Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
  • C07D303/02—Compounds containing oxirane rings
  • C07D303/36—Compounds containing oxirane rings with hydrocarbon radicals, substituted by nitrogen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D301/00—Preparation of oxiranes
  • C07D301/27—Condensation of epihalohydrins or halohydrins with compounds containing active hydrogen atoms
• • 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
  • C08G59/02—Polycondensates containing more than one epoxy group per molecule
  • C08G59/10—Polycondensates containing more than one epoxy group per molecule of polyamines with epihalohydrins or precursors thereof
• • 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
  • C08G59/20—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 epoxy compounds used
  • C08G59/32—Epoxy compounds containing three or more epoxy groups
• • 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
  • C08G59/20—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 epoxy compounds used
  • C08G59/32—Epoxy compounds containing three or more epoxy groups
  • C08G59/3227—Compounds containing acyclic nitrogen atoms
• • 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
  • C08G59/20—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 epoxy compounds used
  • C08G59/32—Epoxy compounds containing three or more epoxy groups
  • C08G59/3254—Epoxy compounds containing three or more epoxy groups containing atoms other than carbon, hydrogen, oxygen or nitrogen
  • C08G59/329—Epoxy compounds containing three or more epoxy groups containing atoms other than carbon, hydrogen, oxygen or nitrogen containing halogen atoms
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
  • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
  • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
• • 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
  • C08K7/00—Use of ingredients characterised by shape
  • C08K7/02—Fibres or whiskers
• • 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
• • 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
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10W—GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
  • H10W74/00—Encapsulations, e.g. protective coatings
  • H10W74/10—Encapsulations, e.g. protective coatings characterised by their shape or disposition
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10W—GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
  • H10W74/00—Encapsulations, e.g. protective coatings
  • H10W74/40—Encapsulations, e.g. protective coatings characterised by their materials
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10W—GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
  • H10W74/00—Encapsulations, e.g. protective coatings
  • H10W74/40—Encapsulations, e.g. protective coatings characterised by their materials
  • H10W74/47—Encapsulations, e.g. protective coatings characterised by their materials comprising organic materials, e.g. plastics or resins
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
  • C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins

Definitions

• the present disclosure relates to an epoxy compound, an epoxy resin, an epoxy resin composition, a cured product, a prepreg, a fiber-reinforced composite material, a manufacturing method thereof, a sealing material, a semiconductor device, a method for sealing a semiconductor element, and a sealing material. Regarding how to use it as.
• an epoxy compound having a novel fluorine-containing skeleton an epoxy resin containing this epoxy compound, an epoxy resin composition containing this epoxy compound, a cured product obtained by curing this epoxy resin composition, A prepreg containing this epoxy resin composition, a method for sealing a semiconductor element using this epoxy resin composition and a method for using it as a sealing material, a fiber-reinforced composite material containing this cured product, a sealing material, and a semiconductor device.
• Fiber-reinforced composite materials (hereinafter sometimes referred to as FRP) containing reinforcing fibers and matrix resin have excellent mechanical properties such as strength and rigidity, so they are used in electrical and electronic equipment parts, aircraft parts, and spacecraft. Widely used as parts, automobile parts, railway vehicle parts, ship parts, and sports equipment parts. FRP is generally produced by various methods, and among these methods, it is widely practiced to use reinforcing fibers impregnated with an uncured matrix resin as a prepreg. In this method, stacked sheets of prepreg are heated to form a composite material. In most cases, epoxy resins have been used as matrix resins for prepregs, which have excellent properties such as heat resistance, dimensional stability, and chemical resistance.
• polyfunctional epoxy resins has been proposed so far for the purpose of improving the mechanical properties of the resin.
• a resin composition that uses diaminodiphenylsulfone as a curing agent and N,N,N',N'-tetraglycidyl-4,4'-diaminodiphenylmethane as a matrix resin, that is, contains a glycidylamine type epoxy compound. composition is used.
• An object of the present disclosure is to provide a glycidylamine type fluorine-containing epoxy compound.
• a further object of the present disclosure is to provide a fluorine-containing epoxy resin composition, a cured product, a prepreg, a fiber-reinforced composite material, a sealing material, and a semiconductor device that utilize the fluorine-containing epoxy compound.
• a fluorine-containing epoxy compound represented by general formula (1) [1] A fluorine-containing epoxy compound represented by general formula (1).
• n is each independently an integer of 0 to 4
• R 1 each independently represents a monovalent substituent, such as a halogen atom, an alkyl group, an alkoxy group, a haloalkoxy group, an aryl It is one selected from the group consisting of groups.
• n is each independently an integer of 0 to 4
• R 1 each independently represents a monovalent substituent, such as a halogen atom, an alkyl group, an alkoxy group, a haloalkoxy group, an aryl It is one selected from the group consisting of groups.
• a fluorine-containing epoxy resin composition comprising the fluorine-containing epoxy compound described in [1] to [2] or the fluorine-containing epoxy resin described in [3] and a curing agent.
• a prepreg comprising the fluorine-containing epoxy resin composition according to [4] impregnated into reinforcing fibers.
• a fiber-reinforced composite material comprising the cured product according to [5] and reinforcing fibers.
• a method for producing a fiber-reinforced composite material comprising impregnating the fluorine-containing epoxy resin composition according to [4] into reinforcing fibers and curing the reinforcing fibers.
• a sealing material comprising the cured product according to [5].
• a semiconductor device comprising at least a semiconductor element, the semiconductor element being sealed with the cured product according to [5].
• a method for producing a fluorine-containing epoxy compound represented by general formula (1) A method for producing a fluorine-containing epoxy compound, comprising a step of reacting an aromatic diamine compound represented by the general formula (1A) with an epihalohydrin.
• n is each independently an integer of 0 to 4
• R 1 each independently represents a monovalent substituent, such as a halogen atom, an alkyl group, an alkoxy group, a haloalkoxy group, an aryl It is one selected from the group consisting of groups.
• n is each independently an integer of 0 to 4
• R 1 is each independently a monovalent substituent, such as a halogen atom, an alkyl group, an alkoxy group, a haloalkoxy group, an aryl It is one selected from the group consisting of groups.
• Embodiments of the present disclosure provide a novel fluorine-containing epoxy compound. Further, embodiments of the present disclosure provide a fluorine-containing epoxy resin composition, a cured product, a prepreg, a fiber-reinforced composite material, a sealing material, and a semiconductor device using the fluorine-containing epoxy compound.
• alkyl group includes not only an alkyl group without a substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
• the fluorine-containing epoxy compound means the compound itself represented by each chemical formula.
• the fluorine-containing epoxy resin means a mixture containing the epoxy compound. That is, the fluorine-containing epoxy resin contains various by-products and unreacted substances during the production of the fluorine-containing epoxy compound.
• the fluorine-containing epoxy resin composition means an uncured or semi-cured composition containing at least a fluorine-containing epoxy compound and a curing agent for the fluorine-containing epoxy compound.
• a cured resin product (also referred to as a cured product) means a cured product obtained by a curing reaction of a fluorine-containing epoxy resin composition.
• the epoxy compound of the present disclosure is a fluorine-containing epoxy compound represented by general formula (1).
• This fluorine-containing epoxy compound has a 1,1,1-trifluoro-2,2-ethanediyl group (representing a -C(CF 3 )H- group) and a diglycidylamino group in at least one aromatic ring. It is characterized by having a structure that The present inventors believe that the heat resistance and dimensional stability of the cured resin are high due to the unique three-dimensional structure of the cured resin resulting from the asymmetric structure of the 1,1,1-trifluoro-2,2-ethanediyl group. have estimated that.
• the present inventors also estimate that curing can be performed in a shorter time due to the asymmetric structure of the 1,1,1-trifluoro-2,2-ethanediyl group.
• the fluorine-containing epoxy compound represented by the general formula (1) is characterized by the asymmetric structure of the 1,1,1-trifluoro-2,2-ethanediyl group, so the position of the substituent, R 1 Regardless of the type or number of resins, a cured resin product with excellent heat resistance and dimensional stability can be obtained, and it can be cured in a shorter time.
• n is each independently an integer of 0 to 4
• R 1 each independently represents a monovalent substituent, such as a halogen atom, an alkyl group, an alkoxy group, a haloalkoxy group, an aryl It is one selected from the group consisting of groups.
• n is preferably 0 to 3, more preferably 0 to 2, and even more preferably 0 to 1.
• the halogen atom for R 1 is not limited, but is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
• the alkyl group for R 1 is not limited, but is preferably a linear or branched alkyl group having 1 to 6 carbon atoms (preferably 1 to 3 carbon atoms), and among them, n-butyl group, s-butyl group, isobutyl group, Preferred are t-butyl, n-propyl, i-propyl, ethyl and methyl groups, with ethyl and methyl groups being particularly preferred.
• the alkoxy group for R 1 is not limited, it is preferably a linear or branched alkoxy group having 1 to 6 carbon atoms, and among them, n-butoxy group, s-butoxy group, isobutoxy group, t-butoxy group, n- Propoxy, i-propoxy, ethoxy and methoxy groups are preferred, with ethoxy and methoxy groups being particularly preferred.
• the alkyl group or alkoxy group of R 1 may be substituted on any carbon thereof with, for example, a halogen atom, an alkoxy group, or a haloalkoxy group in any number and in any combination. It is preferable that the alkyl group or alkoxy group of R 1 has no substituent.
• the number of R 1 in general formula (1) is two or more, two or more R 1 are connected to form a saturated or unsaturated, monocyclic or polycyclic ring having 3 to 10 carbon atoms. may form a cyclic group.
• haloalkoxy group for R 1 is not limited, but difluoromethoxy, trifluoromethoxy, tetrafluoroethoxy and 2,2,2-trifluoroethoxy groups are preferred, particularly trifluoromethoxy and 2,2,2- Trifluoroethoxy group is preferred.
• the aryl group for R 1 is not limited, but phenyl, tolyl, xylyl, 1-naphthyl and 2-naphthyl groups are preferred, with phenyl being particularly preferred.
• R 1 is preferably a linear or branched alkyl group having 1 to 6 carbon atoms. Moreover, when the number of R 1 in general formula (1) is two or more, it is also preferable that all R 1 are the same group.
• the fluorine-containing epoxy compound represented by the general formula (1) it is symmetrical about the 1,1,1-trifluoro-2,2-ethanediyl group (representing a -C(CF 3 )H- group) as an axis. It is also preferable. Specifically, the aromatic ring located on the right side of the 1,1,1-trifluoro-2,2-ethanediyl group (representing a -C(CF 3 )H- group) in general formula (1) and the aromatic ring located on the left side It is preferable that the types and number of substituents and the positions of the substituents in the aromatic rings are the same (left-right symmetry).
• a fluorine-containing epoxy compound represented by the following general formula (2) is particularly preferred.
• n is each independently an integer of 0 to 4
• R 1 each independently represents a monovalent substituent, such as a halogen atom, an alkyl group, an alkoxy group, a haloalkoxy group, an aryl It is one selected from the group consisting of groups.
• n and R 1 in general formula (2) are the same as n and R 1 in general formula (1), including preferred embodiments.
• the compound whose position having the diglycidylamino group has been specified corresponds to the compound represented by the general formula (2).
• the compound is the same as the compound represented by general formula (1), including preferred embodiments, except for the position where the diglycidylamino group is present.
• the fluorine-containing epoxy compound of the present disclosure preferably has a viscosity at 150°C of less than 200 mPa ⁇ s, more preferably less than 150 mPa ⁇ s, and preferably less than 100 mPa ⁇ s at 150°C from the viewpoint of fast curing properties. is particularly preferred, and the lower limit is not particularly limited. In this specification, the viscosity of an epoxy compound at 150°C is measured by the method described in Examples.
• fluorine-containing epoxy compounds include the following compounds. Among them, 1,1,1-trifluoro-2,2-bis(4-diglycidylaminophenyl)ethane represented by the general formula (3), 1,1 represented by the general formula (4) , 1-trifluoro-2,2-bis(3-methyl-4-diglycidylaminophenyl)ethane is preferred.
• the above-mentioned fluorine-containing epoxy compound may be synthesized by any method, but for example, it may be synthesized by reacting a fluorine-containing aromatic diamine compound represented by the following general formula (1A) with an epihalohydrin such as epichlorohydrin. After obtaining a tetrahalohydrin compound, a cyclization reaction is performed using an alkaline compound.
• a fluorine-containing aromatic diamine compound represented by the following general formula (1A) with an epihalohydrin such as epichlorohydrin. After obtaining a tetrahalohydrin compound, a cyclization reaction is performed using an alkaline compound.
• n is each independently an integer of 0 to 4
• R 1 is each independently a monovalent substituent, such as a halogen atom, an alkyl group, an alkoxy group, a haloalkoxy group, an aryl It is one selected from the group consisting of groups.
• n and R 1 in general formula (1A) are the same as n and R 1 in general formula (1), including preferred embodiments.
• a fluorine-containing aromatic diamine compound represented by the following general formula (2A) is particularly preferred.
• n is each independently an integer of 0 to 4, and each R 1 independently represents a monovalent substituent, such as a halogen atom, an alkyl group, an alkoxy group, a haloalkoxy group, an aryl It is one selected from the group consisting of groups.
• n and R 1 in general formula (2A) are the same as n and R 1 in general formula (1), including preferred embodiments.
• the fluorine-containing aromatic diamine compound represented by the general formula (2A) can be produced, for example, with reference to the method described in WO2020-162411.
• compounds that are particularly preferably used in terms of performance and cost are shown below.
• the amount of epihalohydrin (typically epichlorohydrin or epibromohydrin) used in the reaction is preferably 0.1 per mol of amino group of the fluorine-containing aromatic diamine represented by general formula (2A). -100 mol, more preferably 1.0-75 mol, still more preferably 2.0-50 mol.
• the base used in the reaction usually includes alkali metal hydroxides, alkali metal alkoxides, alkali metal carbonates, and the like.
• a preferred embodiment of the reaction is to bring the reaction system under "alkaline conditions" by adding an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide as a base to the reaction system in the form of a solid or aqueous solution. .
• the amount of the base added is preferably 0.1 to 100 mol, more preferably 2.0 to 50 mol, per mol of amino group of the fluorine-containing aromatic diamine represented by general formula (2A).
• the reaction can be carried out under normal pressure (0.1 MPa; absolute pressure) or under reduced pressure.
• the reaction temperature is usually 20 to 150°C in the case of reaction under normal pressure, and 30 to 80°C in case of reaction under reduced pressure.
• the reaction solution is azeotropically distilled while maintaining a predetermined temperature as necessary, and the evaporated vapor is cooled to separate the organic phase/aqueous phase of the resulting condensate, and the aqueous phase is removed.
• the organic phase is dehydrated by returning it to the reaction system.
• the alkali metal hydroxide in order to suppress rapid reaction, the alkali metal hydroxide is usually added to the reaction system intermittently or continuously in small amounts over 0.1 to 10 hours.
• the total reaction time is usually 1 to 15 hours.
• an analytical instrument such as a nuclear magnetic resonance apparatus (NMR) or liquid chromatography (LC), and to set the end point of the reaction as soon as it is confirmed that the reaction conversion rate has reached a predetermined value. .
• quaternary ammonium salts such as tetrabutylammonium hydrogen sulfate, tetramethylammonium chloride, and tetraethylammonium bromide; tertiary amines such as benzyldimethylamine and 2,4,6-tris(dimethylaminomethyl)phenol; Catalysts such as imidazoles such as 2-ethyl-4-methylimidazole and 2-phenylimidazole; phosphonium salts such as ethyltriphenylphosphonium iodide; and phosphines such as triphenylphosphine may be used.
• quaternary ammonium salts such as tetrabutylammonium hydrogen sulfate, tetramethylammonium chloride, and tetraethylammonium bromide
• tertiary amines such as benzyldimethylamine and 2,4,6
• alcohols such as ethanol and isopropyl alcohol; ketones such as acetone and methyl ethyl ketone; ethers such as dioxane and ethylene glycol dimethyl ether; glycol ethers such as methoxypropanol; aprotons such as dimethyl sulfoxide and dimethyl formamide
• Inert organic solvents such as polar solvents may also be used. These organic solvents may be used alone or in combination of two or more.
• the fluorine-containing epoxy compound of the present disclosure has the advantage that it can be produced with a good yield and has fewer by-products and unreacted substances compared to known fluorine-containing epoxy compounds that are not within the scope of the present disclosure.
• the reason for this is that the fluorine-containing aromatic diamine compound represented by the general formula (2A) contains an asymmetric (-C(CF 3 )H- group), thereby suppressing excessive rigidity; This is presumed to be due to the moderate content of fluorine atoms.
• the fluorine-containing epoxy compound represented by the above general formula (1) or (2) does not necessarily need to be isolated after synthesis, and the fluorine-containing epoxy compound represented by the above general formula (1) or (2) is not necessarily isolated during the production of the fluorine-containing epoxy compound represented by the above general formula (1) or (2). It may also be used as a fluorine-containing epoxy resin containing by-products and unreacted substances.
• the fluorine-containing epoxy resin of the present disclosure is a fluorine-containing epoxy resin containing a fluorine-containing epoxy compound represented by the general formula (1) in an area ratio of 50% or more as measured by high performance liquid chromatography (HPLC). .
• the fluorine-containing epoxy resin of the present disclosure preferably contains the fluorine-containing epoxy compound represented by the general formula (1) in an area ratio of 60% or more in HPLC measurement, and preferably contains 70% or more. More preferred. By containing it in a proportion of 50% or more, heat resistance and mechanical strength can be increased. Further, the fluorine-containing epoxy resin of the present disclosure preferably contains the fluorine-containing epoxy compound represented by the general formula (1) in an area ratio of 99.99% or less in HPLC measurement. In this specification, the area ratio of the fluorine-containing epoxy compound represented by the general formula (1) in the HPLC measurement of the fluorine-containing epoxy resin is measured by the method described in Examples.
• the fluorine-containing epoxy resin of the present disclosure preferably has a viscosity at 150°C of less than 200 mPa ⁇ s, more preferably less than 150 mPa ⁇ s, and preferably less than 100 mPa ⁇ s at 150°C from the viewpoint of fast curing properties. is particularly preferred, and the lower limit is not particularly limited. In this specification, the viscosity of the fluorine-containing epoxy resin at 150°C is measured by the method described in Examples.
• the fluorine-containing epoxy resin composition of the present disclosure is an uncured or semi-cured composition comprising at least the fluorine-containing epoxy compound of the present disclosure and a curing agent.
• the fluorine-containing epoxy resin composition of the present disclosure may also contain a thermosetting resin, a thermoplastic resin, and other additives. Further, the fluorine-containing epoxy resin composition of the present disclosure only needs to contain both the fluorine-containing epoxy compound and the curing agent when being cured.
• a composition containing a fluorine-containing epoxy compound and a curing agent may be prepared in advance, or a composition containing a fluorine-containing epoxy compound and a composition containing a curing agent may be separately prepared and, for example, molded into a mold. You may also mix it inside.
• the fluorine-containing epoxy compound contained in the fluorine-containing epoxy resin composition of the present disclosure may be a fluorine-containing epoxy resin containing impurities.
• the fluorine-containing epoxy compound of the present disclosure and the fluorine-containing epoxy resin of the present disclosure may be used alone, or two or more types may be used in combination.
• the viscosity of the fluorine-containing epoxy resin composition of the present disclosure may be adjusted as appropriate depending on the molding method, but for example, when used as a prepreg, the viscosity at 150°C is preferably less than 2000 mPa ⁇ s, and 0.001 More preferably, it is 1000 mPa ⁇ s. If it exceeds 2000 mPa ⁇ s, the handling properties may deteriorate. Moreover, when a prepreg is produced using a fluorine-containing epoxy resin composition having a viscosity of more than 2000 mPa ⁇ s at 150° C., unimpregnated portions are likely to occur in the prepreg. As a result, voids and the like are likely to be formed in the fiber-reinforced composite material obtained. In this specification, the viscosity at 150° C. of the fluorine-containing epoxy resin composition is measured by the method described in Examples.
• the content of the fluorine-containing epoxy compound represented by the general formula (1) (fluorine-containing epoxy resin of the present disclosure) in the fluorine-containing epoxy resin composition of the present disclosure is preferably 10 to 90% by mass, It is more preferably 15 to 80% by mass, and even more preferably 20 to 70% by mass.
• the amount is less than 10% by mass, the handleability of the resin composition may be deteriorated, and the strength and heat resistance of the resulting cured product may be reduced.
• the amount is more than 90% by mass, the molar balance with the curing agent becomes inappropriate, and various properties such as mechanical properties of the cured product may deteriorate.
• the curing agent used in the fluorine-containing epoxy resin composition of the present disclosure is not particularly limited, and is a known curing agent for curing epoxy resins.
• the curing agent may be any substance that cures the epoxy resin, and is appropriately selected depending on the purpose of use.
• amine curing agents are suitable for curing epoxy resin compositions.
• Amine curing agents are compounds that have at least one nitrogen atom in the molecule and can react with epoxy groups in epoxy resins for curing.
• a suitable type of amine curing agent is, for example, diaminodiphenylsulfone.
• diaminodiphenylsulfones include, but are not limited to, 4,4'-diaminodiphenylsulfone (4,4'-DDS), and 3,3'-diaminodiphenylsulfone (3,3'-DDS). , and combinations thereof.
• the curing agent may be used alone or in combination of two or more.
• the amount of curing agent contained in the fluorine-containing epoxy resin composition is an amount suitable for curing all the epoxy resins blended in the fluorine-containing epoxy resin composition, and it depends on the type of epoxy resin and curing agent used. Adjustments will be made accordingly. For example, when an amine curing agent is used, it is preferably 25 to 65 parts by weight, more preferably 35 to 55 parts by weight, based on 100 parts by weight of the total epoxy resin. When the amount is less than 25 parts by mass or more than 65 parts by mass, the fluorine-containing epoxy resin composition may not be sufficiently cured, and the physical properties of the cured resin may tend to deteriorate.
• the fluorine-containing epoxy resin composition of the present disclosure essentially contains the above-described fluorine-containing epoxy compound and its curing agent, but may contain other components. Other components may be used alone or in combination of two or more.
• the fluorine-containing epoxy resin composition of the present disclosure essentially contains the fluorine-containing epoxy compound represented by the above general formula (1), but may also contain other epoxy resins other than the fluorine-containing epoxy compound of the present disclosure. .
• epoxy resins conventionally known epoxy resins can be used. Specifically, an epoxy resin containing an aromatic group is preferable, and an epoxy resin containing either a glycidyl amine structure or a glycidyl ether structure is preferable. Furthermore, alicyclic epoxy resins can also be suitably used.
• the fluorine-containing epoxy compound represented by general formula (1) and another epoxy resin are used together, the fluorine-containing epoxy compound represented by general formula (1) accounts for all the epoxy resins contained in the fluorine-containing epoxy resin composition.
• the content ratio is preferably 20% by mass or more, more preferably 50% by mass or more, and even more preferably 60 to 100% by mass.
• Epoxy resins containing a glycidylamine structure include tetraglycidyldiaminodiphenylmethane, N,N,O-triglycidyl-p-aminophenol, N,N,O-triglycidyl-m-aminophenol, N,N,O- Examples include triglycidyl-3-methyl-4-aminophenol and various isomers of triglycidylaminocresol.
• examples of epoxy resins containing a glycidyl ether structure include bisphenol A epoxy resins, bisphenol F epoxy resins, bisphenol S epoxy resins, phenol novolac epoxy resins, and cresol novolak epoxy resins.
• these epoxy resins may have a non-reactive substituent in the aromatic ring structure or alicyclic structure, if necessary.
• non-reactive substituents include alkyl groups such as methyl, ethyl, and isopropyl, aromatic groups such as phenyl, alkoxy groups, aralkyl groups, and halogen groups such as fluorine, chlorine, and bromine.
• the fluorine-containing epoxy resin composition of the present disclosure may contain a thermoplastic resin.
• the thermoplastic resin include epoxy resin-soluble thermoplastic resins and epoxy resin-insoluble thermoplastic resins.
• An epoxy resin-soluble thermoplastic resin is a thermoplastic resin that can be partially or completely dissolved in an epoxy resin at a temperature at or below the temperature at which FRP is molded.
• an epoxy resin-insoluble thermoplastic resin refers to a thermoplastic resin that does not substantially dissolve in an epoxy resin at a temperature at or below the temperature at which FRP is molded.
• the epoxy resin-soluble thermoplastic resin examples include polyether sulfone, polysulfone, polyetherimide, polycarbonate, and the like. These may be used alone or in combination of two or more. Such an epoxy resin-soluble thermoplastic resin can improve the dissolution stability during the curing process of the epoxy resin. Moreover, toughness, chemical resistance, heat resistance, and heat-and-moisture resistance can be imparted to the FRP obtained after curing.
• epoxy resin-insoluble thermoplastic resin examples include polyamide, polyacetal, polyphenylene oxide, polyphenylene sulfide, polyester, polyamideimide, polyimide, polyether ketone, polyether ether ketone, polyethylene naphthalate, polyether nitrile, and polybenzimidazole. .
• polyamide, polyamideimide, and polyimide are particularly preferred because they have high toughness and heat resistance.
• Polyamide and polyimide have an excellent toughness improving effect on cured resins. These may be used alone or in combination of two or more. Moreover, these copolymers can also be used.
• thermoplastic resins contained in the epoxy resin composition is appropriately adjusted depending on the viscosity. From the viewpoint of processability of the prepreg, it is preferably 5 to 60 parts by mass, more preferably 10 to 50 parts by mass, and even more preferably 20 to 40 parts by mass, based on 100 parts by mass of the epoxy resin contained in the epoxy resin composition. . If the amount is less than 5 parts by mass, the resulting FRP may have insufficient impact resistance. When the content of these thermoplastic resins becomes high, the viscosity becomes significantly high, and the handleability of the prepreg may be significantly deteriorated.
• the fluorine-containing epoxy resin composition of the present disclosure may contain conductive particles, a flame retardant, an inorganic filler, and an internal mold release agent.
• conductive particles include conductive polymer particles such as polyacetylene particles, polyaniline particles, polypyrrole particles, polythiophene particles, polyisothianaphthene particles, and polyethylenedioxythiophene particles; carbon particles; carbon fiber particles; metal particles; inorganic materials or organic Examples include particles in which a core material made of a material is coated with a conductive substance.
• flame retardants include phosphorus-based flame retardants.
• Phosphorus-based flame retardants are not particularly limited as long as they contain phosphorus atoms in their molecules, and examples include organic phosphorus compounds such as phosphoric acid esters, condensed phosphoric acid esters, phosphazene compounds, polyphosphates, and red phosphorus. It will be done.
• organic phosphorus compounds such as phosphoric acid esters, condensed phosphoric acid esters, phosphazene compounds, polyphosphates, and red phosphorus. It will be done.
• inorganic fillers include aluminum borate, calcium carbonate, silicon carbonate, silicon nitride, potassium titanate, basic magnesium sulfate, zinc oxide, graphite, calcium sulfate, magnesium borate, magnesium oxide, and silicate minerals. can be mentioned. In particular, it is preferable to use silicate minerals.
• the internal mold release agent include metal soaps, vegetable waxes such as polyethylene wax and carnauba wax, fatty acid ester mold release agents, silicone oil, animal wax,
• the method for producing the fluorine-containing epoxy resin composition is not particularly limited, and any conventionally known method may be used.
• An example of the mixing temperature is a range of 40 to 150°C. If the temperature exceeds 150°C, the curing reaction may partially proceed, impregnating into the reinforcing fiber base layer may decrease, and the storage stability of the resulting fluorine-containing epoxy resin composition and the prepreg produced using it may deteriorate. Sexuality may decrease. If the temperature is less than 40°C, the viscosity of the epoxy resin composition may be high and mixing may become substantially difficult. Preferably it is in the range of 50 to 120°C.
• mixing machine conventionally known ones can be used. Specific examples include a roll mill, a planetary mixer, a kneader, an extruder, a Banbury mixer, a mixing container equipped with stirring blades, a horizontal mixing tank, and the like. Mixing of each component can be performed in the air or under an inert gas atmosphere. When mixing is performed in the atmosphere, an atmosphere with controlled temperature and humidity is preferred. Although not particularly limited, it is preferable, for example, to mix at a temperature controlled at a constant temperature of 30° C. or lower, or in a low humidity atmosphere with a relative humidity of 50% RH or lower.
• the cured product of the present disclosure is a cured product obtained by curing the fluorine-containing epoxy resin composition of the present disclosure.
• the curing reaction is appropriately determined depending on the epoxy resin, curing agent, etc. contained in the epoxy resin composition, but is usually carried out by heating at 20 to 250° C. for 0.07 hours or more. Although the heating time is preferably within 0.13 hours, the usual heating time is 0.5 hours or more.
• the cured product of the present disclosure is characterized in that it can be cured in a short time. Although the reason for this is not necessarily clear, it is assumed that the asymmetric structure of the 1,1,1-trifluoro-2,2-ethanediyl group is probably involved.
• the cured product of the present disclosure is characterized by high heat resistance.
• heat resistance can be determined from the glass transition temperature of each cured product.
• the glass transition temperature of the cured product of the present disclosure is preferably 180°C or higher, more preferably 200°C or higher, even more preferably 220°C or higher, and particularly preferably 230°C or higher.
• the upper limit of the glass transition temperature is not particularly limited, but is usually less than 300°C. In this specification, the glass transition temperature of the cured product is measured by the method described in Examples.
• the cured product of the present disclosure is characterized by high dimensional stability.
• dimensional stability can be determined from the coefficient of linear expansion at each temperature.
• the linear expansion coefficient ⁇ 1 of the cured product of the present disclosure at 25 to 180° C. below the glass transition temperature is preferably 120 ppm/°C or less, more preferably 80 ppm/°C or less.
• the linear expansion coefficient ⁇ 2 at 180 to 300° C. above the glass transition temperature is preferably 200 ppm/°C or less, more preferably 160 ppm/°C or less, and even more preferably 130 ppm/°C or less.
• the lower limit of the coefficient of linear expansion at each temperature is not particularly limited, but is usually 20 ppm/°C or more. In this specification, the linear expansion coefficient of the cured product is measured by the method described in Examples.
• the cured product of the present disclosure is characterized by low water absorption.
• the water absorption rate refers to the mass increase rate after storage at 25° C. in water for 72 hours.
• the water absorption rate is preferably less than 3.0% by mass, more preferably less than 1.0% by mass, and even more preferably less than 0.5% by mass.
• the lower limit of the water absorption rate is not particularly limited, but is usually 0.01% by mass or more.
• the strength of the cured resin molded into a thin plate may be particularly likely to decrease.
• the water absorption rate of the cured product is measured by the method described in Examples.
• the prepreg of the present disclosure is made of reinforcing fibers impregnated with the fluorine-containing epoxy resin composition of the present disclosure. That is, the prepreg of the present disclosure is a prepreg in which reinforcing fibers are partially or entirely impregnated with the fluorine-containing epoxy resin composition.
• the content of the fluorine-containing epoxy resin composition in the entire prepreg is preferably 15 to 60% by mass based on the total mass of the prepreg. If the content of the fluorine-containing epoxy resin composition is less than 15% by mass, voids may occur in the resulting fiber-reinforced composite material, which may deteriorate mechanical properties. When the content of the fluorine-containing epoxy resin composition exceeds 60% by mass, the reinforcing effect of the reinforcing fibers of the obtained fiber-reinforced composite material may be insufficient, and the mechanical properties may be substantially low.
• the reinforcing fibers may be twisted yarns, untwisted yarns, or non-twisted yarns, but untwisted yarns and non-twisted yarns are preferable because they have excellent moldability in fiber-reinforced composite materials.
• the reinforcing fibers can be in the form of fibers whose fibers are aligned in one direction or a woven fabric. Fabrics can be freely selected from plain weave, satin weave, etc. depending on the part and purpose of use. Specifically, carbon fibers, glass fibers, aramid fibers, boron fibers, alumina fibers, silicon carbide fibers, etc. can be used because they have excellent mechanical strength and durability, and two or more of these can also be used in combination. . Among these, carbon fibers are particularly preferred since they provide good strength to the molded product, and various carbon fibers such as polyacrylonitrile, pitch, and rayon fibers can be used.
• the method for producing the prepreg of the present disclosure is not particularly limited as long as the fluorine-containing epoxy resin composition of the present disclosure is impregnated into reinforcing fibers, and any conventionally known method may be employed. Specifically, a hot melt method or a solvent method can be suitably employed.
• a resin composition film is formed by coating a resin composition in a thin film form on release paper, and the resin composition film is laminated on reinforcing fibers and heated under pressure to form an epoxy resin.
• the solvent method is a method in which an epoxy resin composition is made into a varnish using a suitable solvent, and the reinforcing fibers are impregnated with this varnish.
• the fiber-reinforced composite material of the present disclosure includes the cured product of the present disclosure and reinforcing fibers.
• the fiber-reinforced composite material is produced by curing reinforcing fibers and the fluorine-containing epoxy resin composition of the present disclosure in a composite state.
• the total content of the cured product and reinforcing fibers of the present disclosure in the fiber-reinforced composite material of the present disclosure is preferably 60% by mass or more, more preferably 80% by mass or more, and more preferably 90% by mass or more. It is more preferably 95% by mass or more, and may be 100% by mass.
• the method for obtaining a fiber-reinforced composite material using the fluorine-containing epoxy resin composition of the present disclosure is not particularly limited, but for example, a varnish may be produced by uniformly mixing each component constituting the fluorine-containing epoxy resin composition. Then, unidirectional reinforcing fibers, in which reinforcing fibers are aligned in one direction, are immersed in the obtained varnish (before curing by pultrusion method or filament winding method), or woven reinforcing fibers are layered to create a concave shape. Examples include a method in which the resin is set in a mold, and then sealed with a convex mold, and then injected with a resin and impregnated with pressure (in a state before curing by the RTM method).
• the fluorine-containing epoxy resin composition does not necessarily have to be impregnated into the inside of the fiber bundle, and the fluorine-containing epoxy resin composition is localized near the surface of the fibers. It may be.
• methods for manufacturing FRP using a prepreg in which reinforcing fibers and an epoxy resin composition are composited in advance include known molding methods such as autoclave molding and press molding.
• the method for manufacturing FRP of the present disclosure is not particularly limited as long as it is characterized by curing the prepreg of the present disclosure or impregnating the fluorine-containing epoxy resin composition of the present disclosure into reinforcing fibers and curing it. Any known method can be used.
• an autoclave molding method is preferably used.
• a prepreg and a film bag are sequentially placed in the lower mold of a mold, the prepreg is sealed between the lower mold and the film bag, and the space formed by the lower mold and the film bag is evacuated.
• this is a molding method that uses an autoclave molding device to heat and pressurize.
• the conditions during molding are preferably a heating rate of 1 to 50° C./min, heating and pressurization at 0.2 to 0.8 MPa and 100 to 180° C. for 30 to 300 minutes.
• a press molding method is preferably used.
• FRP is manufactured by the press molding method by heating and pressing the prepreg of the present disclosure or a preform formed by laminating the prepregs of the present disclosure using a mold.
• the mold is preferably heated to a curing temperature in advance.
• the temperature of the mold during press molding is preferably 150 to 200°C.
• the molding temperature is 150° C. or higher, a curing reaction can be sufficiently caused and FRP can be obtained with high productivity.
• the molding temperature is 200° C. or lower, the resin viscosity will not become too low, and excessive flow of the resin within the mold can be suppressed.
• the pressure during molding is 0.05 to 2 MPa, preferably 0.2 to 2 MPa.
• the pressure is 0.05 MPa or more, appropriate flow of the resin can be obtained, and poor appearance and generation of voids can be prevented.
• the prepreg sufficiently adheres to the mold, it is possible to manufacture FRP with a good appearance. If the pressure is 2 MPa or less, the resin will not be made to flow more than necessary, so that the resulting FRP will be less likely to have poor appearance. Furthermore, since no more load than necessary is applied to the mold, deformation of the mold is less likely to occur.
• the molding time is preferably 1 to 8 hours.
• the sealing material of the present disclosure includes the cured product of the present disclosure.
• the sealing material of the present disclosure is produced by curing the fluorine-containing epoxy resin composition of the present disclosure.
• the encapsulant of the present disclosure can be used as a encapsulant for semiconductors and light emitting diodes (LEDs), and is especially suitable for use as a encapsulant for semiconductors.
• the cured product of the present disclosure exhibits high heat resistance, it can also be applied as a sealing material for power semiconductors.
• the content of the cured product of the present disclosure in the sealing material of the present disclosure is preferably 60% by mass or more, more preferably 80% by mass or more, even more preferably 90% by mass or more, It is particularly preferably 95% by mass or more, and may be 100% by mass.
• the semiconductor device of the present disclosure is a semiconductor device including at least a semiconductor element, and the semiconductor device is at least sealed with a cured product of the fluorine-containing epoxy resin composition of the present disclosure.
• Other configurations of the semiconductor device of the present disclosure are not particularly limited, and may include conventionally known semiconductor device members in addition to the semiconductor element. Examples of such semiconductor device members include base substrates, lead wiring, wire wiring, control elements, insulating substrates, heat sinks, conductive members, die bonding materials, bonding pads, and the like.
• a part or all of the semiconductor device member may be sealed with a cured product of the fluorine-containing epoxy resin composition of the present disclosure.
• An example of the semiconductor device of the present disclosure includes, for example, the semiconductor device shown in FIG. 1 of Japanese Patent Application Publication No. 2017-197591. Note that the structure shown in FIG. 1 of JP-A-2017-197591 is only an example of the semiconductor device of the present disclosure, and the structure of the frame, the mounting structure of the semiconductor element, etc. may be modified as appropriate, and the structure shown in FIG. Additional members may be added as appropriate.
• the semiconductor device of the present disclosure is manufactured by, for example, molding the fluorine-containing epoxy resin composition of the present disclosure by a cast molding method, compression molding method, or transfer molding method and sealing a semiconductor element with a cured product obtained. be able to.
• the glass transition temperature (Tg) of each cured product was measured using a differential scanning calorimeter.
• the glass transition temperature was measured using a differential scanning calorimeter (manufactured by Hitachi High-Tech Science, model name: DSC7000) at a heating rate of 10° C./min.
• CTE coefficient of linear expansion
• the water absorption rate was calculated with reference to the method described in JIS K7209:2000.
• the mass W1 of a sample piece with a size of 4 mm x 10 mm x 80 mm was measured, and it was dried in a constant temperature bath at 60° C. for 24 hours. After drying, the temperature was returned to room temperature in a desiccator, and the mass W2 was measured. When the difference between W1 and W2 was 0.5 mg or more, drying was performed again and repeated until the difference became smaller than 0.5 mg. When the mass change was less than 0.5 mg, the sample piece was submerged in 1 L or more of water, left to stand in a constant temperature bath at 25° C.
• the curability of the epoxy compound was measured by the curing rate.
• 3 g of an epoxy resin composition prepared from each epoxy compound and a curing agent (4,4-DDS) was weighed into a glass vial equipped with a Teflon (registered trademark) stirring bar, and stirred at 180°C. The time until stirring was stopped due to an increase in the viscosity of the epoxy resin composition was measured.
• 1,1,1-trifluoro-2,2-bis(4- 40 g (0.15 mol) of aminophenyl)ethane and 167 g (1.8 mol) of epichlorohydrin were added, and the mixture was stirred at 80° C. for 18 hours. After stirring, unreacted epichlorohydrin was distilled off, 120 g of methyl isobutyl ketone, 1.2 g (0.0045 mol) of tetrabutylammonium hydrogen sulfate were added, and 180 g (0.9 mol) of a 20% aqueous sodium hydroxide solution was added. The mixture was added dropwise at 60°C over 2 hours. After the dropwise addition was completed, the mixture was stirred at 60° C.
• 1,1,1-trifluoro-2,2-bis(3- 44 g (0.15 mol) of methyl-4-aminophenyl)ethane and 167 g (1.8 mol) of epichlorohydrin were added, and the mixture was stirred at 80° C. for 18 hours. After stirring, unreacted epichlorohydrin was distilled off, 120 g of methyl isobutyl ketone, 1.2 g (0.0045 mol) of tetrabutylammonium hydrogen sulfate were added, and 180 g (0.9 mol) of a 20% aqueous sodium hydroxide solution was added. The mixture was added dropwise at 60°C over 2 hours.
• the mixture was added dropwise at 60°C over 2 hours. After the dropwise addition was completed, the mixture was stirred at 60° C. for 3 hours, and it was confirmed by liquid chromatography that the ring-closing reaction had proceeded.
• the organic layer was separated using a separatory funnel, and the obtained organic layer was washed twice with 120 g of water. The organic layer obtained by washing was concentrated using a rotary evaporator to obtain 61 g of the epoxy resin (yield 26%).
• Synthesis Examples 1 to 4 Synthesis Examples 1 to 2 in which the fluorine-containing epoxy compounds of the present disclosure were produced, compared to Synthesis Examples 3 to 4 in which fluorine-containing epoxy compounds that were not within the scope of the present disclosure were produced, It was revealed that the yield was high and the amount of by-products and unreacted substances was significantly lower.
• Examples 1-2, Comparative Examples 1-3 4,4-DDS was weighed into a glass beaker and melted in advance in an oven at 160°C.
• the epoxy resin in the mass parts listed in Table 2 was added thereto, and the mixture was stirred until a homogeneous solution was obtained. After defoaming in vacuum for 20 minutes, the mixture was poured into a preheated silicone mold and cured at 180° C. for 2 hours under normal pressure. The obtained cured product was shaped using a diamond wheel saw and subjected to physical property measurements.
• a cured product When a cured product is produced using the disclosed fluorine-containing epoxy compound, it has the advantage of being able to be cured in a shorter time and being easier to handle. Moreover, these cured products have excellent heat resistance and dimensional stability compared to the comparative examples.
• Resin is in demand.
• it is necessary to suppress the occurrence of cracks due to stress relaxation during thermosetting, and one method for this is to match the linear expansion coefficient of the resin composition with that of the substrate.
• the coefficient of linear expansion of epoxy resins is larger than that of metal substrates, so it is desired to develop epoxy resins with lower coefficients of linear expansion and excellent dimensional stability. It can be said that the utility value of epoxy resin is extremely high.
• a cured product using the glycidylamine type fluorine-containing epoxy compound of the present disclosure can be cured in a short time. Further, cured products using the glycidylamine type fluorine-containing epoxy compound of one embodiment of the present disclosure, such as Examples 1 and 2, have excellent heat resistance and dimensional stability. Therefore, it has very high utility value in fiber-reinforced composite materials and sealing materials, and is suitable for, for example, manufacturing electrical and electronic equipment parts, aircraft parts, spacecraft parts, automobile parts, railway vehicle parts, ship parts, and sports equipment parts. It can be used for.

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• 2023
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