polymer free volume was calculated from the polymer density and specific van der Waals volume. The polymer gas permeability coefficients (P) were measured for He, CO 2,O 2, and N2. Both CO2 and O2 permeabilities of modified 6FPSf increased by 8-9-fold (P(CO2) ) 110 barre...

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Section: Synthesis Of Tm6fpsf-s-tms (Ortho Sulfone)mentioning

confidence: 99%

Preparation and Characterization of Polysulfones Containing Both Hexafluoroisopropylidene and Trimethylsilyl Groups as Gas Separation Membrane Materials

Dai¹,

Guiver²,

Robertson³

et al. 2004

Macromolecules

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“…High gas permeability level of these polymers was caused by the presence of spherical bulky groups (e.g., trimethylsilyl groups or trimethylgermyl groups) and rigid polymer chains which disrupt a dense polymer chain package . Bulky SiMe 3 groups were also introduced into other classes of polymers (polyacetylenes, polystyrenes, polysulfones, poly(phenylene oxide), polyolefins). In all of the mentioned polymers an increase in gas permeability was observed in comparison with non‐silylated polymers.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Gas-Transport Properties of Metathesis Polytricyclononenes Bearing Three Me₃ Si Groups per Monomer Unit

Chapala

Бермешев

Старанникова

et al. 2016

Macromol. Chem. Phys.

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A new metathesis polynorbornene containing three SiMe3 groups per monomer unit directly connected to the norbornene moiety via SiC bonds is synthesized. The ring‐opening metathesis polymerization of sterically hindered 3,3,4‐tris(trimethylsilyl)tricyclononene‐7 is successfully conducted in yields 80–85% in the presence of first generation Grubbs catalyst. The corresponding polymer is obtained with molecular weight Mw up to 5.4 × 105 Da. It is an amorphous glassy (Tg = 200 °C) polymer with high thermal stability. Gas permeability and diffusivity coefficients are studied for a range of gases (He, H2, O2, N2, CO2, CH4). This polymer containing three SiMe3 groups per monomer unit turns out to be more permeable (P(O2) = 125 Barrer) than similar polymers with one or two SiMe3 groups per monomer unit (P(O2) = 30–50 Barrer). Wide angle X‐ray diffraction, positron annihilating lifetime spectroscopy, as well as Brunauer–Emmett–Teller investigations are also performed and discussed.

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“…Trimethylsilylated PPO, prepared by lithiation followed by a reaction with chlorotrimethylsilane, had a fourfold increase in oxygen permeability, with a minimal loss of oxygen/nitrogen selectivity with respect to PPO. 18,19 Modification conditions on PPO can be manipulated to moderately favor lithiation either on the aromatic ring or on the methyl group. Ring-substituted silyl groups had more favorable gas permeation performance than methyl-substituted side groups.…”

Section: Introductionmentioning

confidence: 99%

“…Ring-substituted silyl groups had more favorable gas permeation performance than methyl-substituted side groups. 18 The introduction of a more bulky triphenylsilyl group onto PPO resulted in decreased permeability and permselectivity. 20 PPO substituted with trimethylsilyl groups separated from the aromatic ring with a linear ethynyl spacer increased oxygen permeability by an order of magnitude, but at the expense of permselectivity.…”

Section: Introductionmentioning

confidence: 99%

Modified polysulfones. IV. Synthesis and characterization of polymers with silicon substituents for a comparative study of gas‐transport properties

Guiver¹,

Robertson²,

Rowe³

et al. 2001

J. Polym. Sci. A Polym. Chem.

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Wepreviouslyconductedadetailedstudyofgas-transportandotherpropertiesofaseriesofsiliconderivativesofUdelpolysulfone(PSf)andRadelpolyphenylsulfone;wenowreportthedetailsoftheirpreparationbythereactionoflithiated polymerintermediateswithchlorosilylalkylarylelectrophiles.Ortho-sulfone-substitutedpolymerswithpendanttrimethylsilyl,dimethylphenylsilyl,anddiphenylmethylsilylandothergroupswereobtainedbydirectmetalationfollowedbythereactionofthe dilithiatedintermediatewiththeappropriatesilylelectrophile.Inaddition,thestructuralregularityandgeometryofthedilithiatedsitewasalsoexploitedtointroduce siliconintothemainchainbythereactionofdichlorosilylelectrophiles,leadingtothe formationofanewtricyclicheteroatomring.Ortho-etherPSfderivativeswereobtained fromadibrominatedpolymerviathelithiationofbrominatedpolymerandreaction withasilylelectrophile.Thedegreeofsubstitutionofthesilylgroupswas2.0orless fromdilithiatedpolymersandwasdependentontheelectrophilereactivityandreaction conditions.AdetailedstructuralcharacterizationofthepolymersbyNMRandIRspectroscopyisreportedinadditiontoglass-transitiontemperaturesandthermalstabilities.

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Membranes for gas separation based on silylated polyphenylene oxide

Cited by 26 publications

References 7 publications

Preparation and Characterization of Polysulfones Containing Both Hexafluoroisopropylidene and Trimethylsilyl Groups as Gas Separation Membrane Materials

Preparation and Characterization of Polysulfones Containing Both Hexafluoroisopropylidene and Trimethylsilyl Groups as Gas Separation Membrane Materials

Synthesis and Gas-Transport Properties of Metathesis Polytricyclononenes Bearing Three Me₃ Si Groups per Monomer Unit

Modified polysulfones. IV. Synthesis and characterization of polymers with silicon substituents for a comparative study of gas‐transport properties

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Membranes for gas separation based on silylated polyphenylene oxide

Cited by 26 publications

References 7 publications

Preparation and Characterization of Polysulfones Containing Both Hexafluoroisopropylidene and Trimethylsilyl Groups as Gas Separation Membrane Materials

Preparation and Characterization of Polysulfones Containing Both Hexafluoroisopropylidene and Trimethylsilyl Groups as Gas Separation Membrane Materials

Synthesis and Gas-Transport Properties of Metathesis Polytricyclononenes Bearing Three Me3 Si Groups per Monomer Unit

Modified polysulfones. IV. Synthesis and characterization of polymers with silicon substituents for a comparative study of gas‐transport properties

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Synthesis and Gas-Transport Properties of Metathesis Polytricyclononenes Bearing Three Me₃ Si Groups per Monomer Unit