Modifications of addition poly(5-vinyl-2-norbornene) and gas-transport properties of the obtained polymers

Wozniak, Alyona I.; Bermesheva, Evgeniya V.; Andreyanov, Fedor A.; Borisov, Ilya L.; Zarezin, Danil P.; Bakhtin, D. S.; Гаврилова, Н.Н.; Ilyasov, Igor R.; Nechaev, Mikhail S.; Asachenko, Andrey F.; Topchiy, Maxim A.; Волков, А. В.; Финкельштейн, Е. Ш.; Ren, Xiang‐Kui; Bermeshev, Maxim V.

doi:10.1016/j.reactfunctpolym.2020.104513

Cited by 38 publications

(15 citation statements)

References 41 publications

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“…Gel-permeation chromatography (GPC) analysis of the polymers was performed on a Waters chromatograph system with a differential refractometer (Chromatopack Microgel-5, chloroform as the eluent, flow rate 1 mL/min) [9,10]. Molecular mass and polydispersity were calculated by standard procedure relative to monodispersed polystyrene standards.…”

Section: Ptmsp Molecular Weightmentioning

confidence: 99%

“…Single gas permeation measurements (N 2 , O 2 , CO 2 , and CH 4 ) were carried out at a temperature of 30.0 ± 0.1 • C and at a feed pressure of 0.1-0.8 bar, using a constant volume/variable pressure experimental setup (GKSS Time-Lag Machine) [9,49]. The measurements were performed for the as-cast PTMSP and PTMSP/HCPS membranes and for the same membranes after their annealing in air at 100 • C for 50, 100, and 300 h. Permeability coefficient P expressed in Barrer (1 Barrer = 10 −10 cm 3 (STP)•cm•cm −2 •s −1 •cmHg −1 ) was estimated by the linear extrapolation of experimental data to zero trans-membrane pressure.…”

Section: Gas Transport Parametersmentioning

confidence: 99%

“…Membrane processes are among the most efficient technologies for the separation of gases and liquids due to low capital costs and small plant sizes compared to other separation methods that require solid or liquid adsorbents or processes such as distillation, which requires an energy-expensive phase transition [1][2][3][4]. Hydrophobic glassy polymers with a large fractional free volume (FFV) or polymers of intrinsic microporosity, such as disubstituted polyacetylenes, polybenzodioxane (PIM-1), and polynorbornenes, are considered promising membrane and sorbing materials for the separation of gases and liquids [5][6][7][8][9][10][11][12][13][14]. The increased interest in these polymers is based on their outstanding properties, in particular, the high fractional free volume, and as a result, high permeability.…”

Section: Introductionmentioning

confidence: 99%

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Hybrid Microporous Polymeric Materials with Outstanding Permeability and Increased Gas Transport Stability: PTMSP Aging Prevention by Sorption of the Polymerization Catalyst on HCPS

et al. 2021

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The influence of hyper-crosslinked polystyrene (HCPS) MacronetTM MN200 on the gas transport properties and aging of the highly permeable glassy polymer poly(1-trimethylsilyl-1-propyne) (PTMSP) was studied and analyzed in detail. The gas transport characteristics of dense PTMSP membranes containing 0–10.0 wt % HCPS were studied. It was shown that the introduction of a small amount of HCPS into the PTMSP matrix led to a 50–60% increase of the permeability coefficients of the material for light gases (N2, O2, CO2) and slowed down the deterioration of polymer transport properties over time. The lowest reduction in gas permeability coefficients (50–57%) was found for PTMSP containing HCPS 5.0 wt % after annealing at 100 °C for 300 h. It was found that HCPS sorbed residues of tantalum-based polymerization catalyst from PTMSP. In order to investigate the influence of catalysts on transport and physical properties of PTMSP, we purified the latter from the polymerization catalyst by addition of 5 wt % HCPS into polymer/chloroform solution. It was shown that sorption on HCPS allowed for almost complete removal of tantalum compounds from PTMSP. The membrane made of PTMSP purified by HCPS demonstrated more stable transport characteristics compared to the membrane made of the initial polymer. HCPS has a complex effect on the aging process of PTMSP. The introduction of HCPS into the polymer matrix not only slowed down the physical aging of PTMSP, but also reduced chemical aging due to removal of active reagents.

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Section: Ptmsp Molecular Weightmentioning

confidence: 99%

Section: Gas Transport Parametersmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Hybrid Microporous Polymeric Materials with Outstanding Permeability and Increased Gas Transport Stability: PTMSP Aging Prevention by Sorption of the Polymerization Catalyst on HCPS

et al. 2021

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“…[85] Similar to polyacetylenes, properties of PNBs can be tuned by the size and structure of side groups. [138,139] Unsubstituted addition PNBs are diffusion-selective showing low FFV ($0.11) and permeabilities. [88,140] Substitution by alkyl side groups provides sorptionselective PNBs (e.g., PDNB, Figure 14) with higher FFV and permeabilities than unsubstituted ones.…”

Section: Polynorbornenesmentioning

confidence: 99%

Hydrocarbon separations by glassy polymer membranes

Iyer

Liu

Zhang

2020

Journal of Polymer Science

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Polymers are unarguably the most broadly used membrane materials for molecular separations and beyond. Motivated by the commercial success of membrane‐based desalination and permanent gas separations, glassy polymer membranes are increasingly being studied for hydrocarbon separations. They represent a class of challenging yet economically impactful bulk separations extensively practiced in the refining and petrochemical industry. This review discusses recent developments in membrane‐based hydrocarbon separations using glassy polymer membranes relying on the sorption‐diffusion mechanism. Hydrocarbon separations by both diffusion‐selective and sorption‐selective glassy polymer membranes are considered. Opinions on the likelihoods of large‐scale implementation are provided for selected hydrocarbon pairs. Finally, a discussion of the challenges and outlook of glassy polymer membrane‐based hydrocarbon separations is presented.

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“…As a result, various addition polymers derived from norbornenes were successfully developed for applications such as adhesives [ 13 ], OLEDs [ 14 , 15 , 16 ], catalyst supports [ 17 , 18 ], membrane materials [ 9 , 19 , 20 ], gas storage materials [ 21 ], and dielectrics [ 22 , 23 , 24 ]. Different norbornene-based membrane materials possessing extremely high gas permeability accompanied by high C 4 H 10 /CH 4 and CO 2 /N 2 selectivities were reported [ 9 , 25 , 26 , 27 , 28 , 29 , 30 ]; in some cases, these polymers possess good long-term stability of their gas transport properties [ 25 , 29 ]. It was found that the most attractive sets of properties can be obtained by the introduction of trimethylsilyl, alkoxysilyl, siloxanyl, and alkyl side groups [ 9 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Gas Transport Properties of Addition Polynorbornene with Perfluorophenyl Side Groups

et al. 2020

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Polynorbornenes represent a fruitful class of polymers for structure–property study. Recently, vinyl-addition polynorbornenes bearing side groups of different natures were observed to exhibit excellent gas permeation ability, along with attractive C4H10/CH4 and CO2/N2 separation selectivities. However, to date, the gas transport properties of fluorinated addition polynorbornenes have not been reported. Herein, we synthesized addition polynorbornene with fluoroorganic substituents and executed a study on the gas transport properties of the polymer for the first time. A norbornene-type monomer with a C6F5 group, 3-pentafluorophenyl-exo-tricyclononene-7, was successfully involved in addition polymerization, resulting in soluble, high-molecular-weight products obtained in good or high yields. By varying the monomer concentration and monomer/catalyst ratio, it was possible to reach Mw values of (2.93–4.35) × 105. The molecular structure was confirmed by NMR and FTIR analysis. The contact angle with distilled water revealed the hydrophobic nature of the synthesized polymer as expected due to the presence of fluoroorganic side groups. A study of the permeability of various gases (He, H2, O2, N2, CO2, and CH4) through the prepared polymer disclosed a synergetic effect, which was achieved by the presence of both bulky perfluorinated side groups and rigid saturated main chains. Addition poly(3-pentafluorophenyl-exo-tricyclononene-7) was more permeable than its metathesis analogue by a factor of 7–21, or the similar polymer with flexible main chains, poly(pentafluorostyrene), in relation to the gases tested. Therefore, this investigation opens the door to fluorinated addition polynorbornenes as new potential polymeric materials for membrane gas separation.

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Modifications of addition poly(5-vinyl-2-norbornene) and gas-transport properties of the obtained polymers

Cited by 38 publications

References 41 publications

Hybrid Microporous Polymeric Materials with Outstanding Permeability and Increased Gas Transport Stability: PTMSP Aging Prevention by Sorption of the Polymerization Catalyst on HCPS

Hybrid Microporous Polymeric Materials with Outstanding Permeability and Increased Gas Transport Stability: PTMSP Aging Prevention by Sorption of the Polymerization Catalyst on HCPS

Hydrocarbon separations by glassy polymer membranes

Synthesis and Gas Transport Properties of Addition Polynorbornene with Perfluorophenyl Side Groups

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