JP2022121217A - Novel conductivity improver - Google Patents

Abstract

To provide a novel conductivity improver.SOLUTION: A composition for improving electrical conductivity of a conductive component or conductive material comprising ether moiety-containing (meth)acrylic monomer components, halogen-containing (meth)acrylic monomer components, and hydroxy-containing (meth)acrylic monomer components, and copolymer of a compound containing a cross-linking agent on an as-needed basis, a production method thereof, and a use thereof as matrix are provided. The composition may further comprise at least one compound of unsubstituted alkyl (meth)acrylic monomer components.SELECTED DRAWING: None

Description

TECHNICAL FIELD This disclosure relates to novel conductivity enhancers and related art. More specifically, the present disclosure includes ether moiety-containing (meth)acrylic monomer components, halogen-containing (meth)acrylic monomer components, and hydroxy-containing (meth)acrylic monomer components, and optionally a cross-linking agent. The present invention relates to a composition for improving the conductivity of a conductive material, etc., comprising a copolymer of a compound containing the present invention.

Various improvements have been made to conductive materials and conductors. However, currently available conductive materials are limited to those containing a specific combination of conductive components.

JP 2019-102719 A WO2015/099049 WO2019/039511 WO2017/163615 JP 2017-183207 A

The present disclosure provides a conductive material that includes a desired combination of conductive components that enhances the electrical conductivity of the conductive material.

The present disclosure provides, for example, A) at least one compound of the ether moiety-containing (meth)acrylic monomer component group, B) at least one compound of the halogen-containing (meth)acrylic monomer component group, and C) hydroxy-containing (meth) Compositions or combinations, various methods of making and using the same for improving the electrical conductivity of electrical conductors comprising at least one compound of the acrylic monomer component group.

It is contemplated in the present disclosure that one or more features described herein may be provided in further combinations in addition to the explicit combinations. Various embodiments and advantages of the present disclosure will be appreciated by those skilled in the art upon reading and understanding the following detailed description, if necessary.

INDUSTRIAL APPLICABILITY According to the present disclosure, a conductivity improver is provided, and a technique capable of improving conductivity can be provided by using these agents. The present disclosure can also improve conductivity while improving flexibility. The present disclosure also produces conductive materials with improved conductivity and improved durability.

Hereinafter, the present disclosure will be described while showing the best mode. It should be understood that throughout this specification, expressions in the singular also include the concept of the plural unless specifically stated otherwise. Thus, articles in the singular (eg, “a,” “an,” “the,” etc. in the English language) should be understood to include their plural forms as well, unless otherwise stated. Also, it should be understood that the terms used in this specification have the meanings commonly used in the relevant field unless otherwise specified. Thus, unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs. In case of conflict, the present specification (including definitions) will control.

Definitions of terms and/or basic technical content particularly used in the present specification will be described below as appropriate.

(Definition of terms)
As used herein, conductivity (or resistivity) is measured as follows. Specifically, unless otherwise specified, the object to be measured (for example, a film, etc.) is cut into 0.5 cm length × 2.00 cm width × 0.2 cm thickness, and a four-terminal measurement method (for example, Loresta GP [Mitsubishi Chemical Analyticc] can be used, but is not limited to this.) is employed.

As used herein, "conductive material" refers to any material that is electrically conductive. In this specification, the conductive material has a resistance of 1.0×10 ⁻¹ Ω·cm or less, usually 1.0×10 ⁻² Ω·cm or less, preferably 1.0×10 ⁻³ Ω·cm or less. Intended for, but not limited to, those with rates. The conductive material includes a conductive component that imparts electrical conductivity. Typically, the conductive material usually comprises a base material and a conductive component.

As used herein, "improved conductivity" refers to a significant increase in conductivity when a component of the present disclosure is added to a conductive component or conductive material compared to when it is not added. For example, 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 An improvement of 80%, about 85%, about 90%, about 95%, about 99% can also be expressed by a decrease in volume resistivity. For example, volume resistivity of 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%, about 99% reduction.

As used herein, the term "substrate" is also referred to as a matrix, refers to a basic portion of the structure of a conductive material, and corresponds to a base for arranging conductive components. Various polymers can be used as the substrate. When the substrate is a polymer, it may be referred to as a polymer matrix.

As used herein, "conductive component" means any component that imparts electrical conductivity. Examples of conductive components include, but are not limited to, metal components such as arbitrary metal components, metal oxides, and metal carbides, conductive carbon-based components, conductive organic compounds, and conductive polymers. .

As used herein, the term “metal-based component” refers to a component containing metal atoms in some form as a constituent thereof, and in addition to metal components such as metals, components derived from metals (e.g., metal oxides, metal carbides, metal sulfide, etc.).

As used herein, the term "metal component" includes metals or alloys.

As used herein, the term “conductive carbon-based component” means a conductive material containing carbon. Specific examples thereof include natural graphite such as flake graphite, graphite such as artificial graphite, acetylene black, ketjen black, channel black, furnace black, lamp black, carbon black such as thermal black, graphene, carbon nanotubes, Carbon-based materials such as fullerene; carbon fiber; carbon fluoride, etc., but not limited thereto. Metal carbides are not included in the conductive carbonaceous component. "Conductive carbon-based component" may also be referred to as "carbon-based component."

As used herein, the term "(meth)acrylic monomer" refers to a monomer containing an acrylic group and/or a methacrylic group, examples of which include acrylic acid, methacrylic acid, acrylic acid esters, methacrylic acid esters, acrylic acid amides, and methacrylic acid amide.

As used herein, "(meth)acrylic" means "acrylic" or "methacrylic", and "(meth)acrylate" means "acrylate" or "methacrylate".

As used herein, 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, one type of compound of the ether moiety-containing (meth)acrylic monomer component group may be used, or a plurality of types may be used. Examples of 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, methoxy Triethylene glycol (meth) acrylate, methoxy polyethylene glycol (meth) acrylate, methoxy polyethylene 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-dioxan-5-yl)methyl (meth)acrylate, and the like, although this disclosure is intended only as such examples. It is not limited. Compounds of the ether moiety-containing (meth)acrylic monomer component group of the present disclosure are sometimes referred to herein as "ether moiety-containing (meth)acrylates."

As used herein, the term "halogen-containing (meth)acrylic monomer component group" refers to a group of (meth)acrylic monomers containing at least one halogen. In the present disclosure, one type of compound of the halogen-containing (meth)acrylic monomer component group may be used, or a plurality of types may be used. 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 and the like, but the present disclosure is not limited to such examples only. Compounds of the halogen-containing (meth)acrylic monomer component group of the present disclosure are sometimes referred to herein as "halogen-containing (meth)acrylates."

As used herein, "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 crosslinkable moieties. In the present disclosure, one type of compound of the hydroxy-containing (meth)acrylic monomer component group may be used, or a plurality of types 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. The disclosure is not limited to only such exemplifications. Compounds of the hydroxy-containing (meth)acrylic monomer component group of the present disclosure are sometimes referred to herein as "hydroxy-containing (meth)acrylates."

As used herein, the term "unsubstituted alkyl (meth)acrylic monomer component group" refers to a group of monomers containing (meth)acrylic structures that do not have substantial functional groups (for example, contain only alkyl groups). In the present disclosure, one type of compound of the unsubstituted (meth)acrylic monomer component group may be used, or a plurality of types 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 intended to be limited to such examples only. is not.

The composition or combination according to the present invention may have the following forms.
(1) The compound of the ether moiety-containing (meth)acrylic monomer component group contains neither halogen nor hydroxy group, and the compound of the halogen-containing (meth)acrylic monomer component group contains neither ether moiety nor hydroxy group. , wherein 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 (first monomer) contained in the composition or combination according to the present invention is an ether moiety-containing (meth)acrylic monomer, a halogen-containing (meth)acrylic monomer, and a hydroxy-containing A form in which two of the (meth)acrylic monomers are applicable and the other one (second monomer) is a monomer species to which the first monomer is not applicable.
(3) One of the three or more monomers (first monomer) contained in the composition or combination according to the present invention is an ether moiety-containing (meth)acrylic monomer, a halogen-containing (meth)acrylic monomer, and a hydroxy-containing It corresponds to two of the (meth) acrylic monomers, the other one (second monomer) is a monomer species that does not correspond to the first monomer, and the other one (third monomer) is the first is identical to one of the corresponding monomer species. In this case, the first monomer is treated as a monomer species to which the third monomer does not apply.

As used herein, a "crosslinking agent" is a reactive agent capable of reacting with functional groups on a polymer to link the polymers together intramolecularly or intermolecularly. Examples of cross-linking agents include formaldehyde, 2,4-tolylene diisocyanate, hexamethylene diisocyanate, polyisocyanates (such as hexamethylene diisocyanate), Duranate ^TM (manufactured by Asahi Kasei Corporation), and the like. It is not limited only to such examples.

As used herein, the term "crosslinking functional group" refers to a functional group capable of forming a crosslinked structure, and the crosslinkable functional group reacts with a cross-linking agent to form a crosslinked structure between molecules or within a molecule. can do.

As used herein, the term "substitutable number" refers to the maximum number of substitutable hydrogens, provided that the resulting group is chemically stable when substituting hydrogen on a group with a substituent. means.

As used herein, alkyl groups can be straight or branched. C 1-4 alkyl (C _1-4 alkyl) groups include, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl groups and the like, but the present disclosure is not limited to such examples. C 1-6 alkyl (C _1-6 alkyl) groups include, for example, C _1-4 alkyl groups, n-pentyl groups, isoamyl groups, n-hexyl groups, isohexyl groups and the like, but the present disclosure is not limited only to such examples. Examples of C 1-10 alkyl (C _1-10 alkyl) groups include C _1-6 alkyl groups, n-octyl groups, n-nonyl groups, isononyl groups, branched nonyl groups, n-decanyl groups, isodecyl group and the like, but the present disclosure is not limited to such examples. Examples of C 1-18 alkyl (C 1-18 alkyl) groups include _{C 1-10 alkyl} groups, undecyl groups, lauryl groups, tridecyl groups, myristyl groups, pentadecyl groups, palmityl groups, heptadecyl groups, and stearyl groups. , an isostearyl group, etc., but the present disclosure is not limited only to such examples.

As used herein, alkenyl groups can be straight or branched. Examples of the alkenyl group having 2 to 6 carbon atoms include ethenyl group, 1-propenyl group, 2-propenyl group, butenyl group, pentenyl group, hexenyl group and the like, but the present disclosure is limited only to such examples. not something. Examples of alkenyl groups having 2 to 10 carbon atoms include alkenyl groups having 2 to 6 carbon atoms, heptenyl groups, octenyl groups, nonenyl groups, decenyl groups and the like, but the present disclosure is limited only to such examples. not a thing

In the present specification, the alkoxy group having 1 to 6 carbon atoms includes, for example, methoxy group, ethoxy group, n-propyloxy group, isopropyloxy group, n-butyloxy group, isobutyloxy group, tert-butyloxy group, sec- A butyloxy group, an n-pentyloxy group, an isoamyloxy group, an n-hexyloxy group, an isohexyloxy group and the like can be mentioned, but the present disclosure is not limited only to such examples.

As used herein, an "alkoxy-substituted alkyl group" refers to an alkyl group in which one or more hydrogen atoms on the alkyl group are substituted with an alkoxy group.

As used herein, 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. "Perhaloalkyl" refers to an alkyl group in which all hydrogen atoms on the above alkyl group are substituted with halogen atoms. The haloalkyl group having 1 to 6 carbon atoms (C _1-6 haloalkyl group) includes, for example, a C _1-6 fluorinated alkyl group and the like, for example, a trifluoromethyl group, a trifluoroethyl group (2,2, 2-trifluoroethyl group, etc.), perfluoroethyl group, trifluoro n-propyl group, tetrafluoropropyl group (2,2,3,3-tetrafluoropropyl group, etc.), perfluoro n-propyl group, trifluoroisopropyl group , perfluoroisopropyl group, trifluoro n-butyl group, perfluoro n-butyl group, trifluoroisobutyl group, perfluoroisobutyl group, trifluoro tert-butyl group, perfluoro tert-butyl group, trifluoro n-pentyl group, octafluoropentyl groups (2,2,3,3,4,4,5,5-octafluoropentyl group, etc.), perfluoro n-pentyl group, trifluoro n-hexyl group, perfluoro n-hexyl group, etc. The disclosure is not limited to only such exemplifications. The haloalkyl group having 1 to 8 carbon atoms (C _1-8 haloalkyl group) includes a C _1-6 haloalkyl group or a C _1-8 fluorinated alkyl group such as an undecafluoro n-heptyl group, perfluoro n- heptyl group, tridecafluorooctyl group (3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl group, etc.), perfluoro n-octyl group, etc. However, the present disclosure is not limited only to such examples.

As used herein, the term "cycloalkyl group" means a monocyclic or polycyclic saturated hydrocarbon group, including those having a crosslinked structure. For example, a “C _3-12 cycloalkyl group” means a cyclic alkyl group having 3 to 12 carbon atoms. Specific examples of the _C6-12 cycloalkyl group include cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, isobornyl group, 2-methyl-2-adamantyl group, 2-ethyl-2-adamantyl group and the like. However, the present disclosure is not limited only to such examples. Specific examples of C _5-12 cycloalkyl groups include cyclopentyl groups, C _6-12 cycloalkyl groups, and the like, but the present disclosure is not limited to such exemplifications. Specific examples of C _3-12 cycloalkyl groups include cyclopropyl, cyclobutyl and C _5-12 cycloalkyl groups. A "C _6-12 cycloalkyl group" is preferred, but the present disclosure is not limited to such examples.

As used herein, the term "cycloalkenyl group" means a monocyclic or polycyclic unsaturated hydrocarbon group containing a double bond, including those having a crosslinked structure. One or more of the carbon-carbon bonds of the above "cycloalkyl group" may be a double bond. For example, a “C _3-12 cycloalkenyl group” means a cyclic alkenyl group having 3 to 12 carbon atoms. Specific examples of "C _6-12 cycloalkenyl group" include 1-cyclohexenyl group, 2-cyclohexenyl group, 3-cyclohexenyl group, cycloheptenyl group, cyclooctenyl group, cyclononenyl group and the like. be done. Examples of "C _3-12 cycloalkyl group" include cyclopropenyl group, cyclobutenyl group, cyclopentenyl group, C _6-12 cycloalkenyl group and the like. A “C _6-12 cycloalkenyl group” is preferred, but the present disclosure is not limited to such examples.

As used herein, “non-arylheterocycloalkyl” and “non-arylheterocycle” refer to a cyclic ring having 1 to 3 the same or different atoms selected from nitrogen, oxygen and sulfur atoms in the ring. means a group, which may contain one or more unsaturated bonds, but does not contain an aromatic group. For example, "3- to 8-membered nonarylheterocycloalkyl" means a nonarylheterocycloalkyl having 3 to 8 ring atoms. Specific examples of "non-arylheterocycloalkyl" include an oxiranyl group, an oxetanyl group, a pyranyl group, a pyrrolidinyl group, an imidazolidinyl group, a piperidinyl group, a morpholinyl group, a thiomorpholinyl group, a hexamethyleneiminyl group, a thiazolidinyl group, a tetrahydrofuranyl group, Tetrahydropyridinyl group, tetrahydropyranyl group, 1,3-dioxolanyl group, 1,3-dioxanyl group, 1,4-dioxanyl group, etc., but the present disclosure is not limited only to such examples. do not have. The group includes those having a crosslinked structure.

As used herein, the term "aryl group" refers to a group formed by removing one hydrogen atom bonded to an aromatic hydrocarbon ring. For example, a phenyl group (C ₆ H ₅ —) from benzene, a tolyl group (CH ₃ C ₆ H ₄ —) from toluene, a xylyl group ((CH ₃ ) ₂ C ₆ H ₃ — from xylene, is derived from a naphthyl group (C ₁₀ H ₈ —). A “C _6-14 aryl group” means an aromatic hydrocarbon group having 6 to 14 carbon atoms. Specific examples of the "C6-14 aryl group" include, for example, phenyl group, ₁ -naphthyl group, 2-naphthyl group, azulenyl group, acenaphthenyl group, acenaphthyl group, anthryl group, fluorenyl group, phenalenyl group, phenanthryl group and the like. is mentioned. Specific examples of "C _6-18 aryl group" include, for example, C _6-14 aryl group, benzo[a]anthryl group, benzo[a]fluorenyl group, benzo[c]phenanthryl group, chrysenyl group, fluoranthenyl group, pyrenyl group, tetracenyl group, triphenylenyl group, and the like. An arylthio group refers to an aryl-S- group. Examples thereof include a phenyl-S- group (phenylthio group) and the like, but the present disclosure is not limited to such examples.

As used herein, the term “heteroaryl group” means a monocyclic or polycyclic heteroatom-containing aromatic group, wherein the group is the same or different heteroatom selected from a nitrogen atom, a sulfur atom and an oxygen atom. Contains one or more atoms (eg, 1 to 4). For example, a “5- to 18-membered heteroaryl group” means a heteroaryl group having 5 to 18 ring atoms. A “haloheteroaryl group” refers to one in which one or more hydrogen atoms on a ring-constituting atom are replaced with halogen. Specific examples of the "heteroaryl group" include, for example, pyrrolyl group, thienyl group, benzothienyl group, benzofuranyl group, benzoxazolyl group, benzothiazolyl group, furyl group, oxazolyl group, thiazolyl group, isoxazolyl group, isothiazolyl group, benzisoxazolyl group, benzisothiazolyl group, imidazolyl group, pyrazolyl group, pyridyl group, pyrazyl group, pyrimidyl group, pyridazyl group, quinolyl group, isoquinolyl group, triazolyl group, triazinyl group, tetrazolyl group, indolyl group, imidazo [1,2-a]pyridyl group, pyrazolo[1,5-a]pyridyl group, [1,2,4]triazolo[1,5-a]pyridyl group, benzimidazolyl group, quinoxalyl group, cinnolyl group, quinazolyl group , indazolyl group, naphthyridyl group, quinolinolyl group, isoquinolinolyl group, etc., but the present disclosure is not limited only to such examples.

As used herein, the term "ether moiety-containing group" means a group having an oxygen atom between the carbon atoms of an optionally substituted hydrocarbon group, and the group has one or more oxygen atoms (e.g. 1 to 4). Specific examples of the "ether moiety-containing group" include, for example, methoxymethyl group, methoxyethyl group, methoxypropyl group, methoxybutyl group, ethoxymethyl group, ethoxyethyl group, ethoxypropyl group, ethoxybutyl group and the like. , the present disclosure is not limited to only such exemplifications.

As used herein, a "halogen-containing group" means a group having a halogen atom in its partial structure, and the group contains one or more (eg, 1 to 4) halogen atoms. Specific examples of the "halogen-containing group" include, for example, a trifluoromethyl group, a trifluoroethyl group, a trifluoropropyl group, a trifluorobutyl group, a trichloromethyl group, a trichloroethyl group, a trichloropropyl group, a trichlorobutyl group, and the like. , but the present disclosure is not limited to only such exemplifications.

As used herein, "hydroxy-containing group" means a group having a hydroxy group in its partial structure, and the group contains one or more (eg, 1 to 4) hydroxy groups. Specific examples of the "hydroxy-containing group" include, for example, a hydroxymethyl group, a hydroxyethyl group, a hydroxypropyl group, a hydroxybutyl group, etc., but the present disclosure is not limited only to such examples.

Generally, the term "substituted" refers to the replacement of one or more hydrogen radicals in a given structure by the radical of a specified substituent. It is recognized that the phrase "optionally substituted" is used interchangeably with the phrase "unsubstituted or substituted." For example, “a C _6-18 aryl group optionally substituted with a C _1-10 alkyl group” means “an unsubstituted C _6-18 aryl group, or a C _6-18 substituted with a C _1-10 alkyl group”. ₁₈ aryl group". In the present specification, the number of substituents in a group defined using "substituted (substituted)" or "optionally substituted" is not particularly limited as long as it can be substituted, and can be one or more. be. Also, unless otherwise indicated, the description of each group also applies when that group is part or a substituent of another group. The number of carbon atoms in the definition of "substituent" may be expressed as, for example, "C _1-6 ". Specifically, the notation "C _1-6 alkyl" is synonymous with an alkyl group having 1 to 6 carbon atoms. In addition, in the present specification, substituents for which the terms "substituted (substituted)" or "optionally substituted" are not specifically defined mean "unsubstituted" substituents.

As used herein, "(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.

As used herein, the term "combination" refers to two or more compounds that are provided with the intention of being used together when used. The combination of compounds may all be provided as one composition, but not all compounds belonging to the combination may be included in one composition, and may be provided individually. may be provided in the same composition. For example, a combination of a first (meth)acrylate and a second (meth)acrylate described herein, a first (meth)acrylate, a second (meth)acrylate and a third (meth)acrylate and a combination of a second (meth)acrylate, a third (meth)acrylate, and a fourth (meth)acrylate, etc., but the present disclosure is not limited only to such examples. do not have.

(Basic explanation of conductive materials)
The conductive materials provided in this disclosure include any conductive component available in the art. The conductive material of the present disclosure is characterized by improving conductivity by including a composition for improving conductivity provided in the present disclosure (also referred to as a conductivity improver).

Conductive materials of the present disclosure may typically include a base material in addition to the conductive component. The material of the substrate is not particularly limited, and for the purpose of peeling, it is preferable to use a material with releasability or a surface-treated material.

(Basic description of conductivity improver)
In one aspect, the composition (conductivity improver) or combination for improving conductivity provided in the present disclosure includes “ether moiety-containing (meth)acrylic monomer”, “halogen-containing (meth)acrylic monomer , and hydroxy-containing (meth)acrylic monomers. The composition may further comprise a cross-linking agent. The composition may optionally further comprise an unsubstituted alkyl (meth)acrylic monomer.

により表され、含まれるエーテル含有基の種類、アルキル基の形態（炭素数、分岐もしくは直鎖の状態など）、シクロアルキル基の形態（炭素数など）、アリール基の形態（炭素数など）、メタクリルオキシ（Ｒ^１＝メチル）、アクリルオキシ（Ｒ^１＝Ｈ）の別などにかかわらず、いずれも導電率を向上させるものである。 In a representative embodiment, one example of a compound of the class of ether moiety-containing (meth)acrylic monomer components provided in the present disclosure has formula (1)

represented by, the type of ether-containing group contained, the form of the alkyl group (number of carbon atoms, branched or linear state, etc.), the form of the cycloalkyl group (number of carbon atoms, etc.), the form of the aryl group (number of carbon atoms, etc.), Regardless of whether it is methacryloxy (R ¹ =methyl), acryloxy (R ¹ =H), etc., both improve conductivity.

により表され、含まれるハロゲン含有基の種類、アルキル基の形態（炭素数、分岐もしくは直鎖の状態など）、シクロアルキル基の形態（炭素数など）、アリール基の形態（炭素数など）、メタクリルオキシ（Ｒ^１＝メチル）、アクリルオキシ（Ｒ^１＝Ｈ）の別などにかかわらず、いずれも導電率を向上させるものである。 In an exemplary embodiment, one example of a compound of the halogen-containing (meth)acrylic monomer component group provided in the present disclosure has formula (2)

represented by the type of halogen-containing group contained, the form of the alkyl group (number of carbon atoms, branched or linear state, etc.), the form of the cycloalkyl group (number of carbon atoms, etc.), the form of the aryl group (number of carbon atoms, etc.), Regardless of whether it is methacryloxy (R ¹ =methyl), acryloxy (R ¹ =H), etc., both improve conductivity.

により表され、含まれるアルキル基の形態（炭素数、分岐もしくは直鎖の状態など）、シクロアルキル基の形態（炭素数など）、アリール基の形態（炭素数など）、メタクリルオキシ（Ｒ^１＝メチル）、アクリルオキシ（Ｒ^１＝Ｈ）の別などにかかわらず、いずれも導電率を向上させるものである。 In an exemplary embodiment, one example of a compound of the hydroxy-containing (meth)acrylic monomer component group provided in the present disclosure has formula (3)

Represented by, contained alkyl group form (carbon number, branched or linear state, etc.), cycloalkyl group form (carbon number, etc.), aryl group form (carbon number, etc.), methacryloxy (R ¹ = methyl), acryloxy (R ¹ =H), etc., all improve electrical conductivity.

The basic method of using the conductivity improver is as follows.

(Conductive component targeted by the conductivity improver)
A conductive component that can be targeted by the conductivity improver of the present disclosure is a component having any conductivity. Metal-based components and conductive carbon-based components are preferred. More preferred are metal components, carbon black, graphene and carbon nanotubes. More preferred are silver and carbon nanotubes.

(General manufacturing method of conductive material)
(1) Method for Producing Polymer Matrix In representative embodiments, the polymer matrix of the present disclosure can be prepared by heating a monomer and/or by irradiating the monomer with UV light of a specific intensity to polymerize it. . A person skilled in the art can arbitrarily set the conditions for such ultraviolet irradiation. When the polymer matrix is prepared by polymerization using ultraviolet rays, a drying operation for removing the solvent, which is a complicated operation, is not required, resulting in excellent workability.

The wavelength of ultraviolet light used in the present disclosure may be any wavelength within that range, and an appropriate wavelength can be selected according to the purpose. For example, in the present disclosure, any wavelength may be used as long as it has an initial effect on the monomer. Typically, it is of a wavelength that can be illuminated by the light source used in the examples. Specifically, a light source of about 150 nm to 400 nm is used, preferably 300 nm to 400 nm.

The preferred intensity of ultraviolet light used in this disclosure will vary depending on the starting material. The ultraviolet irradiation device is not particularly limited, and examples include low-pressure mercury lamps, medium-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, metal halide lamps, black light lamps, UV electrodeless lamps, short arc lamps, and LEDs. is mentioned.

When polymerizing the monomer, it is preferable to use a polymerization initiator. Examples of polymerization initiators include thermal polymerization initiators, photopolymerization initiators, redox polymerization initiators, ATRP (atom transfer radical polymerization) initiators, ICAR ATRP initiators, ARGET ATRP initiators, RAFT (reversible addition-fragmentation chain transfer polymerization) agents, NMP (nitroxide-mediated polymerization) agents, polymer polymerization initiators, and the like. These polymerization initiators may be used alone or in combination of two or more. Among these polymerization initiators, photopolymerization initiators are preferred from the viewpoint of not leaving heat history in the polymer matrix.

Examples of photopolymerization initiators 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′-di-tert-butyldiphenyliodonium 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, phenylglyoxylic 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-cyclopentadien-1-yl) Photoradical polymerization initiators such as bis[2,6-difluoro-3-(1H-pyrrol-1-yl)phenyltitanium], 2,4,6-tris(trichloromethyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(p-methoxyphenylvinyl)-1,3,5-triazine, diphenyliodonium tetrafluoroborate, 4,4′-di-tert-butyldiphenyliodonium tetrafluoroborate, 4 Photocationic ring-opening polymerization initiators such as -diethylaminophenylbenzenediazonium hexafluorophosphate, diphenyl-4-phenylthiophenylsulfonium hexafluorophosphate, etc., but the present disclosure is not limited only to such examples. These photopolymerization initiators may be used alone, respectively, or two or more of them may be used in combination.

When a photopolymerization initiator is used as the polymerization initiator, the amount of the photopolymerization initiator is preferably about 0.01 to about 20 parts by weight per 100 parts by weight of the total monomers.

Thermal polymerization initiators include, for example, azobisisobutyronitrile (AIBN), 2,2′-azobis(methyl isobutyrate), 2,2′-azobis(2,4-dimethylvaleronitrile), 2,2 Azo polymerization initiators such as '-azobis(2-methylbutyronitrile), 1,1'-azobis(cyclohexane-1-carbonitrile), peroxides such as benzoyl peroxide, potassium persulfate and ammonium persulfate Polymerization initiators and the like may be mentioned, but the present disclosure is not limited only to such examples. These polymerization initiators may be used alone or in combination of two or more.

When a thermal polymerization initiator is used as the polymerization initiator, the amount of the thermal polymerization initiator is preferably about 0.01 to about 20 parts by weight per 100 parts by weight of all monomers.

When using polymerization initiators that generate nitrogen (N ₂ ) during the polymerization reaction, such as AIBN, the resulting composite may contain air bubbles. Since such air bubbles can serve as starting points for rupture, it is expected that properties such as extensibility of the composite material may be reduced, but the impact absorption capacity may be improved. In addition, the bubbles contained in the composite material are not limited to those derived from the polymerization initiator, and may be obtained by adding a foaming agent or by removing the solvent. It may be air bubbles obtained by a known method that can be used.

Other polymerization initiators that can be used in the present disclosure include, for example, hydrogen peroxide and iron(II) salts, persulfates and redox polymerization initiators such as sodium bisulfite, ATRP using alkyl halides under metal catalysis. (atom transfer radical polymerization) initiators, ICAR ATRP initiators and ARGET ATRP initiators using metals and nitrogen-containing ligands, RAFT (reversible addition-fragmentation chain transfer polymerization) agents, NMP (nitroxide mediated polymerization) agents , polydimethylsiloxane unit-containing polymeric azo polymerization initiators, polyethylene glycol unit-containing polymeric azo polymerization initiators, etc., but the present disclosure is not limited only to such examples. . These polymerization initiators may be used alone or in combination of two or more.

A chain transfer agent may be used to adjust the molecular weight when polymerizing the monomers. A chain transfer agent can usually be used by mixing with a monomer. Examples of chain transfer agents include α-methylstyrene dimer, 2-(dodecylthiocarbonothioylthio)-2-methylpropionic acid, 2-(dodecylthiocarbonothioylthio)propionic acid, methyl 2-(dodecylthio Carbonothioylthio)-2-methylpropionate, 2-(dodecylthiocarbonothioylthio)-2-methylpropionic acid 3-azido-1-propanol ester, 2-(dodecylthiocarbonothioylthio)-2 - Mercaptan group-containing compounds such as methylpropionic acid pentafluorophenyl ester, lauryl mercaptan, dodecyl mercaptan, thioglycerol, inorganic salts such as sodium hypophosphite, sodium hydrogen sulfite, etc., but the present disclosure is only such examples is not limited to These chain transfer agents may be used alone or in combination of two or more. The amount of chain transfer agent is not particularly limited, but generally about 0.01 parts by weight to about 10 parts by weight per 100 parts by weight of total monomers is sufficient.

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.

The temperature at which the monomer is photopolymerized is not particularly limited, and a temperature of about 5 to 100° C. is usually preferred. The time required to polymerize the monomers varies depending on the polymerization conditions and cannot be determined unconditionally.

The polymerization reaction can optionally be terminated when the amount of remaining monomer is 20% by weight or less. In addition, the amount of the remaining monomer can be measured using, for example, gel permeation chromatography (GPC).

A polymer matrix can be obtained by polymerizing the monomers as described above.

In one embodiment, the monomer is polymerized in the absence of a crosslinker. In another embodiment, the monomer is polymerized in the presence of a crosslinker.

In one embodiment, the polymer matrix is thermally polymerized or photopolymerized. In another embodiment, the polymer matrix is thermally polymerized. In another embodiment, the polymer matrix is photopolymerized.

Methods for polymerizing the monomers include, for example, bulk polymerization, solution polymerization, emulsion polymerization, and suspension polymerization, but the present disclosure is not limited to these examples. Among these polymerization methods, bulk polymerization and solution polymerization are preferred.

Polymerization of the monomers can be carried out by, for example, radical polymerization, living radical polymerization, anionic polymerization, cationic polymerization, addition polymerization, polycondensation, catalytic polymerization, and the like.

When a 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 solution while stirring the obtained solution. The monomer can be polymerized by dissolving the initiator in a solvent and adding the monomer to the solution while stirring the resulting solution. The solvent is preferably an organic solvent compatible with the monomer.

Copolymers included in the conductive materials of the present disclosure are polymerized by using peroxide-based initiators (e.g., benzoyl peroxide and azobisisobutyronitrile, and analogs thereof) as polymerization initiators. may

When the above usable polymerization initiator is used as the polymerization initiator, the amount of the polymerization initiator is preferably about 0.01 to about 20 parts by weight per 100 parts by weight of the total monomers.

In one embodiment, electron beam polymerization is performed by irradiating the monomer with an electron beam. In one embodiment, the monomers can be polymerized by irradiation with electron beams only. In electron beam polymerization, the electron beam is irradiated in the presence of a photoinitiator in one embodiment and in the absence of a photoinitiator in another embodiment. Either embodiment is within the scope of this disclosure.

There are no particular restrictions on the polymerization reaction temperature and atmosphere when the monomers are thermally polymerized. Generally, the polymerization reaction temperature is from about 50°C to about 120°C. The atmosphere during the thermal polymerization reaction is preferably an inert gas atmosphere such as nitrogen gas. Further, the thermal polymerization reaction time of the monomers varies depending on the polymerization reaction temperature and the like, and cannot be generally determined, but is usually about 3 to 20 hours.

(2) Method for producing the polymer matrix contained in the conductive material The polymer (or polymer matrix) contained in the conductive material of the present disclosure is obtained by mixing two or more types of specific monomers, and under appropriate polymerization conditions, if necessary It can be produced by polymerization using an appropriate additive such as a polymerization initiator. The conductive material of the present disclosure can then be produced by mixing the polymer matrix with the conductive component and any other components and heating. Regarding the polymer, individual components, specific production conditions, etc. will be described in detail below.

In one aspect, the present disclosure provides at least one compound of the group of ether moiety-containing (meth)acrylic monomer components, at least one compound of the group of halogen-containing (meth)acrylic monomer components, and at least one compound of the group of hydroxy-containing (meth)acrylic monomer components. and at least one compound.

In another aspect, the present disclosure provides a method of making a conductive material comprising the copolymers described herein and a conductive component comprising:
Polymerizing at least one compound of the group of ether moiety-containing (meth)acrylic monomer components, at least one compound of the group of halogen-containing (meth)acrylic monomer components, and at least one compound of the group of hydroxyl-containing (meth)acrylic monomer components. obtaining the copolymer by
mixing said copolymer and a conductive component to obtain a mixture; and heating said mixture to produce a conductive material.

によって表されるモノマーであり、式中、Ｒ^１は、水素原子またはメチル基であり、Ｒ^２は、アルキルオキシ、シクロアルキルオキシもしくはアリールオキシ基で置換されている、アルキル、シクロアルキル、またはアリールであり、
前記ハロゲン含有（メタ）アクリルモノマー成分群の少なくとも一種の化合物は、式（２）

によって表されるモノマーであり、式中、Ｒ^３は、水素原子またはメチル基であり、Ｒ^４は、１個から置換可能な数までの同一又は異なるハロゲン原子で置換されたアルキル、シクロアルキル、またはアリールであり、
前記ヒドロキシ含有（メタ）アクリルモノマー成分群の少なくとも一種の化合物は、式（３）

により表される、第三の（メタ）アクリレートであり、Ｒ^５は、水素原子またはメチル基であり、Ｒ^６は、ヒドロキシ基で置換されている、アルキル、シクロアルキル、またはアリールである。 In a representative embodiment, at least one compound of the ether moiety-containing (meth)acrylic monomer component group has formula (1)

wherein 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 and
At least one compound of the halogen-containing (meth)acrylic monomer component group has the formula (2)

wherein R ³ is a hydrogen atom or a methyl group, and R ⁴ is an alkyl, cycloalkyl, substituted with from 1 to a substitutable number of the same or different halogen atoms, or is aryl,
At least one compound of the hydroxy-containing (meth)acrylic monomer component group has the formula (3)

A third (meth)acrylate represented by R ⁵ is a hydrogen atom or a methyl group and R ⁶ is an alkyl, cycloalkyl or aryl substituted with a hydroxy group.

One embodiment comprises at least one compound of the group of ether moiety-containing (meth)acrylic monomer components, at least one compound of the group of halogen-containing (meth)acrylic monomer components, and at least one compound of the group of hydroxy-containing (meth)acrylic monomer components. and a method for producing a copolymer comprising

In one embodiment, a crosslinker is used with at least one compound of the hydroxy-containing (meth)acrylic monomer component group.

One embodiment comprises at least one compound of the group of ether moiety-containing (meth)acrylic monomer components, at least one compound of the group of halogen-containing (meth)acrylic monomer components, and at least one compound of the group of hydroxy-containing (meth)acrylic monomer components. and at least one compound of the unsubstituted alkyl (meth)acrylic monomer component group.

In one embodiment of the present disclosure, the polymerization of said monomer is carried out according to a polymerization method selected from the group consisting of bulk polymerization method, solution polymerization method, emulsion polymerization method, and suspension polymerization method. While not wishing to be bound by theory, the monomers of the present disclosure can be polymerized by chain, sequential, or living polymerization.

(3-1) Method for preparing monomers Ether moiety-containing (meth)acrylic monomers, halogen-containing alkyl (meth)acrylates, hydroxy-containing alkyl (meth)acrylates, cross-linking agents, unsubstituted alkyl (meth)acrylates used in the present disclosure and (meth)acrylic monomers may be commercially available from manufacturers such as those exemplified in the Examples, or may be prepared according to methods well known to those skilled in the art.

(3-2) Manufacturing method by photopolymerization In one embodiment, the polymer matrix of the present disclosure is obtained in one step by subjecting a monomer (including multiple types of monomers) to exposure polymerization in the presence of a polymerization initiator. .
In one embodiment, the polymer matrix of the present disclosure comprises an ether moiety-containing (meth)acrylic monomer, a halogen-substituted alkyl (meth)acrylate, and a hydroxy-substituted alkyl (meth)acrylate as polymerization initiators. It can be produced by irradiating with ultraviolet rays in the presence.
Preferred examples of polymerization initiators include 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 take 0.5 to 3 hours, or 0.5 to 24 hours or longer.

(3-3) Method of Preparing Resin Solution In one embodiment, the polymer matrix of the present disclosure obtained by polymerizing monomers is dissolved in a solvent to form a resin solution. Examples of preferred solvents include heptane, octane, limonene, and the like.

(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 the resulting mixture is Obtained by heating. Those skilled in the art can use the descriptions herein and any technique known in the art to produce the conductive material using techniques other than this technique.

(Description of conductive components)
Examples of conductive components that can be targeted by the conductive material of the present disclosure include natural graphite such as flake graphite, graphite such as artificial graphite, acetylene black, ketjen black, channel black, furnace black, lamp black, thermal black, and the like. carbon-based materials such as carbon black, graphene, carbon nanotubes, fullerene; conductive fibers such as carbon fiber and metal fiber; carbon fluoride; metal particles such as copper, gold, nickel, tin, aluminum, zinc, iron, silver powder; conductive whiskers such as zinc oxide and potassium titanate; conductive metal oxides such as titanium oxide; organic conductive materials such as polyphenylene derivatives; is not. Each of these conductive components may be used alone, or two or more of them may be used in combination. Among these conductive components, carbon nanotubes, carbon black, graphene and metal particles are preferable from the viewpoint of obtaining a conductive film having excellent workability and moldability as well as excellent flexibility and extensibility. Black, graphene and silver particles are more preferred.

The content of the solid content of the conductive component in the total solid content of the polymer matrix and the conductive component varies depending on the type of the conductive component, and cannot be determined indiscriminately. From the viewpoint of obtaining a conductive film excellent in flexibility and elongation, it is preferably 1% by mass or more, excellent in workability and moldability, and from the viewpoint of obtaining a conductive film excellent in flexibility and elongation, Preferably, it is 100% by mass or less.

The content of the solid content of the conductive component in the total solid content of the polymer matrix and the conductive component is the conductive carbon-based component from the viewpoint of obtaining a conductive film having excellent workability and moldability, as well as excellent flexibility and stretchability. In the case of , it is preferably 1% by mass or more, more preferably 1.5% by mass or more, and still more preferably 2% by mass or more, and has excellent workability and moldability, as well as excellent flexibility and elongation Conductivity From the viewpoint of obtaining a film, it is preferably 25% by mass or less, more preferably 20% by mass or less, still more preferably 15% by mass or less, and even more preferably 3.5 to 10% by mass. On the other hand, when the conductive component is a metal-based component, it is preferably 70% by mass or more, more preferably 75% by mass or more, and still more preferably 80% by mass or more from the viewpoint of imparting good conductivity. From the viewpoint of obtaining a conductive film with excellent formability, the content is preferably 95% by mass or less, more preferably 90% by mass or less, and even more preferably 85% by mass or less.

(Use of conductive material)
The conductive material of the present disclosure is suitable for, for example, actuators, sensors used in industrial robots, wires, electrodes, substrates, power generation elements, speakers, microphones, noise cancellers, transducers, artificial muscles, small pumps, medical instruments, etc. It can be suitably used as a conductive film that can be used for and a raw material for the conductive film.

(preferred embodiment)
Preferred embodiments of the present disclosure are described below. The embodiments provided below are provided for a better understanding of the disclosure, and it is understood that the scope of the 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 disclosure can be used singly or in combination.

(Use for improving electrical conductivity)
In one aspect, the present disclosure relates to conductivity enhancement applications.

More specifically, in specific aspects, the present disclosure provides at least one compound of the ether moiety-containing (meth)acrylic monomer component group, at least one compound of the halogen-containing (meth)acrylic monomer component group, and a hydroxy-containing ( and at least one compound of the meth)acrylic monomer component group.

Conventionally, in a system in which a large amount of silver filler is present as in the present disclosure, it has been thought that the polymer composition does not affect the electrical conductivity, and therefore, sufficient studies have not been made. However, as a result of examination of polymers, it was confirmed that the system obtained by copolymerizing the fluorinated alkyl acrylate, the ether moiety-containing acrylate, and the hydroxy-containing acrylate had a lower resistivity than the conventional product. As a result of further examination, it was also confirmed that the resistivity decreased as the content of fluorine atoms contained in the fluorinated alkyl acrylate increased. From the viewpoint of resin solubility, 2,2,2-trifluoroethyl acrylate (V#3F) was used in this system.

In one specific embodiment, the conductive material of the present disclosure comprises an alkoxy-substituted alkyl acrylate, which is an embodiment of an ether moiety-containing (meth)acrylic monomer, and a fluorinated alkyl acrylate, which is an embodiment of a halogen-containing (meth)acrylic monomer. A copolymer of a (meth)acrylate and a hydroxy-containing acrylate, which is one embodiment of a hydroxy-containing (meth)acrylic monomer, and a conductive component. In this way, the copolymer can improve the electrical conductivity of the conductive component.

By providing this technique of the present disclosure, the conductivity of any conductive component can be improved.

In one preferred embodiment, the copolymers used in the present disclosure are advantageously copolymers of alkoxy-substituted alkyl acrylates, fluorinated alkyl (meth)acrylates and hydroxy-containing acrylates. The reason for this includes, without wishing to be bound by theory, the effect of repelling the compound (surfactant effect). Fluorine-based resins are used as antifouling coating agents and mold release agents, and have the effect of repelling compounds (surfactant effect). Regarding the reason why the resistivity decreased in the present disclosure, it is considered that the surface active effect of the fluorine compound caused the fluorinated alkyl (meth)acrylate and the silver particles to repel each other, so that the silver particles were more densely packed. . In addition, it is considered that the polarity of the copolymer and the like also affect the decrease in resistivity, and it is considered that these factors have a combined effect, resulting in the decrease in resistivity. Furthermore, it is an unexpected result that it is considered that the effect is manifested with such a small amount of addition as in the examples.

In one embodiment, the conductive component is similar to the conductivity enhancers described above.

によって表される第一の（メタ）アクリレートであり、式中、Ｒ^１は、水素原子またはメチル基であり、
Ｒ^２は、アルキルオキシ基、シクロアルキルオキシ基もしくはアリールオキシ基で置換されている、アルキル、シクロアルキル、またはアリールである。 In one embodiment, the compound of the ether moiety-containing (meth)acrylic monomer component group has formula (1)

is a first (meth)acrylate represented by wherein R ¹ is a hydrogen atom or a methyl group;
R ² is alkyl, cycloalkyl, or aryl substituted with an alkyloxy, cycloalkyloxy, or aryloxy group.

In one embodiment, ^R2 is an alkyl, cycloalkyl, or aryl group substituted with an alkyloxy group. In one embodiment, R ² is an alkyl, cycloalkyl, or aryl group substituted with a cycloalkyloxy group. In one embodiment, R ² is an alkyl, cycloalkyl, or aryl group substituted with an aryloxy group.

In one embodiment, the compound represented by formula (1) is an alkyl(meth)acrylate substituted with an alkyloxy, cycloalkyloxy or aryloxy group. In one embodiment, the compound represented by Formula (1) is an alkyl (meth)acrylate substituted with an alkyloxy or cycloalkyloxy group. In one embodiment, compounds represented by Formula (1) are alkyloxy-substituted alkyl (meth)acrylates.

によって表される第二の（メタ）アクリレートであり、式中、Ｒ^３およびＲ^４は、本明細書中で定義されるとおりである。 In one embodiment, the compound of the halogen-containing (meth)acrylic monomer component group has formula (2)

is a second (meth)acrylate represented by wherein R ³ and R ⁴ are as defined herein.

In one embodiment, R ⁴ is an alkyl, cycloalkyl, or aryl group substituted with a halogen group. In one embodiment, R ⁴ is an alkyl group, cycloalkyl group, or aryl group substituted with a fluorine atom. In one embodiment, R ⁴ is an alkyl, cycloalkyl, or aryl group substituted with a chlorine atom. In one embodiment, R ⁴ is an alkyl, cycloalkyl, or aryl group substituted with a bromine atom.

In one embodiment, compounds represented by formula (2) are haloalkyl (meth)acrylates.

によって表される第三の（メタ）アクリレートであり、式中、Ｒ^５およびＲ^６は、本明細書中で定義されるとおりである。 In one embodiment, the compound of the hydroxy-containing (meth)acrylic monomer component group has formula (3)

is a third (meth)acrylate represented by wherein R ⁵ and R ⁶ are as defined herein.

^In one embodiment, R6 is an alkyl group substituted with a hydroxy group. ^In one embodiment, R6 is a cycloalkyl group substituted with a hydroxy group. ^In one embodiment, R6 is an aryl group substituted with a hydroxy group.

In one embodiment, compounds represented by Formula (3) are hydroxy-substituted alkyl (meth)acrylates. In preferred embodiments, the compound represented by formula (3) is 4-hydroxybutyl acrylate.

Said hydroxy-containing (meth)acrylates can be used with corresponding suitable cross-linking agents. Examples of the cross-linking agent include, but are not limited to, isocyanate, hexamethylene diisocyanate, polyisocyanate, and Duranate ^TM (manufactured by Asahi Kasei Corporation).

In one embodiment, said hydroxy-substituted alkyl (meth)acrylates are used optionally with a corresponding suitable cross-linking agent. In one embodiment, the hydroxy-substituted alkyl (meth)acrylate may optionally be used with a cross-linking agent to be cross-linked. Examples of cross-linking agents can include, but are not limited to, formaldehyde and isocyanates. By being used together with a cross-linking agent, the durability of the binder resin can be improved, and the flexibility and/or durability of the conductive material can be improved.

により表される第四の（メタ）アクリレートであり、式中、Ｒ^７は、水素原子またはメチル基であり、Ｒ^８は、非置換のアルキル、シクロアルキル、またはアリールであるが、ただし、Ｒ^８はエーテル、ハロゲンおよび水酸基で置換されたアルキル、シクロアルキル、またはアリールではない。 In one embodiment, the compound of the unsubstituted alkyl (meth)acrylic monomer component group has formula (4)

A fourth (meth)acrylate represented by wherein R ⁷ is a hydrogen atom or a methyl group and R ⁸ is an unsubstituted alkyl, cycloalkyl, or aryl, with the proviso that R ⁸ is not ether, halogen and hydroxyl substituted alkyl, cycloalkyl or aryl.

^In one embodiment, R8 is an unsubstituted alkyl group. ^In one embodiment, R8 is an unsubstituted cycloalkyl group. ^In one embodiment, R8 is an unsubstituted aryl group.

^In one embodiment, R8 is an unsubstituted alkyl group having 11 or more carbon atoms. In one embodiment, R ⁸ is an unsubstituted alkyl group having 11-30 carbon atoms. In one embodiment, R ⁸ is an unsubstituted alkyl group having 11-24 carbon atoms.

^In another embodiment, R8 is an unsubstituted alkyl group having 13 or more carbon atoms. In one embodiment, R ⁸ is an unsubstituted alkyl group having 13-30 carbon atoms. In one embodiment, R ⁸ is an unsubstituted alkyl group having 13-24 carbon atoms.

^In yet another embodiment, R8 is an unsubstituted alkyl group having 18 or more carbon atoms. In one embodiment, R ⁸ is an unsubstituted alkyl group having 18-30 carbon atoms. In one embodiment, R ⁸ is an unsubstituted alkyl group having 18-24 carbon atoms.

In one embodiment, the compound represented by formula (1) is 2-methoxyethyl acrylate, (3-ethyloxetan-3-yl)methyl acrylate or 2,3-epoxypropyl methacrylate.

In one embodiment, the compound represented by formula (1) is 2-methoxyethyl acrylate.

In one embodiment, the compound represented by formula (2) is 2,2,2-trifluoroethyl acrylate.

In one embodiment, the compound represented by formula (3) is 4-hydroxybutyl acrylate.

In one embodiment, an isocyanate is used as a cross-linking agent to cross-link the compound represented by formula (3).

In one embodiment, the compound represented by formula (4) is isostearyl acrylate, stearyl acrylate, lauryl acrylate, or ethyl acrylate.

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.

In yet another embodiment, the halogen-containing (meth)acrylate is 2,2,2-trifluoroethyl acrylate.

In yet another embodiment, the hydroxy-containing (meth)acrylate is 4-hydroxybutyl acrylate.

In another embodiment, the unsubstituted alkyl (meth)acrylate is isostearyl acrylate, stearyl acrylate, lauryl acrylate, or ethyl acrylate.

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.

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, The compound represented by formula (3) is 4-hydroxybutyl acrylate.

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, Compounds represented by formula (3) are 4-hydroxybutyl acrylates and these acrylates are used or polymerized with a cross-linking agent.

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, and the compound represented by formula ( The compound represented by 3) is 4-hydroxybutyl acrylate, and the compound represented by formula (4) is isostearyl acrylate.

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, The compound represented by formula (3) is 4-hydroxybutyl acrylate and the compound represented by formula (4) is isostearyl acrylate, these acrylates being used or polymerized with a cross-linking agent.

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, and the compound represented by formula ( The compound represented by 3) is 4-hydroxybutyl acrylate, and the compound represented by formula (4) is ethyl acrylate.

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, The compound represented by formula (3) is 4-hydroxybutyl acrylate and the compound represented by formula (4) is ethyl acrylate, these acrylates being used or polymerized with a cross-linking agent.

In one embodiment, A) at least one compound of the ether moiety-containing (meth)acrylic monomer component group, B) at least one compound of the halogen-containing (meth)acrylic monomer component group, and C) hydroxy-containing (meth)acrylic The mass ratio to at least one compound of the monomer component group is A:B:C=20-80:80-20:0.2-2.0, and A:B:C=25-70:70- 25:0.3 to 1.5, and A:B:C=29 to 65:70 to 35:0.5 to 1.5. When a cross-linking agent is further included, A: B: C: cross-linking agent = 20-80: 80-20: 0.2-2.0: 0.2-2.0, A: B: C: cross-linking Agent = 25 to 70: 70 to 25: 0.3 to 1.5: 0.3 to 1.5, and further A: B: C: Crosslinking agent = 29 to 65: 70 to 35: 0.5 ˜1.5: 0.5 to 1.5. When D) further contains at least one compound of the unsubstituted alkyl (meth)acrylic monomer component group, A:B:C:D=20 to 80:80 to 20:0.2 to 2.0: 10-70, A:B:C:D=25-70:70-25:0.3-1.5:20-60, and A:B:C:D=29-65: 70-35: 0.5-1.5: 30-50. When a cross-linking agent is further included, A: B: C: D: cross-linking agent = 20 to 80: 80 to 20: 0.2 to 2.0 :: 10 to 700.2 to 2.0, and A: B: C:: D crosslinker = 25-70: 70-25: 0.3-1.5: 20-60: 0.3-1.5, further A: B: C: D: cross-linking Agent = 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.

(Conductive material)
In another aspect, the present disclosure provides a conductive material with improved electrical conductivity.

In one specific aspect, the present disclosure includes ether moiety-containing (meth)acrylic monomer components, halogen-containing (meth)acrylic monomer components, and hydroxy-containing (meth)acrylic monomer components, optionally A conductive material is provided that includes a copolymer of a compound that includes a crosslinker and a conductive component. A preferred embodiment of the conductive material can utilize any of the embodiments or combinations thereof described herein, any embodiment described in the (Conductivity Enhancing Applications) section herein. can be applied in combination with one or more.

(manufacturing method)
In one aspect, the present disclosure provides methods of making the electrically conductive materials and conductivity enhancers of the present disclosure.

In specific aspects, the present disclosure provides ether moiety-containing (meth)acrylic monomer components, halogen-containing (meth)acrylic monomer components, hydroxy-containing (meth)acrylic monomer components, and unsubstituted alkyl (meth)acrylic monomers. A method is provided for producing a conductive material comprising a homopolymer or copolymer of a compound comprising at least one component group and optionally a cross-linking agent 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 a conductive component to obtain a mixture, and heating the mixture to produce a conductive material. do. A preferred embodiment of the manufacturing method may utilize any of the embodiments or combinations thereof described herein, any embodiment described in the (Conductivity Enhancing Application) section herein. can be applied in combination with one or more.

In the step of obtaining a copolymer by photopolymerizing the above monomers and polymerizable monomers in the production method of the present disclosure, the following conditions are typically preferred: 5° C. to 100° C. under atmospheric pressure.

In the step of mixing the copolymer and the conductive component in the manufacturing method of the present disclosure to obtain a mixture, the following conditions are typically preferred: stirring with a planetary mixing stirrer at room temperature under atmospheric pressure.

In the step of heating the mixture to form the conductive material in the manufacturing method of the present disclosure, the following conditions are typically preferred: 120° C. to 150° C. under atmospheric pressure.

(copolymer)
The present disclosure provides copolymers using the disclosed technology.

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.

によって表されるモノマーであり、
前記ハロゲン含有（メタ）アクリレートは、式（２）

によって表されるモノマーであり、
前記ヒドロキシ含有（メタ）アクリレートは、式（３）

によって表されるモノマーであり、
式中、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５、Ｒ^６、Ｒ^７、およびＲ^８は、本明細書中で定義されるとおりである。 In a representative embodiment, the ether moiety-containing (meth)acrylate has formula (1)

is a monomer represented by
The halogen-containing (meth)acrylate has the formula (2)

is a monomer represented by
The hydroxy-containing (meth)acrylate has the formula (3)

is a monomer represented by
wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ are as defined herein.

^In one embodiment, R6 is an alkyl group substituted with one or more hydroxy groups.

In one embodiment, the copolymer is a copolymer comprising an alkoxy-substituted alkyl (meth)acrylate and a haloalkyl (meth)acrylate.

Said hydroxy-containing (meth)acrylates may be used together with a cross-linking agent during copolymerization.

Said copolymers are used, for example, as matrices for conductive materials.

In one embodiment, the copolymer comprises the ether moiety-containing (meth)acrylate represented by formula (1), the halogen-containing (meth)acrylate represented by formula (2), and the halogen-containing (meth)acrylate represented by formula (3). are copolymers with hydroxy-containing (meth)acrylates that are

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.

によって表され、
式中、Ｒ^１は、水素原子またはメチル基であり、Ｒ^２は、アルキルオキシ基、シクロアルキルオキシ基もしくはアリールオキシ基で置換されている、アルキル、シクロアルキル、またはアリールであり、
該ハロゲン含有基で置換されたアルキル（メタ）アクリレートは、式（２）

によって表され、
式中、Ｒ^３は、水素原子またはメチル基であり、
Ｒ^４は、１個から置換可能な数までの同一又は異なるハロゲン原子で置換されたアルキル、シクロアルキル、またはアリールであるが、ただし、Ｒ^４は、エーテル基を含むアルキル、シクロアルキル、またはアリールではなく、
該ヒドロキシ含有（メタ）アクリルモノマーは、式（３）、

によって表され、
式中、Ｒ^５は、水素原子またはメチル基であり、Ｒ^６は、ヒドロキシ基で置換されている、アルキル、シクロアルキル、またはアリールであるが、ただし、Ｒ^６はエーテルおよびハロゲンで置換されたアルキル、シクロアルキル、またはアリールではなく、該ヒドロキシ含有（メタ）アクリルモノマーは、必要に応じて架橋剤を用いて架橋されてもよい。このコポリマーは、例えば、導電材のマトリクスとして使用される。 The present disclosure also relates to a method of making 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)

is represented by
wherein 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 alkyl (meth)acrylate substituted with the halogen-containing group has the formula (2)

is represented by
wherein R3 is a hydrogen atom or a methyl group ^,
R ⁴ is an alkyl, cycloalkyl, or aryl substituted with from 1 to the substitutable number of the same or different halogen atoms, provided that R ⁴ is an alkyl, cycloalkyl, or aryl containing an ether group not,
The hydroxy-containing (meth)acrylic monomer has the formula (3),

is represented by
wherein R ⁵ is a hydrogen atom or a methyl group and R ⁶ is an alkyl, cycloalkyl, or aryl substituted with a hydroxy group, provided that R ⁶ is ether and halogen substituted Rather than being alkyl, cycloalkyl, or aryl, the hydroxy-containing (meth)acrylic monomers may optionally be crosslinked using a crosslinker. This copolymer is used, for example, as a matrix for conductive materials.

により表される（メタ）アクリレートであり、式中、Ｒ^７およびＲ^８は、本明細書中で定義されるとおりである。 In one embodiment, the present disclosure relates to a method of making a copolymer comprising an unsubstituted alkyl (meth)acrylate in said copolymer,
The unsubstituted alkyl (meth)acrylate has the formula (4)

is a (meth)acrylate represented by where R ⁷ and R ⁸ are as defined herein.

^In one embodiment, R8 is an unsubstituted alkyl group having 11 or more carbon atoms. In one embodiment, R ⁸ is an unsubstituted alkyl group having 11-30 carbon atoms. In one embodiment, R ⁸ is an unsubstituted alkyl group having 11-24 carbon atoms.

^In one embodiment, R8 is an unsubstituted alkyl group having 13 or more carbon atoms. In one embodiment, R ⁸ is an unsubstituted alkyl group having 13-30 carbon atoms. In one embodiment, R ⁸ is an unsubstituted alkyl group having 13-24 carbon atoms.

^In one embodiment, R8 is an unsubstituted alkyl group having 18 or more carbon atoms. In one embodiment, R ⁸ is an unsubstituted alkyl group having 18-30 carbon atoms. In one embodiment, R ⁸ is an unsubstituted alkyl group having 18-24 carbon atoms.

The present disclosure provides matrix applications.
In one aspect, the present disclosure provides 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) a copolymer of a compound comprising an acrylic monomer component and at least one unsubstituted alkyl (meth)acrylic monomer component of formula (4), and optionally a cross-linking agent;
A composition is provided for use as a matrix in a conductive material comprising a conductive component.

(blend)
The disclosure also provides mixtures.

In one aspect, the present disclosure provides a mixture of materials (ie, a composition comprising a copolymer and a metal-based component). Specifically, the present disclosure provides mixtures of said copolymers and metals.

In an exemplary embodiment, the mixture comprises at least one compound of the ether moiety-containing (meth)acrylic monomer component group of formula (1) and at least one halogen-containing (meth)acrylic monomer component group of formula (2). and mixtures of metals.

In one embodiment, the mixture comprises 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) with at least one compound of the hydroxy-containing (meth)acrylic monomer component group of formula (3), and a mixture of metals.

In one embodiment, the mixture comprises 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 copolymer of 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 mixture of metals is.

In one embodiment, metals include silver, copper, gold, aluminum, zinc, tin, nickel, and/or iron. In preferred embodiments, the metal is silver. Without wishing to be bound by theory, this is because silver is highly conductive and resistant.

(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 "or". When "within a range of two values" is stated herein, the range includes the two values themselves.

All references, such as scientific articles, patents, patent applications, etc., cited herein are hereby incorporated by reference in their entireties to the same extent as if each were specifically set forth.

The present disclosure has been described above showing preferred embodiments for ease of understanding. While the present disclosure will now be described based on the examples, the foregoing description and the following examples are provided for illustrative purposes only and not for the purpose of limiting the present disclosure. Accordingly, the scope of the present disclosure is not limited to the embodiments or examples specifically described herein, but only by the claims.

Examples are described below. The handling of the organisms used in the following examples complied with the standards set by regulatory agencies, where necessary. As reagents, the products specifically described in the examples were used, but equivalent products from other manufacturers (Sigma-Aldrich, etc.) can be substituted.

(Example A: Preparation of polymer matrix)
In this example, a polymer matrix was prepared.

(Example 1)
2-Methoxyethyl acrylate as monomer A (62 g, manufactured by Osaka Organic Chemical Industry Co., Ltd., trade name 2-MTA), 2,2,2-trifluoroethyl acrylate as monomer B (36 g, manufactured by Osaka Organic Chemical Industry Co., Ltd., commercial name Viscoat V#3F), 4-hydroxybutyl acrylate (1 g, manufactured by Osaka Organic Chemical Industry Co., Ltd., trade name Viscoat 4-HBA) as a monomer C, and 2,4,6-trimethylbenzoyldiphenylphosphine oxide (1 g) as a polymerization initiator. , manufactured by BASF Corporation, trade name Irgacure (registered trademark) TPO), and α-methylstyrene dimer (1 g, manufactured by NOF Corporation, trade name Nofmer MSD) as a chain transfer agent. A monomer component was obtained. After injecting the obtained monomer component into a transparent glass mold (length: 100 mm, width: 100 mm, depth: 2 mm), the monomer component was irradiated with ultraviolet rays so that the irradiation dose was 0.36 mW / cm ² . A polymer was obtained by subjecting the monomer components to bulk polymerization for 2 hours.

Preparation of Conductive Material Precursor The obtained polymer (2.50 g) was dissolved in 3-methoxy-3-methyl-1-butanol (7.50 g) to obtain a resin solution.
For the resin solution (4.00 g), silver filler (4.00 g, manufactured by Fukuda Metal Foil & Powder Co., Ltd., trade name AgC-A), cross-linking agent (0.010 g, manufactured by Asahi Kasei Co., Ltd., trade 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, trade name RHEOBYK-410) were mixed in Mazerustar manufactured by Kurabo Industries, Ltd., and conductive A material precursor was obtained.

(Coating film formation)
The resulting conductive material precursor was applied to a release polyethylene terephthalate film (manufactured by Mitsui Chemicals Tohcello, Inc., trade name: Separator SP-PET PET-01-Bu) as a release film to form a coating film.

(Conductive film)
The obtained coating film was heated in an oven at 120° C. for 30 minutes to obtain a conductive film having a thickness of approximately 40 μm.

(Examples 2-4)
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 cross-linking agent were changed as shown in the table below.

(Example 5)
Ethyl acrylate (EA, 31 g) was newly added as monomer D, 2-methoxyethyl acrylate (31 g, manufactured by Osaka Organic Chemical Industry Co., Ltd., trade name 2-MTA) as monomer A, and 2,2,2 as monomer B. -Trifluoroethyl acrylate (36 g, manufactured by Osaka Organic Chemical Industry Co., Ltd., trade name Viscoat V#3F), 4-hydroxybutyl acrylate as monomer C (1 g, manufactured by Osaka Organic Chemical Industry Co., Ltd., trade name Viscoat 4-HBA), cross-linked Isocyanate (1 g) as an agent and 2,4,6-trimethylbenzoyldiphenylphosphine oxide (1 g, manufactured by BASF, trade name Irgacure (registered trademark) TPO) as a polymerization initiator were changed to mix in the above amounts. was carried out in the same manner as in Example 1 to obtain an acrylic resin solution.

(Comparative Examples 1 and 2)
A corresponding polymer was obtained using only 2-MTA (monomer A) and V#3F (monomer B) as monomers. The parts by weight of the composition of monomer A and monomer B used are as shown in Table 1.

(Comparative Example 3)
Similarly, V#3F (monomer B), 4-HBA (monomer C) and isocyanate (crosslinker) were used to obtain the corresponding polymer. The parts by weight of the monomer B, monomer C and cross-linking agent used are shown in Table 1.

(Comparative Example 4)
Similarly, V#3F (monomer B), 4-HBA (monomer C), isocyanate (crosslinker) and EA (monomer D) were used to obtain the corresponding polymer. The parts by weight of the monomer B, monomer C and cross-linking agent used are shown in Table 1.

(Example B: Preparation of conductive film)
In this example, a conductive film was prepared.

(Conductive material precursor)
Silver filler (7.20 g, manufactured by Fukuda Metal Foil & Powder Co., Ltd., trade name AgC-A) to each acrylic resin solution (6.00 g) obtained in Example A, and 2-(2-butoxyethoxy) as a dispersant ) Ethanol (0.10 g) was mixed with Mazerustar manufactured by Kurabo Industries, Ltd. to obtain a conductive material precursor.

(Coating film formation)
The resulting conductive material precursor was applied as a release film to a release polyethylene terephthalate film (manufactured by Mitsui Chemicals Tohcello Co., Ltd., trade name Separator SP-PET PET-01-Bu) to form a coating film.

(Conductive film)
The obtained coating film was heated in an oven at 120° C. for 30 minutes to obtain a conductive film having a thickness of approximately 40 μm.

(result)
Conductive films were made according to the procedures described in Examples A and B. Table 1 shows the results.

(Example C: Measurement of volume resistivity)
The conductive film obtained in Example B was cut into a length of 0.5 cm and a width of 2.00 cm, and measured by the four-probe method using Loresta GP (manufactured by Mitsubishi Chemical Analytech Co., Ltd.).

(result)
Table 1 shows the results.

(Example D: Confirmation of change in resistance value)
In this example, a change in resistance value was confirmed.

(Resistance measurement)
The conductive film obtained above was cut into a length of 0.5 cm and a width of 2.00 cm, and the distance between the electrodes was fixed to 1.00 cm. A resistance value (ΩA) was measured.

(Resistance value 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) was measured in this state. A change in resistance value was calculated as follows.
Resistance change = ΩB/ΩA

(result)
Results are shown in Table 1. The smaller the change in resistance value (closer to 1), the smaller the influence of the shape change, which means that the durability is high. Therefore, resistance change can also be evaluated as durability.

(Example E: Measurement of flexibility)
The conductive film obtained in the above example was cut into test pieces (dumbbell-shaped No. 7). Flexibility of this test piece was measured using a tensile tester (product name: TENSILON RTG-1310, manufactured by A&D Co., Ltd.) at a tensile speed of 50 mm/min. Young's modulus was calculated from the obtained value.

(result)
Table 1 shows the results.

(Note)
While the present disclosure has been illustrated using the preferred embodiments thereof, it is understood that the present disclosure is to be construed in scope only by the claims. The patents, patent applications and other publications cited herein are hereby incorporated by reference in their entirety to the same extent as if the content itself were specifically set forth herein. It is understood.

The conductive material enhancer of the present disclosure can be used to provide an efficient conductive material and can be used in industries requiring conductive materials.

Claims (16)

A) at least one compound of the ether moiety-containing (meth)acrylic monomer component group;
B) at least one compound from the group of halogen-containing (meth)acrylic monomer components;
C) at least one compound of the hydroxy-containing (meth)acrylic monomer component group,
A composition or combination for improving the electrical conductivity of an electrical conductor. 11. The composition or combination of Claim 1, further comprising a cross-linking agent. 3. The composition or combination of claim 2, wherein the cross-linking agent has functional groups that cross-link the C component group compounds. A composition or combination according to any one of claims 1 to 3 further comprising D) at least one compound of the unsubstituted alkyl (meth)acrylic monomer component group. The compound of the ether moiety-containing (meth)acrylic monomer component group has the formula (1)

is a first (meth)acrylate represented by
R ¹ is a hydrogen atom or a methyl group,
R ² is alkyl, cycloalkyl, or aryl substituted with an alkyloxy, cycloalkyloxy, or aryloxy group;
A composition or combination according to any one of claims 1-4. The compound of the halogen-containing (meth)acrylic monomer component group has the formula (2)

is a second (meth)acrylate, represented by
R ³ is a hydrogen atom or a methyl group,
R ⁴ is alkyl, cycloalkyl, or aryl substituted with from 1 to the substitutable number of the same or different halogen atoms;
A composition or combination according to any one of claims 1-5. At least one compound of the hydroxy-containing (meth)acrylic monomer component group has the formula (3)

is a third (meth)acrylate represented by
^R5 is a hydrogen atom or a methyl group,
R ⁶ is alkyl, cycloalkyl, or aryl substituted with a hydroxy group;
A composition or combination according to any one of claims 1-6. At least one compound of the unsubstituted alkyl (meth) acrylic monomer component group has the formula (4)

is a fourth (meth)acrylate represented by
^R7 is a hydrogen atom or a methyl group,
R ⁸ is unsubstituted alkyl, cycloalkyl, or aryl;
A composition or combination according to any one of claims 1-8. The first (meth)acrylate includes tetrahydrofurfuryl (meth)acrylate, phenoxyethyl (meth)acrylate, ethoxyethoxyethyl (meth)acrylate, 2-methoxyethyl (meth)acrylate, methoxytriethylene glycol (meth)acrylate. , methoxypolyethylene glycol (meth)acrylate, methoxypolyethyleneglycol (meth)acrylate, (2-methyl-2-ethyl-1,3-dioxolan-4-yl)methyl (meth)acrylate, (3-ethyloxetane-3- yl) methyl (meth) acrylate, and (5-ethyl-1,3-dioxan-5-yl) methyl (meth) acrylate, containing at least one selected from the group consisting of, any one of claims 1 to 8 A composition or combination according to claim 1. The second (meth)acrylate includes 2,2,2-trifluoroethyl (meth)acrylate, 2,2,3,3-tetrafluoropropyl (meth)acrylate, 1H,1H,5H-octafluoropentyl ( The composition according to any one of claims 1 to 9, comprising at least one selected from the group consisting of meth)acrylates and 1H,1H,2H,2H-tridecafluorooctyl (meth)acrylates. Or a combination. 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. , a composition or combination according to any one of claims 1-10. The fourth (meth) acrylate is selected from the group consisting of ethyl acrylate, isostearyl acrylate, stearyl acrylate, and lauryl acrylate, according to any one of claims 1 to 11. composition or combination. A conductive material comprising a composition or combination according to any one of claims 1 to 12, a conductive component, and a substrate. 14. The conductive material of claim 13, wherein the conductive component comprises a metal-based component such as a metal component, a metal oxide, a metal carbide, a conductive carbon-based component, a conductive organic compound, a conductive polymer, or combinations thereof. A composition or combination according to any one of claims 1 to 12, which improves the flexibility of the conductive component or material. A composition or combination according to any one of claims 1 to 12 which improves the durability of a conductive component or material.