Effect of the chemical structure of various diamines on the gas separation of thermally rearranged poly(benzoxazole-co-imide) (TR-PBO-co-I) membranes

Soo, Chye Yang; Jo, Hanik; Lee, Young Moo; Quay, Jeffrey R.; Murphy, Morgan

doi:10.1016/j.memsci.2013.05.056

Cited by 57 publications

(32 citation statements)

References 26 publications

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“…Various TR copolymers were also investigated due to the synergy effects of various TR polymers and glassy polymers [146][147][148][149][150][151]. TR poly(benzoxazole-co-imide) (TR-PBO-co-PI) [146][147][148] and TR poly(benzoxazole-co-pyrrolone) (TR-PBO-co-PPL) [149] were thermally rearranged from copolymer precursors, which were reported from a dianhydride monomer with two different diamine monomers.…”

Section: Tr Co-polymersmentioning

confidence: 99%

“…TR poly(benzoxazole-co-imide) (TR-PBO-co-PI) [146][147][148] and TR poly(benzoxazole-co-pyrrolone) (TR-PBO-co-PPL) [149] were thermally rearranged from copolymer precursors, which were reported from a dianhydride monomer with two different diamine monomers. TR poly(benzoxazole-co-amide) (TR-…”

Section: Tr Co-polymersmentioning

confidence: 99%

“…TR-PBO-co-PI membranes can also improve the mechanical properties of TR polymer membranes [148]. However, TR-PBO-co-PI membranes prepared from 4,4'-oxydiphthalic anhydride (ODPA) and bisAPAF with various diamines [146], or 6FDA, HAB, and two different diamines, i.e., 2,3,5,6-tetramethyl-1,4-phenylenediamine (4MPD) or 9,9′-bis (4-aminophenyl)fluorene (FDA) [147] demonstrated relatively lower CO 2 permeability, listed in Table 1.…”

Section: Page 25 Of 76mentioning

confidence: 99%

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Rigid and microporous polymers for gas separation membranes

Kim

Lee

2015

Progress in Polymer Science

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411

136

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Section: Tr Co-polymersmentioning

confidence: 99%

Section: Tr Co-polymersmentioning

confidence: 99%

Section: Page 25 Of 76mentioning

confidence: 99%

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Rigid and microporous polymers for gas separation membranes

Kim

Lee

2015

Progress in Polymer Science

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411

136

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“…In the decade since TR chemistry was first reported, a vast body of literature has accumulated on a large number of polymers with diverse structures and their gas permeability properties . The insolubility of the final products of TR has hindered the ability to understand the precise polymer structure, thus limiting reliable structure–property–performance correlations.…”

Section: Introductionmentioning

confidence: 99%

Understanding structure and composition of thermally rearranged polymers based on small‐molecule chemistry: a perspective

Murugesan¹,

Sivaram

2019

Polymer International

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We provide a critical perspective of the burgeoning literature on microporous polymers prepared using thermal rearrangement (TR) processes based on the learning derived from analogous chemistry involving small‐molecular‐weight compounds. TR polymers have shown interesting permeability–selectivity relationships in gas separation and, thus, have generated wide interest as potential membrane materials for industrial applications. The intractable nature of the products obtained by TR processes has precluded rigorous structural elucidation of the polymers. Based on small‐molecule chemistry, we conclude that structures are likely to be more complex than generally depicted in the published literature. Interestingly, a simpler chemistry, namely thermal dehydrocyclization (TCD), leads to products identical to those derived from TR, but at significantly lower temperatures. However, TCD chemistry does not involve a skeletal rearrangement of the kind purported in TR during the conversion of imide to oxazole ring resulting in spatially confined heterocyclic ring polymers. Yet, they show similar fractional free‐volume elements as exhibited by TR polymers. This is intriguing and points to a need for more careful examination of the factors responsible for microporosity in such materials. TR chemistry as currently practiced appears limited to only benzoxazole‐type structures. The ability to precisely control and reproducibly produce materials with well‐defined structure and properties will be a key to large‐scale manufacture and industrial applications of such materials. Seen from this perspective, TR processes leave much to be desired and further improvements are clearly warranted. © 2019 Society of Chemical Industry

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“…Recently, the concept of introducing spiro‐centres into a polyimide main chain has attracted much attention . Additionally, an interesting route of using soluble hydroxyl‐substituted polyimides as precursors of insoluble poly(benzoxazole)s has been demonstrated . These new groups of polyimide‐based membrane materials have been shown to have attractive gas transport properties with permeability and selectivity values very often near to or above the Robeson upper bound .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and thermal, mechanical and gas permeation properties of aromatic polyimides containing different linkage groups

Sava¹,

Chişcă²,

Wolińska‐Grabczyk

et al. 2014

Polym. Int.

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Two series of aromatic polyimides containing various linkage groups based on 2,7-bis(4-aminophenoxy)naphthalene or 3,3 ′ -dimethyl-4,4 ′ -diaminodiphenylmethane and different aromatic dianhydrides, namely 4,4 ′ -(4,4 ′ -isopropylidenediphenoxy) bis(phthalic anhydride), 4,4 ′ -(hexafluoroisopropylidene)bis(phthalic anhydride), 3,3 ′ ,4,4 ′ benzophenonetetracarboxylic dianhydride, 9,9-bis[4-(3,4-dicarboxyphenoxy)phenyl]fluorene dianhydride and 4,4 ′ -(4,4 ′ -hexafluoroisopropylidenediphenoxy)bis (phthalic anhydride), were synthesized and compared with regard to their thermal, mechanical and gas permeation properties. All these polymers showed high thermal stability with initial decomposition temperature in the range 475-525 ∘ C and glass transition temperature between 208 and 286 ∘ C. Also, the polymer films presented good mechanical characteristics with tensile strength in the range 60-91 MPa and storage modulus in the range 1700-2375 MPa. The macromolecular chain packing induced by dianhydride and diamine segments was investigated by examining gas permeation through the polymer films. The relationships between chain mobility and interchain distance and the obtained values for gas permeability are discussed.

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Effect of the chemical structure of various diamines on the gas separation of thermally rearranged poly(benzoxazole-co-imide) (TR-PBO-co-I) membranes

Cited by 57 publications

References 26 publications

Rigid and microporous polymers for gas separation membranes

Rigid and microporous polymers for gas separation membranes

Understanding structure and composition of thermally rearranged polymers based on small‐molecule chemistry: a perspective

Synthesis and thermal, mechanical and gas permeation properties of aromatic polyimides containing different linkage groups

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