WO2020105333A1 - 光硬化性樹脂組成物、燃料電池用シール材およびこれらの硬化物、燃料電池ならびにシール方法 - Google Patents
光硬化性樹脂組成物、燃料電池用シール材およびこれらの硬化物、燃料電池ならびにシール方法Info
- Publication number
- WO2020105333A1 WO2020105333A1 PCT/JP2019/040981 JP2019040981W WO2020105333A1 WO 2020105333 A1 WO2020105333 A1 WO 2020105333A1 JP 2019040981 W JP2019040981 W JP 2019040981W WO 2020105333 A1 WO2020105333 A1 WO 2020105333A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- resin composition
- photocurable resin
- component
- group
- meth
- Prior art date
Links
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- HHQAGBQXOWLTLL-UHFFFAOYSA-N (2-hydroxy-3-phenoxypropyl) prop-2-enoate Chemical compound C=CC(=O)OCC(O)COC1=CC=CC=C1 HHQAGBQXOWLTLL-UHFFFAOYSA-N 0.000 claims description 3
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- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
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- PGXOVVAJURGPLL-UHFFFAOYSA-N trinaphthylene Chemical group C1=CC=C2C=C3C4=CC5=CC=CC=C5C=C4C4=CC5=CC=CC=C5C=C4C3=CC2=C1 PGXOVVAJURGPLL-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 150000003712 vitamin E derivatives Chemical class 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/06—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/10—Fuel cells with solid electrolytes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/04—Polymers provided for in subclasses C08C or C08F
- C08F290/042—Polymers of hydrocarbons as defined in group C08F10/00
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/02—Details
- H01M8/0271—Sealing or supporting means around electrodes, matrices or membranes
- H01M8/028—Sealing means characterised by their material
- H01M8/0284—Organic resins; Organic polymers
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/02—Details
- H01M8/0271—Sealing or supporting means around electrodes, matrices or membranes
- H01M8/0286—Processes for forming seals
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2003/1034—Materials or components characterised by specific properties
- C09K2003/1062—UV-curable materials
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/10—Fuel cells with solid electrolytes
- H01M2008/1095—Fuel cells with polymeric electrolytes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/10—Fuel cells with solid electrolytes
- H01M8/1004—Fuel cells with solid electrolytes characterised by membrane-electrode assemblies [MEA]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/30—Hydrogen technology
- Y02E60/50—Fuel cells
Definitions
- the present invention relates to a photocurable resin composition, a sealing material for a fuel cell, a cured product thereof, a fuel cell and a sealing method.
- a fuel cell is a power generation device that takes out electricity by chemically reacting hydrogen and oxygen. Further, the fuel cell is a clean next-generation power generation device because it has high energy efficiency during power generation and water is generated by the reaction of hydrogen and oxygen.
- fuel cells polymer electrolyte fuel cells, phosphoric acid fuel cells, molten carbonate fuel cells, and solid oxide fuel cells.
- polymer electrolyte fuel cells are Since it has a relatively low temperature (around 80 ° C.) and high power generation efficiency, it is expected to be used as a power source for automobiles, a household power generator, a small power source for electronic devices such as mobile phones, and an emergency power source.
- a cell of a general polymer electrolyte fuel cell includes an electrolyte membrane electrode assembly (MEA) having a structure in which a polymer electrolyte membrane is sandwiched between an air electrode (cathode) and a fuel electrode (anode), and It has a structure including a frame that supports the MEA and a separator in which a gas flow path is formed.
- MEA electrolyte membrane electrode assembly
- a sealant is often used for the purpose of preventing leakage of fuel gas and oxygen gas. Specifically, a sealant is used between adjacent separators, between a separator and a frame, between a frame and an electrolyte membrane or MEA, etc.
- a polyisobutylene polymer As the sealant used in the polymer electrolyte fuel cell, a polyisobutylene polymer was used because it is a rubber elastic body having excellent gas permeability resistance, low moisture permeability, heat resistance, acid resistance, and flexibility.
- Thermosetting resin composition that undergoes hydrosilylation reaction see JP-A-2004-111146
- heat-curable resin composition that undergoes hydrosilylation reaction using a fluoropolyether compound See JP-A-2004-075824.
- a heat-curable resin composition that undergoes a hydrosilylation reaction using a fluoropolymer (see Japanese Patent Application Laid-Open No.
- JP-A-2-88614 (corresponding to US Pat. No. 5,171,760) discloses a telechelic polyisobutylene polymer having two or three terminal acrylate groups, a polymer composition containing a reactive diluent. The thing is disclosed.
- an object of the present invention is to provide a photocurable resin composition which has been made in view of the above circumstances and which can be applied by screen printing and can be photocured in a short time.
- a photocurable resin composition containing the following components (A) to (D): Component (A): a polymer having one or more (meth) acryloyl groups and a polyisobutylene skeleton containing-[CH 2 C (CH 3 ) 2 ]-units, Component (B): a monofunctional monomer containing the following component (b1) and component (b2), (B1): a monofunctional monomer having a (meth) acryloyl group and a hydroxy group, (B2): a monofunctional monomer having a (meth) acryloyl group and not having a hydroxy group, Component (C): radical polymerization initiator, Component (D): Organic resin particles.
- Component (A) a polymer having one or more (meth) acryloyl groups and a polyisobutylene skeleton containing-[CH 2 C (CH 3 ) 2 ]-units
- Component (B) a monofunctional monomer
- the present invention also includes, as non-limiting examples of preferred forms, forms according to the following [2] to [17]: [2] The photocurable resin composition according to [1], wherein the component (A) is a polymer having a polyisobutylene skeleton represented by the general formula (1) described later; [3] The component (b1) is contained in an amount of 0.1 to 15 parts by mass and the component (b2) is contained in an amount of 5 to 500 parts by mass with respect to 100 parts by mass of the component (A) [1]. Alternatively, the photocurable resin composition according to [2].
- the photocurable resin composition according to any one of [1] to [3], wherein the average particle diameter of the component (D) is 0.05 to 50 ⁇ m; [5]
- the component (D) is at least one selected from the group consisting of (meth) acrylic resin particles, polystyrene particles, styrene / olefin copolymer particles, polyethylene particles and polypropylene particles.
- the photocurable resin composition according to any one of [1] to [4]; [6]
- the component (b1) is 4-hydroxybutyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxybutyl.
- the photocurable resin composition according to any one of [1] to [5], which is at least one selected from the group consisting of ethyl acid phosphate; [7]
- the component (b2) is a (meth) acrylate monomer having an alkyl group having 5 to 30 carbon atoms or an alicyclic hydrocarbon group having 5 to 30 carbon atoms and having no hydroxy group.
- a curable sealant for a fuel cell containing the photocurable resin composition according to any one of [1] to [7]; [9] The sealant for surrounding members, which is any member selected from the group consisting of a separator, a frame, an electrolyte membrane, a fuel electrode, an air electrode and an electrolyte membrane electrode assembly, which is a member in a fuel cell.
- Curable sealant for fuel cells [10] The curability for a fuel cell according to [8], which is a sealant between adjacent separators in a fuel cell or a sealant between a fuel cell frame and an electrolyte membrane or an electrolyte membrane electrode assembly.
- a fuel cell including at least one seal selected from the group consisting of a seal between adjacent separators in a fuel cell, and a seal between a frame of the fuel cell and an electrolyte membrane or an electrolyte membrane electrode assembly.
- a fuel cell, wherein at least one of the seals is the cured product according to [12];
- a method comprising: [16] A method of sealing at least a part between at least two flanges of a sealed component having at least two flanges, A step of applying the photocurable resin composition according to any one of [1] to [7] to at least one of the flanges, A step of irradiating the applied photocurable resin composition with an active energy ray to cure the photocurable resin composition, and forming a gasket made of a cured product of the photocurable resin composition, and The other flange is arranged on the gasket, and the one flange coated with the photocurable resin composition and the other flange are pressure-bonded via the gasket, and at least one between the at least two flanges.
- a method comprising: [17] A method of sealing at least a part between at least two flanges of a sealed component having at least two flanges, Disposing a gasket forming mold on at least one of the flanges, A step of injecting the photocurable resin composition according to any one of [1] to [7] into at least a part of a space between the gasket forming mold and a flange on which the mold is arranged, A step of irradiating the photocurable resin composition with an active energy ray to cure the photocurable resin composition and forming a gasket made of a cured product of the photocurable resin composition, Removing the mold from the one flange, and Disposing the other flange on the gasket, crimping the one flange and the other flange via the gasket, and sealing at least a part between the at least two flanges, A method comprising:
- FIG. 1 is a polymer electrolyte fuel cell
- 2 is a separator
- 3a is an air electrode (cathode)
- 3b is a fuel electrode (anode)
- 4 is a polymer electrolyte membrane
- 5 is an electrolyte.
- 6 is a frame
- 7 is an adhesive or sealant
- 8a is an oxidizing gas flow path
- 8b is a fuel gas flow path
- 9 is a cooling water flow path.
- 10 is a cell stack
- 11 is a polymer electrolyte fuel cell.
- the expression “to” or “from” indicating the range of the upper limit value and the lower limit value includes the upper and lower limit values themselves. That is, “X to Y” and “X to Y” indicating the ranges include X and Y and mean “more than X and less than Y”. Unless otherwise specified, operations and measurements of physical properties are performed at room temperature (20 to 25 ° C.) / Relative humidity of 40 to 50% RH.
- the acryloyl group and the methacryloyl group are collectively referred to as a (meth) acryloyl group.
- the compound having a (meth) acryloyl group is also referred to as (meth) acrylate.
- a compound containing (meth) such as (meth) acrylic acid is a generic term for a compound having “meth” in the name and a compound having no “meth”.
- One aspect of the present invention relates to a photocurable resin composition containing the following components (A) to (D).
- One aspect of the present invention provides a photocurable resin composition that can be applied by screen printing and can be photocured in a short time:
- Component (A) a polymer having one or more (meth) acryloyl groups and a polyisobutylene skeleton containing-[CH 2 C (CH 3 ) 2 ]-units
- Component (B) a monofunctional monomer containing the following component (b1) and component (b2), (B1): a monofunctional monomer having a (meth) acryloyl group and a hydroxy group, (B2): a monofunctional monomer having a (meth) acryloyl group and not having a hydroxy group
- Component (C) radical polymerization initiator
- Component (D) Organic resin particles.
- the component (A) is not particularly limited as long as it is a polymer having at least one (meth) acryloyl group and having a polyisobutylene skeleton containing-[CH 2 C (CH 3 ) 2 ]-units. ..
- the “polyisobutylene skeleton containing — [CH 2 C (CH 3 ) 2 ] -units” is also simply referred to as “polyisobutylene skeleton”.
- the component (A) has a polyisobutylene skeleton containing-[CH 2 C (CH 3 ) 2 ]-units.
- the polyisobutylene skeleton contained in the component (A) may have a-[CH 2 C (CH 3 ) 2 ] -unit, and examples thereof include a unit other than "-[CH 2 C (CH 3 ) 2 ] -unit.
- Other constituent units may be further included, such as “other constituent units”.
- the other structural unit of the polyisobutylene skeleton may be a divalent non-aromatic hydrocarbon group.
- the divalent aliphatic hydrocarbon group is a linear or branched alkylene group having 1 to 12 carbon atoms (eg, methylene group, ethylene group, n-propylene group, isopropylene group, n-butylene group, Isobutylene group, sec-butylene group, tert-butylene group, n-pentylene group, isopentylene group, sec-pentylene group, tert-pentylene group, n-hexylene group, isohexylene group, sec-hexylene group, tert-hexylene group, heptylene Group, octylene group, 2-ethylhexylene group, nonylene group, decylene group, undecylene group, dodecylene group) and the like.
- the divalent aliphatic hydrocarbon group is a linear or branched alkylene group having 1 to 12 carbon atoms (eg, methylene group,
- carbon such as methylene group, ethylene group, trimethylene group, tetramethylene group, propylene group (—CH (CH 3 ) CH 2 —), and isopropylene group (—C (CH 3 ) 2 —). It is preferably a linear or branched alkylene group of the number 1 to 6.
- the component (A) contains — [CH 2 C (CH 3 ) 2 ] -units in an amount of, for example, 70% by mass or more, preferably 75% by mass or more, based on the total amount of structural units (that is, the component (A)). , And more preferably 80% by mass or more. Further, the component (A) contains — [CH 2 C (CH 3 ) 2 ] -units in an amount of, for example, less than 100% by mass based on the total amount of structural units (that is, the component (A)). It is suitable that the content is not more than mass%, and in another embodiment, it is not more than 90 mass%. Within this range, it is possible to obtain a photocurable resin composition which is more excellent in sealing properties and can be photocured in a shorter time.
- the polyisobutylene skeleton preferably contains more than 50% by mass, more preferably 90% by mass or more, and further preferably more than 50% by mass of the — [CH 2 C (CH 3 ) 2 ] -unit with respect to the polyisobutylene skeleton. Contains 95 mass% or more. Further, the polyisobutylene skeleton contains — [CH 2 C (CH 3 ) 2 ] -units in an amount of 100% by mass or less, preferably less than 100% by mass, and less than 99.5% by mass, based on the polyisobutylene skeleton. It is more preferable to include. Within this range, it is possible to obtain a photocurable resin composition which is more excellent in sealing properties and can be photocured in a shorter time.
- the component (A) has one or more (meth) acryloyl groups.
- the number of (meth) acryloyl groups contained in the component (A) is not particularly limited as long as it is 1 or more, but is preferably 1 to 12, more preferably 2 to 8, and further preferably 2 to 4. , Particularly preferably two. Within this range, it is possible to obtain a photocurable resin composition which is more excellent in sealing properties and can be photocured in a shorter time.
- the (meth) acryloyl group may be present on either the side chain and / or the end of the molecule, but it is preferably present on the end of the molecule from the viewpoint of rubber elasticity.
- polymer refers to a compound having a structure with repeating units of a monomer in a molecule, such as a main chain, and having 100 or more repeating units, although not bound by theory. Can be defined.
- the number of repeating [-CH 2 C (CH 3 ) 2 ] -units contained in the component (A) is preferably 100 or more, more preferably 150 or more, and further preferably 180 or more. .. Further, the number of repeating [-CH 2 C (CH 3 ) 2 ] -units contained in the component (A) is preferably 500 or less, more preferably 300 or less, and more preferably 200 or less. More preferable. Within this range, it is possible to obtain a photocurable resin composition which is more excellent in sealing properties and can be photocured in a shorter time.
- the number of repeating [-CH 2 C (CH 3 ) 2 ] -units means that there are two or more-[CH 2 C (CH 3 ) 2 ] -units that are present at distant positions in the molecule. In this case, it is the sum of each — [CH 2 C (CH 3 ) 2 ] -unit.
- the component (A) is a polymer having a polyisobutylene skeleton represented by the following general formula (1), from the viewpoint of obtaining a photocurable resin composition that has excellent sealing properties and can be photocured in a short time.
- Specific examples of the component (A) include polyisobutylene having a (meth) acryloyloxyalkoxyphenyl group.
- the main skeleton of the component (A) is a polyisobutylene skeleton, and other than the main use of isobutylene as a monomer constituting the polyisobutylene skeleton, other monomers may be used as long as the effects of the present invention are not impaired. You may copolymerize.
- the other monomer is preferably a non-aromatic monomer.
- R 1 represents a monovalent or polyvalent aromatic hydrocarbon group or a monovalent or polyvalent aliphatic hydrocarbon group.
- the aromatic hydrocarbon group is not particularly limited, but includes benzene, pentalene, indene, naphthalene, anthracene, azulene, heptalene, asenaphthalene, phenalene, fluorene, anthraquinone, phenanthrene, biphenyl, terphenyl, quarterphenyl, kinkphenyl.
- the aliphatic hydrocarbon group is not particularly limited, but is a linear or branched alkyl group having 1 to 12 carbon atoms (for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group).
- R 1 is a monovalent or polyvalent group, and when the aliphatic hydrocarbon is a group having a valence of 3 or more, examples thereof include groups obtained by removing a hydrogen atom from the above-mentioned aliphatic hydrocarbon groups.
- the valency of R 1 is not particularly limited, but from the viewpoint of obtaining a photocurable resin composition which has excellent sealing properties and can be photocured in a short time, preferably 1 to 12, more preferably 2 It is -8, more preferably 2-4, and most preferably 2.
- R 1 is preferably a polyvalent aromatic hydrocarbon group, more preferably a divalent to tetravalent benzene-derived group, and particularly preferably a divalent phenylene group (o, m, p- (Phenylene group), and particularly preferably a divalent p-phenylene group.
- PIB represents a polyisobutylene skeleton containing the above-mentioned — [CH 2 C (CH 3 ) 2 ] -unit (or consisting of — [CH 2 C (CH 3 ) 2 ] -unit). ..
- PIB includes other units in addition to-[CH 2 C (CH 3 ) 2 ] -units
- other units are not particularly limited, and include, for example, methylene group, ethylene group, A straight or branched alkylene group having 1 to 6 carbon atoms such as trimethylene group, tetramethylene group, propylene group (—CH (CH 3 ) CH 2 —), isopropylene group (—C (CH 3 ) 2 —) Is mentioned.
- PIB is composed of — [CH 2 C (CH 3 ) 2 ] -units or carbon from the viewpoint of obtaining a photocurable resin composition which has excellent sealing properties and can be photocured in a short time.
- It is preferably composed of a linear or branched alkylene group having 2 to 6 carbon atoms and a-[CH 2 C (CH 3 ) 2 ] -unit, and a branched alkylene group having 3 to 5 carbon atoms and-[CH 2 C (CH 3 ) 2 ] -unit, more preferably an isopropylene group (-C (CH 3 ) 2- ) and-[CH 2 C (CH 3 ) 2 ] -unit (for example, [-C (CH 3 ) 2- [CH 2 C (CH 3 ) 2 ]-] units or [-C (CH 3 ) 2- [C (CH 3 ) 2 CH 2 ]-] units) are particularly preferred.
- R 4 represents a divalent hydrocarbon group having 2 to 6 carbon atoms which may contain an oxygen atom.
- the divalent hydrocarbon group having 2 to 6 carbon atoms is not particularly limited, and examples thereof include the same groups as the above PIB.
- R 4 is preferably a divalent hydrocarbon group having 2 or 3 carbon atoms (for example, from the viewpoint of obtaining a photocurable resin composition which has excellent sealing properties and can be photocured in a short time).
- R 4 contains an oxygen atom
- the position of the oxygen atom is not particularly limited.
- an oxygen atom is introduced into at least one terminal of the alkylene group or between adjacent carbon atoms constituting the alkylene group, or one or more hydrogen atoms constituting the alkylene group are replaced with oxygen atoms. To be done.
- R 2 and R 3 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms.
- R 2 and R 3 may be the same or different.
- the monovalent hydrocarbon group having 1 to 20 carbon atoms is not particularly limited, and examples thereof include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert.
- n-pentyl group isopentyl, neopentyl, n-hexyl group, cyclohexyl group, n-heptyl group, n-octyl group, 2-ethylhexyl group, n-nonyl group, n-decyl group, n-undecyl group , N-dodecyl group, n-tridecyl group, n-tetradecyl group, 2-tetraoctyl group, n-pentadecyl group, n-hexadecyl group, 2-hexyldecyl group, n-heptadecyl group, 1-octylnonyl group, n Examples thereof include straight-chain or branched-chain alkyl groups such as -octadecyl group, n-nonadecyl group, and n
- R 2 and R 3 are preferably hydrogen atoms, straight-chain having 1 to 8 carbon atoms, or from the viewpoint of obtaining a photocurable resin composition that has excellent sealing properties and can be photocured in a short time.
- a branched chain alkyl group more preferably a hydrogen atom, a linear or branched chain alkyl group having 1 to 3 carbon atoms, and particularly preferably a hydrogen atom.
- R 5 represents a hydrogen atom, a methyl group or an ethyl group.
- a hydrogen atom or a methyl group is preferable, and a hydrogen atom is more preferable, from the viewpoint of obtaining a photocurable resin composition that has excellent sealing properties and can be photocured in a short time.
- n represents an integer of 1 to 6.
- an integer of 2 to 4 is preferable, and 2 is more preferable.
- the component (A) is preferably liquid at room temperature (25 ° C.), because a photocurable resin composition that can better cope with application by screen printing can be obtained.
- the molecular weight of the component (A) is not particularly limited, but the number average molecular weight measured by chromatography is preferably 200 to 500,000 from the viewpoint that it can be applied by screen printing and has excellent sealing properties. It is more preferably 1,000 to 100,000, and even more preferably 3,000 to 50,000.
- the number average molecular weight can be calculated by a standard polystyrene conversion method using size permeation chromatography (SEC).
- the viscosity of the component (A) at 25 ° C. is not particularly limited, but from the viewpoint of workability and the like, it is preferably 5 Pa ⁇ s or more, more preferably 50 Pa ⁇ s or more, and further preferably 100 Pa ⁇ s or more. Is.
- the viscosity of the component (A) at 25 ° C. is not particularly limited, but from the same viewpoint, it is preferably 3000 Pa ⁇ s or less, more preferably 2500 Pa ⁇ s or less, and further preferably 2000 Pa ⁇ s. It is below.
- a particularly preferable viscosity is 1550 Pa ⁇ s or less. Unless otherwise specified, the viscosity is a value measured at 25 ° C. using a cone-plate type viscometer.
- the component (A) may be used alone or in combination of two or more kinds.
- the method for producing the component (A) is not particularly limited, and known methods can be used. For example, Polymer Bulletin, Volume 6, pp. 135-141 (1981), T.W. P. Liao and J. P. Kennedy, and Polymer Bulletin, Volume 20, pp. 253-260 (1988), Puskas et al. And a method obtained by reacting a terminal hydroxyl group polyisobutylene with acryloyl chloride or methacryloyl chloride.
- a method obtained by reacting a terminal hydroxyl group polyisobutylene with a compound having a (meth) acryloyl group and an isocyanate group, a terminal hydroxyl group polyisobutylene and an isocyanate group are included.
- the method for producing the polymer having the polyisobutylene skeleton represented by the general formula (1) is not particularly limited, and a known method can be used.
- a method of reacting a halogen-terminated polyisobutylene disclosed in JP-A-2013-216782 with a compound having a (meth) acryloyl group and a phenoxy group represented by the following general formula (2) is used.
- the halogen-terminated polyisobutylene can be obtained by a known method, but is preferably obtained by cationic polymerization, more preferably living cationic polymerization.
- R 2, R 3 , R 4 , and R 5 may be as defined in the above formula (1).
- R 4 represents a divalent hydrocarbon group having 2 to 6 carbon atoms and optionally containing an oxygen atom.
- R 2 and R 3 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms.
- R 5 represents a hydrogen atom, a methyl group or an ethyl group.
- the compound represented by the general formula (2) is not particularly limited, but examples thereof include phenoxymethyl (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxypropyl (meth) acrylate, phenoxybutyl (meth) acrylate, and phenoxy. Pentyl (meth) acrylate etc. are mentioned. Among these, phenoxyethyl (meth) acrylate, phenoxypropyl (meth) acrylate, phenoxybutyl (meth) acrylate, phenoxypentyl (meth) acrylate and the like are preferable.
- the component (B) contained in the photocurable resin composition according to one aspect of the present invention is a monofunctional monomer having a (meth) acryloyl group which is a component (b1) and a hydroxy group, and a component (b2). Which is a monofunctional monomer having a (meth) acryloyl group and having no hydroxy group.
- a photocurable resin composition which can be applied by screen printing and can be photocured in a short time by combining the component (b1), the component (b2) and the other component according to one embodiment of the present invention. can do. Further, by combining (b1) and (b2), the effect of suppressing the crystallization of the photocurable resin composition is further exhibited.
- the crystallization of the photocurable resin composition means the precipitation of crystals during storage and storage after the production of the photocurable resin composition.
- a group existing as a group having a hydroxyl group (—OH group) attached to a hydrocarbon, that is, an —OH group bonded to a hydrocarbon group is particularly preferable.
- the component (b1) is not particularly limited, and examples thereof include hydroxybutyl (meth) acrylate (eg, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, etc.), hydroxypropyl (meth) acrylate ( For example, 3-hydroxypropyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, etc., hydroxyethyl (meth) acrylate (eg, 2-hydroxyethyl (meth) acrylate, etc.), 2-hydroxy-3-phenoxypropyl Examples thereof include acrylate, 2-acryloyloxyethyl-2-hydroxyethyl-phthalic acid, 2- (meth) acryloyloxyethyl acid phosphate, and 2- (meth) acryloyloxyethyl acid phosphate.
- hydroxybutyl (meth) acrylate eg, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (
- the component (b1) includes 4-hydroxybutyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, and 2-hydroxybutyl (meth) acrylate.
- ) Acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-acryloyloxyethyl-2-hydroxyethyl-phthalic acid, 2- (meth) acryloyloxyethyl acid phosphate and 2- (meth) acryloyloxyethyl acid It is preferably at least one selected from the group consisting of phosphates.
- 4-hydroxybutyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate and 2-hydroxyethyl (meth) acrylate are more preferable.
- a synthetic product or a commercially available product may be used as the component (b1).
- the commercially available product is not particularly limited, but for example, HOA (N), HOP-A (N), HOB-A, HOB, P-1M, P-1A, G-201P, M-600A (Kyoeisha Chemical Co., Ltd. ), 4HBA, HPA, HEA (manufactured by Osaka Organic Chemical Industry Co., Ltd.) and the like.
- the component (b1) can be used alone or as a mixture of two or more kinds.
- a (meth) acrylate monomer having an alkyl group having 5 to 30 carbon atoms and not having a hydroxy group also referred to as a hydroxyl group in the present specification
- examples include (meth) acrylate monomers having a formula hydrocarbon group but not a hydroxyl group. That is, examples thereof include (meth) acrylate monomers having an alkyl group having 5 to 30 carbon atoms or an alicyclic hydrocarbon group having 5 to 30 carbon atoms and having no hydroxy group.
- a (meth) acrylate monomer having an alicyclic hydrocarbon group having 5 to 30 carbon atoms and having no hydroxyl group is preferable.
- the carbon number is preferably 5 or more, and more preferably 7 or more.
- the carbon number is preferably 30 or less, more preferably 20 or less, more preferably 15 or less, and further preferably 10 or less.
- the (meth) acrylate monomer having an alkyl group having 5 to 30 carbon atoms (that is, the (meth) acrylate monomer having an alkyl group having 5 to 30 carbon atoms and having no hydroxyl group) is not particularly limited.
- Is for example, 2-ethylhexyl (meth) acrylate, octyl (meth) acrylate, isooctyl (meth) acrylate, decyl (meth) acrylate, dodecyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, n- Examples thereof include octadecyl (meth) acrylate, isooctadecyl (meth) acrylate, nonadecane (meth) acrylate, isostearyl (meth) acrylate, stearyl (meth) acrylate and the like.
- 2-ethylhexyl (meth) acrylate, isooctyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, isooctadecyl (meth) acrylate, isostearyl (meth) acrylate, stearyl (meth) acrylate, etc. is preferred.
- the (meth) acrylate monomer having an alkyl group having 5 to 30 carbon atoms and not having a hydroxyl group a synthetic product or a commercially available product may be used.
- the commercially available product is not particularly limited, and examples thereof include SR335, SR395, SR440, SR489D, SR313, SR324, SR493D (manufactured by Sartomer Co.), S-1800A (manufactured by Shin-Nakamura Chemical Co., Ltd.).
- the above-mentioned (meth) acrylate monomer having an alicyclic hydrocarbon group having 5 to 30 carbon atoms that is, a (meth) acrylate having an alicyclic hydrocarbon group having 5 to 30 carbon atoms and having no hydroxyl group
- the monomer is not particularly limited, and examples thereof include cyclohexyl (meth) acrylate, trimethylcyclohexyl (meth) acrylate, t-butylcyclohexyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate.
- Dicyclopentenyloxy (meth) acrylate Dicyclopentenyloxy (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, dicyclopentenyl di (meth) acrylate and the like.
- trimethylcyclohexyl (meth) acrylate, t-butylcyclohexyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentenyloxy (meth) acrylate, isobornyl (meth) Acrylate and the like are preferred.
- the (meth) acrylate monomer having an alicyclic hydrocarbon group having 5 to 30 carbon atoms and not having a hydroxyl group a synthetic product or a commercially available product may be used.
- the commercially available product is not particularly limited, and examples thereof include SR506, SR423 (Sartomer), IBX, IBX-A (Kyoeisha Chemical Co., Ltd.), FA-511AS, FA-512AS, FA-513AS, FA-512M, FA-. 512 MT, FA-513M (Hitachi Chemical Co., Ltd.) and the like.
- the component (b2) can be used alone or as a mixture of two or more kinds.
- the molecular weights of the component (b1) and the component (b2) are not particularly limited, but each is preferably less than 1000, more preferably 500 or less, and further preferably 300 or less.
- the molecular weights of the component (b1) and the component (b2) can be determined as the sum of the atomic weights of the atoms constituting them.
- the amount of the component (B) is preferably 0.1 to 15 parts by mass of the component (b1) and 5 to 500 parts by mass of the component (b2) per 100 parts by mass of the component (A). More preferably, the component (b1) is contained in an amount of 0.3 to 12 parts by mass, the component (b2) is contained in an amount of 10 to 300 parts by mass, the component (b1) is contained in an amount of 0.5 to 10 parts by mass, and the component (b2) is contained. It is more preferable to include 12 to 200 parts by mass. Within the above range, it is possible to provide a photocurable resin composition that can better cope with application by screen printing and can be photocured in a short time.
- the amount of the component (b1) is preferably 0.5 to 10 parts by mass with respect to 100 parts by mass of the component (A), The range is more preferably 1.1 to 5.0 parts by mass, and further preferably 1.3 to 4.0 parts by mass.
- the photoradical polymerization initiator of the component (C) contained in the photocurable resin composition according to one aspect of the present invention is not particularly limited as long as it is a compound that generates a radical upon irradiation with an active energy ray.
- the active energy rays include radiation such as ⁇ rays and ⁇ rays, electromagnetic waves such as ⁇ rays and X rays, electron rays, ultraviolet rays having a wavelength of about 100 to 400 nm, visible light having a wavelength of about 400 to 800 nm, and the like. It is a concept that includes all light in a broad sense. Among these, ultraviolet rays are preferable.
- the component (C) is not particularly limited, and examples thereof include an acetophenone-based photoradical polymerization initiator, a benzoin-based photoradical polymerization initiator, a benzophenone-based photoradical polymerization initiator, a thioxanthone-based photoradical polymerization initiator, and an acylphosphine oxide-based component. Examples thereof include a photo radical polymerization initiator and a titanocene-based photo radical polymerization initiator.
- an acetophenone-based photoradical polymerization initiator and an acylphosphine oxide-based photoradical polymerization initiator are The acylphosphine oxide-based photoradical polymerization initiator is more preferable.
- the acetophenone-based photoradical polymerization initiator is not particularly limited, and examples thereof include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, benzyldimethylketal, 4- (2-hydroxyethoxy).
- a synthetic or commercially available acetophenone-based photoradical polymerization initiator may be used.
- the commercially available product is not particularly limited, and examples thereof include IRGACURE (registered trademark) 184, IRGACUR (registered trademark) 1173, IRGACURE (registered trademark) 2959, IRGACURE (registered trademark) 127 (manufactured by BASF), and ESACURE (registered trademark).
- Examples include KIP-150 (manufactured by Lamberti spa).
- the acylphosphine oxide-based photoradical polymerization initiator is not particularly limited, and examples thereof include bis (2,4,6-trimethylbenzoyl) -phenyl-phosphine oxide and 2,4,6-trimethylbenzoyl-diphenyl-phosphine. Examples thereof include oxide.
- acylphosphine oxide-based photoradical polymerization initiator a synthetic product or a commercially available product may be used.
- commercially available products include, but are not limited to, Omnirad (registered trademark) TPO, Omnirad (registered trademark) 819 (manufactured by IGM Resins BV), IRGACURE (registered trademark) 819DW (manufactured by BASF), and the like. Be done.
- the component (C) may be used alone or in combination of two or more kinds.
- the blending amount of the component (C) is not particularly limited, but is preferably 0.1 to 20 parts by mass, more preferably 0.5 to 10 parts by mass, relative to 100 parts by mass of the component (A). And more preferably 1.1 to 5 parts by mass. Within the above range, it is possible to provide a photocurable resin composition that can better cope with application by screen printing and can be photocured in a short time. From the viewpoint that crystallization of the photocurable resin composition can be suppressed, it is preferable that the content of the component (C) is 0.1 to 10 parts by mass with respect to 100 parts by mass of the component (A). It is preferably in the range of 0.5 to 5.0 parts by mass, and more preferably in the range of 0.7 to 4.0 parts by mass.
- the component (D) contained in the photocurable resin composition according to one aspect of the present invention is not particularly limited as long as it is organic resin particles.
- the effect of eliminating bubbles generated during screen printing of the photocurable resin composition is exhibited. Further, it becomes possible to further suppress the phase separation of the photocurable resin composition.
- the component (D) is not particularly limited, but examples thereof include (meth) acrylic resin particles, polystyrene particles, styrene / olefin copolymer particles, polyethylene particles, and polypropylene particles. Therefore, the component (D) is preferably at least one selected from the group consisting of (meth) acrylic resin particles, polystyrene particles, styrene / olefin copolymer particles, polyethylene particles, and polypropylene particles. ..
- (meth) acrylic resin particles, polystyrene particles, styrene / olefin copolymer particles and the like are preferable, and (meth) acrylic resin particles and styrene / olefin copolymer particles are more preferable.
- the styrene / olefin copolymer particles are those in which a styrene monomer and another crosslinkable substance are copolymerized to form a polymer.
- the styrene monomer and the divinylbenzene are copolymerized with each other. Examples thereof include a polymer, a copolymer of styrene monomer and polybutadiene, and a copolymer of styrene monomer and isoprene.
- a synthetic product or a commercially available product may be used as the component (D).
- Commercially available products of the (meth) acrylic resin particles are not particularly limited, and examples thereof include MBX-5, MBX-8, MBX-12, SSX-101, SSX-102, SSX-103, SSX-104, SSX-105. , SSX-108, (manufactured by Sekisui Plastics Co., Ltd.), MR-1HG, MR-2G, MR-5C, MX-300, MX-150, MX-500, MZ-5HN (manufactured by Soken Chemical Industry Co., Ltd.), etc. Is mentioned.
- polystyrene particles and styrene / olefin copolymer particles are not particularly limited, and examples thereof include SBX-4, SBX-6, SBX-8 (manufactured by Sekisui Plastics Co., Ltd.), KSR-3A, Examples thereof include SX-130H, SX-350H, SX-500H (manufactured by Soken Kagaku Co., Ltd.).
- the average particle size of the component (D) is not particularly limited, but is preferably 0.05 to 50 ⁇ m, more preferably 0.1 to 40 ⁇ m, and further preferably 0.3 to 25 ⁇ m. Within the above range, it is possible to better cope with screen printing.
- the average particle size is a particle size (D50) at a cumulative volume ratio of 50% in a particle size distribution obtained by a laser diffraction scattering method.
- the shape of the component (D) is not particularly limited, but a spherical shape is preferable from the viewpoint of preventing clogging during screen printing.
- the component (D) may be used alone or in combination of two or more kinds.
- the blending amount of the component (D) is not particularly limited, but is preferably 0.001 to 20 parts by mass, more preferably 0.005 to 10 parts by mass, relative to 100 parts by mass of the component (A). Yes, and more preferably 0.01 to 5 parts by mass. Within the above range, it is possible to provide a photocurable resin composition that can better cope with application by screen printing and can be photocured in a short time.
- an oligomer or polymer having a (meth) acryloyl group (excluding the above component (A)) and an inorganic filler, within a range that does not impair the object of the present invention.
- Additives such as materials, organic peroxides, curing accelerators, storage stabilizers, antioxidants, light stabilizers, plasticizers, pigments, flame retardants, and surfactants can be used.
- the oligomer or polymer having a (meth) acryloyl group (not including the above component (A)) is not particularly limited, but examples thereof include urethane (meth) acrylate having a polybutadiene skeleton and urethane (meth) acrylate having a hydrogenated polybutadiene skeleton.
- Urethane (meth) acrylate of polycarbonate skeleton Urethane (meth) acrylate of polycarbonate skeleton, urethane (meth) acrylate of polyether skeleton, urethane (meth) acrylate of polyester skeleton, urethane (meth) acrylate of castor oil skeleton, isoprene-based (meth) acrylate, hydrogenated isoprene-based ( Examples thereof include (meth) acrylate, epoxy (meth) acrylate, and (meth) acrylic group-containing acrylic polymer.
- the urethane (meth) acrylate of the polybutadiene skeleton, the urethane (meth) acrylate of the hydrogenated polybutadiene skeleton, and the castor oil skeleton of the component (A) and the component (B) are excellent in compatibility.
- Urethane (meth) acrylate, isoprene-based (meth) acrylate, and hydrogenated isoprene-based (meth) acrylate are preferable.
- oligomer refers to a compound having a structure having a repeating unit of a monomer in a molecule, such as a main chain, and having 2 or more and less than 100 repeating units, although not bound by theory. Can be defined.
- the oligomer or polymer having a (meth) acryloyl group may be used alone or in combination of two or more kinds.
- An inorganic filler may be added to the photocurable resin composition according to one aspect of the present invention to the extent that it does not impair storage stability for the purpose of improving the elastic modulus and fluidity of the cured product.
- Specific examples include inorganic powder and metallic powder.
- the filler of the inorganic powder is not particularly limited, but for example, glass, fumed silica, alumina, mica, ceramics, silicone rubber powder, calcium carbonate, aluminum nitride, carbon powder, kaolin clay, dry clay mineral, dried Examples include diatomaceous earth.
- the blending amount of the inorganic powder is not particularly limited, but is preferably about 0.1 to 100 parts by mass with respect to 100 parts by mass of the component (A).
- Fumed silica can be blended for the purpose of adjusting the viscosity of the photocurable resin composition or improving the mechanical strength of the cured product.
- those subjected to a hydrophobic treatment with organochlorosilanes, polyorganosiloxane, hexamethyldisilazane and the like can be used.
- Specific examples of the fumed silica include commercially available products such as Aerosil (registered trademark) R974, R972, R972V, R972CF, R805, R812, R812S, R816, R8200, RY200, RX200, RY200S, and R202 manufactured by Nippon Aerosil Co., Ltd. Goods are listed.
- An organic peroxide may be added to the photocurable resin composition according to one aspect of the present invention for the purpose of imparting curability by heating or a redox reaction.
- the redox reaction is preferable because radical species can be generated at room temperature.
- the organic peroxide is not particularly limited, and examples thereof include methyl ethyl ketone peroxide, cyclohexanone peroxide, 3,3,5-trimethylcyclohexanone peroxide, methyl cyclohexanone peroxide, methyl acetoacetate peroxide, and acetylacetone peroxide.
- Ketone peroxides such as oxides; 1,1-bis (t-butylperoxy) -3,3,5-trimethylcyclohexane, 1,1-bis (t-butylperoxy) cyclohexane, 2,2-bis (t-butylperoxy) Peroxyketals such as (oxy) octane, n-butyl-4,4-bis (t-butylperoxy) valerate and 2,2-bis (t-butylperoxy) butane; t-butyl hydroperoxide, cumene Hydroperoxide, diisopropylbenzene hydroperoxide, p-menthane hydroperoxide, 2,5-dimethylhexane-2,5-dihydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, etc.
- Peroxides di-t-butyl peroxide, t-butylcumyl peroxide, dicumyl peroxide, ⁇ , ⁇ '-bis (t-butylperoxy-m-isopropyl) benzene, 2,5-dimethyl-2, Dialkyl peroxides such as 5-di (t-butylperoxy) hexane and 2,5-dimethyl-2,5-di (t-butylperoxy) hexyne-3; acetyl peroxide, isobutyryl peroxide, octa Noyl peroxide, decanoyl peroxide, lauroyl peroxide, 3,5,5-trimethylhexanoyl peroxide, succinic acid peroxide, benzoyl peroxide, 2,4-dichlorobenzoyl peroxide, m-toluoyl peroxide Diacyl peroxides such as diisopropyl peroxy
- a curing accelerator can be added for the purpose of promoting the redox reaction.
- the curing accelerator is not particularly limited, but preferably saccharin (o-benzoxulfimide), a hydrazine compound, an amine compound, a mercaptan compound, a transition metal-containing compound or the like is used.
- the hydrazine compound is not particularly limited, but for example, 1-acetyl-2-phenylhydrazine, 1-acetyl-2 (p-tolyl) hydrazine, 1-benzoyl-2-phenylhydrazine, 1- (1 ′, 1 ′ , 1′-Trifluoro) acetyl-2-phenylhydrazine, 1,5-diphenyl-carbohydrazine, 1-formyl-2-phenylhydrazine, 1-acetyl-2- (p-bromophenyl) hydrazine, 1-acetyl- 2- (p-nitrophenyl) hydrazine, 1-acetyl-2- (2'-phenylethylhydrazine), ethylcarbazate, p-nitrophenylhydrazine, p-trisulfonylhydrazide and the like can be mentioned.
- the amine compound is not particularly limited, and examples thereof include heterocyclic secondary amines such as 2-ethylhexylamine, 1,2,3,4-tetrahydroquinone, 1,2,3,4-tetrahydroquinaldine; quinoline, Heterocyclic tertiary amines such as methylquinoline, quinaldine, quinoxalinephenazine; aromatic tertiary amines such as N, N-dimethyl-para-toluidine, N, N-dimethyl-anisidine, N, N-dimethylaniline; 1 , 2,4-triazole, oxazole, oxadiazole, thiadiazole, benzotriazole, hydroxybenzotriazole, benzoxazole, 1,2,3-benzothiadiazole, 3-mercaptobenzotrizole, and other azole compounds. ..
- the mercaptan compound is not particularly limited, and examples thereof include n-dodecyl mercaptan, ethyl mercaptan, butyl mercaptan, tris-[(3-mercaptopropionyloxy) -ethyl] -isocyanurate, pentaerythritol tetrakis (3-mercaptopropionate). ), Dipentaerythritol hexakis (3-mercaptopropionate), trimethylolpropane tris (3-mercaptopropionate), trimethylolpropane tristhioglycolate, pentaerythritol tetrakisthioglycolate and the like.
- the transition metal-containing compound is not particularly limited, but a metal chelate complex salt is preferably used.
- a metal chelate complex salt examples thereof include iron pentadione, pentadione cobalt, pentadione copper, propylenediamine copper, ethylenediamine copper, iron naphthate, nickel naphthate, cobalt naphthate, copper naphthate, copper octate, iron hexoate, iron propionate, and acetylacetone vanadium.
- the curing accelerator may be used alone or in combination of two or more.
- a mixture of saccharin, a hydrazine-based compound, an amine-based compound and a transition metal-containing compound is more preferable because it has a good curing acceleration effect.
- a storage stabilizer may be added to the photocurable resin composition according to one aspect of the present invention.
- the storage stabilizer is not particularly limited, but examples thereof include radical absorbers such as benzoquinone, hydroquinone and hydroquinone monomethyl ether, ethylenediamine tetraacetic acid or its 2-sodium salt, metal chelates such as oxalic acid, acetylacetone and o-aminophenol. Agents and the like can be added.
- An antioxidant may be added to the photocurable resin composition according to one aspect of the present invention.
- the antioxidant is not particularly limited, and examples thereof include ⁇ -naphthoquinone, 2-methoxy-1,4-naphthoquinone, methylhydroquinone, hydroquinone, hydroquinone monomethyl ether, mono-tert-butylhydroquinone, 2,5-di-tert.
- a light stabilizer may be added to the photocurable resin composition according to one aspect of the present invention.
- the light stabilizer is not particularly limited, and examples thereof include bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis (1,2,2,6,6-pentamethyl-4-piperidyl) Sebacate, 4-benzoyloxy-2,2,6,6-tetramethylpiperidine, 1- [2- [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionyloxy] ethyl] -4 -[3- (3,5-Di-tert-butyl-4-hydroxyphenyl) propionyloxy] -2,2,6,6-tetramethylpiperidine, 1,2,2,6,6-pentamethyl-4- Piperidinyl-methacrylate, bis (1,2,2,6,6-pentamethyl-4-piperidinyl) [[3,5-bis (1,1-dimethylethyl) -4-hydroxy
- adhesion promoter may be added to the photocurable resin composition according to one aspect of the present invention.
- the adhesion-imparting agent is not particularly limited, and examples thereof include 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-acryloxypropyltrimethoxysilane, methacryloxyoctyltrimethoxysilane, vinyltrimethoxysilane, vinyltrichlorosilane, vinyltriethoxysilane, vinyl-tris ( ⁇ -methoxyethoxy) silane, ⁇ -chloropropyltrimethoxysilane, ⁇ -(3,4-Epoxycyclohexyl) ethyltrimethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -mer
- hydroxyethyl methacrylate phosphate, methacryloxyoxyethyl acid phosphate, methacryloxyoxyethyl acid phosphate monoethylamine half salt, 2-hydroxyethyl methacrylic acid phosphate and the like are preferable.
- the content of the adhesion promoter is not particularly limited, but is preferably 0.05 to 30 parts by mass, and more preferably 0.2 to 10 parts by mass with respect to 100 parts by mass of the component (A).
- the method for producing the photocurable resin composition according to one aspect of the present invention is not particularly limited and can be produced by a conventionally known method. For example, mixing predetermined amounts of the components (A) to (D) and using a mixing means such as a mixer, preferably at a temperature of 10 to 70 ° C., preferably for 0.1 to 5 hours. Can be manufactured by. Further, the photocurable resin composition according to one aspect of the present invention is preferably manufactured in a light-shielding environment.
- the method of applying the photocurable resin composition according to one aspect of the present invention to an adherend is not particularly limited.
- methods such as dispensing using an automatic coating machine, spraying, inkjet, screen printing, gravure printing, dipping, and spin coating can be used.
- the photocurable resin composition according to one embodiment of the present invention is most suitable for screen printing because it exhibits the effect of eliminating bubbles generated during screen printing.
- the photocurable resin composition according to one aspect of the present invention is preferably liquid at 25 ° C from the viewpoint of coatability.
- the light source for curing the photocurable resin composition according to one embodiment of the present invention by irradiating active energy rays is not particularly limited, and a known light source is used.
- active energy rays for example, light such as ultraviolet rays and visible light
- low-pressure mercury lamp, medium-pressure mercury lamp, high-pressure mercury lamp, ultra-high-pressure mercury lamp, black light lamp, microwave-excited mercury lamp, metal halide lamp, sodium lamp, halogen lamp, xenon lamp, LED, fluorescent lamp, sunlight, electron beam irradiation device, etc. Is mentioned.
- the dose of irradiation is characteristic aspect from 3 kJ / m 2 or more of the cured product, and more preferably 5 kJ / m 2 or more.
- From the viewpoint of the cycle time of the curing step is preferably at 50 kJ / m 2 or less, and more preferably not more than 25 kJ / m 2, still more preferably 15 kJ / m 2 or less.
- ⁇ Cured product> Another aspect of the present invention relates to the above photocurable resin composition or a cured product of a curable sealant for a fuel cell according to another aspect of the present invention described later.
- the cured product according to one aspect of the present invention if the photocurable resin composition is a curable sealant for a fuel cell according to another aspect of the present invention which will be described later or is cured, the curing method thereof. It doesn't matter.
- the cured product according to one aspect of the present invention is the photocurable resin composition described above, or the curable sealant for a fuel cell according to another aspect of the present invention described below, by the above curing method. It is preferably cured by irradiation with active energy rays such as ultraviolet rays. From this, the form is a cured product obtained by irradiating the above photocurable resin composition or a curable sealant for a fuel cell according to another aspect of the present invention described below with light. Is preferred.
- a curable sealant is mentioned as an application for which the photocurable resin composition according to one aspect of the present invention or its cured product is preferably used.
- the term “sealant” also includes applications such as an adhesive, a coating agent, a casting agent, and a potting agent.
- the said photocurable resin composition is a liquid at 25 degreeC.
- the above-mentioned photocurable resin composition or a cured product thereof has low gas permeability (particularly low hydrogen permeability), low moisture permeability, heat resistance, acid resistance, and flexibility. Since it is an excellent rubber elastic body, it is used for fuel cells, solar cells, dye-sensitized solar cells, lithium-ion batteries, electrolytic capacitors, liquid crystal displays, organic EL displays, electronic paper, LEDs, hard disk devices, photodiodes, optical communications. -Layers such as circuits, electric wires / cables / optical fibers, optical isolators, IC cards, sensors, substrates, medical / medical instruments / equipment, etc.
- the photocurable resin composition described above is rapidly cured by irradiation with active energy rays such as ultraviolet rays, and is excellent in gas barrier properties, so that fuel cell applications, particularly solid polymer fuel cell applications Particularly preferred. Therefore, another embodiment of the present invention relates to a curable sealant for fuel cells, which contains the above photocurable resin composition.
- a curable sealant for polymer electrolyte fuel cells containing the above-mentioned photocurable resin composition can be mentioned.
- the curable sealant for a fuel cell according to one embodiment of the present invention is any member selected from the group consisting of a separator in a fuel cell, a frame, an electrolyte membrane, a fuel electrode, an air electrode and an electrolyte membrane electrode assembly. It is preferably a sealant for a member periphery. That is, the curable sealant for a fuel cell according to one aspect of the present invention is preferably a cured product thereof used for sealing the periphery of these members. Further, a curable sealant for a fuel cell according to one aspect of the present invention is a sealant between adjacent separators in a fuel cell, or a frame of the fuel cell, an electrolyte membrane or an electrolyte membrane electrode assembly (MEA).
- MEA electrolyte membrane or an electrolyte membrane electrode assembly
- the cured product is used for sealing between the adjacent separators in the fuel cell according to the one aspect of the present invention, or the fuel cell. More preferably, it is used for sealing between the frame and the electrolyte membrane, or more preferably used for sealing between the frame of the fuel cell and the electrolyte membrane electrode assembly (MEA).
- MEA electrolyte membrane electrode assembly
- the fuel cell preferably polymer electrolyte fuel cell
- the curable sealant for a fuel cell according to one embodiment of the present invention is applied is not particularly limited.
- the curable sealant for a fuel cell according to one aspect of the present invention is applied to the fuel cell as described above. Moreover, another aspect of the present invention relates to a fuel cell.
- a fuel cell is a power generator that generates electricity by chemically reacting hydrogen and oxygen.
- fuel cells there are mainly four types of fuel cells: solid polymer fuel cells, phosphoric acid fuel cells, molten carbonate fuel cells, and solid oxide fuel cells.
- the polymer electrolyte fuel cell has a high power generation efficiency while operating at a relatively low temperature (around 80 ° C.), so that it can be used for power sources for automobiles, household power generators, electronic devices such as mobile phones. It is preferably used for applications such as small power supplies and emergency power supplies.
- FIG. 1 is a schematic cross-sectional view of a single cell as an example of a fuel cell.
- FIG. 2 is a schematic diagram showing an entire example of a fuel cell.
- a polymer electrolyte membrane 4 is sandwiched between an air electrode (cathode electrode) 3a and a fuel electrode (anode electrode) 3b.
- This is a structure including an electrolyte membrane electrode assembly 5 (MEA) that is a structure, a frame 6 that supports the MEA, and a separator 2 in which a gas flow path is formed.
- MEA electrolyte membrane electrode assembly 5
- the fuel gas (hydrogen gas) and the oxidizing gas (oxygen gas) are supplied through the oxidizing gas passage 8a and the fuel gas passage 8b. Further, the cooling water flows through the flow path 9 for the purpose of relaxing heat generation during power generation. Note that a stack of several hundred cells is packaged as a cell stack 10 as shown in FIG.
- the polymer electrolyte fuel cell 11 has a cell stack 10.
- a sealant is often used for the purpose of preventing leakage of fuel gas, oxygen gas and the like. Specifically, a sealant is used between adjacent separators, between a separator and a frame, between a frame and an electrolyte membrane or MEA, etc. This corresponds to the case where at least one of the adhesive or the seal material 7 in FIG. 1 is a seal material.
- the fuel cell according to one embodiment of the present invention is a group consisting of a seal between adjacent separators in the fuel cell, and a seal between the fuel cell frame and the electrolyte membrane or the electrolyte membrane electrode assembly. It is preferable that at least one of the seals is selected from the above, and at least one of the seals is a cured product of the above photocurable resin composition or the above curable sealant for fuel cells. .. Further, the fuel cell is more preferably a polymer electrolyte fuel cell.
- Examples of the above-mentioned polymer electrolyte membrane include a cation exchange membrane having ionic conductivity, which is preferably chemically stable and is resistant to operation at high temperatures, and therefore it is a fluoropolymer having a sulfonic acid group. And so on.
- Examples of commercially available products include Nafion (registered trademark) manufactured by DuPont, Flemion (registered trademark) manufactured by AGC Corporation, and Aciplex (registered trademark) manufactured by Asahi Kasei Corporation.
- the polymer electrolyte membrane is a material that is difficult to adhere to, but it can be adhered by using the above photocurable resin composition or the above curable sealant for fuel cells.
- the fuel electrode is called a hydrogen electrode or an anode, and known ones are used.
- carbon supported by a catalyst such as platinum, nickel or ruthenium is used.
- the air electrode is called an oxygen electrode or a cathode, and known ones are used.
- carbon supported by a catalyst such as platinum or alloy is used.
- the surface of each electrode may be provided with a gas diffusion layer that functions to diffuse gas and moisturize the electrolyte.
- a known gas diffusion layer is used. Examples include carbon paper, carbon cloth, and carbon fiber.
- the separator 2 has a fine flow path with unevenness, through which fuel gas or oxidizing gas passes and is supplied to the electrodes.
- the separator is made of aluminum, stainless steel, titanium, graphite, carbon, or the like.
- the frame is to support and reinforce the thin electrolyte membrane or MEA so that it will not break.
- the material of the frame include thermoplastic resins such as polyvinyl chloride, polyethylene naphthalate, polyethylene terephthalate, polypropylene and polycarbonate. Further, in order to bond members using the above-mentioned photocurable resin composition, curable sealant for fuel cells, or these cured products, it is preferable that the members transmit light.
- the fuel cell according to one aspect of the present invention is a fuel cell characterized by being sealed with the above-mentioned photocurable resin composition, a curable sealant for a fuel cell, or a cured product thereof.
- the member that needs to be sealed in the fuel cell include a separator, a frame, an electrolyte membrane, a fuel electrode, an air electrode, and MEA. More specific sealing points include between adjacent separators, between separator and frame, between frame and electrolyte membrane or MEA (between frame and electrolyte membrane or between frame and MEA), etc. Is mentioned.
- the main purpose of the seal "between the separator and the frame” or “between the polymer electrolyte membrane or MEA and the frame” is to prevent mixing and leakage of gas, and to prevent a gap between the adjacent separators.
- the purpose of the seal is to prevent gas from leaking and to prevent cooling water from leaking from the cooling water flow path to the outside.
- a preferable sealant is required to have acid resistance.
- ⁇ Seal method> Another aspect of the present invention relates to a sealing method using the above photocurable resin composition (or the above curable sealant for a fuel cell).
- the sealing method using the above photocurable resin composition is not particularly limited, but typically, FIPG (foam in place gasket), CIPG (cure in place gasket), MIPG (mold in place gasket), Liquid injection molding and the like can be mentioned.
- FIPG is a flange that can transmit active energy rays such as ultraviolet rays in a state where the above-mentioned photocurable resin composition is applied to the flange of the sealed part by an automatic application device or the like and is bonded to the other flange.
- This is a method of irradiating from the side to cure the photocurable resin composition and then performing adhesive sealing. More specifically, it is a method for sealing at least a part between at least two flanges of a sealed component having at least two flanges, wherein at least one of the flanges is capable of transmitting light of active energy rays.
- At least one surface of the flange, the step of applying the photocurable resin composition described above, one flange coated with the photocurable resin composition and the other flange the photocurable resin composition A step of bonding through, and a step of irradiating an active energy ray through the light transmissive flange to cure the photocurable resin composition, and sealing at least a part between the at least two flanges,
- the method is characterized by including.
- a preferred example is a method for sealing at least a part between at least one set of two flanges to be bonded in a sealed component having at least two flanges, and at least the two flanges to be bonded.
- One is permeable to active energy rays, and a step of applying the photocurable resin composition described above on one surface of the two flanges to be bonded together, and after applying the photocurable resin composition, A step of attaching one of the two flanges to be attached and the other flange via the photocurable resin composition, and transmitting the active energy ray of the two flanges to be attached Irradiating the active energy ray through a possible flange to cure the photocurable resin composition and seal at least a part between the two flanges to be bonded together. There is a method of doing.
- CIPG is a photocurable resin composition obtained by bead-coating the above-mentioned photocurable resin composition onto a flange of a sealed part by a screen printing coating device, an automatic coating device, or the like, and irradiating with active energy rays such as ultraviolet rays. Is cured to form a gasket, which is then attached to the other flange and compression-sealed. More specifically, it is a method of sealing at least a part between at least two flanges of a sealed component having at least two flanges, wherein at least one of the flanges has the above-mentioned photocurable resin.
- the step of arranging, the other flange is disposed on the gasket, and the one flange coated with the photocurable resin composition and the other flange are pressure-bonded via the gasket, and between the at least two flanges.
- a step of sealing at least a part thereof is a method for sealing at least a part between at least one pair of two flanges to be bonded in a sealed component having at least two flanges, one of the two flanges to be bonded.
- the step of applying the photocurable resin composition described above to the flange of, and irradiating the photocurable resin composition after application with an active energy ray to cure the photocurable resin composition A step of forming a gasket composed of a cured product of a curable resin composition, and arranging the other flange of the two flanges to be bonded together on the gasket, and arranging the gasket of the two flanges to be bonded together. And pressing the other flange disposed on the gasket through the gasket to seal at least a part between the two flanges to be bonded together.
- a characteristic method is mentioned.
- MIPG is a mold in which the flange of the component to be sealed is pressed in advance, and the above-mentioned photocurable resin composition is injected into the cavity formed between the mold and the flange of a light-transmissive material to activate UV rays or the like.
- This is a method of irradiating with energy rays, photo-curing to form a gasket, and then adhering it to the other flange to perform compression sealing.
- the mold is preferably made of a light-transmitting material, and specific examples thereof include glass, polymethylmethacrylate (PMMA), polycarbonate, cycloolefin polymer, olefin and the like.
- a release agent such as a fluorine type or silicone type to the mold in advance. More specifically, it is a method for sealing at least a part between at least two flanges of a sealed component having at least two flanges, wherein a gasket forming mold is provided on at least one of the flanges.
- Arranging step injecting the photocurable resin composition described above into at least a part of the gap between the gasket forming mold and the flange on which the mold is arranged, active in the photocurable resin composition
- a preferable example is a method for sealing at least a part between at least one pair of two flanges to be bonded in a sealed component having at least two flanges, one of the two flanges to be bonded.
- a step of removing the gasket forming mold from a flange on which the gasket forming mold is arranged, the other flange of the two flanges to be bonded is arranged on the gasket, One of the two flanges of the two flanges to be bonded, in which the gasket is arranged, and the other flange arranged on the gasket, are crimped via the gasket, and at least a part between the at least two flanges is pressed. And a step of sealing.
- the above photocurable resin composition is poured into a mold of a material which is light transmissive by a specific pressure, irradiated with active energy rays such as ultraviolet rays, and photocured to form a gasket, and This is a method in which it is attached to the other flange and compression-sealed.
- the mold is preferably made of a material that can transmit light, and specific examples thereof include glass, PMMA, polycarbonate, cycloolefin polymer, and olefin.
- a release agent such as a fluorine type or silicone type to the mold in advance.
- the supernatant is separated from the reaction solution, the solvent and the like are distilled off, the product is dissolved in 3000 ml of n-hexane, washed with 3000 ml of pure water three times, and reprecipitated from methanol, and then the solvent is depressurized.
- the polymer was distilled off under reduced pressure, and the obtained polymer was vacuum dried at 80 ° C. for 24 hours to obtain polyisobutylene (a1) having an acryloyloxyethoxyphenyl group.
- the number average molecular weight of (a1) (chromatography method, polystyrene conversion) was 11,100, and the viscosity (25 ° C.) of (a1) was 1,550 Pa ⁇ s.
- ⁇ Preparation of photocurable resin composition> -Example 1 100 parts by mass of polyisobutylene (a1) having an acryloyloxyethoxyphenyl group obtained in Synthesis Example 1 as the component (A) of the present invention; 3 parts by mass of 4-hydroxybutyl acrylate (4HBA, manufactured by Osaka Organic Chemical Industry Co., Ltd.) as the component (b1-1) of the component (B), and isobornyl methacrylate (SR423, manufactured by Sartomer) 50 as the component (b2).
- HBA 4-hydroxybutyl acrylate
- SR423, manufactured by Sartomer isobornyl methacrylate
- Example 2 The photocurable resin composition of Example 2 was prepared in the same manner as in Example 1 except that the amount of 4-hydroxybutyl acrylate as the component (b1-1) added was 6 parts by mass. Got The photocurable resin composition was liquid at 25 ° C.
- Example 1 was repeated except that hydroxypropyl acrylate (HPA, manufactured by Osaka Organic Chemical Industry Co., Ltd.) was used as the component (b1-2) instead of 4-hydroxybutyl acrylate as the component (b1-1).
- HPA hydroxypropyl acrylate
- the photocurable resin composition was liquid at 25 ° C.
- Example 1 was repeated except that hydroxyethyl acrylate (HEA, manufactured by Osaka Organic Chemical Industry Co., Ltd.) was used as the component (b1-3) instead of 4-hydroxybutyl acrylate as the component (b1-1) in Example 1.
- HSA hydroxyethyl acrylate
- Example 4 Example 1 was repeated except that hydroxyethyl acrylate (HEA, manufactured by Osaka Organic Chemical Industry Co., Ltd.) was used as the component (b1-3) instead of 4-hydroxybutyl acrylate as the component (b1-1) in Example 1.
- HSA hydroxyethyl acrylate
- Example 5 In Example 1, styrene / olefin copolymer particles (SBX-6, manufactured by Sekisui Plastics Co., Ltd.) having an average particle size of 6 ⁇ m were used as the component (D) instead of the acrylic resin particles having an average particle size of 1 ⁇ m. Other than that were prepared like Example 1 and the photocurable resin composition of Example 5 was obtained.
- the photocurable resin composition was liquid at 25 ° C.
- Comparative example 1 A photocurable resin composition of Comparative Example 1 was obtained in the same manner as in Example 1, except that the component (b1-1), 4-hydroxybutyl acrylate, was omitted.
- Example 1 was prepared in the same manner as in Example 1 except that the component (b2) was removed and 4-hydroxybutyl acrylate as the component (b1-1) was changed from 3 parts by weight to 53 parts by weight, A photocurable resin composition of Comparative Example 3 was obtained.
- the photocurable resin composition of Comparative Example 3 was separated immediately after production. Therefore, it was difficult to evaluate the characteristics.
- test methods used in the examples and comparative examples in Table 1 below are as follows.
- Test A Each photocurable resin composition was printed and applied on a polytetrafluoroethylene sheet by a screen printing machine in a 25 ° C. environment using a SUS mesh screen printing plate having openings of about 110 ⁇ m. After 10 seconds, it was visually confirmed whether bubbles disappeared from the printed layer (thickness 50 ⁇ m) of the photocurable resin composition.
- the present invention can provide a photocurable resin composition that can be applied by screen printing and can be photocured in a short time of 3.5 seconds.
- Comparative Example 1 in Table 1 is a photocurable resin composition in which the component (b1-1) of the component (B) of the present invention is not contained, but it has screen printability and photocuring in a short time. Both were inferior results.
- Comparative Example 2 was a composition in which metal particles were used instead of the component (D) of the present invention, but the result was that the screen printability was poor.
- Example 1 Water vapor transmission rate (water vapor barrier property)
- the photocurable resin composition of Example 1 was poured into a frame of 200 mm ⁇ 200 mm ⁇ 1.0 mm. After that, ultraviolet rays were radiated for 20 seconds by an ultraviolet irradiator so that the integrated light amount became 45 kJ / m 2, and a sheet-shaped cured product having a thickness of 1.0 mm was produced. 5 g of calcium chloride (anhydrous) was placed in an aluminum cup having an opening with a diameter of 30 mm, and the cured product was set in the cup.
- calcium chloride anhydrous
- the moisture permeability is preferably less than 10 g / m 2 ⁇ 24 h when used as a curable sealant for fuel cells.
- Example 1 Hydrogen gas barrier property test The photocurable resin composition of Example 1 was irradiated with ultraviolet rays for 20 seconds by an ultraviolet irradiation device so that the integrated light amount was 45 kJ / m 2, and a sheet-like sheet having a thickness of 1.0 mm was obtained. A cured product was produced. Then, the sheet-like cured product was used to measure the hydrogen gas permeability in accordance with JIS K7126-1: 2006 (Plastic-Film and Sheet-Gas Permeability Test Method-Part 1: Differential Pressure Method).
- the type of test was a pressure sensor method, the conditions were 23 ° C., the test gas (hydrogen gas) on the high pressure side was 100 kPa, and the evaluation was made based on the following evaluation criteria.
- the results of this implementation are shown in Table 2 below.
- the hydrogen gas barrier property is preferably less than 1 ⁇ 10 ⁇ 15 mol ⁇ m / m 2 ⁇ s ⁇ Pa when used as a photocurable sealant for a fuel cell.
- Example 1 in Table 2 it is understood that the present invention has a low moisture permeability, an excellent hydrogen barrier property, and a good sealing property.
- the present invention has been made in view of the above situation, and since it is a photocurable resin composition that can be applied by screen printing and can be photocured in a short time, it can be used for various sealing applications. In particular, it is industrially useful because it is effective as a curable sealant for fuel cells.
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Abstract
Description
[1]下記の(A)~(D)成分を含有することを特徴とする光硬化性樹脂組成物:
(A)成分:1以上の(メタ)アクリロイル基と、-[CH2C(CH3)2]-単位を含むポリイソブチレン骨格とを有するポリマー、
(B)成分:下記の(b1)成分と、(b2)成分とを含む単官能性モノマー、
(b1):(メタ)アクリロイル基と、ヒドロキシ基とを有する単官能性モノマー、
(b2):(メタ)アクリロイル基を有し、ヒドロキシ基を有さない単官能性モノマー、
(C)成分:ラジカル重合開始剤、
(D)成分:有機樹脂粒子。
[2]前記(A)成分が、後述する一般式(1)で表されるポリイソブチレン骨格を有するポリマーである、[1]に記載の光硬化性樹脂組成物;
[3]前記(A)成分100質量部に対して、前記(b1)成分を0.1~15質量部含み、前記(b2)成分を5~500質量部含むことを特徴とする[1]または[2]に記載の光硬化性樹脂組成物;
[4]前記(D)成分の平均粒径が0.05~50μmであることを特徴とする[1」~[3]のいずれか1項に記載の光硬化性樹脂組成物;
[5]前記(D)成分が、(メタ)アクリル樹脂粒子、ポリスチレン粒子、スチレン・オレフィン共重合体粒子、ポリエチレン粒子およびポリプロピレン粒子からなる群より選択される少なくとも1種であることを特徴とする[1]~[4]のいずれか1項に記載の光硬化性樹脂組成物;
[6]前記(b1)成分が、4ーヒドロキシブチル(メタ)アクリレート、3ーヒドロキシプロピル(メタ)アクリレート、2ーヒドロキシプロピル(メタ)アクリレート、2ーヒドロキシエチル(メタ)アクリレート、2-ヒドロキシブチル(メタ)アクリレート、2-ヒドロキシ-3-フェノキシプロピルアクリレート、2-アクリロイロキシエチル-2-ヒドロキシエチル-フタル酸、2-(メタ)アクリロイロキシエチルアシッドホスフェートおよび2-(メタ)アクリロイロキシエチルアシッドホスフェートからなる群より選択される少なくとも1種であることを特徴とする[1]~[5]のいずれか1項に記載の光硬化性樹脂組成物;
[7]前記(b2)成分が、炭素数5~30のアルキル基または炭素数5~30の脂環式炭化水素基を有し、かつ、ヒドロキシ基を有さない(メタ)アクリレートモノマーであることを特徴とする[1]~[6]のいずれか1項に記載の光硬化性樹脂組成物;
[8][1]~[7]のいずれか1項に記載の光硬化性樹脂組成物を含む、燃料電池用硬化性シール剤;
[9]燃料電池における部材であるセパレーター、フレーム、電解質膜、燃料極、空気極および電解質膜電極接合体からなる群より選択されるいずれかの部材周辺用シール剤である、[8]に記載の燃料電池用硬化性シール剤;
[10]燃料電池における隣り合うセパレーター同士の間のシール剤、または燃料電池のフレームと電解質膜もしくは電解質膜電極接合体との間のシール剤である、[8]に記載の燃料電池用硬化性シール剤;
[11]固体高分子形燃料電池用シール剤である、[8]~[10]のいずれか1項に記載の燃料電池用硬化性シール剤;
[12][1]~[7]のいずれか1項に記載の光硬化性樹脂組成物、または[8]~[11]のいずれか1項に記載の燃料電池用硬化性シール剤に対して光照射することにより得られる硬化物。
[14]固体高分子形燃料電池である、[13]に記載の燃料電池;
[15]少なくとも2つのフランジを有する被シール部品の当該少なくとも2つのフランジの間の少なくとも一部をシールする方法であって、
前記フランジの少なくとも一方が活性エネルギー線の光を透過可能であり、前記フランジの少なくとも一方の表面に、[1]~[7]のいずれか1項に記載の光硬化性樹脂組成物を塗布する工程、
前記光硬化性樹脂組成物を塗布した一方のフランジと他方のフランジとを前記光硬化性樹脂組成物を介して貼り合わせる工程、および、
活性エネルギー線を前記光透過可能なフランジを通して照射して前記光硬化性樹脂組成物を硬化させ、前記少なくとも2つのフランジの間の少なくとも一部をシールする工程、
を含むことを特徴とする、方法;
[16]少なくとも2つのフランジを有する被シール部品の当該少なくとも2つのフランジの間の少なくとも一部をシールする方法であって、
前記フランジの少なくとも一方のフランジに、[1]~[7]のいずれか1項に記載の光硬化性樹脂組成物を塗布する工程、
前記塗布した光硬化性樹脂組成物に活性エネルギー線を照射して前記光硬化性樹脂組成物を硬化させ、前記光硬化性樹脂組成物の硬化物からなるガスケットを形成する工程、および、
他方のフランジを前記ガスケット上に配置して、前記光硬化性樹脂組成物を塗布した一方のフランジと前記他方のフランジとを前記ガスケットを介して圧着し、前記少なくとも2つのフランジの間の少なくとも一部をシールする工程、
を含むことを特徴とする、方法;
[17]少なくとも2つのフランジを有する被シール部品の当該少なくとも2つのフランジの間の少なくとも一部をシールする方法であって、
前記フランジの少なくとも一方のフランジ上にガスケット形成用金型を配置する工程、
前記ガスケット形成用金型と該金型を配置したフランジとの間の空隙の少なくとも一部に[1]~[7]のいずれか1項に記載の光硬化性樹脂組成物を注入する工程、
前記光硬化性樹脂組成物に活性エネルギー線を照射して前記光硬化性樹脂組成物を硬化させ、前記光硬化性樹脂組成物の硬化物からなるガスケットを形成する工程、
前記金型を前記一方のフランジから取り外す工程、および、
他方のフランジを前記ガスケット上に配置して、前記一方のフランジと前記他方のフランジとを前記ガスケットを介して圧着し、前記少なくとも2つのフランジの間の少なくとも一部をシールする工程、
を含むことを特徴とする、方法。
(A)成分:1以上の(メタ)アクリロイル基と、-[CH2C(CH3)2]-単位を含むポリイソブチレン骨格とを有するポリマー、
(B)成分:下記の(b1)成分と、(b2)成分とを含む単官能性モノマー、
(b1):(メタ)アクリロイル基と、ヒドロキシ基とを有する単官能性モノマー、
(b2):(メタ)アクリロイル基を有し、ヒドロキシ基を有さない単官能性モノマー、
(C)成分:ラジカル重合開始剤、
(D)成分:有機樹脂粒子。
本発明の一形態に係る光硬化性樹脂組成物に含まれる(A)成分は、1以上の(メタ)アクリロイル基(CH2=CH-C(=O)-またはCH2=C(CH3)-C(=O)-)と、-[CH2C(CH3)2]-単位を含むポリイソブチレン骨格とを有するポリマーである。(A)成分は、(メタ)アクリロイル基を1以上有し、かつ、-[CH2C(CH3)2]-単位を含むポリイソブチレン骨格を有するポリマーであれば特に限定されるものではない。なお、本明細書において、「-[CH2C(CH3)2]-単位を含むポリイソブチレン骨格」を、単に「ポリイソブチレン骨格」とも称する。
本発明の一形態に係る光硬化性樹脂組成物に含まれる(B)成分は、(b1)成分である(メタ)アクリロイル基と、ヒドロキシ基とを有する単官能性モノマーと、(b2)成分である(メタ)アクリロイル基を有し、ヒドロキシ基を有さない単官能性モノマーとを含む、単官能性モノマーである。
本発明の一形態に係る光硬化性樹脂組成物に含まれる(C)成分の光ラジカル重合開始剤は、活性エネルギー線を照射することにより、ラジカルが発生する化合物であれば、特に制限されない。ここで、活性エネルギー線とは、α線やβ線等の放射線、γ線やX線等の電磁波、電子線、波長が100~400nm程度の紫外線、波長が400~800nm程度の可視光線等の広義の光全てを含む概念である。これらの中でも、紫外線が好ましい。
本発明の一形態に係る光硬化性樹脂組成物に含まれる(D)成分は、有機樹脂粒子であれば特に制限されない。(D)成分と、本願発明の一形態に係るその他の成分と組み合わせることによって、光硬化性樹脂組成物のスクリーン印刷時に発生した気泡を消泡させるという効果が発揮される。また、光硬化性樹脂組成物の相分離を抑制することがさらに可能となる。
本発明の一形態に係る光硬化性樹脂組成物に対し、本発明の目的を損なわない範囲で、(メタ)アクリロイル基を有するオリゴマーまたはポリマー(上記の(A)成分を含まない)、無機充填材、有機過酸化物、硬化促進剤、保存安定剤、酸化防止剤、光安定剤、可塑剤、顔料、難燃剤、および界面活性剤等の添加剤を使用することができる。
本発明の一形態に係る光硬化性樹脂組成物を被着体への塗布する方法としては、特に制限されない。例えば、自動塗布機を用いたディスペンシング、スプレー、インクジェット、スクリーン印刷、グラビア印刷、ディッピング、スピンコートなどの方法を用いることができる。これらの中でも、本発明の一形態に係る光硬化性樹脂組成物は、スクリーン印刷時に発生した気泡を消泡させるという効果を発揮することから、スクリーン印刷に最適である。なお、本発明の一形態に係る光硬化性樹脂組成物は、塗布性の観点から、25℃で液状であることが好ましい。
本発明の一形態に係る光硬化性樹脂組成物を、活性エネルギー線(例えば、紫外線、可視光等の光)を照射することにより硬化させるに際しての光源は、特に限定されず、公知の光源を用いることができる。例えば、低圧水銀灯、中圧水銀灯、高圧水銀灯、超高圧水銀灯、ブラックライトランプ、マイクロウェーブ励起水銀灯、メタルハライドランプ、ナトリウムランプ、ハロゲンランプ、キセノンランプ、LED、蛍光灯、太陽光、電子線照射装置等が挙げられる。光照射の照射量は硬化物の特性の観点から3kJ/m2以上であることが好ましく、より好ましくは5kJ/m2以上である。また、硬化工程のタクトタイムの観点から、50kJ/m2以下であることが好ましく、より好ましくは25kJ/m2以下であり、さらに好ましくは15kJ/m2以下である。
本発明の他の一形態は、上記の光硬化性樹脂組成物、または後述する本発明のその他の一形態に係る燃料電池用硬化性シール剤の硬化物に関する。本発明の一形態に係る硬化物は、上記の光硬化性樹脂組成物がまたは後述する本発明のその他の一形態に係る燃料電池用硬化性シール剤硬化したものであれば、その硬化方法の如何は問わない。ここで、本発明の一形態に係る硬化物は、上記の光硬化性樹脂組成物、または後述する本発明のその他の一形態に係る燃料電池用硬化性シール剤に対し、上記の硬化方法によって紫外線等の活性エネルギー線を照射することにより硬化させてなることが好ましい。これより、当該形態は、上記の光硬化性樹脂組成物、または後述する本発明のその他の一形態に係る燃料電池用硬化性シール剤に対して光照射することにより得られる硬化物であることが好ましい。
本発明の一形態に係る光硬化性樹脂組成物またはその硬化物が好適に用いられる用途としては、硬化性シール剤が挙げられる。本明細書において、シール剤とは、接着剤、コーティング剤、注型剤、ポッティング剤等の用途も含まれるものである。なお、このような用途で使用するにあたり、上記の光硬化性樹脂組成物は、25℃で液状であることが好ましい。
本発明の一形態に係る燃料電池用硬化性シール剤は、前述のように燃料電池に適用される。また、本発明の他の一形態は、燃料電池に関する。
本発明の他の一形態は、上記の光硬化性樹脂組成物(または上記の燃料電池用硬化性シール剤)を用いたシール方法に関する。
・合成例1:アクリロイルオキシエトキシフェニル基を有するポリイソブチレン(a1)の製造
5Lのセパラブルフラスコの容器内を窒素置換した後、n-ヘキサン200mL及び塩化ブチル2000mLを加え、窒素雰囲気下で攪拌しながら-70℃まで冷却した。次いで、イソブチレン840mL(9mol)、p-ジクミルクロライド12g(0.05mol)及び2-メチルピリジン1.1g(0.012mol)を加えた。反応混合物が-70℃まで冷却された後で、四塩化チタン5.0mL(0.05mol)を加えて重合を開始した。重合開始3時間後に、フェノキシエチルアクリレート(ライトアクリレートPO-A、共栄社化学株式会社製)40gと、四塩化チタン110mlとを添加した。その後、-70℃で4時間攪拌を続けた後、メタノール1000mlを添加して反応を停止させた。
・実施例1
本発明の(A)成分として上記合成例1で得られたアクリロイルオキシエトキシフェニル基を有するポリイソブチレン(a1)100質量部と、
(B)成分の(b1-1)成分として4-ヒドロキシブチルアクリレート(4HBA、大阪有機化学工業株式会社製)3質量部と、(b2)成分としてイソボルニルメタクリレート(SR423、サートマー社製)50質量部と、
(C)成分としてビス(2,4,6-トリメチルベンゾイル)-フェニル-フォスフィンオキサイド(Omnirad 819 、IGM Resins B.V.社製)2質量部と、
(D)成分として平均粒径1μmのアクリル樹脂粒子(MR-2G、綜研化学株式会社製)0.05質量部とをプラネタリーミキサーに添加し、遮光下で常温(25℃)にてプラネタリーミキサーで60分混合し、実施例1の光硬化性樹脂組成物を得た。当該光硬化性樹脂組成物は25℃で液状であった。
実施例1において、(b1-1)成分である4-ヒドロキシブチルアクリレートの添加量を6質量部にした以外は、実施例1と同様にして調製し、実施例2の光硬化性樹脂組成物を得た。当該光硬化性樹脂組成物は25℃で液状であった。
実施例1において、(b1-1)成分である4-ヒドロキシブチルアクリレートの代わりに、(b1-2)成分としてヒドロキシプロピルアクリレート(HPA、大阪有機化学工業株式会社製)を用いた以外は、実施例1と同様にして調製し、実施例3の光硬化性樹脂組成物を得た。当該光硬化性樹脂組成物は25℃で液状であった。
実施例1において、(b1-1)成分である4-ヒドロキシブチルアクリレートの代わりに、(b1-3)成分としてヒドロキシエチルアクリレート(HEA、大阪有機化学工業株式会社製)を用いた以外は、実施例1と同様にして調製し、実施例4の光硬化性樹脂組成物を得た。当該光硬化性樹脂組成物は25℃で液状であった。
実施例1において、平均粒径1μmのアクリル樹脂粒子の代わりに、(D)成分として平均粒径6μmのスチレン・オレフィン共重合体粒子(SBX-6、積水化成品工業株式会社製)を用いた以外は、実施例1と同様にして調製し、実施例5の光硬化性樹脂組成物を得た。当該光硬化性樹脂組成物は25℃で液状であった。
実施例1において、(b1-1)成分である4-ヒドロキシブチルアクリレートを除いた以外は、実施例1と同様にして調製し、比較例1の光硬化性樹脂組成物を得た。
実施例1において、(D)成分である平均粒径1μmのアクリル樹脂粒子の代わりに、平均粒径30μmのジルコニア粒子(東ソー株式会社製)を用いた以外は、実施例1と同様にして調製し、比較例2の光硬化性樹脂組成物を得た。
実施例1において、(b2)成分を除き、(b1-1)成分である4-ヒドロキシブチルアクリレートを3質量部から53重量部にした以外は、実施例1と同様にして調製し、
比較例3の光硬化性樹脂組成物を得た。比較例3の光硬化性樹脂組成物は、製造直後に分離してしまった。そのため、特性評価は行うことは困難であった。
確認試験については、下記2水準にて評価試験を実施した。
合格 :試験A、Bの両方の評価試験にて気泡が確認されなかった、
不合格:試験A、Bのいずれかの評価試験にて気泡が確認された。
各光硬化性樹脂組成物0.01gをスライドガラス上に滴下し、カバーグラスを被せて光硬化性樹脂組成物が薄膜としてガラスに挟まれた試験片を作製した。次に紫外線照射機(ウシオ電機株式会社製UniJet L60)により積算光量875mJ/cm2(照度250mW/cm2×3.5秒)となるように活性エネルギー線を照射後、ガラス同士が接着して手で動かせなくなることを確認する試験を行った。
合格 :手で動かなかったので、硬化が確認された、
不合格:手で動いてしまい、未硬化であった。
200mm×200mm×1.0mmの枠に実施例1の光硬化性樹脂組成物を流し込んだ。その後、紫外線照射機により積算光量45kJ/m2になるように紫外線を20秒間照射し、厚さ1.0mmのシート状の硬化物を作製した。塩化カルシウム(無水)5gを直径30mmの開口部を有するアルミニウム製カップに入れて、前記硬化物をカップにセットした。「初期の全重量」(g)を測定した後、雰囲気温度40℃で相対湿度95%に保たれた恒温恒湿槽に24時間放置し、「放置後の全重量」(g)を測定して、透湿度(g/m2・24h)を計算し、下記評価基準に基づき評価した。詳細な試験方法はJIS Z 0208:1976に準拠する。この実施結果を下記表2に示す。なお、透湿度は、燃料電池用硬化性シール剤として使用する場合、10g/m2・24h未満であることが好ましい。
合格 :透湿度が、10g/m2・24h未満、
不合格:透湿度が、10g/m2・24h以上。
実施例1の光硬化性樹脂組成物を用いて紫外線照射機により積算光量45kJ/m2になるように紫外線を20秒間照射し、厚さ1.0mmのシート状の硬化物を作製した。次にシート状の硬化物を用いて、水素ガスの透過度をJIS K7126-1:2006(プラスチック-フィルム及びシート-ガス透過度試験方法-第1部:差圧法)に準拠し測定した。尚、試験の種類は圧力センサ法であり、条件は23℃、高圧側の試験ガス(水素ガス)は100kPaにて測定し、下記評価基準に基づき評価した。この実施結果を下記表2に示す。なお、水素ガスバリア性は、燃料電池用光硬化性シール剤として使用する場合、1×10-15mol・m/m2・s・Pa未満であることが好ましい。
合格 :1×10-15mol・m/m2・s・Pa未満、
不合格:1×10-15mol・m/m2・s・Pa以上。
製造直後の実施例1の光硬化性樹脂組成物と、比較例2の光硬化性樹脂組成物とを、それぞれガラス瓶に入れ、遮光環境下で25℃1ヶ月保存し、その後、相分離の有無を肉眼で確認した。実施例1の評価結果は、分離は確認されなかったので「合格」であり、比較例2の評価結果は、分離が確認されたので「不合格」であった。本発明の光硬化性樹脂組成物において、金属粒子ではなく有機樹脂粒子を採用することにより、相分離を抑制できることが確認された。
製造直後の実施例1との光硬化性樹脂組成物と、比較例1の光硬化性樹脂組成物とを、それぞれガラス瓶に入れ、遮光環境下で25℃1週間保存し、その後、結晶析出の有無を肉眼で確認した。実施例1の評価結果は、「結晶析出なし」だったので「合格」であり、比較例1の評価結果は、「結晶析出あり」だったので「不合格」であった。本発明の光硬化性樹脂組成物において、(B)成分として(b1)成分と、(b2)成分とを組み合わせることによって、結晶化を抑制できることが確認された。
2 セパレーター
3a 空気極(カソード)
3b 燃料極(アノード)
4 高分子電解質膜
5 電解質膜電極接合体(MEA)
6 フレーム
7 接着剤またはシール剤
8a 酸化ガス流路
8b 燃料ガス流路
9 冷却水流路
10 セルスタック
11 固体高分子形燃料電池
Claims (17)
- 下記の(A)~(D)成分を含有することを特徴とする光硬化性樹脂組成物:
(A)成分:1以上の(メタ)アクリロイル基と、-[CH2C(CH3)2]-単位を含むポリイソブチレン骨格とを有するポリマー、
(B)成分:下記の(b1)成分と、(b2)成分とを含む単官能性モノマー、
(b1)成分:(メタ)アクリロイル基と、ヒドロキシ基とを有する単官能性モノマー、
(b2)成分:(メタ)アクリロイル基を有し、ヒドロキシ基を有さない単官能性モノマー、
(C)成分:ラジカル重合開始剤、
(D)成分:有機樹脂粒子。 - 前記(A)成分100質量部に対して、前記(b1)成分を0.1~15質量部含み、前記(b2)成分を5~500質量部を含むことを特徴とする請求項1または2に記載の光硬化性樹脂組成物。
- 前記(D)成分の平均粒径が0.05~50μmであることを特徴とする請求項1~3のいずれか1項に記載の光硬化性樹脂組成物。
- 前記(D)成分が、(メタ)アクリル樹脂粒子、ポリスチレン粒子、スチレン・オレフィン共重合体粒子、ポリエチレン粒子およびポリプロピレン粒子からなる群より選択される少なくとも1種であることを特徴とする請求項1~4のいずれか1項に記載の光硬化性樹脂組成物。
- 前記(b1)成分が、4-ヒドロキシブチル(メタ)アクリレート、3-ヒドロキシプロピル(メタ)アクリレート、2-ヒドロキシプロピル(メタ)アクリレート、2-ヒドロキシエチル(メタ)アクリレート、2-ヒドロキシブチル(メタ)アクリレート、2-ヒドロキシ-3-フェノキシプロピルアクリレート、2-アクリロイロキシエチル-2-ヒドロキシエチル-フタル酸、2-(メタ)アクリロイロキシエチルアシッドホスフェートおよび2-(メタ)アクリロイロキシエチルアシッドホスフェートからなる群より選択される少なくとも1種であることを特徴とする請求項1~5のいずれか1項に記載の光硬化性樹脂組成物。
- 前記(b2)成分が、炭素数5~30のアルキル基または炭素数5~30の脂環式炭化水素基を有し、かつ、ヒドロキシ基を有さない(メタ)アクリレートモノマーであることを特徴とする請求項1~6のいずれか1項に記載の光硬化性樹脂組成物。
- 請求項1~7のいずれか1項に記載の光硬化性樹脂組成物を含む、燃料電池用硬化性シール剤。
- 燃料電池における部材であるセパレーター、フレーム、電解質膜、燃料極、空気極および電解質膜電極接合体からなる群より選択されるいずれかの部材周辺用シール剤である、請求項8に記載の燃料電池用硬化性シール剤。
- 燃料電池における隣り合うセパレーター同士の間のシール剤、または燃料電池のフレームと、電解質膜もしくは電解質膜電極接合体との間のシール剤である、請求項8に記載の燃料電池用硬化性シール剤。
- 固体高分子形燃料電池用シール剤である、請求項8~10のいずれか1項に記載の燃料電池用硬化性シール剤。
- 請求項1~7のいずれか1項に記載の光硬化性樹脂組成物、または請求項8~11のいずれか1項に記載の燃料電池用硬化性シール剤に対して光照射することにより得られる硬化物。
- 燃料電池における隣り合うセパレーター同士の間のシール、および燃料電池のフレームと、電解質膜または電解質膜電極接合体との間のシールからなる群より選択される少なくとも1種のシールを含む燃料電池であって、前記シールのうちの少なくとも1つが、請求項12に記載の硬化物である、燃料電池。
- 固体高分子形燃料電池である、請求項13に記載の燃料電池。
- 少なくとも2つのフランジを有する被シール部品の当該少なくとも2つのフランジの間の少なくとも一部をシールする方法であって、
前記フランジの少なくとも一方が活性エネルギー線の光を透過可能であり、前記フランジの少なくとも一方の表面に、請求項1~7のいずれか1項に記載の光硬化性樹脂組成物を塗布する工程、
前記光硬化性樹脂組成物を塗布した一方のフランジと他方のフランジとを前記光硬化性樹脂組成物を介して貼り合わせる工程、および、
活性エネルギー線を前記光透過可能なフランジを通して照射して前記光硬化性樹脂組成物を硬化させ、前記少なくとも2つのフランジの間の少なくとも一部をシールする工程、
を含むことを特徴とする、方法。 - 少なくとも2つのフランジを有する被シール部品の当該少なくとも2つのフランジの間の少なくとも一部をシールする方法であって、
前記フランジの少なくとも一方のフランジに、請求項1~7のいずれか1項に記載の光硬化性樹脂組成物を塗布する工程、
前記塗布した光硬化性樹脂組成物に活性エネルギー線を照射して前記光硬化性樹脂組成物を硬化させ、前記光硬化性樹脂組成物の硬化物からなるガスケットを形成する工程、および、
他方のフランジを前記ガスケット上に配置して、前記光硬化性樹脂組成物を塗布した一方のフランジと前記他方のフランジとを前記ガスケットを介して圧着し、前記少なくとも2つのフランジの間の少なくとも一部をシールする工程、
を含むことを特徴とする、方法。 - 少なくとも2つのフランジを有する被シール部品の当該少なくとも2つのフランジの間の少なくとも一部をシールする方法であって、
前記フランジの少なくとも一方のフランジ上にガスケット形成用金型を配置する工程、
前記ガスケット形成用金型と該金型を配置したフランジとの間の空隙の少なくとも一部に請求項1~7のいずれか1項に記載の光硬化性樹脂組成物を注入する工程、
前記光硬化性樹脂組成物に活性エネルギー線を照射して前記光硬化性樹脂組成物を硬化させ、前記光硬化性樹脂組成物の硬化物からなるガスケットを形成する工程、
前記金型を前記一方のフランジから取り外す工程、および、
他方のフランジを前記ガスケット上に配置して、前記一方のフランジと前記他方のフランジとを前記ガスケットを介して圧着し、前記少なくとも2つのフランジの間の少なくとも一部をシールする工程、
を含むことを特徴とする、方法。
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EP19887032.1A EP3885380A4 (en) | 2018-11-21 | 2019-10-17 | PHOTOCURED RESIN COMPOSITION, FUEL CELL SEALANT MATERIAL, CURED PRODUCT OF SUCH PHOTOCURED RESIN COMPOSITION, CURED PRODUCT OF SUCH FUEL CELL SEALANT MATERIAL, FUEL CELL AND SEALING METHOD |
CA3118391A CA3118391A1 (en) | 2018-11-21 | 2019-10-17 | Photocurable resin composition, sealing material for fuel cell, cured product thereof, fuel cell, and sealing method |
JP2020558167A JP7393670B2 (ja) | 2018-11-21 | 2019-10-17 | 光硬化性樹脂組成物、燃料電池用シール材およびこれらの硬化物、燃料電池ならびにシール方法 |
US17/295,428 US11787931B2 (en) | 2018-11-21 | 2019-10-17 | Photocurable resin composition, sealing material for fuel cell, cured product thereof, fuel cell, and sealing method |
CN201980070801.6A CN112969732B (zh) | 2018-11-21 | 2019-10-17 | 光固化性树脂组合物、燃料电池用密封材料以及它们的固化物、燃料电池以及密封方法 |
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JP7445044B1 (ja) | 2023-03-02 | 2024-03-06 | 株式会社バルカー | シール材の製造方法 |
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CN117866468B (zh) * | 2024-02-27 | 2024-06-11 | 佛山禾邦新材料科技有限公司 | 一种可双重固化的高润湿性uv三防漆及其制备方法 |
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US20210403699A1 (en) | 2021-12-30 |
CN112969732B (zh) | 2023-11-28 |
EP3885380A1 (en) | 2021-09-29 |
US11787931B2 (en) | 2023-10-17 |
CA3118391A1 (en) | 2020-05-28 |
CN112969732A (zh) | 2021-06-15 |
EP3885380A4 (en) | 2022-11-23 |
JP7393670B2 (ja) | 2023-12-07 |
JPWO2020105333A1 (ja) | 2021-10-07 |
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