JP2007077052A - 環状カーボネート変性有機ケイ素化合物、それを含有する非水電解液並びに二次電池及びキャパシタ - Google Patents
環状カーボネート変性有機ケイ素化合物、それを含有する非水電解液並びに二次電池及びキャパシタ Download PDFInfo
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- JP2007077052A JP2007077052A JP2005265551A JP2005265551A JP2007077052A JP 2007077052 A JP2007077052 A JP 2007077052A JP 2005265551 A JP2005265551 A JP 2005265551A JP 2005265551 A JP2005265551 A JP 2005265551A JP 2007077052 A JP2007077052 A JP 2007077052A
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- Japan
- Prior art keywords
- group
- cyclic carbonate
- aqueous electrolyte
- ppm
- carbonate
- 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.)
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- 125000004122 cyclic group Chemical group 0.000 title claims abstract description 28
- 239000011255 nonaqueous electrolyte Substances 0.000 title claims abstract description 27
- 239000003990 capacitor Substances 0.000 title claims abstract description 18
- 150000003377 silicon compounds Chemical class 0.000 title abstract 3
- 150000005676 cyclic carbonates Chemical group 0.000 claims abstract description 14
- 229910001416 lithium ion Inorganic materials 0.000 claims abstract description 13
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- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
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- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000003277 amino group Chemical group 0.000 claims abstract description 5
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- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 5
- 125000000962 organic group Chemical group 0.000 claims abstract description 4
- 239000008151 electrolyte solution Substances 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 22
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
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- 159000000002 lithium salts Chemical group 0.000 claims description 3
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- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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Images
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/42—Methods or arrangements for servicing or maintenance of secondary cells or secondary half-cells
- H01M10/4235—Safety or regulating additives or arrangements in electrodes, separators or electrolyte
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/54—Electrolytes
- H01G11/58—Liquid electrolytes
- H01G11/64—Liquid electrolytes characterised by additives
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
- H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/04—Hybrid capacitors
- H01G11/06—Hybrid capacitors with one of the electrodes allowing ions to be reversibly doped thereinto, e.g. lithium ion capacitors [LIC]
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M4/00—Electrodes
- H01M4/02—Electrodes composed of, or comprising, active material
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Abstract
【化1】
[R1は水酸基、及びハロゲン原子で置換されていてもよい炭素数1〜30のアルキル基、アリール基、アラルキル基、アミノ置換アルキル基、カルボキシル置換アルキル基、アルコキシ基、アリーロキシ基から選択される同一もしくは異種の一価の基であり、Aは下記式(3)
【化2】
(Qはエーテル結合又はエステル結合を含有してもよい炭素数3〜20の二価有機基である。)
で示される環状カーボネート基である。xは1〜4の整数、a、bは1.0≦a≦2.5、0.001≦b≦1.5の正数、a+bは1.001≦a+b≦3である。]
【効果】 本発明の式(1)又は(2)の環状カーボネート基を有する有機基で変性したシラン又はシロキサンを含む非水電解液を使用した電池は、優れた温度特性及び高出力特性を有する。
【選択図】 なし
Description
[但し、式中のR1は水酸基、及びハロゲン原子で置換されていてもよい炭素数1〜30のアルキル基、アリール基、アラルキル基、アミノ置換アルキル基、カルボキシル置換アルキル基、アルコキシ基、アリーロキシ基から選択される同一もしくは異種の一価の基であって、Aは下記一般式(3)
(但し、Qはエーテル結合又はエステル結合を含有してもよい炭素数3〜20の二価有機基である。)
で示される環状カーボネート基である。xは1〜4の整数であり、a、bはそれぞれ1.0≦a≦2.5、0.001≦b≦1.5の正数であり、a+bは1.001≦a+b≦3である。]
また、本発明は、非水溶媒と、電解質塩と、上記環状カーボネート変性有機ケイ素化合物とを必須成分とすることを特徴とする非水電解液を提供する。
更に、本発明は、この非水電解液を含む二次電池、特にリチウムイオン二次電池及び電気化学キャパシタを提供する。
導電剤としては、一般的に黒鉛、カーボンブラック等の炭素系材料や、銅、ニッケル等の金属材料が挙げられる。
集電体としては、正極用にはアルミニウム又はその合金、負極用には銅、ステンレス、ニッケル等の金属又はそれらの合金等が挙げられる。
撹拌機、温度計及び還流管を備えた反応器にアリルエチレンカーボネート32gとトルエン100g及び塩化白金酸0.5質量%のトルエン溶液0.05gを仕込み、撹拌しながら70℃にてペンタメチルジシロキサン41gを滴下した。SiH基に対する末端不飽和基のモル比は約0.9で行った。滴下終了後、2時間80℃にて熟成して反応を完結させた。反応液を減圧下で精密蒸留を行い、145℃/50Paのフラクションをとることにより、環状カーボネート基で変性したシロキサンを収率90%で得た。粘度は15mPa・s、比重は0.991であった。ガスクロマトグラフィー分析による純度は99.2%であった。重アセトンを測定溶剤とした1H−NMRの測定を行ったところ、0.1ppm(15H,s)、0.61ppm(2H,m)、1.50ppm(2H,m)、1.80ppm(2H,m)、4.12ppm(1H,dd)、4.60ppm(1H,dd)、4.81ppm(1H,tt)となった。以上から下記の環状カーボネート変性シロキサン(前記化合物[II])であることを確認した。
撹拌機、温度計及び還流管を備えた反応器にアリルエチレンカーボネート26gとトルエン100g及び塩化白金酸0.5質量%のトルエン溶液0.05gを仕込み、撹拌しながら70℃にて1,1,1,3,5,5,5−ヘプタメチルトリシロキサン49gを滴下した。SiH基に対する末端不飽和基のモル比は約0.9で行った。滴下終了後、2時間80℃にて熟成して反応を完結させた。反応液を減圧下で精密蒸留を行い、156℃/50Paのフラクションをとることにより、環状カーボネート基で変性したシロキサンを収率97%で得た。粘度は16mPa・s、比重は0.985であった。ガスクロマトグラフィー分析による純度は96.2%であった。重アセトンを測定溶剤とした1H−NMRの測定を行ったところ、0.1ppm(21H,ss)、0.55ppm(2H,m)、1.51ppm(2H,m)、1.81ppm(2H,m)、4.12ppm(1H,dd)、4.60ppm(1H,dd)、4.81ppm(1H,tt)となった。以上から下記の環状カーボネート変性シロキサン(前記化合物[IV])であることを確認した。
撹拌機、温度計及び還流管を備えた反応器にアリロキシプロピレンカーボネート32gとトルエン100g及び塩化白金酸0.5質量%のトルエン溶液0.05gを仕込み、撹拌しながら70℃にてペンタメチルジシロキサン33gを滴下した。SiH基に対する末端不飽和基のモル比は約0.9で行った。滴下終了後、2時間80℃にて熟成して反応を完結させた。反応液を減圧下で精密蒸留を行い、124℃/13Paのフラクションをとることにより、環状カーボネート基で変性したシロキサンを収率90%で得た。粘度は19mPa・s、比重は1.015であった。ガスクロマトグラフィー分析による純度は96.1%であった。重アセトンを測定溶剤とした1H−NMRの測定を行ったところ、0.1ppm(15H,s)、0.45ppm(2H,m)、1.51ppm(2H,m)、3.39ppm(2H,t)、3.61ppm(2H,m)、4.27ppm(1H,dd)、4.48ppm(1H,dd)、4.84ppm(1H,m)となった。以上から下記の環状カーボネート変性シロキサンであることを確認した。
撹拌機、温度計及び還流管を備えた反応器にアリロキシプロピレンカーボネート32gとトルエン100g及び塩化白金酸0.5質量%のトルエン溶液0.05gを仕込み、撹拌しながら70℃にて1,1,1,3,5,5,5−ヘプタメチルトリシロキサン49gを滴下した。SiH基に対する末端不飽和基のモル比は約0.9で行った。滴下終了後、2時間80℃にて熟成して反応を完結させた。137.5℃/13Paのフラクションをとることにより、環状カーボネート基で変性したシロキサンを収率73%で得た。粘度は26mPa・s、比重は1.004であった。ガスクロマトグラフィー分析による純度は97.7%であった。重アセトンを測定溶剤とした1H−NMRの測定を行ったところ、0.1ppm(21H,ss)、0.51ppm(2H,m)、1.60ppm(2H,m)、3.47ppm(2H,t)、3.70ppm(2H,m)、4.36ppm(1H,dd)、4.56ppm(1H,dd)、4.91ppm(1H,m)となった。以上から下記の環状カーボネート変性シロキサンであることを確認した。
撹拌機、温度計及び還流管を備えた反応器にビニルエチレンカーボネート100gとトルエン100g及び塩化白金酸0.5質量%のトルエン溶液0.05gを仕込み、撹拌しながら60℃にてペンタメチルジシロキサン143gを滴下した。SiH基に対する末端不飽和基のモル比は約0.9で行った。滴下終了後、2時間80℃にて熟成して反応を完結させた。反応液を減圧下で精密蒸留を行い、99℃/5Paのフラクションをとることにより、環状カーボネート基で変性したシロキサンを収率52%で得た。粘度は9.3mPa・s、比重は0.996であった。ガスクロマトグラフィー分析による純度は98.9%であった。重アセトンを測定溶剤とした1H−NMRの測定を行ったところ、0.10ppm(15H,s)、0.55ppm(2H,m)、1.78ppm(2H,m)、4.15ppm(1H,dd)、4.59ppm(1H,dd)、4.78ppm(1H,m)となった。以上から下記の環状カーボネート変性シロキサンであることを確認した。
撹拌機、温度計及び還流管を備えた反応器にビニルエチレンカーボネート100gとトルエン100g及び塩化白金酸0.5質量%のトルエン溶液0.05gを仕込み、撹拌しながら70℃にて1,1,1,3,5,5,5−ヘプタメチルトリシロキサン216gを滴下した。SiH基に対する末端不飽和基のモル比は約0.9で行った。滴下終了後、2時間80℃にて熟成して反応を完結させた。反応液を減圧下で精密蒸留を行い、120℃/7Paのフラクションをとることにより、環状カーボネート基で変性したシロキサンを収率42%で得た。粘度は13mPa・s、比重は0.990であった。ガスクロマトグラフィー分析による純度は96.1%であった。重アセトンを測定溶剤とした1H−NMRの測定を行ったところ、0.1ppm(21H,ss)、0.56ppm(2H,m)、1.78ppm(2H,m)、4.15ppm(1H,dd)、4.76ppm(1H,dd)、4.63ppm(1H,tt)となった。以上から下記の環状カーボネート変性シロキサンであることを確認した。
撹拌機、温度計及び還流管を備えた反応器にアリロキシプロピレンカーボネート100gとトルエン100g及び塩化白金酸0.5質量%のトルエン溶液0.05gを仕込み、撹拌しながら70℃にてトリメトキシシラン93gを滴下した。SiH基に対する末端不飽和基のモル比は約0.83で行った。滴下終了後、2時間90℃にて熟成し、反応液を減圧下で蒸留し、134℃/2Paのフラクションをとることにより、環状カーボネート変性トリメトキシシランを収率75質量%で得た。粘度は21mPa・s、比重は1.1797であった。ガスクロマトグラフィー分析による純度は97.1%であった。重アセトンを測定溶剤とした1H−NMRの測定を行ったところ、0.62ppm(2H,m)、1.64ppm(2H,m)、3.45ppm(9H,s)、3.64ppm(4H,m)、4.34ppm(1H,m)、4.53ppm(1H,m)、4.90ppm(1H,m)となった。以上から下記の環状カーボネート変性シランであることを確認した。
撹拌機、温度計及び還流管を備えた反応器に実施例5の環状カーボネート変性トリメトキシシラン56gとトリメチルメトキシシラン104g及びメタノール80gを仕込み、−10℃に冷却し、濃硫酸4gを添加した。―10℃に冷却したままイオン交換水17gをゆっくりと加え、加水分解を行った。2時間撹拌した後、室温に戻し、トルエンを加えて水洗を行った。トルエン層を分離し、無水硫酸ナトリウムを加えて乾燥した。反応液を130℃/10Paの減圧下で1時間揮発分留去を行い、下記の環状カーボネート変性シロキサンを収率91質量%で得た。ガスクロマトグラフィー分析による純度は91.3%であった。粘度は38mPa・sで、比重は1.01であった。重アセトンを測定溶剤とした1H−NMRの測定を行ったところ、0.14ppm(27H,s)、0.52ppm(2H,m)、1.62ppm(2H,m)、3.48ppm(2H,t)、3.69ppm(2H,m)、4.36ppm(1H,dd)、4.56ppm(1H,dd)、4.92ppm(1H,m)となり、下記の構造であることを確認した。
(非水電解液の調製)
エチレンカーボネート(EC)とジエチルカーボネート(DEC)に実施例3〜6のシロキサンを表1の割合で溶解した。次に、LiPF6を1.3mol/Lの濃度で溶解し、非水電解液とした。また、比較例として、非水電解液にシロキサンを含有しない場合とポリエーテル変性シリコーンを5体積%添加した場合についても同様の評価を行った。
正極材料として、LiCoO2を活物質とし、集電体としてアルミ箔を用いた単層シート(パイオニクス(株)製、商品名;ピオクセル C−100)を用いた。また、負極材料として、黒鉛を活物質とし、集電体として銅箔を用いた単層シート(パイオニクス(株)製、商品名;ピオクセル A−100)を用いた。セパレータはポリオレフィンの多孔質膜(セルガード社製、商品名;セルガード2400)を用いた。
アルゴン雰囲気下のドライボックス内で、前記電池材料と正極導電体を兼ねるステンレス製缶体と負極導電体を兼ねるステンレス製封口板と絶縁用ガスケットを用いて2032コイン型電池を組み立てた。
25℃下で充電(2.0mA一定電流下で4.2Vまで)と放電(2.0mA一定電流下で2.5Vまで)を100サイクル繰り返した。1サイクル目の放電容量を100とした時の各サイクルの放電容量を放電容量維持率(%)として図1に示した。
Claims (10)
- 下記一般式(1)又は(2)で示される環状カーボネート変性有機ケイ素化合物。
[但し、式中のR1は水酸基、及びハロゲン原子で置換されていてもよい炭素数1〜30のアルキル基、アリール基、アラルキル基、アミノ置換アルキル基、カルボキシル置換アルキル基、アルコキシ基、アリーロキシ基から選択される同一もしくは異種の一価の基であって、Aは下記一般式(3)
(但し、Qはエーテル結合又はエステル結合を含有してもよい炭素数3〜20の二価有機基である。)
で示される環状カーボネート基である。xは1〜4の整数であり、a、bはそれぞれ1.0≦a≦2.5、0.001≦b≦1.5の正数であり、a+bは1.001≦a+b≦3である。] - 非水溶媒と、電解質塩と、請求項1記載の環状カーボネート変性有機ケイ素化合物とを必須成分とすることを特徴とする非水電解液。
- 環状カーボネート変性有機ケイ素化合物におけるR1が炭素数1〜6のアルキル基又はフッ素置換アルキル基である請求項2記載の非水電解液。
- 前記環状カーボネート基(3)中のQが−(CH2)3−である請求項2又は3記載の非水電解液。
- 前記環状カーボネート基(3)中のQが−(CH2)3−O−CH2−である請求項2又は3記載の非水電解液。
- 環状カーボネート変性有機ケイ素化合物の含有量が非水電解液全体の0.001体積%以上であることを特徴とする請求項2乃至5のいずれか1項記載の非水電解液。
- 前記電解質塩がリチウム塩であることを特徴とする請求項2乃至6のいずれか1項記載の非水電解液。
- 請求項2乃至7のいずれか1項記載の非水電解液を含むことを特徴とする二次電池。
- 請求項2乃至7のいずれか1項記載の非水電解液を含むことを特徴とする電気化学キャパシタ。
- 請求項2乃至7のいずれか1項記載の非水電解液を含むことを特徴とするリチウムイオン二次電池。
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TW (1) | TW200723573A (ja) |
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KR20180036733A (ko) * | 2015-07-30 | 2018-04-09 | 모멘티브 퍼포먼스 머티리얼즈 인크. | 실록산 코폴리머 및 그 실록산 코폴리머를 포함하여 구성되는 고체 폴리머 전해질 |
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JP2010287564A (ja) * | 2009-06-15 | 2010-12-24 | Taiwan Hopax Chemicals Manufacturing Co Ltd | 電気化学素子用電解質およびその電気化学素子 |
WO2012039250A1 (ja) * | 2010-09-22 | 2012-03-29 | 富士フイルム株式会社 | 非水二次電池用電解液及びリチウム二次電池 |
WO2012039251A1 (ja) * | 2010-09-22 | 2012-03-29 | 富士フイルム株式会社 | 非水二次電池用電解液及びリチウム二次電池 |
JP2012089468A (ja) * | 2010-09-22 | 2012-05-10 | Fujifilm Corp | 非水二次電池用電解液及びリチウム二次電池 |
JP2012089469A (ja) * | 2010-09-22 | 2012-05-10 | Fujifilm Corp | 非水二次電池用電解液及びリチウム二次電池 |
US9293787B2 (en) | 2010-09-22 | 2016-03-22 | Fujifilm Corporation | Nonaqueous electrolyte for secondary battery and lithium secondary battery |
JP5676733B1 (ja) * | 2013-09-02 | 2015-02-25 | 財團法人工業技術研究院 | 電解質溶液、リチウム電池および電気化学キャリア構造 |
JP2015050182A (ja) * | 2013-09-02 | 2015-03-16 | 財團法人工業技術研究院Industrial Technology Research Institute | 電解質溶液、リチウム電池および電気化学キャリア構造 |
KR20180036733A (ko) * | 2015-07-30 | 2018-04-09 | 모멘티브 퍼포먼스 머티리얼즈 인크. | 실록산 코폴리머 및 그 실록산 코폴리머를 포함하여 구성되는 고체 폴리머 전해질 |
KR102625966B1 (ko) | 2015-07-30 | 2024-01-18 | 모멘티브 퍼포먼스 머티리얼즈 인크. | 실록산 코폴리머 및 그 실록산 코폴리머를 포함하여 구성되는 고체 폴리머 전해질 |
Also Published As
Publication number | Publication date |
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TW200723573A (en) | 2007-06-16 |
CN1931863A (zh) | 2007-03-21 |
JP4656312B2 (ja) | 2011-03-23 |
US20070059607A1 (en) | 2007-03-15 |
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