Poly(vinylbenzyl sulfonic acid)-grafted poly(ether ether ketone) membranes

Hwang, Mi-Lim; Choi, Jae Boong; Woo, Hyun-Su; Kumar, Vinod; Sohn, Joon-Yong; Shin, Junhwa

doi:10.1016/j.nimb.2013.12.024

Cited by 4 publications

(7 citation statements)

References 36 publications

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“…These observations indicate that the benzylic C−Cl functionalities, previously hypothesized to act as "binding groups", hydrolyze partially to produce benzylic alcohols under typical polymer modification conditions. 30 Notably, after employing CMP-SO 3 H-0.3 to catalyze cellobiose hydrolysis, the C−OH signal intensity further increased, while the C−Cl signal intensity decreased (Figures 2 and S14), consistent with the general instability of benzylic C−Cl groups under catalytic conditions. Another conclusion suggested by these data is that the release of HCl through hydrolysis of benzylic C−Cl bonds 32,33 may be a factor relevant for catalytic hydrolysis reactivity.…”

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confidence: 70%

“…16 The synthesis leading to CMP-SO 3 H-0.3 is adapted from wellknown procedures for modifying polymers. 16,30,31 Furthermore, CMP-SO 3 H-0.3 does not bear any additional functional groups (such as the amine substructure in Pan's catalyst) other than C−Cl and C−SO 3 H moieties. We reasoned that the relative simplicity of CMP-SO 3 H-0.3 would enable a more straightforward elucidation of structure−activity relationships.…”

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confidence: 99%

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Cellulase-Inspired Solid Acids for Cellulose Hydrolysis: Structural Explanations for High Catalytic Activity

Tyufekchiev¹,

Duan

Schmidt‐Rohr

et al. 2018

ACS Catal.

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This work presents a detailed structure–activity analysis of a polymeric solid acid catalyst used in cellulose hydrolysis. In contrast to previous work, our studies show that the high catalytic activity is likely not due to hydrogen bonding between C–Cl moieties at the polymer surface and cellulose fibers. Instead, we report that such C–Cl bonds hydrolyze readily under polymer functionalization conditions to produce C–OH groups on the exterior of the solid acid beads. Furthermore, continued C–Cl to C–OH substitution under cellulose or cellobiose hydrolysis conditions releases HCl from the resin, which contributes to cellulose hydrolysis. Overall, the presented studies stress the need for detailed, quantitative analysis of polymer structures and spatial distribution of functional groups in order to correctly interpret the catalytic results obtained with polymer-based solid acids.

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confidence: 70%

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confidence: 99%

Cellulase-Inspired Solid Acids for Cellulose Hydrolysis: Structural Explanations for High Catalytic Activity

Tyufekchiev¹,

Duan

Schmidt‐Rohr

et al. 2018

ACS Catal.

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“…It is generally known that protons are transported through the cluster network channel in the proton exchange membrane . With an increase in the temperature, the proton conductivity of a proton exchange membrane generally increases owing to the increased mobility of the proton . On the other hand, the formation of ionic cluster network channels is also important to determine the proton conductivity of the membrane and appropriate amount of water is required to form well‐developed ionic cluster network channels.…”

Section: Resultsmentioning

confidence: 99%

Polymer electrolyte membranes prepared by EB‐crosslinking of sulfonated poly(ether ether ketone) with 1,4‐butanediol

Song

Woo

Lee

et al. 2014

J of Applied Polymer Sci

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Crosslinked sulfonated poly(ether ether ketone) (SPEEK) membranes were prepared through the electron beam (EB)‐irradiation crosslinking of SPEEK/1,4‐butanediol under various irradiation conditions and used as a proton exchange membrane (PEM) for fuel cell applications. The crosslinked membranes were characterized by gel fraction, a universal testing machine (UTM), dynamic mechanical analysis (DMA), and small‐angle X‐ray scattering (SAXS). The gel fraction of the crosslinked membranes was used to estimate the degree of crosslinking, and the gel fraction was found to be increased with an increase of the crosslinker content and EB‐absorbed dose. The UTM results indicate that a brittle EB‐crosslinked membrane becomes more flexible with an increase in the crosslinker content. The DMA results show that the EB‐crosslinked membranes have well‐developed ionic aggregation regions and the cluster Tg of membranes decrease with an increase in the 1,4‐butanediol crosslinker content. The SAXS results show that the Bragg and persistence distance of crosslinked membranes increase with an increase in the crosslinker content. The proton conductivities of the EB‐crosslinked membranes were more than 9 × 10−2 S/cm. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015, 132, 41760.

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“…The main function of a PEM-type membrane is to act as a proton conductor, which is related to the presence of sulfonic acid groups into polymers due to their excellent dissociation in the presence of water molecules, which in turn promote the transport of protons within the membrane. The study on the chemical modification of aromatic polymers such as polyether ketones, polyimides, polybenzimidazoles, polyphenylenes, polysulfones, and other copolymers, have been considered as the main alternative to obtaining proton exchange membranes with similar performance than Nafion but at low cost as well as with good chemical and thermal stability [3][4][5][6][7][8]. Studies regarding the insertion of sulfonic groups on aromatic moieties, like polystyrene, have provided insights into how parameters such as reaction time, temperature, and particle size of polystyrene play an important role in sulfonation degree, ion exchange capacity, and morphology [9].…”

Section: Introductionmentioning

confidence: 99%

Indirect sulfonation of telechelic poly(styrene-ethylene-butylene-styrene) via chloromethylation for preparation of sulfonated membranes as proton exchange membranes

Sánchez-Luna¹,

Otmar²,

Kobera³

et al. 2022

Express Polym. Lett.

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The indirect sulfonation, via chloromethylation, of poly(styrene-(ethylene-butylene)-styrene) (polySEBS), under mild conditions, is here reported as an alternative route for the conventional use of chlorosulfonic acid. This indirect sulfonation reaction is an effective route to insert sulfonic groups in the aromatic rings of SEBS to impart a proton exchange capability. The chloromethylated polySEBS was chemically modified by the isothiouronium grouPp, afterward hydrolyzed and oxidized to generate sulfonic acid groups selectively into the aromatic portion (polystyrene) of the polySEBS, to a great extent. The chloromethylated and sulfonated polymeric membranes were characterized by NMR, FT-IR, water uptake, TGA, ion exchange capacity (IEC), and ion conductivity. The obtained results show that as the oxidation time increased in performic acid, the water uptake achieved up to 79.6% due to the conversion of isothiouronium to the sulfonic acid groups into the polymer structure. Furthermore, the sample after 7 hours of oxidation reaction (sSEBS-7H) showed 59% of sulfonation, determined by RMN, and had an IEC value of 1.46 meq/g and also an ion conductivity value of 18.7 mS/cm at RT, which are 46 and 75% higher than those of Nafion 115, a commercial polymer conventionally used for proton exchange membranes (PEM). Thus, the as-prepared sSEBS-7H membrane, via chloromethylation, can be used for PEM since it exhibits good ionic conductivity and structural stability.

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Poly(vinylbenzyl sulfonic acid)-grafted poly(ether ether ketone) membranes

Cited by 4 publications

References 36 publications

Cellulase-Inspired Solid Acids for Cellulose Hydrolysis: Structural Explanations for High Catalytic Activity

Cellulase-Inspired Solid Acids for Cellulose Hydrolysis: Structural Explanations for High Catalytic Activity

Polymer electrolyte membranes prepared by EB‐crosslinking of sulfonated poly(ether ether ketone) with 1,4‐butanediol

Indirect sulfonation of telechelic poly(styrene-ethylene-butylene-styrene) via chloromethylation for preparation of sulfonated membranes as proton exchange membranes

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