JPH11317232A - Flame retarder of electrolyte for lithium battery - Google Patents
Flame retarder of electrolyte for lithium batteryInfo
- Publication number
- JPH11317232A JPH11317232A JP11097105A JP9710599A JPH11317232A JP H11317232 A JPH11317232 A JP H11317232A JP 11097105 A JP11097105 A JP 11097105A JP 9710599 A JP9710599 A JP 9710599A JP H11317232 A JPH11317232 A JP H11317232A
- Authority
- JP
- Japan
- Prior art keywords
- electrolyte
- phosphate
- solvent
- lithium battery
- flame retardance
- 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.)
- Granted
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
Abstract
Description
【0001】[0001]
【発明の属する技術分野】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。[0001] 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.
【0002】[0002]
【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。2. Description of the Related Art Conventionally, lithium batteries have been used as electrolytes such as propylene carbonate, γ-butyrolactone,
A solution in which a solute such as lithium perchlorate, lithium borofluoride, lithium phosphofluoride, or lithium trifluoromethanesulfonate is dissolved in a single solvent such as 1,2-dimethoxyethane or a mixed solvent thereof is used.
【0003】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
素は、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, electrical conductivity,
It is necessary that the basic performance as an electrolyte, such as the working potential range, the working temperature range, and the compatibility with the electrode material, be not hindered. 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.
【0004】[0004]
【発明が解決しようとする課題】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。Since the above-mentioned lithium battery uses a very flammable solvent, when the battery is broken due to an internal short circuit or the like, a spark ignites the electrolyte and damages the equipment. And can lead to 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.
【0005】[0005]
【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 exhibiting flame retardancy while maintaining the characteristics as a battery by using a lower phosphate as a solvent or a cosolvent for the electrolyte. The present invention was completed successfully.
【0006】すなわち、本発明は、一般式(I):That is, the present invention provides a compound represented by the general formula (I):
【0007】[0007]
【化2】 Embedded image
【0008】(式中、R1〜R3は、互いに同一でも異な
っていてもよい、炭素数1〜4の直鎖状又は分枝状のア
ルキル基である。)で示されるトリアルキルホスフェー
トである、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
させる、リチウム電池用電解液を難燃化する方法に関す
る。(Wherein, R 1 to R 3 are linear or branched alkyl groups having 1 to 4 carbon atoms, which may be the same or different from each other). The present invention relates to a flame retardant for an electrolyte for a lithium battery; and to a method for flame retarding an electrolyte for a lithium battery, wherein the solvent for the electrolyte contains 15% by weight or more of the flame retardant.
【0009】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.
【0010】[0010]
【発明の実施の形態】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。BEST MODE FOR CARRYING OUT THE INVENTION The phosphate ester used is a trialkyl phosphate (I) represented by the following general formula, a monocyclic phosphate (II) and a bicyclic phosphate (III) in which alkyl groups are bonded to each other. It is.
【0011】[0011]
【化3】 Embedded image
【0012】(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。)(Wherein, R 1 to R 4 are a linear or branched alkyl group having 1 to 4 carbon atoms, and R 1 to R 3 may be different from each other. Is a unit having one carbon atom in a linear or branched hydrocarbon group,
k, l, m, and n indicate the number of carbon atoms of the hydrocarbon group, and k =
2 to 8, 1, m, and n are integers of 0 to 12. )
【0013】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、Specific examples of the phosphate represented by formula (I) include trimethyl phosphate, dimethyl ethyl phosphate, methyl ethyl propyl phosphate, methyl diethyl phosphate, triethyl phosphate, tripropyl phosphate, and tributyl phosphate; ) As methylethylene phosphate and methyltrimethylene phosphate; and as represented by general formula (III):
【0014】[0014]
【化4】 Embedded image
【0015】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。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.
【0016】本発明で用いるリン酸エステルは、一般式
(I)で示されるトリアルキルホスフェートである。The phosphate ester used in the present invention is a trialkyl phosphate represented by the general formula (I).
【0017】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 above phosphate ester in the electrolytic solution varies depending on the required performance of the lithium battery, but 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 to a conventional electrolytic solution as a cosolvent, good flame retardancy can be obtained by using 15% by weight or more, preferably 30% by weight or more.
【0018】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。Examples of the solvent for mixing the above phosphate ester include carbonate solvents such as ethylene carbonate, propylene carbonate and butylene carbonate;
Lactone solvents such as butyrolactone; and ether solvents such as 1,2-dimethoxyethane, 1,3-dioxolan, and tetrahydrofuran.
【0019】また、溶質としては、LiClO4、Li
BF4、LiPF6、LiAsF6、LiCF3SO3、L
iAlCl4等を例示することができる。As the solute, LiClO 4 , Li
BF 4 , LiPF 6 , LiAsF 6 , LiCF 3 SO 3 , L
iAlCl 4 and the like can be exemplified.
【0020】[0020]
【実施例】以下に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 The present invention will be described more specifically with reference to reference examples and comparative examples.
【0021】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.
【0022】実施例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15mm、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。Example 1 An electrolytic solution prepared by dissolving LiBF 4 at a concentration of 1 mol in trimethyl phosphate (electrical conductivity at 25 ° C. 5.6 mS / cm)
In addition, width 15mm, length 320mm, thickness 40μm, density 0.
6 g / cm 3 of manila paper was soaked for 1 minute and suspended vertically for 3 minutes to remove excess electrolyte. The manila paper impregnated with the electrolyte in this manner was horizontally fixed to a sample holder having support needles at intervals of 25 mm, and one end of the paper was ignited with a match.
【0023】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、
実施例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 An electrolytic solution in which 1 mol of LiBF 4 was dissolved in γ-butyrolactone (electric conductivity at 25 ° C .: 7.8 mS / cm)
Manila paper was immersed under the same conditions as in Example 1, and the burning rate was determined from the burning time of 300 mm by the same ignition test. The burning rate was 10 mm / s.
【0024】実施例2、3 実施例1において、溶媒をトリエチルホスフェート(実
施例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(実施例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。Examples 2 and 3 In Example 1, the solvent was changed to triethyl phosphate (Example 2) and a mixed solvent of γ-butyrolactone and trimethyl phosphate at a weight ratio of 1: 1 (Example 3).
A similar ignition test was performed. All exhibited high flame retardancy.
【0025】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. As a result, the composition was flammable.
【0026】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, Manila paper impregnated with nothing, Reference Examples 2 to 7
A similar ignition test was performed on Manila paper impregnated with only a solvent.
【0027】これらの着火試験の結果;ならびに各実施
例、比較例、参考例(参考例1を除く)試料の引火点;
及び各実施例、比較例試料の電気伝導度をまとめて表1
に示す。The results of these ignition tests; and the flash point of each Example, Comparative Example and Reference Example (excluding Reference Example 1) samples;
Table 1 summarizes the electrical conductivities of the samples of Examples and Comparative Examples.
Shown in
【0028】なお、表1では次の略号を使用した。 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The following abbreviations are used in Table 1. GBL: γ-butyrolactone PC: propylene carbonate TMP: trimethyl phosphate TEP: triethyl phosphate TBP: tributyl phosphate
【0029】[0029]
【表1】 [Table 1]
【0030】[0030]
【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。According to the present invention, it has become possible to obtain an electrolyte having excellent solubility of a lithium salt solute, suitable for an electrolyte of a lithium battery, and exhibiting excellent flame retardancy.
【0031】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.
Claims (3)
い、炭素数1〜4の直鎖状又は分枝状のアルキル基であ
る。)で示されるトリアルキルホスフェートである、リ
チウム電池用電解液の難燃化剤。1. A compound of the general formula (I): (Wherein, R 1 to R 3 are linear or branched alkyl groups having 1 to 4 carbon atoms, which may be the same or different from each other). Flame retardant for battery electrolyte.
載の難燃化剤。2. The flame retardant according to claim 1, wherein R 1 to R 3 are methyl groups.
の難燃化剤を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。3. A method for flame retarding an electrolyte for a lithium battery, comprising the flame retardant according to claim 1 or 15% by weight or more in a solvent of the electrolyte.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP09710599A JP3274102B2 (en) | 1999-04-05 | 1999-04-05 | Flame retardant electrolyte for lithium batteries |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP09710599A JP3274102B2 (en) | 1999-04-05 | 1999-04-05 | Flame retardant electrolyte for lithium batteries |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP02311271A Division JP3131905B2 (en) | 1990-11-19 | 1990-11-19 | Flame retardant for electrolyte for lithium battery |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH11317232A true JPH11317232A (en) | 1999-11-16 |
JP3274102B2 JP3274102B2 (en) | 2002-04-15 |
Family
ID=14183336
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP09710599A Expired - Fee Related JP3274102B2 (en) | 1999-04-05 | 1999-04-05 | Flame retardant electrolyte for lithium batteries |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP3274102B2 (en) |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1050916A1 (en) * | 1999-05-03 | 2000-11-08 | Wilson Greatbatch Ltd. | Phosphate additives for nonaqueous electrolyte in rechargeable electrochemical cells |
US6511772B2 (en) | 2001-01-17 | 2003-01-28 | Wilson Greatbatch Ltd. | Electrochemical cell having an electrode with a phosphate additive in the electrode active mixture |
US6797437B2 (en) | 2001-12-28 | 2004-09-28 | Quallion Llc | Electrolyte system and energy storage device using same |
US6919141B2 (en) | 1998-10-22 | 2005-07-19 | Wilson Greatbatch Technologies, Inc. | Phosphate additives for nonaqueous electrolyte rechargeable electrochemical cells |
US7833648B2 (en) | 2006-07-27 | 2010-11-16 | Lg Chem, Ltd. | Electrochemical device with high safety at over-voltage and high temperature |
WO2014092121A1 (en) | 2012-12-13 | 2014-06-19 | エリーパワー株式会社 | Method for producing non-aqueous electrolyte secondary battery |
WO2014091606A1 (en) | 2012-12-13 | 2014-06-19 | エリーパワー株式会社 | Non-aqueous electrolytic solution secondary battery and method for producing non-aqueous electrolytic solution secondary battery |
WO2016000982A1 (en) * | 2014-06-30 | 2016-01-07 | Basf Se | Process for making cathode materials for lithium ion batteries |
US9748608B2 (en) | 2012-03-02 | 2017-08-29 | Nec Corporation | Second battery comprising a phosphate ester compound and a fluorinated carbonate compound |
US9876254B2 (en) | 2012-06-20 | 2018-01-23 | Fujifilm Corporation | Non-aqueous liquid electrolyte for secondary battery and non-aqueous liquid electrolyte secondary battery |
CN107834109A (en) * | 2017-11-24 | 2018-03-23 | 杨彬 | A kind of fire-retardant lithium battery electrolytes |
CN112635825A (en) * | 2020-11-12 | 2021-04-09 | 捷威动力工业江苏有限公司 | Ternary lithium ion battery electrolyte and lithium ion battery |
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