WO2014156105A1 - アルミニウム電解コンデンサ用電解液、およびそれを用いたアルミニウム電解コンデンサ - Google Patents

アルミニウム電解コンデンサ用電解液、およびそれを用いたアルミニウム電解コンデンサ Download PDF

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WO2014156105A1
WO2014156105A1 PCT/JP2014/001673 JP2014001673W WO2014156105A1 WO 2014156105 A1 WO2014156105 A1 WO 2014156105A1 JP 2014001673 W JP2014001673 W JP 2014001673W WO 2014156105 A1 WO2014156105 A1 WO 2014156105A1
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Prior art keywords
acid
carbon atoms
electrolyte
solution according
compound
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PCT/JP2014/001673
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English (en)
French (fr)
Japanese (ja)
Inventor
晋一 村田
淑未 佐藤
清家　英雄
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三洋化成工業株式会社
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Priority to JP2015508053A priority Critical patent/JP6423786B2/ja
Publication of WO2014156105A1 publication Critical patent/WO2014156105A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C07D233/08—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
    • C07D233/10—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring nitrogen atoms
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
    • H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
    • H01G9/004—Details
    • H01G9/022—Electrolytes; Absorbents
    • H01G9/035—Liquid electrolytes, e.g. impregnating materials

Definitions

  • the present invention relates to an electrolytic solution for an aluminum electrolytic capacitor and an aluminum electrolytic capacitor using the same.
  • alkyl quaternary ammonium electrolytes were used.
  • the alkyl quaternary ammonium electrolyte has a problem in that liquid leakage occurs from a sealing portion deteriorated by alkali.
  • the amidine electrolyte solution disclosed in Patent Document 1 reacts with an alkali in which a compound having an alkyl-substituted amidine group is generated. Therefore, alkaline deterioration of the sealing body is suppressed, and the electrolytic solution does not leak from the sealing portion.
  • it since it has an effect which is not found in alkyl quaternary ammonium electrolytes, it is widely used as an electrolyte for aluminum electrolytic capacitors.
  • the subject of this invention is improving the reliability of an electrolytic capacitor so that electrolyte solution may not leak from a sealing part, even if the surrounding environment further heats up and a high humidity condition, maintaining high initial electrical conductivity.
  • the present invention comprises a solvent (A) and an electrolyte (D) represented by the following general formula (1), and includes a compound (E1) represented by the following general formula (2) and the following general formula (3).
  • R 1 to R 3 represent an alkyl group having 1 to 3 carbon atoms
  • R 4 to R 7 represent an alkyl group having 1 to 3 carbon atoms or a hydrogen atom
  • X ⁇ represents an anion of acid (C).
  • R 8 , R 9 and R 11 to R 14 are an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a hydroxyl group, or a hydrogen atom
  • R 10 and R 15 are an alkyl group having 1 to 3 carbon atoms or a hydrogen atom.
  • R 17 to R 20 are an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a hydroxyl group, or a hydrogen atom.
  • R 16 and R 21 are an alkyl group having 1 to 3 carbon atoms or a hydrogen atom.
  • R 22 , R 23 , R 25 and R 26 represent an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a hydroxyl group or a hydrogen atom.
  • R 24 and R 27 are an alkyl group having 1 to 3 carbon atoms or a hydrogen atom.
  • the electrolytic capacitor using the electrolytic solution of the present invention is a highly reliable capacitor that does not leak the electrolytic solution from the sealed portion even at higher temperature and high humidity in the surrounding environment while maintaining high initial electrical conductivity. Can be.
  • the said compound (E1), the said compound (E2), and the said compound (E3) shall generically be described as a compound (E).
  • OH ⁇ is generated on the cathode side and H + is generated on the anode side due to electrolysis of water contained in the electrolytic solution.
  • H + reacts with compound (E) to become an ammonium cation.
  • the solvent (A) constituting the electrolytic solution of the present invention is preferably a polar solvent, more preferably a polar solvent (A1) having a relative dielectric constant of 5 to 150 at 25 ° C., and (A1 Among these, an aprotic solvent (A11) is more preferable.
  • Solvents (A) include (1) alcohol, (2) ether, (3) amide, (4) oxazolidinone, (5) lactone, (6) nitrile, (7) carbonate, (8) sulfone and (9) Other organic solvents are included.
  • Solvent (A1) includes (1) alcohol, (3) amide, (4) oxazolidinone, (5) lactone, (6) nitrile, (7) carbonate, and (8) sulfone.
  • Examples of the solvent (A11) include (3) amide, (4) oxazolidinone, (5) lactone, (6) nitrile, (7) carbonate, and (8) sulfone.
  • Alcohol Monohydric alcohol methyl alcohol, ethyl alcohol, propyl alcohol, butyl alcohol, diacetone alcohol, benzyl alcohol, amino alcohol, furfuryl alcohol, etc.
  • Dihydric alcohol ethylene glycol, propylene glycol, diethylene glycol, hexylene) Glycol, etc.
  • trihydric alcohol glycerin, etc.
  • tetravalent or higher alcohol hexitol, etc.
  • the protic solvent (A2) refers to the alcohol.
  • Ether monoether ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monophenyl ether, tetrahydrofuran, 3-methyltetrahydrofuran, etc.
  • diether ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol
  • triether diethylene glycol dimethyl ether, diethylene glycol diethyl ether, etc.
  • Amide formamide N-methylformamide, N, N-dimethylformamide, N-ethylformamide, N, N-diethylformamide, etc.
  • acetamide N-methylacetamide, N, N-dimethylacetamide, N-ethylacetamide) N, N-diethylacetamide
  • propionamide N, N-dimethylpropionamide, etc.
  • pyrrolidone N-methylpyrrolidone, N-ethylpyrrolidone, etc.
  • hexamethylphosphorylamide etc.
  • Solvent (A) may be used alone or in combination of two or more. Of these, alcohol, ether, amide, lactone, nitrile, carbonate and sulfone are preferable, ⁇ -butyrolactone and sulfolane are more preferable, and ⁇ -butyrolactone is particularly preferable.
  • the solvent used for the electrolytic solution of the present invention may be a mixture of an aprotic solvent (A11) and a protic solvent (A2).
  • the content of (A2) is 0 to 100% by weight (hereinafter sometimes referred to as wt%) based on the weight of (A11).
  • Preferred examples of (A2) to be mixed include ethylene glycol, propylene glycol, and diethylene glycol.
  • the electrolyte (D) contained in the electrolytic solution of the present invention is a salt composed of an imidazolinium cation (D C ) and an anion (D A ) represented by the general formula (1).
  • R 1 to R 3 are alkyl groups having 1 to 3 carbon atoms
  • R 4 to R 7 are alkyl groups having 1 to 3 carbon atoms or a hydrogen atom. Examples of the alkyl group having 1 to 3 carbon atoms include a methyl group, an ethyl group, an n-propyl group, and an iso-propyl group.
  • imidazolinium cation examples include 1,2,3,4-tetramethylimidazolinium, 1,3,4-trimethyl-2-ethylimidazolinium, and 1,3-dimethyl-2.
  • 1,2,3,4-tetramethylimidazolinium and 1-ethyl-2,3-dimethylimidazolinium are preferable from the viewpoint of electrochemical stability.
  • Examples of the anion (D A ) include an anion of acid (C).
  • Examples of the acid (C) include various organic acids and / or inorganic acids that are usually used in an electrolytic solution.
  • Examples of the organic acid and inorganic acid include the following (1) to (6).
  • Carboxylic acids / C2-C15 divalent to tetravalent polycarboxylic acids aliphatic polycarboxylic acids [saturated polycarboxylic acids (oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, Speric acid, azelaic acid, sebacic acid, etc.), unsaturated polycarboxylic acids (maleic acid, fumaric acid, itaconic acid, etc.)], aromatic polycarboxylic acids [phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid, pyromellitic Acid etc.], S-containing polycarboxylic acid [thiodibropionic acid etc.].
  • saturated polycarboxylic acids oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, Speric acid, azelaic acid, sebacic acid, etc.
  • Oxycarboxylic acid having 2 to 20 carbon atoms aliphatic oxycarboxylic acid [glycolic acid, lactic acid, lactic butyric acid, castor oil fatty acid, etc.], aromatic oxycarboxylic acid [salicylic acid, mandelic acid, etc.].
  • C1-C30 monocarboxylic acid aliphatic monocarboxylic acid [saturated monocarboxylic acid (formic acid, acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, uraryl Acid, myristic acid, stearic acid, behenic acid, etc.), unsaturated monocarboxylic acids (acrylic acid, methacrylic acid, crotonic acid, oleic acid, etc.)], aromatic monocarboxylic acids [benzoic acid, cinnamic acid, naphthoic acid, etc. ].
  • saturated monocarboxylic acid (formic acid, acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, uraryl Acid, myristic acid, ste
  • Phenols and monohydric phenols include phenols and naphthols: Phenol, alkyl (C1-15) phenols (cresol, xylenol, ethylphenol, n- or isopropylphenol, isododecylphenol, cyclohexyl) Phenol), methoxyphenols (eugenol, guaiacol, etc.), ⁇ -naphthol, ⁇ -naphthol, etc.
  • Polyhydric phenol catechol, resorcin, pyrogallol, phloroglucin, bisphenol A, bisphenol F, bisphenol S, etc.
  • Mono- and dialkyl phosphate mono- and dimethyl phosphates having 1 to 15 carbon atoms in the alkyl group mono- and diethyl phosphate esters, mono- and diisopropyl phosphate esters, mono- and dibutyl phosphate esters, mono- and di-- (2-ethylhexyl) phosphate, mono- and diisodecyl phosphate, and the like.
  • a carboxylic acid (C11) having 1 to 15 carbon atoms (3) a monoalkyl phosphate ester having 1 to 15 carbon atoms, and a dialkyl phosphate ester having 2 to 30 carbon atoms and (5) Inorganic acids (C2) are preferred.
  • phthalic acid, maleic acid, mono and diethyl phosphate esters, mono and diisopropyl phosphate esters, mono and dibutyl phosphate esters, phosphoric acid, tetrafluoroboric acid, peroxy Chloric acid, hexafluorophosphoric acid, hexafluoroantimonic acid and hexafluoroarsenic acid are preferred.
  • phthalic acid and maleic acid are preferred.
  • Examples of the electrolyte (D) include the following. 1,2,3,4-tetramethylimidazolinium phthalate anion, 1-ethyl-2,3-dimethylimidazolinium phthalate anion, 1,2,3,4-tetramethylimidazolinium malein Acid anion, 1-ethyl-2,3-dimethylimidazolinium / maleate anion, 1,2,3,4-tetramethylimidazolinium / phosphate anion, 1-ethyl-2,3-dimethylimidazolinium -Phosphate anion, 1,2,3,4-tetramethylimidazolinium-Diethyl phosphate ester anion, 1-ethyl-2,3-dimethylimidazolinium-Diethyl phosphate ester anion, 1, 2, 3,4-tetramethylimidazolinium diisopropyl phosphate anion, 1-ethyl-2,3-dimethylimidazole Um-diis
  • 1,2,3,4-tetramethylimidazolinium phthalate anion 1-ethyl-2,3-dimethylimidazolinium phthalate anion
  • 1,2,3,4-tetramethylimidazolinium malein Acid anion 1-ethyl-2,3-dimethylimidazolinium maleate anion.
  • the electrolytic solution for an aluminum electrolytic capacitor of the present invention contains an electrolyte (D) as a main electrolyte.
  • containing as the main electrolyte means that 50 wt% or more of the electrolyte contained in the electrolytic solution for electrolytic capacitors of the present invention is the electrolyte (D).
  • the electrolytic solution for an aluminum electrolytic capacitor of the present invention may contain an electrolyte (F) in addition to (D).
  • the content of (F) is less than 50 wt% of the electrolyte contained in the electrolytic solution for electrolytic capacitors of the present invention.
  • Examples of the electrolyte (F) include tertiary ammonium salts.
  • Specific examples include triethylamine / phthalate, ethyldimethylamine / phthalate, diethylmethylamine / phthalate, triethylamine / maleate, ethyldimethylamine / maleate, diethylmethylamine / maleate, etc. It is done.
  • the compound (E) constituting the electrolytic solution of the present invention is represented by the compound (E1) represented by the general formula (2), the compound (E2) represented by the general formula (3), and the general formula (4).
  • Specific examples of the compound (E3) include the following.
  • Compound (E) may be used alone or in combination of two or more.
  • Compound (E1) represented by the above general formula (2) 1-ethyl-2,3,4-trimethylimidazolidin-2-ol, 1,2,3,4-tetramethylimidazolidin-2-ol, 1-ethyl-2-methoxy-2,3,4-trimethyl Imidazolidine, 2-methoxy-1,2,3,4-tetramethylimidazolidine and the like.
  • 1-ethyl-3,4-dimethyl-2-methyleneimidazolidine, 1,3,4-trimethyl-2-methyleneimidazolidine, 1,2,3,4-tetramethylimidazolidin-2-ol 2-methoxy-1,2,3,4-tetramethylimidazolidine and 1,2,3-trimethyl-4-methyleneimidazolidine are preferred.
  • the content of the compound (E) [the total content of the compounds (E1), (E2) and (E3)] is 3 wt% or less with respect to the total weight of the solvent (A) and the electrolyte (D). Furthermore, it is preferably 0.001 to 3 wt%, more preferably 0.005 to 2 wt%, still more preferably 0.01 to 1 wt%, and particularly preferably 0.01 to 0.5 wt%. is there. If it exceeds 3 wt%, the electrical conductivity of the electrolytic solution of the present invention will deteriorate.
  • the compound (E) is composed of the compound (E1), the compound (E2) and the compound (E3), and one or two or more of these may be used in combination.
  • the content of the compound (E) is as follows: gas chromatography (instrument: eg GC-17A (manufactured by Shimadzu Corporation), column temperature: 10 ° C./min up to 60-250 ° C., detector FID, column: eg DBWAX (Agilent Quantification can be performed by Technologies, 30 m).
  • water may be added to the electrolytic solution of the present invention.
  • the addition amount is 10 wt% or less based on the weight of the electrolytic solution from the viewpoint of heat resistance.
  • various additives usually used in the electrolyte can be added to the electrolyte of the present invention.
  • the additive include phosphoric acid derivatives (for example, phosphoric acid, phosphoric acid esters, etc.), boric acid derivatives (for example, boric acid, complex compounds of boric acid and polysaccharides [mannit, sorbit, etc.], boric acid and Complex compounds with polyhydric alcohols (ethylene glycol, glycerin, etc.), nitro compounds (eg, o-nitrobenzoic acid, p-nitrobenzoic acid, m-nitrobenzoic acid, o-nitrophenol, p-nitrophenol, etc.)
  • the amount added is 10 wt% or less based on the weight of the electrolyte from the viewpoint of the electrical conductivity of the electrolyte (D) and the solubility in the solvent (A).
  • an electrolytic solution for an aluminum electrolytic capacitor of the present invention a method of adding an electrolyte (D) to a solvent (A) and homogenizing by stirring, then adding a compound (E), stirring and mixing, etc. Is mentioned.
  • Phthalic acid (0.1 mol) is added to the methanol solution of 1-ethyl-2,3-dimethylimidazolinium methyl carbonate salt (0.1 mol) obtained above to give 1-ethyl-2,3-dimethylimidazole.
  • a methanol solution of linium phthalate anion was obtained.
  • the above solution was heated at a reduced pressure of 1.0 kPa or less at 50 ° C. until the distillation of methanol disappeared, the methanol was distilled off, the temperature was raised from 50 ° C.
  • 1-ethyl-2,3-dimethylimidazolinium phthalate anion was recrystallized using methanol and isopropanol to remove impurities (D-3) ⁇ 1-ethyl-2,3- Dimethylimidazolinium phthalate anion ⁇ was obtained.
  • 1,2,3,4-tetramethylimidazolinium diethylphosphate ester A monoanion was obtained.
  • the obtained 1,2,3,4-tetramethylimidazolinium diethylphosphate monoanion was recrystallized using methanol and isopropanol to remove impurities (D-4) ⁇ 1, 2, 3,4-tetramethylimidazolinium diethylphosphate monoanion ⁇ was obtained.
  • the content of the compound (E) is a measurement value measured under the following measurement conditions.
  • the content of the compound (E) is the content of (E) with respect to the total weight of the solvent (A) and the electrolyte (D).
  • a wound aluminum electrolytic capacitor (rated voltage: 6.3 V—capacitance: 220 ⁇ F, size: ⁇ 6.5 mm ⁇ L4.5 mm) was produced.
  • Peroxide-vulcanized butyl rubber was used as the sealing rubber.
  • the produced aluminum electrolytic capacitor was applied with a rated voltage, and the state of the sealing body after 3000 hours was observed.
  • the conditions of temperature and relative humidity were as follows. Condition A; (temperature 105 ° C., relative humidity 85%), condition B; (temperature 130 ° C., relative humidity 85%), condition C; (temperature 140 ° C., relative humidity 85%)
  • the electrical conductivity of the electrolyte before the heat resistance test at 30 ° C. was measured using a conductivity meter CM-40S manufactured by TOA DK Corporation.
  • Examples 1 to 6 and Comparative Example 1 Examples 7 to 12 and Comparative Example 2, Examples 13 to 18 and Comparative Example 3, Examples 19 to 24 and Comparative Example 4, Examples 25 to 30 and Comparative Example 5,
  • Examples 31 to 36 and Comparative Example 6 are compared, and Examples 37 to 42 and Comparative Example 7 are compared, respectively, the liquid leakage property is almost as high as that of the Comparative Example. It turned out that an Example is excellent about both the change rate of conductivity and electrical conductivity.
  • the electrolytic solution of the present invention does not leak from the sealed part even at higher temperatures in the surrounding environment or in humid conditions, and the electrical conductivity is excellent, so the reliability of the electrolytic capacitor Can be increased.
  • the electrolytic solution of the present invention is particularly useful for automotive applications in which the surrounding environment tends to be hot and humid.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Power Engineering (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Electric Double-Layer Capacitors Or The Like (AREA)
PCT/JP2014/001673 2013-03-29 2014-03-24 アルミニウム電解コンデンサ用電解液、およびそれを用いたアルミニウム電解コンデンサ WO2014156105A1 (ja)

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Cited By (1)

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EP2975620A4 (en) * 2013-03-12 2016-12-07 Sanyo Chemical Ind Ltd ELECTROLYTIC SOLUTION FOR AN ALUMINUM ELECTROLYTE CONDENSER AND ALUMINUM ELECTROLYTIC CONDENSER THEREWITH

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JP2004214637A (ja) * 2002-12-18 2004-07-29 Sanyo Chem Ind Ltd 電解コンデンサ用電解液およびそれを用いた電解コンデンサ
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JP4964680B2 (ja) * 2006-06-20 2012-07-04 三洋化成工業株式会社 アルミニウム電解コンデンサ用電解液、およびそれを用いたアルミニウム電解コンデンサ
TW201144324A (en) * 2009-12-17 2011-12-16 Sanyo Chemical Ind Ltd Electrolytic solution for electrolytic condenser and electrolytic condenser using said electrolytic solution
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JP2004214637A (ja) * 2002-12-18 2004-07-29 Sanyo Chem Ind Ltd 電解コンデンサ用電解液およびそれを用いた電解コンデンサ
JP2004253537A (ja) * 2003-02-19 2004-09-09 Matsushita Electric Ind Co Ltd 固体電解コンデンサ
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2975620A4 (en) * 2013-03-12 2016-12-07 Sanyo Chemical Ind Ltd ELECTROLYTIC SOLUTION FOR AN ALUMINUM ELECTROLYTE CONDENSER AND ALUMINUM ELECTROLYTIC CONDENSER THEREWITH
US9793059B2 (en) 2013-03-12 2017-10-17 Sanyo Chemical Industries, Ltd. Electrolytic solution for aluminum electrolytic capacitor and aluminum electrolytic capacitor using the same

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TWI570754B (zh) 2017-02-11
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