Proton-conducting polymers derived from poly(ether-etherketone) and poly(4-phenoxybenzoyl-1,4-phenylene)

Kobayashi, Takeshi; Rikukawa, Masahiro; Sanui, Kohei; Ogata, Naoya

doi:10.1016/s0167-2738(97)00512-2

Cited by 423 publications

(188 citation statements)

References 10 publications

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“…[3][4][5][6] Aromatic polymers with sulfonic acid groups are promising materials for PEMs and polymer-inorganic hybrid membranes because of their outstanding thermal and chemical stability. Sulfonated derivatives of poly(ether sulfone) (SPES), [7][8][9] polyimide (SPI), [10][11][12] polyimidazole, 13 poly(aryl ether), 14,15 polyphenylene, 16,17 and polybenzimidazole 18 are among those being investigated as potential PEMs. However, to further simplify the preparation process and enhance performance of these materials, there are still some challenges, such as stereocontrollable chemical structures including easily controllable degree of sulfonation (DS) and sulfonation sites and well-refined microstructure by grafting, alternating, and blocking polymerization.…”

Section: Introductionmentioning

confidence: 99%

Aromatic Poly(ether ketone)s with Pendant Sulfonic Acid Phenyl Groups Prepared by a Mild Sulfonation Method for Proton Exchange Membranes

et al. 2007

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The sulfonation selectivity of seven poly(ether ether ketone)s (PEEKs) was investigated, and several possessed targeted single-or double-substituted sites per repeated unit on pendant phenyl groups via the postsulfonation approach. The presence of the various pendant groups enabled postsulfonation to occur under mild reaction conditions, in much shorter times than required for the sulfonation of commercial PEEK. A series of poly(ether ketone)s (PEKs) with ion exchange capacity of 2.23-0.84 mequiv/g could be realized by controlling the length of unsulfonated segments of both homopolymers and copolymers. These side-group sulfonation polymers had excellent mechanical properties, good thermal and oxidative stability, and good dimensional stability in hot water. The methanol permeability values of Me-SPEEKK, Me-SPEEKDK, Ph-SPEEKK, and Ph-SPEEKDK at room temperature were in the range 3.31 × 10 -7 -9.55 × 10 -8 cm 2 /s, which is several times lower than that of Nafion 117. Me-SPEEKK and Ph-SPEEKK also exhibited high proton conductivity of 0.15 S/cm at 100°C, which is higher than that of Nafion 117. Transmission electron microscopy analysis was used to observe their microstructure for evidence of microphase separation of ionic and hydrophobic domains. The results showed these side-group-acid materials are possible inexpensive candidate materials for proton exchange membranes in fuel cell applications.

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Section: Introductionmentioning

confidence: 99%

Aromatic Poly(ether ketone)s with Pendant Sulfonic Acid Phenyl Groups Prepared by a Mild Sulfonation Method for Proton Exchange Membranes

et al. 2007

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“…The most widely investigated PEMs include sulfonated derivatives of poly(arylene ether sulfone)s (SPAES), 7,8 poly-(arylene ether ether ketone)s (SPEEK), [9][10][11] poly(arylene sulfide sulfone)s (SPSS), 12,13 poly(arylene ether nitrile)s (SPAEEN), [14][15][16] polyimides (SPI), [17][18][19][20][21] and polyphenylenes (PP). [22][23][24] Many hydrocarbon polymers show sufficiently high conductivities only at high ion-exchange capacities (IEC)s, which causes extensive water uptake above a critical temperature (percolation threshold), or a dramatic loss of mechanical properties due to dimensional swelling that render them unsuitable for practical PEM applications. The dimensional stability and proton conductivity of aromatic ionomers are crucial issues that require improvement through careful structural design.…”

Section: Introductionmentioning

confidence: 99%

Polymer Electrolyte Membranes Derived from New Sulfone Monomers with Pendent Sulfonic Acid Groups

et al. 2010

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New monomers containing two or four pendent phenyl groups were synthesized by bromination of bis(4-fluorophenyl) sulfone, followed by Suzuki coupling with benzeneboronic acid. The resulting monomers were converted to the corresponding sulfonated monomers having two or four pendent sulfonic acid groups, predominately at the p-phenyl position. Aromatic nucleophilic substitution (SNAr) polycondensation using the di- and tetrasulfonated monomers provided sulfonated poly(arylene ether sulfone) copolymers S2-PAES-xx and S4-PAES-xx, respectively, where xx refers to the molar ratio of the sulfonated to non-sulfonated pendent phenyl monomer. Copoly(arylene ether sulfone)s based on the corresponding non-sulfonated monomers were also synthesized for a parallel study on postpolymerization sulfonation of these copolymers. Postsulfonation occurred predominately at the para-pendent phenyl site, and the reactions were complete within a short time (about 30 min), without evidence of chain degradation. Flexible and tough membranes having high mechanical strength were obtained by solution casting of all four series of copolymers. The copolymers with two or four pendent sulfonic acid groups had high proton conductivities in the range of 44−142 mS/cm for S2-PAES-xx and 51−158 mS/cm for S4-PAES-xx at room temperature, respectively. The methanol permeabilities of these copolymers were in the range of 0.8 × 10−8−15.0 × 10−7 cm2/s, which is lower than Nafion (16.7 × 10−7 cm2/s). The S4-PAES-xx membranes displayed better properties (lower water uptake and higher proton conductivities) than the S2-PAES-xx membranes, which can be attributed to the more blocky architecture of the sulfonic acid groups in the S4 membranes. A combination of high proton conductivities, low water uptake, and low methanol permeabilities for some of the obtained copolymers indicated that they are good candidate materials for proton exchange membrane in fuel cell applications.

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“…Among them membranes based on aromatic polyether ether ketone (PEEK) were shown to be very promising for fuel cell application [6][7][8][9], since they possess good mechanical properties, thermal stability, toughness and some conductivity, depending on degree of sulfonation (DS). The approach, adopted in order to improve proton conductivity, in the present work consists of synthesizing composite membranes by incorporation of solid heteropolyacids (HPA) into partially sulfonated PEEK polymer matrices.…”

Section: Introductionmentioning

confidence: 99%

Proton conducting composite membranes from polyether ether ketone and heteropolyacids for fuel cell applications

Zaidi

Mikhailenko

Robertson

et al. 2000

Journal of Membrane Science

849

330

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A series of composite membranes based on sulfonated polyether ether ketone with embedded powdered heteropolycompounds was prepared and their electrochemical and thermal properties were studied. An increase in degree of sulfonation as well as introduction of these fillers resulted in increased T g and enhanced membrane hydrophilicity, bringing about a substantial gain in proton conductivity. The conductivity of the composite membranes exceeded 10 −2 S/cm at room temperature and reached values of about 10 −1 S/cm above 100 • C.

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Proton-conducting polymers derived from poly(ether-etherketone) and poly(4-phenoxybenzoyl-1,4-phenylene)

Cited by 423 publications

References 10 publications

Aromatic Poly(ether ketone)s with Pendant Sulfonic Acid Phenyl Groups Prepared by a Mild Sulfonation Method for Proton Exchange Membranes

Aromatic Poly(ether ketone)s with Pendant Sulfonic Acid Phenyl Groups Prepared by a Mild Sulfonation Method for Proton Exchange Membranes

Polymer Electrolyte Membranes Derived from New Sulfone Monomers with Pendent Sulfonic Acid Groups

Proton conducting composite membranes from polyether ether ketone and heteropolyacids for fuel cell applications

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