New conductivity enhancer
By incorporating ether, halogen, and hydroxy-containing (meth)acrylic monomer components into conductive materials, the conductivity, flexibility, and durability of these materials are enhanced, addressing the limitations of current technologies.
Patent Information
- Application Number
- JP2021018446
- Authority / Receiving Office
- JP · JP
- Patent Type
- Patents
- Current Assignee / Owner
- Filing Date
- 2021-02-08
- Publication Date
- 2025-04-02
- Estimated Expiration
- 2041-02-08
AI Technical Summary
Current conductive materials face limitations in achieving optimal conductivity due to the specific combinations of conductive components used.
The use of a composition comprising ether moiety-containing, halogen-containing, and hydroxy-containing (meth)acrylic monomer components, optionally with a crosslinking agent, to enhance the conductivity of conductive materials.
This approach significantly improves the conductivity of conductive materials while also enhancing their flexibility and durability.
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Abstract
Description
[Technical field]
[0001] The present disclosure relates to novel conductivity enhancers and related techniques. More particularly, the present disclosure relates to compositions for improving the conductivity of conductive materials, comprising copolymers of compounds including ether moiety-containing (meth)acrylic monomer components, halogen-containing (meth)acrylic monomer components, and hydroxy-containing (meth)acrylic monomer components, and optionally including a crosslinker. [Background technology]
[0002] Various improvements have been made to conductive materials and conductors, but the conductive materials currently available are limited to those containing a specific combination of conductive components. [Prior art documents] [Patent documents]
[0003] [Patent Document 1] JP 2019-102719 A [Patent Document 2] International Publication No. 2015 / 099049 [Patent Document 3] International Publication No. 2019 / 039511 [Patent Document 4] International Publication No. 2017 / 163615 [Patent Document 5] JP 2017-183207 A Summary of the Invention [Means for solving the problem]
[0004] The present disclosure provides conductive materials that include a desired combination of conductive components that enhance the electrical conductivity of the conductive material.
[0005] The present disclosure provides compositions or combinations, various methods of making and using same, for example, for improving the electrical conductivity of electrical conductors, comprising A) at least one compound from a group of ether moiety-containing (meth)acrylic monomer components, B) at least one compound from a group of halogen-containing (meth)acrylic monomer components, and C) at least one compound from a group of hydroxy-containing (meth)acrylic monomer components.
[0006] It is contemplated that one or more features described herein may be provided in combinations other than those specifically stated. Various embodiments and advantages of the present disclosure will be recognized by those skilled in the art upon reading and understanding the following detailed description, if necessary. Effect of the Invention
[0007] The present disclosure provides a technique for improving electrical conductivity by providing an electrical conductivity improver. The present disclosure also improves electrical conductivity while improving flexibility. The present disclosure also produces a conductive material with improved electrical conductivity and durability. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
[0008] The present disclosure will be described below while showing the best mode. Throughout this specification, the expression of the singular form should be understood to include the concept of the plural form, unless otherwise specified. Therefore, the singular article (for example, in the case of English, "a", "an", "the", etc.) should be understood to include the concept of the plural form, unless otherwise specified. In addition, it should be understood that the terms used in this specification are used in the sense commonly used in the field, unless otherwise specified. Therefore, unless otherwise defined, all technical terms and scientific and technical terms used in this specification have the same meaning as commonly understood by those skilled in the art to which this disclosure belongs. In case of conflict, the present specification (including definitions) will take precedence.
[0009] The following provides definitions of terms particularly used in this specification and / or explains basic technical content as appropriate.
[0010] (Definition of terms) In this specification, the electrical conductivity (or resistivity) is measured as follows: Specifically, unless otherwise specified, the measurement object (e.g., a film or the like) is cut into a size of 0.5 cm length × 2.00 cm width × 0.2 cm thickness, and the value measured by a four-terminal measurement method (e.g., Loresta GP (manufactured by Mitsubishi Chemical Analytech Co., Ltd.) can be used, but is not limited to this) is used.
[0011] As used herein, the term "conductive material" refers to any material that is electrically conductive. As used herein, a conductive material is any material that is electrically conductive. -1 Ω cm or less, usually 1.0×10 -2 Ω cm or less, preferably 1.0×10 -3 The conductive material includes, but is not limited to, a material having a resistivity of Ω·cm or less. The conductive material includes a conductive component that provides electrical conductivity. Typically, the conductive material is generally composed of a base material and a conductive component.
[0012] As used herein, "improving electrical conductivity" refers to a significant increase in electrical conductivity when a component of the present disclosure is added to a conductive component or conductive material, compared to when the component is not added. For example, this refers to an improvement in electrical conductivity of at least about 1%, about 2%, about 3%, about 4%, about 5%, about 6%, about 7%, about 8%, about 9%, about 10%, about 15%, about 20%, about 25%, about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95%, or about 99%, and can also be expressed in terms of a decrease in volume resistivity. For example, it means that the volume resistivity is reduced by about 1%, about 2%, about 3%, about 4%, about 5%, about 6%, about 7%, about 8%, about 9%, about 10%, about 15%, about 20%, about 25%, about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95%, or about 99% compared to the comparison target.
[0013] In this specification, the term "substrate", also referred to as a matrix, refers to the basic part of the structure of the conductive material, and corresponds to a base on which the conductive component is arranged. Various polymers can be used as the substrate. When the substrate is a polymer, the substrate may be called a polymer matrix.
[0014] In this specification, the term "conductive component" refers to any component that imparts electrical conductivity. Examples of the conductive component include, but are not limited to, any metal component, metal-based components such as metal oxides and metal carbides, conductive carbon-based components, conductive organic compounds, conductive polymers, and the like.
[0015] In this specification, the term "metal-based component" refers to a component that contains metal atoms in some form as its constituent elements, and is a concept that encompasses not only metal components such as metals, but also components derived from metals (e.g., metal oxides, metal carbides, metal sulfides, etc.).
[0016] As used herein, the term "metallic component" includes a metal or an alloy.
[0017] In this specification, the term "conductive carbon-based component" refers to a conductive material containing carbon. Specific examples thereof include natural graphite such as flake graphite, graphite such as artificial graphite, carbon black such as acetylene black, ketjen black, channel black, furnace black, lamp black, and thermal black, carbon-based materials such as graphene, carbon nanotubes, and fullerene; carbon fiber; and carbon fluoride, but are not limited thereto. Metal carbides are not included in the conductive carbon-based component. The "conductive carbon-based component" may also be referred to as a "carbon-based component".
[0018] In this specification, the term "(meth)acrylic monomer" refers to a monomer containing an acrylic group and / or a methacrylic group, and examples thereof include acrylic acid, methacrylic acid, acrylic acid esters, methacrylic acid esters, acrylic acid amides, and methacrylic acid amides.
[0019] As used herein, "(meth)acrylic" means "acrylic" or "methacrylic", and "(meth)acrylate" means "acrylate" or "methacrylate".
[0020] In this specification, the term "ether moiety-containing (meth)acrylic monomer component group" refers to a group of (meth)acrylic monomers containing at least one ether moiety. In the present disclosure, the compounds of the ether moiety-containing (meth)acrylic monomer component group may be used alone or in combination. Examples of the compounds of the ether moiety-containing (meth)acrylic monomer component group include tetrahydrofurfuryl (meth)acrylate, phenoxyethyl (meth)acrylate, ethoxyethoxyethyl (meth)acrylate, 2-methoxyethyl (meth)acrylate, methoxytriethylene glycol (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, (2-methyl-2-ethyl-1,3-dioxolan-4-yl)methyl (meth)acrylate, (3-ethyloxetan-3-yl)methyl (meth)acrylate, and (5-ethyl-1,3-dioxane-5-yl)methyl (meth)acrylate, but the present disclosure is not limited to these examples. Compounds of the ether moiety-containing (meth)acrylic monomer component class of the present disclosure are sometimes referred to herein as "ether moiety-containing (meth)acrylates."
[0021] In this specification, the term "halogen-containing (meth)acrylic monomer component group" refers to a group of (meth)acrylic monomers containing at least one halogen. In this disclosure, the compounds of the halogen-containing (meth)acrylic monomer component group may be used alone or in combination. Examples of compounds of the halogen-containing (meth)acrylic monomer component group include 2,2,2-trifluoroethyl (meth)acrylate, 2,2,3,3-tetrafluoropropyl (meth)acrylate, 1H,1H,5H-octafluoropentyl (meth)acrylate, and 1H,1H,2H,2H-tridecafluorooctyl (meth)acrylate, but the present disclosure is not limited to these examples. Compounds of the halogen-containing (meth)acrylic monomer component group of this disclosure may be referred to as "halogen-containing (meth)acrylate" in this specification.
[0022] In this specification, the term "hydroxy-containing (meth)acrylic monomer component group" refers to a group of (meth)acrylic monomers containing at least one hydroxy. The hydroxy-containing (meth)acrylic monomer component group may preferably contain a crosslinkable portion. In the present disclosure, one or more compounds of the hydroxy-containing (meth)acrylic monomer component group may be used. Examples of compounds of the hydroxy-containing (meth)acrylic monomer component group include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, and 4-hydroxybutyl (meth)acrylate, but the present disclosure is not limited to only these examples. Compounds of the hydroxy-containing (meth)acrylic monomer component group of the present disclosure may be referred to as "hydroxy-containing (meth)acrylate" in this specification.
[0023] In this specification, the term "unsubstituted alkyl (meth)acrylic monomer component group" refers to a group of monomers containing a (meth)acrylic structure that does not have a substantial functional group (e.g., contains only an alkyl group). In the present disclosure, one or more types of compounds of the unsubstituted (meth)acrylic monomer component group may be used. Examples of compounds of the unsubstituted alkyl (meth)acrylic monomer component group include ethyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, n-octyl (meth)acrylate, nonyl (meth)acrylate, isononyl (meth)acrylate, isodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, and isostearyl (meth)acrylate, but the present disclosure is not limited to only these examples.
[0024] The composition or combination according to the present invention may be in the following forms. (1) The compound of the ether moiety-containing (meth)acrylic monomer component group contains neither a halogen nor a hydroxy group, the compound of the halogen-containing (meth)acrylic monomer component group contains neither an ether moiety nor a hydroxy group, and the compound of the hydroxy-containing (meth)acrylic monomer component group contains neither an ether moiety nor a halogen. (2) One of the two or more monomers contained in the composition or combination according to the present invention (a first monomer) corresponds to two of an ether moiety-containing (meth)acrylic monomer, a halogen-containing (meth)acrylic monomer, and a hydroxyl-containing (meth)acrylic monomer, and the other (a second monomer) is a monomer type to which the first monomer does not belong. (3) One of the three or more monomers contained in the composition or combination according to the present invention (first monomer) corresponds to two of the following: ether moiety-containing (meth)acrylic monomer, halogen-containing (meth)acrylic monomer, and hydroxy-containing (meth)acrylic monomer, the other (second monomer) is a monomer species to which the first monomer does not belong, and the other (third monomer) is the same as one of the monomer species to which the first monomer belongs. In this case, the first monomer is treated as a monomer species to which the third monomer does not belong.
[0025] In this specification, a "crosslinking agent" is a reactive agent that can react with functional groups on a polymer to link the polymers intramolecularly or intermolecularly. Examples of crosslinking agents include formaldehyde, 2,4-tolylene diisocyanate, hexamethylene diisocyanate, polyisocyanate (e.g., hexamethylene diisocyanate-based, etc.), Duranate, etc. TM (manufactured by Asahi Kasei Corporation), but the present disclosure is not limited to these examples.
[0026] As used herein, the term "crosslinking functional group" refers to a functional group capable of forming a crosslinked structure, and the crosslinking functional group can react with a crosslinking agent to form an intermolecular or intramolecular crosslinked structure.
[0027] As used herein, the term "substitutable number" refers to the maximum number of hydrogen atoms that can be substituted when hydrogen atoms on a group are substituted with a substituent, provided that the resulting group is chemically stable.
[0028] In this specification, an alkyl group may be a straight chain or a branched chain. 1~4 Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, and a sec-butyl group, but the present disclosure is not limited to these examples. 1~6 As the alkyl group, for example, 1~4Examples of the alkyl group include an alkyl group having 1 to 10 carbon atoms (C 1~10 As the alkyl group, for example, 1~6 Examples of the alkyl group include an alkyl group having 1 to 18 carbon atoms, an n-octyl group, an n-nonyl group, an isononyl group, a branched nonyl group, an n-decanyl group, and an isodecyl group, but the present disclosure is not limited to these examples. 1~18 As the alkyl group, for example, 1~10 Examples of the alkyl group include an alkyl group, an undecyl group, a lauryl group, a tridecyl group, a myristyl group, a pentadecyl group, a palmityl group, a heptadecyl group, a stearyl group, and an isostearyl group, but the present disclosure is not limited to these examples.
[0029] In this specification, the alkenyl group may be linear or branched. Examples of the alkenyl group having 2 to 6 carbon atoms include, for example, ethenyl, 1-propenyl, 2-propenyl, butenyl, pentenyl, and hexenyl groups, but the present disclosure is not limited to these examples. Examples of the alkenyl group having 2 to 10 carbon atoms include, for example, alkenyl groups having 2 to 6 carbon atoms, heptenyl, octenyl, nonenyl, and decenyl groups, but the present disclosure is not limited to these examples.
[0030] In this specification, examples of the alkoxy group having 1 to 6 carbon atoms include a methoxy group, an ethoxy group, an n-propyloxy group, an isopropyloxy group, an n-butyloxy group, an isobutyloxy group, a tert-butyloxy group, a sec-butyloxy group, an n-pentyloxy group, an isoamyloxy group, an n-hexyloxy group, and an isohexyloxy group, but the present disclosure is not limited to only these examples.
[0031] As used herein, the term "alkoxy-substituted alkyl group" refers to an alkyl group in which one or more hydrogen atoms on the above alkyl group are substituted with an alkoxy group.
[0032] In the present specification, the term "haloalkyl group" refers to an alkyl group in which one or more hydrogen atoms on the alkyl group are substituted with halogen atoms. In addition, the term "perhaloalkyl" refers to an alkyl group in which all hydrogen atoms on the alkyl group are substituted with halogen atoms. A haloalkyl group having 1 to 6 carbon atoms (C 1-6 haloalkyl group), for example, C 1-6 Examples of fluorinated alkyl groups include trifluoromethyl, trifluoroethyl (e.g., 2,2,2-trifluoroethyl), perfluoroethyl, trifluoro n-propyl, tetrafluoropropyl (e.g., 2,2,3,3-tetrafluoropropyl), perfluoro n-propyl, trifluoroisopropyl, perfluoroisopropyl, trifluoro n-butyl, perfluoro n-butyl, trifluoroisobutyl, perfluoroisobutyl, trifluoro tert-butyl, perfluoro tert-butyl, trifluoro n-pentyl, octafluoropentyl (e.g., 2,2,3,3,4,4,5,5-octafluoropentyl), perfluoro n-pentyl, trifluoro n-hexyl, and perfluoro n-hexyl groups, but the present disclosure is not limited to these examples. Haloalkyl groups having 1 to 8 carbon atoms (C 1-8 Haloalkyl groups include C 1-6 Haloalkyl group, or C 1-8 Examples of fluorinated alkyl groups include an undecafluoro n-heptyl group, a perfluoro n-heptyl group, a tridecafluorooctyl group (such as a 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl group), and a perfluoro n-octyl group, but the present disclosure is not limited to these examples.
[0033] As used herein, the term "cycloalkyl group" refers to a monocyclic or polycyclic saturated hydrocarbon group, including those with a bridged structure. For example, "C 3-12 "Cycloalkyl group" means a cyclic alkyl group having 3 to 12 carbon atoms. 6-12Specific examples of the cycloalkyl group include a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, an isobornyl group, a 2-methyl-2-adamantyl group, and a 2-ethyl-2-adamantyl group, but the present disclosure is not limited to these examples. 5-12 Specific examples of cycloalkyl groups include cyclopentyl groups, C 6-12 Examples of the cycloalkyl group include, but are not limited to, the present disclosure. 3-12 Specific examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, and C 5-12 Cycloalkyl groups are preferred. 6-12 "Cycloalkyl group", but the present disclosure is not limited to such examples.
[0034] As used herein, the term "cycloalkenyl group" refers to a monocyclic or polycyclic unsaturated hydrocarbon group containing a double bond, including those with a bridged structure. Examples include those in which one or more of the carbon-carbon bonds of the above-mentioned "cycloalkyl group" are double bonds. For example, "C 3-12 The term "cycloalkenyl group" refers to a cyclic alkenyl group having 3 to 12 carbon atoms. 6-12 Examples of the "cycloalkenyl group" include 1-cyclohexenyl group, 2-cyclohexenyl group, 3-cyclohexenyl group, cycloheptenyl group, cyclooctenyl group, and cyclononenyl group. 3-12 In the case of "cycloalkyl group", cyclopropenyl group, cyclobutenyl group, cyclopentenyl group, C 6-12 A cycloalkenyl group and the like are preferably used. 6-12 "cycloalkenyl group", however, the present disclosure is not limited to such examples.
[0035] In the present specification, "nonaryl heterocycloalkyl" and "nonaryl heterocycle" refer to a cyclic group having 1 to 3 atoms of the same or different types selected from nitrogen, oxygen and sulfur atoms in the ring, and the group may contain one or more unsaturated bonds, but does not contain an aromatic group. For example, "3- to 8-membered nonaryl heterocycloalkyl" refers to a nonaryl heterocycloalkyl having 3 to 8 ring atoms. Specific examples of "nonaryl heterocycloalkyl" include oxiranyl, oxetanyl, pyranyl, pyrrolidinyl, imidazolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, hexamethyleneiminyl, thiazolidinyl, tetrahydrofuranyl, tetrahydropyridinyl, tetrahydropyranyl, 1,3-dioxolanyl, 1,3-dioxanyl, 1,4-dioxanyl, etc., but the present disclosure is not limited to only these examples. The group also includes those having a crosslinked structure.
[0036] In this specification, the term "aryl group" refers to a group that is generated by removing one hydrogen atom from the ring of an aromatic hydrocarbon. For example, a phenyl group (C6H5-) is generated from benzene, a tolyl group (CH3C6H4-) is generated from toluene, a xylyl group ((CH3)2C6H3-) is generated from xylene, and a naphthyl group (C 10 H8-) is induced. 6~14 The term "aryl group" means an aromatic hydrocarbon group having 6 to 14 carbon atoms. 6~14 Specific examples of the "aryl group" include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, an azulenyl group, an acenaphthenyl group, an anthryl group, a fluorenyl group, a phenalenyl group, and a phenanthryl group. 6~18 Specific examples of the "aryl group" include, for example, C 6~14Examples of the aryl group include aryl groups, benzo[a]anthryl groups, benzo[a]fluorenyl groups, benzo[c]phenanthryl groups, chrysenyl groups, fluoranthenyl groups, pyrenyl groups, tetracenyl groups, and triphenylenyl groups. The arylthio group refers to an aryl-S- group. For example, the phenyl-S- group (phenylthio group) and the like can be mentioned, but the present disclosure is not limited to only these examples.
[0037] In the present specification, the term "heteroaryl group" refers to a monocyclic or polycyclic heteroatom-containing aromatic group, which contains one or more (e.g., 1 to 4) of the same or different heteroatoms selected from nitrogen, sulfur, and oxygen atoms. For example, a "5- to 18-membered heteroaryl group" refers to a heteroaryl group having 5 to 18 ring atoms. A "haloheteroaryl group" refers to a group in which one or more hydrogen atoms on a ring atom are replaced with a halogen. Specific examples of the "heteroaryl group" include a pyrrolyl group, a thienyl group, a benzothienyl group, a benzofuranyl group, a benzoxazolyl group, a benzothiazolyl group, a furyl group, an oxazolyl group, a thiazolyl group, an isoxazolyl group, an isothiazolyl group, a benzoisoxazolyl group, a benzoisothiazolyl group, an imidazolyl group, a pyrazolyl group, a pyridyl group, a pyrazyl group, a pyrimidyl group, a pyridazyl group, a quinolyl group, and an isoquinolyl group. Examples of such groups include, but are not limited to, a triazolyl group, a triazinyl group, a tetrazolyl group, an indolyl group, an imidazo[1,2-a]pyridyl group, a pyrazolo[1,5-a]pyridyl group, a [1,2,4]triazolo[1,5-a]pyridyl group, a benzimidazolyl group, a quinoxalyl group, a cinnolyl group, a quinazolyl group, an indazolyl group, a naphthyridyl group, a quinolinolyl group, and an isoquinolinolyl group.
[0038] In the present specification, the term "ether moiety-containing group" refers to a group having an oxygen atom between carbon atoms of an optionally substituted hydrocarbon group, and the group contains one or more (e.g., 1 to 4) oxygen atoms. Specific examples of the "ether moiety-containing group" include, for example, a methoxymethyl group, a methoxyethyl group, a methoxypropyl group, a methoxybutyl group, an ethoxymethyl group, an ethoxyethyl group, an ethoxypropyl group, and an ethoxybutyl group, but the present disclosure is not limited to only these examples.
[0039] In the present specification, the term "halogen-containing group" refers to a group having a halogen atom in a partial structure, and the group contains one or more (e.g., 1 to 4) halogen atoms. Specific examples of the "halogen-containing group" include a trifluoromethyl group, a trifluoroethyl group, a trifluoropropyl group, a trifluorobutyl group, a trichloromethyl group, a trichloroethyl group, a trichloropropyl group, and a trichlorobutyl group, but the present disclosure is not limited to only these examples.
[0040] In the present specification, the term "hydroxy-containing group" refers to a group having a hydroxy group in a partial structure, and the group contains one or more (e.g., 1 to 4) hydroxy groups. Specific examples of the "hydroxy-containing group" include a hydroxymethyl group, a hydroxyethyl group, a hydroxypropyl group, and a hydroxybutyl group, but the present disclosure is not limited to only these examples.
[0041] In general, the term "substituted" refers to the replacement of one or more hydrogen radicals in a given structure with the radical of a particular substituent. It is recognized that the phrase "optionally substituted" is used interchangeably with the phrase "unsubstituted or substituted." For example, "C 1~10 C optionally substituted with an alkyl group 6~18 "Aryl group" means "unsubstituted C 6~18 Aryl group, or C 1~10 C substituted with alkyl group 6~18The term "aryl group" is synonymous with "aryl group." In this specification, the number of substituents in a group defined using "substituted" or "optionally substituted" is not particularly limited, and may be one or more, so long as substitution is possible. In addition, unless otherwise specified, the description of each group also applies to the case where the group is a part or a substituent of another group. The number of carbon atoms in the definition of "substituent" can be expressed by, for example, "C 1-6 " etc. Specifically, "C 1-6 The term "alkyl" is synonymous with an alkyl group having 1 to 6 carbon atoms. In addition, in this specification, when a substituent is not specifically indicated with the term "substituted" or "optionally substituted", it means an "unsubstituted" substituent.
[0042] In this specification, "(meth)acrylate" means acrylate or methacrylate, and acrylate and methacrylate may be used alone or in combination. "(meth)acryloyloxy" means acryloyloxy or methacryloyloxy, and acryloyloxy and methacryloyloxy may be used alone or in combination. "(meth)acrylic acid" means acrylic acid or methacrylic acid, and acrylic acid and methacrylic acid may be used alone or in combination.
[0043] In the present specification, the term "combination" refers to two or more compounds that are intended to be used together when used. The combination of compounds may be provided as one composition, but not all of the compounds in the combination may be included in one composition. They may be provided individually, or some may be provided in the same composition. For example, the combination of the first (meth)acrylate and the second (meth)acrylate described in the present specification, the combination of the first (meth)acrylate, the second (meth)acrylate, and the third (meth)acrylate, and the combination of the second (meth)acrylate, the third (meth)acrylate, and the fourth (meth)acrylate, etc. may be mentioned, but the present disclosure is not limited to only such examples.
[0044] (Basic explanation of conductive materials) The conductive material provided in the present disclosure includes any conductive component available in the art. The conductive material of the present disclosure is characterized in that it contains a composition for improving electrical conductivity (also called a conductivity improver) provided in the present disclosure, thereby improving electrical conductivity.
[0045] The conductive material of the present disclosure may typically include a substrate other than the conductive component. The material of the substrate is not particularly limited, and if the substrate is intended to be peeled off, it is preferable that the substrate is made of a material having releasability or that the substrate is surface-treated.
[0046] (Basic explanation of electrical conductivity enhancer) The composition for improving electrical conductivity (conductivity enhancer) or combination provided in the present disclosure, in one aspect, includes at least an "ether moiety-containing (meth)acrylic monomer", a "halogen-containing (meth)acrylic monomer", and a hydroxy-containing (meth)acrylic monomer. The composition may further include a crosslinker. The composition may further include an unsubstituted alkyl (meth)acrylic monomer, if desired.
[0047] In an exemplary embodiment, one example of a compound of the ether moiety-containing (meth)acrylic monomer component group provided in the present disclosure is represented by the formula (1): [ka] The type of ether-containing group contained, the form of the alkyl group (carbon number, branched or straight chain state, etc.), the form of the cycloalkyl group (carbon number, etc.), the form of the aryl group (carbon number, etc.), methacryloxy (R 1 = methyl), acryloxy (R 1 Regardless of whether the material is a fluorine-containing compound or a fluorine-containing compound (H), all of these compounds improve electrical conductivity.
[0048] In an exemplary embodiment, one example of a compound of the halogen-containing (meth)acrylic monomer component group provided in the present disclosure is represented by the formula (2): [ka] The type of halogen-containing group contained, the form of the alkyl group (carbon number, branched or straight chain state, etc.), the form of the cycloalkyl group (carbon number, etc.), the form of the aryl group (carbon number, etc.), methacryloxy (R 1 = methyl), acryloxy (R 1 Regardless of whether the material is a fluorine-containing compound or a fluorine-containing compound (H), all of these compounds improve electrical conductivity.
[0049] In an exemplary embodiment, one example of a compound of the hydroxy-containing (meth)acrylic monomer component group provided in the present disclosure is represented by the formula (3): [ka] The alkyl group form (carbon number, branched or straight chain state, etc.), the cycloalkyl group form (carbon number, etc.), the aryl group form (carbon number, etc.), methacryloxy (R 1 = methyl), acryloxy (R 1 Regardless of whether the material is a fluorine-containing compound or a fluorine-containing compound (H), all of these compounds improve electrical conductivity.
[0050] The basic method of using the conductivity enhancer is as follows.
[0051] (Conductive components targeted by the conductivity enhancer) The conductive component that the conductivity improver of the present disclosure can target is any component having electrical conductivity.Preferably, metal-based components and conductive carbon-based components are included.More preferably, metal components, carbon black, graphene and carbon nanotubes are included.More preferably, silver and carbon nanotubes are included.
[0052] (General manufacturing method for conductive materials) (1) Method for producing polymer matrix In a representative embodiment, the polymer matrix of the present disclosure can be prepared by heating the monomer and / or by irradiating the monomer with ultraviolet light of a specific illuminance to polymerize it. Such ultraviolet light irradiation can be carried out under conditions set by those skilled in the art. When preparing the polymer matrix by polymerization using ultraviolet light, a complicated drying operation for removing the solvent is not required, and the workability is excellent.
[0053] The wavelength of the ultraviolet light used in the present disclosure may be any wavelength within that range, and an appropriate wavelength may be selected according to the purpose. For example, in the present disclosure, any wavelength may be used as long as it can exert an initial effect on the monomer. Typically, it is a wavelength that can be irradiated by the light source used in the examples. Specifically, a light source of about 150 nm to 400 nm is used, and preferably 300 nm to 400 nm.
[0054] The preferred illuminance of the ultraviolet light used in the present disclosure varies depending on the starting material. The ultraviolet light irradiation device is not particularly limited, and examples thereof include a low pressure mercury lamp, a medium pressure mercury lamp, a high pressure mercury lamp, an ultra-high pressure mercury lamp, a metal halide lamp, a black light lamp, a UV electrodeless lamp, a short arc lamp, and an LED.
[0055] When polymerizing the monomer, it is preferable to use a polymerization initiator. Examples of the polymerization initiator include a thermal polymerization initiator, a photopolymerization initiator, a redox polymerization initiator, an ATRP (atom transfer radical polymerization) initiator, an ICAR ATRP initiator, an ARGET ATRP initiator, a RAFT (reversible addition-fragmentation chain transfer polymerization) agent, an NMP (nitroxide-mediated polymerization) agent, and a polymer polymerization initiator. These polymerization initiators may be used alone or in combination of two or more kinds. Among these polymerization initiators, a photopolymerization initiator is preferable from the viewpoint of not leaving a thermal history in the polymer matrix.
[0056] Examples of the photopolymerization initiator include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,2'-bis(o-chlorophenyl)-4,4',5,5'-tetraphenyl-1,1'-biimidazole, 2,4,6-tris(trichloromethyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(p-methoxyphenylvinyl)-1,3,5-triazine, diphenyliodonium tetrafluoroborate, diphenyliodonium hexafluorophosphate, 4,4'-ditert-butyldiphenylphosphine oxide, and the like. phenyliodonium tetrafluoroborate, 4-diethylaminophenylbenzenediazonium hexafluorophosphate, benzoin, 2-hydroxy-2-methyl-1-phenylpropan-2-one, benzophenone, thioxanthone, 2,4,6-trimethylbenzoyldiphenylacylphosphine oxide, triphenylbutylborate tetraethylammonium, diphenyl-4-phenylthiophenylsulfonium hexafluorophosphate, 2,2-dimethoxy-1,2-diphenylethan-1-one, phenyl Photoradical polymerization initiators such as glyoxylic acid methyl ester, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, 1,2-octanedione, 1-[4-(phenylthio)-2-(o-benzoyloxime)], bis(η5-2,4-cyclopentadiene-1-yl)bis[2,6-difluoro-3-(1H-pyrrol-1-yl)phenyltitanium], 2,4,6-tris(trichloromethyl)-1,3 Examples of photo-induced cationic ring-opening polymerization initiators include, but are not limited to, 2,4-bis(trichloromethyl)-6-(p-methoxyphenylvinyl)-1,3,5-triazine, diphenyliodonium tetrafluoroborate, 4,4'-ditert-butyldiphenyliodonium tetrafluoroborate, 4-diethylaminophenylbenzenediazonium hexafluorophosphate, and diphenyl-4-phenylthiophenylsulfonium hexafluorophosphate, but the present disclosure is not limited to these examples. These photo-induced polymerization initiators may be used alone or in combination of two or more.
[0057] When a photopolymerization initiator is used as the polymerization initiator, the amount of the photopolymerization initiator is usually preferably about 0.01 parts by weight to about 20 parts by weight per 100 parts by weight of the total monomers.
[0058] Examples of the thermal polymerization initiator include azo-based polymerization initiators such as azobisisobutyronitrile (AIBN), 2,2'-azobis(methyl isobutyrate), 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobis(2-methylbutyronitrile), and 1,1'-azobis(cyclohexane-1-carbonitrile), and peroxide-based polymerization initiators such as benzoyl peroxide, potassium persulfate, and ammonium persulfate, but the present disclosure is not limited to these examples. Each of these polymerization initiators may be used alone, or two or more types may be used in combination.
[0059] When a thermal polymerization initiator is used as the polymerization initiator, the amount of the thermal polymerization initiator is usually preferably about 0.01 parts by weight to about 20 parts by weight per 100 parts by weight of the total monomers.
[0060] When a polymerization initiator that generates nitrogen (N2) during the polymerization reaction, such as AIBN, is used, the resulting composite may contain bubbles. Since such bubbles can be the starting point of breakage, the properties of the composite, such as its extensibility, may be reduced, but it is expected that the impact absorption ability may be improved. The bubbles contained in the composite are not limited to those derived from the polymerization initiator, and may be bubbles obtained by a known method that can include bubbles in a resin, such as those obtained by adding a foaming agent or removing a solvent.
[0061] Other polymerization initiators that can be used in the present disclosure include, for example, redox polymerization initiators such as hydrogen peroxide and iron (II) salt, persulfate and sodium hydrogen sulfite, ATRP (atom transfer radical polymerization) initiators using alkyl halides under metal catalysts, ICAR ATRP initiators and ARGET ATRP initiators using metals and nitrogen-containing ligands, RAFT (reversible addition-fragmentation chain transfer polymerization) agents, NMP (polymerization via nitroxide) agents, polymeric polymerization initiators such as polydimethylsiloxane unit-containing polymeric azo polymerization initiators, and polyethylene glycol unit-containing polymeric azo polymerization initiators, but the present disclosure is not limited to only these examples. These polymerization initiators may be used alone or in combination of two or more types.
[0062] When polymerizing a monomer, a chain transfer agent may be used to adjust the molecular weight. The chain transfer agent can usually be used by mixing with the monomer. Examples of the chain transfer agent include α-methylstyrene dimer, 2-(dodecylthiocarbonothioylthio)-2-methylpropionic acid, 2-(dodecylthiocarbonothioylthio)propionic acid, methyl 2-(dodecylthiocarbonothioylthio)-2-methylpropionate, 2-(dodecylthiocarbonothioylthio)-2-methylpropionic acid 3-azido-1-propanol ester, 2-(dodecylthiocarbonothioylthio)-2-methylpropionic acid pentafluorophenyl ester, mercaptan group-containing compounds such as lauryl mercaptan, dodecyl mercaptan, and thioglycerol, and inorganic salts such as sodium hypophosphite and sodium hydrogen sulfite, but the present disclosure is not limited to only these examples. These chain transfer agents may be used alone or in combination of two or more. The amount of the chain transfer agent is not particularly limited, but may usually be about 0.01 to about 10 parts by weight per 100 parts by weight of the total monomers.
[0063] The atmosphere in which the monomer is photopolymerized is not particularly limited, and may be air or an inert gas such as nitrogen gas or argon gas.
[0064] The temperature at which the monomer is photopolymerized is not particularly limited, and is usually preferably about 5 to 100° C. The time required to polymerize the monomer varies depending on the polymerization conditions and cannot be generally determined, so it is optional, but is usually about 1 to 20 hours.
[0065] The polymerization reaction can be terminated at any time when the amount of the remaining monomer becomes 20% by mass or less. The amount of the remaining monomer can be measured, for example, by gel permeation chromatography (GPC).
[0066] By polymerizing the monomers as described above, a polymer matrix can be obtained.
[0067] In one embodiment, the monomers are polymerized in the absence of a crosslinking agent, hi another embodiment, the monomers are polymerized in the presence of a crosslinking agent.
[0068] In one embodiment, the polymer matrix is thermally or photopolymerized. In another embodiment, the polymer matrix is thermally polymerized. In another embodiment, the polymer matrix is photopolymerized.
[0069] Examples of methods for polymerizing a monomer include bulk polymerization, solution polymerization, emulsion polymerization, suspension polymerization, etc., but the present disclosure is not limited to these examples. Among these polymerization methods, bulk polymerization and solution polymerization are preferred.
[0070] The polymerization of the monomer can be carried out by, for example, a radical polymerization method, a living radical polymerization method, an anionic polymerization method, a cationic polymerization method, an addition polymerization method, a polycondensation method, a catalytic polymerization method, or the like.
[0071] When the monomer is polymerized by a solution polymerization method, for example, the monomer can be polymerized by dissolving the monomer in a solvent and adding a polymerization initiator to the resulting solution while stirring the solution, or the monomer can be polymerized by dissolving a polymerization initiator in a solvent and adding the monomer to the resulting solution while stirring the solution. The solvent is preferably an organic solvent compatible with the monomer.
[0072] The copolymers included in the conductive material of the present disclosure may be polymerized by using peroxide-based initiators (eg, benzoyl peroxide, and azobisisobutyronitrile, and analogs thereof) as polymerization initiators.
[0073] When the above-mentioned usable polymerization initiators are used as the polymerization initiator, the amount of the polymerization initiator is usually preferably about 0.01 parts by weight to about 20 parts by weight per 100 parts by weight of the total monomers.
[0074] In one embodiment, the electron beam polymerization is performed by irradiating the monomer with an electron beam. In one embodiment, the monomer can be polymerized by irradiation with an electron beam alone. In the electron beam polymerization, the electron beam is irradiated in the presence of a photopolymerization initiator in one embodiment, and in the absence of a photopolymerization initiator in another embodiment. Either embodiment is within the scope of the present disclosure.
[0075] There is no particular limitation on the polymerization reaction temperature and atmosphere when the monomer is thermally polymerized. Usually, the polymerization reaction temperature is about 50°C to about 120°C. The atmosphere during the thermal polymerization reaction is preferably an inert gas atmosphere such as nitrogen gas. The thermal polymerization reaction time of the monomer varies depending on the polymerization reaction temperature and the like and cannot be determined in general, but is usually about 3 to 20 hours.
[0076] (2) A method for manufacturing the polymer matrix contained in the conductive material The polymer (or polymer matrix) contained in the conductive material of the present disclosure can be produced by mixing two or more specific monomers and polymerizing them under appropriate polymerization conditions, using an appropriate additive such as a polymerization initiator as necessary. The conductive component and any other components are then mixed into this polymer matrix and heated to produce the conductive material of the present disclosure. The individual components and specific production conditions of the polymer are described in detail below.
[0077] In one aspect, the present disclosure relates to a method for making a copolymer comprising at least one compound from an ether moiety-containing (meth)acrylic monomer component group, at least one compound from a halogen-containing (meth)acrylic monomer component group, and at least one compound from a hydroxy-containing (meth)acrylic monomer component group.
[0078] In another aspect, the present disclosure provides a method of making a conductive material comprising a copolymer described herein and a conductive component, the method comprising: obtaining a copolymer by polymerizing at least one compound from the group of ether moiety-containing (meth)acrylic monomer components, at least one compound from the group of halogen-containing (meth)acrylic monomer components, and at least one compound from the group of hydroxy-containing (meth)acrylic monomer components; mixing the copolymer and a conductive component to obtain a mixture; and heating the mixture to form a conductive material. The present invention relates to a method comprising the steps of:
[0079] In an exemplary embodiment, at least one compound of the ether moiety-containing (meth)acrylic monomer component group is represented by the formula (1): [ka] wherein R 1 is a hydrogen atom or a methyl group, and R 2is an alkyl, cycloalkyl, or aryl substituted with an alkyloxy, cycloalkyloxy, or aryloxy group; At least one compound of the halogen-containing (meth)acrylic monomer component group is represented by the formula (2) [ka] wherein R 3 is a hydrogen atom or a methyl group, and R 4 is an alkyl, cycloalkyl, or aryl substituted with from 1 to the possible number of the same or different halogen atoms; At least one compound of the hydroxy-containing (meth)acrylic monomer component group is represented by the formula (3) [ka] and R is a third (meth)acrylate represented by 5 is a hydrogen atom or a methyl group, and R 6 is an alkyl, cycloalkyl, or aryl substituted with a hydroxy group.
[0080] One embodiment relates to a method for making a copolymer comprising at least one compound from the ether moiety-containing (meth)acrylic monomer component group, at least one compound from the halogen-containing (meth)acrylic monomer component group, and at least one compound from the hydroxy-containing (meth)acrylic monomer component group.
[0081] In one embodiment, a crosslinking agent is used in conjunction with at least one compound from the hydroxy-containing (meth)acrylic monomer component group.
[0082] One embodiment relates to a method for making a copolymer comprising at least one compound from the ether moiety-containing (meth)acrylic monomer component group, at least one compound from the halogen-containing (meth)acrylic monomer component group, at least one compound from the hydroxy-containing (meth)acrylic monomer component group, and at least one compound from the unsubstituted alkyl (meth)acrylic monomer component group.
[0083] In one embodiment of the present disclosure, the polymerization of the monomers is carried out according to a polymerization method selected from the group consisting of bulk polymerization, solution polymerization, emulsion polymerization, and suspension polymerization. Without wishing to be bound by theory, the monomers of the present disclosure may be polymerized by chain polymerization, step-growth polymerization, or living polymerization.
[0084] (3-1) Preparation of Monomer The ether moiety-containing (meth)acrylic monomers, halogen-containing alkyl (meth)acrylates, hydroxy-containing alkyl (meth)acrylates, crosslinkers, unsubstituted alkyl (meth)acrylates and (meth)acrylic monomers used in the present disclosure may be commercially available, such as from manufacturers exemplified in the examples, or may be prepared according to methods well known to those of skill in the art.
[0085] (3-2) Photopolymerization method In one embodiment, the polymer matrix of the present disclosure is obtained in one step by polymerizing a monomer (including a plurality of monomers) under exposure to light in the presence of a polymerization initiator. In one embodiment, the polymer matrix of the present disclosure can be prepared by irradiating an ether moiety-containing (meth)acrylic monomer, an alkyl (meth)acrylate substituted with a halogen group, and an alkyl (meth)acrylate substituted with a hydroxyl group with ultraviolet light in the presence of a polymerization initiator. A preferred example of the polymerization initiator is 2,4,6-trimethylbenzoyldiphenylphosphine oxide. This step is usually carried out at room temperature for about 2 hours, but is not limited to this and may be carried out for 0.5 to 3 hours, or 0.5 to 24 hours or longer.
[0086] (3-3) Preparation of resin solution In one embodiment, the polymer matrix of the present disclosure obtained by polymerizing monomers is dissolved in a solvent to produce a resin solution. Preferred examples of the solvent include heptane, octane, and limonene.
[0087] (3-4) Preparation method of conductive material In one embodiment, the conductive material is obtained by mixing the resin solution obtained in (3-3) with a conductive component and, if necessary, a dispersant, and heating the resulting mixture. Those skilled in the art can also prepare the conductive material by other methods using the description herein and any method known in the art.
[0088] (Explanation of conductive components) Examples of conductive components that may be targeted by the conductive material of the present disclosure include natural graphite such as flake graphite, graphite such as artificial graphite, carbon black such as acetylene black, ketjen black, channel black, furnace black, lamp black, and thermal black, carbon-based materials such as graphene, carbon nanotubes, and fullerene; conductive fibers such as carbon fibers and metal fibers; carbon fluoride; powders of metal particles such as copper, gold, nickel, tin, aluminum, zinc, iron, and silver; conductive whiskers such as zinc oxide and potassium titanate; conductive metal oxides such as titanium oxide; and organic conductive materials such as polyphenylene derivatives, but the present disclosure is not limited to only these examples. These conductive components may be used alone or in combination of two or more types. Among these conductive components, from the viewpoint of obtaining a conductive film that is excellent in workability and moldability as well as flexibility and elongation, carbon nanotubes, carbon black, graphene, and metal particles are preferred, and carbon nanotubes, carbon black, graphene, and silver particles are more preferred.
[0089] The solid content of the conductive component in the total solid content of the polymer matrix and the conductive component cannot be determined in general because it varies depending on the type of the conductive component, etc., but from the viewpoint of obtaining a conductive film that is excellent in workability and formability as well as flexibility and extensibility, it is preferably 1 mass % or more, and from the viewpoint of obtaining a conductive film that is excellent in workability and formability as well as flexibility and extensibility, it is preferably 100 mass % or less.
[0090] The content of the solid content of the conductive component in the total solid content of the polymer matrix and the conductive component is preferably 1% by mass or more, more preferably 1.5% by mass or more, and even more preferably 2% by mass or more in the case of a conductive carbon-based component, from the viewpoint of obtaining a conductive film having excellent workability and moldability as well as excellent flexibility and elongation, and is preferably 25% by mass or less, more preferably 20% by mass or less, even more preferably 15% by mass or less, and even more preferably 3.5 to 10% by mass in the case of a conductive carbon-based component, from the viewpoint of obtaining a conductive film having excellent workability and moldability as well as excellent flexibility and elongation. On the other hand, in the case of a metal-based component, from the viewpoint of imparting good conductivity, it is preferably 70% by mass or more, more preferably 75% by mass or more, and even more preferably 80% by mass or more, and from the viewpoint of obtaining a conductive film having excellent workability and moldability, it is preferably 95% by mass or less, more preferably 90% by mass or less, and even more preferably 85% by mass or less.
[0091] (Conductive material applications) The conductive material of the present disclosure can be suitably used as a conductive film that can be suitably used in, for example, sensors, wiring, electrodes, substrates, power generating elements, speakers, microphones, noise cancellers, transducers, artificial muscles, small pumps, medical instruments, and the like used in actuators and industrial robots, and can also be suitably used as a raw material for the conductive film.
[0092] (Preferred embodiment) The preferred embodiments of the present disclosure are described below. The embodiments provided below are provided for a better understanding of the present disclosure, and it is understood that the scope of the present disclosure should not be limited to the following description. Therefore, it is clear that a person skilled in the art can make appropriate modifications within the scope of the present disclosure in light of the description in this specification. It is also understood that the following embodiments of the present disclosure can be used alone or in combination.
[0093] (Applications for improving conductivity) In one aspect, the present disclosure relates to electrical conductivity enhancement applications.
[0094] More specifically, in a specific aspect, the present disclosure provides a composition (conductivity enhancer) or combination for improving the electrical conductivity of an electrical conductor, comprising at least one compound from a group of ether moiety-containing (meth)acrylic monomer components, at least one compound from a group of halogen-containing (meth)acrylic monomer components, and at least one compound from a group of hydroxy-containing (meth)acrylic monomer components.
[0095] In the past, in systems in which a large amount of silver filler is present, as in the present disclosure, it was thought that the polymer composition did not affect the conductivity, and therefore sufficient consideration had not been given to this. However, as a result of polymer consideration, it was confirmed that the resistivity was lower than that of conventional products in a system in which a fluorinated alkyl acrylate, an ether moiety-containing acrylate, and a hydroxyl-containing acrylate were copolymerized. Further investigation confirmed that the resistivity was lower as the fluorine atom content in the fluorinated alkyl acrylate increased. From the viewpoint of resin solubility, it was decided to use 2,2,2-trifluoroethyl acrylate (V#3F) in this system.
[0096] In one specific embodiment, the conductive material of the present disclosure includes a copolymer of an alkoxy-substituted alkyl acrylate, which is an embodiment of an ether moiety-containing (meth)acrylic monomer, a fluorinated alkyl (meth)acrylate, which is an embodiment of a halogen-containing (meth)acrylic monomer, and a hydroxy-containing acrylate, which is an embodiment of a hydroxy-containing (meth)acrylic monomer, and a conductive component. In this way, the copolymer can improve the conductivity of the conductive component.
[0097] By providing this technology of the present disclosure, the conductivity of any conductive component can be improved.
[0098] In one preferred embodiment, the copolymer used in the present disclosure is advantageously a copolymer of an alkoxy-substituted alkyl acrylate, a fluorinated alkyl (meth)acrylate, and a hydroxy-containing acrylate. The reason for this, without wishing to be bound by theory, is the effect of repelling compounds (surface activity effect). Fluorine-based resins are used as antifouling coating agents and release agents, and have the effect of repelling compounds (surface activity effect). As for the reason for the decrease in resistivity in the present disclosure, it is believed that the silver particles are more densely packed together due to the repulsion between the fluorinated alkyl (meth)acrylate and the silver particles caused by the surface activity effect of the fluorine compound. In addition, it is believed that the polarity of the copolymer also affects the decrease in resistivity, and it is believed that these factors have a combined effect, causing the decrease in resistivity. Furthermore, it is an unexpected result that the effect is manifested with a small amount of addition such as in the examples.
[0099] In one embodiment, the conductive component is similar to the conductivity enhancer described above.
[0100] In one embodiment, the compound of the ether moiety-containing (meth)acrylic monomer component group has the formula (1): [ka] wherein R1 is a hydrogen atom or a methyl group, R 2 is an alkyl, cycloalkyl, or aryl substituted with an alkyloxy, cycloalkyloxy, or aryloxy group.
[0101] In one embodiment, R 2 is an alkyl group, a cycloalkyl group, or an aryl group substituted with an alkyloxy group. 2 is an alkyl group, a cycloalkyl group, or an aryl group substituted with a cycloalkyloxy group. 2 is an alkyl group, a cycloalkyl group, or an aryl group substituted with an aryloxy group.
[0102] In one embodiment, the compound represented by formula (1) is an alkyl(meth)acrylate substituted with an alkyloxy group, a cycloalkyloxy group, or an aryloxy group. In one embodiment, the compound represented by formula (1) is an alkyl(meth)acrylate substituted with an alkyloxy group or a cycloalkyloxy group. In one embodiment, the compound represented by formula (1) is an alkyloxy-substituted alkyl(meth)acrylate.
[0103] In one embodiment, the halogen-containing (meth)acrylic monomer component group compound has the formula (2): [ka] wherein R 3 and R 4 is as defined herein.
[0104] In one embodiment, R 4 is an alkyl group, a cycloalkyl group, or an aryl group substituted with a halogen group. 4 is an alkyl group, a cycloalkyl group, or an aryl group substituted with a fluorine atom.4 is an alkyl group, a cycloalkyl group, or an aryl group substituted with a chlorine atom. 4 is an alkyl group, a cycloalkyl group, or an aryl group substituted with a bromine atom.
[0105] In one embodiment, the compound represented by formula (2) is a haloalkyl (meth)acrylate.
[0106] In one embodiment, the hydroxy-containing (meth)acrylic monomer component group compound has the formula (3): [ka] wherein R 5 and R 6 is as defined herein.
[0107] In one embodiment, R 6 is an alkyl group substituted with a hydroxy group. 6 is a cycloalkyl group substituted with a hydroxy group. 6 is an aryl group substituted with a hydroxy group.
[0108] In one embodiment, the compound represented by formula (3) is a hydroxy-substituted alkyl (meth)acrylate. In a preferred embodiment, the compound represented by formula (3) is 4-hydroxybutyl acrylate.
[0109] The hydroxy-containing (meth)acrylates may be used with a corresponding suitable crosslinking agent, such as isocyanate, hexamethylene diisocyanate, polyisocyanate, duranate, etc. TM (manufactured by Asahi Kasei Corporation), but is not limited to these.
[0110] In one embodiment, the alkyl (meth)acrylate substituted with a hydroxy group is used together with a corresponding suitable crosslinking agent as required. In one embodiment, the alkyl (meth)acrylate substituted with a hydroxy group may be used together with a crosslinking agent as required to crosslink. Examples of the crosslinking agent include, but are not limited to, formaldehyde and isocyanate. By using the crosslinking agent together, the durability of the binder resin can be improved, and the flexibility and / or durability of the conductive material can be improved.
[0111] In one embodiment, the unsubstituted alkyl (meth)acrylic monomer component group compound has the formula (4): [ka] wherein R 7 is a hydrogen atom or a methyl group, and R 8 is unsubstituted alkyl, cycloalkyl, or aryl, except that R 8 is not an ether, halogen and hydroxyl substituted alkyl, cycloalkyl, or aryl.
[0112] In one embodiment, R 8 is an unsubstituted alkyl group. In one embodiment, R 8 is an unsubstituted cycloalkyl group. In one embodiment, R 8 is an unsubstituted aryl group.
[0113] In one embodiment, R 8 is an unsubstituted alkyl group having 11 or more carbon atoms. In one embodiment, R 8 is an unsubstituted alkyl group having 11 to 30 carbon atoms. In one embodiment, R 8 is an unsubstituted alkyl group having 11 to 24 carbon atoms.
[0114] In another embodiment, R 8is an unsubstituted alkyl group having 13 or more carbon atoms. In one embodiment, R 8 is an unsubstituted alkyl group having 13 to 30 carbon atoms. In one embodiment, R 8 is an unsubstituted alkyl group having 13 to 24 carbon atoms.
[0115] In yet another embodiment, R 8 is an unsubstituted alkyl group having 18 or more carbon atoms. In one embodiment, R 8 is an unsubstituted alkyl group having 18 to 30 carbon atoms. In one embodiment, R 8 is an unsubstituted alkyl group having 18 to 24 carbon atoms.
[0116] In one embodiment, the compound represented by formula (1) is 2-methoxyethyl acrylate, (3-ethyloxetan-3-yl)methyl acrylate, or 2,3-epoxypropyl methacrylate.
[0117] In one embodiment, the compound represented by formula (1) is 2-methoxyethyl acrylate.
[0118] In one embodiment, the compound represented by formula (2) is 2,2,2-trifluoroethyl acrylate.
[0119] In one embodiment, the compound represented by formula (3) is 4-hydroxybutyl acrylate.
[0120] In one embodiment, an isocyanate is used as a crosslinking agent to crosslink the compound represented by formula (3).
[0121] In one embodiment, the compound represented by formula (4) is isostearyl acrylate, stearyl acrylate, lauryl acrylate, or ethyl acrylate.
[0122] In yet another embodiment, the ether moiety-containing (meth)acrylic monomer is (2-methoxyethyl acrylate, (3-ethyloxetan-3-yl)methyl acrylate, or 2,3-epoxypropyl methacrylate.
[0123] In yet another embodiment, the halogen-containing (meth)acrylate is 2,2,2-trifluoroethyl acrylate.
[0124] In yet another embodiment, the hydroxy-containing (meth)acrylate is 4-hydroxybutyl acrylate.
[0125] In another embodiment, the unsubstituted alkyl (meth)acrylate is isostearyl acrylate, stearyl acrylate, lauryl acrylate, or ethyl acrylate.
[0126] In one preferred embodiment, the compound represented by formula (1) is 2-methoxyethyl acrylate, and the compound represented by formula (2) is 2,2,2-trifluoroethyl acrylate.
[0127] In one preferred embodiment, the compound represented by formula (1) is 2-methoxyethyl acrylate, the compound represented by formula (2) is 2,2,2-trifluoroethyl acrylate, and the compound represented by formula (3) is 4-hydroxybutyl acrylate.
[0128] In one preferred embodiment, the compound represented by formula (1) is 2-methoxyethyl acrylate, the compound represented by formula (2) is 2,2,2-trifluoroethyl acrylate, and the compound represented by formula (3) is 4-hydroxybutyl acrylate, and these acrylates are used or polymerized with a crosslinking agent.
[0129] In one embodiment, the compound represented by formula (1) is 2-methoxyethyl acrylate, the compound represented by formula (2) is 2,2,2-trifluoroethyl acrylate, the compound represented by formula (3) is 4-hydroxybutyl acrylate, and the compound represented by formula (4) is isostearyl acrylate.
[0130] In one preferred embodiment, the compound represented by formula (1) is 2-methoxyethyl acrylate, the compound represented by formula (2) is 2,2,2-trifluoroethyl acrylate, the compound represented by formula (3) is 4-hydroxybutyl acrylate, and the compound represented by formula (4) is isostearyl acrylate, and these acrylates are used or polymerized with a crosslinking agent.
[0131] In one embodiment, the compound represented by formula (1) is 2-methoxyethyl acrylate, the compound represented by formula (2) is 2,2,2-trifluoroethyl acrylate, the compound represented by formula (3) is 4-hydroxybutyl acrylate, and the compound represented by formula (4) is ethyl acrylate.
[0132] In one preferred embodiment, the compound represented by formula (1) is 2-methoxyethyl acrylate, the compound represented by formula (2) is 2,2,2-trifluoroethyl acrylate, the compound represented by formula (3) is 4-hydroxybutyl acrylate, and the compound represented by formula (4) is ethyl acrylate, and these acrylates are used or polymerized with a crosslinking agent.
[0133] In one embodiment, the mass ratio of A) at least one compound of the group of ether moiety-containing (meth)acrylic monomer components, B) at least one compound of the group of halogen-containing (meth)acrylic monomer components, and C) at least one compound of the group of hydroxyl-containing (meth)acrylic monomer components is A:B:C=20-80:80-20:0.2-2.0, can be A:B:C=25-70:70-25:0.3-1.5, and can further be A:B:C=29-65:70-35:0.5-1.5. When a crosslinking agent is further contained, the ratio of A:B:C:crosslinking agent=20-80:80-20:0.2-2.0:0.2-2.0 can be A:B:C:crosslinking agent=25-70:70-25:0.3-1.5:0.3-1.5, and further, A:B:C:crosslinking agent=29-65:70-35:0.5-1.5:0.5-1.5 can be. When the composition further contains at least one compound of D) unsubstituted alkyl (meth)acrylic monomer component group, the ratio A:B:C:D is 20-80:80-20:0.2-2.0:10-70, A:B:C:D can be 25-70:70-25:0.3-1.5:20-60, and further A:B:C:D can be 29-65:70-35:0.5-1.5:30-50. In the case where a crosslinking agent is further included, the ratio of A:B:C:D:crosslinking agent is 20-80:80-20:0.2-2.0::10-700.2-2.0, A:B:C::D crosslinking agent is 25-70:70-25:0.3-1.5:20-60:0.3-1.5, and further, A:B:C:D:crosslinking agent is 29-65:70-35:0.5-1.5:30-50:0.5-1.5. The same applies to the ratio of each monomer component group in the copolymer described later.
[0134] (Conductive material) In another aspect, the present disclosure provides a conductive material having improved electrical conductivity.
[0135] In one specific aspect, the present disclosure provides a conductive material comprising a copolymer of a compound including an ether moiety-containing (meth)acrylic monomer component group, a halogen-containing (meth)acrylic monomer component group, and a hydroxyl-containing (meth)acrylic monomer component group, and optionally including a crosslinker, and a conductive component. A preferred embodiment of the conductive material can utilize any embodiment or combination thereof described herein, and can be applied in combination with one or more of any embodiments described in the (Conductivity Improvement Application) section of this specification.
[0136] (Manufacturing method) In one aspect, the present disclosure provides a method for producing the conductive material and conductivity enhancer of the present disclosure.
[0137] In a specific aspect, the present disclosure provides a method for producing a conductive material comprising a homopolymer or copolymer of a compound containing at least one of an ether moiety-containing (meth)acrylic monomer component group, a halogen-containing (meth)acrylic monomer component group, a hydroxyl-containing (meth)acrylic monomer component group, and an unsubstituted alkyl (meth)acrylic monomer component group, and optionally a crosslinker, and a conductive component. The method includes the steps of polymerizing the monomer and a polymerizable monomer to obtain a copolymer, mixing the copolymer and the conductive component to obtain a mixture, and heating the mixture to produce a conductive material. A preferred embodiment of the production method can utilize any embodiment or combination thereof described herein, and can be applied in combination with one or more of any embodiments described in the section (Conductivity Improvement Application) of this specification.
[0138] In the step of obtaining a copolymer by photopolymerizing the monomer and the polymerizable monomer in the production method of the present disclosure, the following conditions are typically preferred: atmospheric pressure, 5°C to 100°C.
[0139] In the step of mixing the copolymer and the conductive component to obtain a mixture in the production method of the present disclosure, the following conditions are typically preferred: stirring with a planetary mixer at atmospheric pressure and room temperature.
[0140] In the step of heating the mixture to produce the conductive material in the production method of the present disclosure, the following conditions are typically preferred: atmospheric pressure, 120° C. to 150° C.
[0141] (copolymer) The present disclosure provides copolymers using the techniques of the present disclosure.
[0142] In a specific aspect, the present disclosure is a copolymer of an ether moiety-containing (meth)acrylate, a halogen-containing (meth)acrylate, and a hydroxy-containing (meth)acrylate.
[0143] In an exemplary embodiment, the ether moiety-containing (meth)acrylate has the formula (1): [ka] is a monomer represented by The halogen-containing (meth)acrylate is represented by the formula (2): [ka] is a monomer represented by The hydroxy-containing (meth)acrylate is represented by the formula (3): [ka] is a monomer represented by In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is as defined herein.
[0144] In one embodiment, R 6 is an alkyl group substituted with one or more hydroxy groups.
[0145] In one embodiment, the copolymer is a copolymer comprising an alkoxy-substituted alkyl (meth)acrylate and a haloalkyl (meth)acrylate.
[0146] The hydroxy-containing (meth)acrylates may be used with a crosslinking agent during copolymerization.
[0147] The copolymer is used, for example, as a matrix for a conductive material.
[0148] In one embodiment, the copolymer is a copolymer of the ether moiety-containing (meth)acrylate represented by formula (1), the halogen-containing (meth)acrylate represented by formula (2), and a hydroxy-containing (meth)acrylate represented by formula (3).
[0149] In one embodiment, the copolymer is a copolymer of an alkoxy-substituted alkyl (meth)acrylate, a haloalkyl (meth)acrylate, and a hydroxy-substituted alkyl (meth)acrylate.
[0150] The present disclosure also relates to a method for preparing a copolymer of an ether moiety-containing (meth)acrylic monomer, an alkyl (meth)acrylate substituted with a halogen-containing group, and a hydroxy-containing (meth)acrylic monomer, The ether moiety-containing (meth)acrylic monomer has the formula (1): [ka] is represented by In the formula, R 1 is a hydrogen atom or a methyl group, and R 2 is an alkyl, cycloalkyl, or aryl substituted with an alkyloxy, cycloalkyloxy, or aryloxy group; The halogen-containing group-substituted alkyl(meth)acrylate is represented by the formula (2): [ka] is represented by In the formula, R 3 is a hydrogen atom or a methyl group, R 4 is an alkyl, cycloalkyl, or aryl substituted with one or more of the same or different halogen atoms, with the proviso that R 4 is not an alkyl, cycloalkyl, or aryl containing an ether group, The hydroxy-containing (meth)acrylic monomer has the formula (3): [ka] is represented by In the formula, R 5 is a hydrogen atom or a methyl group, and R 6 is an alkyl, cycloalkyl, or aryl substituted with a hydroxy group, except that R 6 The hydroxy-containing (meth)acrylic monomer is not an alkyl, cycloalkyl, or aryl substituted with ether and halogen, and may be crosslinked with a crosslinking agent if desired. The copolymer is used, for example, as a matrix for a conductive material.
[0151] In one embodiment, the present disclosure relates to a method of making a copolymer, wherein the copolymer comprises an unsubstituted alkyl (meth)acrylate, The unsubstituted alkyl (meth)acrylate has the formula (4): [ka] In the formula, R 7 and R 8 is as defined herein.
[0152] In one embodiment, R 8is an unsubstituted alkyl group having 11 or more carbon atoms. In one embodiment, R 8 is an unsubstituted alkyl group having 11 to 30 carbon atoms. In one embodiment, R 8 is an unsubstituted alkyl group having 11 to 24 carbon atoms.
[0153] In one embodiment, R 8 is an unsubstituted alkyl group having 13 or more carbon atoms. In one embodiment, R 8 is an unsubstituted alkyl group having 13 to 30 carbon atoms. In one embodiment, R 8 is an unsubstituted alkyl group having 13 to 24 carbon atoms.
[0154] In one embodiment, R 8 is an unsubstituted alkyl group having 18 or more carbon atoms. In one embodiment, R 8 is an unsubstituted alkyl group having 18 to 30 carbon atoms. In one embodiment, R 8 is an unsubstituted alkyl group having 18 to 24 carbon atoms.
[0155] The present disclosure provides matrix applications. In one aspect, the present disclosure includes copolymers of compounds comprising at least one of ether moiety-containing (meth)acrylic monomer components of formula (1), halogen-containing (meth)acrylic monomer components of formula (2), hydroxy-containing (meth)acrylic monomer components of formula (3), and unsubstituted alkyl (meth)acrylic monomer components of formula (4), and optionally including a crosslinker. A composition for use as a matrix in a conductive material is provided that includes a conductive component.
[0156] (mixture) The present disclosure also provides mixtures.
[0157] In one aspect, the present disclosure provides a mixture of matter (i.e., a composition comprising a copolymer and a metal-based component). Specifically, the present disclosure provides a mixture of said copolymer and a metal.
[0158] In an exemplary embodiment, the mixture is a copolymer of at least one compound of the ether moiety-containing (meth)acrylic monomer component group of formula (1) and at least one compound of the halogen-containing (meth)acrylic monomer component group of formula (2), and a metal.
[0159] In one embodiment, the mixture is a copolymer of at least one compound of the ether moiety-containing (meth)acrylic monomer component group of formula (1), at least one compound of the halogen-containing (meth)acrylic monomer component group of formula (2), at least one compound of the hydroxy-containing (meth)acrylic monomer component group of formula (3), and a metal.
[0160] In one embodiment, the mixture is a copolymer of at least one compound of the ether moiety-containing (meth)acrylic monomer component group of formula (1), at least one compound of the halogen-containing (meth)acrylic monomer component group of formula (2), at least one compound of the hydroxy-containing (meth)acrylic monomer component group of formula (3), and at least one compound of the unsubstituted alkyl (meth)acrylic monomer component group of formula (4), and a metal.
[0161] In one embodiment, the metal comprises silver, copper, gold, aluminum, zinc, tin, nickel, and / or iron. In a preferred embodiment, the metal is silver, because, without wishing to be bound by theory, silver is a good conductor of electricity and is durable.
[0162] (Note) In this specification, "or" is used when "at least one or more" of the items listed in the sentence can be employed. The same applies to "alternative." In this specification, when it is specified that "within a range of two values," the range includes the two values themselves.
[0163] All references cited herein, including scientific literature, patents, patent applications, and the like, are hereby incorporated by reference in their entirety to the same extent as if each was specifically set forth.
[0164] The present disclosure has been described above by showing preferred embodiments for ease of understanding. The present disclosure will be described below based on examples, but the above description and the following examples are provided for illustrative purposes only and are not provided for the purpose of limiting the present disclosure. Therefore, the scope of the present disclosure is not limited to the embodiments or examples specifically described in this specification, but is limited only by the scope of the claims. EXAMPLES
[0165] Examples are described below. The handling of the organisms used in the following examples complied with standards stipulated by regulatory agencies, if necessary. The specific reagents used were the products described in the examples, but equivalent products from other manufacturers (Sigma-Aldrich, etc.) can also be used.
[0166] Example A: Preparation of polymer matrix In this example, a polymer matrix was prepared.
[0167] Example 1 2-Methoxyethyl acrylate (62 g, manufactured by Osaka Organic Chemical Industry Co., Ltd., trade name 2-MTA) as monomer A, 2,2,2-trifluoroethyl acrylate (36 g, manufactured by Osaka Organic Chemical Industry Co., Ltd., trade name Viscoat V#3F) as monomer B, 4-hydroxybutyl acrylate (1 g, manufactured by Osaka Organic Chemical Industry Co., Ltd., trade name Viscoat 4-HBA) as monomer C, 2,4,6-trimethylbenzoyldiphenylphosphine oxide (1 g, manufactured by BASF, trade name Irgacure (registered trademark) TPO) as a polymerization initiator, and α-methylstyrene dimer (1 g, manufactured by NOF Corporation, trade name Nofumer MSD) as a chain transfer agent were mixed to obtain a monomer component containing a polymerization initiator. The obtained monomer component was poured into a transparent glass mold (length: 100 mm, width: 100 mm, depth: 2 mm), and then the monomer component was exposed to an irradiation dose of 0.36 mW / cm. 2 The monomer components were irradiated with ultraviolet light so that the temperature reached 100° C., and the monomer components were bulk polymerized for 2 hours to obtain a polymer.
[0168] Preparation of conductive material precursor The resulting polymer (2.50 g) was dissolved in 3-methoxy-3-methyl-1-butanol (7.50 g) to obtain a resin solution. The above resin solution (4.00 g) was mixed with silver filler (4.00 g, manufactured by Fukuda Metal Foil & Powder Co., Ltd., product name AgC-A), a crosslinking agent (0.010 g, manufactured by Asahi Kasei Corporation, product name MF-K60B), 2-(2-butoxyethoxy)ethanol (0.10 g) as a dispersant, and a rheology modifier (0.010 g, manufactured by Big-Chemie Japan, product name RHEOBYK-410) using a Mazerustar manufactured by Kurabo Industries, to obtain a conductive material precursor.
[0169] (paint film formation) The obtained conductive material precursor was applied to a release polyethylene terephthalate film (manufactured by Mitsui Chemicals Tocello Inc., product name Separator SP-PET PET-01-Bu) as a release film to form a coating film.
[0170] (Conductive film) The resulting coating was heated in an oven at 120° C. for 30 minutes to obtain a conductive film having a thickness of approximately 40 μm.
[0171] (Examples 2 to 4) An acrylic resin solution was obtained in the same manner as in Example 1, except that the ratios of monomer A, monomer B, monomer C and the crosslinking agent were changed as shown in the table below.
[0172] Example 5 An acrylic resin solution was obtained in the same manner as in Example 1, except that ethyl acrylate (EA, 31 g) was newly added as monomer D, and 2-methoxyethyl acrylate (31 g, manufactured by Osaka Organic Chemical Industry Co., Ltd., product name 2-MTA) as monomer A, 2,2,2-trifluoroethyl acrylate (36 g, manufactured by Osaka Organic Chemical Industry Co., Ltd., product name Viscoat V#3F) as monomer B, 4-hydroxybutyl acrylate (1 g, manufactured by Osaka Organic Chemical Industry Co., Ltd., product name Viscoat 4-HBA) as monomer C, isocyanate (1 g) as a crosslinking agent, and 2,4,6-trimethylbenzoyldiphenylphosphine oxide (1 g, manufactured by BASF, product name Irgacure (registered trademark) TPO) as a polymerization initiator were mixed in the above amounts.
[0173] (Comparative Examples 1 and 2) The corresponding polymer was obtained by using only 2-MTA (monomer A) and V#3F (monomer B) as monomers. The weight parts of the compositions of the monomers A and B used are as shown in Table 1.
[0174] Comparative Example 3 Similarly, the corresponding polymer was obtained using V#3F (monomer B), 4-HBA (monomer C) and isocyanate (crosslinking agent). The weight parts of the monomer B, monomer C and crosslinking agent used are as shown in Table 1.
[0175] Comparative Example 4 Similarly, the corresponding polymer was obtained using V#3F (monomer B), 4-HBA (monomer C), isocyanate (crosslinker) and EA (monomer D). The weight parts of the monomer B, monomer C and crosslinker used are as shown in Table 1.
[0176] Example B: Preparation of Conductive Film In this example, a conductive film was prepared.
[0177] (Conductive material precursor) Each acrylic resin solution (6.00 g) obtained in Example A was mixed with silver filler (7.20 g, manufactured by Fukuda Metal Foil & Powder Co., Ltd., product name AgC-A) and 2-(2-butoxyethoxy)ethanol (0.10 g) as a dispersant using a Mazerustar manufactured by Kurabo Industries Co., Ltd. to obtain a conductive material precursor.
[0178] (paint film formation) The obtained conductive material precursor was applied to a release polyethylene terephthalate film (manufactured by Mitsui Chemicals Tocello Inc., product name Separator SP-PET PET-01-Bu) as a release film to form a coating film.
[0179] (Conductive film) The resulting coating was heated in an oven at 120° C. for 30 minutes to obtain a conductive film having a thickness of approximately 40 μm.
[0180] (result) Conductive films were prepared according to the procedures described in Examples A and B. The results are shown in Table 1. [Table 1]
[0181] (Example C: Measurement of volume resistivity) The conductive film obtained in Example B was cut into a piece having a length of 0.5 cm and a width of 2.00 cm, and was measured by a four-terminal method using Loresta GP (manufactured by Mitsubishi Chemical Analytech Co., Ltd.).
[0182] (result) The results are shown in Table 1.
[0183] (Example D: Confirmation of change in resistance value) In this embodiment, the change in resistance value was confirmed.
[0184] (Resistance measurement) The conductive film obtained above was cut into a piece having a length of 0.5 cm and a width of 2.00 cm, and the resistance value (ΩA) before stretching was measured using a digital multimeter (manufactured by Sanwa Denki Keiki Co., Ltd., product name PC773) with the interelectrode distance fixed at 1.00 cm.
[0185] (Resistance change) Next, while the conductive film was fixed on the multimeter electrodes, the distance between the electrodes was set to 2.00 cm, and the resistance value (ΩB) in this state was measured. The change in resistance value was calculated as follows. Resistance change = ΩB / ΩA
[0186] (result) The results are shown in Table 1. The smaller the change in resistance value (closer to 1), the smaller the effect of the shape change, which means higher durability. Therefore, the change in resistance value can also be evaluated as durability.
[0187] Example E: Measurement of Flexibility The conductive film obtained in the above example was cut into a test piece (dumbbell-shaped No. 7). The flexibility of this test piece was measured at a tension speed of 50 mm / min using a tensile tester (manufactured by A&D Co., Ltd.: product name TENSILON RTG-1310). Young's modulus was calculated from the obtained value.
[0188] (result) The results are shown in Table 1.
[0189] (Note) Although the present disclosure has been illustrated using the preferred embodiments thereof, it is understood that the present disclosure should be interpreted in scope only by the claims. It is understood that the patents, patent applications, and other documents cited in this specification are incorporated by reference into this specification in the same manner as if the contents themselves were specifically set forth herein. [Industrial Applicability]
[0190] The electrical conductivity enhancer of the present disclosure can be used to provide an efficient electrical conductivity material, which can be utilized in industries requiring electrical conductivity materials.
Claims
1. A) at least one compound from the group of ether moiety-containing (meth)acrylic monomer components; B) at least one compound from a group of halogen-containing (meth)acrylic monomer components; C) at least one compound from the group of hydroxy-containing (meth)acrylic monomer components; Including, A conductivity enhancer for improving the conductivity of a conductor, comprising: The compound of the ether moiety-containing (meth)acrylic monomer component group is represented by the formula (1) 【Chemistry 18】 is a first (meth)acrylate represented by R 1 is a hydrogen atom or a methyl group; R 2 is an alkyl, cycloalkyl, or aryl substituted with an alkyloxy, cycloalkyloxy, or aryloxy group; The compound of the halogen-containing (meth)acrylic monomer component group is represented by the formula (2) 【Chemistry 19】 is a second (meth)acrylate represented by R 3 is a hydrogen atom or a methyl group; R 4 is an alkyl, cycloalkyl, or aryl substituted with from 1 to a substitutable number of the same or different halogen atoms; At least one compound of the hydroxy-containing (meth)acrylic monomer component group is represented by the formula (3) 【Chemistry 20】 and a third (meth)acrylate represented by R 5 is a hydrogen atom or a methyl group; The conductivity enhancer, wherein R 6 is an alkyl, cycloalkyl, or aryl substituted with a hydroxy group.
2. The conductivity enhancer of claim 1 , further comprising a cross-linking agent.
3. The electrical conductivity improver according to claim 2 , wherein the crosslinking agent has a functional group that crosslinks the compounds of the component group C.
4. D) At least one compound from the group of unsubstituted alkyl (meth)acrylic monomer components The electrical conductivity improver according to any one of claims 1 to 3, further comprising:
5. At least one compound of the unsubstituted alkyl (meth)acrylic monomer component group is represented by the formula (4) 【Chemistry 21】 and a fourth (meth)acrylate represented by R 7 is a hydrogen atom or a methyl group, R 8 is unsubstituted alkyl, cycloalkyl, or aryl; The electrical conductivity enhancer according to claim 4 .
6. The first (meth)acrylate is selected from the group consisting of tetrahydrofurfuryl (meth)acrylate, phenoxyethyl (meth)acrylate, ethoxyethoxyethyl (meth)acrylate, 2-methoxyethyl (meth)acrylate, methoxytriethylene glycol (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, (2-methyl-2-ethyl-1,3-dioxolan-4-yl)methyl (meth)acrylate, (3-ethyloxetan-3-yl)methyl (meth)acrylate, and (5-ethyl-1,3-dioxane-5-yl)methyl (meth)acrylate. The conductivity improver according to any one of claims 1 to 4.
7. The electrical conductivity improver according to any one of claims 1 to 6, wherein the second (meth)acrylate comprises at least one selected from the group consisting of 2,2,2-trifluoroethyl (meth)acrylate, 2,2,3,3-tetrafluoropropyl (meth)acrylate, 1H,1H,5H-octafluoropentyl (meth)acrylate, and 1H,1H,2H,2H-tridecafluorooctyl (meth)acrylate.
8. The electrical conductivity improver according to any one of claims 1 to 7, wherein the third (meth)acrylate includes at least one selected from the group consisting of 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, and 4-hydroxybutyl (meth)acrylate.
9. The electrical conductivity enhancer according to claim 5 , wherein the fourth (meth)acrylate comprises at least one selected from the group consisting of ethyl acrylate, isostearyl acrylate, stearyl acrylate, and lauryl acrylate.
10. A conductive material comprising a polymer matrix obtained by polymerizing the conductivity enhancer according to any one of claims 1 to 9, a conductive component, and a substrate.
11. 11. The conductive material of claim 10, wherein the conductive component comprises a metal component, a metal oxide, a metal-based component of a metal carbide, a conductive carbon-based component, a conductive organic compound, a conductive polymer, or a combination thereof.
12. The electrical conductivity enhancer according to any one of claims 1 to 9, which improves the flexibility of a conductive component or a conductive material.
13. The electrical conductivity improver according to any one of claims 1 to 9, which improves the durability of an electrically conductive component or an electrically conductive material.
14. A) at least one compound selected from the group consisting of ether moiety-containing (meth)acrylic monomer components; B) at least one compound from a group of halogen-containing (meth)acrylic monomer components; C) at least one compound from the group of hydroxy-containing (meth)acrylic monomer components; a polymer matrix obtained by polymerizing A solvent; A mixture of a conductive component, The compound of the ether moiety-containing (meth)acrylic monomer component group is represented by the formula (1) 【Chemistry 18】 is a first (meth)acrylate represented by R 1 is a hydrogen atom or a methyl group; R 2 is an alkyl, cycloalkyl, or aryl substituted with an alkyloxy, cycloalkyloxy, or aryloxy group; The compound of the halogen-containing (meth)acrylic monomer component group is represented by the formula (2) 【Chemistry 19】 is a second (meth)acrylate represented by R 3 is a hydrogen atom or a methyl group; R 4 is an alkyl, cycloalkyl, or aryl substituted with from 1 to a substitutable number of the same or different halogen atoms; At least one compound of the hydroxy-containing (meth)acrylic monomer component group is represented by the formula (3) 【Chemistry 20】 and a third (meth)acrylate represented by R 5 is a hydrogen atom or a methyl group; Mixtures where R 6 is alkyl, cycloalkyl, or aryl substituted with a hydroxy group.
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