Synthesis of Sulfonated Polyimides from Novel Sulfonated Diamines and Their Proton Conductivity and Water Durability.

Watari, Tatsuya; Fang, Jianhua; Tanaka, Kazuhiro; Kita, Hidetoshi; Okamoto, Ken‐ichi; Hirano, Tetsuji

doi:10.1252/kakoronbunshu.29.165

Cited by 6 publications

(4 citation statements)

References 5 publications

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“…Such high water stability should be attributed to the high basicity of o BAPBDS as well as the good solubility stability resulting from the strong interchain interaction due to the sulfonyl group in m BAPPS moiety, as mentioned above. This is just consistent with the results reported in a previous article 15, 17, 21. In addition, from Table 2, it can also be found that o BAPBDS‐based copolyimide membranes showed much better water stability than ODADS‐ and BAPFDS‐based ones with similar IEC.…”

Section: Results and Disscusionsupporting

confidence: 94%

“…The two phenyl rings to which two amino groups are attached are less reactive due to the strong electron withdrawing effect of the protonated amino groups. This direct sulfonation method has been successfully used for preparation of 4,4′‐diaminodiphenyl ether‐2,2′‐disulfonic acid (ODADS), 9,9‐bis(4‐aminophenyl)fluorene‐2,7‐disulfonic acid (BAPFDS) and 4,4′‐bis(4‐aminophenoxy)biphenyl‐3,3′‐disulfonic acid (BAPBDS) 15–17. The elementary analysis of o BAPBDS showed small differences between the calculated and found data due to sorbed water in the sample.…”

Section: Results and Disscusionmentioning

confidence: 99%

“…However, the unusually high cost and other drawbacks such as low conductivity at low humidity, relatively low operating temperature, and high methanol crossover seriously limit their wide applications. To date, a large number of sulfonated hydrocarbon polymers have been developed as proton exchange membrane materials 1–18. The low cost is an attracting advantage for hydrocarbon polymers in comparison with perfluoropolymers, and high proton conductivities that are comparable to that of Nafion have also been achieved with some sulfonated hydrocarbon polymers.…”

Section: Introductionmentioning

confidence: 99%

“…On the other hand, recently we have revealed that the water stability of sulfonated polyimide (SPI) membranes is also strongly affected by their chemical structures besides the IEC, and the SPI membranes with high IEC and good water stability was successfully developed 15–18. In this article, we report on our recent progress on the structure–property studies with an interesting sulfonated diamine monomer, 2,2′‐bis(4‐aminophenoxy)biphenyl‐5,5′‐disulfonic acid ( o BAPBDS).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and properties of novel sulfonated polyimides from 2,2′‐bis(4‐aminophenoxy)biphenyl‐5,5′‐disulfonic acid

Guo

Fang

Tanaka

et al. 2004

J. Polym. Sci. A Polym. Chem.

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Novel sulfonated polyimides (SPIs) were prepared from 1,4,5,8-naphthalenetetracarboxylic dianhydride (NTDA), 2,2Ј-bis(4-aminophenoxy)biphenyl-5,5Јdisulfonic acid (oBAPBDS) with nonlinear configuration, and common nonsulfonated diamines. Water uptake (WU) in liquid and vapor, water stability, and proton conductivity of the resulting SPI membranes were investigated. They were soluble in m-cresol and dimethylsulfoxide, and their WUs in liquid were much larger than those of the SPIs from other sulfonated diamines with linear configuration such as 4,4Ј-bis(4aminophenoxy)biphenyl-3,3Ј-disulfonic acid (BAPBDS). NTDA-oBAPBDS membrane was soluble in water at room temperature, whereas all the oBAPBDS-based copolyimide membranes were insoluble in water and maintained mechanical strength after being soaked in distilled water at 80°C for 40 -1000 h. This much improved water stability was due to the enhanced solubility stability of membrane toward water. The water vapor sorption isotherms were rather similar between the SPIs with the nonlinear and linear configurations of sulfonated diamine moieties. The present SPIs with IECs of 1.8 -2.6 meq/g, including NTDA-BAPBDS, showed reasonably high proton conductivities under the highly humid conditions and roughly fell on the same -WU relation line.

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Section: Results and Disscusionsupporting

confidence: 94%

Section: Results and Disscusionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis and properties of novel sulfonated polyimides from 2,2′‐bis(4‐aminophenoxy)biphenyl‐5,5′‐disulfonic acid

Guo

Fang

Tanaka

et al. 2004

J. Polym. Sci. A Polym. Chem.

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Synthesis and properties of novel sulfonated polyimides containing binaphthyl groups as proton‐exchange membranes for fuel cells

Jin

Wang

et al. 2006

J. Polym. Sci. A Polym. Chem.

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A novel sulfonated diamine monomer, 2,2′‐bis(p‐aminophenoxy)‐1,1′‐binaphthyl‐6,6′‐disulfonic acid (BNDADS), was synthesized. A series of sulfonated polyimide copolymers containing 30–80 mol % BNDADS as a hydrophilic component were prepared. The copolymers showed excellent solubility and good film‐forming capability. Atomic force microscopy phase images clearly showed hydrophilic/hydrophobic microphase separation. The relationship between the proton conductivity and degree of sulfonation was examined. The sulfonated polyimide copolymer with 60 mol % BNDADS showed higher proton conductivity (0.0945–0.161 S/cm) at 20–80 °C in liquid water. The membranes exhibited methanol permeability from 9 × 10−8 to 5 × 10−7 cm2/s at 20 °C, which was much lower than that of Nafion (2 × 10−6cm2/s). The copolymers were thermally stable up to 300 °C. The sulfonated polyimide copolymers with 30–60 mol % BNDADS showed reasonable mechanical strength; for example, the maximum tensile strength at break of the sulfonated polyimide copolymer with 40 mol % BNDADS was 80.6 MPa under high moisture conditions. The optimum concentration of BNDADS was found to be 60 mol % from the viewpoint of proton conductivity, methanol permeability, and membrane stability. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 222–231, 2007

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Synthesis, water stability and proton conductivity of novel sulfonated polyimides from 4,4′-bis(4-aminophenoxy)biphenyl-3,3′-disulfonic acid

Watari

Fang

Tanaka

et al. 2004

Journal of Membrane Science

188

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Synthesis of Sulfonated Polyimides from Novel Sulfonated Diamines and Their Proton Conductivity and Water Durability.

Cited by 6 publications

References 5 publications

Synthesis and properties of novel sulfonated polyimides from 2,2′‐bis(4‐aminophenoxy)biphenyl‐5,5′‐disulfonic acid

Synthesis and properties of novel sulfonated polyimides from 2,2′‐bis(4‐aminophenoxy)biphenyl‐5,5′‐disulfonic acid

Synthesis and properties of novel sulfonated polyimides containing binaphthyl groups as proton‐exchange membranes for fuel cells

Synthesis, water stability and proton conductivity of novel sulfonated polyimides from 4,4′-bis(4-aminophenoxy)biphenyl-3,3′-disulfonic acid

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