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WO2024262261A1 - Composition de résine époxy, et objet durci associé - Google Patents

Composition de résine époxy, et objet durci associé Download PDF

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Publication number
WO2024262261A1
WO2024262261A1 PCT/JP2024/019520 JP2024019520W WO2024262261A1 WO 2024262261 A1 WO2024262261 A1 WO 2024262261A1 JP 2024019520 W JP2024019520 W JP 2024019520W WO 2024262261 A1 WO2024262261 A1 WO 2024262261A1
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WIPO (PCT)
Prior art keywords
epoxy resin
component
resin composition
composition according
mass
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English (en)
Japanese (ja)
Inventor
雄介 今井
向輝 三橋
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ThreeBond Co Ltd
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ThreeBond Co Ltd
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Publication of WO2024262261A1 publication Critical patent/WO2024262261A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/15—Heterocyclic compounds having oxygen in the ring
    • C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
    • C08K5/1515—Three-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L21/00—Compositions of unspecified rubbers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins

Definitions

  • the present invention relates to an epoxy resin composition with high adhesive strength.
  • Epoxy resins have a rigid skeleton and excellent heat and chemical resistance, and are therefore widely used in a variety of fields, including adhesives, paints, civil engineering and construction materials, and insulating materials for electrical and electronic components.
  • plastic materials have been widely used in electrical and electronic components to reduce the weight of the products, but the heat resistance of adherends that contain or consist of plastic materials is low, so epoxy resins that cure at low temperatures are in demand.
  • epoxy resins that cure at low temperatures have been in demand.
  • epoxy resin compositions containing polythiol compounds have been common as epoxy resins that cure at low temperatures (JP Patent Publication No. 2014-173007, JP Patent Publication No.
  • epoxy resin compositions containing polythiol compounds such as those disclosed in JP 2014-173007 A and the like have a characteristic odor that is easily avoided by workers, and there are also problems with the cured products having insufficient moisture resistance.
  • the present invention has been made in consideration of the above circumstances, and aims to provide an epoxy resin composition capable of forming a cured product having high adhesive properties (specifically, excellent in both tensile shear adhesive strength and T-peel adhesive strength). Another aim of the present invention is to provide an epoxy resin composition that can be cured at low temperatures without containing a polythiol compound, and that produces a cured product having high adhesive properties (specifically, excellent in both tensile shear adhesive strength and T-peel adhesive strength).
  • the inventors discovered that the epoxy resin composition described in detail below can form a cured product that is excellent in both tensile shear adhesive strength and T-peel adhesive strength, and thus completed the present invention.
  • An epoxy resin composition comprising the following components (A) to (D): (A) Epoxy resin (excluding component (B) below) (B) a cottonseed oil-derived epoxy resin; (C) rubber particles; (D) a latent curing agent; [2] The epoxy resin composition according to [1], wherein the component (A) is a bisphenol-type epoxy resin; [3] The epoxy resin composition according to [1] or [2], wherein the component (B) is an ester compound derived from a component contained in cottonseed oil and has one or more epoxy groups in the ester moiety; [4] The epoxy resin composition according to any one of [1] to [3], wherein the component (B) has a structure represented by the following formula (1):
  • R is a hydrocarbon group having 13 or more carbon atoms;
  • X to Y is used to mean “X or more and Y or less,” including the numerical values (X and Y) described before and after it as the lower and upper limits.
  • concentration and % represent mass concentration and mass %, respectively, unless otherwise specified, and ratios are mass ratios unless otherwise specified. Unless otherwise specified, operations and measurements of physical properties are performed at room temperature (20-25°C) and relative humidity of 40-55% RH. "A and/or B” means that A and B are included, as well as combinations of these.
  • Epoxy resin composition comprising the following components (A) to (D): (A) Epoxy resin (excluding component (B) below) (B) cottonseed oil derived epoxy resin; (C) rubber particles; (D) latent hardener.
  • the epoxy resin composition having the above structure is also referred to simply as the "epoxy resin composition of the present invention” or simply as the “epoxy resin composition”.
  • the (A) component having the above structure is also referred to simply as the "(A) component of the present invention” or simply as the "(A) component”.
  • the (B) component having the above structure is also referred to simply as the "(B) component of the present invention” or simply as the "(B) component”.
  • the (C) component having the above structure is also referred to simply as the "(C) component of the present invention” or simply as the "(C) component”.
  • the (D) component having the above structure is also referred to simply as the "(D) component of the present invention” or simply as the "(D) component”.
  • the epoxy resin according to the present invention can form a cured product that is excellent in both tensile shear adhesive strength and T-peel adhesive strength. In other words, according to the present invention, it is possible to improve both high adhesive strength and peel strength in a well-balanced manner in the cured product of the epoxy resin composition. In addition, the epoxy resin composition according to the present invention can be cured at low temperatures.
  • the (A) component of the present invention is an epoxy resin.
  • the epoxy resin as the (A) component is not particularly limited as long as it is a compound having one or more epoxy groups.
  • the epoxy group may be contained in the compound (epoxy resin) in the form of a glycidyl group.
  • the (A) component does not include the (B) component (cottonseed oil-derived epoxy resin) described later.
  • the (A) component does not include a compound containing a silicon atom in addition to one or more epoxy groups (i.e., a silane coupling agent described later).
  • the epoxy resin used as component (A) may be solid or liquid, and is preferably liquid from the viewpoint of excellent workability.
  • liquid means a state (liquid state) having fluidity at 25°C.
  • liquid state at 25°C means a state in which the viscosity measured at 25°C at a shear rate of 10s -1 using a cone-plate type rotational viscometer is 100 Pa ⁇ s or less.
  • the viscosity here is the viscosity measured at a shear rate of 10s -1 using a cone-plate type rotational viscometer.
  • the viscosity of the epoxy resin used as component (A) at 25°C is preferably 0.01 Pa ⁇ s or more and less than 100 Pa ⁇ s, more preferably 0.1 to 50 Pa ⁇ s, even more preferably 0.3 to 10 Pa ⁇ s, and particularly preferably 0.5 to 5 Pa ⁇ s.
  • component (A) contains a compound having two or more epoxy groups in one molecule.
  • component (A) contains a polyfunctional epoxy resin having two or more epoxy groups in one molecule.
  • the upper limit of the number of epoxy groups contained in one molecule is not particularly limited, but it is preferable that it is six or less.
  • the number of epoxy groups contained in the compound as component (A) is preferably 2 to 6 (di- to hexafunctional epoxy resin), more preferably 2 to 3 (di- to trifunctional epoxy resin), and particularly preferably 2 (difunctional epoxy resin).
  • the epoxy equivalent of the epoxy resin used as component (A) is not particularly limited, but from the viewpoint of further improving the adhesive properties, it is preferably 50 to 250 g/eq, more preferably 100 to 200 g/eq, and particularly preferably 150 to 195 g/eq.
  • the epoxy equivalent is a value measured in accordance with JIS K-7236:2009.
  • the epoxy equivalent may be calculated as the molecular weight of the target epoxy resin (compound) divided by the number of epoxy groups contained in one molecule of the epoxy resin (compound).
  • epoxy resins used as component (A) include, but are not limited to, bisphenol type epoxy resins such as bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, and bisphenol AD type epoxy resin; hydrogenated bisphenol type epoxy resin; 1,2-butanediol diglycidyl ether, 1,3-butanediol diglycidyl ether, 1,4-butanediol diglycidyl ether, ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 2,3-butanediol diglycidyl ether, 1,5-pentanediol diglycidyl alkylene glycol type epoxy resins such as ether, 1,6-hexanediol diglycidyl ether, neopentyl glycol diglycidyl ether, and 1,4-cyclohexanedimethanol diglycidyl ether; novolac type epoxy resins such as
  • the component (A) used in the present invention is preferably a bisphenol type epoxy resin from the viewpoint of low-temperature curing properties and improved adhesive strength.
  • bisphenol type epoxy resins epoxy resins having a bisphenol skeleton
  • examples of bisphenol type epoxy resins include, but are not limited to, bisphenol A type epoxy resins, bisphenol F type epoxy resins, bisphenol S type epoxy resins, and bisphenol AD type epoxy resins. These may be used alone or in combination of two or more types, but the combined use of bisphenol A type epoxy resins and bisphenol F type epoxy resins can maintain good adhesive properties.
  • bisphenol A type epoxy resins and bisphenol F type epoxy resins are used in combination, it is preferable to include 40 to 60 parts by mass of bisphenol F type epoxy resin for every 50 parts by mass of bisphenol A type epoxy resin.
  • the content of component (A) in the epoxy resin composition is not particularly limited, but is preferably 20 to 80 parts by mass, more preferably 30 to 70 parts by mass, and particularly preferably 40 to 60 parts by mass, per 100 parts by mass of the total mass of the epoxy resin composition.
  • the compound as component (A) may be used alone or in combination of two or more types. When two or more types are used in combination, the content of component (A) refers to the total amount.
  • bisphenol-type epoxy resins include, but are not limited to, jER (registered trademark) 828, 1001, 801, 806, 807, 152, 604, 630, 871, YX8000, YX8034, and YX4000 (manufactured by Mitsubishi Chemical Corporation), EPICLON (registered trademark) 830, 850, 830LVP, 850CRP, 835LV, HP4032D, 703, 720, 726, and 820 (manufactured by DIC Corporation), EP4100, E P4000, EP4080, EP4085, EP4088, EPU6, EPU7N, EPR4023, EPR1309, EP4920 (manufactured by ADEKA Corporation), TEPIC (registered trademark) (manufactured by Nissan Chemical Industries, Ltd.), KF-101, KF-1001, KF-105, X-22-163B, X-22-9002 (manufactured by Shin-Etsu Chemical Co
  • the (B) component of the present invention is a cottonseed oil-derived epoxy resin.
  • the cottonseed oil-derived epoxy resin refers to an epoxy resin made from cottonseed oil.
  • the cottonseed oil-derived epoxy resin is a compound obtained from a component contained in cottonseed oil, and is not particularly limited as long as it has one or more epoxy groups in one molecule. From the viewpoint of further improving the adhesive properties, it is preferable that the number of epoxy groups contained in the (B) component is one (the (B) component is a monofunctional epoxy resin).
  • the epoxy group may be contained in the component in the form of a glycidyl group.
  • the (B) component does not include a compound containing a silicon atom in addition to one or more epoxy groups (i.e., a silane coupling agent described later).
  • cottonseed oil is an oil made from cotton seeds, and is a natural ingredient having a fatty acid composition consisting mainly of linoleic acid, palmitic acid, and oleic acid, as well as stearic acid, palmitoleic acid, myristic acid, and linolenic acid.
  • Components contained in cottonseed oil include saturated fatty acids such as palmitic acid (C 15 H 31 -COOH), myristic acid (C 13 H 27 -COOH), stearic acid (C 17 H 35 -COOH), pentadecanoic acid (C 14 H 29 -COOH), arachidic acid (C 19 H 39 -COOH), behenic acid (C 21 H 43 -COOH), and lignoceric acid (C 23 H 47 -COOH); monounsaturated fatty acids such as oleic acid (C 17 H 33 -COOH), palmitoleic acid (C 15 H 29 -COOH), icosenoic acid (C 19 H 37 -COOH), and tetracosenoic acid (nervonic acid, C 23 H 45 -COOH); linoleic acid (C 17 H 31 -COOH), and polyunsaturated fatty acids such as oleic acid (C 17 H 33 -COOH), palmitoleic
  • an epoxy resin "derived from” a component contained in cottonseed oil means that the epoxy resin is an epoxy resin (including an epoxy monomer) having a structural unit (structure) generated by a condensation reaction (e.g., an esterification reaction) of a reactive group contained in at least one component among the components contained in cottonseed oil.
  • the cottonseed oil-derived epoxy resin as component (B) is preferably substantially free of epoxidized cottonseed oil, which is a compound obtained by epoxidizing an unsaturated bond in an unsaturated fatty acid contained in cottonseed oil.
  • the epoxy resin composition is substantially free of the above-mentioned epoxidized cottonseed oil.
  • the term "substantially free of" a certain component means that the content of the component is 0.5% by mass or less, preferably 0.1% by mass or less, and most preferably 0% by mass, relative to the total mass of the epoxy resin composition.
  • the epoxy resin composition according to the present invention is presumed to have high toughness (stickiness) by including an epoxy compound derived from a long-chain fatty acid (a fatty acid having 12 or more carbon atoms) as described above as component (B).
  • component (B) an epoxy compound derived from a long-chain fatty acid (a fatty acid having 12 or more carbon atoms) as described above as component (B).
  • component (B) an epoxy compound derived from a fatty acid having 12 or more carbon atoms
  • the resulting cured product also has high toughness and exhibits high adhesive properties.
  • an epoxy compound derived from a fatty acid having a short carbon chain (fewer than 12 carbon atoms) is used instead of component (B)
  • the toughness of the epoxy resin composition and its cured product decreases, and the adhesive properties decrease (Comparative Example 4 described below).
  • excellent adhesive properties are not obtained when component (B) is not used (Comparative Examples 1 and 3 described below). Note that the above mechanism is based on speculation, and whether
  • the (B) component preferably has a structure represented by the following formula (1).
  • the (B) component preferably contains a glycidyl ester having a structure represented by formula (1).
  • the cured product of the epoxy resin composition can exhibit high adhesive strength.
  • R is a hydrocarbon group having 13 or more carbon atoms.
  • hydrocarbon group means a group consisting of carbon atoms and hydrogen atoms bonded thereto.
  • Hydrocarbon groups include saturated or unsaturated, linear, branched, or cyclic hydrocarbon groups. Examples of hydrocarbon groups include aliphatic (chain) hydrocarbon groups such as linear or branched alkyl groups, alkenyl groups, and alkynyl groups; alicyclic hydrocarbon groups such as cycloalkyl groups, cycloalkenyl groups, and cycloalkynyl groups; aromatic hydrocarbon groups such as aryl groups; and combinations of these, such as aralkyl groups and arylalkyl groups.
  • R is preferably a hydrocarbon group having 13 to 25 carbon atoms, more preferably a hydrocarbon group having 13 to 20 carbon atoms, even more preferably a hydrocarbon group having 16 to 18 carbon atoms, and particularly preferably a hydrocarbon group having 17 carbon atoms.
  • R is preferably an aliphatic (chain) hydrocarbon group having 13 to 25 carbon atoms, more preferably an aliphatic (chain) hydrocarbon group having 13 to 20 carbon atoms, even more preferably an aliphatic (chain) hydrocarbon group having 16 to 18 carbon atoms, and particularly preferably an aliphatic (chain) hydrocarbon group having 17 carbon atoms.
  • R is preferably an alkenyl group having one or more unsaturated bonds, and more preferably an alkenyl group containing one or two unsaturated bonds. Furthermore, from the viewpoint of adhesive properties, R is preferably linear.
  • R is preferably a linear alkenyl group having 13 to 25 carbon atoms, more preferably a linear alkenyl group having 13 to 20 carbon atoms, even more preferably a linear alkenyl group having 16 to 18 carbon atoms, and particularly preferably a linear alkenyl group having 17 carbon atoms.
  • the number of unsaturated bonds contained in the alkenyl group is preferably 1 or 2.
  • the (B) component is preferably an epoxy resin derived from at least one selected from the mono- and poly-unsaturated fatty acids contained in cottonseed oil, and more preferably an epoxy resin derived from at least one selected from the mono- and di-unsaturated fatty acids contained in cottonseed oil.
  • the (B) component preferably includes an epoxy resin derived from at least one selected from the group consisting of oleic acid, palmitoleic acid, icosenoic acid, tetracosenoic acid (nervonic acid), linoleic acid, and linolenic acid.
  • the (B) component preferably includes an epoxy resin derived from at least one selected from the group consisting of oleic acid, palmitoleic acid, icosenoic acid, tetracosenoic acid (nervonic acid), and linoleic acid. In yet another embodiment, the (B) component preferably includes an epoxy resin derived from oleic acid and/or linoleic acid.
  • component (B) contains at least one selected from the group consisting of linoleic acid glycidyl ester, oleic acid glycidyl ester, linolenic acid glycidyl ester, palmitoleic acid glycidyl ester, icosenoic acid glycidyl ester, and tetracosenoic acid glycidyl ester, more preferably contains at least one selected from the group consisting of linoleic acid glycidyl ester, oleic acid glycidyl ester, palmitoleic acid glycidyl ester, icosenoic acid glycidyl ester, and tetracosenoic acid glycidyl ester, and it is particularly preferable that component (B) contains linoleic acid glycidyl ester and/or
  • Component (B) may be either a synthetic product or a commercially available product. There are no particular limitations on the method for synthesizing component (B) as long as it is a method that can epoxidize the components contained in cottonseed oil. Examples of methods for synthesizing component (B) include a method of epoxidizing a carboxy group contained in a component contained in cottonseed oil, a method of esterifying a carboxy group contained in a component contained in cottonseed oil with an alcohol compound that has an epoxy group (glycidyl group), and a method of epoxidizing an unsaturated double bond contained in a component contained in cottonseed oil.
  • the content of the (B) component in the epoxy resin composition is preferably 0.1 to 50 parts by mass, more preferably 1 to 40 parts by mass, even more preferably 3 to 25 parts by mass, particularly preferably 8 to 20 parts by mass, and most preferably 12 to 18 parts by mass, relative to 100 parts by mass of the (A) component.
  • the cottonseed oil-derived epoxy resin as the (B) component may be used alone or in combination of two or more types. When two or more types are used in combination, the content of the (B) component refers to the total amount.
  • the component (C) of the present invention is a rubber particle.
  • the rubber particle here means a particle including a layer exhibiting rubber elasticity.
  • the rubber particle may be a particle consisting of only one layer exhibiting rubber elasticity, or may be a particle (core-shell particle) having a multi-layer structure having at least one layer exhibiting rubber elasticity. From the viewpoint of adhesive properties, the component (C) is preferably a core-shell particle.
  • Core-shell particles are particles in which the core layer (nucleus) and shell layer (wall) of the particle are made of polymers with different properties.
  • a preferred method for producing core-shell particles (powder particles) is as follows: First, a polymerizable monomer that forms the core layer is polymerized (first polymerization step).
  • this polymerizable monomer examples include (meth)acrylate monomers such as methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, n-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, n-decyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 3-hydroxybutyl (meth)acrylate, and 2-butoxyethyl (meth)acrylate; aromatic vinyl compounds such as styrene, vinyl toluene, and isopropenyl benzene ( ⁇ -methylstyrene); vinyl cyanide compounds such as acrylonitrile, methacrylonitrile, and vinylidene cyanide; and 2-hydroxyethyl fumarate, hydroxybutyl vinyl ether, and monobutyl maleate.
  • (meth)acrylate monomers such as methyl (meth)acrylate,
  • examples of the polymerizable monomer include crosslinkable monomers having two or more reactive groups such as ethylene glycol di(meth)acrylate, butylene glycol di(meth)acrylate, trimethylolpropane di(meth)acrylate, trimethylolpropane tri(meth)acrylate, hexanediol di(meth)acrylate, hexanediol tri(meth)acrylate, oligoethylene glycol di(meth)acrylate, and trimethylolpropane polyethylene tri(meth)acrylate; aromatic divinyl monomers such as divinylbenzene; triallyl trimellitate, triallyl isocyanurate, and the like.
  • crosslinkable monomers having two or more reactive groups such as ethylene glycol di(meth)acrylate, butylene glycol di(meth)acrylate, trimethylolpropane di(meth)acrylate, trimethylolpropane tri(meth)acrylate, hexane
  • polymerizable monomers can be used alone or in combination.
  • the polymer particles obtained using the above-mentioned polymerizable monomers are used as the core layer, and the polymerizable monomer is polymerized so as to have a different composition from that of the core layer to form a shell layer (second polymerization step).
  • Specific examples of the polymerizable monomers used at this time include the same polymerizable monomers as those for obtaining the above-mentioned core layer, and can be selected from these and used.
  • a (meth)acrylate having an alkyl group (an alkyl group bonded to a (meth)acryloyloxy group) with 1 to 4 carbon atoms is preferred. Specific examples include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, and n-butyl (meth)acrylate.
  • the rubber particles as component (C) are poly(meth)acrylate-based core-shell particles containing at least one (co)polymer selected from the group consisting of polyacrylate polymers, polymethacrylate polymers, and acrylate-methacrylate copolymers.
  • the (C) component is not particularly limited, but examples thereof include butadiene rubber particles, acrylic rubber particles, silicone rubber particles, butyl rubber particles, olefin rubber particles, high styrene rubber particles, NBR (nitrile rubber) particles, SBR (styrene butadiene rubber) particles, IR (isoprene rubber) particles, EPR (ethylene propylene rubber) particles, etc.
  • butadiene rubber particles and/or acrylic rubber particles are preferred as the (C) component, with acrylic rubber particles being particularly preferred.
  • the component (D) of the present invention is a latent curing agent.
  • the latent curing agent is a compound that is inactive to the epoxy resin as the component (A) and the cottonseed oil-derived epoxy resin as the component (B) at room temperature (25°C), and is activated by dissolution, decomposition, transition reaction, etc., when a stimulus such as heating is applied, and has the function of promoting the curing of the above-mentioned components (A) and (B).
  • the latent curing agent that is activated by heating various conventionally known substances can be used.
  • Such substances include dicyandiamide and its derivatives, hydrazide compounds, amine imides, amine adduct compounds which are reaction products of amine compounds with epoxy compounds, isocyanate compounds, or urea compounds, acid anhydrides, phenol novolac resins, etc. These may be used alone, or two or more of them may be used in combination.
  • the (D) component preferably contains at least one selected from the group consisting of the compounds listed above, and more preferably is at least one selected from the group consisting of the compounds listed above.
  • the (D) component is preferably an amine adduct compound, and an amine adduct compound of a modified aliphatic polyamine is particularly preferred.
  • the (D) component is preferably solid.
  • the preferred softening point is 60 to 150°C, more preferably 100 to 140°C, and particularly preferably 115 to 125°C. The softening point here is a value measured by the ring and ball method.
  • the (D) component may be in the form of a microcapsule-type curing agent.
  • the content of component (D) is preferably 1 to 60 parts by mass, more preferably 3 to 45 parts by mass, even more preferably 5 to 30 parts by mass, and particularly preferably 10 to 25 parts by mass, relative to 100 parts by mass of component (A).
  • the latent curing agent as component (D) may be used alone or in combination of two or more types. When two or more types are used in combination, the content of component (D) refers to the total amount.
  • amine adduct type latent hardeners include Fujicure (registered trademark) FXE-1000, FXR-1020, FXR-1030, FXB-1050, FXR-1081 (manufactured by T&K Toka Corporation), Amicure (registered trademark, the same applies below) PN-23, Amicure PN-H, Amicure PN-31, Amicure PN-40, Amicure PN-50, Amicure PN-F, Amicure PN-23J, Amicure PN-31J, Amicure PN-40J, Amicure MY-24, Amicure MY-25, Amicure MY-R, Amicure PN-R (manufactured by Ajinomoto Fine-Techno Co., Ltd.), etc. These may be used alone or in combination of two or more.
  • the epoxy resin composition according to the present invention preferably further contains an inorganic filler as component (E).
  • the epoxy resin composition contains an inorganic filler, which can improve the adhesive strength.
  • the inorganic filler as component (E) include glass powder, silica powder, talc powder, alumina powder, mica powder, ceramic powder, silicone powder, calcium carbonate powder, aluminum nitride powder, carbon powder, kaolin clay powder, dried clay mineral powder, dried diatomaceous earth powder; carbon black, barium sulfate, alumina white, clay, titanium oxide; ZnS:Ag, ZnS:Cu, ZnS:Mn, SrAl 2 O 4 :Eu, Sr 4 Al 14 O 25 :Eu, Y 2 O 2 S:Eu, Y 2 O 3 :Eu, etc.
  • the carbon black, barium sulfate, alumina white, clay, titanium oxide, etc. can also function as a colorant (inorganic pigment).
  • ZnS : Ag , ZnS:Cu, ZnS: Mn , SrAl2O4 :Eu , Sr4Al14O25 :Eu, Y2O2S :Eu, Y2O3 : Eu , and the like can also function as colorants (fluorescent inorganic pigments).
  • component (E) contains at least one selected from the group consisting of glass powder, silica powder, talc powder, and calcium carbonate powder, it is more preferable that it contains at least one selected from the group consisting of silica powder, talc powder, and calcium carbonate powder, it is even more preferable that it contains at least one selected from the group consisting of silica powder and calcium carbonate powder, it is particularly preferable that it contains calcium carbonate powder, and it is most preferable that it contains calcium carbonate powder derived from scallop shells. Calcium carbonate powder derived from scallop shells contains trace amounts of organic components, and is therefore highly effective in improving toughness and is excellent in improving adhesive properties.
  • Calcium carbonate powder is a softer (tougher) material than other inorganic fillers such as glass. Therefore, an epoxy resin composition containing calcium carbonate powder not only has the general effect of an inorganic filler of improving the resin strength of the cured product, but also maintains toughness, which is thought to improve the adhesive properties to the adherend. Furthermore, by including calcium carbonate powder derived from scallop shells, the toughness of the epoxy resin composition is increased, resulting in improved adhesive properties.
  • the average particle size of component (E) is preferably 0.01 to 30 ⁇ m, more preferably 0.1 to 15 ⁇ m, even more preferably greater than 1.1 ⁇ m and equal to or less than 15 ⁇ m, particularly preferably 5 to 15 ⁇ m, and most preferably 9 to 15 ⁇ m.
  • the method for measuring the average particle size is the laser diffraction/scattering method (particle size at a cumulative volume ratio of 50%: D50).
  • the content of the (E) component in the epoxy resin composition is preferably 1 to 120 parts by mass, more preferably 10 to 110 parts by mass, even more preferably 10 to 105 parts by mass, even more preferably 10 to 100 parts by mass, even more preferably 20 to 100 parts by mass, particularly preferably 20 to 90 parts by mass, and most preferably 50 to 80 parts by mass, relative to 100 parts by mass of the (A) component. If the content of the (E) component is 1 to 120 parts by mass, the adhesive properties can be maintained well.
  • the inorganic filler as the (E) component may be used alone or in combination of two or more types. When two or more types are used in combination, the content of the (E) component refers to the total amount.
  • Scallop Powder R
  • Scallop Powder S
  • Scallop Shell Calcium Carbonate manufactured by Nomura Sangyo Co., Ltd.
  • the epoxy resin composition may or may not further contain additives (optional components) such as a dispersant, a silane coupling agent, a colorant, a rheology control agent, and a storage stabilizer, as long as the properties of the present invention are not impaired.
  • additives such as a dispersant, a silane coupling agent, a colorant, a rheology control agent, and a storage stabilizer
  • an epoxy resin composition is also provided that includes the above components (A) to (D) and at least one selected from the group consisting of a dispersant, a silane coupling agent, a colorant, a rheology control agent, and a storage stabilizer.
  • an epoxy resin composition is also provided that includes the above components (A) to (D) and at least one selected from the group consisting of a colorant and a storage stabilizer.
  • an epoxy resin composition is also provided that includes the above components (A) to (D) and a storage stabilizer.
  • an epoxy resin composition is also provided that includes the above components (A) to (E) and at least one selected from the group consisting of a dispersant, a silane coupling agent, a colorant, a rheology control agent, and a storage stabilizer.
  • an epoxy resin composition is also provided that includes the above components (A) to (E) and at least one selected from the group consisting of a colorant and a storage stabilizer.
  • an epoxy resin composition comprising the above components (A) to (E) and a storage stabilizer.
  • the dispersant is an auxiliary agent for uniformly dispersing the (C), (D), and (E) components in the (A) component.
  • the inclusion of a dispersant in the epoxy resin composition can suppress settling and separation of the (C), (D), and (E) components in the (A) component over time, improving storage stability.
  • the dispersant there are no particular limitations on the dispersant, so long as it can disperse the (C), (D), and (E) components in the (A) component.
  • the dispersant it is preferable for the dispersant to include at least one selected from the group consisting of carboxylates and phosphate esters.
  • Silane coupling agents include, for example, epoxy group-containing silane coupling agents such as 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropylmethyldipropyloxysilane, 3-glycidoxypropyldimethylmonomethoxysilane, 3-glycidoxypropyldimethylmonoethoxysilane, 3-glycidoxypropyldimethylmonopropyloxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, and 3-glycidoxypropylmethyldiethoxysilane; vinyl group-containing silane coupling agents such as vinyltris(2-methoxyethoxy)silane, vinyltri
  • glycidyl group-containing silane coupling agents are more preferred from the viewpoint of excellent adhesive strength.
  • glycidyl group-containing silane coupling agents i.e., compounds containing epoxy groups and silicon atoms
  • the amount (content) of the silane coupling agent is preferably 0.1 to 20 parts by mass relative to 100 parts by mass of component (A) of the present invention. If the content of the silane coupling agent is 0.1 to 20 parts by mass, the adhesive strength can be maintained well. Note that the silane coupling agent is not included in component (A) or component (B) of the present invention.
  • Colorants include, but are not limited to, organic pigments such as indanthrone blue, quinacridone red, dioxazine violet, and phthalocyanine blue, fluorescent organic pigments, and dyes. Note that the colorants referred to here do not include the component (E) of the present invention.
  • Rheology control agents are additives that act to control rheological properties, and are also known as thixotropic agents, anti-settling agents, anti-sagging agents, thickeners, etc.
  • rheology control agents include organic rheology control agents, and specific examples include fatty acid amide-based rheology control agents and ethyl cellulose-based rheology control agents, but are not limited to these.
  • Storage stabilizers include borate ester compounds, phosphoric acid, alkyl phosphate esters, p-toluenesulfonic acid, and methyl p-toluenesulfonate.
  • Borate ester compounds include, but are not limited to, triethyl borate, tributyl borate, and trimethoxyboroxine.
  • Alkyl phosphate esters include, but are not limited to, trimethyl phosphate and tributyl phosphate.
  • Storage stabilizers may be used alone or in combination. In consideration of storage stability, it is preferable to use at least one selected from the group consisting of tributyl borate, trimethoxyboroxine, phosphoric acid, and methyl p-toluenesulfonate.
  • the epoxy resin composition according to the present invention is preferably substantially composed of the above components (A) to (D), and at least one selected from the group consisting of a dispersant, a silane coupling agent, a colorant, a rheology control agent, and a storage stabilizer.
  • the epoxy resin composition is preferably substantially composed of the above components (A) to (D), and at least one selected from the group consisting of a colorant and a storage stabilizer.
  • the epoxy resin composition is preferably substantially composed of the above components (A) to (D), and a storage stabilizer.
  • the epoxy resin composition according to the present invention is substantially composed of the above components (A) to (E) and at least one selected from the group consisting of a dispersant, a silane coupling agent, a colorant, a rheology control agent, and a storage stabilizer. Also, according to another embodiment of the present invention, it is preferable that the epoxy resin composition is substantially composed of the above components (A) to (E) and at least one selected from the group consisting of a colorant and a storage stabilizer. Also, according to another embodiment of the present invention, it is preferable that the epoxy resin composition is substantially composed of the above components (A) to (E) and a storage stabilizer.
  • the epoxy resin composition is substantially composed of X
  • the total content of X exceeds 99% by mass (upper limit: 100% by mass) (relative to the epoxy resin composition), with the total mass of the epoxy resin composition being 100% by mass.
  • the epoxy resin composition is substantially composed of the above components (A) to (D), and at least one selected from the group consisting of a dispersant, a silane coupling agent, a colorant, a rheology control agent, and a storage stabilizer
  • a dispersant, a silane coupling agent, a colorant, a rheology control agent, and a storage stabilizer means that the total content of the above components (A) to (D), and the dispersant, silane coupling agent, colorant, rheology control agent, and storage stabilizer exceeds 99% by mass (upper limit: 100% by mass) (relative to the epoxy resin composition), assuming that the total mass of the epoxy resin composition is 100% by mass.
  • the preferred content of the above components (A) to (E), dispersant, silane coupling agent, colorant, rheology control agent, and storage stabilizer in each of the above embodiments can be selected and combined by referring to the content ranges described in the sections describing each component above.
  • the epoxy resin composition can be produced by a conventional method.
  • the epoxy resin composition according to the present invention can be obtained by weighing out predetermined amounts of the components (A) to (D), the component (E) added as necessary, and the optional components, and mixing them using a mixing means such as a planetary mixer.
  • a mixing means such as a planetary mixer.
  • another aspect of the present invention also provides a method for producing an epoxy resin composition, which includes mixing the components (A) to (D).
  • the production method may optionally further include mixing the component (E).
  • the component (E) to be mixed preferably includes at least one selected from the group consisting of glass powder, silica powder, talc powder, and calcium carbonate powder, more preferably includes at least one selected from the group consisting of silica powder, talc powder, and calcium carbonate powder, even more preferably includes at least one selected from the group consisting of silica powder and calcium carbonate powder, particularly preferably includes calcium carbonate powder, and most preferably includes calcium carbonate powder derived from scallop shells.
  • the above-mentioned manufacturing method may optionally further comprise mixing at least one selected from the group consisting of a dispersant, a silane coupling agent, a colorant, a rheology control agent and a storage stabilizer, may further comprise mixing a colorant and/or a storage stabilizer, or may further comprise mixing a storage stabilizer.
  • the manufacturing conditions are not particularly limited, but the composition can be manufactured by mixing the components at a temperature of preferably 10 to 70°C for a period of preferably 0.1 to 5 hours.
  • Another aspect of the present invention also provides a cured product obtained by curing the above-mentioned epoxy resin composition.
  • the method of curing the epoxy resin composition to obtain the cured product is not particularly limited and can be appropriately selected depending on the desired application.
  • One example is a method in which the epoxy resin composition is applied to an adherend to form a coating film (application method/step), and then the coating film is cured (curing method/step).
  • application method/step application method/step
  • curing method/step cuing method/step
  • the epoxy resin composition according to the present invention is preferably in a liquid state (liquid) at 25°C. Such a form makes it easy to apply to an adherend.
  • a known application method for a sealant or adhesive can be used as is or with appropriate modification.
  • a method such as dispensing using an automatic coater, spraying, inkjet, screen printing, gravure printing, dipping, or spin coating can be used.
  • the preferred viscosity of the epoxy resin composition is, for example, 1 to 100 Pa ⁇ s, more preferably 3 to 50 Pa ⁇ s, and particularly preferably 5 to 10 Pa ⁇ s.
  • the above viscosity is intended to be a value measured by the method and conditions described in the examples.
  • the epoxy resin composition according to the present invention can be cured at a low temperature.
  • the curing temperature is specifically 50 to 120°C, may be 60 to 110°C, or may be 70 to 100°C.
  • the curing time is not particularly limited, but is preferably 10 minutes to 5 hours, more preferably 20 minutes to 2 hours.
  • the epoxy resin composition according to the present invention can be cured at a low temperature even if it does not contain a polythiol compound.
  • the "polythiol compound” refers to a compound having two or more thiol groups in one molecule.
  • the epoxy resin composition according to the present invention contains the above components (A) to (D), the component (E) added as necessary, and the above optional components, and is substantially free of a polythiol compound.
  • substantially free of a certain component means that the content of the component is 0.5% by mass or less, preferably 0.1% by mass or less, and most preferably 0% by mass, relative to the total mass of the epoxy resin composition.
  • Tensile shear adhesive strength The cured product obtained by curing the epoxy resin composition according to the present invention has excellent tensile shear adhesive strength.
  • the tensile shear adhesive strength of the cured product is, for example, 20.0 MPa or more, preferably 22.0 MPa or more, and more preferably 25.0 MPa or more.
  • the upper limit is not particularly limited, but may be, for example, 50.0 MPa or less, or 30.0 MPa or less.
  • the tensile shear adhesive strength is a value measured by the method described in the examples.
  • the cured product obtained by curing the epoxy resin composition according to the present invention has excellent T-peel adhesive strength.
  • the T-peel adhesive strength of the cured product is, for example, 1.0 kN/m or more, preferably 1.3 kN/m or more, and more preferably 1.5 kN/m or more.
  • the upper limit is not particularly limited, but may be, for example, 4.0 kN/m or less, or 3.0 kN/m or less.
  • the T-peel adhesive strength is a value measured by the method described in the examples.
  • the cured product obtained by curing the epoxy resin composition according to the present invention preferably has a tensile shear adhesive strength and a T-peel adhesive strength both within the above-mentioned preferred ranges.
  • the tensile shear adhesive strength of the cured product is 20.0 MPa or more, and the T-peel adhesive strength of the cured product is 1.0 kN/m or more.
  • it is more preferable that the tensile shear adhesive strength of the cured product is 22.0 MPa or more, and the T-peel adhesive strength of the cured product is 1.3 kN/m or more.
  • it is particularly preferable that the tensile shear adhesive strength of the cured product is 25.0 MPa or more, and the T-peel adhesive strength of the cured product is 1.5 kN/m or more.
  • the epoxy resin composition according to the present invention has high adhesive properties (particularly tensile shear adhesive strength and T-peel adhesive strength) and can be cured at low temperature, and therefore can be used in various applications. Specific examples include, in the field of automobile parts, adhesion, sealing, casting, coating, etc. of switches, headlamps, internal engine parts, electrical components, drive engines, brake oil tanks, front hoods, fenders, body panels such as doors, windows, etc.; in the field of electronic materials, adhesion, sealing, casting, coating, etc.
  • the epoxy resin composition according to the present invention can be used for adhesion, sealing, coating, etc. of batteries, manganese batteries, alkaline batteries, fuel cells, silicon solar cells, dye-sensitized batteries, organic solar cells, etc.; in the optical parts field, adhesion, sealing, etc.
  • optical fiber materials around optical switches and optical connectors, optical passive components, optical circuit components, and around optoelectronic integrated circuits in the optical equipment field, adhesion, sealing, etc. of camera modules, lens materials, finder prisms, target prisms, finder covers, light receiving sensor parts, photographing lenses, our company's lenses for projection televisions, etc.; in the infrastructure field, it can be used as an adhesion, lining material, sealing material, etc. for gas pipes, water pipes, etc.
  • the epoxy resin composition according to the present invention can be cured at low temperatures and has high adhesive properties, so it can be suitably used for adhesion applications.
  • epoxy resin compositions were prepared as follows:
  • A-1) Bisphenol A type/F type mixed epoxy resin (bifunctional) Product name: EPICLON (registered trademark) EXA-835LV (manufactured by DIC Corporation) Mixture of bisphenol A type epoxy resin and bisphenol F type epoxy resin (mass ratio 50:50) Epoxy equivalent: 165 g/eq Viscosity (25° C.): 2 Pa ⁇ s
  • ⁇ Adhesive properties> (Tensile shear adhesive strength) Measurement of tensile shear adhesive strength: Iron test pieces (SPCC-SD steel plate, width 25 mm x length 100 mm x thickness 1.6 mm) were bonded together by the following procedure. After applying an epoxy resin composition to one of the test pieces and spreading it evenly, the other test piece was bonded to the test piece so that the adhesive surface was 25 mm in the width direction and 10 mm in the length direction. The bonded test pieces were fixed with a jig and heated at 80°C for 60 minutes in a hot air drying oven to harden.
  • test pieces After the temperature of the test pieces returned to room temperature (25°C), the prepared test pieces were measured with a tensile tester at a tensile speed of 10 mm/min, and the "tensile shear adhesive strength" (MPa) was obtained. The details of the test were in accordance with JIS K6850:1999. The evaluation criteria for tensile shear adhesive strength are as follows:
  • T-type peel strength Iron test pieces bent into an L-shape (SPCC-SD steel plate, width 25 mm ⁇ length 150 mm ⁇ thickness 0.5 mm, but bent into an L-shape at a point 100 mm long (100 mm from the end)) were bonded together by the following procedure. An epoxy resin composition was applied to a 100 mm long surface of one of the test pieces and uniformly stretched, and then the other test piece was bonded to form a T-shape. The bonded test pieces were heated in a hot air drying oven at 80°C for 60 minutes while being fixed with a jig, and cured.
  • T-peel adhesive strength (kN/m) was obtained.
  • the evaluation criteria for T-peel adhesive strength are as follows.
  • Examples 1 to 6 show that the epoxy resin composition of the present invention has excellent adhesion properties, with both excellent tensile shear adhesive strength and T-peel adhesive strength.
  • Examples 1 to 3 which use calcium carbonate powder derived from scallop shells as component (E) among inorganic fillers, show particularly high tensile shear adhesive strength.
  • Comparative Example 1 did not contain the components (B) and (C) of the present invention, and therefore both the tensile shear adhesive strength and the T-type peel adhesive strength were inferior.
  • Comparative Example 2 did not contain the component (C) of the present invention, and therefore both the tensile shear adhesive strength and the T-type peel adhesive strength were inferior.
  • Comparative Example 3 did not contain the component (B) of the present invention, and therefore both the tensile shear adhesive strength and the T-type peel adhesive strength were inferior.
  • Comparative Example 4 used a monofunctional epoxy resin that is not a cottonseed oil-derived epoxy resin as the component (B'-1) (a component that is not the component (B) of the present invention) instead of the (B) of the present invention, and further did not contain the component (E) of the present invention, and therefore both the tensile shear adhesive strength and the T-type peel adhesive strength were inferior.
  • the epoxy resin composition of the present invention has high adhesive strength. Therefore, the epoxy resin composition of the present invention is useful as an adhesive, sealant, coating agent, etc. that can be used on various components, and is therefore industrially useful.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Epoxy Resins (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention fournit une composition de résine époxy qui présente des caractéristiques adhésives élevées.　La composition de résine époxy de l'invention contient les composants (A) à (D) suivants : (A) une résine époxy (le composant (B) étant exclu) ; (B) une résine époxy dérivée d'une huile de noyaux de coton ; (C) des particules de caoutchouc ; et (D) un agent de durcissement latent.
PCT/JP2024/019520 2023-06-22 2024-05-28 Composition de résine époxy, et objet durci associé Pending WO2024262261A1 (fr)

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5849720A (ja) * 1981-09-18 1983-03-24 Okamura Seiyu Kk エポキシ樹脂用反応性希釈剤
JPH05117499A (ja) * 1991-10-30 1993-05-14 Lion Corp 反応性希釈剤及びそれを含有するエポキシ樹脂組成物
WO2008127925A2 (fr) * 2007-04-11 2008-10-23 Dow Global Technologies, Inc. Résines époxy structurelles contenant des caoutchoucs à noyau-enveloppe
JP2010523800A (ja) * 2007-04-11 2010-07-15 ダウ グローバル テクノロジーズ インコーポレイティド 耐熱性構造用エポキシ樹脂
WO2015053289A1 (fr) * 2013-10-11 2015-04-16 株式会社カネカ Composition de résine époxy contenant un polymère cœur-écorce, produit durci associé et son procédé de production
WO2016130455A1 (fr) * 2015-02-11 2016-08-18 Dow Global Technologies Llc Adhésifs durcissables à basse température et leur utilisation
JP2016199739A (ja) * 2015-04-10 2016-12-01 株式会社カネカ 貯蔵安定性および接着性の改善されたポリマー微粒子含有硬化性樹脂組成物
WO2018030184A1 (fr) * 2016-08-10 2018-02-15 株式会社スリーボンド Composition de résine époxy, et adhésif conducteur contenant celle-ci

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5849720A (ja) * 1981-09-18 1983-03-24 Okamura Seiyu Kk エポキシ樹脂用反応性希釈剤
JPH05117499A (ja) * 1991-10-30 1993-05-14 Lion Corp 反応性希釈剤及びそれを含有するエポキシ樹脂組成物
WO2008127925A2 (fr) * 2007-04-11 2008-10-23 Dow Global Technologies, Inc. Résines époxy structurelles contenant des caoutchoucs à noyau-enveloppe
JP2010523800A (ja) * 2007-04-11 2010-07-15 ダウ グローバル テクノロジーズ インコーポレイティド 耐熱性構造用エポキシ樹脂
WO2015053289A1 (fr) * 2013-10-11 2015-04-16 株式会社カネカ Composition de résine époxy contenant un polymère cœur-écorce, produit durci associé et son procédé de production
WO2016130455A1 (fr) * 2015-02-11 2016-08-18 Dow Global Technologies Llc Adhésifs durcissables à basse température et leur utilisation
JP2016199739A (ja) * 2015-04-10 2016-12-01 株式会社カネカ 貯蔵安定性および接着性の改善されたポリマー微粒子含有硬化性樹脂組成物
WO2018030184A1 (fr) * 2016-08-10 2018-02-15 株式会社スリーボンド Composition de résine époxy, et adhésif conducteur contenant celle-ci

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