Novel 6FDA-based polyimides derived from sterically hindered Tröger’s base diamines: Synthesis and gas permeation properties

Ghanem, Bader S.; Alaslai, Nasser Y.; Miao, Xiaohe; Pinnau, Ingo

doi:10.1016/j.polymer.2016.04.068

Cited by 64 publications

(32 citation statements)

References 31 publications

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“…Trçger's base (TB), 2,8-dimethyl-6H,12H-5,11-methanodibenzo[b,f] [1,5]diazocine, is constructed by ab ridged bicyclic amine. [39][40][41][42][43][44][45] Therefore, there is great confidence to expect that aT B-containing polymerw ould be ap romising precursor for CMS membranes. [36][37][38] Recently,t he TB unit was used to prepare TB-PIMs to replacethe spirobisindane unit that was mostly used as parto f the polymer backboneo fP IMs.…”

Section: Introductionmentioning

confidence: 99%

“…Given that the TB unit is more rigid than the spirobisindane unit, these TB-PIMs exhibited high BET surfacea reaso fm ore than 1000 m 3 g À1 and gas-separation performance that surpassed that of most polymer membranes. [39][40][41][42][43][44][45] Therefore, there is great confidence to expect that aT B-containing polymerw ould be ap romising precursor for CMS membranes. In this work, aT B-basedp olyimide (TB-PI) was used as ap olymer precursor to prepareC MS membranes for the first time.…”

Section: Introductionmentioning

confidence: 99%

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Carbon Molecular Sieve Membranes Derived from Tröger's Base‐Based Microporous Polyimide for Gas Separation

et al. 2018

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Carbon molecular sieve (CMS)-based membranes have attracted great attention because of their outstanding gas-separation performance. The polymer precursor is a key point for the preparation of high-performance CMS membranes. In this work, a microporous polyimide precursor containing a Tröger's base unit was used for the first time to prepare CMS membranes. By optimizing the pyrolysis procedure and the soaking temperature, three TB-CMS membranes were obtained. Gas-permeation tests revealed that the comprehensive gas-separation performance of the TB-CMS membranes was greatly enhanced relative to that of most state-of-the-art CMS membranes derived from polyimides reported so far.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Carbon Molecular Sieve Membranes Derived from Tröger's Base‐Based Microporous Polyimide for Gas Separation

et al. 2018

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“…In addition to possessing excellent chemical, mechanical, and thermal stability, polyimides (PIs) and polyetherimides have excellent solubility in many solvents, rendering them suitable for membrane preparation . The high selectivity and low permeability of common PIs are due to their low free volume (10–20 %), as explained by Robeson's upper bound and Freeman's theory .…”

Section: Introductionmentioning

confidence: 80%

“…[1][2][3][4][5] In addition to possessing excellentc hemical, mechanical, and thermals tability, polyimides (PIs) and polyetherimides have excellent solubility in many solvents, rendering them suitable for membrane preparation. [6][7][8][9] Theh igh selectivity and low permeability of common PIs are due to their low free volume( 10-20%), [10] as explained by Robeson's upper bound [11] and Freeman's theory. [12] The design and synthesis of the first polymer of intrinsic microporosity (PIM-1)c ontaining a spirobisindane (SBI) moiety by Budd and McKeown [13] wasa major advance in membrane gas separation.…”

Section: Introductionmentioning

confidence: 99%

A New Pentiptycene‐Based Dianhydride and Its High‐Free‐Volume Polymer for Carbon Dioxide Removal

et al. 2018

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In addition to possessing excellent chemical, mechanical, and thermal stability, polyimides and polyetherimides have excellent solubility in many solvents, which renders them suitable for membrane preparation. Two new monomers [a pentiptycene-based dianhydride (PPDAn) and a pentiptycene imide-containing diamine (PPImDA)] and a pentiptycene-based polyimide [PPImDA-4,4'-hexafluoroisopropylidene diphthalic anhydride (PPImDA-6FDA)] have been synthesized and characterized by FTIR and H NMR spectroscopy, gel-permeation chromatography, mass spectrometry, X-ray photoelectron spectroscopy, thermogravimetric analysis, differential scanning calorimetry, BET surface area, and X-ray diffraction. High-molecular-weight PPImDA-6FDA has remarkable thermal stability and excellent solubility in common organic solvents. It also has an extraordinarily high fractional free volume (0.233) owing to the presence of -C(CF ) - units, the rigid diamine, and the pentiptycene moiety in the polymer structure. It has high CO permeability (812 Barrer) owing to poor chain packing, which is caused by the fact that its rigid groups veil the influence of the ethereal oxygen groups in its backbone. It has the highest CO permeability among all reported pentiptycene-containing polymers (about six times higher than that of the most permeable one) without sacrificing selectivity. The high free volume, good microporosity, high solubility in many solvents, and remarkable thermal stability of PPImDA-6FDA point to the great potential of this polymer for CO removal.

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“…PI-PIMs are generally divided into three categories: 1) PIMs made from reaction of dianhydride with contortion sites, such as SBI, EA and Trip, and halogen-containing aromatic diamines without contortion sites [32][33][34][35][36]; ii) PIMs prepared through dianhydride without contortion sites but diamines with contortions sites, such as SBI, TB, Trip, and pentiptycene [37][38][39][40][41][42][43][44]; iii) PIMs formed via TB polymerization of single di-amino aromatic monomer with imide bonds and contortion sites [45][46][47]. PI-PIMs with contorted sites in both dianhydride and TB-based diamine units were seldom reported [48].…”

Section: Polyimide-based Pimsmentioning

confidence: 99%

Polymers of Intrinsic Microporosity (PIMs) Gas Separation Membranes: A mini Review

Ma¹,

Urban²

2018

Proc. Nat. Res. Soc.

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Polymers of Intrinsic Microporosity (PIMs) are broadly recognized as a potential next generation membrane material for gas separations due to their ultra-permeable characteristics. This mini review aims to provide an overview of these materials and capture its very essence, from chemistry to applications. PIMs-based gas separation membranes are divided into three main categories, i.e., neat PIMs, polymer blend PIMs, and mixed matrix PIMs membranes. This review covers a wide spectrum of PIMs with their gas diffusion mechanisms and separation performance, all of which are examined in detail. Core challenges and opportunities of PIMs membrane technology are reviewed, and this article concludes with future perspectives on PIMs. This mini review establishes a comprehensive understanding of the key technological competence and barriers of PIMs for next-generation gas separations membranes. S ignificant advances in the science and engineering of membrane materials and separation processes have been witnessed in recent decades. Membranes have demonstrated the capability of reducing the enormous amount of energy consumption for gas separations, compared to conventional thermally driven separation processes, like cryogenic distillation [1]. Indeed, membrane separation process is cost-effective and environmentally friendly with small physical footprints. Interests of membrane technology have been growing increasingly in past decades. Key areas that membranes are at play include CO 2 capture, nitrogen generation, hydrogen/helium recovery, natural gas sequestration and biogas purification [2]. Regarded as a new family of membrane materials, Polymers of Intrinsic microporosity (PIMs) have exhibited extremely high gas separation productivity and drawn extensive attention world-widely. The intrinsic microporosity leverages PIMs membranes to far exceed the Robeson upper bound limit of polymeric membranes, which opens an entirely new avenue for gas separations [3]. This review addresses the key developments and advances of PIMs as a super-permeable membrane material for gas separations. Specifically, this paper presents a comprehensive overview of three imperative types of PIMs membranes: those made from, respectively, neat PIMs, polymer blend PIMs, and mixed matrix PIMs.

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Novel 6FDA-based polyimides derived from sterically hindered Tröger’s base diamines: Synthesis and gas permeation properties

Cited by 64 publications

References 31 publications

Carbon Molecular Sieve Membranes Derived from Tröger's Base‐Based Microporous Polyimide for Gas Separation

Carbon Molecular Sieve Membranes Derived from Tröger's Base‐Based Microporous Polyimide for Gas Separation

A New Pentiptycene‐Based Dianhydride and Its High‐Free‐Volume Polymer for Carbon Dioxide Removal

Polymers of Intrinsic Microporosity (PIMs) Gas Separation Membranes: A mini Review

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