Liquid composition for producing electrode composite material, method for producing electrode, and method for producing electrochemical element

Patent metadata

Field	Value
Publication number	US-11380884-B2
Application number	US-201916727999-A
Country	US
Kind code	B2
Filing date	Dec 27, 2019
Priority date	Jan 8, 2019
Publication date	Jul 5, 2022
Grant date	Jul 5, 2022

Abstract

A liquid composition for an electrode composite material is provided. The liquid composition comprises an active material, a dispersion medium, and a polymerizable compound. A viscosity of the liquid composition at 25 degrees C. is a viscosity at which the liquid composition is dischargeable from a liquid discharge head.

First claim

The invention claimed is:

1. A liquid composition suitable for an electrode composite material, the composition comprising:
an active material comprising of graphite having a mode diameter of 0.5 um or more;
a dispersion medium: and
a polymerizable compound,
wherein a viscosity of the liquid composition at 25° C. is in a range of from 9.5 to 50 mPas,
the polymerizable compound consists of (i) at least one polymerization initiator and/or catalyst, (ii) at least one acrylate, methacrylate, urethane acrylate resin, vinyl ester resin, unsaturated polyester, epoxy resin, oxetane resin, vinyl ether, a resin utilizing an ene-thiol reaction, or a mixture of two or more of any of these, and optionally (i) at least one sensitizing dye,
the polymerization initiator functions substantially only as a polymerization initiator of polymerizable groups of monomers of the polymerizable compound: and
wherein a 10% diameter (D10) of said graphite active material is 0.1 um or more, and 0.8 um or less.

2. The composition of claim 1 , wherein the active material is capable of being reversibly intercalated or de intercalated with an alkali metal ion.

3. The composition of claim 1 , wherein a proportion of the active material in the liquid composition is 20% by mass or more.

4. The composition of claim 1 , wherein the active material has a maximum particle diameter equal to or smaller than a nozzle diameter of the liquid discharge head.

5. The composition of claim 1 , wherein the active material has a mode diameter of 3 μm or less.

6. The composition of claim 1 , wherein the dispersion medium comprises a porogen.

7. A method for producing an electrode, the method comprising:
applying the composition of claim 1 to an electrode substrate.

8. A method for producing an electrochemical element, the method comprising:
producing an electrode by the method of claim 7 .

9. The composition of claim 1 , wherein the polymerizable compound comprises an ester obtained by:
epoxidizing a double bond of a terpene comprising an unsaturated bond, to obtain an epoxide; and
adducting acrylic acid and/or methacrylic acid to the epoxide, to obtain the acrylate and/or methacrylate of the polymerizable compound.

10. The composition of claim 9 , wherein the terpene comprises myrcene, carene, ocimene, pinene, limonene, camphene, terpinolene, tricyclene, terpinene, fenchene, phellandrene, sylvestrene, sabinene, dipentene, bomene, isopulegol, and/or carvone.

11. The composition of claim 9 , wherein the terpene-derived alcohol comprises citronellol, pinocampheol, geraniol, fenchyl alcohol, nerol, borneol, linalool, menthol, terpineol, thujyl alcohol, citronellal, ionone, irone, cinerol, citral, pinol, cyclocitral, carvomenthone, ascaridole, safranal, piperitol, menthene monool, dihydrocarvone, carveol, sclareol, manool, hinokiol, ferruginol, totarol, sugiol, farnesol, patchouli alcohol, nerolidol, carotol, cadinol, lanceol, eudesmol, and/or phytol.

12. The composition of claim 1 , wherein the polymerizable compound comprises an ester of a terpene-derived alcohol with acrylic acid and/or methacrylic acid, as the acrylate and/or methacrylate of the polymerizable compound.

13. The composition of claim 1 , wherein the polymerizable compound comprises citronellic acid, hinokiic acid, and santalic acid.

14. The composition of claim 1 , wherein the polymerizable compound comprises an acrylate and/or methacrylate comprising a side chain comprising a menthone, carvotanacetone, phellandral, pimelitenone, perillaldehyde, thujone, calone, dageton, camphor, bisabolene, santalene, zingiberene, caryophyllene, curcumene, cedrene, cadinene, longifolene, sesquibenihene, cedrol, guaiol, kessoglycol, cyperone, eremophilone, zerumbone, camphorene, podocarprene, mylene, phyllocladene, totalene, ketomanoyl oxide, manoyl oxide, abietic acid, pimaric acid, neoabietic acid, levopimaric acid, iso-d-pimaric acid, agathene dicarboxylic acid, rubenic acid, carotenoid, peryl aldehyde, piperitone, ascaridole, pimene, fenchene, a sesquiterpene, a diterpene, or a triterpene backbone.

15. The composition of claim 1 , wherein the dispersion medium comprises dipropylene glycol monomethyl ether, diethylene glycol monomethyl ether, ethylene glycol monobutyl ether, γ-butyrolactone, propylene carbonate, and/or N,N-dimethylacetamide.

16. The composition of claim 1 , wherein the active material comprises natural graphite, or synthetic graphite.

17. The composition of claim 1 , wherein the monomers of the polymerizable compound consist of the acrylate, methacrylate, urethane acrylate resin, vinyl ester resin, unsaturated polyester, epoxy resin, oxetane resin, vinyl ether, a resin utilizing an ene-thiol reaction, or a mixture of two or more of any of these.

18. The composition of claim 1 , wherein the polymerization initiator is an organic compound.

19. The composition of claim 1 , wherein said mode diameter is from 0.5 μm to 3 μm.

20. The composition of claim 1 , wherein said dispersion medium is a porogen that is capable of dissolving said polymerizable compound and phase-separating a resulting polymer of polymerization of said polymerizable compound.

21. A liquid composition suitable for an electrode composite material, the composition comprising:
an active material comprising of graphite having a mode diameter of 0.5 um or more:
a dispersion medium: and
a polymerizable compound,
wherein a viscosity of the liquid composition at 25° C. is in a range of from 9.5 to 50 mPas,
the polymerization initiator is at least one selected from the group consisting of α-hydroxyacetophenone, α-aminoacetophenone, 4-aroyl-1,3-dioxolane, benzyl ketal, 2,2-diethoxyacetophenone, p-dimethylaminoacetophene, p-dimethylaminopropiophenone, benzophenone, 2-chlorobenzophenone, 4,4′-dichlorobenzophenone, 4,4′-bis(diethylamino)-benzophenone, Michler's ketone, benzil, benzoin, benzyl dimethyl ketal, tetramethylthiuram monosulfide, thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, azobisisobutyronitrile, benzoin peroxide, di-tertbutyl peroxide, (1-hydroxycyclohexyl)-phenylketone, 2-hydroxy-2-methyl-1-phenyl-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropane-1-one, methyl benzoylformate, a benzoin alkyl ether, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butanone-1, 2,2-dimethoxy-1,2-diphenylethane-1-one, bis(η 5 -2,4-cyclopentadiene-1-yl)-bis[2,6-difluoro-3-(1H-pyrrole-1-yl)phenyl] titanium, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropane-1-one, 2-hydroxy-2-methyl-1-phenylpropane-1-one, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide, 1-[4-(2-hydroxyethoxy)phenyl]-2-hydroxy-2-methyl-1-propane-1-one, monoacylphosphine oxide, disacylphosphine oxide, titanocene, fluorescein, anthraquinone, thioxanthone, xanthone, lophine dimer, a trihalomethyl compound, a dihalomethyl compound, an active ester compound, an organic boron compound, a bisazide compound, azobisisobutyronitrile, onium salt, diazonium salt, quinone diazide, organic halide, aromatic sulfonate, bisulfone compound, sulfonyl compounds, sulfonate, sulfonium salt, sulfamide, iodonium salt, sulfonyl diazomethane compound, and a mixture of two or more of these photoradical generators or thermal polymerization initiators, or photoacid generators; and
wherein a 10% diameter (D10) of said graphite active material is 0.1 um or more, and 0.8 um or less.

Assignees

• Ricoh Co Ltd

Inventors

• Nakajima Satoshi
• Hibino Eiko
• Kuriyama Hiromichi
• Takauji Keigo
• Ohkimoto Miku
• Takeuchi Shigeo
• Masuzawa Masahiro

Classifications

• H01M4/1391

  of electrodes based on mixed oxides or hydroxides, or on mixtures of oxides or hydroxides, e.g. LiCoOx · CPC title

• H01M10/0525

  Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries · CPC title

• H01M4/362 Primary

  Composites · CPC title

• H01M4/1397 Primary

  of electrodes based on inorganic compounds other than oxides or hydroxides, e.g. sulfides, selenides, tellurides, halogenides or LiCoFy · CPC title

• H01M4/622

  being polymers · CPC title