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Norbornene-type polymers having quaternary ammonium functionality

A norbornene, polymer technology, applied in AAEM and, (AAEM) and including the first electrode field, can solve the problem of no anion exchange membrane

Inactive Publication Date: 2012-09-26
SUMITOMO BAKELITE CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are no readily available anion exchange membranes as a commercial standard for electrochemical applications, such as DuPont's PSFA (Perfluorosulfonic Acid) membranes as in the field of cation exchange membranes

Method used

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  • Norbornene-type polymers having quaternary ammonium functionality
  • Norbornene-type polymers having quaternary ammonium functionality
  • Norbornene-type polymers having quaternary ammonium functionality

Examples

Experimental program
Comparison scheme
Effect test

Embodiment M1

[0064] Example M1: Synthesis of endo-5-methyl-exo-5-carboxylic acid-2-norbornene

[0065] Freshly cracked cyclopentadiene (939 g, 14.2 mol) and methacrylic acid (1203 g, 14.2 mol) were added to an appropriately sized vessel containing a magnetic stirrer. The contents were stirred for 24 hours and then left without stirring for 60 hours, during which time a white powder was observed to precipitate out of solution. To facilitate precipitation, the flask was cooled at 10°C for several hours. The precipitate was collected by vacuum filtration and washed with cold pentane (2 L, -10 °C) to remove any unreacted starting material and possible formation of NB(exo-Me)(endo-CO 2 H) By-products. The precipitated white powder (700 g) was recrystallized in hexane (~50 wt%) to give NB(endo-Me)(exo-CO 2 H) Clear crystals (621 g, 29%).

[0066] use 1 HNMR and 13 CNMR characterizes the monomer. Name this NMR signal using the numbering system shown in the figure below.

[0067]

[006...

Embodiment M2

[0069] Example M2——synthesis of internal-5-methyl-external-5-methylhydroxyl-2-norbornene

[0070] NB(inner-Me)(outer-CO 2 H) (174.8 g, 1.15 mmol) and anhydrous toluene (1000 mL) were added to an appropriately sized vessel kept under nitrogen. The vessel was equipped with a magnetic stir bar, thermometer, addition funnel and condenser. Will The premix (500 g, 70 wt% in toluene, 1.73 mol) was added to the addition funnel (brief exposure to air is acceptable if At the same time, keep the temperature of the tank at 5-20°C. After the addition was complete, the contents were heated to 100°C for 6 hours (until thin layer chromatography (TLC) showed complete reaction). The contents were cooled overnight. This solution was slowly added to a beaker containing vigorously stirred 5N HCl (1000 mL). The temperature was maintained at 4 Dry, then filter and remove the solvent under reduced pressure to give NB(inner-Me)(exo-CH 2 OH) (152g, 96%, >95% purity).

[0071] use 1 HNMR and ...

Embodiment M3

[0074] Example M3——synthesis of endo-5-methyl-exo-5-methoxyl-mesylate-2-norbornene

[0075] NB(inner-Me)(outer-CH 2 OH) (74.8 g, 540 mmol) was dissolved in 250 mL of dichloromethane in an appropriately sized vessel. Methanesulfonyl chloride (MsCl) (65.6 g, 0.54 mol) was added. The mixture was then cooled to -12.5°C with a methanol-ice bath. Triethylamine (65.6 g, 650 mmol) was slowly added dropwise while keeping the reaction temperature below -1.0 °C. A large amount of white solid precipitated out. Addition was complete after 30 minutes. The reaction was warmed to 14°C over 40 minutes. GC analysis showed that all starting material was consumed. The mixture was treated with 200 ml of water and the phases were separated. The organic phase was washed with 200 ml of 1N HCl, then brine until the wash gave pH~6. The organic portion was dried over anhydrous magnesium sulfate, filtered and rotary evaporated to afford 100 g (90% yield) of NB(endo-Me)(exo-CH 2 OMs), a light ora...

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Abstract

Embodiments of the present disclosure encompass vinyl addition and ROMP polymers having at least one type of repeating unit that encompasses a comprise N+(CH3)3 OH moiety. Other embodiments in accordance with the disclosure include alkali anion-exchange membranes (AAEMs) made from one of such polymers, anion fuel cells (AFCs) that encompass such AAEMs and components of such AFCs, other than the AAEM, that encompass one of such polymers.

Description

technical field [0001] Embodiments of the present invention generally relate to norbornene-based polymers having quaternary ammonium functional groups, and more particularly to basic anion exchange membranes (AAEMs) useful in the formation of hydroxide ion conducting and comprising first electrodes, AAEMs and Norbornene-based vinyl addition and ROMP polymers for Alkaline Fuel Cells (AFC) with second electrodes where the active layer of each electrode is in contact with the AAEM. Background technique [0002] Alkaline fuel cells (AFC) are one of the most developed technologies and have been used by NASA in the Apollo and Space Shuttle projects since the mid-1960s. The fuel cell on these spacecraft provides electrical energy as well as drinking water to the systems on the spacecraft, and was chosen because it is one of the most efficient in generating electricity, with efficiencies as high as about 70%. [0003] The NASA AFC uses an aqueous electrolyte, specifically a potassi...

Claims

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Application Information

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IPC IPC(8): C08G61/08C08F32/08C08J5/22H01B1/12H01M8/08
CPCC08G61/08C08G2261/3324C08J2385/04C08J5/2256C08F32/08H01M2300/0014C08L65/00Y02E60/50H01M4/8663H01M8/083C08J2365/00C08G2261/143B01D2325/42C08J5/2231C08L45/00B01D71/44B01D71/82C08G2261/418C08J2345/00H01M2300/0082C08G2261/516C08J5/22H01B1/12
Inventor A·贝尔E·埃尔斯K·塞托
Owner SUMITOMO BAKELITE CO LTD
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