CA2754372A1 - Positive-electrode material for lithium-ion secondary battery and method of producing same - Google Patents
Positive-electrode material for lithium-ion secondary battery and method of producing same Download PDFInfo
- Publication number
- CA2754372A1 CA2754372A1 CA2754372A CA2754372A CA2754372A1 CA 2754372 A1 CA2754372 A1 CA 2754372A1 CA 2754372 A CA2754372 A CA 2754372A CA 2754372 A CA2754372 A CA 2754372A CA 2754372 A1 CA2754372 A1 CA 2754372A1
- Authority
- CA
- Canada
- Prior art keywords
- lithium
- positive
- secondary battery
- carbon
- 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.)
- Abandoned
Links
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 229910001416 lithium ion Inorganic materials 0.000 title claims abstract description 49
- 239000007774 positive electrode material Substances 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 title claims description 30
- 239000003575 carbonaceous material Substances 0.000 claims abstract description 81
- 239000000835 fiber Substances 0.000 claims abstract description 48
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 44
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 39
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 39
- 229910001463 metal phosphate Inorganic materials 0.000 claims abstract description 30
- 239000006229 carbon black Substances 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- GELKBWJHTRAYNV-UHFFFAOYSA-K lithium iron phosphate Chemical compound [Li+].[Fe+2].[O-]P([O-])([O-])=O GELKBWJHTRAYNV-UHFFFAOYSA-K 0.000 claims abstract description 17
- 229910021389 graphene Inorganic materials 0.000 claims abstract description 10
- 229910003481 amorphous carbon Inorganic materials 0.000 claims abstract description 6
- 239000002041 carbon nanotube Substances 0.000 claims description 22
- 229910021393 carbon nanotube Inorganic materials 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 18
- 238000002156 mixing Methods 0.000 claims description 17
- -1 oxysilicate Chemical compound 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 230000006835 compression Effects 0.000 claims description 9
- 238000007906 compression Methods 0.000 claims description 9
- 229910052723 transition metal Inorganic materials 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 7
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 7
- 150000003624 transition metals Chemical class 0.000 claims description 6
- 239000011248 coating agent Substances 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 239000002134 carbon nanofiber Substances 0.000 claims description 3
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 229910052785 arsenic Inorganic materials 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- DWYMPOCYEZONEA-UHFFFAOYSA-L fluoridophosphate Chemical compound [O-]P([O-])(F)=O DWYMPOCYEZONEA-UHFFFAOYSA-L 0.000 claims description 2
- 229910052732 germanium Inorganic materials 0.000 claims description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052748 manganese Inorganic materials 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 229910052758 niobium Inorganic materials 0.000 claims description 2
- 229910052755 nonmetal Inorganic materials 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000002131 composite material Substances 0.000 claims 5
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims 1
- 239000002245 particle Substances 0.000 description 20
- 239000013543 active substance Substances 0.000 description 18
- 238000012360 testing method Methods 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 9
- 239000006230 acetylene black Substances 0.000 description 8
- 239000011888 foil Substances 0.000 description 8
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- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 239000004020 conductor Substances 0.000 description 6
- 239000011267 electrode slurry Substances 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 229910052493 LiFePO4 Inorganic materials 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- 239000003792 electrolyte Substances 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000007773 negative electrode material Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- 230000005611 electricity Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 239000011247 coating layer Substances 0.000 description 3
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 229910003002 lithium salt Inorganic materials 0.000 description 3
- 159000000002 lithium salts Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 239000003273 ketjen black Substances 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 239000011255 nonaqueous electrolyte Substances 0.000 description 2
- 229920000620 organic polymer Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 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
- 239000011163 secondary particle Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910011279 LiCoPO4 Inorganic materials 0.000 description 1
- 229910010740 LiFeSiO4 Inorganic materials 0.000 description 1
- 229910000668 LiMnPO4 Inorganic materials 0.000 description 1
- 229910001290 LiPF6 Inorganic materials 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 229920002544 Olefin fiber Polymers 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 229910021386 carbon form Inorganic materials 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 239000002322 conducting polymer Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000011889 copper foil Substances 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 210000001787 dendrite Anatomy 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229920001973 fluoroelastomer Polymers 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 239000007770 graphite material Substances 0.000 description 1
- 239000012784 inorganic fiber Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910021450 lithium metal oxide Inorganic materials 0.000 description 1
- MCVFFRWZNYZUIJ-UHFFFAOYSA-M lithium;trifluoromethanesulfonate Chemical compound [Li+].[O-]S(=O)(=O)C(F)(F)F MCVFFRWZNYZUIJ-UHFFFAOYSA-M 0.000 description 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000004767 olefin fiber Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000007581 slurry coating method Methods 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
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- 229910052905 tridymite Inorganic materials 0.000 description 1
Classifications
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- H—ELECTRICITY
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- H01M4/36—Selection of substances as active materials, active masses, active liquids
- H01M4/58—Selection of substances as active materials, active masses, active liquids of inorganic compounds other than oxides or hydroxides, e.g. sulfides, selenides, tellurides, halogenides or LiCoFy; of polyanionic structures, e.g. phosphates, silicates or borates
- H01M4/5825—Oxygenated metallic salts or polyanionic structures, e.g. borates, phosphates, silicates, olivines
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- H01M4/485—Selection of substances as active materials, active masses, active liquids of inorganic oxides or hydroxides of mixed oxides or hydroxides for inserting or intercalating light metals, e.g. LiTi2O4 or LiTi2OxFy
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- H01M4/50—Selection of substances as active materials, active masses, active liquids of inorganic oxides or hydroxides of manganese
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- H01M4/52—Selection of substances as active materials, active masses, active liquids of inorganic oxides or hydroxides of nickel, cobalt or iron
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- H01M2220/20—Batteries in motive systems, e.g. vehicle, ship, plane
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- 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
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- 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
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
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Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2754372A CA2754372A1 (en) | 2011-10-04 | 2011-10-04 | Positive-electrode material for lithium-ion secondary battery and method of producing same |
| CN201280048742.0A CN103918109B (zh) | 2011-10-04 | 2012-10-04 | 正电极材料:用于其制备并在锂二次电池中使用的方法 |
| CN201810283179.4A CN108511674B (zh) | 2011-10-04 | 2012-10-04 | 正电极材料:用于其制备并在锂二次电池中使用的方法 |
| EP12839054.9A EP2764564B1 (en) | 2011-10-04 | 2012-10-04 | Positive-electrode materials: methods for their preparation and use in lithium secondary batteries |
| US14/349,076 US9577253B2 (en) | 2011-10-04 | 2012-10-04 | Positive-electrode materials: methods for their preparation and use in lithium secondary batteries |
| PCT/CA2012/050702 WO2013049939A1 (en) | 2011-10-04 | 2012-10-04 | Positive-electrode materials: methods for their preparation and use in lithium secondary batteries |
| ES12839054.9T ES2674334T3 (es) | 2011-10-04 | 2012-10-04 | Materiales de electrodo positivo: métodos para su preparación y su uso en baterías de litio secundarias |
| KR1020147010971A KR102000579B1 (ko) | 2011-10-04 | 2012-10-04 | 양전극 소재: 이의 제조방법 및 리튬 2차 배터리에서의 용도 |
| CA2849008A CA2849008C (en) | 2011-10-04 | 2012-10-04 | Positive-electrode materials: methods for their preparation and use in lithium secondary batteries |
| JP2014533746A JP6321541B2 (ja) | 2011-10-04 | 2012-10-04 | 正電極材料、その製造方法およびリチウム二次電池における使用 |
| US15/405,662 US10090525B2 (en) | 2011-10-04 | 2017-01-13 | Positive-electrode materials: methods for their preparation and use in lithium secondary batteries |
| US15/997,910 US10944107B2 (en) | 2011-10-04 | 2018-06-05 | Methods for the preparation and use of positive electrode materials coated with carbon in lithium secondary batteries |
| US17/096,403 US11715828B2 (en) | 2011-10-04 | 2020-11-12 | Positive-electrode materials: methods for their preparation and use in lithium secondary batteries |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA2754372A CA2754372A1 (en) | 2011-10-04 | 2011-10-04 | Positive-electrode material for lithium-ion secondary battery and method of producing same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2754372A1 true CA2754372A1 (en) | 2013-04-04 |
Family
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2754372A Abandoned CA2754372A1 (en) | 2011-10-04 | 2011-10-04 | Positive-electrode material for lithium-ion secondary battery and method of producing same |
| CA2849008A Active CA2849008C (en) | 2011-10-04 | 2012-10-04 | Positive-electrode materials: methods for their preparation and use in lithium secondary batteries |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2849008A Active CA2849008C (en) | 2011-10-04 | 2012-10-04 | Positive-electrode materials: methods for their preparation and use in lithium secondary batteries |
Country Status (8)
| Country | Link |
|---|---|
| US (4) | US9577253B2 (https=) |
| EP (1) | EP2764564B1 (https=) |
| JP (1) | JP6321541B2 (https=) |
| KR (1) | KR102000579B1 (https=) |
| CN (2) | CN108511674B (https=) |
| CA (2) | CA2754372A1 (https=) |
| ES (1) | ES2674334T3 (https=) |
| WO (1) | WO2013049939A1 (https=) |
Cited By (3)
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|---|---|---|---|---|
| WO2013166598A1 (en) * | 2012-05-08 | 2013-11-14 | HYDRO-QUéBEC | Lithium-ion secondary battery and method of producing same |
| US11043680B2 (en) * | 2013-11-13 | 2021-06-22 | Showa Denko K.K. | Electrode material including small diameter, carbon nanotubes bridging large diameter carbon nanotubes, redox flow battery electrode, redox flow battery, and method for producing electrode material |
| CN120674480A (zh) * | 2025-08-19 | 2025-09-19 | 湖北万润新能源科技股份有限公司 | 一种复合磷酸铁锂材料及其制备方法、正极极片和二次电池 |
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-
2011
- 2011-10-04 CA CA2754372A patent/CA2754372A1/en not_active Abandoned
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2012
- 2012-10-04 KR KR1020147010971A patent/KR102000579B1/ko active Active
- 2012-10-04 US US14/349,076 patent/US9577253B2/en active Active
- 2012-10-04 JP JP2014533746A patent/JP6321541B2/ja active Active
- 2012-10-04 CN CN201810283179.4A patent/CN108511674B/zh active Active
- 2012-10-04 CA CA2849008A patent/CA2849008C/en active Active
- 2012-10-04 CN CN201280048742.0A patent/CN103918109B/zh active Active
- 2012-10-04 EP EP12839054.9A patent/EP2764564B1/en active Active
- 2012-10-04 ES ES12839054.9T patent/ES2674334T3/es active Active
- 2012-10-04 WO PCT/CA2012/050702 patent/WO2013049939A1/en not_active Ceased
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2017
- 2017-01-13 US US15/405,662 patent/US10090525B2/en active Active
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2018
- 2018-06-05 US US15/997,910 patent/US10944107B2/en active Active
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2020
- 2020-11-12 US US17/096,403 patent/US11715828B2/en active Active
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013166598A1 (en) * | 2012-05-08 | 2013-11-14 | HYDRO-QUéBEC | Lithium-ion secondary battery and method of producing same |
| US10050270B2 (en) | 2012-05-08 | 2018-08-14 | Hydro-Quebec | Lithium-ion secondary battery and method of producing same |
| USRE49319E1 (en) | 2012-05-08 | 2022-11-29 | Hydro-Quebec | Lithium-ion secondary battery and method of producing same |
| US11043680B2 (en) * | 2013-11-13 | 2021-06-22 | Showa Denko K.K. | Electrode material including small diameter, carbon nanotubes bridging large diameter carbon nanotubes, redox flow battery electrode, redox flow battery, and method for producing electrode material |
| CN120674480A (zh) * | 2025-08-19 | 2025-09-19 | 湖北万润新能源科技股份有限公司 | 一种复合磷酸铁锂材料及其制备方法、正极极片和二次电池 |
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| ES2674334T3 (es) | 2018-06-28 |
| US20150037673A1 (en) | 2015-02-05 |
| CN108511674A (zh) | 2018-09-07 |
| CN108511674B (zh) | 2022-06-03 |
| CN103918109A (zh) | 2014-07-09 |
| US11715828B2 (en) | 2023-08-01 |
| EP2764564A4 (en) | 2015-07-01 |
| CN103918109B (zh) | 2018-05-01 |
| US9577253B2 (en) | 2017-02-21 |
| JP6321541B2 (ja) | 2018-05-09 |
| CA2849008A1 (en) | 2013-04-11 |
| CA2849008C (en) | 2021-01-12 |
| US10090525B2 (en) | 2018-10-02 |
| KR20140082988A (ko) | 2014-07-03 |
| WO2013049939A1 (en) | 2013-04-11 |
| JP2014532263A (ja) | 2014-12-04 |
| US20210066718A1 (en) | 2021-03-04 |
| KR102000579B1 (ko) | 2019-07-16 |
| EP2764564B1 (en) | 2018-04-25 |
| US20180287155A1 (en) | 2018-10-04 |
| US20170125813A1 (en) | 2017-05-04 |
| US10944107B2 (en) | 2021-03-09 |
| EP2764564A1 (en) | 2014-08-13 |
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