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Acid-base mixture and ion conductor comprising the same

Inactive Publication Date: 2007-05-10
UBE IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0019] An object of the present invention is to provide an ion conductive acid-base mixture

Problems solved by technology

The fluorine-based acid involves cost and environmental concerns in the production.
Use of the basic component (nitrogen base) in excess lowers the melting point but reduces heat resistance.

Method used

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  • Acid-base mixture and ion conductor comprising the same
  • Acid-base mixture and ion conductor comprising the same
  • Acid-base mixture and ion conductor comprising the same

Examples

Experimental program
Comparison scheme
Effect test

example 1

Mixture of 2-ethyl-4-methylimidazole / 4-methylimidazole and sulfuric acid (2E4MZ / 4MI.H2SO4; molar ratio=1:1:2)

[0066] In 12.7 g of 2E4MZ (from Shikoku Chemicals Corp.) was added dropwise 6 ml of 98% sulfuric acid in a nitrogen atmosphere while stirring. After 2 hour stirring, 20.5 g of 4MI.H2SO4 prepared in Example 8 given later was added thereto, followed by stirring overnight at room temperature. The mixture was dried under reduced pressure at 110° C. for 6 hours to remove water to give 2E4MZ / 4MI.H2SO4 (molar ratio=1:1:2). The acid-base mixture maintained the liquid state for more than 4 months. The results of DSC showed no melting point and a Tg of −54° C. The temperature dependence of the ion conductivity of the acid-base mixture is shown in FIG. 1.

example 2

Mixture of 2-ethyl-4-methylimidazole / 2-ethylimidazole and sulfuric acid (2E4MZ / 2EI.H2SO4; molar ratio=1:1:2)

[0067] In a flask were put 15.7 g of 2E4MZ and 13.7 g of 2EI (from Aldrich), and the 2EI was melted at 100° C. to make a uniform mixture. Into the mixture was added dropwise 15 ml of 98% sulfuric acid in a nitrogen atmosphere while stirring. The mixture was stirred at room temperature overnight, followed by drying under reduced pressure at 110° C. for 6 hours to remove water thereby to give 2E4MZ / 2EI.H2SO4 (molar ratio=1:1:2). The resulting acid-base mixture maintained the liquid state for more than 5 months. The DSC results revealed no melting point and a Tg of −61° C. The temperature dependence of the ion conductivity of the acid-base mixture is shown in FIG. 1. Owing to the mixed base system, the acid-base mixture of Example 2 exhibited improvement in ion conductivity in a low temperature region over the acid-base mixture of Comparative Example 1 hereinafter given.

example 3

Mixture of 2-ethyl-4-methylimidazole / imidazole and sulfuric acid (2E4MZ / Im.H2SO4; molar ratio=1:1:2)

[0068] In 30 ml of ethanol were dissolved 5.17 g of 2E4MZ and 3.20 g of imidazole (from Sigma). The solution was cooled in an ice bath, and 5 ml of 98% sulfuric acid was added thereto dropwise in a nitrogen atmosphere while stirring. The stirring was continued at room temperature overnight, followed by drying under reduced pressure at 60° C. for 1 hour and then at 110° C. for 6 hours to remove ethanol and water to give 2E4MZ / Im.H2SO4 at a molar ratio of 1:1:2. The resulting acid-base mixture was solid at room temperature. In DSC, a sample was maintained at 100° C. to once melt, cooled to −150° C., and again heated from −150° C. up to 100° C. The sample showed only a Tg with no peak of crystallization or melting in both the cooling and the heating thermograms. The Tg was −56° C.

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Abstract

Disclosed is an acid-base mixture composed of a base component and an acid component, wherein at least one of the base component and the acid component contains at least two compounds, and the base component contains at least one compound of formula (1): wherein R1, R2, and R3 each represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, provided that at least one of them is a hydrocarbon group. Also disclosed is an ion conductor comprising an acid-base mixture composed of an acid component and a base component including at least one compound of formula (2): wherein R1, R2, and R3 each represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, provided that R1 and R3 are different.

Description

TECHNICAL FIELD [0001] The present invention relates to a mixture of a base component and an acid component and an ion conductor comprising the same. The ion conductor of the present invention is useful in fuel cells, secondary batteries, electric double layer capacitors, electrolytic capacitors, etc. BACKGROUND ART [0002] Imidazolium salts are well known to be useful as an epoxy resin curing agent. While most of imidazolium salts are solid, JP-A-57-190018 (Patent Document 1) discloses a 2-ethylhexanoate or an acetate of an imidazole compound as an epoxy resin cure accelerator that is liquid at room temperature. Journal of Japan Society of Colour Material, 50 (1), 2-7 (1977) (Non-Patent Document 1) teaches that an imidazole compound salt with an alkylcarboxylic acid or a phosphoric acid is liquid at room temperature and reports epoxy resin curing by the use of the salt. JP-A-48-5900 (Patent Document 2) discloses an epoxy resin composition containing a sulfonate of an imidazole compo...

Claims

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Application Information

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IPC IPC(8): H01B1/12C07D233/58H01G9/02H01G11/56H01M2/16H01M8/02H01M8/10H01M10/0564H01M10/0565H01M10/0566
CPCH01B1/122H01G9/038H01G11/56H01M2/1653H01M8/0291H01M8/1016H01M10/0564H01M10/0565H01M10/0566H01M2300/0025H01M2300/0045Y02E60/13Y02E60/521H01G9/025H01G9/035H01G11/58Y02E60/10Y02E60/50
Inventor HIRANO, TETSUJIHISANO, NOBUHARUKINOUCHI, MASAYUKI
Owner UBE IND LTD
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