JP3131905B2 - Flame retardant for electrolyte for lithium battery - Google Patents
Flame retardant for electrolyte for lithium batteryInfo
- Publication number
- JP3131905B2 JP3131905B2 JP02311271A JP31127190A JP3131905B2 JP 3131905 B2 JP3131905 B2 JP 3131905B2 JP 02311271 A JP02311271 A JP 02311271A JP 31127190 A JP31127190 A JP 31127190A JP 3131905 B2 JP3131905 B2 JP 3131905B2
- Authority
- JP
- Japan
- Prior art keywords
- electrolyte
- phosphate
- lithium battery
- flame retardant
- solvent
- 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 - Fee Related
Links
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Landscapes
- Secondary Cells (AREA)
- Primary Cells (AREA)
Description
【発明の詳細な説明】 ［産業上の利用分野］ 本発明は、リチウム電池に用いる電解液に関する。本
発明によれば、安全性の高いリチウム電池を得ることが
できる。Description: TECHNICAL FIELD The present invention relates to an electrolytic solution used for a lithium battery. According to the present invention, a highly safe lithium battery can be obtained.
［従来の技術］ 従来、リチウム電池には、電解液として、プロピレン
カーボネート、γ−ブチロラクトン、1,2−ジメトキシ
エタンなどの単独又はこれらの混合溶媒に、過塩素酸リ
チウム、ホウフッ化リチウム、リンフッ化リチウム、ト
リフルオロメタンスルホン酸リチウムなどの溶質を溶解
したものが使用されている。[Prior Art] Conventionally, lithium batteries have been used alone or in a mixed solvent of propylene carbonate, γ-butyrolactone, 1,2-dimethoxyethane, or the like as an electrolytic solution in the form of lithium perchlorate, lithium borofluoride, or phosphorus fluoride. A solution in which a solute such as lithium or lithium trifluoromethanesulfonate is dissolved is used.
一方、難燃化剤として、酸化アンチモンやホウ酸亜鉛
などの無機化合物ならびに分子中にリン又はハロゲンを
含有する有機化合物などが知られている。しかし、電解
液に難燃性を付与する際には、電気伝導率、使用電位範
囲、使用温度範囲、電極材料との間の適合性など、電解
液としての基本的性能を妨げないことが必要となる。た
とえば、上述の無機化合物やハロゲン化物は、ほとんど
の場合固体物質であり、有機溶媒に不溶で、電気伝導率
を低下させる。また一般に有機溶媒として使用されてい
る塩化メチレンなどのハロゲン化炭化水素を、誘電率が
低く、電気伝導率を低下させるので、電解液に使用する
溶媒としては使用できない。On the other hand, as flame retardants, inorganic compounds such as antimony oxide and zinc borate, and organic compounds containing phosphorus or halogen in the molecule are known. However, when imparting flame retardancy to the electrolyte, it is necessary that the basic performance of the electrolyte such as electrical conductivity, operating potential range, operating temperature range, compatibility with electrode materials, etc. should not be impaired. Becomes For example, the above-mentioned inorganic compounds and halides are mostly solid substances, are insoluble in organic solvents, and lower the electric conductivity. Further, halogenated hydrocarbons such as methylene chloride, which are generally used as an organic solvent, have a low dielectric constant and lower electric conductivity, and therefore cannot be used as a solvent for an electrolytic solution.
［発明が解決しようとする問題点］ 上記のリチウム電池は、非常に燃え易い溶媒を使用し
ているため、内部短絡等によって電池が破壊した際に、
火花が電解液に引火して、機器を損傷したり、火災に至
ることがあり得る。特に、近年、携帯用機器にリチウム
電池が搭載されるようになり、リチウム電池の安全性は
ますます重要性を増し、社会問題と成りつつある。[Problems to be Solved by the Invention] Since the above lithium battery uses a very flammable solvent, when the battery is broken due to an internal short circuit or the like,
Sparks can ignite the electrolyte, causing equipment damage or fire. In particular, in recent years, lithium batteries have been mounted on portable devices, and the safety of lithium batteries has become more and more important, and is becoming a social problem.
［課題を解決するための手段］ 本発明者は、低級リン酸エステルを電解液の溶媒ある
いは助溶媒として利用することにより、電池としての特
性を維持しつつ、難燃性を示す電解液を得ることに成功
し、本発明を完成した。Means for Solving the Problems The present inventor obtains an electrolyte solution exhibiting flame retardancy while maintaining the characteristics as a battery by using a lower phosphate ester as a solvent or a cosolvent for the electrolyte solution. The present invention was completed successfully.
すなわち、本発明は、一般式（II）： で示される単環式ホスフェート及び一般式（III）： で示される二環式ホスフェート（式中、R4は、炭素数１
〜４の直鎖状又は分枝状のアルキル基を表わし；−
（Ｃ）−は、直鎖状又は分枝状の炭化水素基における、
１個の炭素原子を有する単位であり、ｋ、ｌ、ｍ、ｎ
は、該炭化水素基の炭素数を示し、ｋ＝２〜８、ｌ、
ｍ、ｎ＝０〜12の整数である。） からなる群より選ばれるリン酸エステルである、リチウ
ム電池用電解液の難燃化剤に関し；また電解液の溶媒中
に、該難燃化剤を15重量％以上含有させ、又は電解液中
に、難燃化剤を含有させてそれ以外に溶媒を含有させな
い、リチウム電池用電解液を難燃化する方法に関する。That is, the present invention provides a compound represented by the general formula (II): A monocyclic phosphate represented by the general formula (III): A bicyclic phosphate represented by the formula (wherein R 4 is a group having 1 carbon atom)
Represents a linear or branched alkyl group of 1 to 4,
(C)-is a linear or branched hydrocarbon group,
A unit having one carbon atom, k, l, m, n
Represents the number of carbon atoms of the hydrocarbon group, and k = 2 to 8, l,
m and n are integers of 0 to 12. A) a flame retardant of an electrolyte for a lithium battery, which is a phosphate ester selected from the group consisting of; In addition, the present invention relates to a method for making a lithium battery electrolyte solution flame-retardant, which contains a flame retardant and no other solvent.
リチウム塩を有機溶媒に溶解したリチウム電池用電解
液において、リン酸エステルを含んだ溶媒を使用するこ
とにより、難燃性電解液が得られる。すなわち本発明
は、リチウム電池用の電解液を難燃性にする難燃化剤及
び難燃化方法を提供するものである。A flame-retardant electrolytic solution can be obtained by using a solvent containing a phosphate ester in an electrolytic solution for a lithium battery in which a lithium salt is dissolved in an organic solvent. That is, the present invention provides a flame retardant and a flame retardation method for making an electrolyte for a lithium battery flame retardant.
使用するリン酸エステルは、下記の一般式で表わされ
るトリアルキルホスフェート（Ｉ）、アルキル基どうし
が互いに結合した単環式ホスフェート（II）及び二環式
ホスフェート（III）である。The phosphoric acid ester used is a trialkyl phosphate (I) represented by the following general formula, a monocyclic phosphate (II) in which alkyl groups are bonded to each other, and a bicyclic phosphate (III).
（式中、R1〜R4は炭素数１〜４の直鎖状又は分枝状のア
ルキル基で、R1〜R3は互いに異なっていてもよい。−
（Ｃ）−は、直鎖状又は分枝状の炭化水素基における、
１個の炭素原子を有する単位であり、ｋ、ｌ、ｍ、ｎ
は、該炭化水素基の炭素数を示し、ｋ＝２〜８、ｌ、
ｍ、ｎ＝０〜12の整数である。） 具体例としては、一般式（Ｉ）で表わされるリン酸エ
ステルとしてトリメチルホスフェート、ジメチルエチル
ホスフェート、メチルエチルプロピルホスフェート、メ
チルジエチルホスフェート、トリエチルホスフェート、
トリプロピルホスフェート、トリブチルホスフェート；
一般式（II）で表わされるものとして、メチルエチレン
ホスフェート、メチルトリメチレンホスフェート；なら
びに一般式（III）で表わされるものとして、 及びトリメチロールエタンホスフェート等を例示するこ
とができる。これらの中でも、分子量の小さいリン酸エ
ステルの方が、溶質を良く溶かし、電気伝導度が高いの
で好ましい。特にトリメチルホスフェートは、電気伝導
度が最も高く、また、分子構造中のリン含有量が最も高
いために、難燃性が大きくて引火しないので、最も好ま
しい。 (In the formula, R 1 to R 4 are linear or branched alkyl groups having 1 to 4 carbon atoms, and R 1 to R 3 may be different from each other.
(C)-is a linear or branched hydrocarbon group,
A unit having one carbon atom, k, l, m, n
Represents the number of carbon atoms of the hydrocarbon group, and k = 2 to 8, l,
m and n are integers of 0 to 12. As specific examples, trimethyl phosphate, dimethyl ethyl phosphate, methyl ethyl propyl phosphate, methyl diethyl phosphate, triethyl phosphate, as the phosphoric ester represented by the general formula (I),
Tripropyl phosphate, tributyl phosphate;
As represented by the general formula (II), methyl ethylene phosphate and methyl trimethylene phosphate; and as represented by the general formula (III): And trimethylolethane phosphate. Among these, phosphate esters having a small molecular weight are preferable because they dissolve solutes well and have high electric conductivity. In particular, trimethyl phosphate is most preferable because it has the highest electric conductivity and the highest phosphorus content in the molecular structure, and therefore has high flame retardancy and does not catch fire.
本発明で用いるリン酸エステルは、一般式（II）又は
（III）で示される、単環式又は二環式ホスフェートで
ある。The phosphate ester used in the present invention is a monocyclic or bicyclic phosphate represented by the general formula (II) or (III).
上記のリン酸エステルの電解液に占める割合は、リチ
ウム電池の要求性能によって異なるが、溶媒を全量、リ
ン酸エステルにした場合に最も難燃性の高いリチウム電
池が得られる。従来の電解液に助溶媒として添加して難
燃性を向上させるためには、15重量％以上、好ましくは
30重量％以上使用すると、良好な難燃性が得られる。The proportion of the phosphate ester in the electrolyte varies depending on the required performance of the lithium battery. However, when the total amount of the solvent is phosphate ester, a lithium battery having the highest flame retardancy can be obtained. In order to improve the flame retardancy by adding it as a co-solvent to a conventional electrolyte, it is required to be 15% by weight or more, preferably
When used in an amount of 30% by weight or more, good flame retardancy is obtained.
上記のリン酸エステルを混合する溶媒としては、エチ
レンカーボネート、プロピレンカーボネート、ブチレン
カーボネート等のカーボネート溶媒；γ−ブチロラクト
ン等のラクトン溶媒;1,2−ジメトキシエタン、1,3−ジ
オキソラン、テトラヒドロフラン等のエーテル溶媒を例
示することができる。As the solvent for mixing the above phosphate ester, carbonate solvents such as ethylene carbonate, propylene carbonate and butylene carbonate; lactone solvents such as γ-butyrolactone; ethers such as 1,2-dimethoxyethane, 1,3-dioxolan, and tetrahydrofuran Solvents can be exemplified.
また、溶質としては、LiClO4、LiBF4、LiPF6、LiAs
F6、LiCF3SO3、LiAlCl4等を例示することができる。The solutes include LiClO 4 , LiBF 4 , LiPF 6 , LiAs
Examples include F 6 , LiCF 3 SO 3 , and LiAlCl 4 .
［実施例］ 以下に実験例、参考例及び比較例を挙げて、本発明を
さらに具体的に説明する。EXAMPLES Hereinafter, the present invention will be described more specifically with reference to Experimental Examples, Reference Examples, and Comparative Examples.
電解液の難燃性の評価法として、電解液を含浸した紙
の燃焼速度を採用した。引火点は、ペンスキー・マルテ
ンス密閉式試験器によって測定した。As a method for evaluating the flame retardancy of the electrolytic solution, the burning rate of paper impregnated with the electrolytic solution was employed. The flash point was measured with a Pensky-Martens closed tester.
実験例１ トリメチルホスフェートにLiBF4を１モル濃度溶解し
た電解液（25℃における電気伝導度5.6mS/cm）に、幅15
mm、長さ320mm、厚さ40μｍ、密度0.6g/cm3のマニラ紙
を１分間浸し、３分間、垂直に吊下げて余分な電解液を
除いた。このようにして電解液を含浸させたマニラ紙
を、25mm間隔で支持針を有するサンプル保持台に水平に
固定して、その一端にマッチで着火したところ、燃焼距
離10mm以内でただちに消火した。EXPERIMENTAL EXAMPLE 1 A width of 15% was added to an electrolyte (electric conductivity of 5.6 mS / cm at 25 ° C.) in which LiBF 4 was dissolved at a molar concentration of 1 in trimethyl phosphate.
Manila paper of mm, length of 320 mm, thickness of 40 μm and density of 0.6 g / cm 3 was immersed for 1 minute and suspended vertically for 3 minutes to remove excess electrolyte. The manila paper impregnated with the electrolyte was fixed horizontally on a sample holder having supporting needles at intervals of 25 mm, and one end of the paper was ignited with a match. The fire was immediately extinguished within a burning distance of 10 mm.
比較例１ γ−ブチロラクトンにLiBF4を１モル濃度溶解した電
解液（25℃における電気伝導度7.8mS/cm）に、実験例１
と同じ条件でマニラ紙を浸し、同様の着火試験によっ
て、300mm燃焼する時間より燃焼速度を求めたところ、
燃焼速度は10mm/sであった。Comparative Example 1 Experimental Example 1 was prepared in an electrolytic solution in which 1 mol of LiBF 4 was dissolved in γ-butyrolactone (electric conductivity at 25 ° C. 7.8 mS / cm).
The manila paper was immersed under the same conditions as above, and the burning speed was determined from the burning time of 300 mm by the same ignition test.
The burning rate was 10 mm / s.
実験例２、３ 実験例１において、溶媒をトリエチルホスフェート
（実験例２）、γ−ブチロラクトンとトリメチルホスフ
ェートとの重量比1:1の混合溶媒（実験例３）に変え
て、同様の着火試験を行った。いずれも高い難燃性を示
した。Experimental Examples 2 and 3 The same ignition test was conducted as in Experimental Example 1, except that the solvent was changed to triethyl phosphate (Experimental Example 2), and a mixed solvent of γ-butyrolactone and trimethyl phosphate at a weight ratio of 1: 1 (Experimental Example 3). went. All exhibited high flame retardancy.
比較例２ 比較例１において、溶媒をプロピレンカーボネートに
変えて、同様の試験を行ったところ、易燃性であった。Comparative Example 2 The same test was performed as in Comparative Example 1 except that the solvent was changed to propylene carbonate, and the result was flammability.
参考例１〜７ 参考例１として何も含浸しないマニラ紙、参考例２〜
７として溶媒のみを含浸したマニラ紙について、同様の
着火試験を行った。Reference Examples 1 to 7 As Reference Example 1, a non-impregnated manila paper, Reference Examples 2 to
The same ignition test was performed on Manila paper impregnated with only the solvent as No. 7.
これらの着火試験の結果；ならびに各実験例、参考例
（参考例１を除く）、比較例試料の引火点；及び各実験
例、参考例、比較例試料の電気伝導度をまとめて表１に
示す。Table 1 summarizes the results of these ignition tests; the flash point of each experimental example, reference example (excluding reference example 1) and the comparative example sample; and the electrical conductivity of each experimental example, reference example and comparative example sample. Show.
なお、表１では次の略号を使用した。 In Table 1, the following abbreviations were used.
GBL:γ−ブチロラクトン PC :プロピレンカーボネート TMP:トリメチルホスフェート TEP:トリエチルホスフェート TBP:トリブチルホスフェート ［発明の効果］ 本発明により、リチウム塩溶質の溶解性に優れてリチ
ウム電池の電解液に適し、かつ優れた難燃性を示す電解
液を得ることが可能になった。GBL: γ-butyrolactone PC: propylene carbonate TMP: trimethyl phosphate TEP: triethyl phosphate TBP: tributyl phosphate [Effects of the Invention] According to the present invention, it has become possible to obtain an electrolytic solution which is excellent in solubility of a lithium salt solute, is suitable for an electrolytic solution of a lithium battery, and has excellent flame retardancy.
本発明のリチウム電池用電解液は、安全性の高いリチ
ウム電池、とくに携帯用のリチウム電池の電解液として
用いられる。The electrolyte for a lithium battery of the present invention is used as an electrolyte for a highly safe lithium battery, particularly a portable lithium battery.
フロントページの続き (56)参考文献 特開 昭60−23973（ＪＰ，Ａ) 特開 昭61−227377（ＪＰ，Ａ) 特開 昭61−284070（ＪＰ，Ａ) 特開 昭58−206078（ＪＰ，Ａ) 特開 平１−102862（ＪＰ，Ａ) 特開 平２−244565（ＪＰ，Ａ) 特開 昭47−4376（ＪＰ，Ａ) 特開 昭59−3871（ＪＰ，Ａ) 特開 昭62−90877（ＪＰ，Ａ) 特開 昭63−121268（ＪＰ，Ａ) (58)調査した分野(Int.Cl.7，ＤＢ名) H01M 10/40 H01M 6/16 Continuation of front page (56) References JP-A-60-23973 (JP, A) JP-A-61-227377 (JP, A) JP-A-61-284070 (JP, A) JP-A-58-206078 (JP) JP-A-1-102286 (JP, A) JP-A-2-244565 (JP, A) JP-A-47-4376 (JP, A) JP-A-59-3871 (JP, A) 62-90877 (JP, A) JP-A-63-121268 (JP, A) (58) Fields investigated (Int. Cl. 7 , DB name) H01M 10/40 H01M 6/16
Claims (3)
〜４の直鎖状又は分枝状のアルキル基を表わし；−
（Ｃ）−は、直鎖状又は分枝状の炭化水素基における、
１個の炭素原子を有する単位であり、ｋ、ｌ、ｍ、ｎ
は、該炭化水素基の炭素数を示し、ｋ＝２〜８、ｌ、
ｍ、ｎ＝０〜12の整数である。） からなる群より選ばれるリン酸エステルである、リチウ
ム電池用電解液の難燃化剤。1. A compound of the general formula (II): A monocyclic phosphate represented by the general formula (III): A bicyclic phosphate represented by the formula (wherein R 4 is a group having 1 carbon atom)
Represents a linear or branched alkyl group of 1 to 4,
(C)-is a linear or branched hydrocarbon group,
A unit having one carbon atom, k, l, m, n
Represents the number of carbon atoms of the hydrocarbon group, and k = 2 to 8, l,
m and n are integers of 0 to 12. A flame retardant for a lithium battery electrolyte, which is a phosphate selected from the group consisting of:
剤を15重量％以上含有させる、リチウム電池用電解液を
難燃化する方法。2. A method for flame retarding an electrolyte for a lithium battery, comprising the flame retardant according to claim 1 in a solvent of the electrolyte at 15% by weight or more.
有させてそれ以外に溶媒を含有させないことにより、リ
チウム電池用電解液を難燃化する方法。3. A method for making an electrolyte for a lithium battery flame-retardant by incorporating the flame retardant according to claim 1 into the electrolyte and not including a solvent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP02311271A JP3131905B2 (en) | 1990-11-19 | 1990-11-19 | Flame retardant for electrolyte for lithium battery |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP02311271A JP3131905B2 (en) | 1990-11-19 | 1990-11-19 | Flame retardant for electrolyte for lithium battery |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP09710599A Division JP3274102B2 (en) | 1999-04-05 | 1999-04-05 | Flame retardant electrolyte for lithium batteries |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04184870A JPH04184870A (en) | 1992-07-01 |
| JP3131905B2 true JP3131905B2 (en) | 2001-02-05 |
Family
ID=18015132
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP02311271A Expired - Fee Related JP3131905B2 (en) | 1990-11-19 | 1990-11-19 | Flame retardant for electrolyte for lithium battery |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3131905B2 (en) |
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| US9478830B2 (en) | 2013-09-30 | 2016-10-25 | Panasonic Corporation | Non-aqueous electrolyte secondary battery comprising phosphoric acid ester compound containing at least one metal element |
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|---|---|---|---|---|
| CA2119959C (en) * | 1993-03-30 | 2000-03-14 | Soichiro Kawakami | Secondary battery |
| US5691084A (en) * | 1994-03-19 | 1997-11-25 | Hitachi Maxell, Ltd | Organic electrolytic solution secondary cell |
| EP0696077B1 (en) | 1994-07-07 | 1999-03-31 | Mitsui Chemicals, Inc. | Non-aqueous electrolyte solutions and secondary cells comprising the same |
| JP3425493B2 (en) * | 1994-07-28 | 2003-07-14 | 日立マクセル株式会社 | Non-aqueous secondary battery and method of manufacturing the same |
| JPH09180721A (en) * | 1995-12-28 | 1997-07-11 | Mitsui Petrochem Ind Ltd | Electrode for lithium battery, manufacturing method thereof, electrochemical device and manufacturing method thereof |
| TW403922B (en) | 1997-09-11 | 2000-09-01 | Mitsui Chemicals Inc | Electrolytic solution for capacitor and capacitor |
| US6210840B1 (en) | 1997-12-02 | 2001-04-03 | Denso Corporation | Flame-retardant electrolytic solution and nonaqueous secondary battery containing the same |
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1990
- 1990-11-19 JP JP02311271A patent/JP3131905B2/en not_active Expired - Fee Related
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|---|---|
| JPH04184870A (en) | 1992-07-01 |
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| LAPS | Cancellation because of no payment of annual fees |