WO2021157624A1 - 光湿気硬化性樹脂組成物、電子部品用接着剤、電子部品の製造方法及び硬化体 - Google Patents

光湿気硬化性樹脂組成物、電子部品用接着剤、電子部品の製造方法及び硬化体 Download PDF

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WO2021157624A1
WO2021157624A1 PCT/JP2021/003989 JP2021003989W WO2021157624A1 WO 2021157624 A1 WO2021157624 A1 WO 2021157624A1 JP 2021003989 W JP2021003989 W JP 2021003989W WO 2021157624 A1 WO2021157624 A1 WO 2021157624A1
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moisture
resin composition
meth
curable resin
acrylate
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PCT/JP2021/003989
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English (en)
French (fr)
Japanese (ja)
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典希 冨田
彰 結城
拓身 木田
智一 玉川
坤 徐
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積水化学工業株式会社
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Priority to CN202180005424.5A priority Critical patent/CN114423834A/zh
Priority to JP2021514450A priority patent/JPWO2021157624A1/ja
Priority to KR1020227008921A priority patent/KR20220137865A/ko
Publication of WO2021157624A1 publication Critical patent/WO2021157624A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/067—Polyurethanes; Polyureas
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/04—Non-macromolecular additives inorganic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/08—Macromolecular additives
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/06—Polyurethanes from polyesters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/08—Polyurethanes from polyethers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers

Definitions

  • the present invention relates to a thermosetting resin composition, an adhesive for electronic parts, a method for manufacturing an electronic component using an adhesive for electronic components, and a cured product of a thermosetting resin composition.
  • liquid crystal display elements In recent years, liquid crystal display elements, organic EL display elements, and the like have been widely used as display elements having features such as thinness, light weight, and low power consumption.
  • a photocurable resin composition is usually used for sealing a liquid crystal or a light emitting layer, adhering various members such as a substrate, an optical film, and a protective film.
  • miniaturization of display elements is the most sought after issue, and as a method of miniaturization, the image display unit is narrowed. It is being made into a frame (hereinafter, also referred to as a narrow frame design).
  • the photocurable resin composition may be applied to a portion where light does not reach sufficiently, and as a result, the photocurable resin composition applied to a portion where light does not reach is cured. There was a problem that it became insufficient. Therefore, a photothermosetting resin composition is used as a resin composition that can be sufficiently cured even when it is applied to a portion where light does not reach, and both photocuring and thermosetting are used in combination, but at a high temperature. There was a risk that heating would adversely affect the elements and the like.
  • a plurality of thin semiconductor chips may be joined via an adhesive layer to form a laminate of semiconductor chips. It is done.
  • a laminate of semiconductor chips is, for example, a method of applying an adhesive on one semiconductor chip, laminating the other semiconductor chip via the adhesive, and then curing the adhesive. It is manufactured by a method of filling an adhesive between semiconductor chips held at intervals and then curing the adhesive.
  • a method of semi-curing the applied adhesive and then fully curing it is being studied. Therefore, the use of a light-moisture-curable resin composition as an adhesive has been studied for laminating small semiconductor chips and for adhering electronic components such as display elements having a narrow frame design.
  • Patent Document 1 discloses a light-moisture-curable resin composition and an adhesive for electronic components, which are excellent in flexibility of a cured product and reliability in a high-temperature and high-humidity environment.
  • the photo-moisture-curable resin composition disclosed in Patent Document 1 is excellent in stress relaxation property and has adhesive strength durability because a cured product having appropriate flexibility can be obtained.
  • the photo-moisture-curable resin composition disclosed in Patent Document 1 has a problem that the adhesive strength at a high temperature is not sufficient.
  • an object of the present invention is to provide a photo-moisture-curable resin composition and an adhesive for electronic parts, which are excellent in both durability of adhesive strength and sufficient adhesive strength at high temperature.
  • the present inventors have studied a moisture-curable urethane resin in order to improve the high-temperature adhesive strength of the conventional photomoisture-curable resin composition. Then, the present inventors have found that the high temperature adhesive force can be greatly improved by blending the moisture-curable urethane resin having a polyester skeleton as the moisture-curable urethane resin. On the other hand, the present inventors have found that when a moisture-curable urethane resin having a polyester skeleton is used as the moisture-curable urethane resin, it is not possible to obtain sufficient durability of adhesive strength.
  • the present inventors set the rate of change in thickness of the photocured product before and after applying a load to 50% or less, thereby achieving high-temperature adhesive strength and adhesive strength. We have found that it is possible to achieve both the durability of the above and the durability at a high level, and completed the present invention.
  • the present invention provides the following [1] to [30].
  • [1] Contains a radically polymerizable compound, a moisture-curable urethane resin, and a photopolymerization initiator.
  • the moisture-curable urethane resin contains a moisture-curable urethane resin having a polyester skeleton.
  • Sex resin composition [2] The photomoisture-curable resin composition according to the above [1], which has a viscosity of 3000 Pa ⁇ s or less at 25 ° C.
  • R represents any of a hydrogen atom, a methyl group, and an ethyl group
  • l is an integer of 0 to 5
  • m is an integer of 1 to 500
  • n is an integer of 1 to 10.
  • the polyether polyol is at least one selected from the group consisting of polypropylene glycol, a ring-opening polymerization compound of a tetrahydrofuran compound, and a ring-opening polymerization compound of a tetrahydrofuran compound having a methyl group as a substituent.
  • the photomoisture-curable resin composition according to any one of [1] to [11] above, wherein the photocured cured product has a storage elastic modulus of 10 kPa or more at 25 ° C.
  • the storage elastic modulus at 25 ° C. of the cured product obtained by allowing the cured product in the photocured state to stand in an environment of 23 ° C. and 50 RH% for 3 days is 1 MPa or more.
  • the moisture-curable urethane resin having a polyester skeleton reacts a polyester polyol having two or more hydroxyl groups in one molecule with a polyisocyanate compound having two or more isocyanate groups in one molecule.
  • the photo-moisture-curable resin composition according to any one of the above [1] to [13].
  • At least one polyvalent carboxylic acid selected if the polyester polyol is in the group consisting of phthalic acid, terephthalic acid, isophthalic acid, and adipic acid, and 1,6-hexanediol and 1,4-butanediol.
  • the thermosetting resin composition according to the above [17], wherein the (meth) acrylic compound further contains a polyfunctional (meth) acrylic compound.
  • thermosetting resin composition according to the above [18], wherein the content of the polyfunctional (meth) acrylic compound is 1% by mass or more and 50% by mass or less with respect to the total amount of the radically polymerizable compound. .. [20]
  • the photomoisture-curable resin composition according to at least one of the above [17] to [19], wherein the monofunctional (meth) acrylic compound is a (meth) acrylic acid ester compound.
  • the light humidity according to any one of the above [1] to [20], wherein the content of the radically polymerizable compound is 50% by mass or less in 100% by mass of the photomoisture-curable resin composition. Curable resin composition.
  • the content of the photopolymerization initiator in the photo-moisture-curable resin composition is 0.01 parts by mass or more and 10 parts by mass with respect to 100 parts by mass of the total amount of the radical-polymerizable compound and the moisture-curable urethane resin.
  • An adhesive for electronic components comprising the photomoisture-curable resin composition according to any one of the above [1] to [25].
  • FIG. 1A is a plan view
  • FIG. 1B is a side view.
  • the photo-moisture-curable resin composition of the present invention contains a radical-polymerizable compound, a moisture-curable urethane resin, and a photopolymerization initiator, and is a cured product in a state of being photo-cured by irradiating with ultraviolet rays at 1000 mJ / cm 2.
  • a load of 0.04 MPa when a load of 0.04 MPa is applied, the thickness change rate before and after the load is 50% or less.
  • the moisture-curable urethane resin includes a moisture-curable urethane resin having a polyester skeleton.
  • the photomoisture-curable resin composition of the present invention can enhance the adhesive strength in a high temperature environment by containing a urethane prepolymer having a polyester skeleton.
  • the photo-moisture-curable resin composition of the present invention has good stress relaxation property by setting the thickness change rate before and after applying a load to 50% or less with respect to the cured product in the photo-cured state.
  • the durability of the adhesive strength can be enhanced, and a constant adhesive strength can be maintained even if the adhesive strength is repeatedly arranged in a high temperature environment and a low temperature environment, for example.
  • the rate of change in thickness before and after applying the load is preferably 45% or less, more preferably 40% or less.
  • the thickness change rate is preferably 5% or more, more preferably 10% or more.
  • the cured product in a photocured state means a cured product in a state in which the photo-moisture-curable resin composition is photo-cured without being moisture-cured.
  • the thickness change rate before and after applying a load to the cured product in the photocured state may be measured by the following procedure.
  • ⁇ Rate of change in thickness of cured product in photo-cured state> A line width of 1.0 ⁇ 0.1 mm, a length of 25 ⁇ 0.2 mm, and a thickness of a light-moisture-curable resin composition are applied to a polycarbonate substrate (length 50 mm, width 25 mm, thickness 2 mm) using a dispensing device.
  • the photo-moisture-curable resin composition is photocured by irradiating it with ultraviolet rays at 1000 mJ / cm 2 using a UV-LED lamp.
  • the wavelength of the UV-LED lamp can be appropriately selected according to the absorption wavelength of the photopolymerization initiator contained therein, and for example, one having a wavelength of 365 nm can be used.
  • a glass substrate of the same size as the polycarbonate substrate is placed on a cured product that has been photocured in an environment of 25 ° C., and a 100 g weight is allowed to stand on it for 10 seconds to be photocured.
  • Thickness change rate (%) (thickness immediately after light irradiation-thickness after load action) / (thickness immediately after light irradiation) x 100
  • the photomoisture-curable resin composition of the present invention has a storage elastic modulus of a cured product in a photocured state at 25 ° C., for example, 2 kPa or more, preferably 10 kPa or more, more preferably 15 kPa or more, still more preferably. It is 20 kPa or more.
  • the storage elastic modulus of the photocured product at 25 ° C. is preferably 200 kPa or less, more preferably 100 kPa or less, from the viewpoint of increasing the initial adhesive force.
  • the wavelength of the UV-LED lamp can be appropriately selected according to the absorption wavelength of the photopolymerization initiator contained therein, and for example, one having a wavelength of 365 nm can be used.
  • the photo-moisture-curable resin composition of the present invention has a storage elastic modulus at 25 ° C. of the photo-moisture-cured cured product, preferably 1 MPa or more, more preferably 5 MPa or more, and further preferably 10 MPa or more.
  • the storage elastic modulus of the cured product in a light-moisture-cured state at 25 ° C. is, for example, 700 MPa or less, preferably 100 MPa or less, and more preferably 70 MPa or less from the viewpoint of enhancing the durability of the adhesive force.
  • the storage elastic modulus of the cured product in a light-moisture-cured state at 25 ° C. may be measured by the following procedure.
  • the light-moisture-curable resin composition is filled in a Teflon (registered trademark) mold having a width of 3 mm, a length of 30 mm, and a thickness of 1 mm.
  • the curable resin composition is photocured by irradiating with ultraviolet rays at 1000 mJ / cm 2 using a UV-LED lamp.
  • the wavelength of the UV-LED lamp can be appropriately selected according to the absorption wavelength of the photopolymerization initiator contained therein, and for example, one having a wavelength of 365 nm can be used. Then, it is allowed to stand in an environment of 23 ° C. and 50 RH% for 3 days. Take out the cured product in a light-moisture-cured state from the mold, and use a dynamic viscoelasticity measuring device (manufactured by IT Measurement Control Co., Ltd., trade name "DVA-200”) to perform dynamic viscoelasticity in the range of -100 ° C to 150 ° C. Measure and determine the storage elastic modulus at room temperature (25 ° C). The measurement conditions are that the deformation mode is pulled, the set strain is 1%, the measurement frequency is 1 Hz, and the temperature rise rate is 5 ° C./min.
  • the photomoisture-curable resin composition of the present invention has a viscosity measured at 25 ° C. and 1 rpm using a cone plate viscometer, preferably 3000 Pa ⁇ s or less, and more preferably 2500 Pa ⁇ s or less. It is more preferably 2000 Pa ⁇ s or less, further preferably 1500 Pa ⁇ s or less, and even more preferably 800 Pa ⁇ s or less.
  • the viscosity is preferably 50 Pa ⁇ s or more from the viewpoint of suppressing excessive wet spread during coating.
  • the thickness change rate, storage elastic modulus, and viscosity described above are the radical polymerizable compound, the type and amount of each component used in the moisture-curable urethane resin, and the light-moisture-curable resin composition, as described in detail below. It is adjusted by appropriately changing the type and amount of each component added to.
  • the photomoisture curable resin composition of the present invention contains a radically polymerizable compound.
  • the photo-moisture-curable resin composition of the present invention has photocurability by containing a radically polymerizable compound.
  • the photomoisture-curable resin composition of the present invention preferably contains, as a radically polymerizable compound, a compound having a (meth) acryloyl group (hereinafter, referred to as "(meth) acrylic compound").
  • (meth) acrylic compound a compound having a (meth) acryloyl group
  • (meth) acrylic compound means acrylic or methacrylic, and the same applies to other similar terms.
  • Examples of the (meth) acrylic compound include (meth) acrylic acid ester compound, epoxy (meth) acrylate, urethane (meth) acrylate, polyester (meth) acrylate and the like.
  • the (meth) acrylic compound may be monofunctional or polyfunctional.
  • the urethane (meth) acrylate does not have a residual isocyanate group.
  • monofunctional ones include, for example, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, and isobutyl (meth) acrylate.
  • the (meth) acrylic acid ester compound may have an aromatic ring, for example, phenylalkyl (meth) acrylate such as benzyl (meth) acrylate and 2-phenylethyl (meth) acrylate, and phenoxyethyl (meth).
  • phenylalkyl (meth) acrylate such as benzyl (meth) acrylate and 2-phenylethyl (meth) acrylate
  • phenoxyethyl (meth) acrylates such as acrylates.
  • it may be a (meth) acrylate having a plurality of benzene rings such as a fluorene skeleton and a biphenyl skeleton, and specific examples thereof include a fluorene type (meth) acrylate and an ethoxylated o-phenylphenol acrylate.
  • phenoxypolyoxyethylene-based (meth) acrylates such as phenoxydiethylene glycol (meth) acrylate, phenoxypolyethylene glycol (meth) acrylate, nonylphenoxydiethylene glycol (meth) acrylate, and nonylphenoxypolyethylene glycol (meth) acrylate can also be mentioned.
  • the monofunctional (meth) acrylic acid ester compound tetrahydrofurfuryl (meth) acrylate, alkoxylated tetrahydrofurfuryl (meth) acrylate, cyclic trimethylolpropanformal (meth) acrylate, 3-ethyl-3- (Meta) acrylates having a heterocyclic structure such as oxetanylmethyl (meth) acrylates, phthalimide acrylates such as N-acryloyloxyethyl hexahydrophthalimide, various imide (meth) acrylates, 2,2,2-trifluoroethyl ( Meta) acrylate, 2,2,3,3-tetrafluoropropyl (meth) acrylate, 1H, 1H, 5H-octafluoropentyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth)
  • bifunctional (meth) acrylic acid ester compound examples include 1,3-butanediol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, and 1,6-hexanediol di (meth).
  • those having trifunctionality or higher include, for example, trimethylpropantri (meth) acrylate, pentaerythritol tri (meth) acrylate, glycerintri (meth) acrylate, and pentaerythritol tetra (meth).
  • Examples of the epoxy (meth) acrylate include those obtained by reacting an epoxy compound with (meth) acrylic acid.
  • the reaction between the epoxy compound and (meth) acrylic acid may be carried out in the presence of a basic catalyst or the like according to a conventional method.
  • the epoxy (meth) acrylate may be monofunctional or polyfunctional such as bifunctional, but polyfunctional is preferable.
  • Examples of the epoxy compound used as a raw material for synthesizing the epoxy (meth) acrylate include a bisphenol A type epoxy resin, a bisphenol F type epoxy resin, a bisphenol S type epoxy resin, and a 2,2'-diallyl bisphenol A type epoxy resin.
  • Hydrogenated bisphenol type epoxy resin propylene oxide added bisphenol A type epoxy resin, resorcinol type epoxy resin, biphenyl type epoxy resin, sulfide type epoxy resin, diphenyl ether type epoxy resin, dicyclopentadiene type epoxy resin, naphthalene type epoxy resin, phenol Novolac type epoxy resin, orthocresol novolac type epoxy resin, dicyclopentadiene novolac type epoxy resin, biphenyl novolac type epoxy resin, naphthalenephenol novolac type epoxy resin, glycidylamine type epoxy resin, alkyl polyol type epoxy resin, rubber modified epoxy resin , Glysidyl ester compound, bisphenol A type episulfide resin and the like.
  • epoxy (meth) acrylates commercially available ones include, for example, EBECRYL860, EBECRYL3200, EBECRYL3201, EBECRYL3412, EBECRYL3600, EBECRYL3700, EBECRYL3701, EBECRYL3702, EBECRYL3702, EBECRYL3702, EBECRYL370 ), EA-1010, EA-1020, EA-5323, EA-5520, EACHD, EMA-1020 (all manufactured by Shin-Nakamura Chemical Industry Co., Ltd.), epoxy ester M-600A, epoxy ester 40EM, epoxy ester 70PA, epoxy ester.
  • Denacol Acrylate DA-141 examples thereof include Denacol Acrylate DA-314 and Denacol Acrylate DA-911 (both manufactured by Nagase ChemteX Corporation).
  • urethane (meth) acrylate for example, an isocyanate compound reacted with a (meth) acrylic acid derivative having a hydroxyl group can be used.
  • a tin-based compound or the like in the reaction between the isocyanate compound and the (meth) acrylic acid derivative, it is preferable to use a tin-based compound or the like in a catalytic amount as a catalyst.
  • the urethane (meth) acrylate may be monofunctional or polyfunctional such as bifunctional, but bifunctional is preferable.
  • Examples of the isocyanate compound used to obtain urethane (meth) acrylate include isophorone diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, and diphenylmethane-4, 4'-diisocyanate (MDI), hydrogenated MDI, polypeptide MDI, 1,5-naphthalenediocyanate, norbornan diisocyanate, trizine diisocyanate, xylylene diisocyanate (XDI), hydrogenated XDI, lysine diisocyanate, triphenylmethane triisocyanate, tris ( Examples thereof include polyisocyanate compounds such as isocyanatephenyl) thiophosphate, tetramethylxylylene diisocyanate, and 1,6,11-undecantryisocyanate.
  • MDI 4'-di
  • the isocyanate compound a chain-extended polyisocyanate compound obtained by reacting a polyol with an excess isocyanate compound can also be used.
  • the polyol include ethylene glycol, propylene glycol, glycerin, sorbitol, trimethylolpropane, carbonate diol, polyether diol, polyester diol, and polycaprolactone diol.
  • Examples of the (meth) acrylic acid derivative having a hydroxyl group include dihydric alcohols such as ethylene glycol, propylene glycol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, and polyethylene glycol.
  • dihydric alcohols such as ethylene glycol, propylene glycol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, and polyethylene glycol.
  • Mono (meth) acrylate, mono (meth) acrylate or di (meth) acrylate of trihydric alcohols such as trimethylolethane, trimethylolpropane, glycerin, and epoxy (meth) acrylate such as bisphenol A type epoxy (meth) acrylate. ) Acrylate and the like can be mentioned.
  • urethane (meth) acrylates include, for example, M-1100, M-1200, M-1210, M-1600 (all manufactured by Toa Synthetic Co., Ltd.), EBECRYL230, EBECRYL270, EBECRYL8402, EBECRYL8411, EBECRYL8412, EBECRYL8413, EBECRYL8804, EBECRYL8803, EBECRYL8807, EBECRYL9270, EBECRYL210, EBECRYL4827, EBECRYL6700, EBECRYL6700, EBECRYL6700, EBECRYL6700, EBECRYL6700, EBECRYL6700, EBECRYL6700, EBECRYL6700, EBECRYL6700, EBECRYL6700, EBECRYL6700, EBECRYL6700, EBECRYL6700, EBECRYL6700, EBECRYL
  • polyester (meth) acrylate examples include those obtained by reacting a polyester polyol with (meth) acrylic acid.
  • Commercially available polyester (meth) acrylates include, for example, Aronix M-6100, M-6200, M-6250, M-6500, M-7100, M-7300K, M-8030, and M-8060.
  • Doublemer 2015 Doublemer 2231-TF Doubler 2319, Doublemer 257, Doublemer 276, Doublemer 276, Doublemer , Doublemer 236, Doublemer 270, Doublemer 278, Doublemer 285, Doublemer 220, Doublemer 2315-100, Doublemer 245, Doublemer 272, Doublemer 278X25, Doublemer 286, Doublemer 2230-TF, Doublemer 2315HM35, Doublemer 246, Doublemer 275, Doublemer 281, Double bond 287 (both manufactured by Double bond Chemical) and the like can be mentioned.
  • the photo-moisture-curable resin composition may contain (meth) acrylate having a number average molecular weight of 5000 or more (hereinafter, referred to as “polymer (meth) acrylate”) as the (meth) acrylic acid ester compound.
  • polymer (meth) acrylate having a number average molecular weight of 5000 or more
  • the above-mentioned thickness change rate can be easily adjusted within a predetermined range.
  • the polymer (meth) acrylate is, for example, a compound in which the polymer chain portion is a polymer of a (meth) acrylic acid ester compound and has a (meth) acryloyl group at the end.
  • alkyl (meth) acrylate is preferably used.
  • examples of such polymer (meth) acrylate include AA-6 (number average molecular weight 6000, manufactured by Toagosei Co., Ltd.), AB-6 (number average molecular weight 6000, manufactured by Toagosei Co., Ltd.) and the like.
  • the upper limit of the number average molecular weight of the polymer (meth) acrylate is not particularly limited, but is, for example, 100,000 or less.
  • radically polymerizable compounds As the radically polymerizable compound, other radically polymerizable compounds other than those described above can be appropriately used. Examples of other radically polymerizable compounds include N, N-dimethyl (meth) acrylamide, N- (meth) acryloylmorpholine, N-hydroxyethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, and N-.
  • (Meta) acrylamide compounds such as isopropyl (meth) acrylamide, N, N-dimethylaminopropyl (meth) acrylamide, vinyl such as styrene, ⁇ -methylstyrene, N-vinyl-2-pyrrolidone, N-vinyl- ⁇ -caprolactam Examples include compounds.
  • the thickness change rate of the cured product in the photocured state may be within a predetermined range by appropriately combining the types and contents of the radically polymerizable compounds described above.
  • a compound having an acryloyl group as the (meth) acrylic compound
  • the thickness change rate of the cured product in the photocured state is adjusted within a predetermined range. It will be easier.
  • a polyfunctional (meth) acrylic compound as the (meth) acrylic compound, it becomes easy to increase the reactivity at the time of light irradiation, and as a result, the thickness change rate of the cured product in the photocured state can be increased. It becomes easy to adjust within a predetermined range.
  • polyfunctional (meth) acrylic compound examples include a polyfunctional (meth) acrylic acid ester having about 6 to 30 carbon atoms, preferably 8 to 20 carbon atoms.
  • the polyfunctional (meth) acrylic acid ester compound X is preferably 2 to 4 functional, and more preferably 2 to 3 functional.
  • the cohesive force (crosslink density) of the radically polymerizable compound becomes high after photocuring, and the above-mentioned thickness change rate can be further lowered.
  • the viscosity of the light-moisture-curable resin composition before light irradiation is lowered, and the coatability is also improved.
  • polyfunctional (meth) acrylic compound X examples include 1,6-hexanediol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, triethylene glycol di (meth) acrylate, and neopentyl glycol. Examples thereof include di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, dimethyloltricyclodecanedi (meth) acrylate, pentaerythritol tetra (meth) acrylate, and dipentaerythritol hexa (meth) acrylate.
  • the polyfunctional (meth) acrylic compound X may be used alone or in combination of two or more.
  • the polyfunctional (meth) acrylic compound X may be used in combination with a monofunctional radically polymerizable compound.
  • the content of the polyfunctional (meth) acrylic compound X is, for example, 1% by mass or more and 50% by mass or less, preferably 5% by mass or more and 35% by mass or less, more preferably 10% by mass, based on the total amount of the radically polymerizable compound. It is 30% by mass or less.
  • the total content of the polyfunctional (meth) acrylic compound is, for example, 1% by mass or more and 50% by mass or less, preferably 3% by mass or more and 40% by mass or less, based on the total amount of the radically polymerizable compound.
  • the content of the radically polymerizable compound in 100% by mass of the thermosetting resin composition is preferably 3% by mass or more, more preferably 5% by mass or more, and further preferably 10% by mass or more. Further, it is preferably 50% by mass or less, more preferably 40% by mass or less, and further preferably 30% by mass or less.
  • the content of the radically polymerizable compound is at least the above lower limit, it becomes easy to adjust the thickness change rate of the cured product in the photocured state within a predetermined range. Further, when the content of the radically polymerizable compound is not more than the above upper limit, it becomes easy to increase the adhesive force at high temperature.
  • the photomoisture curable resin composition of the present invention contains a photopolymerization initiator.
  • the photopolymerization initiator By including the photopolymerization initiator, the photocurable resin composition of the present invention can be imparted with photocurability.
  • the photopolymerization initiator include benzophenone compounds, acetphenone compounds such as ⁇ -aminoalkylphenone and ⁇ -hydroxyalkylphenone, acylphosphine oxide compounds, titanosen compounds, oxime ester compounds, and benzoin ether compounds. , Thioxanthone and the like.
  • a compound having an acylphosphine oxide-based skeleton or an ⁇ -aminoalkylphenone-based skeleton Compounds having the above are preferred.
  • photopolymerization initiators include, for example, IRGACURE184, IRGACURE369, IRGACURE379, IRGACURE379EG, IRGACURE651, IRGACURE784, IRGACURE819, IRGACURE907, IRGACURE2959, IRGACURE Benzoin Examples thereof include ether, benzoin ethyl ether, and benzoin isopropyl ether (all manufactured by Tokyo Chemical Industry Co., Ltd.).
  • the content of the photopolymerization initiator in the photo-moisture-curable resin composition is preferably 0.01 parts by mass or more, more preferably 0.01 parts by mass or more, based on 100 parts by mass of the total amount of the radical-polymerizable compound and the moisture-curable urethane resin. Is 0.5 parts by mass or more, preferably 10 parts by mass or less, and more preferably 5 parts by mass or less.
  • the content of the photopolymerization initiator is within this range, the obtained photomoisture-curable resin composition has excellent photocurability and storage stability. Further, when the content is within the above range, the radical polymerization compound is appropriately cured, and the thickness change rate of the cured product in the photocured state described above can be easily adjusted within a predetermined range.
  • the photomoisture curable resin composition of the present invention contains a moisture curable urethane resin.
  • the photo-moisture-curable resin composition of the present invention has moisture-curable property.
  • the moisture-curable urethane resin can be obtained by reacting a polyol compound having two or more hydroxyl groups in one molecule with a polyisocyanate compound having two or more isocyanate groups in one molecule.
  • a known polyol compound usually used in the production of polyurethane can be used, and for example, polyester polyol, polyether polyol, polyalkylene polyol, polycarbonate polyol and the like. Can be mentioned. These polyol compounds may be used alone or in combination of two or more.
  • the photo-moisture-curable resin composition of the present invention contains a moisture-curable urethane resin having a polyester skeleton as the moisture-curable urethane resin.
  • a moisture-curable urethane resin having a polyester skeleton as the moisture-curable urethane resin.
  • a moisture-curable urethane resin having a polyester skeleton can be obtained by reacting a polyester polyol having two or more hydroxyl groups in one molecule with a polyisocyanate compound having two or more isocyanate groups in one molecule.
  • the polyester polyol include a polyester polyol obtained by reacting a polyvalent carboxylic acid with a polyol, a poly- ⁇ -caprolactone polyol obtained by ring-opening polymerization of ⁇ -caprolactone, and the like.
  • polyvalent carboxylic acid used as a raw material for the polyester polyol examples include phthalic acid, terephthalic acid, isophthalic acid, 1,5-naphthalic acid, 2,6-naphthalic acid, succinic acid, glutaric acid, adipic acid, and pimelic acid. , Suberic acid, azelaic acid, sebacic acid, decamethylenedicarboxylic acid, dodecamethylenedicarboxylic acid and the like. Among these, phthalic acid, terephthalic acid, isophthalic acid, or adipic acid is preferable from the viewpoint of easily increasing the adhesive force at high temperature. These polyvalent carboxylic acids may be used alone or in combination of two or more.
  • polyol used as a raw material for the polyester polyol examples include ethylene glycol, propylene glycol, 1,3-propanediol, 1,4-butanediol, neopentyl glycol, 1,5-pentanediol, and 1,6-hexanediol. , Diethylene glycol, cyclohexanediol and the like. Among these, 1,6-hexanediol or 1,4-butanediol is preferable from the viewpoint of easily increasing the adhesive force at high temperature. These polyols may be used alone or in combination of two or more.
  • an aromatic polyisocyanate compound and an aliphatic polyisocyanate compound are preferably used.
  • the aromatic polyisocyanate compound include diphenylmethane diisocyanate, liquid modified products of diphenylmethane diisocyanate, polypeptide MDI, tolylene diisocyanate, naphthalene-1,5-diisocyanate and the like.
  • Examples of the aliphatic polyisocyanate compound include hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, lysine diisocyanate, norbornane diisocyanate, transcyclohexane-1,4-diisocyanate, isophorone diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated diphenylmethane diisocyanate, and cyclohexane diisocyanate. , Bis (isocyanate methyl) cyclohexane, dicyclohexylmethane diisocyanate and the like.
  • polyisocyanate compound diphenylmethane diisocyanate and its modified product are particularly preferable from the viewpoint of being able to increase the adhesive force after total curing.
  • the polyisocyanate compound may be used alone or in combination of two or more.
  • the moisture-curable urethane resin having the polyester skeleton may have a polyether skeleton in the molecule.
  • the moisture-curable urethane resin having a polyester skeleton having a polyether skeleton in the molecule is, for example, a polyester polyol having two or more hydroxyl groups in one molecule and a polyether having two or more hydroxyl groups in one molecule. It can be obtained by reacting a polyol with a polyisocyanate compound having two or more isocyanate groups in one molecule.
  • the polyester polyol the polyester polyol described above can be used.
  • a polyether polyol described later can be used.
  • the photo-moisture-curable resin composition preferably further contains, as the moisture-curable urethane resin, a moisture-curable urethane resin having a polyether skeleton in addition to the moisture-curable urethane resin having a polyester skeleton.
  • a moisture-curable urethane resin having a polyether skeleton By further containing a moisture-curable urethane resin having a polyether skeleton, it becomes easy to improve the coatability of the photomoisture-curable resin composition.
  • the moisture-curable urethane resin having a polyether skeleton referred to here is a moisture-curable urethane resin that does not contain a polyester skeleton.
  • a urethane resin having a polyether skeleton can be obtained by reacting a polyether polyol having two or more hydroxyl groups in one molecule with a polyisocyanate compound having two or more isocyanate groups in one molecule.
  • the polyether polyol include a ring-opening polymer of ethylene glycol, propylene glycol and tetrahydrofuran, a ring-opening polymer of 3-methyl tetrahydrofuran, and a random copolymer or block copolymer of these or derivatives thereof, or a bisphenol type.
  • the bisphenol-type polyoxyalkylene modified product is a polyether polyol obtained by adding an alkylene oxide (for example, ethylene oxide, propylene oxide, butylene oxide, isobutylene oxide, etc.) to the active hydrogen portion of the bisphenol-type molecular skeleton.
  • the polyether polyol may be a random copolymer or a block copolymer.
  • the bisphenol-type polyoxyalkylene modified product preferably has one or more alkylene oxides added to both ends of the bisphenol-type molecular skeleton.
  • the bisphenol type is not particularly limited, and examples thereof include A type, F type, and S type, and bisphenol A type is preferable.
  • the polyisocyanate compound the above-mentioned polyisocyanate compound can be used.
  • the moisture-curable urethane resin having a polyether skeleton preferably further contains one obtained by using a polyol compound having a structure represented by the following formula (1).
  • a polyol compound having a structure represented by the following formula (1) By using a polyol compound having a structure represented by the following formula (1), a photomoisture-curable resin composition having excellent adhesiveness and a cured product having flexibility and good elongation can be obtained, and a radically polymerizable compound can be obtained. It has excellent compatibility with.
  • the storage elastic modulus can be easily adjusted within the above-mentioned desired range.
  • a polyether polyol composed of a ring-opening polymerization compound of propylene glycol or a tetrahydrofuran (THF) compound or a ring-opening polymerization compound of a tetrahydrofuran compound having a substituent such as a methyl group are preferable, and propylene glycol is more preferable. preferable.
  • R represents a hydrogen atom, a methyl group, or an ethyl group
  • l is an integer of 0 to 5
  • m is an integer of 1 to 500
  • n is an integer of 1 to 10.
  • .. l is preferably 0 to 4
  • m is preferably 50 to 200
  • n is preferably 1 to 5.
  • the case where l is 0 means the case where the carbon bonded to R is directly bonded to oxygen.
  • the total of n and l is more preferably 1 or more, and further preferably 1 to 3.
  • R is more preferably a hydrogen atom or a methyl group, and particularly preferably a methyl group.
  • the photo-moisture-curable resin composition of the present invention may contain a moisture-curable urethane resin having the polyester skeleton or a moisture-curable urethane resin other than the moisture-curable urethane resin having the polyether skeleton.
  • a moisture-curable urethane resin having the polyester skeleton or a moisture-curable urethane resin other than the moisture-curable urethane resin having the polyether skeleton.
  • other moisture-curable urethane resins include urethane resins having a polyalkylene skeleton and urethane resins having a polycarbonate skeleton.
  • a urethane resin having a polyalkylene skeleton can be obtained by reacting a polyalkylene polyol having two or more hydroxyl groups in one molecule with a polyisocyanate compound having two or more isocyanate groups in one molecule.
  • a polyalkylene polyol examples include a polybutadiene polyol, a hydrogenated polybutadiene polyol, and a hydrogenated polyisoprene polyol.
  • the polyisocyanate compound the above-mentioned polyisocyanate compound can be used.
  • a urethane resin having a polycarbonate skeleton can be obtained by reacting a polycarbonate polyol having two or more hydroxyl groups in one molecule with a polyisocyanate compound having two or more isocyanate groups in one molecule.
  • the polycarbonate polyol include polyhexamethylene carbonate polyol and polycyclohexanedimethylene carbonate polyol.
  • the polyisocyanate compound the above-mentioned polyisocyanate compound can be used as the polyisocyanate compound.
  • the moisture-curable urethane resin may have a radically polymerizable functional group.
  • a group having an unsaturated double bond is preferable, and a (meth) acryloyl group is more preferable from the viewpoint of reactivity.
  • the moisture-curable resin having a radical-polymerizable functional group is not included in the above-mentioned radical-polymerizable compound and is treated as a moisture-curable resin.
  • the weight average molecular weight of the moisture-curable urethane resin is not particularly limited, but is preferably 500 or more, more preferably 1000 or more, and preferably 10000 or less, more preferably 8000 or less.
  • the weight average molecular weight is at least the above lower limit, it becomes easy to increase the adhesive force at high temperature. Further, when the weight average molecular weight is not more than the above upper limit, the coatability is easily improved.
  • the weight average molecular weight and the number average molecular weight are values obtained by measuring by gel permeation chromatography (GPC) and converting into polystyrene.
  • GPC gel permeation chromatography
  • Examples of the column for measuring the weight average molecular weight in terms of polystyrene by GPC include Shodex LF-804 (manufactured by Showa Denko KK). Further, as a solvent used in GPC, tetrahydrofuran can be mentioned.
  • the content of the moisture-curable urethane resin in 100% by mass of the light-moisture-curable resin composition is preferably 45% by mass or more, more preferably 50% by mass or more, and further preferably 60% by mass or more. Further, it is preferably 95% by mass or less, and more preferably 90% by mass or less.
  • the content of the moisture-curable urethane resin is at least the above lower limit, it becomes easy to increase the adhesive force at high temperature.
  • the content of the moisture-curable urethane resin is not more than the above upper limit, it becomes easy to increase the durability of the adhesive force.
  • the content of the moisture-curable urethane resin having a polyester skeleton in 100% by mass of the photo-moisture-curable resin composition is, for example, 25% by mass or more, preferably 30% by mass or more, and more preferably 40% by mass. % Or more, more preferably 50% by mass or more, preferably 95% by mass or less, and more preferably 90% by mass or less.
  • the content of the moisture-curable urethane resin having a polyester skeleton is at least the above lower limit, it becomes easy to increase the adhesive force at high temperature.
  • the content of the moisture-curable urethane resin having a polyester skeleton is not more than the above upper limit, it becomes easy to increase the durability of the adhesive force.
  • the photo-moisture-curable resin composition contains a moisture-curable urethane resin having a polyester skeleton and another moisture-curable urethane resin, another moisture-curable urethane resin with respect to the moisture-curable urethane resin having a polyester skeleton.
  • the mass ratio of the content of (other moisture-curable urethane resin / moisture-curable urethane resin having a polyester skeleton) is preferably 5 or less, more preferably 3 or less, and preferably 0.001 or more. It is more preferably 0.01 or more.
  • the other moisture-curable urethane resin referred to here is a moisture-curable urethane resin other than the moisture-curable urethane resin having a polyester skeleton, such as a moisture-curable urethane resin having a polyether skeleton.
  • the photo-moisture-curable resin composition preferably has a mass ratio of the content of the radical-polymerizable compound to the moisture-curable urethane resin (radical-polymerizable compound / moisture-curable urethane resin) of, for example, 0.04 or more. Is 0.1 or more, more preferably 0.2 or more, preferably 1 or less, more preferably 0.8 or less, still more preferably 0.6 or less.
  • the photomoisture curable resin composition of the present invention may further contain a non-reactive polymer.
  • the non-reactive polymer include acrylic resin and polyolefin resin.
  • the acrylic resin is a polymer of a polymerizable monomer such as (meth) acrylate.
  • the method for producing the acrylic resin is not particularly limited, and can be produced, for example, by solution polymerization, suspension polymerization, bulk polymerization, or the like of a polymerizable monomer such as the radically polymerizable compound described above.
  • the weight average molecular weight of the acrylic resin is not particularly limited, but is preferably 10,000 or more, and preferably 50,000 or less.
  • the weight average molecular weight is at least the above lower limit, it becomes easy to increase the adhesive force at high temperature. Further, when the weight average molecular weight is not more than the above upper limit, the coatability is easily improved.
  • the polyolefin resin is not particularly limited, and examples thereof include polyethylene and polypropylene.
  • the weight average molecular weight of the polyolefin resin is not particularly limited, but is preferably 10,000 or more, and preferably 50,000 or less. When the weight average molecular weight is at least the above lower limit, it becomes easy to increase the adhesive force at high temperature. Further, when the weight average molecular weight is not more than the above upper limit, the coatability is easily improved.
  • the content of the non-reactive polymer in 100% by mass of the thermosetting resin composition is preferably 5% by mass or more, more preferably 10% by mass or more, and preferably 45% by mass or less. It is more preferably 40% by mass or less.
  • the content of the non-reactive polymer is at least the above lower limit, it becomes easy to increase the adhesive force at high temperature.
  • the content of the non-reactive polymer is not more than the above upper limit, it becomes easy to increase the durability of the adhesive force.
  • the photomoisture curable resin composition of the present invention may contain spacer particles.
  • spacer particles When the photo-moisture-curable resin composition of the present invention contains spacer particles, it becomes easy to adjust the thickness change rate of the cured product in the photo-cured state within the above-mentioned range.
  • the spacer particles include resin particles formed of resin, inorganic particles excluding metal particles, organic-inorganic hybrid particles, and metal particles.
  • the spacer particles are preferably resin particles or organic-inorganic hybrid particles.
  • the spacer particles may be core-shell particles having a core and a shell arranged on the surface of the core.
  • the core may be an organic core.
  • the shell may be an inorganic shell.
  • Spacer particles excluding metal particles are preferable, and resin particles, inorganic particles excluding metal particles, or organic-inorganic hybrid particles are preferable from the viewpoint of being able to relieve stress at the adhesive portion with the adherend and maintaining high adhesive strength durability. Is more preferable, and resin particles are further preferable.
  • the spacer particles are resin particles, when stress is applied to the adhesive portion, the stress can be relaxed and the adhesiveness can be maintained high.
  • the average particle size of the spacer particles is preferably 50 ⁇ m or more, more preferably 80 ⁇ m or more, from the viewpoint of being able to relieve stress at the adhesive portion with the adherend and maintaining high adhesive strength durability. Further, it is preferably 500 ⁇ m or less, and more preferably 400 ⁇ m or less.
  • the above average particle size indicates a number average particle size.
  • the average particle size of the spacer particles can be obtained, for example, by observing 50 arbitrary spacer particles with an electron microscope or an optical microscope and calculating an average value. Twice
  • the CV value of the particle size of the spacer particles is preferably 10% or less, preferably 5% or less, from the viewpoint of further enhancing the adhesiveness.
  • the lower limit of the CV value of the particle size of the spacer particles is not particularly limited, but is preferably 1% or more.
  • the content of the spacer particles in 100% by mass of the photomoisture-curable resin composition is preferably from the viewpoint of further enhancing the stress relaxation property. It is 1% by mass or more, more preferably 5% by mass or more. Further, from the viewpoint of improving the coatability, the content of the spacer particles is preferably 20% by mass or less, and more preferably 15% by mass or less.
  • the thickness change rate can be reduced even if the content of the radically polymerizable compound is reduced.
  • the content of the radically polymerizable compound in 100% by mass of the photomoisture-curable resin composition may be, for example, 20% by mass or less, or 3% by mass or more and 10% by mass or less.
  • the mass ratio (radical polymerizable compound / moisture-curable urethane resin) may be 0.2 or less, or 0.04 or more and 0.1 or less.
  • the curable resin composition of the present invention may contain a filler.
  • the filler By containing the filler, the curable resin composition of the present invention tends to have thixotropy property, and it becomes easy to improve the fine line coating property.
  • a particulate material may be used.
  • the filler means that the average particle size of the primary particles is less than 1 ⁇ m.
  • the filler is preferably an inorganic filler, and examples thereof include silica, talc, titanium oxide, zinc oxide, and calcium carbonate. Of these, silica is preferable because the obtained curable resin composition has excellent ultraviolet transmittance.
  • the filler may be subjected to a hydrophobic surface treatment such as a silylation treatment, an alkylation treatment and an epoxidation treatment.
  • silica, talc, titanium oxide and the like have a function of coloring a light-moisture-curable resin composition in the same manner as a colorant described later.
  • the filler may be used alone or in combination of two or more.
  • the total amount of the filler is, for example, 0.1 part by mass or more, preferably 1 part by mass or more, and more preferably 3 parts by mass with respect to 100 parts by mass of the thermosetting resin composition. It is more than parts, preferably 30 parts by mass or less, and more preferably 20 parts by mass or less.
  • the photomoisture curable resin composition of the present invention may contain a colorant.
  • the colorant include iron oxide, titanium black, aniline black, cyanine black, fullerene, carbon black and the like. Of these, titanium black is preferred.
  • the colorant is preferably black, but may have other colors.
  • the colorant is preferably a material having an ability (light-shielding property) that makes it difficult for light in the visible light region to pass through. Titanium black is a substance having a higher transmittance in the vicinity of the ultraviolet region, particularly for light having a wavelength of 360 to 450 nm, as compared with the average transmittance for light having a wavelength of 300 to 800 nm.
  • the titanium black has a property of imparting light-shielding property to the photomoisture-curable resin composition by sufficiently blocking light having a wavelength in the visible light region, while transmitting light having a wavelength near the ultraviolet region. .. Therefore, it becomes easy to maintain good photocurability of the photo-moisture-curable resin composition while imparting light-shielding property, and to maintain the storage elastic modulus after photo-curing to a high value.
  • the total amount of the colorant is, for example, 0.01 part by mass or more, preferably 0.05 part by mass or more, more preferably 0.05 part by mass or more, based on 100 parts by mass of the photomoisture-curable resin composition. It is 0.1 part by mass or more, preferably 5 parts by mass or less, and more preferably 3 parts by mass or less.
  • the photomoisture-curable resin composition of the present invention may contain a moisture-curing accelerating catalyst that accelerates the moisture-curing reaction of the moisture-curable urethane resin.
  • a moisture-curing accelerating catalyst that accelerates the moisture-curing reaction of the moisture-curable urethane resin.
  • the moisture curing accelerating catalyst include tin compounds such as din-butyltin dilaurate, din-butyltin diacetate, and tin octylate, triethylamine, and 1,4-diazabicyclo [2.2.2] octane.
  • the content of the moisture-curing accelerating catalyst is preferably 0.01 parts by mass or more, more preferably 0.1 parts by mass or more, and preferably 0.1 parts by mass or more, based on 100 parts by mass of the photomoisture-curable resin composition. It is 5 parts by mass or less, more preferably 3 parts by mass or less. When the content of the moisture-curing accelerating catalyst is within this range, the effect of accelerating the moisture-curing reaction is excellent without deteriorating the storage stability of the photo-moisture-curable resin composition.
  • the photomoisture curable resin composition of the present invention may contain a coupling agent.
  • a coupling agent By containing a coupling agent, it becomes easy to improve the adhesive strength.
  • the coupling agent include a silane coupling agent, a titanate-based coupling agent, a zirconate-based coupling agent, and the like. Of these, a silane coupling agent is preferable because it has an excellent effect of improving adhesiveness.
  • the coupling agent may be used alone or in combination of two or more.
  • the content of the coupling agent is preferably 0.05 parts by mass or more, more preferably 0.2 parts by mass or more, and preferably 5 parts by mass with respect to 100 parts by mass of the photomoisture-curable resin composition. It is not less than parts by mass, and more preferably 3 parts by mass or less. By setting the content of the coupling agent within these ranges, the adhesive strength can be improved without affecting the storage elastic modulus and the like.
  • the photomoisture curable resin composition of the present invention may be diluted with a solvent, if necessary.
  • the mass parts and mass% of the photomoisture curable resin composition are based on the solid content, that is, the mass parts and mass% excluding the solvent. ..
  • the light-moisture-curable resin composition may contain additives such as wax particles and metal-containing particles in addition to the components described above.
  • a radical-polymerizable compound, a moisture-curable urethane resin, a photopolymerization initiator, and, if necessary, a filling material are blended using a mixer.
  • a method of mixing with other additives such as an agent and a colorant.
  • the mixer include a homodisper, a homomixer, a universal mixer, a planetary mixer (planetary stirrer), a kneader, and three rolls.
  • the photomoisture curable resin composition of the present invention is cured and used as a cured product. Specifically, the photo-moisture-curable resin composition of the present invention is first photo-cured by light irradiation to, for example, a B-stage state (semi-cured state), and then cured by moisture to be fully cured. good.
  • the photo-moisture-curable resin composition is arranged between the adherends, and when the adherends are bonded to each other, the photo-moisture-curable resin composition is applied to one of the adherends, and then photo-cured by light irradiation.
  • the other adherend is superposed on the photo-curable resin composition in the photocured state, and the adherends are temporarily bonded with an appropriate adhesive force (initial adhesive force). good.
  • an appropriate adhesive force initial adhesive force.
  • the light irradiated during photocuring is not particularly limited as long as it is light that cures the radically polymerizable compound, but ultraviolet rays are preferable. Further, when the photo-moisture-curable resin composition is completely cured by moisture after photo-curing, it may be left in the air for a predetermined time.
  • the photomoisture curable resin composition of the present invention is preferably used as an adhesive for electronic parts. Therefore, the adherend is not particularly limited, but is preferably various electronic components constituting the electronic device. Examples of various electronic components constituting the electronic device include various electronic components provided on the display element, a substrate on which the electronic components are mounted, and a semiconductor chip.
  • the material of the adherend may be any of metal, glass, plastic and the like.
  • the shape of the adherend is not particularly limited, and examples thereof include a film shape, a sheet shape, a plate shape, a panel shape, a tray shape, a rod (rod shape) shape, a box shape, and a housing shape. ..
  • an example of a method for manufacturing an electronic device using the adhesive for electronic parts includes a step of heating the adhesive for electronic parts and a step of applying the heated adhesive for electronic parts to electronic parts. It is a manufacturing method of an electronic device including.
  • the temperature in the heating step is, for example, 130 ° C. or lower, preferably 100 ° C. or lower, more preferably 80 ° C. or lower, and preferably 30 ° C. or higher.
  • the photomoisture curable resin composition of the present invention is preferably used for joining electronic components constituting electronic devices.
  • the photomoisture curable resin composition of the present invention is also preferably used for joining an electronic component to another component. With these configurations, the electronic component will have the cured product of the present invention.
  • the photo-moisture-curable resin composition of the present invention is used inside an electronic device or the like to obtain, for example, a substrate and a substrate by adhering them to each other to obtain an assembled part.
  • the assembly component thus obtained has a first substrate, a second substrate, and a cured product of the present invention, and at least a part of the first substrate is at least a part of the second substrate. Is joined via a cured product. It should be noted that preferably, at least one electronic component is attached to each of the first substrate and the second substrate.
  • each thermosetting resin composition obtained in Examples and Comparative Examples was applied to a polycarbonate substrate (length 50 mm, width 25 mm, thickness 2 mm) using a dispensing device.
  • the coating was applied so as to have a length of 1.0 ⁇ 0.1 mm, a length of 25 ⁇ 0.2 mm, and a thickness of 0.4 ⁇ 0.1 mm.
  • the photo-moisture-curable resin compositions obtained in Examples 1, 2, 5 to 8 and Comparative Example 1 were applied after heating at 50 ° C. for 1 hour, and the photo-moisture-curable resin compositions obtained in Example 3 were applied.
  • the sex resin composition was applied after heating at 120 ° C.
  • the photo-moisture-curable resin compositions obtained in Example 4 and Comparative Example 2 were applied at room temperature.
  • the photo-moisture-curable resin composition was photocured by irradiating with UV-LED (wavelength 365 nm) at 1000 mJ / cm 2 of ultraviolet rays. The thickness immediately after irradiation with ultraviolet rays was measured and used as the thickness before the load was applied.
  • UV-LED wavelength 365 nm
  • 0.04 MPa is applied to the cured product in the photocured state. The load of was applied for 10 seconds.
  • Thickness change rate (%) (thickness immediately after light irradiation-thickness after load action) / (thickness immediately after light irradiation) x 100
  • the thickness of the cured product in the photocured state was measured by observing with a digital microscope (trade name "KH-7800", manufactured by Hirox Corporation).
  • ⁇ Storage elastic modulus of the cured product in the photo-cured state> 3 g of the light-moisture-curable resin composition was set in a UV irradiation rheometer (trade name: HAAKE MARS 40/60, manufactured by Thermo Fisher Scientific). Thirty seconds after the setting was completed, the film was photocured by irradiating with an ultraviolet ray of 1000 mJ / cm 2 using a UV-LED lamp. Sixty seconds after the irradiation with ultraviolet rays, the shear storage elastic modulus was measured under the condition of frequency F 1.6 Hz under the condition of 25 ° C. and 50 RH% environment. The UV-LED lamp used had a wavelength of 365 nm.
  • the dynamic viscoelasticity was measured in the range of -100 ° C to 150 ° C by a dynamic viscoelasticity measuring device (manufactured by IT Measurement Control Co., Ltd., trade name "DVA-200"), and the room temperature ( The storage elastic modulus at 25 ° C.) was determined.
  • the measurement conditions were that the deformation mode was pulled, the set strain was 1%, the measurement frequency was 1 Hz, and the temperature rising rate was 5 ° C./min.
  • Viscosity> The viscosities of the light-moisture-curable resin compositions obtained in Examples and Comparative Examples were measured using a coplate type viscometer (“VISCOMETER TV-22” manufactured by Toki Sangyo Co., Ltd.) at a rotation speed of 1 rpm at 25 ° C. Measured under conditions.
  • each of the photomoisture-curable resin compositions 10 obtained in Examples and Comparative Examples had a width of 0.4 ⁇ 0.05 mm, a length of 25 ⁇ 2 mm, and a length of 25 ⁇ 2 mm. It was applied to the glass plate 11 so as to have a thickness of 0.2 ⁇ 0.05 mm.
  • the curable resin composition 10 was photocured by irradiating with UV-LED (wavelength 365 nm) at 1000 mJ / cm 2 of ultraviolet rays.
  • the glass plates 12 were overlapped and a weight of 100 g was allowed to stand on the glass plates 12 for 10 seconds, so that a load of 0.04 MPa was applied to the cured product in the photocured state for 10 seconds. Then, 100 g of the weight was removed, and the mixture was left to stand in an environment of 23 ° C. and 50 RH% for 3 days to be moisture-cured (mainly cured) to prepare an evaluation sample 13.
  • the prepared evaluation sample 13 is pulled at a speed of 12 mm / sec in the shearing direction S using a tensile tester at 100 ° C. in a 50% RH atmosphere to determine the strength at which the glass plate 11 and the glass plate 12 are peeled off.
  • the adhesive strength at 100 ° C. was measured. The measured adhesive strength was evaluated according to the following evaluation criteria.
  • An evaluation sample 13 was prepared in the same manner as in the above-mentioned evaluation of high-temperature adhesiveness, except that the glass plate 11 was changed to a polycarbonate plate. The evaluation sample was subjected to 1000 cycles of a thermal cycle test in which 40 ° C. for 30 minutes and 80 ° C. for 30 minutes were repeated. For each evaluation sample before and after the cold test, the polycarbonate plate and the glass plate 12 were pulled together in the shearing direction S at a speed of 12 mm / sec using a tensile tester under a 25 ° C. and 50% RH atmosphere. The strength at the time of peeling was measured, and the adhesive strength at 25 ° C. was measured.
  • each photomoisture-curable resin composition obtained in Examples and Comparative Examples the coatability at room temperature, 50 ° C., and 120 ° C. was evaluated using an air dispenser (ML-5000XII, manufactured by Musashi Engineering Co., Ltd.). did.
  • ML-5000XII manufactured by Musashi Engineering Co., Ltd.
  • each light-moisture-curable resin composition is filled in a 10 mL syringe (manufactured by Musashi Engineering Co., Ltd.), left in an oven set at each temperature for 1 hour, and then standard discharge conditions as follows. It was evaluated whether or not fine wire application was possible.
  • the moisture-curable urethane resin used in each Example and Comparative Example was prepared according to the following Synthesis Examples 1 to 4.
  • the moisture-curable urethane resin 1 having a polyester skeleton was produced according to the following Synthesis Example 1.
  • Synthesis Example 1 As a polyol compound, a separable volume of 100 parts by mass of a polyester polyol (polycondensate of adipic acid and 1,6 hexanediol and an alcohol at the end) and 0.01 parts by mass of dibutyltin dilaurate in a volume of 500 mL. It was placed in a flask, stirred under vacuum (20 mmHg or less) at 100 ° C. for 30 minutes, and mixed.
  • the moisture-curable urethane resin 2 having a polyester skeleton was produced according to the following Synthesis Example 2.
  • Synthesis Example 2 As a polyol compound, 100 parts by mass of a polyester polyol (a polyester polyol obtained mainly containing adipic acid, 1,6-hexanediol and isophthalic acid, an aromatic ring concentration of 15% by mass, a weight average molecular weight of 1000) and 0.01 mass by mass. A portion of dibutyltin dilaurate was placed in a 500 mL separable flask. The mixture was stirred and mixed at 100 ° C. for 30 minutes under vacuum (20 mmHg or less).
  • the moisture-curable urethane resin 1 having a polyether skeleton was produced according to the following Synthesis Example 3.
  • Synthesis Example 3 As a polyol compound, 100 parts by mass of polypropylene glycol (manufactured by Asahi Glass Co., Ltd., trade name "EXCENOL 2020") and 0.01 parts by mass of dibutyltin dilaurate are placed in a 500 mL separable flask and placed under vacuum (20 mmHg or less). The mixture was stirred at 100 ° C. for 30 minutes and mixed.
  • the moisture-curable urethane resin 2 having a polyether skeleton was prepared according to the following Synthesis Example 4.
  • Synthesis Example 4 100 parts by mass of polytetramethylene ether glycol (manufactured by Mitsubishi Chemical Corporation, trade name "PTMG-2000”) and 0.01 parts by mass of dibutyltin dilaurate as a polyol compound are placed in a 500 mL separable flask and placed under vacuum. (20 mmHg or less), stirred at 100 ° C. for 30 minutes and mixed.
  • Examples 1 to 8, Comparative Examples 1 and 2 According to the compounding ratios shown in Table 1, each material is stirred at a temperature of 50 ° C. with a planetary stirrer (Sinky Co., Ltd., “Awatori Rentaro”), and then at a temperature of 50 ° C. with three ceramic rolls. The mixture was uniformly mixed to obtain a photomoisture-curable resin composition of Examples 1 to 3 and Comparative Examples 1 and 2.
  • the light-moisture-curable resin composition has good high-temperature adhesiveness by containing a moisture-curable urethane resin having a polyester skeleton. Further, it can be seen that when the thickness change rate is 50% or less, the stress relaxation property becomes good and the durability of the adhesive force becomes good.

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PCT/JP2021/003989 2020-02-05 2021-02-03 光湿気硬化性樹脂組成物、電子部品用接着剤、電子部品の製造方法及び硬化体 WO2021157624A1 (ja)

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JP7649113B2 (ja) 2020-06-09 2025-03-19 積水化学工業株式会社 接着剤組成物、光学部品、電子部品、及び、電子モジュール

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JP2016074826A (ja) * 2014-10-07 2016-05-12 Dic株式会社 積層体の製造方法及び化粧造作部材
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JP5999828B1 (ja) * 2013-09-26 2016-09-28 昆山天洋熱熔膠有限公司 織物貼り合わせ用湿気硬化型反応性ポリウレタンホットメルト接着剤の製造方法
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