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WO2003083973A1 - Électrolyte polymérique pour cellule électrochimique - Google Patents

Électrolyte polymérique pour cellule électrochimique Download PDF

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Publication number
WO2003083973A1
WO2003083973A1 PCT/US2003/008779 US0308779W WO03083973A1 WO 2003083973 A1 WO2003083973 A1 WO 2003083973A1 US 0308779 W US0308779 W US 0308779W WO 03083973 A1 WO03083973 A1 WO 03083973A1
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WO
WIPO (PCT)
Prior art keywords
poly
polymer electrolyte
polymer
ethylene oxide
electrolyte
Prior art date
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Ceased
Application number
PCT/US2003/008779
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English (en)
Inventor
Robert West
Qingzheng Wang
Khalil Amine
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Quallion LLC
Original Assignee
Quallion LLC
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from US10/104,352 external-priority patent/US20030180624A1/en
Priority claimed from US10/167,940 external-priority patent/US7498102B2/en
Application filed by Quallion LLC filed Critical Quallion LLC
Priority to US10/491,071 priority Critical patent/US20040214090A1/en
Priority to AU2003223327A priority patent/AU2003223327A1/en
Publication of WO2003083973A1 publication Critical patent/WO2003083973A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • 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
    • H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
    • H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
    • H01M10/0565—Polymeric materials, e.g. gel-type or solid-type
    • 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
    • H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
    • H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
    • H01M10/0566—Liquid materials
    • H01M10/0568—Liquid materials characterised by the solutes
    • 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
    • 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
    • H01G11/62—Liquid electrolytes characterised by the solute, e.g. salts, anions or cations therein
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M2300/00—Electrolytes
    • H01M2300/0017—Non-aqueous electrolytes
    • H01M2300/0065—Solid electrolytes
    • H01M2300/0082—Organic polymers
    • 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 electrolytes for rechargeable electrochemical cells, and, more particularly to cyclic siloxane polymer electrolytes with a poly(ethylene oxide) as a pendant group.
  • Polymer electrolytes have a number of advantages over the materials currently used in high-performance batteries. Compared to conventional batteries using heavy metals such as lead, nickel, and cadmium, the lithium-based polymer electrolyte batteries would be many times lighter. The proposed designs of these batteries would also allow them to be formed into various shapes besides the traditional cylindrical or rectangular shapes typical in regular batteries. ( See, Gray, F. M. Solid Polymer Electrolytes; VCH Publishers: New York, 1991, at 1-4, 5-21). These advantages have fueled commercial interests and research interests into improving the conductive properties of polymer electrolytes. Poly(ethylene oxide) (PEO) has been known to dissolve alkali metal salts and exhibit conductivity since the early 1970's. (See, Fenton, D. E.
  • the Si-O backbone of these polymers is highly flexible, yet retains its chemical and thermal integrity.
  • Polysiloxanes also have low glass transition temperatures, T g , and solvate lithium salts, making the polysiloxanes good candidates for potentially useful polymer electrolytes.
  • Carbonate solvents such as ethylene carbonate and propylene carbonate used for conventional lithium battery electrolytes, can easily bum with a source of ignition and generate flame, carbon dioxide, and hydrocarbons during thermal degradation.
  • carbonate solvents are easily reduced or oxidized at the surface of either the positive or the negative electrode, leading to an increase in impedance and capacity fade of the cell.
  • carbonate solvents used in lithium ion batteries react extremely exothermically with the charged electrode, potentially leading to thermal runaway of the battery.
  • the reactivity between the carbonate solvent and the electrodes become significant, especially when the battery is large, such as in the case of hybrid and electric vehicles, satellites, submarines, and load leveling facilities, as well as medical devices and consumer electronics.
  • Polymeric compounds however, have different combustion mechanisms than carbonates.
  • the initial stage of a fire occurs when a source of ignition decomposes the polymeric materials into flammable volatile products.
  • a source of ignition decomposes the polymeric materials into flammable volatile products.
  • the application of heat must be sufficient to decompose the polymer
  • the temperature must be sufficient to ignite the products of decomposition
  • the amount of heat transferred from the flame back to the polymer must be sufficient to maintain the cycle.
  • polymeric materials are more thermally stable than low molecular weight chemicals like carbonates because they are not volatile, and they vaporize at much higher temperatures.
  • Electrolytes based on polymeric structure have fundamentally better heat resistance than conventional carbonate based electrolytes and can reduce many side chemical reactions occurring in a lithium secondary battery under abnormal operating conditions such as temperatures exceeding 60°C.
  • the electrolytes with polymeric structure have advantages over carbonate solvent based electrolytes, their application in lithium secondary batteries as an ionic conducting medium has been limited due to low ionic conductivity, usually below 10 "5 S/cm at room temperature.
  • a liquid polymer electrolyte that does not evaporate at temperatures up to 150°C, or a solid polymer electrolyte with high conductivity is needed.
  • the new concept electrolytes described in this invention are ideal for lithium secondary batteries. They do not evaporate up to 150°C, offer high ionic conductivity of over 10 "4 S/cm around room temperature, and have a wide electrochemical stability window of over 4.5 V (vs. lithium).
  • the present inventors have developed a new type of metal ionic conductive electrolyte based on liquid cyclic poly(siloxane-g-ethylene oxide)s to overcome the above mentioned problems such as volatility, flammability and chemically reactivity in lithium batteries that are usually observed when using conventional carbonate based liquid electrolytes.
  • the proposed cyclic poly(siloxane-g--ethylene oxide) materials also have a good electrochemical stability window and high room temperature ionic conductivity.
  • the present inventors have also incorporated the liquid polymer into solid electrolytes with the same benefits.
  • the present inventors have considered the problems related to carbonate solvents in conventional lithium ion batteries and have concluded that to address these problems, new polymer materials that can readily dissolve metal salts to prepare electrolytes are needed for lithium storage cells and capacitors.
  • the present inventors have developed new siloxane polymer structures with one or more poly(ethylene oxide) side chains.
  • Siloxane is an inorganic material that is not readily decomposed by heat. When the material is thermally decomposed, only a few nonflammable by-products result from the decomposition process because the main chain is a Si-O linkage. This inhibits the combustion cycle.
  • R is alkyl group.
  • the present inventors have also carried out extensive research in this area. Previously, they invented another related liquid type siloxane polymer with one or more poly(ethylene oxide) as a side chain (see general formula II) that are directly bonded to Si atoms.
  • R and R" are alkyl group and R' is hydrogen or alkyl group.
  • the present inventors subsequently discovered a more effective structure of the poly(siloxane-g-ethylene oxide) which is relatively easy to synthesize and achieves high ionic conductivity (approaching to 10 " S/cm at around room temperature).
  • the new liquid poly(siloxane-g-ethylene oxide)s have cvclic structure (see general formula III) that can easily coordinate with lithium salt and dissociate the salt.
  • solid polymer electrolytes can be used as ionic conductors of solid polymer electrolytes by entrapping them inside crosslinked polymer networks, or mixing with solid polymers such as polyacrylonitrile (PAN), poly(methyl methacrylate) (PMMA), poly(vinylidene fluoride) (PVdF), poly(vinylidene fluoride-co-hexafluoropropylene), poly(vinyl acetate), polystyrene, poly(ethylene oxide) (PEO), etc.
  • PAN polyacrylonitrile
  • PMMA poly(methyl methacrylate)
  • PVdF poly(vinylidene fluoride)
  • PVdF poly(vinylidene fluoride-co-hexafluoropropylene
  • polystyrene poly(ethylene oxide) (PEO), etc.
  • a primary object of the present invention is to provide a liquid polymer electrolyte solution having increased room temperature ionic conductivity and enhanced safety characteristics.
  • Another object of the invention is to provide a liquid polymer electrolyte solution with a controlled viscosity for high-energy and long-life lithium secondary batteries, especially for biomedical devices, electric and hybrid vehicles, consumer electronics, submarines, and satellites.
  • a further object of the invention is to provide an electrochemical cell with enhanced shelf life and safety by the use of the present polymeric electrolyte.
  • the liquid polymer electrolyte solution in the present invention is prepared by using the composition which comprises liquid cyclic poly(siloxane- g-ethylene oxide) with proper viscosity and a lithium salt.
  • Figure 1 is a summary of the synthesis of one species of the polysiloxane of present invention.
  • Figure 2 is a plot of temperature vs. conductivity for poly(siloxane-g-3 ethylene oxide) electrolyte.
  • the electrolyte solution of the present invention comprises cyclic siloxane polymers with poly(ethylene oxide) as a side chain (see general formula III).
  • the cyclic type siloxane main body provides flame-retardant properties and chemical stability, and poly(ethylene oxide) side chains give ionic conducting phases.
  • Poly(ethylene oxide) group is directly grafted to silicon atoms in the cyclic siloxane polymer.
  • Cyclic poly(siloxane-g- ethylene oxide)s of the present invention are easily synthesized through simple dehydrogenation reaction using mild catalysts (e.g. aryl borate or potassium carbonate). These catalysts avoid problems arising from the use of metal catalysts such as platinum for the synthesis of poly(siloxane-g-ethylene oxide) with an alkylene spacer between the silicon atom and poly(ethylene oxide) (see general formula I above).
  • the cyclic poly(siloxane-g-ethylene oxide) easily dissolves lithium salt and has enough flexibility to transport lithium ion.
  • the viscosity of poly(siloxane-g-ethylene oxide) can be optimized by controlling the size of siloxane ring or the length of poly(ethylene oxide) side chain. By so optimizing the viscosity, the polymeric electrolyte solution provides high ionic conductivity of close to 10 "3 S/cm at around room temperature.
  • the lithium salt to be used in the present invention is not particularly limited, as long as it serves as an electrolyte for a lithium secondary battery.
  • specific lithium salts include LiClO 4 , LiBF 4 , LiAsF 6 , LiPF 6 , LiCF 3 SO 3 , Li(CF 3 SO 2 ) 2 N, Li(CF 3 SO 2 ) 3 C, LiN(SO 2 C 2 F 5 ) 2 ), lithium alkyl fluorophosphates, lithium oxalatoborate, as well as other lithium bis(chelato)borates having five to seven membered rings, LiPF 3 (C 2 F 5 ) 3 , LiPF 3 (CF 3 ) 3 , LiB(C 2 O ) 2j and mixtures thereof.
  • the molar ratio of the side-chain oxygen of poly(siloxane-g-ethylene oxide), m in General Formula III, to the lithium salt is preferably about 5 to 50. If the proportion of side- chain oxygen is larger than 50, the ionic conductivity of the resulting polymeric electrolyte is undesirably decreased because of the inadequate numbers of carrier ions in the solid polymer electrolyte. If the molar ratio is smaller than 5, the lithium salt is not sufficiently dissociated in the resulting polymeric electrolyte and the aggregation of lithium ions can reduce the ionic conductivity.
  • the polymeric electrolyte solution of the present invention can be applied in lithium secondary batteries in the same way as common carbonate-based electrolyte solutions.
  • Lithium secondary batteries with the present invention's polymeric electrolyte solution as a conducting medium can be fabricated by injecting the polymeric electrolyte solution into a spiral wound cell or prismatic type cell (laminated, Z-fold, etc.). It can also be coated onto the surface of electrodes and assembled with a porous separator to fabricate a single or multi- stacked cell that is packaged in a plastic or plastic/foil laminated pouch.
  • the electrolyte of the present invention can be mixed with the active material, the binder and the electronic additive (a conductor typically made from graphite, carbon black, acetyl black, or other carbonaceous material) to form a slurry and then cast the slurry with an embedded current collector to obtain a composite electrode after drying.
  • Example 1 Eight-membered ring poly(siloxane-g-3 ethylene oxide) (see general formula IV) was synthesized (Sample W98) using a boron catalyst as follows:
  • poly(siloxane-g-3 ethylene oxide) electrolyte shows high ionic conductivity of 1.13 x 10 S/cm at 25°C.
  • Table 1 reports the results of conductivity testing of both 8 member and 10 member ring molecules.
  • Example 3 and the 10 membered ring samples (see Example 2 below) showed favorable conductivity.
  • Example 2 A 10- membered ring poly(siloxane-g-3 ethylene oxide) was synthesized (Sample W96) using a boron catalyst as follows:
  • Example 3 Eight-membered ring poly(siloxane-g-3 ethylene oxide) (see general formula IV) was synthesized (Sample W92) using triethylamine (Et 3 N) as a catalyst as follows: [0033] Triethylamine (Aldrich, 73 ml, 52.50 g, 0.52 mol) was slowly added through a syringe to the cloudy mixture of Df (Gelest Inc., 31.25 g, 0.52 mol Si-H) and tri(ethyleneglycol) monomethyl ether (Aldrich, 85.30 g, 0.52 mol) at 0°C under nitrogen atmosphere. Vigorous bubbling was observed.
  • Example 4 A freestanding solid polymer electrolyte was prepared using the interpenetrating polymerization technique. It was made up of an 8-membered ring poly(siloxane-g-3 ethylene oxide) electrolyte (see general formula IV), poly(ethylene oxide) dimethacrylate as a network forming agent, benzoyl peroxide as a radical initiator and LiN(SO 2 CF 3 ) 2 (LiTFSI) as a lithium salt. The reaction was cured at 70°C for 2hrs. The ionic conductivity of the polymeric electrolytes at 37°C was measured from the AC impedance curves of 2030 button cells assembled by interposing the polymeric electrolyte between two stainless steel discs. The measurement frequency range was from 1 MHz to 10 Hz.
  • the preferred embodiment of the invention is poly(siloxane-g-ethylene oxide) with a molar ratio of the side-chain oxygen of poly(siloxane-g-ethylene oxide), m in General Formula III, to the lithium salt equal to about 5 to 50.
  • Any commonly used lithium salt is acceptable including, without limitation, LiClO 4 , LiBF 4 , LiAsF 6 , LiPF 6 , LiCF 3 SO 3 , Li(CF 3 SO 2 ) 2 N, Li(CF 3 SO 2 ) 3 C, LiN(SO 2 C 2 F 5 ) 2 ), lithium alkyl fluorophosphates, lithium oxaloborate, and mixtures thereof.
  • the average molecular weight of the liquid poly(siloxane- g-ethylene oxide) is optimally less than or equal to 20,000 g/mole.
  • the optimal viscosity of the electrolyte of the present invention is about 10,000 cps or less.
  • Tris(pentafluorophenyl)boron B(C 6 F 5 ) 3 is the preferred catalyst.
  • the preferred network forming polymer comprises poly(alkylene oxide) dialkyl alkyl acrylates represented by General Formula (V):
  • R represents a group selected from an alkyl group having 1 to 10 carbon atoms; and each of R' and R" represents hydrogen or a group selected from an alkyl group having 1 to 10 carbon atoms and or an alkenyl group having 2 to 12 carbon atoms; and X being hydrogen or a methyl group; and n represents numeral of 1 to 15.

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Abstract

La présente invention a trait à un électrolyte en polymère de siloxane cyclique destiné à être utilisé dans des dispositifs de stockage au lithium tels que des accumulateurs et des capacités. Les électrolytes polymériques comprenant des oxydes de poly(siloxane-g-éthylène) avec une ou des chaînes de poly(éthylène oxyde) directement liés aux atomes de Si sont aptes à la synthèse, présentent une longue durée de stockage, possèdent une conductivité ionique supérieure à 10-4 S/cm à la température ambiante, ne s'évaporent à une température inférieure à 150 °C, présentent une large fenêtre de stabilité électrochimique supérieure à 4,5 V (par rapport au lithium), et ne son pas inflammables. La viscosité et la conductivité peuvent être améliorées par le contrôle de la taille du noyau de siloxane ou de la longueur de la chaîne latérale de poly(éthylène oxyde). Le polymère de l'invention peut être utilisé dans des applications d'électrolytes solides en utilisation des agents de solidification ou le piégeage au sein de polymères solides. L'invention a également trait à des moyens de synthèse de cycles à 8 chaînons et à 10 chaînons utilisant du bore et de la triéthylamine en tant que catalyseurs.
PCT/US2003/008779 2002-03-22 2003-03-20 Électrolyte polymérique pour cellule électrochimique Ceased WO2003083973A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US10/491,071 US20040214090A1 (en) 2002-03-22 2003-03-20 Polymer electrolyte for electrochemical cell
AU2003223327A AU2003223327A1 (en) 2002-03-22 2003-03-20 Polymer electrolyte for electrochemical cell

Applications Claiming Priority (14)

Application Number Priority Date Filing Date Title
US10/104,352 2002-03-22
US10/104,352 US20030180624A1 (en) 2002-03-22 2002-03-22 Solid polymer electrolyte and method of preparation
US10/167,940 2002-06-12
US10/167,940 US7498102B2 (en) 2002-03-22 2002-06-12 Nonaqueous liquid electrolyte
USPCT/US03/02128 2003-01-22
USPCT/US03/02127 2003-01-22
PCT/US2003/002128 WO2003083971A1 (fr) 2002-03-22 2003-01-22 Electrolyte polymere solide et procede de fabrication
PCT/US2003/002127 WO2003083970A1 (fr) 2002-03-22 2003-01-22 Electrolyte liquide non aqueuse
US44389203P 2003-01-30 2003-01-30
US60/443,892 2003-01-30
US44684803P 2003-02-11 2003-02-11
US60/446,848 2003-02-11
US45106503P 2003-02-26 2003-02-26
US60/451,065 2003-02-26

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WO2003083973A1 true WO2003083973A1 (fr) 2003-10-09

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PCT/US2003/008740 Ceased WO2003083972A1 (fr) 2002-03-22 2003-03-20 Electrolyte liquide non aqueux
PCT/US2003/008783 Ceased WO2003083974A1 (fr) 2002-03-22 2003-03-20 Procede de fabrication d'electrodes composites
PCT/US2003/008779 Ceased WO2003083973A1 (fr) 2002-03-22 2003-03-20 Électrolyte polymérique pour cellule électrochimique

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PCT/US2003/008740 Ceased WO2003083972A1 (fr) 2002-03-22 2003-03-20 Electrolyte liquide non aqueux
PCT/US2003/008783 Ceased WO2003083974A1 (fr) 2002-03-22 2003-03-20 Procede de fabrication d'electrodes composites

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Cited By (19)

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US6887619B2 (en) 2002-04-22 2005-05-03 Quallion Llc Cross-linked polysiloxanes
US7226702B2 (en) 2002-03-22 2007-06-05 Quallion Llc Solid polymer electrolyte and method of preparation
US7241822B2 (en) 2001-08-30 2007-07-10 Clariant Produkte (Deutschland) Gmbh Dye composition for dyeing powder coatings
US7473491B1 (en) 2003-09-15 2009-01-06 Quallion Llc Electrolyte for electrochemical cell
US7498102B2 (en) 2002-03-22 2009-03-03 Bookeun Oh Nonaqueous liquid electrolyte
US7528572B2 (en) 2004-03-10 2009-05-05 Quallion Llc Power system for managing power from multiple power sources
US7588859B1 (en) 2004-02-11 2009-09-15 Bookeun Oh Electrolyte for use in electrochemical devices
US7695860B2 (en) 2002-03-22 2010-04-13 Quallion Llc Nonaqueous liquid electrolyte
US7718321B2 (en) 2004-02-04 2010-05-18 Quallion Llc Battery having electrolyte including organoborate salt
US8076032B1 (en) 2004-02-04 2011-12-13 West Robert C Electrolyte including silane for use in electrochemical devices
US8076031B1 (en) 2003-09-10 2011-12-13 West Robert C Electrochemical device having electrolyte including disiloxane
US8153307B1 (en) 2004-02-11 2012-04-10 Quallion Llc Battery including electrolyte with mixed solvent
US8715863B2 (en) 2004-05-20 2014-05-06 Quallion Llc Battery having electrolyte with mixed solvent
US8765295B2 (en) 2004-02-04 2014-07-01 Robert C. West Electrolyte including silane for use in electrochemical devices
US9192772B1 (en) 2004-06-29 2015-11-24 Quallion Llc Portable medical power system
US9590269B2 (en) 2013-12-31 2017-03-07 Industrial Technology Research Institute Polyelectrolyte and energy storage device
US9786954B2 (en) 2004-02-04 2017-10-10 Robert C. West Electrolyte including silane for use in electrochemical devices
US10122049B2 (en) 2014-02-06 2018-11-06 Gelion Technologies Pty Ltd Gelated ionic liquid film-coated surfaces and uses thereof
CN109476838A (zh) * 2016-07-13 2019-03-15 三星Sdi株式会社 聚合物、包括聚合物的电解质以及包括聚合物的锂电池

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US7914931B2 (en) * 2005-12-21 2011-03-29 Samsung Sdi Co., Ltd. Separator for rechargeable lithium battery, rechargeable lithium battery including the same, and method for preparing rechargeable lithium battery
US7585428B1 (en) 2007-04-05 2009-09-08 Pacesetter, Inc. Electrolyte with enhanced leakage detection for electrolytic capacitors and method for detecting leakage
KR101386165B1 (ko) 2007-10-26 2014-04-17 삼성에스디아이 주식회사 실란계 화합물을 채용한 유기전해액 및 리튬 전지
CN111048830B (zh) * 2018-10-12 2021-01-15 微宏动力系统（湖州）有限公司 非水电解液及锂离子二次电池
US12438191B2 (en) * 2019-03-25 2025-10-07 Nisshinbo Holdings Inc. Electrolyte additive

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AU2003223327A1 (en) 2003-10-13
WO2003083974A1 (fr) 2003-10-09

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