WO2021225583A1 - Bifunctional ionic liquids for electrolytes - Google Patents
Bifunctional ionic liquids for electrolytes Download PDFInfo
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- WO2021225583A1 WO2021225583A1 PCT/US2020/031453 US2020031453W WO2021225583A1 WO 2021225583 A1 WO2021225583 A1 WO 2021225583A1 US 2020031453 W US2020031453 W US 2020031453W WO 2021225583 A1 WO2021225583 A1 WO 2021225583A1
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- group capable
- ionic liquid
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
- H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
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- 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
- H01M10/0561—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of inorganic materials only
- H01M10/0562—Solid materials
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- 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
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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
Definitions
- the present disclosure relates to a polymerizable polymer electrolyte material formulation, a solid polymer electrolyte, an electrochemical cell containing the solid polymer electrolyte and methods thereof.
- Li-ion batteries have been heavily used in most consumer electronic devices after Sony commercialized the first battery in 1991.
- Electric Vehicles competed for market dominance of personal vehicle sales in the early 20th century, but the advantages of the internal combustion engine (ICE), namely energy-dense fuel and more power, meant that EV development was sporadic and diffused until the 1990’s when General Motors (GM) released its EV-1 and due to California’s Zero-Emissions Vehicle (ZEV) mandate.
- GM General Motors
- ZEV Zero-Emissions Vehicle
- One of the major components of EVs is the energy storage system (ESS) and improving the battery technology can have a potential impact on commercialization of EVs and help reduce the demand for fossil fuels.
- the battery is an expensive component of the vehicle or the device, and hence it is important for the battery to last the lifetime of the vehicle of the device. This means that the next generation Li-ion batteries used in EVs and electronic devices will require significant improvements in all components compared to current state-of-the art Li-ion technologies.
- RTILs room temperature ionic liquids
- Ionic liquids are organic salts with a large cation and an inorganic anion, having melting points below 100 °C. The lattice energy in ionic liquids is reduced due to the bulky cation and hence the melting point is lower.
- ILs are possible alternatives to conventional electrolytes for lithium batteries because of their negligible vapor pressure, non flammability, wide electrochemical window, high chemical and thermal stability, and good ionic conductivity.
- a polymerizable polymer electrolyte material (PEM) formulation including: a polymerizable ionic liquid (IL) monomer containing at least one functional group capable of interacting with lithium ions and a reactive polymerizable functional group capable of crosslinking the monomer; a lithium ion conducting salt; a plasticizer; and a cross-linker.
- IL polymerizable ionic liquid
- a solid polymer electrolyte including: a cross-linked ionic liquid (IL) matrix including a polymer backbone having a functional group capable of interacting with lithium ions with a plurality of pendant groups, and wherein a plurality of cation moieties are attached to one or more of the plurality of pendant groups of the polymer backbone, the cationic moieties being at least one of a nitrogen cation moiety, a phosphorus cation moiety, and a sulfur cation moiety; a lithium ion conducting salt; and a plasticizer.
- IL cross-linked ionic liquid
- an electrochemical cell including positive and negative electrodes spaced apart from each other in the solid polymer electrolyte.
- a method of making a solid polymer electrolyte including: a. forming a reaction mixture including: i. a polymerizable ionic liquid (IL) monomer containing a functional group capable of interacting with lithium ions and a reactive polymerizable functional group, containing at least one of a nitrogen cation moiety, a phosphorous cation moiety, and a sulfur cation moiety, ii. a lithium ion conducting salt, iii.
- IL polymerizable ionic liquid
- a plasticizer iv. polymerization initiator and v. a cross-linker
- Figure 1 shows the molecular structure of a prior art polymerizable IL monomer (ILA) and polymerizable IL monomers (ILB) and (ILC) in accordance with the present disclosure
- Figure 2 shows the molecular structure of synthesized polymerizable IL monomers I-IV in accordance with the present disclosure
- Figure 3 shows a cross-linking solid electrolyte (PEM) design and synthesis
- Figure 4 shows an embodiment of an ion conduction mechanism in the PEM films synthesized using polymerizable IL monomers in accordance with the present disclosure
- Figure 5 is picture depicting the individual parts of a Swagelok Cell used to measure the ionic conductivity of the PEM films
- Figure 6 shows Nyquist Plots used to calculate ionic conductivity of PEM films based on the bulk resistance;
- Figure 7 shows the TGA data for PEM films showing excellent thermal stability at high temperatures;
- Figure 8 shows the molecular structures of polymerizable IL monomers V-XVI in accordance with the present disclosure.
- the disclosed technology relates generally to lithium battery electrolytes. Particularly, this technology is related to non-flammable, non-volatile solid-state electrolytes used for lithium ion transport. This technology also relates to electrolytes useful in energy storage systems suitable for use in consumer electronics and electric drive vehicles.
- the present disclosure describes non-flammable and non-volatile solid electrolytes that overcome safety concerns in current state-of-the-art Li-ion batteries as well as next generation lithium-based batteries.
- the technology is based on innovative cross- linked polymerizable ILs that can form solid polymer electrolytes.
- the disclosure relates to polymerizable ionic liquid (IL) materials (monomers) containing at least one functional group capable of interacting with lithium ions and one reactive polymerizable functional group; polymerizable PEM formulations containing the polymerizable ionic liquid (IL) materials (monomer); solid polymerized PEM containing the polymerized ionic liquid (IL) materials; and electrochemical cells containing the electrolytes incorporating these solid PEMs containing the polymerized ionic liquid (IL) materials.
- IL polymerizable ionic liquid
- a suitable polymerizable ionic liquid (IL) monomer contains a functional group capable of interacting with lithium ions and a reactive polymerizable functional group capable of crosslinking within the polymer.
- the phrase capable of interacting with lithium ions means to increase Li + ion conjugation in the polymer electrolyte material.
- a suitable lithium ion interacting functional group includes a single bond carbon-oxygen-carbon structure. Examples include ether, nitrile, silyl, fluoroalkyl, siloxane, sulfonate, carbonate, ester, ethylene oxide or combinations thereof.
- a suitable reactive polymerizable functional group capable of crossbnking within the polymer contains at least one of a nitrogen cation moiety, a phosphorous cation moiety and a sulfur cation moiety.
- Such suitable crossbnking functional groups include vinyl, allyl, acrylate, benzylvinyl or acryloyl groups.
- a solid polymer electrolyte prepared from a formulation which includes a lithium ion conducting salt, a plasticizer, a cross-linker, a plurality of polymerizable ionic liquid (IL) monomers containing at least one functional group capable of interacting with lithium ions and a reactive polymerizable functional group capable of crosslinking within the polymer, and a photo initiator.
- a formulation which includes a lithium ion conducting salt, a plasticizer, a cross-linker, a plurality of polymerizable ionic liquid (IL) monomers containing at least one functional group capable of interacting with lithium ions and a reactive polymerizable functional group capable of crosslinking within the polymer, and a photo initiator.
- IL polymerizable ionic liquid
- an electrical energy storage device includes an electrolyte prepared from a formulation containing a) a lithium ion conducting salt; b) a plasticizer; c) a cross-linker; d) a plurality of polymerizable ionic liquid (IL) monomers containing at least one functional group capable of interacting with lithium ions and a reactive polymerizable functional group capable of crossbnking within the polymer; and e) a photo-initiator.
- IL polymerizable ionic liquid
- the solid PEM electrolyte includes a polymerized IL matrix having a polymer backbone containing at least one functional group capable of interacting with lithium ions.
- the polymer backbone has a plurality of pendant groups having cationic moieties including at least one of a nitrogen cation moiety, a phosphorus cation moiety, and a sulfur cation moiety which are crosslinked in the polymer matrix by vinyl, allyl, acrylate, benzylvinyl or acryloyl groups.
- the PEM electrolyte further includes a lithium ion conducting salt and a plasticizer.
- the nitrogen cation moiety is selected from a group consisting of imidazolium, ammonium, pyridinium, piperidinium, pyrrolidinium, azepinium, and morpholinium moieties.
- the phosphorus cation moiety is selected from a group consisting of phosphonium moieties.
- the sulfur cation moiety is selected from a group consisting of sulfonium moieties.
- the polymerizable IL monomer includes a vinyl or allyl or acrylate imidazolium moiety, a vinyl or allyl or acrylate ammonium moiety, a vinyl or allyl or acrylate pyridinium moiety, a vinyl or allyl or acrylate piperidinium moiety, a vinyl or allyl or acrylate pyrrolidinium moiety, a vinyl or allyl or acrylate azepinium moiety, a vinyl or allyl or acrylate morpholinium moiety, a vinyl or allyl or acrylate phosphonium moiety, a vinyl or allyl or acrylate sulfonium moiety.
- the preferred polymerizable IL monomer includes vinyl imidazolium moiety, vinyl pyrrolidinium, acrylate ammonium moiety, acrylate pyrrolidinium moiety.
- the crosslink of the crosslinked polymeric ionic liquid matrix includes at least one of a nitrogen cation moiety, a phosphorus cation moiety, and a sulfur cation moiety.
- the crosslink of the crosslinked polymerizable IL is a gemini IL moiety.
- ILB suitable molecular structures of polymerizable IL material containing a functional group capable of interacting with lithium ions
- ILA is a comparative polymerizable IL material not containing a functional group (e.g., alkyl chain) capable of interacting with lithium ions.
- the polymerizable IL material containing a functional group capable of interacting with lithium ions is present in a range of from 0.1 % to 50 % by weight of each of the solid PEM electrolyte and the polymerizable PEM formulation.
- the lithium ion conducting salt is present in a range of from 10 % to 50 % by weight of each of the solid PEM electrolyte and the polymerizable PEM formulation.
- Suitable lithium ion conducting salts include LiBF 4 , LiNO 3 , LiPF 6 , LiAsF 6 , lithium bis(trifluoromethylsulfonyl)imide (LiTFSI), lithium bis(pentafhuoroethylsulfonyl)imide, lithium trifluoroacetate, LiBoB, LiDFOB, L1PO2F2, or the like or mixtures thereof.
- a plasticizer capable of dissociating lithium ions is present in a range of from 5 % to 50 % by weight of each of the solid PEM electrolyte and the polymerizable PEM formulation.
- the plasticizer is a non-polymerizable RTIL.
- the ionic liquid contains an organic cation and an inorganic/organic anion, with suitable organic cations including N-alkyl-N-alkyl-imidazolium, N-alkyl-N-alkyl- pyrrolidinium, N-alkyl-N-alkyl-pyridinium, N-alkyl-N-alkyl-sulfonium, N-alkyl-N-alkyl- ammonium, N-alkyl-N-alkyl-piperidinium or the like, and suitable anions including tetrafluoroborate, hexafluorophosphate, bis(trifluoromethylsulfonyl)imide, bis(pentafluoroethylsulfonyl)imide, trifluoroacetate or the like.
- suitable organic cations including N-alkyl-N-alkyl-imidazolium, N-alkyl-N-alkyl- pyrrolidinium
- the plasticizer is a mono- or di-ether containing ethylene glycol. Suitable examples include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene glycol methyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, or mixtures thereof.
- a battery is provided including positive and negative electrodes separated from each other by the solid electrolyte described herein.
- a method of making a composite electrolyte includes (1) forming a reaction mixture including a polymerizable IL monomer containing a functional group capable of interacting with lithium ions and a reactive polymerizable functional group capable of crosslinking within the polymer containing at least one of a nitrogen cation moiety, a phosphorous cation moiety and a sulfur cation moiety, and (2) initiating polymerization in the reaction mixture to form a polymeric ionic liquid matrix.
- a polymerization initiator is present in a range of from 0.1 % to 5 % by weight of the polymerizable formulation.
- the polymerization is a free radical polymerization reaction.
- the reaction is initiated by heat, or by ultraviolet energy or by microwave energy.
- the method further includes adding an initiator in the reaction mixture.
- the polymerization is initiated by ultraviolet energy by using 2-Hydroxy-2-methylpropiophenone as the photo- initiator.
- Polymerizable ILs are a class of functional polymers useful in a variety of applications.
- the repeating units of these polymers bear an electrolyte group (cation or anion).
- Ionic conductivity of the ILs depends on several factors: chemical nature of the polymer backbone, nature of ions and glass transition temperature (Tg).
- Tg glass transition temperature
- the present monomer ILs offer high Li + ion transference number.
- the high Li + ion transference number is a consequence of the cation immobilized to the polymer backbone and thereby not participating in the ionic conduction.
- film type e.g., solid polymer, ion conductive materials are preferred over liquid electrolytes.
- Polymerizable groups can be appended to the ionic liquid constituents. As compared to liquid electrolytes, the solid polymers are lighter in weight and are more easily processed, treated and packaged.
- the electrolyte for a lithium ion battery having improved ionic conductivity, thermal and mechanical stability is described.
- the electrolyte includes a polymerizable IL material that can be cast or formed into a variety of shapes such as films, membranes and blocks.
- the polymeric IL is formed from the crosslinking of polymerizable IL monomers and includes a backbone (that optionally can include ionic liquid moieties) and pendant ionic liquid groups (shown as paired positively and negatively charged particles).
- An embodiment of the ionic liquid PEM includes a bifunctional ionic liquid crosslink (crosslinkable gemini ionic liquid) that provides mechanical stability to the film and that further assists the ionic conductivity of the composite.
- IL-based hybrid PEMs that exhibit high ionic conductivity, wide electrochemical stability and high thermal stability for applications in EVs or PHEVs are disclosed. These electrolytes can be incorporated into Li-metal batteries, Li-Sulfur batteries and Li ion batteries with high voltage cathodes.
- a bifunctional polymerizable IL monomer is an ionic liquid in which one or more polymerizable units are incorporated.
- the polymerizable feature can be located on the cation, or on the anion, or both the cation and the anion.
- the bifunctionality of the IL is due to a) the reactive end groups capable of polymerization, and b) a functional group capable of interacting with lithium ions of the lithium conducting salt.
- a suitable functional group capable of interacting with lithium ions is selected from ether, nitrile, silyl, fluoroalkyl, siloxane, sulfonate, carbonate, ester or combinations thereof.
- commercial cross-linkers can be partially or fully replaced with bifunctional ILs to generate polymer electrolytes with enhanced ionic conductivity, without compromising the mechanical stability.
- Examples of IL monomers including a nitrogen cation moiety having a nitrogen cation selected from the group including but not limited to an imidazolium, ammonium, pyridinium, piperidinium, pyrrolidinium, azepinium, and morpholinium nitrogen cation moieties. These groups can be functionalized with side groups that are capable of polymerization. Polymerizable groups include vinyl, allyl, acrylate, benzylvinyl and acryloyl groups. These reactive groups are capable of free radical, thermal, ultra-violet or microwave- initiated polymerization, thereby incorporating the monomer IL into the polymer.
- Figure 1 shows the molecular structure of a prior art polymerizable IL monomer ILA lacking a functional group capable of interacting with lithium ions in comparison with the molecular structure of polymerizable IL monomers ILB and ILC, used in the Examples for generating PEM films, each having incorporated in the monomer structure a functional group capable of interacting with lithium ions and a reactive polymerizable functional group capable of crosslinking the monomer.
- Figure 2 shows the molecular structure of suitable polymerizable IL monomers I-IV each containing a functional group capable of interacting with lithium ions and a reactive polymerizable functional group capable of crosslinking the monomer.
- ILs including for example, imidazolium, ammonium, pyridinium, piperidinium, pyrrolidinium, azepinium, and morpholinium nitrogen cation moieties, as well as phosphonium and sulfonium cation moieties can also be used.
- a family of vinyl functionalized polymerizable imidazolium (Im), pyrrolidinium (Pyr) and piperidinium (Pip) cation-based monomer ILs are suitable for use as ionic polymer monomers.
- Vinyl monomer ionic liquids having bis(trifluoromethylsulfonyl)imide (TFSI) as counter ion can be synthesized.
- the composite electrolyte also includes a crosslinker that crosslinks with the polymerizable ionic liquid (IL) monomer of the present disclosure and helps improve mechanical strength.
- Crosslinkers play a role in dictating the flexibility of the membrane.
- the crosslinker can be a conventional bifunctional molecule (IL monomer) or it can itself be an ionic liquid capable of polymerization.
- the bifunctional nature of the crosslinker creates bridges between polymer chains; however, the crosslinker can also be incorporated into a growing polymer chain.
- Conventional crosslinkers include moieties having two or more vinyl features, such as divinyl benzene, dimethacrylates and diacrylates.
- the crosslinking ionic liquid can form a bridge between two polymeric backbones, or it can become incorporated into the polymeric backbone, thereby increasing the ion conductivity of the polymer itself. This is shown in Figure 3 with the cross-linker and the monomer IL each having ether groups, which allow for faster Li + ion transport.
- Figure 8 shows the molecular structures of polymerizable IL monomers V-XVI each containing a functional group capable of interacting with lithium ions and a reactive polymerizable functional group capable of crosslinking within the polymer.
- Figure 8 depicts various suitable bi-functional polymerizable ionic liquid (IL) monomers comprising vinyl pyrrolidinium cation with ether oxygen functional moieties (Monomer V), vinyl piperidinium cation with ether oxygen functional moieties (Monomer VI), styrene pyrrolidinium cation with nitrile functional moieties (Monomer VII), vinyl ammonium cation with trimethyl silyl functional moieties (Monomer VIII), vinyl piperidinium cation with trimethyl silyl functional moieties (Monomer IX), vinyl phosphonium cation with nitrile functional moieties (Monomer X), vinyl sulfonium cation with nitrile functional moieties (Monomer V
- Example A The PEM films of Comparison Example (CE) 1, CE 2, CE 3 and Example 1 were made from formulations containing a lithium conducting salt, monomer ILs, plasticizers and cross-linkers and polymerized by UV radiation using a photo initiator.
- the cross-linkers are responsible for mechanical strength, whereas the plasticizer helps dissociate the salt, hence increasing the ionic conductivity.
- the monomer ILs provide a balance between the ionic conductivity and mechanical properties of the PEM films.
- the individual components of the PEM films are mixed using a centrifugal mixer yielding highly viscous polymer gels.
- the viscous polymer gels are drop-casted on a glass plate and the plate is passed under UV light to generate PEM films having 50 pm thickness as shown in Figure 4.
- Figure 4 illustrates an ion conduction mechanism in the PEM films synthesized using polymerizable IL monomers. The degree of cross-linking can be tuned by changing the UV light exposure time and intensity.
- FTIR 3151, 1346, 1176, 1051 cm -1 .
- the ionic conductivity is calculated based on the bulk resistance of the PEM film obtained from the Nyquist Plots using the formula below. Disclosed films sandwiched between the upper and lower plungers in a Swagelok cell, with cells hermetically sealed for better contact than coin cells, hence lowering the interfacial resistance.
- Figure 5 illustrates a picture of the individual parts of a Swagelok Cell used to measure the ionic conductivity of the PEM films.
- s is the ionic conductivity calculated using the thickness (t) and area (A) of the PEM films, and R is the bulk resistance obtained from the Nyquist plots.
- the ionic conductivity data for PEM films is reported in a temperature range of from 25 to 45 °C, which is considered standard operating temperature conditions for lithium- based batteries in various applications. Without any plasticizer in CE 1 films, we can see low ionic conductivity values less than 0.05 mS/cm at room temperature. These films have a higher loading of cross-linker than films containing ILA where the monomer IL does not have EO groups in the molecular structure, resulting in low conductivity PEMs. Increasing the Li + ion conducting salt and optimizing the cross-linker concentration increases the ionic conductivity in CE 3 films compared to CE 2 films.
- Example 1 PEMs are further optimized using the triacrylate cross-linker B, with 3 reactive sites, leading to more cross-linked PEM films, and hence only 10 wt. % is needed in the formulation.
- Figure 6 shows the Nyquist Plots used to calculate ionic conductivity of the PEM films based on the bulk resistance. Hence, we see the room temperature (25 °C) ionic conductivity increase from 0.33 mS.cm 1 in CE 3 PEM to 0.82 mS.cm 1 in Example 1 PEM (Table B). It is important to note that these are solid PEM films without any liquid or gel component and can achieve high ionic conductivity values at room temperature.
- Figure 7 depicts the plots of TGA data for CE 2 an CE 3 PEM films compared to the Example 1 PEM film showing excellent thermal stability at high temperatures.
- Example 1 PEM films, as well as CE 2 and CE 3 have excellent thermal stability even above 250 °C, and thus can enhance the safety of lithium-based batteries.
- Use of PEMs in accordance with the present disclosure in lithium-based batteries will allow for safer operations in a wide temperature window.
- step A To a 20 mL vial containing the mixture from step A was added 1-vinylimidazole. No exotherm was observed and the mixture stirred at RT under neat conditions. The reaction was monitored by TLC (silica gel, 50% EtOAc/DCM). Unreacted vinylimidazole was present in much smaller proportions relative to product which does not migrate from the origin. The amber mixture stirred at RT for 9 days and a viscous light amber oil was formed. Yield: light amber oil, 7.5 g (>99%).
- FTIR 3149, 1730, 1347, 1174 cm -1 .
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CA3177541A CA3177541A1 (en) | 2020-05-05 | 2020-05-05 | Bifunctional ionic liquids for electrolytes |
KR1020227036512A KR20230007334A (en) | 2020-05-05 | 2020-05-05 | Bifunctional ionic liquids for electrolytes |
JP2022567301A JP2023533105A (en) | 2020-05-05 | 2020-05-05 | Bifunctional ionic liquid for electrolyte |
EP20934350.8A EP4146392A1 (en) | 2020-05-05 | 2020-05-05 | Bifunctional ionic liquids for electrolytes |
CN202080102716.6A CN115867383A (en) | 2020-05-05 | 2020-05-05 | Bifunctional ionic liquids for electrolytes |
AU2020446650A AU2020446650A1 (en) | 2020-05-05 | 2020-05-05 | Bifunctional ionic liquids for electrolytes |
PCT/US2020/031453 WO2021225583A1 (en) | 2020-05-05 | 2020-05-05 | Bifunctional ionic liquids for electrolytes |
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CN114497726A (en) * | 2022-01-25 | 2022-05-13 | 中国科学院过程工程研究所 | High-conductivity semi-interpenetrating polymer electrolyte containing ionic liquid cross-linking agent |
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- 2020-05-05 AU AU2020446650A patent/AU2020446650A1/en active Pending
- 2020-05-05 CA CA3177541A patent/CA3177541A1/en active Pending
- 2020-05-05 JP JP2022567301A patent/JP2023533105A/en active Pending
- 2020-05-05 WO PCT/US2020/031453 patent/WO2021225583A1/en unknown
- 2020-05-05 EP EP20934350.8A patent/EP4146392A1/en active Pending
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN114497726A (en) * | 2022-01-25 | 2022-05-13 | 中国科学院过程工程研究所 | High-conductivity semi-interpenetrating polymer electrolyte containing ionic liquid cross-linking agent |
CN114497726B (en) * | 2022-01-25 | 2024-03-12 | 中国科学院过程工程研究所 | High-conductivity semi-interpenetrating polymer electrolyte containing ionic liquid cross-linking agent |
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