WO2023074967A1 - 분리막용 공중합체 및 이를 포함하는 이차전지 - Google Patents
분리막용 공중합체 및 이를 포함하는 이차전지 Download PDFInfo
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- WO2023074967A1 WO2023074967A1 PCT/KR2021/015438 KR2021015438W WO2023074967A1 WO 2023074967 A1 WO2023074967 A1 WO 2023074967A1 KR 2021015438 W KR2021015438 W KR 2021015438W WO 2023074967 A1 WO2023074967 A1 WO 2023074967A1
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- Prior art keywords
- copolymer
- weight
- separator
- formula
- based monomer
- Prior art date
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- 229920001577 copolymer Polymers 0.000 title claims abstract description 53
- 239000000178 monomer Substances 0.000 claims abstract description 49
- 239000000203 mixture Substances 0.000 claims abstract description 31
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 22
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 21
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000002002 slurry Substances 0.000 claims abstract description 19
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 7
- 239000010954 inorganic particle Substances 0.000 claims description 25
- 239000012528 membrane Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 229920001400 block copolymer Polymers 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229920005604 random copolymer Polymers 0.000 claims description 2
- 230000000052 comparative effect Effects 0.000 description 21
- 238000000576 coating method Methods 0.000 description 17
- 239000000758 substrate Substances 0.000 description 17
- -1 hydroxyl methyl Chemical group 0.000 description 16
- 239000011248 coating agent Substances 0.000 description 15
- 229920000642 polymer Polymers 0.000 description 12
- 229920000098 polyolefin Polymers 0.000 description 12
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
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- 238000002360 preparation method Methods 0.000 description 10
- 229910052744 lithium Inorganic materials 0.000 description 9
- 238000000034 method Methods 0.000 description 9
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- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 6
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- 239000002202 Polyethylene glycol Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
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- 150000002894 organic compounds Chemical class 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
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- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
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- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 2
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- 239000004743 Polypropylene Substances 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 239000006183 anode active material Substances 0.000 description 2
- 238000000498 ball milling Methods 0.000 description 2
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- 239000002131 composite material Substances 0.000 description 2
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- 238000007607 die coating method Methods 0.000 description 2
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- VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
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- 239000012212 insulator Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229910001416 lithium ion Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 229960004418 trolamine Drugs 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- YQIGLEFUZMIVHU-UHFFFAOYSA-N 2-methyl-n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C(C)=C YQIGLEFUZMIVHU-UHFFFAOYSA-N 0.000 description 1
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 229910002706 AlOOH Inorganic materials 0.000 description 1
- 229910017008 AsF 6 Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- AOJOLMNMKPYSHD-UHFFFAOYSA-N C(CCC)NC(C(=C)C)=O.C(C(=C)C)(=O)NCCCC Chemical compound C(CCC)NC(C(=C)C)=O.C(C(=C)C)(=O)NCCCC AOJOLMNMKPYSHD-UHFFFAOYSA-N 0.000 description 1
- 229910020366 ClO 4 Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910000881 Cu alloy Inorganic materials 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 229910018119 Li 3 PO 4 Inorganic materials 0.000 description 1
- 229910000733 Li alloy Inorganic materials 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- 229910002367 SrTiO Inorganic materials 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- GEIAQOFPUVMAGM-UHFFFAOYSA-N ZrO Inorganic materials [Zr]=O GEIAQOFPUVMAGM-UHFFFAOYSA-N 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- SOGAXMICEFXMKE-UHFFFAOYSA-N alpha-Methyl-n-butyl acrylate Natural products CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KFKPWTFHOVSSSI-UHFFFAOYSA-N butyl 2-hydroxyprop-2-enoate Chemical compound CCCCOC(=O)C(O)=C KFKPWTFHOVSSSI-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000006255 coating slurry Substances 0.000 description 1
- CKFRRHLHAJZIIN-UHFFFAOYSA-N cobalt lithium Chemical compound [Li].[Co] CKFRRHLHAJZIIN-UHFFFAOYSA-N 0.000 description 1
- 229910000428 cobalt oxide Inorganic materials 0.000 description 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 210000001787 dendrite Anatomy 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 238000007603 infrared drying Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000002687 intercalation Effects 0.000 description 1
- 238000009830 intercalation Methods 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000001989 lithium alloy Substances 0.000 description 1
- 229910002102 lithium manganese oxide Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- VLXXBCXTUVRROQ-UHFFFAOYSA-N lithium;oxido-oxo-(oxomanganiooxy)manganese Chemical compound [Li+].[O-][Mn](=O)O[Mn]=O VLXXBCXTUVRROQ-UHFFFAOYSA-N 0.000 description 1
- URIIGZKXFBNRAU-UHFFFAOYSA-N lithium;oxonickel Chemical compound [Li].[Ni]=O URIIGZKXFBNRAU-UHFFFAOYSA-N 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- YRVUCYWJQFRCOB-UHFFFAOYSA-N n-butylprop-2-enamide Chemical compound CCCCNC(=O)C=C YRVUCYWJQFRCOB-UHFFFAOYSA-N 0.000 description 1
- ZIWDVJPPVMGJGR-UHFFFAOYSA-N n-ethyl-2-methylprop-2-enamide Chemical compound CCNC(=O)C(C)=C ZIWDVJPPVMGJGR-UHFFFAOYSA-N 0.000 description 1
- SWPMNMYLORDLJE-UHFFFAOYSA-N n-ethylprop-2-enamide Chemical compound CCNC(=O)C=C SWPMNMYLORDLJE-UHFFFAOYSA-N 0.000 description 1
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 description 1
- WDFKEEALECCKTJ-UHFFFAOYSA-N n-propylprop-2-enamide Chemical compound CCCNC(=O)C=C WDFKEEALECCKTJ-UHFFFAOYSA-N 0.000 description 1
- QQZXAODFGRZKJT-UHFFFAOYSA-N n-tert-butyl-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NC(C)(C)C QQZXAODFGRZKJT-UHFFFAOYSA-N 0.000 description 1
- XFHJDMUEHUHAJW-UHFFFAOYSA-N n-tert-butylprop-2-enamide Chemical compound CC(C)(C)NC(=O)C=C XFHJDMUEHUHAJW-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000002006 petroleum coke Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000007774 positive electrode material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- OGOBWYZAVILZEC-UHFFFAOYSA-N propyl 2-hydroxyprop-2-enoate Chemical compound CCCOC(=O)C(O)=C OGOBWYZAVILZEC-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M50/00—Constructional details or processes of manufacture of the non-active parts of electrochemical cells other than fuel cells, e.g. hybrid cells
- H01M50/40—Separators; Membranes; Diaphragms; Spacing elements inside cells
- H01M50/409—Separators, membranes or diaphragms characterised by the material
- H01M50/411—Organic material
- H01M50/414—Synthetic resins, e.g. thermoplastics or thermosetting resins
- H01M50/42—Acrylic resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/56—Acrylamide; Methacrylamide
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/24—Homopolymers or copolymers of amides or imides
- C09D133/26—Homopolymers or copolymers of acrylamide or methacrylamide
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M50/00—Constructional details or processes of manufacture of the non-active parts of electrochemical cells other than fuel cells, e.g. hybrid cells
- H01M50/40—Separators; Membranes; Diaphragms; Spacing elements inside cells
- H01M50/409—Separators, membranes or diaphragms characterised by the material
- H01M50/411—Organic material
- H01M50/414—Synthetic resins, e.g. thermoplastics or thermosetting resins
- H01M50/423—Polyamide resins
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M50/00—Constructional details or processes of manufacture of the non-active parts of electrochemical cells other than fuel cells, e.g. hybrid cells
- H01M50/40—Separators; Membranes; Diaphragms; Spacing elements inside cells
- H01M50/409—Separators, membranes or diaphragms characterised by the material
- H01M50/443—Particulate material
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M50/00—Constructional details or processes of manufacture of the non-active parts of electrochemical cells other than fuel cells, e.g. hybrid cells
- H01M50/40—Separators; Membranes; Diaphragms; Spacing elements inside cells
- H01M50/409—Separators, membranes or diaphragms characterised by the material
- H01M50/446—Composite material consisting of a mixture of organic and inorganic materials
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M50/00—Constructional details or processes of manufacture of the non-active parts of electrochemical cells other than fuel cells, e.g. hybrid cells
- H01M50/40—Separators; Membranes; Diaphragms; Spacing elements inside cells
- H01M50/409—Separators, membranes or diaphragms characterised by the material
- H01M50/449—Separators, membranes or diaphragms characterised by the material having a layered structure
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M50/00—Constructional details or processes of manufacture of the non-active parts of electrochemical cells other than fuel cells, e.g. hybrid cells
- H01M50/40—Separators; Membranes; Diaphragms; Spacing elements inside cells
- H01M50/489—Separators, membranes, diaphragms or spacing elements inside the cells, characterised by their physical properties, e.g. swelling degree, hydrophilicity or shut down properties
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2227—Oxides; Hydroxides of metals of aluminium
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- 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
Definitions
- the present invention relates to a copolymer and a slurry composition containing the copolymer, a separator and a secondary battery.
- Lithium secondary batteries are widely used in the electric, electronic, communication and computer industries due to their high energy density, and their application fields are expanding to high-capacity secondary batteries such as hybrid vehicles and electric vehicles following small lithium secondary batteries for portable electronic devices. there is.
- lithium ion secondary batteries are insulated by separators, it is very important to secure the thermal/chemical safety of separators because there is a possibility of heat generation and explosion due to a short circuit between the positive and negative electrodes due to internal or external battery abnormalities or shocks. .
- polyolefin-based films are widely used as separators, but polyolefins suffer from severe heat shrinkage at high temperatures and poor mechanical properties.
- inorganic particles are coated on one side or both sides of the porous separator substrate together with a binder, giving the inorganic particles the ability to suppress the shrinkage rate of the substrate.
- a safer separator can be manufactured by the coating layer.
- the coating layer In order to secure excellent battery characteristics, the coating layer must be uniformly coated and at the same time, strong adhesion to the substrate is required.
- Patent Document 1 Republic of Korea Patent Registration No. 10-1430975
- Patent Document 2 Republic of Korea Patent Publication No. 10-2006-0072065
- an object of the present invention is to provide a slurry composition having excellent heat resistance or adhesiveness using a copolymer.
- the present invention is to provide a separator having excellent heat resistance to which the slurry composition is applied and a battery having excellent performance using the separator.
- hydroxyl groups comprising acrylate-based monomer units, greater than 80% by weight and less than 95% by weight of acrylamide-based monomer units and greater than 0% by weight and less than 15% by weight of acrylic acid-based monomer units
- a copolymer is provided.
- a slurry composition is provided.
- Another aspect of the present application comprising the slurry composition
- a separator is provided.
- Another aspect of the present application including the separation membrane,
- a secondary battery is provided.
- the copolymer of the present invention can improve the dispersion stability of the slurry composition, increase the adhesion with the polyolefin film, which is the separator substrate, and improve the heat resistance of the separator.
- based on 100% by weight of the total copolymer weight more than 0% by weight and less than 15% by weight of acrylonitrile-based monomer units, more than 0% by weight and less than 5% by weight of hydroxyl groups (—OH ), an acrylamide-based monomer unit of more than 80% by weight and less than 95% by weight of an acrylamide-based monomer unit including ), and an acrylic acid-based monomer unit of more than 0% by weight and less than 15% by weight.
- the acrylonitrile-based monomer may be, for example, at least one selected from the group consisting of acrylonitrile and methacrylonitrile, but is not limited thereto.
- the acrylate-based monomer containing the hydroxyl group (-OH) is, for example, hydroxyl methyl acrylate, hydroxyl methyl methacrylate, hydroxyl ethyl acrylate acrylate), hydroxyl ethyl methacrylate, hydroxyl propyl acrylate, hydroxyl propyl methacrylate, hydroxyl isopropyl acrylate, hydroxyl isopropyl methacrylate, hydroxyl butyl acrylate, hydroxyl butyl methacrylate, hydroxyl sec-butyl acrylate , hydroxyl sec-butyl methacrylate, hydroxyl tert-butyl acrylate, hydroxyl tert-butyl methacrylate and polyethylene glycol It may be any one or more selected from the group consisting of methacrylate (polyethyleneglycol methacrylate), but is not limited thereto.
- the acrylamide-based monomer units include, for example, acrylamide, methacrylamide, N-ethyl acrylamide, N-ethyl methacrylamide, N- Propyl acrylamide, N-isopropyl acrylamide, N-isopropyl methacrylamide, N-butyl acrylamide, N -Butyl methacrylamide (N-butyl methacrylamide), N-sec-butyl acrylamide (N-sec-butyl acrylamide), N-sec-butyl methacrylamide (N-sec-butyl methacrylamide). It may be at least one selected from the group consisting of N-tert-butyl acrylamide and N-tert-butyl methacrylamide, but is not limited thereto.
- the acrylic acid-based monomer unit may be, for example, at least one selected from the group consisting of acrylic acid and methacrylic acid, but is not limited thereto.
- the degree of crosslinking may be increased and the heat resistance may be improved. If the % is exceeded, the viscosity becomes extremely high, which may cause a problem in coating fairness.
- the cyano group of the acrylonitrile-based monomer can improve adhesive strength and heat resistance. In addition, electrical resistance can be lowered due to the high ionic conductivity of the cyano group.
- both adhesive strength and heat resistance may be reduced while the extent of improvement in adhesive strength and heat resistance is greatly reduced.
- the copolymer may be represented by Formula 1 below.
- R 1 to R 3 are each independently hydrogen, a linear or branched hydrocarbon having 1 to 4 carbon atoms,
- M is at least one selected from the group consisting of alkali metals, secondary amines and tertiary amines,
- n is an integer from 0 to 500;
- m, l, x and y in Formula 1 correspond to the mole fraction of each monomer unit, and the sum of the mole fractions of each monomer unit is 1.
- R 1 to R 3 may each independently include one or more selected from the group consisting of hydrogen, methyl, and ethyl.
- M in Chemical Formula 1 is an alkali metal, it may be Li, Na or K, but is not limited thereto.
- M in Formula 1 is any one selected from the group consisting of secondary amines and tertiary amines, it may be included in an amount of 0.05 to 0.4 parts by weight based on 100 parts by weight of the copolymer.
- M in Formula 1 may include at least one selected from the group consisting of compounds represented by Formulas 2 to 5 below.
- R 4 to R 6 are each independently a linear or branched hydrocarbon having 1 to 6 carbon atoms.
- L 1 to L 3 are each independently an alkylene group having 1 to 6 carbon atoms
- a to c are each independently an integer of 0 to 2;
- the copolymer may be a random or block copolymer depending on the synthesis process.
- the copolymer may have a number average molecular weight of 5,000 to 1,000,000.
- the fluidity of the copolymer may increase, resulting in deterioration in dispersibility and deterioration in heat resistance of the separator. If the number average molecular weight is 1,000,000 or more, the viscosity is too high for use and the pores of the separator may be blocked, reducing air permeability and resistance.
- a slurry composition according to another aspect of the present disclosure may include the copolymer and inorganic particles.
- the adhesive strength of the slurry composition may be 80 to 86 gf/mm.
- the inorganic particles may be used without limitation as long as they are insulator particles, and preferably may be high dielectric constant insulator particles.
- the inorganic particles include Al 2 O 3 , AlOOH, SiO 2 , TiO 2 , ZrO 2 , ZnO, NiO, CaO, SnO 2 , Y 2 O 3 , MgO, BaTiO 3 , CaTiO 3 , SrTiO 3 , SiC , Li 3 PO 4 , Pb(Zr,Ti)O 3 (PZT), (Pb,La)(Zr,Ti)O 3 (PLZT), and mixtures thereof.
- the inorganic particles are not particularly limited in size, but may have, for example, an average particle diameter of 0.01 ⁇ m to 30 ⁇ m, more preferably 0.1 ⁇ m to 10 ⁇ m.
- an average particle diameter of the inorganic particles is less than the above preferred range, dispersibility may be lowered, and when the average particle diameter exceeds the above preferred range, the thickness of the coating layer becomes thick after coating, and mechanical properties may be deteriorated.
- the shape of the inorganic particles is not particularly limited, and may be, for example, spherical, elliptical, or irregular.
- a separator according to another aspect of the present disclosure may include the slurry composition.
- Electrical resistance of the separator may be 0.7 to 0.76 m ⁇ .
- thermal contraction rate of the separator may be 5% or less in both MD (Machine Direction, longitudinal direction) and TD (Transverse Direction, width direction) directions.
- a separator may be prepared by coating the slurry composition on at least one surface of a porous substrate film or by preparing the slurry composition in the form of a film and laminating it to the porous substrate film.
- the separator may be used as a separator for a secondary battery, for example, a separator for a lithium secondary battery.
- a separator As an example of manufacturing a separator, (a) preparing a polymer solution by dissolving or dispersing the copolymer in a solvent; (b) adding and mixing inorganic particles to the polymer solution of step a); and (c) coating and drying at least one region selected from the group consisting of the surface of the polyolefin-based separator substrate and a portion of pores in the substrate with the mixture of step b).
- the copolymer is prepared and prepared in the form of a polymer solution in which the copolymer is dissolved or dispersed in an appropriate solvent.
- the solubility index is similar to that of the copolymer used as the binder and has a low boiling point. This is to facilitate uniform mixing and subsequent solvent removal.
- usable solvents include acetone, tetrahydrofuran, methylene chloride, chloroform, dimethylformamide, N-methyl-2-pyrrolidone ( N-methyl-2-pyrrolidone (NMP), cyclohexane, water or mixtures thereof. More preferably, it can be used in a water-dispersed state.
- a mixture of inorganic particles and polymer is prepared by adding and dispersing inorganic particles in the prepared polymer solution.
- the dispersion time may be 1 to 50 hours.
- a conventional method may be used, and a ball mill method is particularly preferable.
- composition of the mixture composed of inorganic particles and polymers is not particularly limited, but accordingly, the thickness, pore size, and porosity of the finally manufactured organic/inorganic composite porous separator of the present invention can be adjusted.
- the separator of the present invention can be obtained by coating the prepared mixture of inorganic particles and polymer on the prepared polyolefin-based separator substrate and then drying.
- a method of coating a mixture of inorganic particles and a polymer on a polyolefin-based separator substrate conventional coating methods known in the art may be used, for example, dip coating, die coating, and roll coating. ) coating, comma coating, or a combination of these methods may be used.
- coating a mixture of inorganic particles and a polymer on a polyolefin-based separator substrate it can be applied to both sides of the separator substrate or selectively applied to only one surface.
- lithium ions can be transferred not only through the separator substrate but also through the porous active layer, and when an internal short circuit occurs due to an external impact, the above-described safety improvement effect can be exhibited. .
- the secondary battery may include a positive electrode, a negative electrode, the separator interposed between the positive electrode and the negative electrode, and an electrolyte solution.
- the secondary battery may be manufactured according to a conventional method known in the art.
- the secondary battery is manufactured by assembling the electrode and the separator interposed therebetween, and then injecting an electrolyte solution into the assembly.
- the electrode to be applied together with the separator is not particularly limited, but a typical cathode active material that can be used for a cathode of a secondary battery can be used as the cathode active material, and non-limiting examples thereof include lithium manganese oxide and lithium cobalt. and a lithium intercalation material, such as a lithiated cobalt oxide, a lithium nickel oxide, or a composite oxide formed by a combination thereof.
- the anode active material may be a conventional anode active material that can be used for a cathode of a conventional electrochemical device, and non-limiting examples thereof include lithium metal, lithium alloy and carbon, petroleum coke, and lithium adsorption materials such as activated carbon, graphite, or other carbons.
- Each of the positive electrode active materials described above is prepared by a cathode current collector, that is, a foil made of aluminum, nickel or a combination thereof, and a cathode current collector, that is, copper, gold, nickel, or a copper alloy or a combination thereof. Both electrodes are formed in the form of being bound to a foil.
- the electrolyte solution is a salt having the same structure as A+B-, wherein A+ includes an alkali metal cation such as Li + , Na + , or K + or an ion composed of a combination thereof, and B- includes PF 6 - , BF 4 - , Cl - , Br - , I - , ClO 4 - , AsF 6 - , CH 3 CO 2 - , CF 3 SO 3 - , N(CF 3 SO 2 ) 2 - , C(CF 2 SO 2 ) 3 - and Salts containing ions of the same anion or combinations thereof are propylene carbonate (PC), ethylene carbonate (EC), diethyl carbonate (DEC), and dimethyl carbonate (DMC).
- PC propylene carbonate
- EC ethylene carbonate
- DEC diethyl carbonate
- DMC dimethyl carbonate
- dipropyl carbonate DPC
- dimethyl sulfoxide acetonitrile
- dimethoxyethane diethoxyethane
- tetrahydrofuran N-methyl-
- organic solvent consisting of 2-pyrrolidone (N-methyl-2-pyrrolidone, NMP), ethyl methyl carbonate (EMC), gamma butyrolactone (GBL) or a mixture thereof do.
- lamination and folding processes of the separator and the electrode may be performed in addition to winding, which is a general process.
- An inorganic coating layer is formed by applying the porous membrane coating slurry prepared in Preparation Example 2 to a polyolefin porous substrate (polyethylene (PE), polypropylene (PP), etc.).
- a coating method various methods such as dip coating, die coating, gravure coating, and comma coating may be used.
- the thickness of the inorganic coating layer was 0.5 to 6 ⁇ m on one side or both sides, and when the thickness was less than 0.5 ⁇ m, the heat resistance of the separator significantly decreased, and when the thickness exceeded 6 ⁇ m, the thickness of the separator was too thick. could decrease the energy density of and increase the resistance.
- Examples 1 to 3 and Comparative Examples 1 to 5 were prepared according to Preparation Example 1 by adjusting the composition ratio of the monomers and the content of the amine-based organic compound as shown in Table 1 below.
- the monomers used are acrylamide (AM) as an acrylamide-based monomer, acrylonitrile (AN) as an acrylonitrile-based monomer, acrylic acid (AA) as an acrylic acid-based monomer unit, and hydroxyl group (-OH).
- AM acrylamide
- AN acrylonitrile
- AA acrylic acid-based monomer unit
- -OH hydroxyl group
- PEGMA polyethylene glycol methacrylate
- HEMA hydroxyethyl methacrylate
- the amine-based organic compound used was triethanol amine (TA), and 0.2 parts by weight was added based on 100 parts by weight of the copolymer.
- TA triethanol amine
- the separator prepared according to Preparation Example 3 using the binder copolymers of Examples 1 to 3 and Comparative Examples 1 to 5 was cut to a size of 18 mm in width and 100 mm in length.
- a double-sided tape having a width of 20 mm and a length of 40 mm was attached to an acrylic plate having an area of 40 mm in width and 100 mm in length. After attaching the prepared separator on the double-sided tape, it was lightly pressed 5 times with a hand roller. Mount the specimen prepared above in a UTM (20kgf Load Cell), fix one part of the membrane to the upper clip of the tensile strength machine and the tape attached to one side of the membrane to the lower clip, and measure the 180° peel strength at a speed of 100mm/min did Five or more specimens per sample were prepared and measured, and the average value was calculated.
- UTM (20kgf Load Cell
- the separator prepared according to Preparation Example 3 using the binder copolymers of Examples 1 to 3 and Comparative Examples 1 to 5 was prepared as a sample having a horizontal and vertical size of 5 ⁇ 5 cm, and the sample was heated in an oven at 150 ° C. After leaving it for 1 hour, the shrinkage rate was measured.
- a coin cell type electrode assembly was prepared by using the binder copolymers of Examples 1 to 3 and Comparative Examples 1 to 5 through the separator prepared according to Preparation Example 3, a lithium metal, and a SUS plate, respectively. did
- a lithium secondary battery was manufactured by injecting an electrolyte solution containing lithium salt into the prepared electrode assembly and sealing it.
- the manufactured battery was measured for impedance using an impedance analyzer, and the results are shown in Table 2 below.
- Example 3 in which HEMA having a much shorter chain was used in the same amount instead of PEGMA in Example 2, it was confirmed that the heat resistance of the separator was further improved because the crosslinking density was increased.
- Comparative Example 4 using a copolymer prepared using only acrylamide, acrylonitrile, and acrylic acid as monomers, a portion of acrylamide as a monomer containing a hydroxyl group while containing the same content of acrylonitrile and acrylic acid
- the electrical resistance of the separation membrane increased.
- the heat shrinkage rate of the separator increased and the heat resistance of the separator decreased.
- the separator prepared using the binder copolymers of Examples had excellent substrate adhesion and excellent heat resistance within 5% at 150 ° C.
- the copolymer of the present invention can improve the dispersion stability of the slurry composition, increase the adhesion with the polyolefin film, which is the separator substrate, and improve the heat resistance of the separator.
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- Inorganic Chemistry (AREA)
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Abstract
Description
구분 | 모노머 조성(중량%) | ||||
AM | AA | AN | PEGMA | HEMA | |
실시예 1 | 88 | 5 | 5 | 2 | 0 |
실시예 2 | 85 | 5 | 5 | 5 | 0 |
실시예 3 | 85 | 5 | 5 | 0 | 5 |
비교예 1 | 100 | 0 | 0 | 0 | 0 |
비교예 2 | 75 | 25 | 0 | 0 | 0 |
비교예 3 | 90 | 10 | 0 | 0 | 0 |
비교예 4 | 90 | 5 | 5 | 0 | 0 |
비교예 5 | 85 | 5 | 10 | 0 | 0 |
구분 | 물성 | ||
저항 [mΩ] |
접착력 [gf/mm] |
열수축률 (MD/TD) [%] |
|
실시예 1 | 0.76 | 84 | 4/4.5 |
실시예 2 | 0.72 | 83 | 3.5/4 |
실시예 3 | 0.7 | 85 | 3/3.5 |
비교예 1 | 0.87 | 6 | 3/3.5 |
비교예 2 | 0.67 | 8 | 26/38 |
비교예 3 | 0.77 | 7 | 7/8 |
비교예 4 | 0.78 | 87 | 6/6 |
비교예 5 | 0.76 | 78 | 6/6.5 |
Claims (9)
- 전체 공중합체 중량 100 중량%를 기준으로, 0 중량% 초과, 15 중량% 이하의 아크릴로나이트릴 계열의 단량체 단위, 0 중량% 초과, 5 중량% 이하의 수산기(-OH)를 포함하는 아크릴레이트 계열의 단량체 단위, 80 중량% 초과, 95 중량% 미만의 아크릴아마이드 계열의 단량체 단위 및 0 중량% 초과, 15 중량% 이하의 아크릴산 계열의 단량체 단위를 포함하는,공중합체.
- 제2항에 있어서,상기 화학식 1의 R1 내지 R3은 각각 독립적으로 수소, 메틸, 에틸로 이루어진 그룹에서 선택된 어느 하나 이상을 포함하는,공중합체.
- 제1항에 있어서,상기 공중합체는 랜덤 또는 블록 공중합체인,공중합체.
- 제1항에 있어서,상기 공중합체의 수평균 분자량이 5,000 ~ 1,000,000인,공중합체.
- 제1항 내지 제6항 중 어느 한 항의 공중합체; 및무기 입자;를 포함하는,슬러리 조성물.
- 제7항의 슬러리 조성물을 포함하는,분리막.
- 제8항의 분리막을 포함하는,이차전지.
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EP21962591.0A EP4242241A4 (en) | 2021-10-25 | 2021-10-29 | COPOLYMER FOR SEPARATOR, AND SECONDARY BATTERY COMPRISING IT |
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KR20200140637A (ko) * | 2019-06-07 | 2020-12-16 | 삼성에스디아이 주식회사 | 리튬 이차 전지용 분리막 및 이를 포함하는 리튬 이차 전지 |
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