WO2012096330A1 - 多官能アクリレート化合物を含む活性エネルギー線硬化性樹脂組成物 - Google Patents

多官能アクリレート化合物を含む活性エネルギー線硬化性樹脂組成物 Download PDF

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WO2012096330A1
WO2012096330A1 PCT/JP2012/050435 JP2012050435W WO2012096330A1 WO 2012096330 A1 WO2012096330 A1 WO 2012096330A1 JP 2012050435 W JP2012050435 W JP 2012050435W WO 2012096330 A1 WO2012096330 A1 WO 2012096330A1
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resin composition
meth
curable resin
active energy
energy ray
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PCT/JP2012/050435
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English (en)
French (fr)
Japanese (ja)
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茂樹 遠山
尾上　慎弥
智史 青野
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協立化学産業株式会社
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Priority to CN201280005289.5A priority Critical patent/CN103314023B/zh
Priority to KR1020137021130A priority patent/KR101686700B1/ko
Publication of WO2012096330A1 publication Critical patent/WO2012096330A1/ja

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    • 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
    • C08F290/061—Polyesters; Polycarbonates
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
    • C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
    • C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • 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
    • C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
    • 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
    • C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
    • C09J171/02—Polyalkylene oxides
    • 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

Definitions

  • the present invention is an active energy ray-curable resin composition containing a polyfunctional acrylate compound, and particularly has high holding power in durability tests including heat resistance tests while having adhesiveness to metal or plastic members.
  • the present invention relates to an active energy ray-curable resin composition that exhibits dimensional stability during heating and is cured by irradiation with active energy rays such as UV and visible light.
  • each member In the field of equipment used for recording and reproduction of recording materials such as CD or DVD, or in recent years, such as Blue-Ray, each member is required to have high heat resistance and impact resistance as the equipment becomes smaller.
  • LCP Liquid crystal polymer
  • COP cycloolefin polymer
  • COC cycloolefin copolymer
  • PPS polyphenylene sulfide
  • PPO polyphenylene oxide
  • Many refined composite plastic materials have come to be used.
  • an adhesive with high fixing accuracy has high adhesion and durability to these materials, and there is little deformation of the cured resin part when heated. It has been demanded.
  • the adhesive is required to be cured more rapidly
  • the fixing accuracy is an accuracy indicating that the light detector does not move from a predetermined position when the light emitting element or the light detector is fixed to the housing which is the base member made of the above-described members. If the fixing accuracy is low, the light emitting element or the photodetector moves from a predetermined position at the time of manufacturing the optical pickup device or after the durability test, and light detection cannot be performed. Therefore, high fixing accuracy is required.
  • a cationic curable epoxy resin is superior to a photocurable acrylic resin adhesive as a photocurable adhesive, and the cationic curable epoxy resin composition is an acrylic resin adhesive.
  • the cationic curable epoxy resin has a problem that it is inferior in rapid curability to the acrylic resin system.
  • Patent Document 1 discloses a curable composition that can be used as an adhesive for adherends such as liquid crystal polymers, cycloolefin polymers, polyarylate, and polycarbonate.
  • adherends such as liquid crystal polymers, cycloolefin polymers, polyarylate, and polycarbonate.
  • Acrylic adhesives have the advantage of better curability than epoxy resins, but have a large change in elastic modulus when heat is applied, so that the adhesive deforms and allows movement of the members. .
  • Patent Document 2 describes a polarizing plate including a polarizer, an adhesive layer, and a cured resin layer.
  • a cured resin layer formed from a solventless photocurable composition containing at least one of a polyfunctional acrylic monomer and a polyfunctional methacryl monomer and a photocurable prepolymer is a hard coat (high hardness) layer. It is described that it is used as.
  • the solventless photocurable composition described in Patent Document 2 is used as an adhesive, there is a problem that the curing shrinkage is large and curling (warping) or peeling is likely to occur.
  • the problem of the present invention is that it has a high initial adhesiveness to a plastic material such as polyphenylene sulfide (PPS) or a metal member, and exhibits a high holding force in a durability test including a high temperature and high humidity test, It is an object of the present invention to provide a resin composition in which deformation during heat, and deformability with respect to heat and load are suppressed to a very low level, thereby suppressing the movement of components.
  • PPS polyphenylene sulfide
  • an active energy ray-curable composition comprising the following components (A) to (D): It has been found that this is possible, and the present invention has been achieved.
  • the present invention is an active energy ray-curable resin composition, comprising the following components (A) to (D): (A) (a1) a linear or branched multimer having a glycerol derivative and an ether skeleton as a linking functional group, (A2) a trimethylolpropane derivative and a linear or branched multimer having an ether skeleton as a linking functional group, (A3) a monomer of pentaerythritol derivative and a linear or branched multimer having an ether skeleton as a linking functional group, and (a4) an ether bond or an ester bond, and at least 4 terminals (meth) A polyfunctional acrylate compound containing four or more (meth) acryloyl groups in the molecule, selected from the group consisting of dendritic molecular compounds in which acryloyl groups are arranged; (B) a photocurable prepolymer,
  • the present invention relates to an active energy ray-curable resin composition
  • the present invention relates to the active energy ray-curable resin composition as described above, wherein the component (A) is 0.01 to 25% by weight based on the weight of the components (A) to (D).
  • the present invention relates to the active energy ray-curable resin composition described above, which is an adhesive for laminating optical components.
  • the present invention relates to the active energy ray-curable resin composition described above, which is an adhesive for assembling an optical pickup device.
  • the present invention relates to an adhesive structure bonded with the active energy ray-curable resin composition described above.
  • the present invention relates to an optical component bonded using the active energy ray-curable resin composition described above.
  • the present invention relates to an optical pickup device assembled using the active energy ray-curable resin composition described above.
  • the present invention has high initial adhesion to plastic members such as polyphenylene sulfide (PPS) or metal members, and exhibits high holding power in durability tests including high temperature and high humidity tests,
  • the resin composition which can suppress the deformation
  • the present invention provides an active energy ray-curable resin composition that has good workability such as syringe applicability and can be cured in a short time when irradiated with ultraviolet light.
  • FIG. 1 is an apparatus for measuring deformation of an adhesive part during heating of a curable composition of the present invention from an angle change.
  • FIG. 2 is a diagram for measuring the change in angle by a tilt sensor after photocuring the curable composition of the present invention and removing the jig.
  • FIG. 3 is a schematic diagram of a penetration strength test of an adhesive structure bonded with the active energy ray-curable resin composition of the present invention.
  • the component (A) includes (a1) a linear or branched multimer having a glycerol derivative and an ether skeleton as a linking functional group, and (a2) a trimethylolpropane derivative and an ether skeleton having a linking functional group.
  • a linear or branched multimer thereof (a3) a monomer of a pentaerythritol derivative and a linear or branched multimer having an ether skeleton as a linking functional group, and (a4) an ether bond or an ester bond, And a polyfunctional acrylate compound containing 4 or more (meth) acryloyl groups in the molecule, selected from the group consisting of dendritic molecular compounds in which (meth) acryloyl groups are arranged at 4 or more terminals.
  • a component may be used individually, respectively, or may be used in combination of 2 or more type.
  • (meth) acrylate includes both acrylate and methacrylate
  • (meth) acryloyl group includes both acryloyl group and methacryloyl group.
  • a glycerol derivative, a trimethylolpropane derivative, a pentaerythritol derivative, and a linear or branched multimer having an ether skeleton as a linking functional group include a glycerol unit, a trimethylolpropane unit, and a pentaerythritol in the molecule.
  • the unit contains 4 or more (meth) acryloyl groups in the molecule.
  • the glycerol unit is a structure obtained by removing three hydroxy groups from glycerol
  • the trimethylolpropane unit is a structure obtained by removing three hydroxy groups from trimethylolpropane
  • the pentaerythritol unit is a pentaerythritol unit. It is a structure in which four hydroxy groups are removed from the erythritol unit.
  • the glycerol derivative, trimethylolpropane derivative, and pentaerythritol derivative are compounds in which glycerol, trimethylolpropane, and pentaerythritol are substituted with four or more (meth) acryloyl groups.
  • the ether skeleton that is a linking functional group is an ether bond formed by condensation of two hydroxy groups between glycerol, trimethylolpropane, and pentaerythritol molecules, glycerol, trimethylolpropane, or It is a polyether skeleton formed by condensation of pentaerythritol and a dialcohol compound such as ethylene glycol.
  • the ether skeleton which is a linking functional group has the following general formula (1): —O— (X—O—) n1 ⁇ (1) (Where X is alkylene having 1 to 4 carbon atoms, n1 is 0 or an integer of 1 to 3) Indicated by
  • alkylene having 1 to 4 carbon atoms examples include methylene, ethylene, trimethylene, and tetramethylene, and ethylene is preferable.
  • n1 is preferably 0. That is, the ether skeleton in the present invention is preferably an ether bond (—O—).
  • a multimer of linear glycerol derivatives having an ether skeleton as a linking functional group has the following general formula (2): (Where n2 is 2 to 10, R 1 is hydrogen, acryloyl, or methacryloyl; R 2 is hydrogen or methyl; (However, the total of acryloyl and methacryloyl is 4 or more) The compound shown by these is preferable.
  • a linear or branched multimer having an ether skeleton as a linking functional group is represented by the general formula (5): (Where R 3 is hydrogen or methyl; n4 is 1 to 5, (However, the total of acryloyl and methacryloyl is 4 or more)
  • the compound shown by is especially preferable.
  • n4 is more preferably 3-4.
  • the polyfunctional acrylate compound multimerized in a branched form in which a branched structure exists by a linking functional group is a glycerol derivative, a trimethylolpropane derivative, and a pentaerythritol derivative, branched using an ether skeleton as a linking functional group.
  • a linking functional group is a compound that is multimerized in the shape.
  • Such a multimer is, for example, a compound in which hydroxy groups are removed from glycerol, trimethylolpropane, and pentaerythritol, which are multimerized via a linking functional group that is an ether skeleton, and (meth) acryloyl It is a compound having 4 or more groups.
  • the structure of pentaerythritol contained in a polyfunctional acrylate compound in which a pentaerythritol derivative is branched and polymerized via a linking functional group has the following formulas (6a) to (6d): (Wherein R 1 is as defined above) Indicated by
  • the compound that is a branched multimer of pentaerythritol derivatives is a structure in which the structures represented by the formulas (6a) to (6d) are randomly bonded via an ether skeleton (however, (Excluding linearly branched multimers in which the structure represented by formula (6b) is bound only in a straight line and the structure represented by formula (6a) is bound to the terminal).
  • the compound which is a branched multimer of pentaerythritol derivatives bonded at random may have any structure, for example, a cyclic structure or a network structure.
  • a branched multimer of a pentaerythritol derivative for example, the general formula (7): (Where n5 is 1 to 10, n6 is 0 to 10, R 1 is as defined in the general formula (2), R 2 represents the general formula (8) or the general formula (9): (Where n7 is 1 to 10, R 1 is as defined in the general formula (2)) (Where R 1 is as defined in the general formula (2), n8 is 1 to 10, n9 is 0 to 10, R 4 is a group represented by the general formula (8)) And However, the total of acryloyl group and methacryloyl group in one molecule is 4 or more) The compound shown by these is mentioned. Examples of such branched multimers of pentaerythritol having an ether bond as a linking functional group include V # Star-501 (produced by Osaka Organic Chemical Co., Ltd.).
  • a polyfunctional compound containing 4 or more (meth) acryloyl groups in the molecule which is a dendritic molecular compound containing an ether bond or an ester bond and having a (meth) acryloyl group arranged at 4 or more terminals.
  • An acrylate compound is a compound having a chemical structure composed of a core and a dendritic structure including a branching unit. Examples of such a compound include a dendrimer type acrylate compound.
  • the first generation is defined from the core to the first dendritic structure and its terminal portion.
  • the second generation is defined from the next dendrite structure to its end.
  • the next generation to the end is defined as the next generation.
  • the preferred generation number in the dendrimer of the present invention is in the range of 1 to 5, more preferably 1 to 3.
  • examples of the core of the dendritic molecular compound include trimethylolpropane, pentaerythritol, and dipentaerythritol.
  • the repeating number s in the general formula (10) corresponds to the generation number of the dendrimer compound.
  • the number of repetitions s in the general formula (10) is 2, the following (10a): (Where R 1 is as defined in the general formula (2)) Indicated by
  • a dendritic molecular compound containing an ether bond or an ester bond and having a (meth) acryloyl group at the terminal is represented by the following formula (11): ⁇ Where, n10 is independently an integer of 1 to 3, R 4 , independently of one another, is hydrogen, acryloyl, methacryloyl, or general formula (10): (Where R 1 and s are as defined above) And However, the total of acryloyl and methacryloyl is 4 or more ⁇ The compound shown by these is preferable.
  • a polyfunctional acrylate compound containing four or more (meth) acryloyl groups in the molecule which is a dendritic molecular compound containing an ether bond or an ester bond and having a (meth) acryloyl group disposed at the end
  • V # 1000 a compound of general formula (11) having a molecular weight of 2800, manufactured by Osaka Organic Chemical Co., Ltd.
  • the molecular weight is a number average molecular weight calculated in terms of polystyrene by gel permeation chromatography (GPC).
  • examples of a method for synthesizing a dendritic compound having a dendrimer structure include a divergent method in which the synthesis proceeds from the central core toward the outside, and a convergent method in which the synthesis proceeds from the outside toward the core.
  • Synthetic methods are known to those skilled in the art and are described, for example, in JP-A-11-60540.
  • a first-generation dendritic compound is produced by reacting a polyester polyol compound obtained by reacting dipentaerythritol with 2,2-dimethylolpropionic acid with (meth) acrylic acid. Can do.
  • a second-generation dendritic compound can be produced by further reacting the polyester polyol compound with 2,2-dimethylolpropionic acid and then reacting with (meth) acrylic acid.
  • the component (A) is preferably 0.01 to 25% by weight, preferably 0.5 to 10% by weight, based on the weight of the components (A) to (D).
  • the photocurable prepolymer which is the component (B) is a base resin (base oligomer) of the adhesive composition, and a (meth) acryloyl group which is a reactive group is formed by irradiation with active energy rays such as ultraviolet rays. It is a photosensitive resin that polymerizes.
  • the component (B) is a transparent low-hygroscopic resin and has a very low polarity and molecular structure, and therefore is a component that blocks oil and water from entering the outer periphery of the joint surface.
  • the (B) photocurable prepolymer of the present invention has one or more (meth) acryloyl groups, polybutadiene, polyisoprene, polybutadiene or polyisoprene hydrogenated product, polybutadiene or polyisoprene carboxyl-modified modified product , Having one or more main chain skeletons selected from the group consisting of polyester skeletons via a urethane bond, and having one or more (meth) acryloyl groups at the end or side chain of the main chain skeleton, (meth) Examples include acryloyl group-containing oligomers.
  • the photocurable prepolymer preferably has a main chain skeleton selected from the group consisting of polybutadiene or a hydrogenated product of polybutadiene, particularly preferably a hydrogenated product of polybutadiene.
  • the (B) photocurable prepolymer preferably has two or more (meth) acryloyl groups, and particularly preferably has (meth) acryloyl groups at both ends of the main chain skeleton.
  • (B) component may be used individually, respectively, or may be used in combination of 2 or more type.
  • the molecular weight of the (B) component photocurable prepolymer is usually 400 to 200,000, preferably 800 to 100,000, and more preferably 1,000 to 30,000. If it is such molecular weight, a viscosity becomes an appropriate range, the applicability
  • the photocurable prepolymer of component (B) is commercially available from Nippon Soda Co., Ltd. “NISSO-PB TEAI-1000” (both terminal acrylate-modified hydrogenated butadiene oligomer), Nippon Soda Co., Ltd.
  • NISSO-PB TE- 2000 both end methacrylate modified butadiene oligomer
  • Kuraray“ UC-203 ” an esterified oligomer of maleic anhydride adduct of isoprene polymer and 2-hydroxyethyl methacrylate
  • “ UA- ” manufactured by Kagawa Chemical 1 "(terminal urethane acrylate-modified polybutadiene hydrogenated product) and the like.
  • the component (B) is preferably 25 to 60% by weight, more preferably 30 to 50% by weight based on the weight of the components (A) to (D).
  • the monofunctional or bifunctional (meth) acryloyl group-containing monomer ((meth) acrylate monomer), which is the component (C), is a reactive diluent, and solidifies the base resin during curing. It is also a component that exhibits excellent adhesion to the body.
  • Component (C) includes (meth) acrylates having polar groups, such as (meth) acrylates containing hydroxyl groups, (meth) acrylates containing carboxyl groups, and acrylates containing amino groups; low-polar molecular structures Examples thereof include (meth) acrylate monomers such as aliphatic (meth) acrylate monomers, alicyclic (meth) acrylate monomers, and aromatic (meth) acrylate monomers.
  • (meth) acrylate monomers may be monofunctional (meth) acrylate monomers or bifunctional (meth) acrylate monomers, each of which may be used alone or in combination. A combination of the above may also be used.
  • Examples of the (meth) acrylate monomer containing a hydroxyl group include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) ) Acrylate, 2- (meth) acryloyloxyethyl-2-hydroxypropyl phthalate, and glycerol mono (meth) acrylate.
  • Examples of the (meth) acrylate monomer containing a carboxyl group include 2- (meth) acryloyloxyethyl succinic acid, 2- (meth) acryloyloxyethyl phthalic acid, and 2- (meth) acryloyloxyethyl hexahydrophthalic acid. It is done.
  • Examples of the (meth) acrylate monomer containing an amino group include diethylaminoethyl (meth) acrylate and dimethylaminomethyl (meth) acrylate.
  • Examples of the aliphatic (meth) acrylate include lauryl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isodecyl (meth) acrylate, stearyl (meth) acrylate, and 1,6-hexanediol (meth) acrylate.
  • Examples of the aromatic (meth) acrylate include benzyl (meth) acrylate.
  • the alicyclic (meth) acrylate is a (meth) acrylate having a monocyclic or polycyclic alicyclic hydrocarbon group having 3 to 20 carbon atoms, such as cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, Examples include dicyclopentenyloxyethyl (meth) acrylate, dicyclopentadienyl (meth) acrylate, tricyclodecanyl (meth) acrylate, norbornyl (meth) acrylate, and the like.
  • These monofunctional or bifunctional (meth) acryloyl group-containing monomers are “SA-1002” (manufactured by Mitsubishi Chemical Corporation), “Kayarad R-684” (manufactured by Nippon Kayaku), “light ester BZ”, “light Examples of commercially available products include “Ester IB-X”, “Light Ester HO”, “Light Ester HO-MS” (all “Light Ester” are manufactured by Kyoeisha Chemical Co., Ltd.).
  • the component (C) is preferably 25 to 70% by weight, more preferably 40 to 60% by weight based on the weight of the components (A) to (D).
  • the component (D) is a photopolymerization initiator.
  • the photopolymerization initiator include an ultraviolet polymerization initiator and a visible light polymerization initiator, both of which are used without limitation.
  • examples of the ultraviolet polymerization initiator include benzoin, benzophenone, and acetophenone
  • examples of the visible light polymerization initiator include acylphosphine oxide, thioxanthone, metallocene, and quinone.
  • the ultraviolet polymerization initiator include benzophenone polymerization initiators such as benzophenone, 4-phenylbenzophenone, benzoylbenzoic acid, and bisdiethylaminobenzophenone; acetophenone polymerization initiators such as 2,2-diethoxyacetophenone; Benzoin polymerization initiators such as benzyl, benzoin, and benzoin isopropyl ether; alkylphenone polymerization initiators such as benzyldimethyl ketal; thioxanthone polymerization initiators such as thioxanthone; 1-hydroxycyclohexyl phenyl ketone, 1- (4-isopropyl Phenyl) 2-hydroxy-2-methylpropan-1-one, 1- (4- (2-hydroxyethoxy) -phenyl) -2-hydroxy-2-methyl-1-propan-1-one, and 2- Dorokishi -2-methyl-1-hydroxyalkyl phenone polymerization initiators such as
  • visible light polymerization initiators examples include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide, and bis (2,6-dimethoxybenzoyl) -2,4.
  • Acylphosphine oxide photoinitiators such as 1,4-trimethyl-pentylphosphine oxide; camphorquinone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropan-1-one, and 2-benzyl And ketone polymerization initiators such as -2-dimethylamino-1- (4-morpholinophenyl) -1-butanone-1.
  • (D) photopolymerization initiator is preferably 1-hydroxycyclohexyl phenyl ketone (IRGACURE184, manufactured by Ciba Specialty Chemicals) and bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide. (IRGACURE819, manufactured by Ciba Specialty Chemicals).
  • the component (D) is preferably 0.1 to 10% by weight, more preferably 0.5 to 5% by weight, based on the weight of the components (A) to (D).
  • the energy ray curable resin composition of the present invention is an inorganic filler, an antioxidant, a polymerization inhibitor, a plasticizer, an organic filler, an acrylic rubber, a urethane rubber, and other elastomers, methacrylic compounds, as long as the object of the present invention is not impaired.
  • Graft copolymers such as acid methyl-butadiene-styrene graft copolymers and acrylonitrile-butadiene-styrene graft copolymers, solvents, extenders, reinforcing materials, thickeners, dyes, pigments, flame retardants and surface activity
  • An additive such as an agent and a thermal polymerization initiator can be used.
  • the curable composition of the present invention can further contain an inorganic filler as the component (E) for the purpose of further imparting high hardness, resin rigidity and low curing shrinkage.
  • inorganic fillers examples include silica powder such as quartz, quartz glass, fused silica, and spherical silica, and oxides such as spherical alumina, crushed alumina, magnesium oxide, beryllium oxide, and titanium oxide, boron nitride, silicon nitride, and aluminum nitride.
  • Nitrides such as silicon carbide, carbides such as silicon carbide, hydroxides such as aluminum hydroxide and magnesium hydroxide, metals and alloys such as copper, silver, iron, aluminum, nickel, titanium, diamond, carbon, etc.
  • carbon fillers composed of composite oxides. These inorganic fillers can be used alone or in combination of two or more.
  • Inorganic fillers are readily available, and commercially available products include glass fillers (“CF0023-05C” manufactured by Nippon Frit Co., Ltd.), amorphous silica (“Seahoster KE-P250” manufactured by Nippon Shokubai Co., Ltd.), fumed silica ( Thixotropic agent) (“TG308F” manufactured by Cabot Specialty Chemicals), and spherical silica (“CF0018-WB15C” manufactured by Nippon Frit).
  • glass fillers (“CF0023-05C” manufactured by Nippon Frit Co., Ltd.)
  • amorphous silica (“Seahoster KE-P250” manufactured by Nippon Shokubai Co., Ltd.)
  • fumed silica ( Thixotropic agent) (“TG308F” manufactured by Cabot Specialty Chemicals)
  • spherical silica (“CF0018-WB15C” manufactured by Nippon Frit).
  • a light control glass filler made of a complex oxide having a refractive index adjusted is preferable, and in this case, a spherical shape is preferable so as not to increase the viscosity.
  • the component (E) is preferably 70 to 300 parts by weight, more preferably 100 to 250 parts by weight, with respect to 100 parts by weight of the total of the components (A) to (D).
  • the curable composition of the present invention can further contain an antioxidant as the component (F) for the purpose of stability of the composition.
  • antioxidants examples include phenolic antioxidants, hydroquinone antioxidants, and other antioxidants, and phenolic antioxidants are preferable.
  • phenolic antioxidants examples include 2,2-methylene-bis (4-methyl-6-tertiarybutylphenol), catechol, picric acid, tertiary butylcatechol, 2,6-ditertiarybutyl-p-cresol, and 4,4′-thiobis [ethylene (oxy) (carbonyl) (ethylene)] bis [2,6-bis (1,1-dimethylethyl) phenol].
  • Hydroquinone antioxidants include ⁇ -naphthoquinone, 2-methoxy-1,4-naphthoquinone, methylhydroquinone, hydroquinone, hydroquinone monomethyl ether, monotertiary butylhydroquinone, 2,5-ditertiarybutylhydroquinone, p-benzoquinone, 2 , 5-diphenyl-p-benzoquinone, and 2,5-ditertiarybutyl-p-benzoquinone.
  • antioxidants examples include citric acid, phenothiazine, and 2-butyl-4-hydroxyanisole.
  • IRGANOX 1010 and IRGANOX 1035FF are listed as commercial products.
  • the component (F) is preferably 0.01 to 5 parts by weight and more preferably 0.1 to 2 parts by weight with respect to 100 parts by weight of the total of the components (A) to (D).
  • the curable composition of the present invention can further contain a polymerization inhibitor as the component (G).
  • polymerization inhibitor examples include phenol polymerization inhibitors and phenothiazine polymerization inhibitors.
  • phenolic polymerization inhibitors examples include 2,2-methylene-bis (4-methyl-6-tertiarybutylphenol) (BHT), catechol, picric acid, tertiary butylcatechol, 2,6-ditertiarybutyl-p- Cresol, and 4,4′-thiobis [ethylene (oxy) (carbonyl) (ethylene)] bis [2,6-bis (1,1-dimethylethyl) phenol].
  • phenothiazine polymerization inhibitor examples include phenothiazine, bis ( ⁇ -methylbenzyl) phenothiazine, 3,7-dioctylphenothiazine, and bis ( ⁇ , ⁇ -dimethylbenzyl) phenothiazine.
  • phenolic polymerization inhibitors such as BHT can also be used as an antioxidant.
  • the component (G) is preferably 0.01 to 3 parts by weight and more preferably 0.05 to 1 part by weight with respect to 100 parts by weight as a total of the components (A) to (D).
  • the curable composition of the present invention may contain (H) a plasticizer for the purpose of further improving the adhesiveness and adhesion durability and improving the heat resistance of the cured product.
  • a plasticizer an oligomer obtained by epoxidizing an unsaturated bond of polybutadiene is desirable, and commercially available products include BF-1000 (manufactured by ADEKA) or PB-3600 (manufactured by Daicel Industrial Chemical).
  • the component (H) is preferably 0.01 to 20 parts by weight, and 0.1 to 10 parts by weight with respect to 100 parts by weight as a total of the components (A) to (D). Is more preferable.
  • the active energy ray-curable resin composition of the present invention can contain (I) an organic filler for the purpose of further reducing the curing shrinkage rate.
  • organic fillers include acrylic fillers, styrene fillers, acrylic / styrene copolymer fillers, fluororesin fillers, polyethylene fillers, and polypropylene fillers, and commercially available products such as “PPW-5” (polypropylene fillers, Seishin companies). And “propyl mat 31” (polypropylene filler, manufactured by MICROPOWDERS, INC.). Each may be used alone or in combination of two or more.
  • a preferred organic filler is a polypropylene filler with less swelling.
  • the component (I) is preferably 0.01 to 20 parts by weight, preferably 0.1 to 10 parts by weight with respect to 100 parts by weight as the total of the components (A) to (D). Is more preferable.
  • the curable composition of the present invention can further contain a silane coupling agent for the purpose of further improving the adhesion to the glass surface.
  • silane coupling agents ⁇ -chloropropyltrimethoxysilane, vinyltrimethoxysilane, vinyltrichlorosilane, vinyltriethoxysilane, vinyl-tris ( ⁇ -methoxyethoxy) silane, ⁇ -methacryloxypropyltrimethoxysilane, ⁇ -Acryloxypropyltrimethoxysilane, ⁇ - (3,4-epoxycyclohexyl) ethyltrimethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -mercaptopropyltrimethoxysilane, ⁇ -aminopropyltriethoxysilane, N - ⁇ - (aminoethyl) - ⁇ -aminopropyltrimethoxysilane, N- ⁇ - (aminoethyl) - ⁇ -aminopropylmethyldimethoxysilane, ⁇ -ure
  • the content of the silane coupling agent is preferably 0 to 10 parts by weight with respect to 100 parts by weight in total of the components (A) to (D).
  • the silane coupling agent tends to be produced as an outgas component during a heat resistance test after curing of the curable composition
  • the curable composition containing no silane coupling agent that is, the components (A) to (D). It is desirable that the content of the silane coupling agent is 0 part by weight with respect to the total weight.
  • the cured product of the active energy ray-curable resin composition is obtained by curing the active energy ray-curable resin composition of the present invention.
  • the method of curing the active energy ray-curable resin composition of the present invention includes a step of irradiating the active energy ray-curable resin composition of the present invention with active energy rays.
  • the wavelength of the active energy ray is not particularly limited as long as the active energy ray-curable resin composition of the present invention is cured, and is 100 to 420 nm, more preferably 300 to 420 nm.
  • the active energy ray-curable resin composition of the present invention is an adhesive composition and is useful as an adhesive, particularly an adhesive for bonding optical parts.
  • a metal, a metal plated member, a small part made of plastic or the like can be cited.
  • metals constituting small parts include Mg, Zn, Ni, and Al.
  • Plastics include liquid crystal polymer (LCP), cycloolefin polymer (COP), cycloolefin copolymer (COC), polyphenylene sulfide (PPS), and polyphenylene. Examples thereof include oxide (PPO) or a composite plastic material obtained by kneading glass fiber or carbon fiber with the plastic material. Plastic materials are available as commercial products. Examples of PPS include “Idemitsu PPS” manufactured by Idemitsu Co., Ltd.
  • optical pickup components require different fixing accuracy requirements depending on the component.
  • components with high accuracy requirements such as a photodetector (PD), a laser diode (LD), a condenser lens (NAL), etc. , Half mirror (beam splitter) (HM (PBS)), parts with high accuracy requirements such as skew, parts with high accuracy requirements such as reflection mirror (RM), objective lens (OBL), collimator lens
  • PD photodetectors
  • LD laser diodes
  • NAL condenser lens
  • HM Half mirror
  • RM reflection mirror
  • ONL objective lens
  • collimator lens there are parts with slightly low high accuracy requirements.
  • the curable composition of the present invention includes a polyfunctional acrylate compound, a photocurable prepolymer that is a diene-based or hydrogenated diene-based (meth) acrylate, a reaction-dilutable (meth) acrylate having various functional groups, And having a specific composition containing a photopolymerization initiator, it can be cured in a short time by irradiating with active energy rays, and it can be applied to plastic members such as polyphenylene sulfide (PPS) or metal members. It has a characteristic of having high initial adhesiveness and exhibiting high holding power in durability tests such as a high temperature and high humidity test.
  • PPS polyphenylene sulfide
  • the deformation at the time of heat and the deformability to the load at the time of heat can be suppressed very little. For this reason, the movement of the part after hardening adhere
  • Light Ester IB-X (C-4) 2-hydroxyethyl methacrylate (“Light Ester HO” manufactured by Kyoeisha Chemical Co., Ltd.), (C-5) 2-Methacryloyloxyethyl succinic acid (“Light Ester HO-MS” manufactured by Kyoeisha Chemical Co., Ltd.)
  • D Photopolymerization initiator (D-1) 1-hydroxycyclohexyl phenyl ketone (“IRGACURE184” manufactured by Ciba Specialty Chemicals) (D-2) Bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide (“IRGACURE819” manufactured by Ciba Specialty Chemicals)
  • F Antioxidant (F-1) (“IRGANOX10
  • UV light of 250 mW / cm 2 was irradiated for 12 seconds using a UV irradiator 3 from a distance of 45 degrees and 20 mm, and fixed. Subsequently, the base 5 was removed and it was set as the sample for evaluation.
  • the amount of change in angle after temperature adjustment was measured and set to zero.
  • the temperature cycle was held at 25 ° C. for 1 hour, then the temperature was raised from 25 ° C. to 60 ° C. in 30 minutes, reached 60 ° C. and then held at 60 ° C. for 1 hour, and further 60 ° C. in 30 minutes.
  • the temperature was raised from 80 ° C. to 80 ° C., reached 80 ° C., held at 80 ° C. for 1 hour, and lowered from 80 ° C. to 25 ° C. in 30 minutes to form one cycle.
  • the temperature in the thermostat was changed to 25 ° C., 60 ° C., and 80 ° C.
  • the amount of change in angle was determined after holding at 60 ° C. and 80 ° C. for 1 hour and after holding at 25 ° C. for 1 hour after 1 cycle. Note that the amount of change in angle in the table is in minutes.
  • Adhesion test The adhesion test was measured by punching adhesive strength. As shown in FIG. 3, PPS (polyphenylene sulfide, Idemitsu PPS NT7790 (manufactured by Idemitsu Co., Ltd.)) and end-polished aluminum chip (Engineering Test Service Co., Ltd., A5052P, length 10 mm ⁇ width 10 mm ⁇ height 2 mm), dispenser Using an adjuster (ML-606, manufactured by Musashi Engineering Co., Ltd.), 0.0025 cc of active energy ray-curable resin composition was applied using a syringe, and then a UV irradiator (manufactured by Hamamatsu Photonics, LC6) was applied from a distance of 20 mm.
  • PPS polyphenylene sulfide, Idemitsu PPS NT7790 (manufactured by Idemitsu Co., Ltd.)
  • end-polished aluminum chip Engineing Test Service Co., Ltd., A5052
  • UV light of 250 mW / cm 2 was irradiated for 12 seconds using a UV illuminance meter (UIS-101, manufactured by USHIO INC.) And fixed.
  • UIS-101 UV illuminance meter
  • the adhesive test piece was produced.
  • a punching tester AGS-500D manufactured by Shimadzu Corporation
  • the punching strength was measured at a punching speed of 10 mm / min for a region having a diameter of 4 mm from the side where the chip was not fixed.
  • the one with a strength of 40 N or more and showing no state of floating was marked with ⁇ .
  • a similar test was performed with a PPS chip (length 10 mm ⁇ width 10 mm ⁇ height 2 mm) and a PPS plate, and with an aluminum chip and an aluminum plate (A5052P manufactured by Engineering Test Service Co., Ltd.) whose end surfaces were polished.
  • Examples 1 to 7 and Comparative Examples 1 and 2 Resin compositions were prepared by mixing the raw materials of the types shown in Tables 1 and 2 with the compositions shown in Tables 1 and 2. The obtained composition was subjected to adhesive strength measurement and moisture resistance, heat resistance, and heat shock resistance evaluation tests. The results are shown in Tables 1 and 2. In addition, content is a weight part.
  • the moisture resistance test was performed using LH21-21M (manufactured by Nagano Science Co., Ltd.) under the conditions of 65 ° C./95% RH-336 hours. The case where no peeling or cracking or crack at the end portion was observed, and the adhesive strength was 40 N or more was rated as ⁇ .
  • the heat resistance was measured using LC-112 (Espec) at 80 ° C. for 336 hours. The case where no peeling or cracking or crack at the end portion was observed, and the adhesive strength was 40 N or more was rated as ⁇ .
  • the heat shock resistance evaluation test was performed under the condition of 100 cycles of ⁇ 40 ° C. (30 minutes) / 85 ° C. (30 minutes) using TSA-41L (Espec). The case where no peeling or cracking or crack at the end portion was observed, and the adhesive strength was 40 N or more was rated as ⁇ .
  • the curable composition of the present invention can fix, for example, an optical component such as an LD, a photodetector, a lens, and a prism, or an optical module on which an optical component such as a lens is mounted, with high fixing accuracy.
  • an optical component such as an LD, a photodetector, a lens, and a prism
  • an optical module on which an optical component such as a lens is mounted with high fixing accuracy.

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  • Chemical & Material Sciences (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
PCT/JP2012/050435 2011-01-12 2012-01-12 多官能アクリレート化合物を含む活性エネルギー線硬化性樹脂組成物 WO2012096330A1 (ja)

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WO2016024357A1 (ja) * 2014-08-14 2016-02-18 電気化学工業株式会社 エネルギー線硬化性接着剤
JP6481167B2 (ja) * 2015-04-09 2019-03-13 協立化学産業株式会社 光硬化型接着組成物
JP6896383B2 (ja) * 2016-07-22 2021-06-30 東京応化工業株式会社 感光性樹脂組成物、硬化膜、カラーフィルタ、及び硬化膜の製造方法
WO2019071564A1 (en) * 2017-10-13 2019-04-18 Henkel Ag & Co. Kgaa UV-CURABLE ADHESIVE COMPOSITION
KR102184587B1 (ko) * 2019-02-28 2020-12-01 주식회사 케이씨씨 접착제 조성물
CN111057514B (zh) * 2019-12-23 2021-11-19 烟台信友新材料有限公司 一种高强度耐湿热光固化胶黏剂及其制备方法
CN116368197A (zh) 2020-10-29 2023-06-30 电化株式会社 固化性组合物、物品、确认方法及粘接剂组合物
JP2024521726A (ja) * 2021-05-21 2024-06-04 ケアフュージョン ３０３、インコーポレイテッド 医療用デバイスにおける異種材料結合用接着剤
JP2023055304A (ja) 2021-10-06 2023-04-18 日本化薬株式会社 ポリアミドイミド（メタ）アクリレート樹脂、それを用いた活性エネルギー線硬化型樹脂組成物及びその硬化物

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