JP5974748B2 - リチウムイオン二次電池用シール材及びリチウムイオン二次電池用シール材組成物 - Google Patents
リチウムイオン二次電池用シール材及びリチウムイオン二次電池用シール材組成物 Download PDFInfo
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- JP5974748B2 JP5974748B2 JP2012199773A JP2012199773A JP5974748B2 JP 5974748 B2 JP5974748 B2 JP 5974748B2 JP 2012199773 A JP2012199773 A JP 2012199773A JP 2012199773 A JP2012199773 A JP 2012199773A JP 5974748 B2 JP5974748 B2 JP 5974748B2
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- Prior art keywords
- sealing material
- secondary battery
- polymer
- lithium ion
- ion secondary
- 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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- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 1
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- 229910021555 Chromium Chloride Inorganic materials 0.000 description 1
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- 239000002033 PVDF binder Substances 0.000 description 1
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- 230000002378 acidificating effect Effects 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
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- 239000012965 benzophenone Substances 0.000 description 1
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- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 125000002897 diene group Chemical group 0.000 description 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical class O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 1
- 239000006232 furnace black Substances 0.000 description 1
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- BNRNAKTVFSZAFA-UHFFFAOYSA-N hydrindane Chemical compound C1CCCC2CCCC21 BNRNAKTVFSZAFA-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
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- KXUHSQYYJYAXGZ-UHFFFAOYSA-N isobutylbenzene Chemical compound CC(C)CC1=CC=CC=C1 KXUHSQYYJYAXGZ-UHFFFAOYSA-N 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- CETVQRFGPOGIQJ-UHFFFAOYSA-N lithium;hexane Chemical compound [Li+].CCCCC[CH2-] CETVQRFGPOGIQJ-UHFFFAOYSA-N 0.000 description 1
- 238000010551 living anionic polymerization reaction Methods 0.000 description 1
- 238000010550 living polymerization reaction Methods 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N methyl cyclohexan-4-ol Natural products CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 description 1
- UQADNXUWLBEGLY-UHFFFAOYSA-N n,n-diethyl-4-phenylbut-3-en-1-amine Chemical compound CCN(CC)CCC=CC1=CC=CC=C1 UQADNXUWLBEGLY-UHFFFAOYSA-N 0.000 description 1
- UBHHTPOLMACCDD-UHFFFAOYSA-N n,n-dimethyl-4-phenylbut-3-en-1-amine Chemical compound CN(C)CCC=CC1=CC=CC=C1 UBHHTPOLMACCDD-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
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- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- WRARULQOSOCOQD-UHFFFAOYSA-N penta-2,4-diynenitrile Chemical compound C#CC#CC#N WRARULQOSOCOQD-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920001690 polydopamine Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920000346 polystyrene-polyisoprene block-polystyrene Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- ZRLVQFQTCMUIRM-UHFFFAOYSA-N potassium;2-methylbutan-2-olate Chemical compound [K+].CCC(C)(C)[O-] ZRLVQFQTCMUIRM-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 1
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- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
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- 229910052717 sulfur Inorganic materials 0.000 description 1
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- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
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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
- Electric Double-Layer Capacitors Or The Like (AREA)
- Sealing Battery Cases Or Jackets (AREA)
Description
即ち、本発明によれば、
(2) 前記ジエン系ゴムは、1,4−シス含有量90%以上のブタジエンゴムであることを特徴とする(1)記載の二次電池用シール材、
(3) (1)または(2)に記載の二次電池用シール材と、有機液状物質とを含み、前記有機液状物質に対して前記二次電池用シール材が1〜30wt%配合されることを特徴とする二次電池用シール材組成物
が提供される。
本発明の二次電池用シール材に用いるジエン系ゴムは、ジエン系モノマーを重合することにより得られる共役ジエン単量体単位を含むポリマーであれば格別に限定はされないが、共役ジエンホモポリマー及び共役ジエン系共重合ポリマーからなる群から選ばれる少なくとも1種が好適に用いられる。
また、本発明で用いるジエン系ゴムは、1,4−シス含有量が90%以上であるブタジエンゴムであることが好ましい。
(イソブチレンブロック−スチレンブロックを含んでなるポリマー)
本発明において、イソブチレンブロック−スチレンブロックを含んでなるポリマーとしては、シブスター(カネカ社製)を用いることが好ましい。
本発明の二次電池用シール材には、上述の共役ジエン系ポリマー、環状オレフィン系ポリマーの他に、さらに分散剤、紫外線吸収剤、老化防止剤等の成分が含まれていてもよい。これらは後述の絶縁ガスケットの性能を劣化させず、電解液と反応せず、また、電解液に溶解しないものでなければ特に限られない。
本発明の二次電池用シール材は、上述のジエン系ゴム、イソブチレンブロック−スチレンブロックを含んでなるポリマー及び必要に応じて配合されるその他の成分を含んでなる。シール材中、ジエン系ゴムとイソブチレンブロック−スチレンブロックを含んでなるポリマーとの合計量は80wt%以上、好ましくは85wt%以上、より好ましくは90wt%以上である。水添ポリマーと共役ジエン系ポリマーとの合計量が少なすぎると得られるシール材層の耐電解液性及びシール性が低下する。
本発明の二次電池用シール材組成物は、上述の共役ジエン系ポリマー、環状オレフィン系ポリマー、有機液状物質、及び必要に応じて配合されるその他の成分を含んでなり、上述の二次電池用シール材及び有機液状物質を含むことが好ましい。
シール材は、有機液状物質中に1〜30wt%含まれることが好ましく、5〜25wt%含まれることがより好ましい。
本発明の二次電池用シール材及び二次電池用シール材組成物を用いる二次電池は、発電要素を収納した金属容器の開口部に装着された絶縁ガスケットと金属容器との間、および/又は絶縁ガスケットと封口体との間に、上述のシール材組成物で形成されたシール材層が設けられてなる。二次電池に用いる金属容器の素材、発電要素、絶縁ガスケットは、一般に使用されているものでよい。この二次電池は、その発電要素を金属容器に収納され密閉されたものである。
実施例および比較例において得られたシール材のフィルム1とアルミ箔との剥離強度を、180°剥離法により測定した。幅25mmのリボン状に切断した試験片に、粘着剤付きのアルミテープを貼り合せて、引っ張り試験器を用いて剥離強度を測定した。アルミテープとシール材のフィルム1との界面で剥離した場合にはA、シール材のフィルム1とアルミ箔との界面で剥離した場合には剥離強度を測定し、表1に示した。
実施例および比較例において得られたフィルム1を外側にして−20℃において折り曲げた。曲げた部分を観察し、ひび割れ、剥離等を観察した。ひび割れ、剥離等が観察されなかった場合には○、ひび割れ、剥離等が観察された場合には×として、表1に示した。
実施例および比較例において得られたフィルム2を硫酸でpH3に調整した水に浸漬し(80℃、240時間)し、取り出したフィルムの表面に付着した液滴を除去した後、外観を観察した。評価は以下の基準により行い、表1に示した。
A:変化なし
B:表面に凹凸あり
C:表面粗さ大(全体に大きな凹凸あり、Ra>100μm)
また、剥離強度については、PETフィルムとシール材の界面で剥離した場合をA、シール材とPETフィルムの界面で剥離した場合をBとし、表1に示した。
(1,3−ブタジエン重合体(ジエン系ゴム)の重合)
10リットルの攪拌機付きオートクレーブにトルエン5000g、ブタジエン810gを加え、十分攪拌した後、ジエチルアルミニウムクロライド0.27mol、塩化クロム・ピリジン錯体0.6mmolを加え、60℃で3時間攪拌しながら重合した。その後、メタノール100mlを加えて重合を停止した。重合停止後、室温まで冷却した後、重合液を取り出した。得られた重合液を水蒸気凝固した後、60℃で48時間真空乾燥して固体状のポリマー780gを得た。得られたポリマーのMwは390,000であった。
また、13C−NMRスペクトルの結果からこのポリマーのシス体含量は94%であった。
上述のようにして得られたジエン系ゴム50重量部、イソブチレンブロック−スチレンブロックを含んでなるポリマーとしてシブスター50重量部及び有機溶媒(キシレン)900重量部を撹拌翼付きフラスコで50℃に加温しながら混合し、均一な溶液を得た。
得られた溶液を、アルミ箔(20μm厚)に、ギャップ200μmのドクターブレードでキャストし、80℃で20分間加熱乾燥させてフィルム1を得た。
試験片を得る際に調製する溶液に用いるポリマーをジエン系ゴム55重量部、シブスター45重量部とした以外は、実施例1と同様にフィルム1及びフィルム2を得た。
試験片を得る際に調製する溶液に用いるポリマーをジエン系ゴム60重量部、シブスター40重量部とした以外は、実施例1と同様にフィルム1及びフィルム2を得た。
試験片を得る際に調整する溶液に用いるポリマーをジエン系ゴム30重量部、シブスター70重量部とした以外は、実施例1と同様にフィルム1及びフィルム2を得た。
試験片を得る際に調製する溶液に用いるポリマーに代えてアスファルト100重量部を用いた以外は、実施例1と同様にフィルム1及びフィルム2を得た。
試験片を得る際に調製する溶液に用いるポリマーをシブスター100重量部とし、ジエン系ゴムを用いなかった以外は、実施例1と同様にフィルム1及びフィルム2を得た。
Claims (3)
- ジエン系ゴムと、イソブチレンブロックおよびスチレンブロックを含んでなるポリマーとを含み、
前記ジエン系ゴムと前記イソブチレンブロックおよびスチレンブロックを含んでなるポリマーとの合計量が80wt%以上であり、
前記ジエン系ゴムと前記イソブチレンブロックおよびスチレンブロックを含んでなるポリマーとの重量比が、(ジエン系ゴム/イソブチレンブロックおよびスチレンブロックを含んでなるポリマー)にて40/60〜80/20であることを特徴とするリチウムイオン二次電池用シール材。 - 前記ジエン系ゴムは、1,4−シス含有量90%以上のブタジエンゴムであることを特徴とする請求項1記載のリチウムイオン二次電池用シール材。
- 請求項1または2に記載のリチウムイオン二次電池用シール材と、有機液状物質とを含み、
前記有機液状物質に対して前記リチウムイオン二次電池用シール材が1〜30wt%配合されることを特徴とするリチウムイオン二次電池用シール材組成物。
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EP3943568A4 (en) * | 2019-03-20 | 2022-11-02 | Zeon Corporation | SEALING MATERIAL FOR ELECTROCHEMICAL DEVICE AND SEALING MATERIAL COMPOSITION |
EP3943569A4 (en) * | 2019-03-20 | 2022-11-02 | Zeon Corporation | SEALANT FOR ELECTROCHEMICAL DEVICE AND SEALANT COMPOSITION |
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JP2008300183A (ja) * | 2007-05-31 | 2008-12-11 | Bridgestone Corp | ダイレクトメタノール型燃料電池用部材 |
EP2502962B1 (en) * | 2009-11-18 | 2015-03-04 | Ajinomoto Co., Inc. | Resin composition |
JP5499827B2 (ja) * | 2010-03-29 | 2014-05-21 | 日本ゼオン株式会社 | 有機電解液電池用シール剤組成物及び有機電解液電池 |
KR101638663B1 (ko) * | 2010-05-17 | 2016-07-11 | 제온 코포레이션 | 이차 전지용 시일재 조성물, 그 제조 방법 및 그것을 사용한 이차 전지 |
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EP3943568A4 (en) * | 2019-03-20 | 2022-11-02 | Zeon Corporation | SEALING MATERIAL FOR ELECTROCHEMICAL DEVICE AND SEALING MATERIAL COMPOSITION |
EP3943569A4 (en) * | 2019-03-20 | 2022-11-02 | Zeon Corporation | SEALANT FOR ELECTROCHEMICAL DEVICE AND SEALANT COMPOSITION |
US11884805B2 (en) | 2019-03-20 | 2024-01-30 | Zeon Corporation | Sealant and sealant composition for electrochemical device |
KR20230028259A (ko) | 2020-06-30 | 2023-02-28 | 니폰 제온 가부시키가이샤 | 비수 전해액 전지용 시일제, 비수 전해액 전지용 시일제 조성물, 및 비수 전해액 전지 |
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