US20160200850A1 - Agent for dispersing electrically conductive carbon material, and dispersion of electrically conductive carbon material - Google Patents

Agent for dispersing electrically conductive carbon material, and dispersion of electrically conductive carbon material Download PDF

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US20160200850A1
US20160200850A1 US14/915,087 US201414915087A US2016200850A1 US 20160200850 A1 US20160200850 A1 US 20160200850A1 US 201414915087 A US201414915087 A US 201414915087A US 2016200850 A1 US2016200850 A1 US 2016200850A1
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Prior art keywords
carbon material
conductive carbon
electrically conductive
dispersion
polymer
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Tatsuya Hatanaka
Yuki Shibano
Takuji Yoshimoto
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Nissan Chemical Corp
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Nissan Chemical Corp
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Assigned to NISSAN CHEMICAL INDUSTRIES, LTD. reassignment NISSAN CHEMICAL INDUSTRIES, LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HATANAKA, TATSUYA, SHIBANO, YUKI, YOSHIMOTO, TAKUJI
Publication of US20160200850A1 publication Critical patent/US20160200850A1/en
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    • C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
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Definitions

  • Lithium ion secondary batteries have a structure in which a container houses a positive electrode and a negative electrode capable of intercalating and deintercalating lithium and a separator interposed between the electrodes, and is filled with an electrolyte solution (in the case of lithium ion polymer secondary batteries, a gel-like or completely solid electrolyte instead of a liquid electrolyte solution).
  • the positive electrode and negative electrode are generally formed by coating a composition which includes an active material capable of intercalating and deintercalating lithium, an electrically conductive material consisting primarily of a carbon material and a polymer binder onto a current collector such as copper foil or aluminum foil.
  • the binder is used to bond the active material with the conductive material, and also to bond these with the metal foil.
  • binders of this type include, for example, N-methylpyrrolidone (NMP)-soluble fluoropolymers such as polyvinylidene fluoride (PVdF), and aqueous dispersions of olefin polymers.
  • lithium ion secondary batteries also show promise as a power source for electric vehicles and the like, and so there is a desire that such batteries have a longer life and better safety than has hitherto been achieved.
  • the bonding strength of the above binders to the current collector is less than adequate.
  • some of the active material and conductive material separates from the current collector and falls off, causing micro-shorting and variability in the battery capacity.
  • the contact resistance between the electrode mixture and the current collector increases or some of the active material or conductive material separates from the current collector and falls off, leading to a deterioration in the battery capacity and leading also to problems from the standpoint of safety.
  • Patent Document 1 discloses the art of disposing, as a bonding layer between the current collector and the electrode mixture, a conductive layer containing carbon as a conductive filler.
  • This publication indicates that, by using a conductive bonding layer-containing composite current collector (also referred to below simply as a “composite current collector”), the contact resistance between the current collector and the electrode mixture can be decreased, loss of capacity during high-speed discharge can be suppressed, and deterioration of the battery can be minimized.
  • composite current collector also referred to below simply as a “composite current collector”
  • carbon particles are used as the conductive filler, but because carbon particles do not have a bonding action with respect to the current collector, a bonding layer is created using a polymer that serves as a matrix.
  • the bonding strength rises as the polymer content becomes larger.
  • the resistance of the bonding layer rises abruptly. As a result, the resistance of the battery as a whole rises.
  • Patent Document 1 JP-A H09-097625
  • Patent Document 2 JP-A 2000-011991
  • Patent Document 4 JP-A 2009-170410
  • Patent Document 7 WO 2008/139839
  • An agent for dispersing an electrically conductive carbon material consisting of a polymer having a pendant oxazoline group; 2.
  • a method for dispersing an electrically conductive carbon material by using an electrically conductive carbon material-dispersing agent to disperse an electrically conductive carbon material in a solvent the method being characterized in that the conductive carbon material-dispersing agent is a polymer having a pendant oxazoline group; and 17.
  • the conductive carbon material dispersion of the invention because it readily forms a thin-film merely by being coated onto a substrate and the resulting thin-film exhibits a high electrical conductivity, is suitable for the production of conductive thin-films. Moreover, in addition to giving, as noted above, a thin-film having excellent adhesion to the substrate, it is able to reproducibly and efficiently form a large-surface area thin-film by a wet method, making it highly suitable for use in not only energy storage device applications, but also in a broad range of applications as various types of semiconductor materials and electrically conductive materials.
  • X is a polymerizable carbon-carbon double bond-containing group
  • R 1 to R 4 are each independently a hydrogen atom, a halogen atom, an alkyl group of 1 to 5 carbon atoms which may have a branched structure, an aryl group of 6 to 20 carbon atoms or an aralkyl group of 7 to 20 carbon atoms.
  • the polymerizable carbon-carbon double bond-containing group on the oxazoline monomer is not particularly limited, provided it includes a polymerizable carbon-carbon double bond.
  • an acyclic hydrocarbon group containing a polymerizable carbon-carbon double bond is desirable, with alkenyl groups having from 2 to 8 carbon atoms, such as vinyl, allyl and isopropenyl groups being preferred.
  • alkyl groups of 1 to 5 carbons which may have a branched structure include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl and n-pentyl groups.
  • aryl groups of 6 to 20 carbons include phenyl, xylyl, tolyl, biphenyl and naphthyl groups.
  • aralkyl groups of 7 to 20 carbons examples include benzyl, phenylethyl and phenylcyclohexyl groups.
  • concomitant use may be made of monomers other than the oxazoline monomer and the hydrophilic group-bearing (meth)acrylic monomer, provided that doing so does not adversely affect the ability of the resulting oxazoline polymer to disperse conductive carbon materials.
  • the content of oxazoline monomer in the monomer ingredients that can be used to produce the oxazoline polymer employed in the practice of the invention is preferably at least 10 wt %, more preferably at least 20 wt %, and even more preferably at least 30 wt %.
  • the upper limit in the content of oxazoline monomer in the monomer ingredients is 100 wt %, in which case a homopolymer of the oxazoline monomer is obtained.
  • the average molecular weight of the oxazoline polymer is not particularly limited, although a weight-average molecular weight of from 1,000 to 2,000,000 is preferred. When the polymer has a weight-average molecular weight below 1,000, it may have a markedly decreased ability to disperse conductive carbon materials or may even exhibit no such ability. On the other hand, at a weight-average molecular weight greater than 2,000,000, the polymer may be very difficult to handle in dispersion treatment. An oxazoline polymer having a weight-average molecular weight of from 2,000 to 1,000,000 is more preferred.
  • the weight-average molecular weight in this invention is a measured value (polystyrene equivalent) obtained by gel permeation chromatography.
  • the oxazoline polymer used in the invention may be produced by polymerizing the above monomers using a known radical polymerization process such as those described in JP-A H06-32844 and JP-A 2013-72002.
  • oxazoline polymers available as commercial products may be used in the invention.
  • Illustrative examples of such commercial products include Epocros WS-300 (from Nippon Shokubai Co., Ltd.; solids concentration, 10 wt %; aqueous solution), Epocros WS-700 (Nippon Shokubai Co., Ltd.; solids concentration, 25 wt %; aqueous solution), Epocros WS-500 (Nippon Shokubai Co., Ltd.; solids concentration, 39 wt %; water/1-methoxy-2-propanol solution), Poly(2-ethyl-2-oxazoline) (Aldrich), Poly(2-ethyl-2-oxazoline) (Alfa Aesar), and Poly(2-ethyl-2-oxazoline) (VWR International, LLC).
  • the solution may be used directly to form a conductive carbon material dispersion, or it may be prepared as a conductive carbon material dispersion in the target solvent system by solvent displacement.
  • Illustrative examples of fibrous conductive carbon materials include carbon nanotubes (CNTs) and carbon nanofibers (CNFs). From the standpoint of electrical conductivity, dispersibility, availability and the like, CNTs are preferred.
  • CNTs are generally produced by, for example, an arc discharge process, chemical vapor deposition (CVD) or laser ablation.
  • the CNTs used in this invention may be obtained by any of these methods.
  • CNTs are categorized as single-walled CNTs composed of a single cylindrically rolled graphene sheet (abbreviated below as “SWCNTs”), double-walled CNTs composed of two concentrically rolled graphene sheets (abbreviated below as “DWCNTs”), and multi-walled CNTs composed of a plurality of concentrically rolled graphene sheets (abbreviated below as “MWCNTs”).
  • SWCNTs, DWCNTs and MWCNTs may each be used alone or a plurality of these types of CNTs may be used in combination.
  • Examples of layered conductive carbon materials include graphite and graphene.
  • the graphite is not particularly limited. Use may be made of various types of commercially available graphite.
  • Graphene is composed of one atom thick sheets of sp2-bonded carbon atoms and has a beehive-like hexagonal lattice structure composed of the carbon atoms and their bonds.
  • the sheet thickness is reportedly about 0.38 nm.
  • graphene oxide obtained via the treatment of graphite by Hummers' method.
  • the conductive carbon material dispersion of the invention includes the above-described oxazoline polymer (conductive carbon material-dispersing agent), a conductive carbon material and a solvent, and is obtained by dispersing the conductive carbon material in the solvent.
  • water, NMP, DMF, THF, methanol and isopropanol are preferred.
  • solvents may each be used alone, or two or more may be used in admixture.
  • the dispersibility and film formability are good even when hydrophilic solvents such as alcohols, glycol ethers or glycols are used. Moreover, the dispersibility and film formability do not decline even when a mixed solvent of these hydrophilic solvents and water is used or when water alone is used as the solvent.
  • the dispersion may be prepared by mixing together the oxazoline polymer (dispersing agent), conductive carbon material and solvent in any order.
  • dispersion treatment it is preferable to subject a mixture of the oxazoline polymer, conductive carbon material and solvent to dispersion treatment.
  • Such treatment enables the proportion in which the conductive carbon material is dispersed to be further increased.
  • dispersion treatment include mechanical treatment such as wet treatment using a ball mill, bead mill, jet mill or the like, or ultrasonic treatment using a bath-type or probe-type sonicator.
  • the mixing ratio of the oxazoline polymer and the conductive carbon material in the conductive carbon material dispersion of the invention may be set to from 1,000:1 to 1:1,000.
  • the concentration of oxazoline polymer in the dispersion is not particularly limited, provided it is a concentration that enables the conductive carbon material to be dispersed in the solvent. However, the concentration is preferably set to about 0.001 to 30 wt %, and more preferably about 0.002 to 20 wt %.
  • the concentration of conductive carbon material in the dispersion varies according to the mechanical, electrical and thermal characteristics required of the thin-film and may be set as desired, provided at least some portion of the conductive carbon material is individually dispersed.
  • the concentration of conductive carbon material in the dispersion is preferably from about 0.0001 to about 30 wt %, more preferably from about 0.001 to about 20 wt %, and even more preferably from about 0.001 to about 10 wt %.
  • the dispersing agent physically adsorbs to the surface of the conductive carbon material, forming a composite.
  • the conductive carbon material dispersion may include a crosslinking agent that is soluble in the above-described solvent.
  • the crosslinking agent may be a compound that gives rise to a crosslinking reaction with the oxazoline groups on the oxazoline polymer, or may be a compound that is self-crosslinking. From the standpoint of further increasing the solvent resistance of the resulting thin-film, a compound that gives rise to a crosslinking reaction with the oxazoline groups is preferred.
  • the compound that gives rise to a crosslinking reaction with oxazoline groups is not particularly limited, provided it is a compound having two or more functional groups that react with oxazoline groups, such as carboxyl groups, hydroxyl groups, thiol groups, amino groups, sulfinic acid groups and epoxy groups.
  • a compound having two or more carboxyl groups is preferred.
  • Compounds which, under heating during thin-film formation or in the presence of an acid catalyst, form the above functional groups and give rise to crosslinking reactions, such as the sodium, potassium, lithium and ammonium salts of carboxylic acids, may also be used as crosslinking agents.
  • Examples of compounds which give rise to crosslinking reactions with oxazoline groups include the metal salts of synthetic polymers such as polyacrylic acid and copolymers thereof or of natural polymers such as carboxymethylcellulose or alginic acid which give rise to crosslink reactivity in the presence of an acid catalyst, and ammonium salts of these same synthetic polymers and natural polymers which give rise to crosslink reactivity under heating.
  • Sodium polyacrylate, lithium polyacrylate, ammonium polyacrylate, carboxymethylcellulose sodium, carboxymethylcellulose lithium and carboxymethylcellulose ammonium, which give rise to crosslink reactivity in the presence of an acid catalyst or under heating conditions are especially preferred.
  • Such compounds that give rise to crosslinking reactions with oxazoline groups may be acquired as commercial products.
  • commercial products include sodium polyacrylate (Wako Pure Chemical Industries Co., Ltd.; degree of polymerization, 2,700 to 7,500), carboxymethylcellulose sodium (Wako Pure Chemical Industries, Ltd.), sodium alginate (Kanto Chemical Co., Ltd.; extra pure reagent), Aron A-30 (ammonium polyacrylate, from Toagosei Co., Ltd.; solids concentration, 32 wt %; aqueous solution), DN-800H (carboxymethylcellulose ammonium, from Daicel FineChem, Ltd.), and ammonium alginate (Kimica Corporation).
  • self-crosslinking compounds include any of the following which exhibit crosslink reactivity in the presence of an acid catalyst: polyfunctional acrylates, tetraalkoxysilanes, and block copolymers of blocked isocyanate group-containing monomers and monomers having at least one hydroxyl group, carboxyl group or amino group.
  • Such self-crosslinking compounds may be acquired as commercial products.
  • commercial products include polyfunctional acrylates such as A-9300 (ethoxylated isocyanuric acid triacrylate, from Shin-Nakamura Chemical Co., Ltd.), A-GLY-9E (Ethoxylated glycerine triacrylate (EO 9 mol), from Shin-Nakamura Chemical Co., Ltd.) and A-TMMT (pentaerythritol tetraacrylate, from Shin-Nakamura Chemical CO., Ltd.); tetraalkoxysilanes such as tetramethoxysilane (Tokyo Chemical Industry Co., Ltd.) and tetraethoxysilane (Toyoko Kagaku Co., Ltd.); and blocked isocyanate group-containing polymers such as the Elastron Series E-37, H-3, H38, BAP, NEW BAP-15, C-52, F-29, W-11P, MF-9 and MF-25K (DKS Co
  • crosslinking agents may each be used singly or two or more may be used in combination.
  • the conductive carbon material dispersion of the invention may include, as a catalyst for promoting the crosslinking reaction: an acidic compound such as p-toluenesulfonic acid, trifluoromethanesulfonic acid, pyridinium p-toluenesulfonic acid, salicylic acid, sulfosalicylic acid, citric acid, benzoic acid, hydroxybenzoic acid or naphthalenecarboxylic acid, and/or a thermal acid generator such as 2,4,4,6-tetrabromocyclohexadienone, benzoin tosylate, 2-nitrobenzyl tosylate or an alkyl ester of an organic sulfonic acid.
  • an acidic compound such as p-toluenesulfonic acid, trifluoromethanesulfonic acid, pyridinium p-toluenesulfonic acid, salicylic acid, sulfosalicylic acid
  • the conductive carbon material dispersion of the invention may include a matrix polymer.
  • the content thereof within the dispersion is preferably from about 0.0001 to about 99 wt %, and more preferably from about 0.001 to about 90 wt %.
  • matrix polymers include the following thermoplastic resins: fluoropolymers such as polyvinylidene fluoride (PVdF), polytetrafluoroethylene, tetrafluoroethylene-hexafluoropropylene copolymers, vinylidene fluoride-hexafluoropropylene copolymers (P(VDF-HFP)) and vinylidene fluoride-chlorotrifluoroethylene copolymers (P(VDF-CTFE)); polyolefin resins such as polyvinyl pyrrolidone, ethylene-propylene-diene ternary copolymers, polyethylene (PE), polypropylene (PP), ethylene-vinyl acetate copolymers (EVA) and ethylene-ethyl acrylate copolymers (EEA); polystyrene resins such as polystyrene (PS), high-impact polystyrene (HIPS), acrylonit
  • PVdF
  • the matrix polymer is preferably a water-soluble polymer such as sodium polyacrylate, carboxymethylcellulose sodium, water-soluble cellulose ether, sodium alginate, polyvinyl alcohol, polystyrenesulfonic acid or polyethylene glycol.
  • Sodium polyacrylate and carboxymethylcellulose sodium are especially preferred.
  • Such a matrix polymer may be acquired as a commercial product.
  • commercial products include sodium polyacrylate (Wako Pure Chemical Industries Co., Ltd.; degree of polymerization, 2,700 to 7,500), carboxymethylcellulose sodium (Wako Pure Chemical Industries, Ltd.), sodium alginate (Kanto Chemical Co., Ltd.; extra pure reagent), the Metolose SH Series (hydroxypropylmethyl cellulose, from Shin-Etsu Chemical Co., Ltd.), the Metolose SE Series (hydroxyethylmethyl cellulose, from Shin-Etsu Chemical Co., Ltd.), JC-25 (a fully saponified polyvinyl alcohol, from Japan Vam & Poval Co., Ltd.), JM-17 (an intermediately saponified polyvinyl alcohol, from Japan Vam & Poval Co., Ltd.), JP-03 (a partially saponified polyvinyl alcohol, from Japan Vam & Poval Co., Ltd.) and polystyrenesulfonic acid (from Aldrich Co
  • the dispersion of the invention includes a polymer that is intended to serve as a crosslinking agent and/or matrix
  • the dispersion may be prepared by subjecting a mixture composed of at least the conductive carbon material, the conductive carbon material-dispersing agent, the solvent, and the polymer that is intended to serve as a crosslinking agent and/or matrix to mechanical treatment in the form of wet treatment using, for example, a ball mill, bead mill or jet mill, or in the form of ultrasonic treatment using a bath-type or probe-type sonicator. Wet treatment using a jet mill or ultrasonic treatment is especially preferred.
  • the polymer that is to serve as a crosslinking agent or matrix may be added following preparation of the dispersion by the foregoing method.
  • the oxazoline polymer (dispersing agent) included in the conductive carbon material dispersion of the invention not only has an excellent ability to disperse conductive carbon materials, it also has a high adhesion to the current-collecting substrates used in energy storage device electrodes.
  • a conductive thin-film obtained from the conductive carbon material dispersion (conductive thin-film forming composition) of the invention is especially suitable as the conductive bonding layer that is interposed between, and bonds together, the current-collecting substrate and the active material layer making up an energy storage device electrode.
  • a composite current collector consisting of a current-collecting substrate and a conductive bonding layer.
  • This composite current collector can be fabricated by coating the above-described conductive carbon material dispersion (conductive thin film-forming composition) onto a current collecting substrate, then drying the applied dispersion in air or under heating to form a conductive bonding layer.
  • the current-collecting substrate used may be one that is suitably selected from among those which have hitherto been used as current-collecting substrates in electrodes for energy storage devices.
  • use can be made of thin-films of copper, aluminum, nickel, gold, silver and alloys thereof, and also carbon materials, metal oxides, and conductive polymers.
  • the thickness is not particularly limited, although a thickness of from 1 to 100 ⁇ m is preferred in this invention.
  • the thickness of the conductive bonding layer also is not particularly limited. However, taking into account the decrease in internal resistance, a thickness of from 0.05 to 10 ⁇ m is preferred.
  • Examples of the coating method include spin coating, dip coating, flow coating, inkjet printing, spray coating, bar coating, gravure coating, slit coating, roll coating, flexographic printing, transfer printing, brush coating, blade coating and air knife coating. From the standpoint of work efficiency and other considerations, inkjet printing, casting, dip coating, bar coating, blade coating, roll coating, gravure coating, flexographic printing and spray coating are preferred.
  • the temperature during drying under applied heat is preferably from about 50° C. to about 200° C., and more preferably from about 80° C. to about 150° C.
  • An electrode for an energy storage device can be produced by forming an active material layer on the conductive bonding layer of the composite current collector.
  • the active material used here may be any of the various types of active materials that have hitherto been used in electrodes for energy storage devices.
  • chalcogen compounds capable of lithium ion insertion and extraction, lithium ion-containing chalcogen compounds, polyanion compounds, elemental sulfur and sulfur compounds may be used as the positive electrode active material.
  • Illustrative examples of such chalcogen compounds capable of lithium ion insertion and extraction include FeS 2 , TiS 2 , MoS 2 , V 2 O 6 , V 6 O 13 and MnO 2 .
  • lithium ion-containing chalcogen compounds include LiCoO 2 , LiMnO 2 , LiMn 2 O 4 , LiMo 2 O 4 , LiV 3 O 8 , LiNiO 2 and Li x Ni y M 1-y O 2 (wherein M is at least one metal element selected from among cobalt, manganese, titanium, chromium, vanadium, aluminum, tin, lead and zinc; and the conditions 0.05 ⁇ x ⁇ 1.10 and 0.5 ⁇ y ⁇ 1.0 are satisfied).
  • An example of a polyanion compounds is LiFePO 4 .
  • sulfur compounds include Li 2 S and rubeanic acid.
  • alkali metals alkali metals, alkali alloys, at least one elemental substance selected from among group 4 to 15 elements of the periodic table which insert and extract lithium ions, as well as oxides, sulfides and nitrides thereof, and carbon materials which are capable of reversibly inserting and extracting lithium ions.
  • alkali metals include lithium, sodium and potassium.
  • alkali metal alloys include metallic lithium, Li—Al, Li—Mg, Li—Al—Ni, sodium, Na—Hg and Na—Zn.
  • Illustrative examples of at least one elemental substance selected from among group 4 to 15 elements of the periodic table which insert and extract lithium ions include silicon, tin, aluminum, zinc and arsenic.
  • oxides include tin silicon oxide (SnSiO 3 ), lithium bismuth oxide (Li 3 BiO 4 ), lithium zinc oxide (Li 2 ZnO 2 ) and lithium titanium oxide (Li 4 Ti 5 O 12 ).
  • Illustrative examples of sulfides include lithium iron sulfides (Li x FeS 2 (0 ⁇ x ⁇ 3)) and lithium copper sulfides (Li x CuS (0 ⁇ x ⁇ 3)).
  • Exemplary nitrides include lithium-containing transition metal nitrides, illustrative examples of which include Li x M y N (wherein M is cobalt, nickel or copper; 0 ⁇ x ⁇ 3, and 0 ⁇ y ⁇ 0.5) and lithium iron nitride (Li 3 FeN 4 ).
  • Examples of carbon materials which are capable of reversibly inserting and extracting lithium ions include graphite, carbon black, coke, glassy carbon, carbon fibers, carbon nanotubes, and sintered compacts of these.
  • a carbonaceous material may be used as the active material.
  • the carbonaceous material is exemplified by activated carbon, such as activated carbon obtained by carbonizing a phenolic resin, then subjecting the carbonized resin to activation treatment.
  • the active material layer may be formed by applying an electrode slurry containing the above-described active material, binder polymer and, optionally, a solvent onto the conductive bonding layer, then drying in air or under heating.
  • a known material may be suitably selected and used as the binder polymer.
  • binder polymers include electrically conductive polymers such as polyvinylidene fluoride (PVdF), polyvinylpyrrolidone, polytetrafluoroethylene, tetrafluoroethylene-hexafluoropropylene copolymers, vinylidene fluoride-hexafluoropropylene copolymers (P(VDF-HFP)), vinylidene fluoride-chlorotrifluoroethylene copolymers (P(VDF-CTFE)), polyvinyl alcohol, polyimide, ethylene-propylene-diene ternary copolymers, styrene-butadiene rubbers, carboxymethyl cellulose (CMC), polyacrylic acid (PAA) and polyaniline.
  • PVdF polyvinylidene fluoride
  • PVdF polyvinylidene fluoride
  • PVdF polyvinylidene fluor
  • the amount of binder polymer added per 100 parts by weight of the active material is preferably from 0.1 to 20 parts by weight, and more preferably from 1 to 10 parts by weight.
  • the solvent is exemplified by the solvents mentioned above in connection with the oxazoline polymer.
  • the solvent may be suitably selected from among these according to the type of binder, although NMP is preferred in the case of water-insoluble binders such as PVdF, and water is preferred in the case of water-soluble binders such as PAA.
  • the electrode slurry may also contain a conductive additive.
  • conductive additives include carbon black, ketjen black, acetylene black, carbon whiskers, carbon fibers, natural graphite, synthetic graphite, titanium oxide, ruthenium oxide, aluminum and nickel.
  • the method of applying the electrode slurry is exemplified by the same techniques as mentioned above for the conductive bonding layer-forming composition.
  • the energy storage device of the invention is equipped with the above-described electrode. More specifically, it is constructed of at least a pair of positive and negative electrodes, a separator interposed between these electrodes, and an electrolyte, with at least one of the positive and negative electrodes being the above-described energy storage device electrode.
  • this energy storage device is characterized by the use therein of the above-described energy storage device electrode, the separator, electrolyte and other constituent members of the device may be suitably selected for use from among known materials.
  • separator examples include cellulose-based separators and polyolefin-based separators.
  • the electrolyte may be either a liquid or a solid, and moreover may be either aqueous or non-aqueous, the energy storage device electrode of the invention being capable of exhibiting a performance sufficient for practical purposes even when employed in devices that use a non-aqueous electrolyte.
  • Illustrative examples of the electrolyte salt include lithium salts such as lithium tetrafluoroborate, lithium hexafluorophosphate, lithium perchlorate and lithium trifluoromethanesulfonate; quaternary ammonium salts such as tetramethylammonium hexafluorophosphate, tetraethylammonium hexafluorophosphate, tetrapropylammonium hexafluorophosphate, methyltriethylammonium hexafluorophosphate, tetraethylammonium tetrafluoroborate and tetraethylammonium perchlorate; and lithium bis(trifluoromethanesulfonyl)imide and lithium bis(fluorosulfonyl)imide.
  • lithium salts such as lithium tetrafluoroborate, lithium hexafluorophosphate, lithium perchlorate and lithium
  • non-aqueous organic solvents include alkylene carbonates such as propylene carbonate, ethylene carbonate and butylene carbonate, dialkyl carbonates such as dimethyl carbonate, methyl ethyl carbonate and diethyl carbonate, nitriles such as acetonitrile, and amides such as dimethylformamide.
  • alkylene carbonates such as propylene carbonate, ethylene carbonate and butylene carbonate
  • dialkyl carbonates such as dimethyl carbonate, methyl ethyl carbonate and diethyl carbonate
  • nitriles such as acetonitrile
  • amides such as dimethylformamide.
  • the resulting mixture was ultrasonically treated for 30 minutes at room temperature using a probe-type ultrasonicator, after which a solution of 0.33 g of sodium polyacrylate (PAA-Na; Wako Pure Chemical Industries Co., Ltd.; degree of polymerization, 2,700 to 7,500) and 0.11 g of the polyacrylic acid (PAA)-containing aqueous solution Aron A-10H (Toagosei Co., Ltd.; solids concentration, 25.8 wt %) dissolved in 49.46 g of distilled water was mixed therein, thereby preparing Conductive Carbon Material Dispersion G.
  • PAA-Na sodium polyacrylate
  • Aron A-10H Toagosei Co., Ltd.; solids concentration, 25.8 wt %
  • ammonium polyacrylate (PAA-NH 4 )-containing aqueous solution Aron A-30 (Toagosei Co., Ltd.; solids concentration, 31.6 wt %), 0.275 g, and 8 g of a 1% aqueous solution of ammonium alginate (NH 4 alginate) (from Kimica Corporation) were mixed together with 11.73 g of distilled water.
  • the resulting solution was mixed with 20 g of Conductive Carbon Material Dispersion A prepared in Example 1-1, thereby preparing Conductive Carbon Material Dispersion L.
  • the ammonium polyacrylate (PAA-NH 4 )-containing aqueous solution Aron A-30 (Toagosei Co., Ltd.; solids concentration, 31.6 wt %), 0.7 g, and 0.2 g of sodium alginate (Na alginate) (Kanto Chemical Co., Ltd.; extra pure reagent) were mixed together with 49.1 g of distilled water.
  • the resulting solution was mixed with 50 g of Conductive Carbon Material Dispersion I prepared in Example 1-9, thereby preparing Conductive Carbon Material Dispersion N.
  • Polyvinylpyrrolidone (Tokyo Chemical Industry Co., Ltd.; molecular weight, 40,000), 0.5 g, and 49.0 g of distilled water were mixed together, after which 0.5 g of multi-walled CNT's (“NC7000”, from Nanocyl) was mixed therein.
  • NC7000 multi-walled CNT's
  • the resulting mixture was ultrasonically treated for 30 minutes at room temperature using a probe-type ultrasonicator, thereby preparing a conductive carbon material dispersion.
  • a polyacrylamide solution (from Aldrich Co.; weight-average molecular weight, 10,000; solids concentration, 50 wt %), 1.0 g, and 48.5 g of distilled water were mixed together, after which 0.5 g of multi-walled CNT's (“NC7000”, from Nanocyl) was mixed therein.
  • Preparation of a conductive carbon material dispersion was attempted by ultrasonically treating the resulting mixture for 30 minutes at room temperature using a probe-type ultrasonicator. However, aggregates were present in the mixture following treatment and so a uniform dispersion could not be obtained.
  • the sodium polyacrylate (PAA-Na)-containing aqueous solution Aron A-7195 (from Toagosei Co., Ltd.; solids concentration, 19 wt %), 2.63 g, and 46.87 g of distilled water were mixed together, after which 0.5 g of multi-walled CNT's (“NC7000”, from Nanocyl) was mixed therein.
  • Preparation of a conductive carbon material dispersion was attempted by ultrasonically treating the resulting mixture for 30 minutes at room temperature using a probe-type ultrasonicator. However, aggregates were present in the mixture following treatment and so a uniform dispersion could not be obtained.
  • the ammonium polyacrylate (PAA-NH 4 )-containing aqueous solution Aron A-30 (from Toagosei Co., Ltd.; solids concentration, 31.6 wt %), 1.58 g, and 47.92 g of distilled water were mixed together, after which 0.5 g of multi-walled CNT's (“NC7000”, from Nanocyl) was mixed therein.
  • Preparation of a conductive carbon material dispersion was attempted by ultrasonically treating the resulting mixture for 30 minutes at room temperature using a probe-type ultrasonicator. However, aggregates were present in the mixture following treatment and so a uniform dispersion could not be obtained.
  • oxazoline polymers act effectively as dispersing agents for dispersing conductive carbon materials in water.
  • the conductive carbon material dispersion of Example 1-1 was uniformly spread over aluminum foil (thickness, 20 ⁇ m) with a wiper coater (OSP-30 Select-Roller; wet film thickness, 30 ⁇ m), then dried at 120° C. for 20 minutes, thereby producing a conductive thin-film.
  • a wiper coater OSP-30 Select-Roller; wet film thickness, 30 ⁇ m
  • conductive thin-film production was attempted by uniformly spreading the respective conductive carbon material dispersions prepared in Comparative Examples 1-1 and 1-2 on aluminum foil (thickness, 20 ⁇ m) with a wiper coater (SP-30 Select-Roller; wet film thickness, 30 ⁇ m), then drying the applied dispersion.
  • the dispersion was repelled by the aluminum and could not be uniformly spread, as a result of which a conductive thin-film could not be produced.
  • conductive carbon material dispersions containing an oxazoline polymer as the dispersing agent have an excellent film formability on metal such as aluminum.
  • CNT-containing conductive thin-films are often formed on metal and used. Also, given the current trend away from organic solvents, there exists a desire for materials that use water as the solvent.
  • the oxazoline polymer-containing aqueous conductive carbon material dispersions of this invention may be regarded as desirable materials capable of addressing these needs.
  • the conductive thin-film was crosscut at intervals of 1 mm, both vertically and horizontally, to form 100 square boxes, each measuring 1 mm on a side.
  • an adhesion test was carried out by attaching pressure-sensitive adhesive tape (CT-12S2P, from Nichiban Co., Ltd.) to this crosscut area, then peeling off the tape.
  • the adhesion was rated as “Good” when none of the conductive thin-film whatsoever separated from the substrate, and was rated as “NG” when some or all of the crosscut area separated from the substrate.
  • Solvent resistance tests were carried out by bringing cotton swabs impregnated with the respective solvents shown below into contact with the conductive bonding layer and passing the swab back and forth over the layer.
  • the solvent resistance was rated as “Good” when none of the conductive bonding layer separated off, “Fair” when some separation occurred, and “NG” when all of the conductive bonding layer separated off.
  • the conductive bonding layers produced from the dispersions prepared in Examples 1-1 and 1-2 which contained no additives (matrix polymer and crosslinking agent) were found to have a good adhesion to aluminum but a poor solvent resistance (Examples 2-1 and 2-2).
  • the conductive bonding layer produced from the dispersion prepared in Example 1-3 to which PAA-Na had been added that was prepared in Example 1-3 had an improved solvent resistance (Example 2-3).
  • the PAA-Na functions as a matrix polymer, thereby improving the solvent resistance.
  • PAA-NH 4 and NH 4 alginate release ammonia when heated, becoming PAA and alginate acid, each of which has a high reactivity with oxazoline.
  • PAA-Na and Na alginate are capable of reacting with oxazoline in the presence of an acid catalyst (PAA).
  • PAA acid catalyst
  • each of the conductive bonding layers produced using oxazoline polymers showed a high adhesion to the aluminum foil or copper foil serving as the current-collecting substrate and did not separate from the substrate whatsoever. It is apparent from this that, by using the conductive carbon material dispersion of the invention, it is possible to produce an electrode in which a thin-film formed on the current-collecting substrate does not readily fall off and which thus has an excellent durability.
  • Lithium iron phosphate (LFP; available from Tatung Fine Chemicals Co; 17.3 g) as the active material, an NMP solution of PVdF (12 wt %; 12.8 g) as the binder, acetylene black (AB; available as Denka Black from Denki Kagaku Kogyo K.K.; 0.384 g) as the conductive additive and NMP (9.54 g) were mixed together and then treated at 3,500 rpm for 1 minute using a T.K. Robomix (with Homogenizing Disperser model 2.5 (32 mm dia.), from Primix Corporation).
  • a thin-film spin-type high-speed mixer Frmix model 40, from Primix Corporation
  • the electrode slurry thus prepared was uniformly spread by the doctor blade method onto the bonding layer of the current collector of Example 2-1 to a wet film thickness of 200 ⁇ m and subsequently dried, first at 80° C. for 30 minutes, then at 120° C. for 30 minutes, to form an active material layer on the conductive bonding layer. This was pressure-bonded with a roll press, thereby producing an electrode (film thickness, 55 ⁇ m).
  • Electrodes were produced in the same way as in Example 3-1.
  • Example 3-1 Aside from using only aluminum foil (thickness, 20 ⁇ m)—that is, a current-collecting substrate—instead of the composite current collector of Example 2-1, an electrode was produced in the same way as in Example 3-1.
  • Silicon (Si; available as SIE23PB from Kojundo Chemical Laboratory Co., Ltd.; 8.89 g) as the active material, an NMP solution of polyamic acid (PI, the reaction product of 4,4′-diaminodiphenyl ether and 3,3′,4,4′-biphenyltetracarboxylic dianhydride) (15 wt %, 12.5 g) as the binder, acetylene black (AB; available as Denka Black from Denki Kagaku Kogyo K.K.; 0.936 g) as the conductive additive and NMP (7.69 g) were mixed together and then treated at 8,000 rpm for 1 minute using a T.K.
  • PI polyamic acid
  • AB available as Denka Black from Denki Kagaku Kogyo K.K.
  • NMP 7.69 g
  • the electrode slurry thus prepared was uniformly spread by the doctor blade method onto the bonding layer of the composite current collector of Example 2-12 to a wet film thickness of 50 ⁇ m and subsequently dried, first at 80° C. for 30 minutes, then at 120° C. for 30 minutes, to form an active material layer on the conductive bonding layer. This was pressure-bonded with a roll press, then baked in a vacuum at 350° C. for 40 minutes, thereby producing an electrode.
  • Example 3-10 Aside from using only aluminum foil (thickness, 20 ⁇ m)—that is a current-collecting substrate—instead of the composite current collector of Example 2-12, an electrode was produced in the same way as in Example 3-10.
  • Activated carbon (YP-50F, from Kuraray Chemical Co., Ltd.; 11.83 g), as the electrode material, 27.5 g of an aqueous solution (1 wt %) of an ammonium salt of carboxymethylcellulose (abbreviated below as CMC-NH4; available from Daicel Chemical Industries, Ltd.
  • Daicel CMC DN800H Daicel CMC DN800H
  • acetylene black (AB; available as Denka Black from Denki Kagaku Kogyo K.K.) as the conductive additive
  • 13.02 g of distilled water and 1.96 g of a styrene-butadiene copolymer (SBR)-containing aqueous emulsion solution available as TRD2001 from JSR Corporation; solids concentration, 48.5 wt %) were mixed together, and then treated at 5,000 rpm for 3 minutes using a T.K. Robomix (with Homogenizing Disperser model 2.5 (32 mm dia.), from Primix Corporation).
  • a thin-film spin-type high-speed mixer Frmix model 40, from Primix Corporation
  • the electrode slurry thus prepared was uniformly spread by the doctor blade method onto the bonding layer of the composite current collector of Example 2-13 to a wet film thickness of 300 ⁇ m and subsequently dried, first at 80° C. for 30 minutes, then at 120° C. for 30 minutes, to form an active material layer on the conductive bonding layer. This was pressure-bonded with a roll press, thereby producing an electrode (film thickness, 120 ⁇ m).
  • the electrode die-cut in the shape of a disk was then placed on top thereof with the active material-coated side facing down.
  • one drop of electrolyte solution was deposited thereon, after which the coin cell case was placed on top and sealing was carried out with a coin cell crimper.
  • the cell was then placed at rest for 24 hours, giving a secondary battery.
  • Example 4-1 Aside from using the electrode produced in Comparative Example 3-1 instead of the electrode produced in Example 3-1, a secondary battery was produced in the same way as in Example 4-1.
  • the batteries produced in Examples 4-1 to 4-9 had higher voltages and larger discharge capacities when discharged. This is presumably because, in each of the batteries of the Examples, the conductive bonding layer present between the active material layer and the current collector increased the adhesion therebetween, resulting in a lower interfacial resistance between the active material layer and the current collector.
  • a conductive thin-film can easily be formed simply by coating the dispersion onto a substrate, in addition to which the resulting conductive thin-film is suitable as a conductive bonding layer for secondary batteries.
  • secondary batteries having good characteristics can be obtained by using, as an electrode in the secondary battery, especially as a positive electrode in a lithium ion secondary battery, a secondary battery electrode having such a conductive thin-film as a bonding layer.
  • the electrode produced in Example 3-10 was die-cut as a 10 mm diameter disk and the weight was measured, following which the electrode disk was vacuum-dried at 100° C. for 15 hours and then transferred to a glovebox filled with argon.
  • the electrode die-cut in the shape of a disk was then placed on top thereof with the active material-coated side facing down.
  • one drop of electrolyte solution was deposited thereon, after which the coin cell case was placed on top and sealing was carried out with a coin cell crimper.
  • the cell was then placed at rest for 24 hours, giving a secondary battery.
  • Example 4-10 Aside from using the electrode produced in Comparative Example 3-2 instead of the electrode produced in Example 3-10, a secondary battery was produced in the same way as in Example 4-10.
  • Example 4-10 and Comparative Example 4-2 The characteristics of the secondary batteries produced in Example 4-10 and Comparative Example 4-2 were evaluated. Charge-discharge tests were carried out under the following conditions for the purpose of evaluating the stability of the conductive bonding layer in the negative electrode and the effect of the conductive bonding layer on the cell resistance. Table 3 shows the discharge in the 30 th cycle.
  • a secondary battery having good characteristics can be manufactured by employing the conductive bonding layer of the invention in the negative electrode of a lithium ion secondary battery, especially a negative electrode having silicon as the active material.
  • One of the electrodes that had been vacuum-deaerated was set, with the activated carbon-coated surface facing upward, in a 2032 coin cell (Hohsen Corporation) case to which had been welded a washer and a spacer, and a separator was placed on top thereof.
  • the other electrode that had been vacuum-deaerated was then placed on top of the separator, with the activated carbon-coated surface facing downward.
  • three drops of electrolyte solution were deposited thereon, the gasket was placed on top, and a cap to which had been welded a washer and a spacer was placed on top of the gasket, after which sealing was carried out with a coin cell crimper.
  • the cell was then placed at rest for 24 hours, giving a electrical double-layer capacitor.
  • FIG. 1 shows the impedance measurement results.
  • the electrical double-layer capacitors produced in Examples 5-1 and 5-2 had a low cell resistance and a low interfacial resistance compared to the electrical double-layer capacitor produced in Comparative Example 5-1. This is presumably because, in the electrical double-layer capacitors of the Examples, the conductive bonding layer present between the active material layer and the current collector increases their adhesion, as a result of which the interfacial resistance between the active material layer and the current collector decreased.

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