WO2021029362A1 - 新規導電材焼成温度低下剤 - Google Patents

新規導電材焼成温度低下剤 Download PDF

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WO2021029362A1
WO2021029362A1 PCT/JP2020/030369 JP2020030369W WO2021029362A1 WO 2021029362 A1 WO2021029362 A1 WO 2021029362A1 JP 2020030369 W JP2020030369 W JP 2020030369W WO 2021029362 A1 WO2021029362 A1 WO 2021029362A1
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substituted
unsubstituted
hydrogen atom
meth
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慎一朗 岡本
亮平 池田
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大阪有機化学工業株式会社
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D303/00Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02Compounds containing oxirane rings
    • C07D303/12Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/16Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D305/00Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
    • C07D305/02Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D305/04Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D305/06Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring atoms
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10Esters
    • C08F20/26Esters containing oxygen in addition to the carboxy oxygen
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/26Esters containing oxygen in addition to the carboxy oxygen
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00Use of inorganic substances as compounding ingredients
    • C08K3/02Elements
    • C08K3/08Metals
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04Homopolymers or copolymers of esters
    • C08L33/14Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01BCABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/20Conductive material dispersed in non-conductive organic material
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01BCABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B13/00Apparatus or processes specially adapted for manufacturing conductors or cables

Definitions

  • the present disclosure relates to a new conductive material firing temperature lowering agent, a new conductivity improving agent, and related technologies. More specifically, the present disclosure relates to a composition for lowering the firing temperature of the conductive material and improving the conductivity of the conductive material, which comprises the compound represented by the formula (4) described in the specification.
  • the present disclosure provides a conductive material containing a desired combination of conductive components and a base material.
  • the disclosure provides, for example:
  • a composition for lowering the firing temperature of a conductive material which comprises the compound represented by.
  • R 1 is a hydrogen atom or a methyl group and R 2 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted non-aryl heterocycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • n is an integer of 0 or 1, Composition.
  • composition according to any one of the preceding items, wherein n 0 and the compound represented by the formula (4) has one or two or more vinyloxy groups.
  • the conductive material contains a homopolymer or copolymer of a compound represented by the formula (4) and a conductive component.
  • the conductive material comprises a homopolymer or copolymer of an alkyl (meth) acrylate substituted with the oxygen-containing ring and a conductive component.
  • the copolymer is a copolymer of a compound represented by the formula (4) and a second (meth) acrylic monomer.
  • R 2 is an alkyl group or a cycloalkyl group which may be substituted with an oxygen-containing group, and the oxygen-containing group is a hydroxy, hydroxyalkyl, vinyloxyalkyl, alkoxy, oxylan ring or oxetane ring.
  • R 1 is a hydrogen atom or a methyl group.
  • R 2 is hydroxy, alkoxy, oxirane ring and an alkyl group substituted by a substituent from one selected from the group consisting of oxetane ring to substitutable number, The composition according to any one of the preceding paragraphs.
  • the alkyl (meth) acrylate substituted with the oxygen-containing group is the formula (1).
  • R 1 is a hydrogen atom or a methyl group and R 2 is alkoxy, oxirane ring and an alkyl group which is substituted with up substitutable number from 1 selected from the group consisting of oxetane ring, The composition according to any one of the preceding paragraphs.
  • the alkyl (meth) acrylate substituted with the oxygen-containing ring is the formula (1).
  • R 1 is a hydrogen atom or a methyl group and R 2 is an alkyl group substituted with one or more oxylan or oxetane rings, The composition according to any one of the preceding paragraphs.
  • R 1 is a hydrogen atom or a methyl group.
  • the second (meth) acrylic monomer has the formula (2).
  • R 3 is a hydrogen atom or a methyl group and R 4 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted non-aryl heterocycloalkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, but however, R 4 is also an alkyl group substituted with an oxygen-containing rings, nor alkyl are alkoxy-substituted, The composition according to any one of the preceding paragraphs.
  • R 4 is an unsubstituted alkyl group having 2-10 carbon atoms, preceding composition according to any one of claims.
  • (Section A6c) R 4 is an unsubstituted alkyl group having 11 or more carbon atoms, the preceding composition according to any one of claims.
  • (Section A6d) R 4 is an unsubstituted alkyl group having 13 or more carbon atoms, the preceding composition according to any one of claims.
  • Section A6E R 4 is an unsubstituted alkyl group having 18 or more carbon atoms, the preceding composition according to any one of claims.
  • the compound represented by the formula (4) of (Item A7a) is 4-hydroxybutyl vinyl ether, 2-methoxyethyl acrylate, (3-ethyloxetane-3-yl) methyl acrylate or 2,3-epoxypropyl methacrylate.
  • the alkyl (meth) acrylate substituted with the oxygen-containing group is 2-methoxyethyl acrylate, (3-ethyloxetane-3-yl) methyl acrylate or 2,3-epoxypropyl methacrylate.
  • (Item A7c) Any one of the preceding items, wherein the alkyl (meth) acrylate substituted with the oxygen-containing ring is (3-ethyloxetane-3-yl) methyl acrylate or 2,3-epoxypropyl methacrylate.
  • the composition according to. (Item A7d) The composition according to any one of the preceding items, wherein the compound represented by the formula (4) is 4-hydroxybutyl vinyl ether.
  • (Item A8) The composition according to any one of the preceding items, wherein the second (meth) acrylic monomer is ethyl acrylate, stearyl acrylate, isostearyl acrylate or lauryl acrylate.
  • R 1 is a hydrogen atom or a methyl group and R 2 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted non-aryl heterocycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • n is an integer of 0 or 1, Conductive material.
  • the compound represented by the formula (4) is a conductive material which is an alkyl (meth) acrylate substituted with an oxygen-containing group.
  • the compound represented by the formula (4) is a conductive material which is an alkyl (meth) acrylate substituted with an oxygen-containing ring.
  • a conductive material in which n 0 and R 2 is an alkyl group or a cycloalkyl group which may be substituted with an oxygen-containing group.
  • (Item A11a) Equation (4) A method for producing a copolymer of a compound represented by the above and a conductive material containing a conductive component. A step of obtaining a copolymer by polymerizing a compound represented by the formula (4) and a polymerizable monomer. Including the steps of mixing the copolymer and the conductive components to obtain a mixture, and heating the mixture to produce a conductive material.
  • R 1 is a hydrogen atom or a methyl group and R 2 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted non-aryl heterocycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • n is an integer of 0 or 1
  • Method. (Item A11b) The method according to any one of the preceding items, wherein the compound represented by the above formula (4) is an alkyl (meth) acrylate substituted with an oxygen-containing group.
  • R 1 is a hydrogen atom or a methyl group and R 2 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted non-aryl heterocycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • n is an integer of 0 or 1 and
  • the second (meth) acrylic monomer has the formula (2).
  • R 3 is a hydrogen atom or a methyl group and R 4 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted non-aryl heterocycloalkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, but however, R 4 is also an alkyl group substituted with an oxygen-containing rings, nor alkyl are alkoxy-substituted, Copolymer.
  • the compound represented by the formula (4) is the formula (1).
  • An alkyl (meth) acrylate substituted with an oxygen-containing group represented by R 1 is a hydrogen atom or a methyl group and R 2 is an alkyl group substituted with one or more oxygen-containing groups, The copolymer according to any one of the preceding paragraphs.
  • the compound represented by the formula (4) is the formula (1).
  • An alkyl (meth) acrylate substituted with an oxygen-containing ring, represented by R 1 is a hydrogen atom or a methyl group and R 2 is an alkyl group substituted with one or more oxylan or oxetane rings, The copolymer according to any one of the preceding paragraphs.
  • (Section A13e) R 4 is an unsubstituted alkyl group having 2 to 10 carbon atoms, the copolymer according to any one of the preceding claim.
  • (Section A13f) R 4 is an unsubstituted alkyl group having 11 or more carbon atoms, the copolymer according to any one of the preceding claim.
  • R 4 is an unsubstituted alkyl group having 13 or more carbon atoms, the copolymer according to any one of the preceding claim.
  • (Section A13h) R 4 is an unsubstituted alkyl group having 18 or more carbon atoms, the copolymer according to any one of the preceding claim.
  • (Item A15a) A composition for use as a matrix in a conductive material containing a conductive component, which comprises a copolymer of a compound represented by the formula (4) according to any one of the preceding items.
  • (Item A15b) A composition for use as a matrix in a conductive material containing a conductive component, which comprises a copolymer of an alkyl (meth) acrylate substituted with the oxygen-containing group according to any one of the preceding items.
  • (Item A15c) A composition for use as a matrix in a conductive material containing a conductive component, which comprises a copolymer of an alkyl (meth) acrylate substituted with the oxygen-containing ring according to any one of the preceding items.
  • R 1 is a hydrogen atom or a methyl group and R 2 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted non-aryl heterocycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • n is an integer of 0 or 1, blend.
  • the alkyl (meth) acrylate substituted with the oxygen-containing group has the formula (1).
  • R 1 is a hydrogen atom or a methyl group and
  • R 2 is an alkyl group substituted with one to a substitutable number of substituents selected from the group consisting of alkoxy, oxylan ring and oxetane ring.
  • the second (meth) acrylic monomer has the formula (2).
  • R 3 is a hydrogen atom or a methyl group and R 4 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted non-aryl heterocycloalkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, but however, R 4 is also an alkyl group substituted with an oxygen-containing rings, nor alkyl are alkoxy-substituted, The mixture according to any one of the preceding paragraphs.
  • the alkyl (meth) acrylate substituted with the oxygen-containing ring has the formula (1).
  • R 1 is a hydrogen atom or a methyl group and R 2 is an alkyl group substituted with one or more oxylan or oxetane rings, The mixture according to any one of the preceding paragraphs.
  • R 4 is an unsubstituted alkyl group having 2 to 10 carbon atoms, the copolymer according to any one of the preceding claim.
  • (Section A17h) R 4 is an unsubstituted alkyl group having 11 or more carbon atoms, the preceding mixture according to any one of claims.
  • (Section A17i) R 4 is an unsubstituted alkyl group having 13 or more carbon atoms, the preceding mixture according to any one of claims.
  • (Section A17j) R 4 is an unsubstituted alkyl group having 18 or more carbon atoms, the preceding mixture according to any one of claims.
  • the disclosure also provides, for example:
  • a composition for lowering the firing temperature of a conductive material which comprises an alkyl (meth) acrylate substituted with an oxygen-containing ring.
  • the conductive material contains a copolymer of an alkyl (meth) acrylate substituted with the oxygen-containing ring and a conductive component.
  • the copolymer is a copolymer of an alkyl (meth) acrylate substituted with the oxygen-containing ring and a second (meth) acrylic monomer.
  • the alkyl (meth) acrylate substituted with the oxygen-containing ring is the formula (1).
  • R 1 is a hydrogen atom or a methyl group and R 2 is an alkyl group substituted with one or more oxylan or oxetane rings,
  • the composition according to any one of the above items. (Item 6)
  • the second (meth) acrylic monomer has the formula (2).
  • R 3 is a hydrogen atom or a methyl group and R 4 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted non-aryl heterocycloalkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,
  • R 4 is not an alkyl group substituted with an oxygen-containing ring, The composition according to any one of the above items.
  • (Section 6a) R 4 is an unsubstituted alkyl group having 11 or more carbon atoms, A composition according to any one of the above items.
  • R 4 is an unsubstituted alkyl group having 13 or more carbon atoms, A composition according to any one of the above items.
  • (Section 6c) R 4 is an unsubstituted alkyl group having 18 or more carbon atoms, A composition according to any one of the above items.
  • (Item 7) In any one of the above items, the alkyl (meth) acrylate substituted with the oxygen-containing ring is (3-ethyloxetane-3-yl) methyl acrylate or 2,3-epoxypropyl methacrylate. The composition described.
  • (Item 8) The composition according to any one of the above items, wherein the second (meth) acrylic monomer is isostearyl acrylate or lauryl acrylate.
  • (Item 9) A conductive material containing a copolymer of an alkyl (meth) acrylate substituted with an oxygen-containing ring and a conductive component.
  • (Item 10) The conductive material according to any one of the above items, which comprises one or more of the features described in the above item.
  • (Item 11) A method for producing a copolymer of an alkyl (meth) acrylate substituted with an oxygen-containing ring and a conductive material containing a conductive component.
  • a step of obtaining a copolymer by polymerizing an alkyl (meth) acrylate substituted with the oxygen-containing ring and a polymerizable monomer comprising the steps of mixing the copolymer and a conductive component to obtain a mixture and heating the mixture to produce a conductive material.
  • the alkyl (meth) acrylate substituted with the oxygen-containing ring has the formula (1).
  • R 1 is a hydrogen atom or a methyl group and R 2 is an alkyl group substituted with one or more oxylan or oxetane rings.
  • the second (meth) acrylic monomer has the formula (2).
  • R 3 is a hydrogen atom or a methyl group and R 4 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted non-aryl heterocycloalkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,
  • R 4 is not an alkyl group substituted with an oxygen-containing ring, Copolymer.
  • R 4 is an unsubstituted alkyl group having 11 or more carbon atoms, the copolymer according to any one of the above items.
  • (Section 13b) R 4 is an unsubstituted alkyl group having 13 or more carbon atoms, the copolymer according to any one of the above items.
  • (Section 13c) R 4 is an unsubstituted alkyl group having 18 or more carbon atoms, the copolymer according to any one of the above items.
  • Item 14 The copolymer according to any one of the above items, which comprises one or more of the characteristics described in the above item.
  • (Item 15) A composition for use as a matrix in a conductive material containing a conductive component, which comprises a copolymer of an alkyl (meth) acrylate substituted with the oxygen-containing ring according to any one of the above items.
  • (Item 16) The composition according to any one of the above items, which comprises one or more of the characteristics described in the above item.
  • (Item 17) A copolymer of an alkyl (meth) acrylate substituted with an oxygen-containing ring and a second (meth) acrylic monomer, and a mixture of metals.
  • (Item 18) The mixture according to any one of the above items, wherein the metal contains silver, copper, gold, aluminum, zinc, nickel, tin, and / or iron.
  • the alkyl (meth) acrylate substituted with the oxygen-containing ring has the formula (1).
  • R 1 is a hydrogen atom or a methyl group and R 2 is an alkyl group substituted with one or more oxylan or oxetane rings.
  • the second (meth) acrylic monomer has the formula (2).
  • R 3 is a hydrogen atom or a methyl group and R 4 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted non-aryl heterocycloalkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,
  • R 4 is not an alkyl group substituted with an oxygen-containing ring, The mixture according to any one of the above items.
  • R 4 is an unsubstituted alkyl group having 11 or more carbon atoms, mixtures of any one of the above items.
  • R 4 is an unsubstituted alkyl group having 13 or more carbon atoms, mixtures of any one of the above items.
  • a conductive material firing temperature lowering agent and a conductivity improving agent are provided, and by using these, it is possible to provide a technique capable of improving the conductivity.
  • conductivity is used in the usual sense in the art and means the property of conducting electricity, and the amount of physical properties thereof is called “conductivity”, and is used for a certain object (also called a conductor). It is defined as the reciprocal of resistivity (specific resistivity, also called volume resistivity in the resin field).
  • the conductivity is measured as follows. Specifically, unless otherwise specified, a measurement target (for example, a film) is cut out into a length of 0.5 cm, a width of 2.00 cm, and a thickness of 0.2 cm, and a four-terminal measurement method (for example, Loresta GP [Mitsubishi Chemical]. Analytech] can be used, but the value measured by is not limited to this).
  • the term "conductive material" refers to any material having conductivity.
  • the conductive material has a resistance of 1.0 ⁇ 10 -1 ⁇ ⁇ cm or less, usually 1.0 ⁇ 10 ⁇ 2 ⁇ ⁇ cm or less, preferably 1.0 ⁇ 10 -3 ⁇ ⁇ cm or less. It is intended for those with a rate, but is not limited to this.
  • the conductive material contains a conductive component that imparts conductivity.
  • the conductive material is usually composed of a base material and a conductive component.
  • the term "improving conductivity” means that when the component of the present disclosure is added to a conductive component or a conductive material, the conductivity is significantly increased as compared with the case where the component is not added.
  • the conductivity is at least about 1%, about 2%, about 3%, about 4%, about 5%, about 6%, about 7%, about 8%, about 9%, about 10%, about 15%.
  • the volume resistivity is about 1%, about 2%, about 3%, about 4%, about 5%, about 6%, about 7%, about 8%, about 9%, and about, as compared with the comparison target. 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.
  • the term "lowering the firing temperature” means the same or smaller volume when the components of the present disclosure are added to a conductive component or a conductive material and heated at a lower temperature than when not added. It means that the resistivity can be achieved.
  • the firing temperature is 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 It means to reduce by 80%, about 85%, about 90%, about 95%, and about 99%.
  • the conductive material is often heat-treated for the purpose of removing the solvent contained therein.
  • the temperature of the heat treatment is low, it is preferable because the conductive material itself and the material coated with the conductive material are less likely to be damaged.
  • the conductive component is a metal-based component described later, it is often necessary to perform a heat treatment to sinter the particles of the metal-based component in order to make the conductive material exhibit conductivity. Therefore, if the particles can be sintered with each other even if the firing temperature is lowered, it is preferable because the conductive material itself and the material coated with the conductive material are less likely to be damaged.
  • the base material is also referred to as a matrix and refers to a basic part of the structure of a conductive material.
  • Various polymers can be used as the base material.
  • the base material is a polymer
  • the base material may be referred to as a polymer matrix.
  • the "conductive component” means any component that imparts conductivity.
  • the conductive component include, but are not limited to, any metal component, a metal oxide, a metal component such as a metal carbide, a conductive carbon component, a conductive organic compound, a conductive polymer, and the like. ..
  • the "metal-based component” is a component containing a metal atom as a component thereof in some form, and in addition to a metal component such as a metal, a component derived from a metal (for example, a metal oxide, a metal carbide, etc. It is a concept that includes metal sulfide, etc.).
  • the "metal component” includes a metal or an alloy.
  • the "conductive carbon-based component” means a conductive material containing carbon.
  • Specific examples include natural graphite such as scaly graphite, graphite such as artificial graphite, acetylene black, ketjen black, channel black, furnace black, lamp black, thermal black and other carbon black, graphene, and carbon nanotubes.
  • Carbon-based materials such as graphene; carbon fibers; carbon fluoride and the like can be mentioned, but are not limited thereto.
  • Metal carbides are not included in the conductive carbon-based components.
  • the "conductive carbon-based component” may also be referred to as a "carbon-based component".
  • the "(meth) acrylic monomer” is a monomer containing an acrylic group and / or a methacrylic group, and examples thereof include acrylic acid, methacrylic acid, acrylic acid ester, methacrylic acid ester, and acrylic acid amide. Examples thereof include methacrylic acid amide.
  • (meth) acrylic means “acrylic” or “methacryl”
  • (meth) acrylate means “acrylate” or “methacrylate”.
  • the (meth) acrylic monomer also has formula (2).
  • R 3 is a hydrogen atom or a methyl group
  • R 4 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted non-aryl heterocycloalkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, but however, R 4 is also an alkyl group substituted with an oxygen-containing rings, nor alkoxy-substituted alkyl.
  • the (meth) acrylic monomer also has formula (2).
  • R 3 is a hydrogen atom or a methyl group
  • R 4 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted non-aryl heterocycloalkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group
  • R 4 is not an alkyl group substituted with an oxygen-containing ring.
  • alkyl (meth) acrylate substituted with an oxygen-containing ring is the formula (1).
  • substituted number refers to the maximum number of hydrogens that can be substituted when hydrogen on a group is substituted with a substituent, provided that the resulting group is chemically stable. means.
  • alkyl group refers to a monovalent group produced by the loss of one hydrogen atom from an aliphatic hydrocarbon (alkane) such as methane, ethane, or propane, and is generally C n H 2n + 1- . Represented (where n is a positive integer).
  • alkyl group can be straight or branched.
  • Examples of the alkyl (C 1-4 alkyl) group having 1 to 4 carbon atoms 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.
  • Examples of the alkyl (C 1 to 6 alkyl) group having 1 to 6 carbon atoms include a C 1 to 4 alkyl group, an n-pentyl group, an isoamyl group, an n-hexyl group, an isohexyl group and the like. Is not limited to such examples.
  • Examples of the alkyl (C 1 to 10 alkyl) group having 1 to 10 carbon atoms include a C 1 to 6 alkyl group, an n-octyl group, an n-nonyl group, an isononyl group, a branched nonyl group, and an n-decanyl group.
  • Examples thereof include an isodecyl group, but the present disclosure is not limited to such examples.
  • Examples of the alkyl (C 1-18 alkyl) group having 1 to 18 carbon atoms e.g., C 1 ⁇ 10 alkyl group, undecyl group, lauryl group, tridecyl group, myristyl group, pentadecyl group, palmityl group, heptadecyl group, stearyl group , Isostearyl groups and the like, but the present disclosure is not limited to such examples.
  • alkenyl group refers to a monovalent group formed by the loss of one hydrogen atom from an aliphatic hydrocarbon (alkene) containing at least one double bond such as ethene, propene, or butene. good, generally represented by C m H 2m-1 (where, m is an integer of 2 or more).
  • alkenyl group can be straight or branched. Examples of the alkenyl group having 2 to 6 carbon atoms include an ethenyl group, a 1-propenyl group, a 2-propenyl group, a butenyl group, a pentenyl group, a hexenyl group and the like, but the present disclosure is limited to such examples.
  • alkenyl group having 2 to 10 carbon atoms examples include an alkenyl group having 2 to 6 carbon atoms, a heptenyl group, an octenyl group, a nonenyl group, a decenyl group and the like, but the present disclosure is limited to such examples. It's not a thing.
  • alkoxy group refers to a monovalent group formed by the loss of the hydrogen atom of the hydroxy group of alcohols, and is generally represented by C n H 2n + 1 O- (where n is 1 or more). Is an integer of).
  • 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 and an n-. Examples thereof include a pentyloxy group, an isoamyloxy group, an n-hexyloxy group, an isohexyloxy group and the like, but the present disclosure is not limited to such examples.
  • 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 alkyl group are substituted with halogen atoms.
  • Examples of the haloalkyl group having 1 to 6 carbon atoms include a trifluoromethyl group, a trifluoroethyl group (2,2,2-trifluoroethyl group, etc.), a perfluoroethyl group, and a trifluoro group.
  • Examples of the haloalkyl group having 1 to 8 carbon atoms include a C 1-6 haloalkyl group, an undecafluoro n-heptyl group, a perfluoro n-heptyl group, and a tridecafluorooctyl group (3,3). 4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl group, etc.), perfluoron-octyl group, etc., but the present disclosure is limited to such examples. It is not limited.
  • cycloalkyl group means a monocyclic or polycyclic saturated hydrocarbon group, and includes those having a crosslinked structure.
  • C 3-12 cycloalkyl group means a cyclic alkyl group having 3 to 12 carbon atoms.
  • Specific examples of the C 6-12 cycloalkyl group include a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, an isobornyl group, a 2-methyl-2-adamantyl group, a 2-ethyl-2-adamantyl group and the like.
  • the present disclosure is not limited to such examples.
  • C 5-12 cycloalkyl group examples include a cyclopentyl group, a C 6-12 cycloalkyl group, and the like, but the present disclosure is not limited to these examples.
  • Specific examples of the C 3-12 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a C 5-12 cycloalkyl group and the like.
  • Preferably, "C 6-12 cycloalkyl group" is mentioned, but the present disclosure is not limited to such an example.
  • cycloalkenyl group means a monocyclic or polycyclic unsaturated hydrocarbon group containing a double bond, and includes those having a crosslinked structure. Examples thereof include those in which one or more of the carbon-carbon bonds of the "cycloalkyl group” are double bonds.
  • C 3-12 cycloalkenyl group means a cyclic alkenyl group having 3 to 12 carbon atoms.
  • C 6-12 cycloalkenyl group examples thereof include a 1-cyclohexenyl group, a 2-cyclohexenyl group, a 3-cyclohexenyl group, a cycloheptenyl group, a cyclooctenyl group, a cyclononenyl group and the like in the case of "C 6-12 cycloalkenyl group”. Be done.
  • C 3-12 cycloalkyl group a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, a C 6-12 cycloalkenyl group and the like can be mentioned.
  • C 6-12 cycloalkenyl group is mentioned, but the present disclosure is not limited to such an example.
  • non-aryl heterocycloalkyl and the “non-aryl heterocycle” are cyclic compounds having 1 to 3 atoms of the same type or different types selected from nitrogen atom, oxygen atom and sulfur atom in the ring. Means a group, which may contain one or more unsaturated bonds but is free of aromatic groups.
  • "3 to 8-membered non-aryl heterocycloalkyl” means a non-aryl heterocycloalkyl having 3 to 8 ring-constituting atoms.
  • non-aryl heterocycloalkyl examples include an oxylanyl group, an oxetanyl group, a pyranyl group, a pyrrolidinyl group, an imidazolidinyl group, a piperidinyl group, a morpholinyl group, a thiomorpholinyl group, a hexamethyleneiminal group, a thiazolidinyl group and a tetrahydrofuranyl group.
  • Examples thereof include a tetrahydropyridinyl group, a tetrahydropyranyl group, a 1,3-dioxolanyl group, a 1,3-dioxanyl group, a 1,4-dioxanyl group, etc., but the present disclosure is not limited to these examples. Absent.
  • the group also includes those having a crosslinked structure.
  • oxygen-containing group means a group having a carbon atom and an oxygen atom (for example, 1 to 5, 1 to 4, or 1 to 3) as constituent atoms, and the group is 1 It may contain one or more unsaturated bonds and may not contain carbon atoms, but it does not contain aromatic groups.
  • oxygen-containing group include a hydroxy group, an alkoxy group (for example, methoxy group, ethoxy group, etc.), an alkenyloxy group (for example, vinyloxy group, propenyloxy group, etc.), an oxylanyl group, an oxetanyl group, and a tetrahydrofuranyl.
  • alkenyloxyalkyl-cycloalkyl-alkyl eg 4- (vinyloxymethyl) cyclohexane-1-yl, etc.
  • oxygen-containing ring and “oxygen-containing cyclic group” mean a cyclic group having a carbon atom and 1 to 3 oxygen atoms as ring-constituting atoms, and the group may be one or more. May contain unsaturated bonds, but does not contain aromatic groups.
  • the “3 to 8-membered oxygen-containing ring” means an oxygen-containing ring having 3 to 8 ring-constituting atoms.
  • oxygen-containing ring examples include an oxylanyl group, a tetrahydrofuranyl group, an oxetanyl group, a 1,3-dioxolanyl group, a 1,3-dioxanyl group, a 1,4-dioxanyl group, and the like. It is not limited to.
  • the group also includes those having a crosslinked structure.
  • aryl group refers to a group formed by the detachment of one hydrogen atom bonded to the ring of an aromatic hydrocarbon.
  • a phenyl group from the benzene C 6 H 5 -
  • tolyl from toluene
  • xylyl from xylene
  • naphthalene naphthyl group C 10 H 8 -
  • C 6-14 aryl group means an aromatic hydrocarbon group having a carbon number of 6 to 14.
  • C 6 ⁇ 14 aryl group for example, phenyl, 1-naphthyl, 2-naphthyl group, azulenyl group, acenaphthenyl group, acenaphthyl group, an anthryl group, fluorenyl group, phenalenyl group, phenanthryl group and the like Can be mentioned.
  • C 6 ⁇ 18 aryl group for example, C 6 ⁇ 14 aryl group, a benzo [a] anthryl group, benzo [a] fluorenyl group, benzo [c] phenanthryl group, a chrysenyl group, fluoranthenyl Examples thereof include a group, a pyrenyl group, a tetrasenyl group, a triphenylenyl group and the like.
  • the arylthio group refers to an aryl-S- group.
  • a phenyl-S- group (phenylthio group) and the like can be mentioned, but the present disclosure is not limited to such an example.
  • heteroaryl group means a monocyclic or polycyclic heteroatom-containing aromatic group, which is the same or heterologous hetero selected from nitrogen, sulfur and oxygen atoms. Contains one or more atoms (eg 1 to 4).
  • heteroaryl group means a heteroaryl group having 5 to 18 ring-constituting atoms.
  • Halo heteroaryl group refers to one or more hydrogens on a ring-constituting atom substituted with halogen.
  • heteroaryl group examples include, for example, a pyrrolyl group, a thienyl group, a benzothienyl group, a benzofuranyl group, a benzoxazolyl group, a benzothiazolyl group, a frill group, an oxazolyl group, a thiazolyl group, an isooxazolyl group and an isothiazolyl group.
  • substituted refers to the replacement of one or more hydrogen radicals in a given structure by radicals of a particular substituent. It is recognized that the phrase “may be replaced” is used interchangeably with the phrase “non-replacement or replacement”.
  • C 1 ⁇ 10 alkyl optionally substituted C 6 ⁇ also be 18 aryl group group
  • unsubstituted C 6 ⁇ 18 aryl group or a C 1 ⁇ 10 C 6 ⁇ substituted with an alkyl group It is synonymous with " 18 aryl group”.
  • the number of substituents in a group defined by using “substituent” or “may be substituted” is not particularly limited as long as it can be substituted, and may be one or more. is there. Unless otherwise indicated, the description of each group also applies when the group is part of another group or a substituent.
  • 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.
  • a substituent that does not specifically specify the term "substituted” or “may be substituted” means a "unsubstituted” substituent.
  • alkyl group substituted with an oxygen-containing group refers to an alkyl group in which one hydrogen atom on the alkyl group is substituted with an oxygen-containing group, and (2) on the same carbon of the alkyl group.
  • the oxygen-containing group of the alkyl group substituted with the oxygen-containing group may be unsubstituted or substituted with a C1 to 6 alkyl group and / or a vinyloxy group.
  • the "cycloalkyl group substituted with an oxygen-containing group” is the same as the alkyl group in which one hydrogen atom on the cycloalkyl group is substituted with an oxygen-containing group, and (2) the cycloalkyl group.
  • the oxygen-containing group of the cycloalkyl group substituted with the oxygen-containing group may be unsubstituted or substituted with a C1 to 6 alkyl group and / or a vinyloxy group.
  • Examples of cycloalkyl groups substituted with oxygen-containing groups include 4- (vinyloxymethyl) cyclohexyl, 4- (hydroxymethyl) cyclohexyl and the like, but the present disclosure is not limited to such examples. Absent.
  • alkyl group substituted with an oxygen-containing ring refers to (1) an alkyl group in which one hydrogen atom on the alkyl group is substituted with an oxygen-containing ring, and (2) the same alkyl group.
  • the oxygen-containing ring of the alkyl group substituted with the oxygen-containing ring may be unsubstituted or substituted with a C 1 to 6 alkyl group.
  • alkyl groups substituted with an oxygen-containing ring examples include 2,3-epoxypropyl, (3-ethyloxetane-3-yl) methyl, tetrahydrofurfuryl, (2-ethyl-2-methyl-1,3-).
  • Examples thereof include dioxolane-4-yl) methyl, (5-ethyl-1,3-dioxane-5-yl) methyl, and the like, but the present disclosure is not limited to such examples.
  • the "polymer” means a compound formed by polymerizing a plurality of monomers.
  • the monomer is the “starting material (material)” and the polymer is the product (final product).
  • a "homopolymer” is a compound formed by polymerizing only one type of monomer
  • a “copolymer” is a compound formed by polymerizing two or more types of monomers. Is.
  • the "copolymer containing a monomer component” means a copolymer produced by polymerizing the monomer component.
  • the copolymer of monomer A means a copolymer in which one of the contained monomers is monomer A.
  • (meth) acrylate means acrylate or methacrylate, and acrylate and methacrylate may be used alone or in combination.
  • (Meta) acryloyloxy means acryloyloxy or methacryloyloxy, and acryloyloxy and methacryloyloxy may be used alone or in combination.
  • (Meta) acrylic acid means acrylic acid or methacrylic acid, and acrylic acid and methacrylic acid may be used alone or in combination.
  • (meth) acrylic polymer and “(meth) acrylic polymer” refer to homopolymers or copolymers such as (meth) acrylic acid or (meth) acrylate or salts or derivatives thereof.
  • the "monomer” means a compound obtained by polymerizing two or more of them to form a polymer.
  • the monomers of the present disclosure include (meth) acrylic monomers, ethylene-based monomers, urethane-based monomers, amide-based monomers, ester-based monomers, ether-based monomers, imide-based monomers, amide-imide-based monomers, and carbonate-based monomers.
  • Examples include 4-hydroxybutyl vinyl ether (HBVE), 2-hydroxyethyl vinyl ether (HEVE), diethylene glycol monovinyl ether (DEVGV), n-propyl vinyl ether (NPVE), isopropyl vinyl ether (IPVE), and n-butyl vinyl ether.
  • NBVE isobutyl vinyl ether
  • IBVE isobutyl vinyl ether
  • 2-EHVE 2-ethylhexyl vinyl ether
  • CHVE 1,4-cyclohexanedimethanol monovinyl ether
  • BDVE 1,4-butanediol divinyl ether
  • TEGDVE Triethylene glycol divinyl ether
  • DEGDVE diethylene glycol divinyl ether
  • CHDVE 1,4-cyclohexanedimethanol divinyl ether
  • sintering refers to a phenomenon in which raw material powder is baked and hardened at a high temperature, and although gaps are observed between the particles of the raw material powder, sintering is performed in a high temperature environment (temperature lower than the melting point). When this happens, the contact area between the particles increases, the gaps decrease, and the particles harden. The remaining gap is called a "void” or "vacancy”.
  • the "kit” usually refers to a unit in which parts to be provided (for example, coating component, conductive component, solvent, instruction manual, etc.) are provided by dividing into two or more sections.
  • the form of this kit is preferred when the purpose is to provide a composition that should not be mixed and provided for stability and the like, but is preferably mixed and used immediately before use.
  • Such a kit preferably describes how to use the provided parts (eg, conductive components, coating components) or how to treat the reagents or waste liquid after use. Or it is advantageous to have instructions.
  • the kit may usually include instructions and the like that describe how to use the solvent and the like.
  • 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 the firing temperature for obtaining the conductive material is lowered by containing the composition (also referred to as a firing temperature lowering agent) for lowering the firing temperature provided in the present disclosure. is there.
  • the conductive material of the present disclosure may typically contain other substrates of conductive components.
  • the composition (calcination temperature lowering agent) for lowering the firing temperature of the conductive material provided in the present disclosure is the formula (4). Includes compounds represented by.
  • R 1 is a hydrogen atom or a methyl group
  • R 2 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted non-aryl heterocycloalkyl group.
  • R 2 is an alkyl or cycloalkyl group that may be substituted with an oxygen-containing group.
  • R 2 is an alkyl group substituted with an oxygen-containing group.
  • R 2 is an alkyl group substituted with an oxygen-containing ring.
  • the compound represented by the formula (4) is an alkyl (meth) acrylate substituted with an oxygen-containing group.
  • the compound represented by the formula (4) is an alkyl (meth) acrylate substituted with an oxygen-containing ring.
  • n 0 and the compound represented by the formula (4) has one or two or more vinyloxy groups.
  • the composition (calcination temperature lowering agent) comprises an alkyl (meth) acrylate substituted with an oxygen-containing group. In one embodiment, the composition (calcination temperature lowering agent) also comprises an alkyl (meth) acrylate substituted with an oxygen-containing ring. In one embodiment, the composition (calcination temperature lowering agent) comprises a compound having n of 0 and represented by the formula (4). In one embodiment, the composition (calcination temperature lowering agent) comprises a compound represented by the formula (4) in which n is 0 and R 1 is a hydrogen atom.
  • an example of an alkyl (meth) acrylate substituted with an oxygen-containing ring provided in the present disclosure is of formula (1). Regardless of the type of oxygen-containing ring contained, the form of the alkyl group (carbon number, branched / linear state, etc.), methacrylic, acrylic, etc., all of them lower the firing temperature.
  • the conductive material comprises a homopolymer or copolymer of a compound represented by the formula (4) and a conductive component.
  • the conductive material comprises a homopolymer or copolymer of an alkyl (meth) acrylate substituted with the oxygen-containing group and a conductive component.
  • the conductive material comprises a homopolymer or copolymer of an alkyl (meth) acrylate substituted with the oxygen-containing ring and a conductive component.
  • the copolymer is a copolymer of a compound represented by the formula (4) and a second (meth) acrylic monomer.
  • the copolymer is a copolymer of an alkyl (meth) acrylate substituted with the oxygen-containing group and a second (meth) acrylic monomer.
  • the copolymer is a copolymer of an alkyl (meth) acrylate substituted with the oxygen-containing ring and a second (meth) acrylic monomer.
  • R 2 is an alkyl or cycloalkyl group optionally substituted with an oxygen-containing group, wherein the oxygen-containing group is a hydroxy, hydroxyalkyl, vinyloxyalkyl, alkoxy, oxylan ring or oxetane.
  • the oxygen-containing group is an alkoxy, oxylan ring or oxetane ring.
  • the oxygen-containing ring is an oxylan ring or an oxetane ring.
  • the oxygen-containing group is hydroxy or alkoxy.
  • R 2 is an alkyl group, a cycloalkyl group, or an alkylcycloalkylalkyl group that may be substituted with vinyloxy or hydroxy, or-(CH 2 CH 2 O) y- R 7 .
  • R 7 is hydrogen or vinyl, and y is an integer of 1 or more.
  • R 1 is a hydrogen atom or a methyl group and R 2 is substituted with one to a substitutable substituent selected from the group consisting of hydroxy, alkoxy, oxylan and oxetane rings. Alkoxy group.
  • the alkyl (meth) acrylate substituted with the oxygen-containing group is the formula (1).
  • R 1 is a hydrogen atom or a methyl group
  • R 2 is an alkyl group substituted with one to a substitutable number selected from the group consisting of an alkoxy, an oxylan ring and an oxetane ring. Is.
  • the alkyl (meth) acrylate substituted with the oxygen-containing ring is the formula (1).
  • R 1 is a hydrogen atom or a methyl group and R 2 is an alkyl group substituted with one or more oxylan or oxetane rings.
  • R 1 is a hydrogen atom.
  • the second (meth) acrylic monomer is of formula (2).
  • R 3 is a hydrogen atom or a methyl group and R 4 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted non-aryl heterocycloalkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, but however, R 4 is also an alkyl group substituted with an oxygen-containing rings, nor alkoxy-substituted alkyl.
  • the compound represented by formula (4) is 4-hydroxybutyl vinyl ether, 2-methoxyethyl acrylate, (3-ethyloxetane-3-yl) methyl acrylate or 2,3-epoxypropyl methacrylate. is there.
  • the alkyl (meth) acrylate substituted with the oxygen-containing group is 2-methoxyethyl acrylate, (3-ethyloxetane-3-yl) methyl acrylate or 2,3-epoxypropyl methacrylate.
  • the alkyl (meth) acrylate substituted with the oxygen-containing ring is (3-ethyloxetane-3-yl) methyl acrylate or 2,3-epoxypropyl methacrylate.
  • the compound represented by the formula (4) is 4-hydroxybutyl vinyl ether.
  • the second (meth) acrylic monomer is ethyl acrylate, stearyl acrylate, isostearyl acrylate or lauryl acrylate.
  • the compound represented by formula (4) is (3-ethyloxetane-3-yl) methyl acrylate or 2,3-epoxypropyl methacrylate, said second (meth) acrylic monomer.
  • the compound represented by formula (4) is (3-ethyloxetane-3-yl) methyl acrylate and the second (meth) acrylic monomer is isostearyl acrylate.
  • the compound represented by the formula (4) is 2,3-epoxypropyl methacrylate, and the second (meth) acrylic monomer is an isostearyl acrylate.
  • the compound represented by the formula (4) is 4-hydroxybutyl vinyl ether or 2-methoxyethyl acrylate, and the second (meth) acrylic monomer is ethyl acrylate. In one preferred embodiment, the compound represented by the formula (4) is 2-methoxyethyl acrylate, and the second (meth) acrylic monomer is ethyl acrylate. In one preferred embodiment, the compound represented by formula (4) is 4-hydroxybutyl vinyl ether and the second (meth) acrylic monomer is ethyl acrylate.
  • the basic usage of the firing temperature lowering agent is as follows.
  • the conductive material that can be targeted by the firing temperature lowering agent of the present disclosure is a material containing an arbitrary conductive component and a polymer matrix, preferably any conductive component contains a metal-based component, and more preferably any conductive component. It contains a metal component.
  • the polymer matrix of the present disclosure can be prepared by heating a monomer and / or by irradiating the monomer with ultraviolet rays of a specific illuminance to polymerize the monomer. .. Such ultraviolet irradiation can be arbitrarily set and carried out by those skilled in the art.
  • a drying operation for removing the solvent which is a complicated operation, is not required, and the workability is excellent.
  • ultraviolet rays refer to electromagnetic waves having a shorter wavelength than visible light and a longer wavelength than X-rays.
  • the short wavelength end of visible light at the upper limit is 400 nm, and ultraviolet light can be defined as an electromagnetic wave having a wavelength lower than this.
  • the lower limit of the wavelength of ultraviolet rays is about 10 nm, and it is understood that electromagnetic waves having a wavelength longer than this fall into the category of ultraviolet rays.
  • the wavelength of the ultraviolet rays used in the present disclosure may be any wavelength, and an appropriate wavelength can be selected according to the intended purpose.
  • any wavelength may be used as long as it can exert an initial effect on the monomer.
  • it is of a wavelength that can be emitted by the light source used in the examples.
  • a light source of about 150 nm to 400 nm is used, preferably 300 nm to 400 nm.
  • the preferred illuminance of ultraviolet light used in this disclosure depends on the starting material.
  • the ultraviolet irradiation device is not particularly limited, and for example, a low pressure mercury lamp, a medium pressure mercury lamp, a high pressure mercury lamp, an ultrahigh pressure mercury lamp, a metal halide lamp, a black light lamp, a UV electrodeless lamp, a short arc lamp, an LED, etc. Can be mentioned.
  • a polymerization initiator When polymerizing the monomer, it is preferable to use a polymerization initiator.
  • the polymerization initiator include a thermal polymerization initiator, a photopolymerization initiator, a redox polymerization initiator, an ATRP (atomic transfer radical polymerization) initiator, an ICAR ATRP initiator, an ARGET ATRP initiator, and a RAFT (reversible addition-cleavage).
  • ATRP atomic transfer radical polymerization
  • ICAR ATRP initiator atomic transfer radical polymerization
  • ARGET ATRP initiator an ARGET ATRP initiator
  • RAFT reversible addition-cleavage
  • Examples thereof include a 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.
  • a photopolymerization initiator is preferable from the viewpoint of not leaving a
  • photopolymerization initiator examples include 2,4,6-trimethylbenzoyldiphenylphosphenyl oxide, 2,2'-bis (o-chlorophenyl) -4,4', 5,5'-tetraphenyl-1,1'.
  • the amount of the photopolymerization initiator is usually preferably about 0.01 part by weight to about 20 parts by weight per 100 parts by weight of all the monomers.
  • thermal polymerization initiator examples include azobisisobutyronitrile (AIBN), 2,2'-azobis (methyl isobutyrate), 2,2'-azobis (2,4-dimethylvaleronitrile), 2,2.
  • Azo-based polymerization initiators such as'-azobis (2-methylbutyronitrile) and 1,1'-azobis (cyclohexane-1-carbonitrile), peroxides such as benzoyl peroxide, potassium persulfate, and ammonium persulfate. Examples thereof include a polymerization initiator, but the present disclosure is not limited to such examples. These polymerization initiators may be used alone or in combination of two or more.
  • the amount of the thermal polymerization initiator is usually preferably about 0.01 part by weight to about 20 parts by weight per 100 parts by weight of all the monomers.
  • the resulting composite material may contain air bubbles. Since such bubbles can be the starting point of fracture, it is predicted that the impact absorption capacity can be improved while the properties such as the extensibility of the composite material may be deteriorated.
  • the bubbles contained in the composite material are not limited to those derived from the polymerization initiator, and the resin or the like contains bubbles, such as those obtained by adding a foaming agent and those obtained by removing the solvent. It may be a bubble obtained by a known method capable of this.
  • redox polymerization initiators such as hydrogen peroxide and iron (II) salt, persulfate and sodium hydrogen sulfite, and ATRP using alkyl halides under a metal catalyst.
  • RAFT reversible addition-cleavage chain transfer polymerization
  • NMP nitrogen-mediated polymerization
  • Polydimethylsiloxane unit-containing polymer azo polymerization initiator polyethylene glycol unit-containing polymer azo polymerization initiator, and other polymer polymerization initiators, but the present disclosure is not limited to these examples. .. These polymerization initiators may be used alone or in combination of two or more.
  • a chain transfer agent When polymerizing the monomer, a chain transfer agent may be used to adjust the molecular weight. Chain transfer agents can usually be used by mixing with monomers. Examples of the chain transfer agent include 2- (dodecylthiocarbonothio oil thio) -2-methylpropionic acid, 2- (dodecylthiocarbonoti oil thio) propionate, and methyl 2- (dodecylthio carbonothio oil thio)-.
  • the atmosphere for polymerizing the monomer is not particularly limited and may be the atmosphere or an inert gas such as nitrogen gas or argon gas.
  • the temperature at which the monomer is polymerized 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 unconditionally determined. Therefore, it is arbitrary, but it is usually about 1 to 20 hours.
  • the polymerization reaction can be arbitrarily terminated when the amount of the remaining monomer is 20% by mass or less.
  • the amount of the remaining monomer can be measured by using, for example, gel permeation chromatography (GPC).
  • a polymer matrix can be obtained by bulk polymerization of the monomers as described above.
  • the monomer is polymerized in the absence of a cross-linking agent. In another embodiment, the monomer is polymerized in the presence of a cross-linking agent.
  • 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.
  • Examples of the method for polymerizing the monomer include a massive polymerization method, a solution polymerization method, an emulsion polymerization method, a suspension polymerization method, and the like, but the present disclosure is not limited to these examples.
  • a massive polymerization method and a solution polymerization method are preferable.
  • the polymerization of the monomer can be carried out by a method such as a radical polymerization method, a living radical polymerization method, an anion polymerization method, a cationic polymerization method, an addition polymerization method, a polycondensation method, or a catalytic polymerization method.
  • the monomer 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 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 obtained solution.
  • the solvent is preferably an organic solvent that is compatible with the monomer.
  • copolymers contained in the conductive materials of the present disclosure are polymerized by using peroxide-based initiators (eg, benzoyl peroxide and azobisisobutyronitrile, and their analogs) as polymerization initiators. You may.
  • peroxide-based initiators eg, benzoyl peroxide and azobisisobutyronitrile, and their analogs
  • the amount of the polymerization initiator is usually preferably about 0.01 part by weight to about 20 parts by weight per 100 parts by weight of all the monomers.
  • electron beam polymerization is performed by irradiating the monomer with an electron beam.
  • the monomer can be polymerized by irradiation with only an electron beam.
  • 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. Both embodiments are within the scope of the present disclosure.
  • the polymerization reaction temperature and atmosphere when polymerizing the monomer are not particularly limited. Generally, the polymerization reaction temperature is about 50 ° C. to about 120 ° C.
  • the atmosphere during the polymerization reaction is preferably an inert gas atmosphere such as nitrogen gas.
  • the polymerization reaction time of the monomer varies depending on the polymerization reaction temperature and the like and cannot be unconditionally determined, but is usually about 3 to 20 hours.
  • the polymer (or polymer matrix) contained in the conductive material of the present disclosure is required by mixing two or more specific monomers under appropriate polymerization conditions. It can be produced by polymerizing with an appropriate additive such as a polymerization initiator. Then, the conductive material of the present disclosure can be produced by mixing the conductive component and any other component with this polymer matrix and heating the polymer matrix.
  • the polymer will be described in detail below with details such as individual components and specific production conditions.
  • the present disclosure relates to equation (4). It relates to a method for producing a copolymer of a compound represented by the above and a second (meth) acrylic monomer.
  • R 1 is a hydrogen atom or a methyl group
  • R 2 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted non-aryl heterocycloalkyl group, a substituted or An unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, where n is an integer of 0 or 1.
  • the second (meth) acrylic monomer has the formula (2).
  • R 3 is a hydrogen atom or a methyl group
  • R 4 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted non-aryl heterocycloalkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, but however, R 4 is also an alkyl group substituted with an oxygen-containing rings, nor alkoxy-substituted alkyl.
  • the disclosure relates to a method of making a copolymer of an alkyl (meth) acrylate substituted with an oxygen-containing ring and a second (meth) acrylic monomer.
  • the alkyl (meth) acrylate substituted with the oxygen-containing ring has the formula (1).
  • R 1 is a hydrogen atom or a methyl group
  • R 2 is an alkyl group substituted with one or more oxylan or oxetane rings.
  • the second (meth) acrylic monomer has the formula (2).
  • R 3 is a hydrogen atom or a methyl group
  • R 4 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted non-aryl heterocycloalkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group
  • R 4 is not an alkyl group substituted with an oxygen-containing ring.
  • the polymerization of the monomer is carried out according to a polymerization method selected from the group consisting of a massive polymerization method, a solution polymerization method, an emulsion polymerization method, and a suspension polymerization method.
  • a polymerization method selected from the group consisting of a massive polymerization method, a solution polymerization method, an emulsion polymerization method, and a suspension polymerization method.
  • the monomers of the present disclosure can be polymerized by chain polymerization, step-growth polymerization, or living polymerization.
  • alkyl fluorinated (meth) acrylate and (meth) acrylic monomer used in the present disclosure may be commercially available from a manufacturer exemplified in Examples. It may be prepared according to a method well known to those skilled in the art.
  • the polymer matrix of the present disclosure is obtained in one step by exposure-polymerizing a monomer (including a plurality of types of monomers) in the presence of a polymerization initiator. ..
  • the polymer matrix of the present disclosure is prepared by irradiating one (meth) acrylic monomer and an alkyl (meth) acrylate substituted with an oxygen-containing ring with ultraviolet light in the presence of a polymerization initiator. be able to.
  • Preferred examples of the polymerization initiator 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 more.
  • the polymer matrix of the present disclosure obtained by polymerizing a monomer is dissolved in a solvent to produce a resin solution.
  • a solvent examples include heptane, octane, limonene and the like.
  • the conductive material is prepared by mixing the resin solution obtained in (3-3) with a conductive component and, if necessary, a dispersant, and the obtained mixture is used. Obtained by heating.
  • a person skilled in the art can produce a conductive material by using any method known in the art as described in the present specification and using other methods.
  • Examples of conductive components include natural graphite such as scaly graphite, graphite such as artificial graphite, acetylene black, ketjen black, channel black, furnace black, lamp black, thermal black and other carbon black, graphene, carbon nanotubes, and fullerene.
  • Carbon-based materials such as; conductive fibers such as carbon fiber and metal fiber; carbon fluoride; powder of metal particles such as copper, gold, nickel, tin, aluminum, zinc, iron and silver; zinc oxide, potassium titanate, etc.
  • Examples thereof include conductive whiskers; conductive metal oxides such as titanium oxide; organic conductive materials such as polyphenylene derivatives, but the present disclosure is not limited to these examples.
  • Each of these conductive components may be used alone, or two or more types may be used in combination.
  • these conductive components carbon nanotubes, carbon black, graphene and metal particles are preferable, and carbon nanotubes and carbon 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 solid content of the conductive component in the total solid content of the polymer matrix and the conductive component cannot be unconditionally determined because it differs depending on the type of the conductive component and the like, but it is usually excellent in workability and moldability, and also. From the viewpoint of obtaining a conductive film having excellent flexibility and extensibility, it is preferably 1% by mass or more, and from the viewpoint of obtaining a conductive film having excellent workability and moldability and excellent flexibility and extensibility. It is preferably 100% by mass or less.
  • Examples of carbon nanotubes include single-wall carbon nanotubes having a hollow cylindrical structure in which one sheet of graphite (graphene sheet) is rolled into a cylinder, and multi-walls having a structure in which a plurality of single-wall carbon nanotubes having different diameters are concentrically laminated.
  • Examples thereof include carbon nanotubes, single-wall carbon nanotubes manufactured by the super-growth method, carbon nanocones having a conical and closed end of the single-wall carbon nanotubes, and carbon nanotubes containing fullerenes inside. Is not limited to such examples.
  • Each of these carbon nanotubes may be used alone, or two or more types may be used in combination.
  • multi-wall carbon nanotubes are preferable.
  • the length of the carbon nanotubes is preferably 0.1 to 1000 ⁇ m, more preferably 1 to 500 ⁇ m, and further, from the viewpoint of obtaining a conductive film having excellent workability and moldability and excellent flexibility and extensibility. It is preferably 1 to 90 ⁇ m.
  • the diameter of the carbon nanotubes is preferably 10 to 50 nm, more preferably 10 to 20 nm, from the viewpoint of obtaining a conductive film having excellent workability and moldability, as well as excellent flexibility and extensibility.
  • the solid content of the carbon nanotubes in the total solid content of the polymer matrix and the carbon nanotubes is preferably 1% by mass from the viewpoint of obtaining a conductive film having excellent workability and moldability as well as excellent flexibility and extensibility.
  • the above is more preferably 1.5% by mass or more, still more preferably 2% by mass or more, and is preferably 25 from the viewpoint of obtaining a conductive film having excellent workability and moldability and excellent flexibility and extensibility. It is mass% or less, more preferably 20 mass% or less, further preferably 15 mass% or less, and even more preferably 3.5 to 10 mass%.
  • the conductive material of the present disclosure is suitable for, for example, sensors, wirings, electrodes, substrates, power generation elements, speakers, microphones, noise cancellers, transducers, artificial muscles, small pumps, medical instruments and the like used in actuators, industrial robots and the like. It can be suitably used as a conductive film that can be used in the above and as a raw material of the conductive film.
  • the present disclosure relates to a firing temperature lowering application.
  • the present disclosure is a composition for lowering the calcination temperature for producing a conductive material (calcination temperature lowering agent) containing an alkyl (meth) acrylate substituted with an oxygen-containing ring.
  • a composition for lowering the calcination temperature for producing a conductive material (calcination temperature lowering agent) containing an alkyl (meth) acrylate substituted with an oxygen-containing ring.
  • the calcination temperature lowering agent of the present disclosure is incorporated and used as part of a polymer matrix.
  • the conductive material of the present disclosure comprises a copolymer of an alkyl (meth) acrylate substituted with an oxygen-containing ring and a conductive component.
  • the alkyl (meth) acrylate substituted with the oxygen-containing ring can be included as a copolymer to lower the calcination temperature for producing the conductive material.
  • the copolymer used in the present disclosure is a copolymer of an alkyl (meth) acrylate substituted with an oxygen-containing group and a second (meth) acrylic monomer.
  • the copolymer used in the present disclosure is a copolymer of an alkyl (meth) acrylate substituted with an oxygen-containing ring and a second (meth) acrylic monomer.
  • the copolymers used in the present disclosure are represented by formula (4), where n is 0, R 1 is a hydrogen atom, and R 2 is an alkyl substituted with an oxygen-containing group. It is advantageous that the compound is a copolymer of a second (meth) acrylic monomer.
  • the alkyl (meth) acrylate substituted with the oxygen-containing ring is of formula (1).
  • R 1 is a hydrogen atom or a methyl group and R 2 is an alkyl group substituted with one or more oxylan or oxetane rings.
  • the second (meth) acrylic monomer is of formula (2).
  • R 3 is a hydrogen atom or a methyl group and
  • R 4 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted non-aryl heterocycloalkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,
  • R 4 is not an alkyl group substituted with an oxygen-containing ring.
  • R 4 is an unsubstituted alkyl group having 11 or more carbon atoms. In one embodiment, R 4 is an unsubstituted alkyl group having 11 to 30 carbon atoms. In one embodiment, R 4 is an unsubstituted alkyl group having 11 to 24 carbon atoms.
  • R 4 is an unsubstituted alkyl group having 13 or more carbon atoms. In one embodiment, R 4 is an unsubstituted alkyl group having 13 to 30 carbon atoms. In one embodiment, R 4 is an unsubstituted alkyl group having 13 to 24 carbon atoms.
  • R 4 is an unsubstituted alkyl group having 18 or more carbon atoms. In one embodiment, R 4 is an unsubstituted alkyl group having 18 to 30 carbon atoms. In one embodiment, R 4 is an unsubstituted alkyl group having 18 to 24 carbon atoms.
  • R 4 is an unsubstituted alkyl group having 2 to 10 carbon atoms.
  • the alkyl (meth) acrylate substituted with the oxygen-containing ring is (3-ethyloxetane-3-yl) methyl acrylate or 2,3-epoxypropyl methacrylate.
  • the second (meth) acrylic monomer is isostearyl acrylate or lauryl acrylate.
  • the present disclosure provides a conductive material with improved conductivity.
  • the present disclosure provides a conductive material comprising a copolymer of an alkyl fluorinated (meth) acrylate and a conductive component.
  • a conductive material comprising a copolymer of an alkyl fluorinated (meth) acrylate and a conductive component.
  • any embodiment described in the present specification or a combination thereof can be utilized, and any embodiment described in the section (use for improving conductivity) in the present specification. Can be applied as one or a combination of two or more.
  • the present disclosure also provides a method for producing the conductive material and the firing temperature lowering agent of the present disclosure.
  • the present disclosure provides a method for producing a copolymer of an alkyl (meth) acrylate substituted with an oxygen-containing ring and a conductive material containing a conductive component.
  • a step of obtaining a copolymer by polymerizing an alkyl (meth) acrylate substituted with the oxygen-containing ring and a polymerizable monomer a step of mixing the copolymer and a conductive component to obtain a mixture, and a step of obtaining the mixture. It includes a step of heating to produce a conductive material.
  • any embodiment described in the present specification or a combination thereof can be utilized, and any embodiment described in the section (Baking temperature lowering use) in the present specification. Can be applied as one or a combination of two or more.
  • the following conditions are typically preferable: under atmospheric pressure. 5 ° C to 100 ° C.
  • the following conditions are typically preferable: stirring by a planetary mixing stirrer at room temperature under atmospheric pressure.
  • the following conditions are typically preferable: 120 ° C. to 150 ° C. under atmospheric pressure.
  • the present disclosure is expressed in equation (4).
  • the second (meth) acrylic monomer has the formula (2).
  • R 3 is a hydrogen atom or a methyl group
  • R 4 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted non-aryl heterocycloalkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, but however, R 4 is also an alkyl group substituted with an oxygen-containing rings, nor alkyl are alkoxy-substituted, Provide copolymers. This copolymer is used, for example, as a matrix of conductive materials.
  • the alkyl (meth) acrylate substituted with the oxygen-containing group is of formula (1).
  • R 1 is a hydrogen atom or a methyl group
  • R 2 is an alkyl group substituted with one or more oxygen-containing groups.
  • equation (4) In the compound represented by, R 1 is a hydrogen atom and R 2 is an alkyl group, a cycloalkyl group, or an alkylcycloalkylalkyl group, which may be substituted with vinyloxy or hydroxy, or-(CH 2 CH). 2 O) y- R 7 , where R 7 is hydrogen or vinyl, y is an integer greater than or equal to 1, and n is 0.
  • the present disclosure also provides a copolymer of an alkyl (meth) acrylate substituted with an oxygen-containing ring and a second (meth) acrylic monomer, wherein the alkyl (meth) acrylate substituted with the oxygen-containing group is of the formula ( 1) Represented by, R 1 is a hydrogen atom or a methyl group, R 2 is an alkyl group substituted with one or more oxylan or oxetane rings.
  • the second (meth) acrylic monomer has the formula (2).
  • R 3 is a hydrogen atom or a methyl group
  • R 4 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted non-aryl heterocycloalkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group
  • R 4 is not an alkyl group substituted with an oxygen-containing ring.
  • This copolymer is used, for example, as a matrix of conductive materials.
  • R 4 is an unsubstituted alkyl group having 11 or more carbon atoms. In one embodiment, R 4 is an unsubstituted alkyl group having 11 to 30 carbon atoms. In one embodiment, R 4 is an unsubstituted alkyl group having 11 to 24 carbon atoms.
  • R 4 is an unsubstituted alkyl group having 13 or more carbon atoms. In one embodiment, R 4 is an unsubstituted alkyl group having 13 to 30 carbon atoms. In one embodiment, R 4 is an unsubstituted alkyl group having 13 to 24 carbon atoms.
  • R 4 is an unsubstituted alkyl group having 18 or more carbon atoms. In one embodiment, R 4 is an unsubstituted alkyl group having 18 to 30 carbon atoms. In one embodiment, R 4 is an unsubstituted alkyl group having 18 to 24 carbon atoms.
  • R 4 is an unsubstituted alkyl group having 2 to 10 carbon atoms.
  • the present disclosure provides matrix applications.
  • the present disclosure is a composition for use as a matrix in a conductive material containing a conductive component, comprising a copolymer of an alkyl (meth) acrylate substituted with an oxygen-containing ring represented by formula (1).
  • I will provide a.
  • the present disclosure also provides a mixture.
  • the present disclosure provides a mixture as a substance (ie, a composition comprising a copolymer and a metallic component).
  • the disclosure provides a copolymer of a compound represented by formula (4) with a (second) (meth) acrylic monomer and a mixture of metals.
  • the "second" (meth) acrylic monomer means a monomer as a companion to the compound represented by the (first) formula (4) of the copolymer.
  • the mixture is a copolymer and metal mixture of an alkyl (meth) acrylate (monomer) substituted with an oxygen-containing group and a (second) (meth) acrylic monomer.
  • R 1 is a hydrogen atom and R 2 is an alkyl group, a cycloalkyl group, or an alkylcycloalkylalkyl group, which may be substituted with vinyloxy or hydroxy, or-(. CH 2 CH 2 O) y- R 7 , where R 7 is hydrogen or vinyl, y is an integer greater than or equal to 1, and n is 0, and the compound represented by the formula (4) (second).
  • a mixture of a copolymer with a (meth) acrylic monomer and a metal is a mixture of a copolymer with a (meth) acrylic monomer and a metal.
  • the present disclosure also provides a copolymer of an alkyl (meth) acrylate (monomer) substituted with an oxygen-containing ring and a (second) (meth) acrylic monomer and a mixture of metals.
  • the "second" (meth) acrylic monomer means a monomer as a companion to the alkyl (meth) acrylate monomer substituted with the (first) oxygen-containing ring of the copolymer.
  • the metal comprises silver, copper, gold, aluminum, zinc, tin, nickel, and / or iron.
  • the metal is silver. I don't want to be bound by theory, because silver has excellent conductivity and resistance.
  • the alkyl (meth) acrylate substituted with an oxygen-containing group is of formula (1).
  • R 1 is a hydrogen atom or a methyl group
  • R 2 is alkoxy, oxirane ring and an alkyl group substituted by a substituent from one selected from the group consisting of oxetane ring to substitutable number.
  • the second (meth) acrylic monomer has the formula (2).
  • R 3 is a hydrogen atom or a methyl group
  • R 4 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted non-aryl heterocycloalkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, but however, R 4 is also an alkyl group substituted with an oxygen-containing rings, nor alkoxy-substituted alkyl.
  • the alkyl (meth) acrylate substituted with the oxygen-containing ring is of formula (1).
  • R 1 is a hydrogen atom or a methyl group
  • R 2 is an alkyl group substituted with one or more oxylan or oxetane rings.
  • the second (meth) acrylic monomer has the formula (2).
  • R 3 is a hydrogen atom or a methyl group
  • R 4 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted non-aryl heterocycloalkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group
  • R 4 is not an alkyl group substituted with an oxygen-containing ring.
  • R 4 is an unsubstituted alkyl group having 11 or more carbon atoms. In one embodiment, R 4 is an unsubstituted alkyl group having 11 to 30 carbon atoms. In one embodiment, R 4 is an unsubstituted alkyl group having 11 to 24 carbon atoms.
  • R 4 is an unsubstituted alkyl group having 13 or more carbon atoms. In one embodiment, R 4 is an unsubstituted alkyl group having 13 to 30 carbon atoms. In one embodiment, R 4 is an unsubstituted alkyl group having 13 to 24 carbon atoms.
  • R 4 is an unsubstituted alkyl group having 18 or more carbon atoms. In one embodiment, R 4 is an unsubstituted alkyl group having 18 to 30 carbon atoms. In one embodiment, R 4 is an unsubstituted alkyl group having 18 to 24 carbon atoms.
  • R 4 is an unsubstituted alkyl group having 2 to 10 carbon atoms.
  • Example 1 Preparation of polymer matrix
  • a polymer matrix was prepared.
  • Example a Isostearyl acrylate (ISTA, 9.50 g) as monomer A, (3-ethyloxetane-3-yl) methyl acrylate (4.00 g, manufactured by Osaka Organic Chemical Industry Co., Ltd., trade name OXE-10) as monomer C, and A monomer component containing a polymerization initiator was obtained by mixing 2,4,6-trimethylbenzoyldiphenylphosphine oxide (0.14 g, manufactured by BASF, trade name Irgacure (registered trademark) TPO) as a polymerization initiator. ..
  • Example b to d Comparative Example 1
  • a polymer was obtained in the same manner as in Example a except that the ratio of the monomer A and the monomer C was changed as shown in Table 1.
  • a monomer component containing a polymerization initiator was obtained by mixing 6-trimethylbenzoyldiphenylphosphine oxide (0.14 g, manufactured by BASF, trade name Irgacure (registered trademark) TPO).
  • Example 2 Preparation of conductive film
  • a conductive film was prepared.
  • the obtained 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.
  • a release polyethylene terephthalate film manufactured by Mitsui Chemicals Tohcello Co., Ltd., trade name Separator SP-PET PET-01-Bu
  • Example 3 Measurement of volume resistivity
  • the conductive film obtained in Example 2 was cut into a length of 0.5 cm and a width of 2.00 cm, and measured by a 4-terminal method using Loresta GP (manufactured by Mitsubishi Chemical Analytech).
  • Example 4 Confirmation of resistance value change
  • the change in resistance value was confirmed.
  • the conductive film obtained above was cut out to a length of 0.5 cm and a width of 2.00 cm, and before stretching with a digital multimeter [trade name PC773 manufactured by Sanwa Denki Keiki Co., Ltd.] in which the distance between electrodes was fixed at 1.00 cm.
  • the resistance value ( ⁇ A) was measured.
  • the conductive material improver of the present disclosure can be used to provide an efficient conductive material, which can be used in industries that require a conductive material.

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023074722A1 (ja) * 2021-10-27 2023-05-04 大阪有機化学工業株式会社 導電性エラストマー形成用組成物、導電性エラストマー、及び、重合体

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04170482A (ja) * 1990-11-02 1992-06-18 Kansai Paint Co Ltd 硬化性樹脂組成物
JP2004315719A (ja) * 2003-04-18 2004-11-11 Nippon Shokubai Co Ltd 焼成用樹脂組成物
JP2010250109A (ja) * 2009-04-16 2010-11-04 Fujifilm Corp ポジ型感光性組成物、並びに透明導電膜、表示素子及び集積型太陽電池
JP2011246711A (ja) * 2010-05-28 2011-12-08 Dongwoo Fine-Chem Co Ltd 粘着剤組成物およびそれを含む偏光板
WO2018235907A1 (ja) * 2017-06-23 2018-12-27 積水化学工業株式会社 樹脂組成物、無機微粒子分散スラリー組成物、無機微粒子分散シート、全固体電池の製造方法及び積層セラミクスコンデンサの製造方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4791031B2 (ja) * 2004-12-02 2011-10-12 積水化学工業株式会社 低温焼成型バインダー樹脂組成物
US9243083B2 (en) * 2008-04-03 2016-01-26 Henkel IP & Holding GmbH Thiol-ene cured oil-resistant polyacrylate sealants for in-place gasketing applications
JP6551202B2 (ja) * 2015-12-08 2019-07-31 東洋インキScホールディングス株式会社 皮膚貼付用粘着剤、経皮吸収性粘着剤、および経皮吸収性粘着シート
JP6729683B2 (ja) * 2016-04-13 2020-07-22 東亞合成株式会社 アクリルゴムの製造方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04170482A (ja) * 1990-11-02 1992-06-18 Kansai Paint Co Ltd 硬化性樹脂組成物
JP2004315719A (ja) * 2003-04-18 2004-11-11 Nippon Shokubai Co Ltd 焼成用樹脂組成物
JP2010250109A (ja) * 2009-04-16 2010-11-04 Fujifilm Corp ポジ型感光性組成物、並びに透明導電膜、表示素子及び集積型太陽電池
JP2011246711A (ja) * 2010-05-28 2011-12-08 Dongwoo Fine-Chem Co Ltd 粘着剤組成物およびそれを含む偏光板
WO2018235907A1 (ja) * 2017-06-23 2018-12-27 積水化学工業株式会社 樹脂組成物、無機微粒子分散スラリー組成物、無機微粒子分散シート、全固体電池の製造方法及び積層セラミクスコンデンサの製造方法

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023074722A1 (ja) * 2021-10-27 2023-05-04 大阪有機化学工業株式会社 導電性エラストマー形成用組成物、導電性エラストマー、及び、重合体
JPWO2023074722A1 (enrdf_load_stackoverflow) * 2021-10-27 2023-05-04
JP7719879B2 (ja) 2021-10-27 2025-08-06 大阪有機化学工業株式会社 導電性エラストマー形成用組成物、導電性エラストマー、及び、重合体

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