Mechanically robust thermally rearranged (TR) polymer membranes with spirobisindane for gas separation

Li, Shenghai; Jo, Hanik; Han, Sang Hoon; Park, Chi Hoon; Kim, Seungju; Budd, Peter M.; Lee, Young Moo

doi:10.1016/j.memsci.2013.01.011

Cited by 173 publications

(85 citation statements)

References 55 publications

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“…Thus, Calle et al [35] obtained TR derived from ether-benzoxazole units that showed mechanical properties rather lower than these obtained in this work for the samples thermally treated at 400 ºC. Li et al [47] developed a class of TR with excellent mechanical properties, but the precursor had a high FFV and the conformational changes associated to the thermal rearrangement were favored and it was found that elongation values were clearly higher than for any TR materials obtained so far.…”

Section: Mechanical Propertiesmentioning

confidence: 57%

Gas separation membranes made through thermal rearrangement of ortho-methoxypolyimides

et al. 2015

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SummaryOrtho-methoxypolyimides were prepared by the classical chemical imidization method and also by azeotropic imidization, using 3,3'-dimethoxybenzidine (DMAB) and hexafluoroisopropylidene diphthalic anhydride (6FDA) as monomers. High molecular weights were achieved by both methods, and the physical properties of the materials were investigated by spectroscopic and thermal analytical techniques. Polymers exhibited excellent thermal properties and film-forming ability, which allowed them to be tested as dense membranes for gas separation after a convenient treatment at high temperature (450 °C) to promote thermal rearrangement (TR). Spectroscopic evidences indicated that the final composition of the TR materials seemed not to correspond to TR-polibenzoxazoles, as it is the case when ortho-hydroxypolyimides are exposed to similar thermal treatments. A detailed study was carried out with the purpose of elucidating the actual mechanism of rearrangement, comparing ortho-

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Section: Mechanical Propertiesmentioning

confidence: 57%

Gas separation membranes made through thermal rearrangement of ortho-methoxypolyimides

et al. 2015

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“…Two distinct regions of mass loss are observed. Such results are common for TR polymers,where the first stage of mass loss is attributed to thermal rearrangement, and the second stage of mass loss is attributed to thermal degradation 2,[5][6][7][8]16,21,24,[54][55][56][57][58][59][60][61]. By comparing these regions, the temperature range and intensity of thermal rearrangement and degradation can be identified.…”

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confidence: 79%

Effect of polymer structure on gas transport properties of selected aromatic polyimides, polyamides and TR polymers

Smith

Hernández

Gleason

et al. 2015

Journal of Membrane Science

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GRAPHICAL ABSTRACT HIGHLIGHTSx Several TR polymer precursors and TR polymers were synthesized.x Thermal rearrangement reactivity was investigated for each structure.x H 2 , CH 4 , N 2 , O 2 , and CO 2 permeabilities track with free volume.x CO 2 hysteresis loops were used to characterize conditioning and plasticization. x APAF-6FDA TR has above-upper bound properties for propylene/propane separation. ABSTRACTThermally rearranged (TR) polymers are formed through a thermally induced solid-state reaction of polyimides or polyamides that contain nucleophilic reactive groups ortho-positioned to their diamine. Naturally, the transport properties of TR polymers are intimately related to the chemical structure and reactivity of their precursors. Herein, we report characterization and transport properties for three poly(hydroxyimide) precursors prepared via thermal imidization in solution and for their corresponding TR polymers.Structural modifications to the polymer backbone can be used to control thermal rearrangement reaction kinetics. In regards to TR polymer formation, samples prepared from diamines with biphenyl functionality reacted more efficiently than those prepared from diamines with hexafluoroisopropylidene-linked aromatic units. However, hexafluoroisopropylidene functional units provided the highest combinations of permeability and selectivity for separations involving H 2 , N 2 , O 2 , CH 4 , and CO 2 .Differences in permeability between samples correlated well with changes in free volume, and 3 poly(hydroxyimide)s showed unusually high selectivities for their given free volume. The effect of synthesis route was also investigated for a specific TR polymer derived from 3,3'-dihydroxy-4,4'-diamino-biphenyl (HAB) and 2,2'-bis-(3,4-dicarboxyphenyl) hexafluoropropane dianhydride (6FDA). Poly(hydroxyimide) precursors prepared via thermal imidization in solution and thermal imidization in the solid-state showed nearly identical permeabilities and selectivities regardless of synthesis route. However, after thermal rearrangement, the TR polymers prepared from polyimides synthesized via solid-state imidization have higher gas permeabilities than their solutionimidized analogs. In addition to light gas permeabilities, plasticization effects were investigated with CO 2 hysteresis loops for all samples, and pure-gas olefin/paraffin permeabilities were determined for a TR polymer derived from 2,2-bis (3-amino-4-hydroxyphenyl)-hexafluoropropane (APAF) and 6FDA. With the exception of HAB-6FDA polyimides, pure-gas CO 2 feed pressures up to approximately 50 bar do not reveal a plasticization pressure point, but conditioning effects are observed for most samples.APAF-6FDA TR polymers have pure-gas permeabilities and selectivities beyond the propylene/propane upper bound.

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“…Subsequent studies of PTMSP membranes have explored ways to improve their performance through strategies such as multilayer composites [11], nanoparticle composites [12], and mixed matrix membranes [13]. More recent research has been focused on the development of highly permeable microporous membrane materials with improved selectivity [14][15][16][17]. -…”

Section: Introductionmentioning

confidence: 99%

Effect of methanol treatment on gas sorption and transport behavior of intrinsically microporous polyimide membranes incorporating Tröger׳s base

Seong

Zhuang

Kim

et al. 2015

Journal of Membrane Science

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Mechanically robust thermally rearranged (TR) polymer membranes with spirobisindane for gas separation

Cited by 173 publications

References 55 publications

Gas separation membranes made through thermal rearrangement of ortho-methoxypolyimides

Gas separation membranes made through thermal rearrangement of ortho-methoxypolyimides

Effect of polymer structure on gas transport properties of selected aromatic polyimides, polyamides and TR polymers

Effect of methanol treatment on gas sorption and transport behavior of intrinsically microporous polyimide membranes incorporating Tröger׳s base

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