Gas separation membranes obtained by partial pyrolysis of polyimides exhibiting polyethylene oxide moieties

Matesanz-Niño, Laura; Aguilar‐Lugo, Carla; Prádanos, Pedro; Hernández, Antonio; Bartolomé, Camino; Campa, José G. de la; Palacio, Laura; González‐Ortega, Alfonso; Galizia, Michele; Álvarez, Celedonio M.; Lozano, Ángel E.

doi:10.1016/j.polymer.2022.124789

Cited by 6 publications

(5 citation statements)

References 56 publications

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“…In recent years, many kinds of PI membranes are developed and applied in gas separation application. Gas permeability and gas selectivity are two vital parameters for characterizing the gas separation property of membranes 4,5 . A good gas separation membrane requires both high gas selectivity and permeability.…”

Section: Introductionmentioning

confidence: 99%

“…Gas permeability and gas selectivity are two vital parameters for characterizing the gas separation property of membranes. 4,5 A good gas separation membrane requires both high gas selectivity and permeability. Nevertheless, the gas-separation membranes usually suffer from an unwanted trade-off relation between selectivity and permeability, which is represented as the Robeson upper-bound.…”

Section: Introductionmentioning

confidence: 99%

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Effect of monomer moieties on the aggregate structure and gas transport properties of polyimides: Insights from experiments and simulations

Tan

Chen

Huang

et al. 2023

J of Applied Polymer Sci

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TFDB‐based PIs (BTDA‐TFDB, PMDA‐TFDB and 6FDA‐TFDB) were prepared by the polymerization of 2,2′‐bis(trifluoromethyl) benzidine (TFDB) with three different dianhydrides, which contained flexible carbonyl bridged unit, rigid‐rod moiety without bridged unit, and bulky CF3 bridged unit in dianhydride moieties, respectively. The influence of dianhydride moieties on the aggregate structure and gas permeation performances of polyimide was systematically investigated in relation to their chain packing and free volumes, using the methods of molecular simulation, positron annihilation measurement and X‐ray diffractogram. Changing the dianhydride from benzophenonetetracarboxylic dianhydride (BTDA) to pyromellitic dianhydride (PMDA) and 4,4′‐(hexafluoroisopropylidene) diphthalic anhydride (6FDA), the gas permeation coefficients of polyimide increased, and the gas permeation selectivity (O2/N2, CO2/N2, H2/N2 and CO2/CH4) decreased. With the introduction of flexible carbonyl bridged unit into dianhydride moiety, the high rotational mobility favored tight chains packing and decreased free volumes, which in turn led to the lowest permeation coefficients of BTDA‐TFDB. The bulky CF3 bridged unit in dianhydride moiety greatly restricted chain packing and increased free volumes, thus resulting in the highest permeation coefficients of 6FDA‐TFDB. From BTDA‐TFDB to PMDA‐TFDB and 6FDA‐TFDB, the permeation selectivity decreased. This was mostly ascribed to the reduction of diffusive selectivity, which was resulted from the increase in free volumes.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Effect of monomer moieties on the aggregate structure and gas transport properties of polyimides: Insights from experiments and simulations

Tan

Chen

Huang

et al. 2023

J of Applied Polymer Sci

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“…After synthesizing iBPDA, it was polymerized with the 2,2-Bis(4-aminophenyl)hexafluoro-propane diamine, 6FpDA, which is very often used in the gas separation field because it produces polymer materials with enhanced gas separation properties [ 39 , 40 , 41 , 42 , 43 , 44 ]. Additionally, a set of isomeric copolyimides obtained by the combination of iBPDA and the 3,3′4,4′- biphenyltetracarboxylic dianhydride, BPDA [ 39 ], were obtained and evaluated, with the idea of modulating the gas separation properties induced by the iBPDA monomer [ 45 , 46 ].…”

Section: Introductionmentioning

confidence: 99%

Isomeric Aromatic Polyimides Containing Biphenyl Moieties for Gas Separation Applications

et al. 2023

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An optimized synthesis of the monomer 2,2′3,3′-biphenyltetracarboxylic dianhydride, iBPDA, was performed to obtain high molecular weight polymers. This monomer has a contorted structure that produces a non-linear shape, hindering the packing of the polymer chain. Aromatic polyimides of high molecular weight were obtained by reaction with the commercial diamine 2,2-bis(4-aminophenyl) hexafluoropropane, 6FpDA, which is a very common monomer in gas separation applications. This diamine has hexafluoroisopropylidine groups which introduce rigidity in the chains, hindering efficient packing. The thermal treatment of the polymers processed as dense membranes had two targets: on the one hand, to achieve the complete elimination of the solvent used, which could remain occluded in the polymeric matrix, and on the other hand to ensure the complete cycloimidization of the polymer. A thermal treatment exceeding the glass transition temperature was performed to ensure the maximum degree of imidization at 350 °C. The good mechanical properties of these materials allow for their use in high-pressure gas purification applications. Moreover, models of the polymers exhibited an Arrhenius-like behavior characteristic of secondary relaxations, normally associated with local motions of the molecular chain. The gas productivity of these membranes was high.

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“…The activation energy is obtained for the whole range of the experimental conversion in one run, and in much less time than the conventional procedures. These two TGA options (HiRes TGA and MTGA) have rarely been used for the investigation of polymers [32][33][34][35][36][37] and, as we are aware, there are no such results reported for Diels-Alder polymers.…”

Section: Introductionmentioning

confidence: 99%

Evidence through Thermal Analysis of Retro Diels-Alder Reaction in Model Networks Based on Anthracene Modified Polyester Resins

Ionita,

Cristea,

Gaina

et al. 2023

Polymers

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The present work is focused on polyester resins obtained from the diglycidyl ether of bisphenol A and anthracene modified 5-maleimidoisophthalic acid. Because the maleimide-anthracene Diels–Alder (DA) adduct is stable at high temperatures, it is considered a good option for high performance polymers. However, the information related to the retroDA reaction for this type of adduct is sometimes incoherent. A detailed thermal study (conventional TGA, HiRes TGA, MTGA, DSC, MDSC) was performed in order to establish whether the rDA reaction can be revealed for this type of anthracene modified polyester resins. The TGA method confirmed the cleavage of the anthracene–maleimide DA adduct, while the DSC demonstrated the presence of anthracene in the system. At high temperatures, unprotected maleimide homopolymerizes and/or reacts with allyl groups according to the –ene reaction. Therefore, the thermal DA reaction is not displayed anymore upon the subsequent cooling, and the glass transition region is registered at a higher temperature range during the second heating. The use of sample-controlled thermal analysis (HiRes TGA) and MTGA improved the TGA result; however, it was not possible to separate the very complex degradation processes that are interconnected.

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Gas separation membranes obtained by partial pyrolysis of polyimides exhibiting polyethylene oxide moieties

Cited by 6 publications

References 56 publications

Effect of monomer moieties on the aggregate structure and gas transport properties of polyimides: Insights from experiments and simulations

Effect of monomer moieties on the aggregate structure and gas transport properties of polyimides: Insights from experiments and simulations

Isomeric Aromatic Polyimides Containing Biphenyl Moieties for Gas Separation Applications

Evidence through Thermal Analysis of Retro Diels-Alder Reaction in Model Networks Based on Anthracene Modified Polyester Resins

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