Thermally rearranged polybenzoxazoles and poly(benzoxazole-co-imide)s from ortho-hydroxyamine monomers for high performance gas separation membranes

Comesaña-Gándara, Bibiana; Hernández, Antonio; Campa, José G. de la; Abajo, Javier de; Lozano, Ángel E.; Lee, Young Moo

doi:10.1016/j.memsci.2015.05.061

Cited by 40 publications

(21 citation statements)

References 32 publications

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“…For the other treatments, a rather linear change was observed. Accordingly, the use of thermal treatment led to lower chain packing densities, which was in agreement with other TR polymers previously reported [30,34,36]. Table 2.…”

Section: Thermal Treatment Of Precursor Polyimidessupporting

confidence: 90%

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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: Thermal Treatment Of Precursor Polyimidessupporting

confidence: 90%

“…According to previous studies [30,34,35] the thermal cyclization reaction is very sensitive to the applied temperature, showing an acceleration in the thermal rearrangement kinetics on increasing temperature.…”

Section: Thermal Treatment Of Precursor Polyimidesmentioning

confidence: 91%

Gas separation membranes made through thermal rearrangement of ortho-methoxypolyimides

et al. 2015

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“…Other groups later reported similar promising results with a variety of hydroxyl-diamine-based 6FDA polyimides [33][34][35][36]. A recent paper by Comesaña-Gándara et al re-investigated the pure-gas permeation properties of 6FDA-DAP and 6FDA-DAR and their polybenzoxazole derivatives formed by thermal rearrangement as well as their nonfunctionalized counterpart polyimide (6FDA-mPDA) [37].…”

Section: Introductionmentioning

confidence: 86%

“…Table 1 shows the data from this work in comparison to previously reported literature data for the same series of polyimides [9,32,37,[45][46][47]. Permeation data of three commercial glassy membrane materials, that is, cellulose triacetate, polysulfone and tetrabromo-polycarbonate are also shown for comparison.…”

Section: Pure-gas Permeation Propertiesmentioning

confidence: 96%

Pure- and mixed-gas permeation properties of highly selective and plasticization resistant hydroxyl-diamine-based 6FDA polyimides for CO2/CH4 separation

Alaslai

Ghanem

Alghunaimi

et al. 2016

Journal of Membrane Science

116

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The effect of hydroxyl functionalization on the m-phenylene diamine moiety of 6FDA dianhydride-based polyimides was investigated for gas separation applications. Pure-gas permeability coefficients of He, H 2 , N 2 , O 2 , CH 4 , and CO 2 were measured at 35 °C and 2 atm.The introduction of hydroxyl groups in the diamine moiety of 6FDA-diaminophenol (DAP) and 6FDA-diamino resorcinol (DAR) polyimides tightened the overall polymer structure due to increased charge transfer complex formation compared to unfunctionalized 6FDA-m-phenylene diamine (mPDA). The BET surface areas based on nitrogen adsorption of 6FDA-DAP (54 m 2 g -1 )and of 6FDA-DAR (45 m 2 g -1 ) were ~18% and 32% lower than that of 6FDA-mPDA (66 m 2 g -1 ).6FDA-mPDA had a pure-gas CO 2 permeability of 14 Barrer and CO 2 /CH 4 selectivity of 70. The hydroxyl-functionalized polyimides 6FDA-DAP and 6FDA-DAR exhibited very high pure-gas CO 2 /CH 4 selectivities of 92 and 94 with moderate CO 2 permeability of 11 and 8 Barrer, respectively. It was demonstrated that hydroxyl-containing polyimide membranes maintained very high CO 2 /CH 4 selectivity (~ 75 at CO 2 partial pressure of 10 atm) due to CO 2 plasticization resistance when tested under high-pressure mixed-gas conditions. Functionalization with hydroxyl groups may thus be a promising strategy towards attaining highly selective polyimides for economical membrane-based natural gas sweetening.

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“…Previous work showed that hydroxyl-functionalized 6FDA-based polyimides exhibit some of the highest CO 2 /CH 4 selectivities reported for all known polymeric materials to date [38][39][40][41][42][43][44]. However, the CO 2 permeability of these polyimides is relatively low (typically less than 10 Barrer).…”

Section: A C C E P T E D Accepted Manuscriptmentioning

confidence: 99%

High-performance intrinsically microporous dihydroxyl-functionalized triptycene-based polyimide for natural gas separation

Alaslai

Ghanem

Alghunaimi

et al. 2016

Polymer

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Please cite this article as: Alaslai N, Ghanem B, Alghunaimi F, Pinnau I, High-performance intrinsically microporous dihydroxyl-functionalized triptycene-based polyimide for natural gas separation, Polymer (2016), doi: 10.1016/j.polymer.2016.03.063. This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. M A N U S C R I P T A C C E P T E D ACCEPTED MANUSCRIPT AbstractA novel polyimide of intrinsic microporosity (PIM-PI) was synthesized from a 9,10-diisopropyltriptycene-based dianhydride (TPDA) and dihydroxyl-functionalized 4,6-diaminoresorcinol (DAR). The unfunctionalized TPDA-m-phenylenediamine (mPDA) polyimide derivative was made as a reference material to evaluate the effect of the OH group in TPDA-DAR on its gas transport properties. Pure-gas permeability coefficients of He, H 2 , N 2 , O 2 , CH 4 , and CO 2 were measured at 35 °C and 2 atm. The BET surface area based on nitrogen adsorption of dihydroxylfunctionalized TPDA-DAR (308 m 2 g -1 ) was 45% lower than that of TPDA-mPDA (565 m 2 g -1 ).TPDA-mPDA had a pure-gas CO 2 permeability of 349 Barrer and CO 2 /CH 4 selectivity of 32.The dihydroxyl-functionalized TPDA-DAR polyimide exhibited enhanced pure-gas CO 2 /CH 4 selectivity of 46 with a moderate decrease in CO 2 permeability to 215 Barrer. The CO 2 permeability of TPDA-DAR was ~30-fold higher than that of a commercial cellulose triacetate membrane coupled with 39% higher pure-gas CO 2 /CH 4 selectivity. The TPDA-based dihydroxyl-containing polyimide showed good plasticization resistance and maintained high mixed-gas selectivity of 38 when tested at a typical CO 2 natural gas wellhead CO 2 partial pressure of 10 atm.

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Thermally rearranged polybenzoxazoles and poly(benzoxazole-co-imide)s from ortho-hydroxyamine monomers for high performance gas separation membranes

Cited by 40 publications

References 32 publications

Gas separation membranes made through thermal rearrangement of ortho-methoxypolyimides

Gas separation membranes made through thermal rearrangement of ortho-methoxypolyimides

Pure- and mixed-gas permeation properties of highly selective and plasticization resistant hydroxyl-diamine-based 6FDA polyimides for CO2/CH4 separation

High-performance intrinsically microporous dihydroxyl-functionalized triptycene-based polyimide for natural gas separation

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