Polymer adhesives comprising labels for

Abstract

The invention provides an electrode material. The electrode material comprises an active material; a non-fluorinated polymer binder comprising a detectable label; and a conductive filler.

Description

Technical Field

[0001] This invention relates to battery cell technology, and more particularly to polymer binders for electrodes in electrochemical battery cells. Background Technology

[0002] High-voltage electrical systems are increasingly used to power onboard functions in both mobile and stationary systems. For example, in motor vehicles, the need for increased fuel economy and reduced emissions has led to the development of advanced electric vehicles (EVs). EVs rely on rechargeable energy storage systems (RESS), typically including one or more high-voltage battery packs, and an electric drivetrain to deliver power from the battery to the wheels. Depending on the power requirements of a given application, the battery pack can include any number of interconnected battery modules. Each battery module comprises an assembly of electrically coupled electrochemical cell units. The battery pack is configured to provide a direct current (DC) output voltage suitable for powering coupled electrical and / or mechanical loads, such as electric motors.

[0003] Electrodes in a battery are among the key components responsible for the electrochemical reactions that occur during charging and discharging. Modern automotive high-voltage battery packs benefit from high-energy-density electrodes to improve overall performance and range. However, there remains a persistent need for fluoropolymer binder materials, as well as the ability to quantitatively determine the distribution and eventual migration of polymer binders in electrode materials during battery assembly and subsequent operation. Summary of the Invention

[0004] One aspect provides an electrode material. The electrode material includes an active material; a non-fluorinated polymer binder containing a detectable label; and a conductive filler.

[0005] In another embodiment of the electrode material, the non-fluorinated polymer binder comprises a first repeating unit derived from a first monomer containing a detectable marker.

[0006] In another embodiment of the electrode material, the non-fluorinated polymer binder further comprises a second repeating unit derived from one or more second monomers selected from (meth)acrylates, vinyl aromatic compounds, vinyl ethers, vinyl ketones, and vinyl esters.

[0007] In another embodiment of the electrode material, the non-fluorinated polymer binder further comprises a third repeating unit, which includes crosslinkable groups, crosslinking groups, or combinations thereof.

[0008] In another embodiment of the electrode material, the detectable markers include fluorescein or derivatives thereof, rhodamine or derivatives thereof, acridine or derivatives thereof, coumarin or derivatives thereof, eosin or derivatives thereof, erythrosine or derivatives thereof, pyrene or derivatives thereof, or combinations thereof.

[0009] In another embodiment of the electrode material, the non-fluorinated polymer binder is prepared by free radical polymerization of the following: a first monomer containing a detectable label; one or more second monomers selected from (meth)acrylates, vinyl aromatic compounds, vinyl ethers, vinyl ketones and vinyl esters; and optionally, a third monomer containing a crosslinkable group, a crosslinkable group or a combination thereof.

[0010] In another embodiment of the electrode material, the electrode material does not include a fluorinated binder.

[0011] On the other hand, an electrochemical cell unit is provided, comprising a positive electrode, a negative electrode, and an electrolyte. At least one of the positive or negative electrodes comprises the electrode material described herein.

[0012] In another embodiment of the electrochemical cell unit, the non-fluorinated polymer binder includes a first repeating unit derived from a first monomer including a detectable label.

[0013] In another embodiment of the electrochemical cell unit, the non-fluorinated polymer binder further comprises a second repeating unit derived from one or more second monomers selected from (meth)acrylates, vinyl aromatic compounds, vinyl ethers, vinyl ketones, and vinyl esters.

[0014] In another embodiment of the electrochemical cell unit, the non-fluorinated polymer binder further includes a third repeating unit comprising crosslinkable groups, crosslinkable groups, or combinations thereof.

[0015] In another embodiment of the electrochemical cell unit, the detectable label includes fluorescein or a derivative thereof, rhodamine or a derivative thereof, acridine or a derivative thereof, coumarin or a derivative thereof, eosin or a derivative thereof, erythrosine or a derivative thereof, pyrene or a derivative thereof, or a combination thereof.

[0016] In another embodiment of the electrochemical cell unit, the non-fluorinated polymer binder is prepared by free radical polymerization of the following: a first monomer containing a detectable label; one or more second monomers selected from (meth)acrylates, vinyl aromatic compounds, vinyl ethers, vinyl ketones and vinyl esters; and optionally, a third monomer containing crosslinkable groups, crosslinking groups or combinations thereof.

[0017] In another embodiment of the electrochemical battery cell, the electrode material does not include fluorinated binders.

[0018] On the other hand, a method for measuring the distribution of a binder in an electrode material is provided. The method includes providing an electrode material as described herein; exposing the electrode material to activation radiation sufficient to provide a quantitative signal from a detectable marker; and determining the distribution of a non-fluorinated polymer binder based on the quantitative signal from the detectable marker.

[0019] In another embodiment of the method, the method further includes charging and discharging the electrochemical cell containing the electrode material prior to the step of providing the electrode material.

[0020] In another embodiment of the method, the non-fluorinated polymer adhesive includes a first repeating unit derived from a first monomer including a detectable marker.

[0021] In another embodiment of the method, the non-fluorinated polymer adhesive further comprises a second repeating unit derived from one or more second monomers selected from (meth)acrylates, vinyl aromatic compounds, vinyl ethers, vinyl ketones, and vinyl esters.

[0022] In another embodiment of the method, the non-fluorinated polymer adhesive further includes a third repeating unit comprising crosslinkable groups, crosslinking groups, or combinations thereof.

[0023] In another embodiment of the method, the electrode material does not include fluorinated binders.

[0024] The above-described features and advantages, as well as other features and advantages, of this disclosure will become apparent from the following detailed description when taken in conjunction with the accompanying drawings. Attached Figure Description

[0025] Other features, advantages, and details appear only by way of example in the following detailed description, which refers to the accompanying drawings, wherein:

[0026] Figure 1 It is a vehicle configured according to one or more embodiments;

[0027] Figure 2 An exemplary electrochemical cell (battery) comprising the disclosed electrode materials according to the present invention is illustrated schematically;

[0028] Figure 3A The images show visual representations of electrode materials illuminated with a Royal Blue lamp, using scalar bars of 100 micrometers (μm).

[0029] Figure 3B This is a visual image of an example of electrode material illuminated with a Royal blue lamp and a filter, using a scalar bar of 100 μm. Detailed Implementation

[0030] The following description is exemplary in nature only and is not intended to limit this disclosure, its application, or use. It should be understood that in all the accompanying drawings, corresponding reference numerals denote the same or corresponding parts and features. As used herein, the terms "anode" and "negative electrode" are used interchangeably, as are the terms "cathode" and "positive electrode."

[0031] This technology relates to improved electrochemical battery cells (e.g., battery cells), particularly lithium-ion batteries, or more specifically lithium metal batteries, which can be used in vehicle applications. However, this technology can also be used in other electrochemical devices, such as sodium-ion batteries, therefore the discussion of lithium-ion batteries herein is non-limiting.

[0032] According to an exemplary embodiment, the vehicle is Figure 1 The vehicle 10 is generally represented by 10. The vehicle 10 is shown in the form of an automobile having a body 12. The body 12 includes a passenger compartment 14, within which a steering wheel, front seats, and rear passenger seats (not shown separately) are arranged. Several components are arranged within the body 12, including, for example, an electric motor 16 (shown by a projection under the hood). The electric motor 16 is shown only for ease of illustration and discussion. It should be understood that the configuration, location, size, arrangement, etc., of the electric motor 16 are not intended to be particularly limited, and all such configurations (including multi-motor configurations) are within the scope of this disclosure.

[0033] The electric motor 16 is powered by a battery pack 18 (shown in projection near the rear of the vehicle 10). The battery pack 18 is shown for ease of illustration and discussion only. It should be understood that the configuration, location, size, arrangement, etc., of the battery pack 18 are not intended to be particularly limited, and all such configurations (including separate configurations) are within the scope of this disclosure. Furthermore, although this disclosure is primarily discussed in the context of the battery pack 18 configured for the electric motor 16 of the vehicle 10, the aspects described herein can be similarly incorporated into any system (vehicle, building, etc.) having an energy storage system (e.g., one or more battery packs or modules), and all such configurations and applications are within the scope of this disclosure.

[0034] As previously described, in some embodiments, battery pack 18 includes an electrochemical battery cell or battery comprising a positive electrode, a negative electrode, and an electrolyte. An electrochemical battery cell is also provided, comprising a cathode, an anode, and an electrolyte located between the cathode and the anode. Figure 2 A battery pack according to one or more embodiments is shown (e.g. Figure 1 A simplified configuration of the electrochemical cell units in the battery pack 18). For example... Figure 2 As shown, the electrochemical cell 200 may include a cathode 202 (i.e., the positive electrode), an anode 204 (i.e., the negative electrode), and an electrolyte 206 located between the cathode 202 and the anode 204. Although only a single electrochemical cell 200 is shown for convenience, it should be understood that the battery pack may include any number of cell units required to meet battery design constraints (e.g., capacity requirements). At least one of the positive electrode (cathode 202) or the negative electrode (anode 204) comprises the electrode material provided herein.

[0035] One aspect provides an electrode material. The electrode material includes an active material, a non-fluorinated polymer binder containing a detectable label, and a conductive filler. The electrode material can be a cathode material or an anode material. For example, one or both of the cathode and anode materials may include a non-fluorinated polymer binder containing a detectable label. In some embodiments, the electrode material may not include a fluorinated binder. For example, one or both of the cathode and anode materials may include a non-fluorinated polymer binder containing a detectable label, and one or both of the cathode and anode materials may not include a fluorinated binder.

[0036] Non-fluorinated polymer adhesives include detectable tags. Detectable tags provide signal generators, which are molecules or portions capable of providing a detectable signal using one or more detection techniques (e.g., spectrometry, calorimetry, spectroscopy, or visual inspection). Suitable examples of detectable signals may include optical, electrical, or radioactive signals. Examples of signal generators useful in this method include, for example, chromophores, fluorophores, Raman-active tags, radioactive tags, enzymes, enzyme substrates, or combinations thereof. For example, a detectable tag may be a luminescent tag, a fluorescent tag, or a combination thereof (as described herein, they may be collectively referred to as fluorophores).

[0037] Suitable radioactive isotopes can include H-3, C-11, C-14, F-18, P-32, S-35, I-123, I-124, I-125, I-131, Cr-51, Cl-36, Co-57, Fe-59, Se-75, and Eu-152. Halogen isotopes (e.g., chlorine, fluorine, bromine, and iodine) and metals including technetium, yttrium, rhenium, and indium are also useful notations. Typical examples of metal ions that can be used as signal generators include Tc-99m, I-123, In-111, I-131, Ru-97, Cu-67, Ga-67, I-125, Ga-68, As-72, Zr-89, Gd-153, and Ti-201. Radioactive isotopes used for in vivo diagnostic imaging via positron emission tomography (“PET”) include C-11, F-18, Ga-68, and I-124. These can be paramagnetic labels of metal ions present as metal complexes or metal oxide particles. Suitable paramagnetic isotopes may include Gd-157, Mn-55, Dy-162, Cr-52, and Fe-56.

[0038] As used herein, the terms "paramagnetic metal ion," "paramagnetic ion," or "metal ion" refer to a metal ion that is magnetized to a degree proportional to the magnetic field, either parallel or antiparallel to it. Generally, these are metal ions possessing unpaired electrons. Examples of suitable paramagnetic metal ions include, but are not limited to, gadolinium III, iron III, manganese II, yttrium III, dysprosium III, and chromium III.

[0039] In some embodiments, the detectable marker may be a fluorophore. As used herein, the term "fluorophore" refers to a chemical compound or portion that emits light (at different wavelengths) when exposed to light of a specific wavelength. Fluorophores can be described by their emission profile or "color". Green fluorophores (e.g., Cy3, FITC, and Oregon Green) are characterized by their emission wavelengths typically in the range of 515–540 nm. Red fluorophores (e.g., Texas Red, Cy5, and tetramethylrhodamine) are characterized by their emission wavelengths typically in the range of 590–690 nm. Examples of fluorophores include, but are not limited to, 4-acetamido-4′-isothiocyanostilbene-2,2′-disulfonic acid, acridine, derivatives of acridine and acridine isothiocyanate, 5-(2′-aminoethyl)aminonaphthalene-1-sulfonic acid (EDANS), 4-amino-N-[3-vinylsulfonyl)phenyl]naphthalimide-3,5-disulfonic acid (Lucifer Yellow VS), N-(4-anilino-1-naphthyl)maleimide, o-aminobenzamide, Brilliant Yellow, coumarin, and coumarin. Coumarin derivatives, 7-amino-4-methylcoumarin (AMC, coumarin 120), 7-amino-trifluoromethylcoumarin (coumarin 151), cyanoctyl; 4′,6-diamino-2-phenylindole (DAPI), 5′,5″-dibromopyrogallol-sulfophthalein (bromopyrogallol red), 7-diethylamino-3-(4′-isothiocyanophenyl)-4-methylcoumarin, 4,4′-diisothiocyanate-stilbene-2,2′-disulfonic acid ... Cyano-stilbene-2,2′-disulfonic acid; 5-[dimethylamino]naphthalene-1-sulfonyl chloride (DNS, dansyl chloride); eosin, eosin derivatives such as eosin isothiocyanate, erythrosin, erythrosin derivatives such as erythrosin B and erythrosin isothiocyanate; ethidium; fluorescein and its derivatives such as 5-carboxyfluorescein (FAM), 5-(4,6-dichlorotriazine-2-yl)aminofluorescein (DTAF), 2′7′-dimethoxy-4′5′-dichloro-6-carboxyfluorescein JOE, fluorescein, FITC, QFITC ​​(XRITC); fluorescent amine derivatives (fluoresce upon reaction with amines); IR144; IR1446; malachite green isothiocyanate; 4-methylumbelliferone; o-toluphthalene; nitrotyrosine; pararosaniline; phenol red, β-phycoerythrin; o-phthalaldehyde derivatives (fluoresce upon reaction with amines); pyrene and its derivatives, such as pyrene, pyrene butyrate, and succinimide-1-pyrene butyrate; Reactive Red 4 ( Rhodamine and its derivatives, such as 6-carboxy-X-rhodamine (ROX), 6-carboxyrhodamine (R6G), rhodamine B sulfonyl chloride, rhodamine (Rhod), rhodamine B, rhodamine 123, rhodamine X isothiocyanate, sulfonylrhodamine B, sulfonylrhodamine 101, and sulfonylrhodamine 101 sulfonyl chloride derivatives (Texas Red); N,N,N′,N′-tetramethyl-6-carboxyrhodamine (TAMRA); tetramethylrhodamine, tetramethylrhodamine isothiocyanate (TRITC); riboflavin; biotin; rosemary acid and lanthanum chelate derivatives, quantum dots, anthocyanins, and squaric acid. In some embodiments, detectable labels may include fluorescein or its derivatives, rhodamine or its derivatives, acridine or its derivatives, coumarin or its derivatives, eosin or its derivatives, erythrosine or its derivatives, pyrene or its derivatives, or combinations thereof.

[0040] In some embodiments, the non-fluorinated polymer adhesive may include a first repeating unit derived from a first monomer including a detectable label. The first monomer may include any suitable polymerizable group, such as (meth)acrylate, vinyl aromatic compounds, vinyl ethers, vinyl ketones, or vinyl esters. The polymerizable group may be directly bound to the detectable label portion, or the polymerizable group may be bound to the detectable label portion via one or more divalent linking groups.

[0041] As used herein, unless otherwise defined, "divalent linker" means a divalent group, including one or more of the following: -O-, -S-, -C(O)-, -N(R')-, -C(O)N(R')-, -S(O)-, -S(O)2-, substituted or unsubstituted C 1-30 Alkylene, substituted or unsubstituted C 3-30 Cycloalkylene, substituted or unsubstituted C 3-30 Heterocyclic alkyl, substituted or unsubstituted C 6-30 aryl, substituted or unsubstituted C 3-30 Heteroaryl groups or combinations thereof, wherein each R' is independently hydrogen, substituted or unsubstituted C. 1-20 Alkyl, substituted or unsubstituted C 1-20 Heteroalkyl, substituted or unsubstituted C 6-30 aryl or substituted or unsubstituted C 3-30 Heteroaryl groups. Typically, the divalent linking group includes one or more of the following: -O-, -S-, -C(O)-O-, -N(R')-, -C(O)N(R')-, -S(O)-, -S(O)2-, substituted or unsubstituted C- groups. 1-30 Alkylene, substituted or unsubstituted C 3-30 Cycloalkylene, substituted or unsubstituted C 3-30 Heterocyclic alkyl, substituted or unsubstituted C6-30 aryl, substituted or unsubstituted C 3-30 Heteroaryl groups or combinations thereof, wherein R' is hydrogen, substituted or unsubstituted C. 1-20 Alkyl, substituted or unsubstituted C 1-20 Heteroalkyl, substituted or unsubstituted C 6-30 aryl, or substituted or unsubstituted C 3-30 Heteroaryl groups. More typically, the divalent linking group includes at least one of the following: -O-, -C(O)-, -C(O)O-, -N(R')-, -C(O)N(R')-, substituted or unsubstituted C 1-10 Alkylene, substituted or unsubstituted C 3-10 Cycloalkylene, substituted or unsubstituted C 3-10 Heterocyclic alkyl, substituted or unsubstituted C 6-10 aryl, substituted or unsubstituted C 3-10 Heteroaryl groups or combinations thereof, wherein R is hydrogen, substituted or unsubstituted C. 1-10 Alkyl, substituted or unsubstituted C 1-10 Heteroalkyl, substituted or unsubstituted C 6-10 aryl or substituted or unsubstituted C 3-10 Mixed aromatic compounds.

[0042] "Substitution" refers to the substitution of at least one hydrogen atom in a chemical structure or group by another terminal substituent, typically monovalent, provided that the valence does not exceed the normal valence of the specified atom. Exemplary substituents that may be present at the "substitution" position include, but are not limited to, nitro (-NO2), cyano (-CN), hydroxyl (-OH), oxo (O), amino (-NH2), mono- or di-(C) 1-6 )alkylamino, C 2-6 Alkyl (e.g., acyl), formyl (-C(O)H), carboxylic acid or its alkali metal salt or ammonium salt; C 2-6 Alkyl esters (-C(O)O-alkyl or -OC(O)-alkyl), C 7-13 Aryl esters (-C(O)O-aryl or -OC(O)-aryl); amides (-C(O)NR2, where each R is hydrogen or C). 1-6 Alkyl), carboxymethylamino (-CH2C(O)NR2, where each R is hydrogen or C 1-6 Alkyl groups, halogens, thiols (-SH), C 1-6 Alkylthio (-S-alkyl), thiocyano (-SCN), C 1-6 Alkyl, C 2-6 alkenyl, C 2-6 alkynyl group, C 1-6 Haloalkyl, C 1-9 Alkoxy, C 1-6 Halogenated alkoxy groups, C 3-12cycloalkyl, C 5-18 Cycloalkenyl, C 2-18 Heterocyclic alkenyl groups, C groups having at least one aromatic ring 6-12 Aryl (e.g., phenyl, biphenyl, naphthyl, etc., each ring being substituted or unsubstituted aromatic), C 7-19 arylalkyl, arylalkoxy, C 7-12 alkylaryl, C 3-12 Heterocyclic alkyl, C 3-12 heteroaryl, C 1-6 alkylsulfonyl (-S(O)2-alkyl) and / or C 6-12 Arylsulfonyl (-S(O)2-aryl).

[0043] Based on the total repeating units in the non-fluorinated polymer adhesive, a first repeating unit containing a detectable marker is present in the non-fluorinated polymer adhesive in an amount of 0.01 to 15 mol%, more typically 0.1 to 10 mol%, and even more typically 0.1 to 5 mol%.

[0044] In some embodiments, the non-fluorinated polymer adhesive may further include a second repeating unit derived from one or more second monomers selected from (meth)acrylates, vinyl aromatic compounds, vinyl ethers, vinyl ketones, and vinyl esters. The second repeating unit does not include a detectable label. The second repeating unit may include any suitable functional group, such as alkyl, ester, aryl, etc.

[0045] Based on the total repeating units in the non-fluorinated polymer adhesive, the second repeating unit may be present in the non-fluorinated polymer adhesive in an amount of 5 to 95 mol%, more typically 10 to 90 mol%, and even more typically 20 to 85 mol%.

[0046] In some embodiments, the non-fluorinated polymer adhesive may further include a third repeating unit comprising a crosslinkable group, a crosslinking group, or a combination thereof. As used herein, a "crosslinkable group" refers to a nucleophilic group comprising oxygen, nitrogen, or sulfur, such as hydroxyl (-OH), carboxyl (-C(O)OH), amino (-NH2), thiol (-SH), vinyl (e.g., C... 2-30 (Alkenyl) or amide (-C(O)NH2). Other examples of crosslinkable groups may include those such as epoxy and lactone, for example, epoxy, -propiolactone, -butyrolactone, or -valproic acid lactone. The crosslinkable group may be attached directly (via a single bond) or through one or more divalent linking groups to the polymerizable group of a third monomer.

[0047] Crosslinking monomers include monomers having two or more polymerizable groups. Useful crosslinking agents include, for example: trivinylbenzene, divinyltoluene; divinylpyridine, divinylnaphthalene, and divinylxylene; and, for example: ethylene glycol diacrylate, trimethylolpropane triacrylate, diethylene glycol divinyl ether, trivinylcyclohexane, allyl methacrylate (“ALMA”), ethylene glycol dimethacrylate (“EGDMA”), diethylene glycol dimethacrylate (“DEGDMA”), propylene glycol dimethacrylate, propylene glycol diacrylate, trimethylolpropane trimethacrylate (“TMPTMA”), divinylbenzene (“DVB”), glycidyl methacrylate, 2,2-dimethylpropane, 1,3-diacrylate, 1,3-butanediol diacrylate, 1,4-butanediol diacrylate, diethylene glycol diacrylate, diethylene glycol dimethacrylate, 1,6-hexanediol diacrylate, 1,6-hexanediol dimethacrylate, tripropylene glycol diacrylate, triethylene glycol dimethacrylate, tetraethylene glycol diacrylate, etc. Acrylates, polyethylene glycol diacrylate, tetraethylene glycol dimethacrylate, polyethylene glycol dimethacrylate, ethoxylated bisphenol A diacrylate, ethoxylated bisphenol A dimethacrylate, polyethylene glycol dimethacrylate, poly(butanediol) diacrylate, pentaerythritol triacrylate, trimethylolpropane triethoxytriacrylate, glycerol propoxytriacrylate, pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, dipentaerythritol monohydroxypentaacrylate, divinylsilane, trivinylsilane, dimethyldivinylsilane, methyltrivinylsilane, diphenyldivinylsilane, divinylphenylsilane, divinylphenylsilane, divinylphenylsilane, tetravinylsilane, tetravinylsilane, dimethylvinyldisiloxane, poly(methylvinylsiloxane), poly(vinylhydrosiloxane), poly(phenylvinylsiloxane), tetra(C1-C8)alkoxyglycourea, such as tetramethoxyglycourea and tetrabutoxyglycourea, and combinations thereof.

[0048] Based on the total repeating units in the non-fluorinated polymer adhesive, the third repeating unit may be present in the non-fluorinated polymer adhesive in an amount of 5 to 50 mol%, more typically 10 to 50 mol%, and even more typically 20 to 50 mol%.

[0049] The electrode material or non-fluorinated polymer binder may further include one or more crosslinking agents, such as crosslinking agents comprising two or more reactive crosslinking agents. Any suitable crosslinking agent can be used, provided that it has at least two, preferably at least three, portions capable of reacting with the functional groups of the non-fluorinated polymer binder. Exemplary crosslinking agents may include phenolic varnish resins, melamine compounds, guanidine compounds, isocyanate-containing compounds, benzocyclobutene, benzoxazine, etc., and typically any of the aforementioned substances has two or more, more typically three or more portions selected from hydroxymethyl, C 1-10 alkoxymethyl and C 2-10 Substituents of acyloxymethyl groups. Examples of suitable crosslinking agents include those shown below:

[0050]

[0051] Crosslinking agents are well known in the art and are commercially available from various sources. When present, the amount of such crosslinking agent can be, for example, from 0.01 to 30% by weight, preferably from 0.01 to 20% by weight, based on the total weight of the non-fluorinated polymer adhesive.

[0052] Adhesive polymers can be prepared using suitable catalysts. Exemplary catalysts include acid catalysts. Examples of free acids include, but are not limited to, sulfonic acids, such as methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid, benzenesulfonic acid, toluenesulfonic acid, dodecylbenzenesulfonic acid, and trifluoromethanesulfonic acid. Suitable nonionic thermal acid generators include, for example, cyclohexyl p-toluenesulfonate, methyl p-toluenesulfonate, cyclohexyl 2,4,6-triisopropylbenzenesulfonate, nitrobenzyl ester, benzoin toluenesulfonate, 2-nitrobenzyl toluenesulfonate, tris(2,3-dibromopropyl)-1,3,5-triazine-2,4,6-trione, alkyl esters of organic sulfonic acids, p-toluenesulfonic acid, dodecylbenzenesulfonic acid, oxalic acid, and phthalic acid. Phosphoric acid, camphor sulfonic acid, 2,4,6-trimethylbenzenesulfonic acid, triisopropylnaphthalene sulfonic acid, 5-nitro-o-toluenesulfonic acid, 5-sulfosalicylic acid, 2,5-dimethylbenzenesulfonic acid, 2-nitrobenzenesulfonic acid, 3-chlorobenzenesulfonic acid, 3-bromobenzenesulfonic acid, 2-fluorooctylnaphthalenesulfonic acid, dodecylbenzenesulfonic acid, 1-naphthol-5-sulfonic acid, 2-methoxy-4-hydroxy-5-benzoylbenzenesulfonic acid and their salts, and combinations thereof. Suitable ionic thermal acid generators include, for example, triethylamine dodecylbenzenesulfonate, ammonium p-toluenesulfonate, sulfonates such as carbocyclic aryl (e.g., phenyl, naphthyl, anthracene, etc.) and heteroaryl (e.g., thienyl) sulfonates, aliphatic sulfonates, and benzenesulfonates.

[0053] Non-fluorinated polymer adhesives can be prepared using any suitable method in the art, including those exemplified in the working examples. For example, non-fluorinated polymer adhesives can be prepared by reacting a first monomer comprising a detectable label, one or more second monomers selected from (meth)acrylates, vinyl aromatic compounds, vinyl ethers, vinyl ketones, and vinyl esters, and optionally a third monomer comprising a crosslinkable group, a crosslinking group, or a combination thereof. For example, one or more monomers corresponding to the polymerization units described herein can be fed in combination or individually using suitable solvents and initiators and polymerized in a reactor. For example, adhesive polymers can be obtained by polymerizing the corresponding monomers under any suitable conditions, such as by heating at an effective temperature, irradiation with photochemical radiation of an effective wavelength, or a combination thereof.

[0054] Each monomer corresponding to the repeating unit described herein independently comprises a polymerizable group having a carbon-carbon unsaturated vinyl group, and is generally optionally self-substituted or unsubstituted C. 2-20 Alkenyl, substituted or unsubstituted norbornel, substituted or unsubstituted (meth)acrylate, substituted or unsubstituted vinyl ether, substituted or unsubstituted vinyl ketone, substituted or unsubstituted vinyl ester, or substituted or unsubstituted vinyl aryl. Typically, the polymerizable group of each monomer is independently a substituted or unsubstituted C10 group. 2-20 Alkenyl, substituted or unsubstituted norbornel, substituted or unsubstituted (meth)acrylic acid, or substituted or unsubstituted vinyl aromatic compounds. Preferably, the polymerizable group of each monomer is independently substituted or unsubstituted (meth)acrylic acid or substituted or unsubstituted vinyl aromatic compounds.

[0055] Adhesive polymers can be prepared using free radical polymerization or living or controlled free radical polymerization techniques, including reversible addition-fragmentation chain transfer polymerization (RAFT), nitrile-oxygen mediated polymerization (NMP), atom transfer radical polymerization (ATRP), etc. The polymerization can be controlled via a chain transfer agent (CTA), including thiocarbonyl sulfides, such as dithioesters, thiocarbamates, xanthates, etc., through a reversible chain transfer process. In some embodiments, adhesive polymers can be generated by reacting selected monomers with a dithioester chain transfer agent and an initiator to produce the adhesive polymer. In some embodiments, the initiator can be light.

[0056] Exemplary chain transfer agents (CTAs) for controlled free radical polymerization include thiocarbonyl thio compounds, such as 2-cyano-2-propylbenzodithiocarbamate, 4-cyano-4-(phenylcarbonthiothio)valerate, 2-cyano-2-propyldodecyltrithiocarbonate, 4-cyano-4-[(dodecylthiothiocarbonyl)thioalkyl]valerate, 2-(dodecylthiocarbonthiothio)-2-methylpropionic acid, cyanomethyldodecyltrithiocarbonate, cyanomethylmethyl(phenyl)aminodithiocarbamate, bis(thiobenzoyl)disulfide, bis(dodecylthio-thiocarbonyl)disulfide, etc.

[0057] Examples of initiators include azobis(isobutyronitrile) (AIBN), azobis(2-methylbutyronitrile), azobis(2,4-dimethylpentanitrile), and azobis(4-cyanopentanoic acid). Examples of peroxide and peroxy initiators include hydrogen peroxide, sodium peroxide, potassium peroxide, tert-butyl hydroperoxide, cumene hydroperoxide, dilauroyl peroxide, tert-butyl neodecanoate peroxide, benzoyl peroxide, cumyl peroxide, tert-butyl peroxy-2-ethylhexanoate, tert-butyl peroxyacetate, and tert-butyl peroxybenzoate. Examples of other initiators include ammonium and / or alkali metal persulfates, sodium perborate, superphosphate and its salts, potassium permanganate, and ammonium or alkali metal salts of persulfate, such as alkali metal or ammonium persulfates, diacetyl peroxide, benzoyl peroxide, succinyl peroxide, di-tert-butyl peroxide, tert-butyl perbenzoate, tert-butyl perpentanoate, tert-butyl peroxy-2-ethylhexanoate, tert-butyl permaleate, cumene hydroperoxide, diisopropyl peroxycarbamate, bis(o-toluyl)peroxide, bisdecyl peroxide, bisoctyl peroxide, bislauryl peroxide, tert-butyl perisobutyrate, tert-butyl peracetate, di-tert-pentyl peroxide, tert-butyl hydroperoxide, azobisisobutyronitrile, 2,2′-azobis(2-amidinyl-propane) dihydrochloride, or 2,2′-azobis(2-methylbutyronitrile). Mixtures of these initiators are also suitable. As initiators, reduction / oxidation (i.e., redox) initiator systems can also be used. A redox initiator system consists of at least one reducing agent, typically inorganic, and one organic or inorganic oxidizing agent. The oxidizing component includes, for example, polymerization initiators already specified above. The reducing component includes, for example, alkali metal salts of sulfurous acid, such as sodium sulfite, sodium bisulfite, alkali metal salts of disulfite, such as sodium disulfite, bisulfite addition compounds of aliphatic aldehydes and ketones, such as acetone bisulfite, or reducing agents, such as hydroxymethyl sulfinic acid and its salts, or ascorbic acid. Redox initiator systems can be used with soluble metal compounds whose metal components can exist in multiple valence states. Typical redox initiator systems are, for example, ascorbic acid / ferric(II) sulfate / sodium persulfate, tert-butyl hydroperoxide / sodium disulfite, and tert-butyl hydroperoxide / sodium hydroxymethyl sulfinate. Individual components, such as reducing components, can also be mixtures, an example being a mixture of sodium hydroxymethyl sulfinate and sodium disulfite.

[0058] Nitrogen oxide-mediated polymerization (NMP) using stable nitroxide radicals or alkoxyamines as initiators can also be used to prepare adhesive polymers. Examples of suitable initiators for NMP include N-tert-butyl-N-(2-methyl-1-phenylpropyl)-O-(1-phenylethyl)hydroxylamine, N-tert-butyl-O-[1-[4-(chloromethyl)phenyl]ethyl]-N-(2-methyl-1-phenylpropyl)hydroxylamine, 2,2,5-trimethyl-4-phenyl-3-azahexane-3-nitrooxy, 2,2,6,6-tetramethyl-1-piperidinoxy (TEMPO), etc.

[0059] Adhesive polymers can also be prepared using atom transfer radical polymerization (ATRP). Suitable initiators for ATRP include tert-butyl α-bromoisobutyrate, α-bromoisobutyryl bromide, dodecyl 2-bromoisobutyrate, ethyl α-bromoisobutyrate, methyl α-bromoisobutyrate, and octadecyl 2-bromoisobutyrate. Suitable catalysts for ATRP include copper chloride (I), copper chloride (II), copper bromide (I), copper bromide (II), and copper iodide (I). Suitable ligands for ATRP include tris(2-pyridylmethyl)amine, tris[2-(dimethylamino)ethyl]amine, 4,4′-dinonyl-2,2′-bipyridyl, and N,N,N′,N″,N″-pentamethyldiethylenetriamine.

[0060] The initiator can be used at a molar ratio of 0.05 to 2 relative to the chain transfer agent. In an exemplary embodiment, the initiator can be used at a molar ratio of 0.07 to 1 relative to the chain transfer agent.

[0061] The amount of initiator is typically from at least 0.01 or 0.05 or 0.01% by weight to 10 or 5 or 3% by weight, depending on all monomers to be polymerized.

[0062] The polymerization reaction used to prepare the adhesive polymer can be carried out in any suitable solvent, although polymerization can also be carried out without a solvent. Exemplary polymerization solvents include ethers, cyclic ethers, and C445. 5-10 Alkanes, which can be converted into carbon atoms from 1 to 3 carbon atoms. 1-4 Alkyl-substituted C 5-8 Cycloalkanes, aromatic solvents, halogenated hydrocarbon solvents, acetonitrile, dimethylformamide, ethylene carbonate, propylene carbonate, dimethyl sulfoxide, dimethyl sulfone, water, mixtures of these solvents, supercritical solvents (e.g., CO2, where any H can be replaced by F in C) 1-4 Alkanes, etc.) or combinations thereof.

[0063] After polymerization, the resulting binder polymer is separated. The separation step can be performed using known procedures and may include evaporating any residual monomers and / or solvents, precipitating in a suitable solvent, filtering or centrifuging the precipitated polymer, washing the polymer, and drying the washed polymer. Transition metal compounds can be removed by passing them through a column or pad of alumina, silica, and / or clay. Alternatively, transition metal compounds may be oxidized (if desired) and retained in the polymer as stabilizers. When chain-terminating groups are present, they can be cleaved from the binder polymer using any suitable method known in the art. Typically, a suitable C1 solvent can be used. 5-8 Alkanes or C 5-8 Cycloalkanes, such as pentane, hexane, heptane, cyclohexane, or mineral oil, or using C 1-6 Alcohols, such as methanol, ethanol, or isopropanol, or a suitable combination of solvents, can be used for precipitation.

[0064] Weight-average molecular weight (M) of non-fluorinated polymer adhesives w The concentration can be from 2000 g / mol to 100000 g / mol, preferably from 10000 to 50000 g / mol, more preferably from 12000 to 30000 g / mol, and the polydispersity index (PDI) is from 1.3 to 3, preferably from 1.3 to 2, more preferably from 1.4 to 2. The molecular weight is determined by gel permeation chromatography (GPC) using polystyrene standards.

[0065] An electrochemical cell unit is also provided, comprising a cathode, an anode, and an electrolyte located between the cathode and the anode. As described above, Figure 2 A battery pack according to one or more embodiments is shown (e.g. Figure 1 A simplified configuration of the electrochemical cell unit of the battery pack 18).

[0066] In some embodiments, the active material (also referred to as the electroactive material) of the cathode 202 may include a lithium-containing active material capable of lithium intercalation and deintercalation, alloying and dealloying, and / or plating and stripping, while serving as the positive terminal of the electrochemical battery cell 200. The electroactive material of the cathode 202 may include one or more transition metals, such as manganese (Mn), nickel (Ni), cobalt (Co), chromium (Cr), iron (Fe), vanadium (V), or combinations thereof. Exemplary lithium-containing active materials include spinel lithium manganese oxide (LiMn2O4), lithium cobalt oxide (LiCoO2), and nickel manganese oxide spinel (Li(Ni)O2). 0.5 Mn 1.5 (O2), layered nickel-manganese-cobalt oxides (having the general formula xLi2MnO3(1-x)LiMO2, where M is composed of Ni, Mn and / or Co in any proportion). A specific example of layered nickel-manganese oxide spinel is xLi2MnO3(1-x)Li(Ni1 / 3 Mn 1 / 3 Co 1 / 3 )O₂. Other exemplary lithium-containing cathode active materials include Li(Ni 1 / 3 Mn 1 / 3 Co 1 / 3 )O₂), LiNiO₂, Li x ₁₊ₓMn₂₋ₓO₄ (LMO, 0 < x < 1 and 0 < y < 0.1), lithium iron polyanion oxides, such as lithium iron phosphate (LiFePO₄) or lithium iron fluorophosphate (Li₂FePO₄F, LFP) or combinations thereof. Other lithium-containing cathode active materials can also be used, such as LiNi x ₁₋ₓM 1-x ₓO₂ (M consists of any proportion of Al, Co, and / or Mg), LiNi 1-x ₁₋ₓCo 1-y ₓM x+y ₁₊ₓO₂ or LiMn 1.5-x ₁₋ₓNi 0.5-y ₓM x+y ₁₊ₓO₄ (M consists of any proportion of Al, Ti, Cr, and / or Mg), stable lithium manganese oxide spinel (Li x ₁₊ₓMn 2-y ₁₋ₓM y ₁₊ₓO₄, where M consists of any proportion of Al, Ti, Cr, and / or Mg), lithium nickel cobalt aluminum oxide (e.g., LiNi 0.8 ₁₋ₓCo 0.15 ₓAl 0.05 ₁₊ₓO₂ or NCA), aluminum-stabilized lithium manganese oxide spinel (LixMn 2-x ₁₋ₓAl y ₁₊ₓO₄), NCMA (LiNi 1-x-y- z ₁₋ₓCo x ₁₋ₓMn y ₓAl z ₁₊ₓO₂) (where 0.02 ≤ x ≤ 0.20, 0.01 ≤ y ≤ 0.12, 0.01 ≤ z ≤ 0.08), lithium vanadium oxide (LiV₂O₅), Li₂MSiO₄ (M consists of any proportion of Co, Fe, and / or Mn), high-efficiency nickel-manganese-cobalt material (HE-NMC, NMC or LiNiMnCoO₂), olivine LiMn x ₁₋ₓFe (1-x)PO4 (LMFP) and combinations thereof. "Any proportion" means that any element can be present in any amount. In another example, anionic substitution can be performed in the lattice of any example of a lithium transition metal active material to stabilize the crystal structure. For example, any O atom can be replaced by an F atom. In some embodiments, the cathode comprises NCM 111, NCM 532, NCM 622, NCM 712, NCM 811, NCMA, NCA, LNMO, or combinations thereof. In some embodiments, the cathode comprises NCMA.

[0067] In some embodiments, electrolyte 206 serves as a separator to provide a physical barrier between cathode 202 and anode 204. In some embodiments, electrolyte 206 includes a dendrite barrier layer, one or more interface layers, and / or one or more electrolyte layers (not shown separately). In some embodiments, in addition to providing a physical barrier between cathode 202 and anode 204, electrolyte 206 may also facilitate the function of electrochemical cell 200 by providing a path of least resistance for the interior of lithium ions (and associated anions) during lithium-ion cycling.

[0068] Electrolyte 206 provides a medium for the conduction of lithium ions between cathode 202 and anode 204 through electrochemical cell unit 200, and may be in solid, liquid, or gel form. In some aspects, electrolyte 206 may comprise a non-aqueous liquid electrolyte solution comprising a lithium salt dissolved in a non-aqueous proton-inert organic solvent or a mixture of non-aqueous proton-inert organic solvents. Non-limiting examples of lithium salts include lithium hexafluorophosphate (LiPF6), lithium perchlorate (LiClO4), lithium tetrachloroaluminate (LiAlCl4), lithium iodide (LiI), lithium bromide (LiBr), lithium thiocyanate (LiSCN), lithium tetrafluoroborate (LiBF4), lithium tetraphenylborate (LiB(C6H5)4), lithium bis(oxalate)borate (LiB(C2O4)2)(LiBOB), lithium difluorooxalate borate (LiBF2(C2O4)), lithium hexafluoroarsenate (LiAsF6), lithium trifluoromethanesulfonate (LiCF3SO3), lithium bis(trifluoromethane)sulfonylimide (LiN(CF3SO2)2), lithium bis(fluorosulfonyl)imide (LiN(FSO2)2)(LiSFI), and bis(triethylene glycol dimethyl ether)tri(trifluoromethanesulfonyl)sulfonate. Lithium (Li(G3)(TFSI))imide, lithium (LiTFSA) and combinations thereof. Non-limiting examples of non-aqueous proton-inert organic solvents include cyclic carbonates (e.g., ethylene carbonate (EC), propylene carbonate (PC), butene carbonate (BC), fluoroethylene carbonate (FEC)), linear carbonates (e.g., dimethyl carbonate (DMC), diethyl carbonate (DEC), ethyl methyl carbonate (EMC)), aliphatic carboxylic acid esters (e.g., methyl formate, methyl acetate, methyl propionate), γ-lactones (e.g., γ-butyrolactone, γ-valerolactone), chain ethers (e.g., 1,2-dimethoxyethane, 1,2-diethoxyethane, ethoxymethoxyethane), cyclic ethers (e.g., tetrahydrofuran, 2-methyltetrahydrofuran), 1,3-dioxolane), etc.

[0069] In some embodiments, the electrolyte may be a solid electrolyte. The solid electrolyte may include one or more solid electrolyte particles, which may include one or more polymer-containing particles, oxide-containing particles, sulfide-containing particles, halide-containing particles, borate-containing particles, nitride-containing particles, hydride-containing particles, or combinations thereof. Exemplary solid electrolytes include, but are not limited to, LiTi2(PO4)3, LiGe2(PO4)3, and Li7La3Zr2O. 12 ,Li3xLa 2 / 3 -xTiO3,Li3PO4,Li3N,Li4GeS4,Li 10 GeP2S 12 ,Li2S-P2S5,Li6PS5Cl,Li6PS5Br,Li6PS5I,Li3OCl,Li 2.99 Ba0.005 ClO or combinations thereof.

[0070] In some embodiments, the anode 204 includes an electroactive material, such as a lithium host material capable of being used as the negative electrode of the electrochemical battery cell 200. In various aspects, the electroactive material includes lithium and may be lithium metal. In some embodiments, the anode 204 may include an electroactive lithium host material, such as graphite. In some embodiments, the anode 204 may include a conductive material and one or more polymer binder materials to structurally hold the graphite material together. For example, the negative electrode may include the polymer binder disclosed herein.

[0071] The negative electrode may comprise more than or equal to about 50% to less than or equal to about 100% of an electroactive material (e.g., graphite or a mixture of graphite and lithium-ionized silicon oxide), optionally less than or equal to about 30% of a conductive material, and the balance being a binder. For example, in some embodiments, the anode 204 may comprise an active material comprising graphite particles mixed with the binder material. When the binder material is not a non-fluorinated polymer binder containing a detectable label, it may be polyvinylidene fluoride (PVdF), ethylene propylene diene monomer (EPDM) rubber and / or carboxymethoxycellulose (CMC), styrene-butadiene rubber (SBR), compounds and / or mixtures of CMC and SBR, nitrile rubber (NBR), lithium polyacrylate (LiPAA), sodium polyacrylate (NaPAA), sodium alginate, lithium alginate, and combinations thereof, as non-limiting examples. Suitable additional conductive materials may include carbon-containing materials and / or conductive polymers. Carbon-containing materials may include, for example, conductive carbon black, conductive acetylene black, acetylene black, carbon black, graphite, graphene, graphene oxide, carbon nanofibers, carbon nanotubes, etc. Examples of conductive polymers include polyaniline, polythiophene, polyacetylene, polypyrrole, etc. In some respects, mixtures of these conductive materials may be used.

[0072] In some embodiments, the cathode material or the material used to prepare the cathode may include a solvent, a binder, and / or a slurry stabilizer (not shown separately). Depending on the selection of the cathode active material, the solvent may be selected from known materials. For example, the solvent for NCMA active materials may include N-methyl-2-pyrrolidone (NMP). Other solvents may be used, such as cyclic carbonates (e.g., ethylene carbonate (EC), propylene carbonate (PC), butenyl carbonate (BC), fluoroethylene carbonate (FEC)); acyclic (i.e., linear) carbonates (e.g., dimethyl carbonate (DMC), diethyl carbonate (DEC), ethyl methyl carbonate (EMC)); aliphatic carboxylic acid esters (e.g., methyl formate, methyl acetate, methyl propionate); γ-lactones (e.g., γ-butyrolactone, γ-valerolactone); chain ethers (e.g., 1,2-dimethoxyethane, 1,2-diethoxyethane, ethoxymethoxyethane); cyclic ethers (e.g., tetrahydrofuran, 2-methyltetrahydrofuran, 1,3-dioxolane); or combinations thereof.

[0073] The cathode active material can be mixed with an adhesive and / or a conductive filler. In some embodiments, the adhesive used for the cathode active material can be a non-fluorinated polymer adhesive including a detectable marker. In other embodiments, the adhesive used for the cathode active material can be another adhesive, such as polyvinylidene fluoride (PVdF), polyethylene oxide (PEO), ethylene propylene diene monomer (EPDM), carboxymethyl cellulose (CMC), styrene-butadiene rubber (SBR), styrene-butadiene rubber-carboxymethyl cellulose (SBR-CMC), polyacrylic acid (PAA), cross-linked polyacrylic acid-polyethyleneimine, polyimide, polyvinyl alcohol (PVA), sodium alginate, combinations thereof, or other suitable adhesives. Examples of conductive fillers are high surface area carbons, such as acetylene black. The adhesive holds the electrode materials together, and the conductive filler ensures good electronic conduction between the positive current collector and the cathode active material particles.

[0074] In some embodiments, the electrochemical cell unit may further include a separator (not shown). Exemplary separators include polymer membranes, such as polypropylene membranes or coated polypropylene membranes. Separators may include those having the general formula (CH2CH). R ) nThe separator may contain a polyolefin material, wherein R is an alkyl group. In some embodiments, the separator may comprise a single polyolefin or a combination of polyolefins. Examples of polyolefins include polyethylene (PE), polypropylene (PP), polyamide (PA), polytetrafluoroethylene (PTFE), polyvinylidene fluoride (PVdF), polyvinyl chloride (PVC), and / or polyacetylene. Examples of other polymeric materials that may be included in or used to form the separator include cellulose, polyimide, copolymers of polyolefins and polyimide, poly(lithium 4-styrene sulfonate) coated polyethylene, polyetherimide (PEI), bisphenol-acetone phthalic anhydride (BPADA), p-phenylenediamine, poly(m-phenylene isophthalamide) (PMIA), and / or expanded polytetrafluoroethylene reinforced polyvinylidene fluoride-hexafluoropropylene.

[0075] The current collectors for the cathode and / or anode can be any suitable conductive material. For example, current collectors may include copper, nickel, titanium, platinum, gold, silver, magnesium, aluminum, vanadium, their alloys, or combinations thereof. Current collectors can have a thickness from 10 nanometers (nm) to 1000 nm. For example, current collectors can have a thickness of 10 nm to 500 nm, or 50 nm to 400 nm, or 100 nm to 400 nm, but the embodiments are not limited thereto.

[0076] A method for measuring the distribution of a binder in an electrode material is also provided, comprising providing the electrode material disclosed herein; exposing the electrode material to activation radiation sufficient to provide a quantitative signal from a detectable marker; and determining the distribution of a non-fluorinated polymer binder based on the quantitative signal from the detectable marker.

[0077] In some embodiments, the method may further include determining the distribution of a binder in the electrode material before using the electrode material in the operation of the electrochemical battery cell. In other embodiments, the method may also include charging and discharging the electrochemical battery cell, which includes the electrode material, before the step of providing the electrode material. The electrochemical battery cell may be cycled through charging and discharging any number of times before the distribution of the non-fluorinated polymer binder is determined as provided herein.

[0078] In terms of hardware architecture, the determination of the quantitative signal from the detectable marker and the distribution of the non-fluorinated polymer adhesive can be partially achieved using a computing device, which may include a processor, memory, and one or more input and / or output (I / O) device interfaces, communicatively coupled via a local interface. The local interface may include, for example, but not limited to, one or more buses and / or other wired or wireless connections. The local interface may have additional components omitted for simplicity, such as controllers, buffers (caches), drivers, repeaters, and receivers, to enable communication. Furthermore, the local interface may include address, control, and / or data connections to enable appropriate communication between the aforementioned components.

[0079] When a computing device is running, a processor can be configured to execute software stored in memory, transfer data to and from memory, and control the operation of the computing device in general, according to the software. The software in memory is read, in whole or in part, by the processor, possibly buffered within the processor, and then executed. A processor can be a hardware device used to execute software, particularly software stored in memory. A processor can be a custom-designed or commercially available processor, a central processing unit (CPU), an auxiliary processor among several processors associated with the computing device, a semiconductor-based microprocessor (in the form of a microchip or chipset), or any device typically used to execute software.

[0080] Memory can include any one or a combination of volatile memory elements (such as random access memory (RAM, such as DRAM, SRAM, SDRAM, VRAM, etc.) and / or non-volatile memory elements (such as ROM, hard disk drive, CD-ROM, etc.). Furthermore, memory can incorporate electrical, magnetic, optical, and / or other types of storage media. Note that memory can also have a distributed architecture, where various components are geographically separated but accessible to the processor.

[0081] Software in memory can include one or more individual programs, each comprising an ordered list of executable instructions for implementing logical functions. System components embodied as software can also be interpreted as source programs, executable programs (object code), scripts, or any other entity containing a set of instructions to be executed. When constructed as a source program, the program is translated by compilers, assemblers, interpreters, etc., which may or may not be contained in memory.

[0082] It should be noted that any functionality described herein can be embodied in any computer-readable medium for use by or in connection with an instruction execution system, apparatus, or device, such as a computer-based system, a processor-containing system, or other system that can fetch and execute instructions from and from an instruction execution system, apparatus, or device. In the context of this document, a “computer-readable medium” includes, stores, communicates, propagates, and / or transmits programs used by or in connection with an instruction execution system, apparatus, or device. A computer-readable medium can be, for example, but not limited to, electronic, magnetic, optical, electromagnetic, infrared, or semiconductor systems, apparatus, or devices. More specific examples (a non-exhaustive list) of computer-readable media include portable computer disks (magnetic), random access memory (RAM) (electronic), read-only memory (ROM) (electronic), erasable programmable read-only memory (EPROM or flash memory) (electronic), and portable optical disc read-only memory (CDROM) (optical).

[0083] Example

[0084] Example 1

[0085]

[0086] In one example, methyl methacrylate (MMA), butyl acrylate (BA), and acrylate-functionalized RhBUEA (fluorescent tags) can react with each other in a solvent under free radical polymerization conditions and in the presence of AIBN as an initiator. The resulting polymer adhesive includes fluorescent tags as repeating units of the polymer adhesive.

[0087] Figure 3A and 3B The image shown is an exemplary fluorescence image obtained from an electrode comprising the labeled polymer binder prepared in Example 1. The excitation wavelength is 490 nanometers (nm), and the emission wavelength is concentrated around 520 nm. This image can be used to quantitatively determine the distribution of the polymer binder (denoted as "X") in the electrode.

[0088] Throughout this specification, references to "an example," "another example," "an example," etc., mean that a particular element (e.g., feature, structure, and / or characteristic) described in connection with that example is included in at least one example described herein and may or may not be present in other examples. Furthermore, it should be understood that any element described in any example may be combined in various examples in any suitable manner unless the context explicitly indicates otherwise.

[0089] The terms “a” and “an” do not indicate a limitation of quantity, but rather that at least one of the referenced items is present. The term “or” means “and / or”, unless the context clearly indicates otherwise. A reference to “an aspect” throughout the specification means that a particular element (e.g., feature, structure, step, or characteristic) described in connection with that aspect is included in at least one aspect described herein and may or may not be present in other aspects. Furthermore, it should be understood that the described elements may be combined in any suitable manner across the aspects.

[0090] When an element, such as a layer, film, region, or substrate, is referred to as being "on" another element, it can be directly on the other element, or there may be intermediate elements present. Conversely, when an element is referred to as being "directly on" another element, there are no intermediate elements present.

[0091] Unless otherwise stated herein, all test standards are the most recent valid standards as of the filing date of this application, or, if priority is claimed, the filing date of the earliest priority application in which the test standard appears. Unless otherwise defined, the technical and scientific terms used herein have the same meanings as commonly understood by one of ordinary skill in the art to which this disclosure pertains.

[0092] While the foregoing disclosure has been described with reference to exemplary embodiments, those skilled in the art will understand that various changes can be made and equivalents can replace its elements without departing from its scope. Furthermore, many modifications can be made to adapt particular situations or materials to the teachings of this disclosure without departing from its essential scope. Therefore, it is intended that this disclosure be limited to the specific embodiments disclosed, but will include all embodiments falling within its scope.

Claims

1. An electrode material, comprising: Active materials; Non-fluorinated polymer adhesives containing detectable markers; as well as Conductive filler.

2. The electrode material according to claim 1, wherein, The non-fluorinated polymer adhesive comprises a first repeating unit derived from a first monomer containing the detectable marker.

3. The electrode material according to claim 1, wherein, The non-fluorinated polymer adhesive further comprises: The second repeating unit is derived from one or more second monomers selected from (meth)acrylates, vinyl aromatic compounds, vinyl ethers, vinyl ketones and vinyl esters; Crosslinkable groups, crosslinking groups or combinations thereof; or Their combination.

4. The electrode material according to claim 1, wherein, The detectable markers include fluorescein or its derivatives, rhodamine or its derivatives, acridine or its derivatives, coumarin or its derivatives, eosin or its derivatives, erythrosine or its derivatives, pyrene or its derivatives, or combinations thereof.

5. The electrode material according to claim 1, wherein, The non-fluorinated polymer adhesive is prepared by free radical polymerization of the following substances: The first monomer contains the detectable marker; One or more second monomers selected from (meth)acrylates, vinyl aromatic compounds, vinyl ethers, vinyl ketones, and vinyl esters, and Optionally, a third monomer may be included, comprising a crosslinkable group, a crosslinkable group, or a combination thereof.

6. An electrochemical battery cell, comprising: Positive electrode; negative electrode; as well as Electrolytes, Wherein, at least one of the positive electrode or negative electrode comprises the electrode material according to claim 1.

7. A method for measuring the distribution of binder in an electrode material, the method comprising: Provide the electrode material according to claim 1; Expose the electrode material to activation radiation sufficient to provide a quantitative signal from the detectable marker; as well as The distribution of non-fluorinated polymer adhesives is determined based on quantitative signals from detectable markers.

8. The method of claim 7, further comprising charging and discharging the electrochemical cell containing the electrode material prior to the step of providing the electrode material.

9. The method according to claim 7, wherein, The non-fluorinated polymer adhesive comprises a first repeating unit derived from a first monomer containing the detectable marker.

10. The method according to claim 7, wherein, The non-fluorinated polymer adhesive further comprises: The second repeating unit is derived from one or more second monomers selected from (meth)acrylates, vinyl aromatic compounds, vinyl ethers, vinyl ketones and vinyl esters; A third repeating unit comprising a crosslinkable group, a crosslinkable group, or a combination thereof; or Their combination.

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