JPH038093B2 - - Google Patents
Info
- Publication number
- JPH038093B2 JPH038093B2 JP29366085A JP29366085A JPH038093B2 JP H038093 B2 JPH038093 B2 JP H038093B2 JP 29366085 A JP29366085 A JP 29366085A JP 29366085 A JP29366085 A JP 29366085A JP H038093 B2 JPH038093 B2 JP H038093B2
- Authority
- JP
- Japan
- Prior art keywords
- electrolytic solution
- aprotic solvent
- electrolytic
- carbon atoms
- electrolyte
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- 239000003792 electrolyte Substances 0.000 claims description 11
- 239000000010 aprotic solvent Substances 0.000 claims description 10
- 239000008151 electrolyte solution Substances 0.000 claims description 10
- 239000003990 capacitor Substances 0.000 claims description 9
- -1 hexafluorophosphate salt Chemical class 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- PMDCZENCAXMSOU-UHFFFAOYSA-N N-ethylacetamide Chemical compound CCNC(C)=O PMDCZENCAXMSOU-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- ATHHXGZTWNVVOU-UHFFFAOYSA-N monomethyl-formamide Natural products CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 2
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical group 0.000 claims description 2
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 claims description 2
- KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- ATHHXGZTWNVVOU-VQEHIDDOSA-N n-methylformamide Chemical group CN[13CH]=O ATHHXGZTWNVVOU-VQEHIDDOSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 150000002334 glycols Chemical class 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 description 2
- ZIKIUDJDOOCMAN-UHFFFAOYSA-N 1,3-dioxolan-2-one 1-methylpyrrolidin-2-one Chemical compound C1(OCCO1)=O.CN1C(CCC1)=O ZIKIUDJDOOCMAN-UHFFFAOYSA-N 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- CGWWRMKUJFUTPT-UHFFFAOYSA-N 3-methyl-1h-indole Chemical compound C1=CC=C2C(C)=CNC2=C1.C1=CC=C2C(C)=CNC2=C1 CGWWRMKUJFUTPT-UHFFFAOYSA-N 0.000 description 1
- FLDCSPABIQBYKP-UHFFFAOYSA-N 5-chloro-1,2-dimethylbenzimidazole Chemical compound ClC1=CC=C2N(C)C(C)=NC2=C1 FLDCSPABIQBYKP-UHFFFAOYSA-N 0.000 description 1
- 239000001741 Ammonium adipate Substances 0.000 description 1
- 235000019293 ammonium adipate Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PYHOAVRCHOFKHR-UHFFFAOYSA-N n,n,3,4,5,6-hexamethylphosphinine-2-carboxamide Chemical compound CN(C)C(=O)C1=PC(C)=C(C)C(C)=C1C PYHOAVRCHOFKHR-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
Landscapes
- Electric Double-Layer Capacitors Or The Like (AREA)
- Glass Compositions (AREA)
- Primary Cells (AREA)
Description
〔産業上の利用分野〕
本発明は、非プロトン溶媒中に窒素複素２縮合
環化合物のヘキサフルオロリン酸塩を電解質とし
て含む電解コンデンサ用電解液に関するものであ
る。
〔従来の技術〕
従来、電解コンデンサ用電解液として有機酸又
はその塩・グルコール系ペーストが通常の用途に
対し主流をなして使用されるが、近年の電子機器
の利用範囲の増大からコンデンサ性能の向上改善
の要求が高まり、ペースト中の水の存在が大きな
問題となり、非プロトン溶媒を使用することによ
り有機酸又はその塩・グリコールペーストに代わ
る電解液が注目されるに至つている。
しかし、非プロトン溶媒系電解液の最も大きな
問題は、いかにして高電導度の電解液を得るかに
あり、この目的達成のためには、これら非プロト
ン溶媒に良く溶解し、かつ解離度の高い有機カル
ボン酸若しくはその塩の検索が主体をなしている
が、まだその目的を達し得ず、やむを得ず依然と
してアルコール類、グリコール類などの酸と反応
して水を生成する溶媒、更には水を非プロトン溶
媒に配合して高導電度を得ようとしているが、十
分に高電導化できない、含水量の増加、電解質の
増加で高温での安定性が欠如する欠点を免れない
のが現状である。
それ故、本発明の目的は、非プロトン溶媒を使
用し実質的に非水系の高電導度の電解液を提供す
るにある。
〔発明が解決しようとする問題点〕
本発明者等は、非プロトン溶媒を使用しかつア
ルコール類、グリコール類などの酸と反応して水
を生成する溶媒を使用することなく、実質的に非
水系の電解液でかつ高導電度を与える電解質につ
き鋭意研究を重ねた結果、ヘキサフルオロリン酸
（HPF6）の窒素複素２縮合環化合物塩が非プロ
トン溶媒に溶解性が高く、かつ解離度も高く高電
導度を付与することを見出し本発明に到達したも
のである。
すなわち、本発明に係る電解コンデンサ用電解
液は、非プロトン溶媒中に一般式
（式中ｍ＝０又は１、ｍ＋ｎ＝２又は３、R1＝
炭素原子数１〜３のアルキル置換基が存在又は不
存在、Ｒ＝Ｈ又は炭素数１〜５のアルキル基の１
又は２個により窒素原子は３級又は４級アミンを
構成する窒素複素２縮合環化合物で環中に相互に
共役の２重結合０〜５個含有する化合物）のヘキ
サフルオロリン酸塩を電解質として含むことを特
徴とする。
本発明の対象となる窒素複素２縮合環化合物と
しては、キノリン、２−メチルキノリン（キナル
ジン）、イソキノリン及びこれらの部分水素化物
又は完全水素化物、及び以上の化合物類につきＮ
−アルキル化物類；インドール、３−メチルイン
ドール（スカトール）、イソインドール、プソイ
ドインドール、及びこれらの部分水素化物又は完
全水素化物、及び以上の化合物類につきＮ−アル
キル化物類が挙げられる。
使用される非プロトン溶媒としては、
(1) アミド系溶媒
Ｎ−メチルホルムアミド、Ｎ−ジメチルホル
ムアミド、Ｎ−エチルホルムアミド、Ｎ−ジエ
チルホルムアミド、Ｎ−メチルアセトアミド、
Ｎ−ジメチルアセトアミド、Ｎ−エチルアセト
アミド、Ｎ−ジエチルアセトアミド、ヘキサメ
チルホスホリンアミド。
(2) オキシド系
ジメチルスルホキシド
(3) ニトリル系
アセトニトリル
(4) 環状エステル、アミド系
γ−ブチロラクトン、Ｎ−メチルル−２−ピ
ロリドンエチレンカーボネート、プロピレンカ
ーボネート
などが代表として挙げられるが、これに限定され
るものでない。
本発明に係る電解コンデンサ用電解液は、一般
的に、ヘキサフルオロリン酸の水溶液に所望の窒
素複素２縮合環化合物類の当量を添加反応後減圧
乾燥して無水塩を得ている。
〔実施例〕
以下、本発明に係る電解コンデンサ用電解液の
実施例につき、各種窒素複素２縮合環化合物・ヘ
キサフルオロリン酸塩の各種非プロトン溶媒に対
する13重量％溶液の電導度を第１表に示す。電解
質濃度は１例を示すものであつてこれに限定され
るものでないことは勿論である。尚、比較例とし
て従来の標準的電解液（エチレングリコール78重
量％、水12％、アジピン酸アンモニウム10％）を
示してある。
[Industrial Field of Application] The present invention relates to an electrolytic solution for an electrolytic capacitor, which contains a hexafluorophosphate of a nitrogen hetero-condensed ring compound as an electrolyte in an aprotic solvent. [Prior Art] Traditionally, organic acids or their salts/glucol-based pastes have been mainly used as electrolytes for electrolytic capacitors for normal purposes, but due to the recent increase in the range of use of electronic devices, improvements in capacitor performance have been required. As demands for improvements have increased, the presence of water in pastes has become a major problem, and electrolytic solutions that use aprotic solvents to replace organic acids or their salts/glycol pastes are attracting attention. However, the biggest problem with aprotic solvent-based electrolytes is how to obtain electrolytes with high conductivity. The search for organic carboxylic acids or their salts has been the main focus, but this goal has not yet been achieved, and it is unavoidable that solvents that react with acids such as alcohols and glycols to produce water, and furthermore, that Attempts have been made to obtain high conductivity by blending it into a proton solvent, but the current situation is that it cannot achieve a sufficiently high conductivity, and that it lacks stability at high temperatures due to increased water content and electrolyte. Therefore, it is an object of the present invention to provide a substantially non-aqueous highly conductive electrolyte using an aprotic solvent. [Problems to be Solved by the Invention] The present inventors have solved the problem by using an aprotic solvent and without using a solvent that reacts with acids such as alcohols and glycols to produce water. As a result of extensive research into an aqueous electrolyte that provides high conductivity, we have found that a nitrogen hetero-condensed ring compound salt of hexafluorophosphoric acid (HPF 6 ) has high solubility in aprotic solvents and has a low degree of dissociation. The present invention was achieved by discovering that a high degree of conductivity can be imparted. That is, the electrolytic solution for electrolytic capacitors according to the present invention has the general formula (In the formula, m=0 or 1, m+n=2 or 3, R 1 =
Presence or absence of an alkyl substituent having 1 to 3 carbon atoms, R=H or 1 of an alkyl group having 1 to 5 carbon atoms
Or as an electrolyte, hexafluorophosphate of a compound containing 0 to 5 mutually conjugated double bonds in the ring (a compound containing 0 to 5 mutually conjugated double bonds in the ring), in which two nitrogen atoms constitute a tertiary or quaternary amine. It is characterized by containing. The nitrogen hetero two condensed ring compounds that are the object of the present invention include quinoline, 2-methylquinoline (quinaldine), isoquinoline, their partially or completely hydrides, and the above compounds.
-Alkylated compounds: Indole, 3-methylindole (skatole), isoindole, pseudoindole, partially or fully hydrided products thereof, and N-alkylated compounds of the above compounds. The aprotic solvents used include (1) amide solvents N-methylformamide, N-dimethylformamide, N-ethylformamide, N-diethylformamide, N-methylacetamide,
N-dimethylacetamide, N-ethylacetamide, N-diethylacetamide, hexamethylphosphorinamide. (2) Oxide-based dimethyl sulfoxide (3) Nitrile-based acetonitrile (4) Cyclic ester, amide-based γ-butyrolactone, N-methyl-2-pyrrolidone ethylene carbonate, propylene carbonate, etc. are representative examples, but are not limited to these. It's not something. The electrolytic solution for an electrolytic capacitor according to the present invention is generally prepared by adding an equivalent amount of a desired nitrogen hetero-condensed ring compound to an aqueous solution of hexafluorophosphoric acid, followed by drying under reduced pressure to obtain an anhydrous salt. [Example] Table 1 below shows the conductivity of a 13% by weight solution of various nitrogen hetero-condensed ring compounds/hexafluorophosphates in various aprotic solvents as an example of the electrolytic solution for electrolytic capacitors according to the present invention. Shown below. It goes without saying that the electrolyte concentration is merely an example and is not limited thereto. As a comparative example, a conventional standard electrolytic solution (78% by weight of ethylene glycol, 12% of water, 10% of ammonium adipate) is shown.
【表】【table】
【表】【table】
【表】
次に、実施例１乃至12及び参考例の電解液につ
き25V1μFでのライフ特性を第２表に示す。[Table] Next, Table 2 shows the life characteristics at 25V1 μF for the electrolytes of Examples 1 to 12 and Reference Examples.
本発明に係る電解液によると、従来のグリコー
ル類、水、有機酸塩よりなる高電導度に匹敵若し
くはそれ以上の高電導度を有する非水系電解液が
提供可能とされ、電解コンデンサの設計分野に新
しく広範囲な性能の選択手段を提供できる。
According to the electrolytic solution of the present invention, it is possible to provide a non-aqueous electrolytic solution having a high conductivity comparable to or higher than that of conventional glycols, water, and organic acid salts, and is suitable for use in the design field of electrolytic capacitors. provides a new and wide range of performance options.
Claims (1)
＝炭素原子数１〜３のアルキル置換基が存在又は
不存在、Ｒ＝Ｈ又は炭素原子数１〜５のアルキル
基の１又は２個により窒素原子は３級又は４級ア
ミンを構成する窒素複素２縮合環化合物で環中に
相互に共役の２重結合０〜５個含有する化合物の
ヘキサフルオロリン酸塩を電解質として含む電解
コンデンサ用電解液。 ２ 非プロトン溶媒はＮ−メチルホルムアミド、
Ｎ−ジメチルホルムアミド、Ｎ−エチルホルムア
ミド、Ｎ−ジエチルホルムアミド、Ｎ−メチルア
セトアミド、Ｎ−ジメチルアセトアミド、Ｎ−エ
チルアセトアミド、Ｎ−ジエチルアセトアミド、
γ−ブチロラクトン、Ｎ−メチル−２−ピロリド
ン、エチレンカーボネート、プロピレンカーボネ
ート、ジメチルスルホキシド、アセトニトリル又
はこれらの混合物の群より選択される特許請求の
範囲第１項記載の電解コンデンサ用電解液。[Claims] 1. General formula in an aprotic solvent In the formula, m=0 or 1, m+n=2 or 3, R 1
= Presence or absence of an alkyl substituent having 1 to 3 carbon atoms, R = H or one or two alkyl groups having 1 to 5 carbon atoms, and the nitrogen atom is a nitrogen heterogeneous compound constituting a tertiary or quaternary amine. An electrolytic solution for an electrolytic capacitor containing, as an electrolyte, a hexafluorophosphate salt of a two-fused ring compound containing 0 to 5 mutually conjugated double bonds in the ring. 2 The aprotic solvent is N-methylformamide,
N-dimethylformamide, N-ethylformamide, N-diethylformamide, N-methylacetamide, N-dimethylacetamide, N-ethylacetamide, N-diethylacetamide,
The electrolytic solution for an electrolytic capacitor according to claim 1, which is selected from the group of γ-butyrolactone, N-methyl-2-pyrrolidone, ethylene carbonate, propylene carbonate, dimethyl sulfoxide, acetonitrile, or a mixture thereof.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60293660A JPS62156809A (en) | 1985-12-28 | 1985-12-28 | Electrolyte for electrolytic capacitor |
| US06/917,637 US5112511A (en) | 1985-12-28 | 1986-10-10 | Electrolyte for electrolytic capacitor |
| CA000521752A CA1339592C (en) | 1985-12-28 | 1986-10-29 | An electrolyte for electrolytic capacitor |
| KR1019860009282A KR900005559B1 (en) | 1985-12-28 | 1986-11-04 | Electrolyte for electrolytic capacitor |
| DE8686308729T DE3686869T2 (en) | 1985-12-28 | 1986-11-10 | ELECTROLYT FOR ELECTROLYTIC CAPACITOR. |
| EP86308729A EP0228790B1 (en) | 1985-12-28 | 1986-11-10 | An electrolyte for electrolytic capacitor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60293660A JPS62156809A (en) | 1985-12-28 | 1985-12-28 | Electrolyte for electrolytic capacitor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62156809A JPS62156809A (en) | 1987-07-11 |
| JPH038093B2 true JPH038093B2 (en) | 1991-02-05 |
Family
ID=17797597
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60293660A Granted JPS62156809A (en) | 1985-12-28 | 1985-12-28 | Electrolyte for electrolytic capacitor |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62156809A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4521928B2 (en) * | 2000-04-10 | 2010-08-11 | 三洋化成工業株式会社 | Electrolytic solution for electrolytic capacitor and element for electrolytic capacitor using the same |
-
1985
- 1985-12-28 JP JP60293660A patent/JPS62156809A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62156809A (en) | 1987-07-11 |
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