Synthesis and properties of highly sulfonated proton conducting polyimides from bis(3-sulfopropoxy)benzidine diaminesElectronic supplementary information (ESI) available: 1H NMR spectra of BSPB diamines and IR spectra of resulting polyimide membranes. See http://www.rsc.org/suppdata/jm/b3/b313276e/

Yin, Yan; Fang, Jianhua; Watari, Tatsuya; Tanaka, Kazuhiro; Kita, Hidetoshi; Okamoto, Ken‐ichi

doi:10.1039/b313276e

Cited by 202 publications

(95 citation statements)

References 25 publications

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“…We also synthesized side-chain-type SPIs bearing pendant sulfoalkoxy groups, such as 2,2 0 -bis(3-sulfopropoxy)benzidine (2,2 0 -BSPB) and 3,3 0 -bis(3-sulfo-propoxy)benzidine (3,3 0 -BSPB), of which the chemical structures are also shown in Figure 1, and investigated the water stability of their membranes. [32][33][34] The data are also summarized in Table I. The side-chaintype SPIs based on 2,2 0 -BSPB and 3,3 0 -BSPB displayed much better water stability than the mainchain-type SPIs.…”

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confidence: 82%

“…The weight loss starting from 250-350 C is attributed to the decomposition of the sulfonic acid groups judging from the evolution of sulfur monoxide and sulfur dioxide. 26,33 The BAPBDS-based SPIs generally displayed decomposition temperature of sulfonic acid groups around 300 C. In the case of 2,2 0 -or 3,3 0 -BSPB-based SPIs, the evolution of propane and propylene were also observed around 250 C, indicating the decomposition of sulfopropoxy side groups. The decomposition temperatures of BSPB-based SPIs were in the range of 232 to 256 C, which was lower than those of the BAPBDS-based SPIs, indicating lower thermal stability of the sulfopropoxy groups.…”

Section: Thermal Properties Of Spi Membranesmentioning

confidence: 99%

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On the Development of Naphthalene-Based Sulfonated Polyimide Membranes for Fuel Cell Applications

Yin

Yamada

Tanaka

et al. 2006

Polym J

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176

109

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ABSTRACT:This article reviews the recent progress made over the past years based on naphthalene-based sulfonated polyimides (SPIs) in terms of proton conductivity, membrane swelling behavior, membrane stability toward water, and fuel cell performance in polymer electrolyte fuel cells (PEFCs) or direct methanol fuel cells (DMFCs). The structure-property relationship of SPI membranes is discussed in details with respect to the chemical structure of various sulfonated diamines and morphology of SPI membranes from the viewpoints of viscosity, mechanical strength and proton conductivity. Ion exchange capacity (IEC), basicity of sulfonated diamine, configuration (para-, meta-, or ortho-orientation) and chemical structure of polymer chain (linear or net-work) show great influence on the water stability and mechanical strength of SPI membrane. The SPIs with a branched/crosslinked structure and derived from highly basic sulfonated diamines display reasonably high water stability of more than 200-300 h in water at 130 C, suggesting high potential as PEMs operating at temperatures up to 100 C. The SPI membranes have fairly high proton conductivity at higher relative humidities and low methanol permeability. The water and methanol crossover through membrane under the fuel cell operation conditions is not controlled by electro-osmosis due to proton transport but by diffusion due to activity difference. This is quite different from the case of perfluorosulfonated membranes such as Nafion and results in the advantageous effects on fuel cell performance. SPI membranes displayed high PEFC performances comparable to those of Nafion 112. In addition, SPI membranes displayed higher performances in DMFC systems with higher methanol concentration (20-50 wt %), which is superior to Nafion and have high potential for DMFC applications at mediate temperatures (40-80 C In the past decades, great interest has been focused on the development of polymer electrolyte fuel cells (PEFCs) and direct methanol fuel cells (DMFCs) as a clean power source of energy for transportation, stationary and portable power applications.1,2 Fuel cells with high performance, high durability and potentially lower cost are greatly required. Polymer electrolyte membrane (PEM) is one of the key components in PEFC and DMFC systems. Perfluorosulfonic acid copolymer membranes, such as DuPont's Nafion membrane, are the state-of-the-art PEMs commercially available due to their high proton conductivity and excellent chemical stability.3,4 However, because of their high cost, low operational temperature below 80 C and large methanol crossover, there has been much interest in alternative PEMs. Many efforts have been done in the development of PEMs based on sulfonated aromatic hydrocarbon polymers. [5][6][7][8][9] The main problem existed in the hydrocarbon PEMs is the membrane stability under fuel cell conditions and low conducting performance at low moisture atmosphere. The balance between ion exchange capacity (IEC), proton conductivity and mechanical stability of a PEM ...

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confidence: 82%

Section: Thermal Properties Of Spi Membranesmentioning

confidence: 99%

On the Development of Naphthalene-Based Sulfonated Polyimide Membranes for Fuel Cell Applications

Yin

Yamada

Tanaka

et al. 2006

Polym J

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176

109

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“…10,11 However, hydrolytic stability is an issue to be addressed. Okamoto and coworkers [12][13][14] reported that introducing propoxy groups between the main chain and sulfonic acid groups improves the hydrolytic stability. We have also investigated the effect of aliphatic groups in both the main and side chains to achieve excellent hydrolytic and oxidative stability.…”

Section: Introductionmentioning

confidence: 99%

“…[1][2][3][4][5] Sulfonated polyimide copolymers have been proposed by several research groups. [6][7][8][9][10][11][12][13][14][15][16][17] The advantage of polyimide ionomers is that a high-molecular-weight polymer with good film-forming capability and high mechanical strength can be easily synthesized by the polycondensation of sulfonated diamine monomers. The hydrophilic/hydrophobic balance or ion-exchange capacity (IEC) can be controlled by changes in the copolymer composition.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and properties of a polyimide containing pendant sulfophenoxypropoxy groups

Miyatake

Yasuda

Hirai

et al. 2006

J. Polym. Sci. A Polym. Chem.

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A novel sulfonated polyimide having pendant sulfophenoxypropoxy groups was synthesized, and its electrolyte properties were investigated for fuel‐cell applications. A diamine monomer was synthesized from 3,3′‐dihydroxybenzidine in four steps, and its polymerization was performed with 1,4,5,8‐naphthalenetetracarboxylic dianhydride in the presence of triethylamine and benzoic acid in m‐cresol. A flexible, ductile, and self‐standing membrane was obtained via casting from an m‐cresol solution. Good thermal, hydrolytic, and oxidative stability was confirmed. The ionomer membrane showed very high proton conductivity of 1.0 S cm−1 at 120 °C and 100% relative humidity, which is higher than that of a Nafion membrane.

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“…[14][15][16][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35] In thin films, aromatic polyimides (PIs) possessing a rigid and planar backbone exhibit a highly ordered lamella structure oriented parallel to the substrate plane with in-plane orientated backbones. 36 Notably, the molecular structure and ch-packing of imide and phenyl groups in PIs significantly vary depending on the aggregation structures, such as crystalline, liquid crystalline-like and amorphous.…”

Section: Introductionmentioning

confidence: 99%

Effect of Casting Solvent on Interfacial Molecular Structure and Proton Transport Characteristics of Sulfonated Polyimide Thin Films

et al. 2017

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Two sulfonated polyimide (SPI) thin films were prepared with water and THF/water mixed solvents, respectively. The SPI thin film prepared with THF/water showed more than 5 times higher proton conductivity than that prepared with water mixed solvent at low relative humidity (RH) and 298 K. In this study, polarized optical microscopy (POM), grazing incidence small angle X-ray scattering (GISAXS), and p-polarized multiple angle incidence resolution spectrometry (pMAIRS) were carried out to investigate liquid crystalline (LC) optical ordered structure, organized structure, and molecular orientation. The molecular ordered parts using LC properties in the SPI thin films exhibited an almost identical structure under the low RH condition. On the other hand, the molecular orientation of the imide C=O groups in the non-ordered parts, which could not be detected by POM and GISAXS, showed different angles. The proton conductivity under low RH conditions is affected by the degree of the molecular orientation in the non-ordered parts of the SPI thin films.

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Synthesis and properties of highly sulfonated proton conducting polyimides from bis(3-sulfopropoxy)benzidine diaminesElectronic supplementary information (ESI) available: 1H NMR spectra of BSPB diamines and IR spectra of resulting polyimide membranes. See http://www.rsc.org/suppdata/jm/b3/b313276e/

Cited by 202 publications

References 25 publications

On the Development of Naphthalene-Based Sulfonated Polyimide Membranes for Fuel Cell Applications

On the Development of Naphthalene-Based Sulfonated Polyimide Membranes for Fuel Cell Applications

Synthesis and properties of a polyimide containing pendant sulfophenoxypropoxy groups

Effect of Casting Solvent on Interfacial Molecular Structure and Proton Transport Characteristics of Sulfonated Polyimide Thin Films

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