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WO2016039277A1 - Composition et procédé de démontage - Google Patents

Composition et procédé de démontage Download PDF

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Publication number
WO2016039277A1
WO2016039277A1 PCT/JP2015/075264 JP2015075264W WO2016039277A1 WO 2016039277 A1 WO2016039277 A1 WO 2016039277A1 JP 2015075264 W JP2015075264 W JP 2015075264W WO 2016039277 A1 WO2016039277 A1 WO 2016039277A1
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WO
WIPO (PCT)
Prior art keywords
meth
acrylate
mass
composition according
composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2015/075264
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English (en)
Japanese (ja)
Inventor
泰則 石田
啓之 栗村
佑基 比舎
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Denka Co Ltd
Original Assignee
Denki Kagaku Kogyo KK
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Denki Kagaku Kogyo KK filed Critical Denki Kagaku Kogyo KK
Priority to JP2016547422A priority Critical patent/JP6667442B2/ja
Publication of WO2016039277A1 publication Critical patent/WO2016039277A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • 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 composition.
  • the present invention relates to, for example, a (meth) acrylic resin composition.
  • the present invention also relates to an adhesive, a coating agent, and an easily disintegratable composition.
  • the present invention relates to a method for disassembling a complex.
  • photocurable resin compositions such as ultraviolet curable and visible light curable have been used in the production of various electronic components, optical components and optical devices.
  • various forms such as adhesion, potting, coating, sealing and molding.
  • (meth) acrylic, epoxy, oxetane, polyvinyl, polyene / polythiol, and the like are known.
  • (meth) acrylic type is most frequently used, and urethane (meth) acrylate type, epoxy (meth) acrylate type, polyester (meth) acrylate type, and the like are used depending on applications.
  • polyene / polythiol systems are used together with (meth) acrylic systems such as urethane (meth) acrylate systems as long as they are used for joining optical components and optical devices.
  • heat resistance during production can be mentioned as a particularly required item.
  • vapor deposition at a high temperature exceeding 200 ° C. or baking at a high temperature may be performed.
  • optical components such as image sensors can be surface-mounted on a circuit board, and in this case, they are passed through high-temperature solder reflow.
  • the temperature conditions for solder reflow have become stricter.
  • the location where the photocurable resin composition is used is sufficiently resistant to high-temperature heat treatment in order to improve the quality of optical components and optical devices, or to increase productivity and production yield. Is done. For example, it is necessary that peeling, foaming, cracking, discoloration, and the like do not occur during high temperature heat treatment.
  • the outgas generated during the high-temperature heat treatment may cause local contamination of components and devices, or the characteristics of components and devices may be deteriorated due to outgas generated during manufacturing and use after manufacturing. is there.
  • the problem of characteristic deterioration due to outgassing has become prominent.
  • Patent Document 1 does not find any knowledge about the component (C) according to the present invention described later, and the mass of (A) / (C) regarding the component (A) and component (C) of the present invention described later. There is no description or suggestion that the ratio should be (3-8) / 1.
  • a polyimide-based adhesive having excellent peel adhesive strength is disclosed as a heat-resistant adhesive, but since it is heat-cured, it takes time to cure and is inferior in productivity (see Patent Document 2).
  • the main chain skeleton is at least one selected from the group consisting of polybutadiene, polyisoprene, and hydrogenated products thereof, and at least one (meth) acryloyl group at the terminal or side chain of the main chain skeleton.
  • An energy ray-curable resin composition containing a (meth) acrylate, a photopolymerization initiator, and an antioxidant is disclosed, but no heat resistance is described (see Patent Document 4).
  • Patent Document 4 does not describe the component (B) of the present invention described later.
  • an adhesive composition containing a polyfunctional (meth) acrylate, a monofunctional (meth) acrylate, and a photopolymerization initiator, and a glass transition temperature of a cured product obtained from the adhesive composition is ⁇ 50 ° C.
  • an adhesive composition characterized by a temperature of ⁇ 40 ° C. is disclosed, there is no description about increasing the glass transition temperature of the cured product and obtaining sufficient heat resistance (see Patent Document 5).
  • Patent Document 5 neither describes nor suggests that the mass ratio of (A) / (C) should be (3 to 8) / 1 with respect to the components (A) and (C) of the present invention described later. .
  • the polyfunctional (meth) acrylate contains a photopolymerization initiator having a heating mass reduction rate of 15% by mass or less when the temperature is increased from 30 ° C. to 250 ° C. at a rate of temperature increase of 10 ° C./min in a nitrogen stream.
  • a (meth) acrylic resin composition, and a (meth) acrylic resin composition in which the glass transition temperature of a cured product obtained from the composition is 250 ° C. or higher is disclosed.
  • B) component (refer patent document 6).
  • the present invention finds a design that can withstand the expansion and contraction of the adherend in a high temperature reliability test, for example.
  • Patent Document 7 does not suggest mixing all of the component (A), the component (B) and the component (C), or the mixing ratio of the component (A) and the component (C) of the present invention.
  • the substrates are bonded together using an adhesive composition containing one or more (meth) acrylates having one or more (meth) acryloyl groups, and the adhesive composition is cured.
  • a method for disassembling an adhesive body comprising a step of irradiating an excimer light having a central wavelength of 1 to 300 nm to an adhesive body formed by the process, wherein at least one base material is transparent to the excimer light is disclosed.
  • Patent Document 8 there is no suggestion about blending all of the (A) component, the (B) component, and the (C) component, or the blending ratio of the (A) component and the (C) component of the present invention.
  • the present invention is capable of peeling without using excimer light having high energy for the peeling method.
  • JP 2006-342222 A Japanese Patent No. 3014526 Japanese Patent No. 3934701 International Publication No. 2006/129678 Pamphlet International Publication No. 2008/018252 Pamphlet International Publication No. 2011/049138 Pamphlet JP 2010-248353 A International Publication No. 2011/158654 Pamphlet
  • the present invention has been completed as a result of various studies to solve the problem of improving heat resistance and outgassing properties, for example.
  • the present invention is a composition containing the following (A) to (D), wherein the mass ratio of (A) / (C) is (3 to 8) / 1.
  • (B) is (B1) a phenoxy (poly) alkylene oxide (meth) acrylate having an alkylene oxide chain.
  • (B) is (B2) an alkyl (meth) acrylate having an alkyl group having 8 to 20 carbon atoms.
  • composition according to the present invention (A) 45 to 75 parts by mass, (B) 10 to 50 parts by mass in 100 parts by mass of the total amount of (A) to (C), C) 1 to 20 parts by mass is contained.
  • the amount of the (D) radical photopolymerization initiator used is 0.01 to 100 parts by mass with respect to 100 parts by mass of the total amount of (A) to (C). 5 parts by mass.
  • the photoradical polymerization initiator is 2-hydroxy-1- ⁇ 4- [4- (2-hydroxy-2-methyl-propionyl)- Benzyl] -phenyl ⁇ -2-methyl-propan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone-1,2-dimethylamino-2- (4-methyl-benzyl) ) -1- (4-morpholin-4-yl-phenyl) -butan-1-one, bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide Oxy-phenyl-acetic acid 2- [2-oxo-2-phenyl-acetoxy-ethoxy] -ethyl ester, oxy-pheny - acetate tic acid 2- [2-hydroxy - ethoxy] - at least one selected from
  • composition according to the present invention when the photo radical polymerization initiator is heated from 30 ° C. to 250 ° C. at a temperature rising rate of 10 ° C./min in a nitrogen stream, The mass reduction rate is 15% by mass or less.
  • composition according to the present invention when the photo radical polymerization initiator is heated from 30 ° C. to 250 ° C. at a temperature rising rate of 10 ° C./min in a nitrogen stream,
  • the mass reduction rate is 50% by mass or more.
  • composition according to the present invention it further contains a polymerization inhibitor.
  • an infrared absorber is further contained.
  • the present invention is an adhesive comprising the composition according to the present invention.
  • the present invention is a coating comprising the composition according to the present invention.
  • the present invention is an easily disassembleable composition comprising the composition according to the present invention.
  • the present invention is a composite formed by bonding substrates or covering substrates using the composition according to the present invention.
  • the present invention is a method for producing a composite comprising bonding substrates to each other or coating the substrates using the composition according to the present invention.
  • the method for producing a composite according to the present invention includes irradiating the composition according to the present invention with visible light or ultraviolet rays to bond the substrates together or coat the substrates.
  • Another aspect of the present invention is a method for disassembling an adhesive body, including bonding the substrates together using the composition according to the present invention, adhering them, and then peeling the obtained adhesive body.
  • the method for disassembling an adhesive body according to the present invention includes peeling the adhesive body obtained by applying an external force.
  • the method for disassembling an adhesive body according to the present invention includes peeling the adhesive body obtained by irradiating visible light or ultraviolet light.
  • the method for disassembling the covering according to the present invention includes coating the substrate using the composition according to the present invention, and then peeling the obtained covering.
  • the method for disassembling a covering according to the present invention includes peeling the composition from the obtained covering by applying an external force.
  • the method for disassembling a covering according to the present invention includes peeling the composition from the obtained covering by irradiating visible light or ultraviolet rays.
  • a cured product having excellent heat resistance and low outgassing properties can be obtained by the composition of the present invention.
  • the component (A) is one or more polyfunctional (meth) acrylates selected from the group consisting of diene (meth) acrylates, polyester urethane (meth) acrylates and polyether urethane (meth) acrylates. is there.
  • a polyfunctional (meth) acrylate oligomer / polymer having two or more (meth) acroylated oligomers / polymer terminals or side chains may be mentioned.
  • the polyfunctional (meth) acrylate refers to a compound having two or more (meth) acryloyl groups.
  • Diene (meth) acrylate refers to (meth) acrylate having a diene skeleton.
  • the diene (meth) acrylate include 1,2-polybutadiene-terminated urethane (meth) acrylate (for example, “TE-2000” and “TEA-1000” manufactured by Nippon Soda Co., Ltd.), polyisoprene-terminated (meth) acrylate, and isoprene polymerization.
  • an esterified oligomer of a maleic anhydride adduct of the product and 2-hydroxyethyl (meth) acrylate for example, “UC-203”, “UC-102” manufactured by Kuraray Co., Ltd.
  • diene-based (meth) acrylates a group consisting of 1,2-polybutadiene-terminated urethane (meth) acrylate and an esterified oligomer of 2-hydroxyalkyl (meth) acrylate and a maleic anhydride adduct of isoprene polymer One or more of these are preferred.
  • Polyester urethane (meth) acrylate refers to (meth) acrylate having a polyester skeleton.
  • Examples of the polyester urethane (meth) acrylate include “UV-2000B”, “UV-3000B”, “UV-7000B” manufactured by Nippon Gosei Co., Ltd., “KHP-11”, “KHP-17” manufactured by Negami Kogyo Co., Ltd. Is mentioned.
  • Polyether urethane (meth) acrylate refers to (meth) acrylate having a polyether skeleton.
  • polyether urethane (meth) acrylate examples include “UV-3700B” and “UV-6100B” manufactured by Nippon Gosei Co., Ltd.
  • a diene (meth) acrylate is preferable because of its great effect.
  • 1,2-polybutadiene-terminated urethane (meth) acrylate those represented by the following general formula (1) are preferable.
  • esterified oligomer of the maleic anhydride adduct of isoprene polymer and 2-hydroxyalkyl (meth) acrylate those represented by the following general formula (2) are preferable.
  • the urethane (meth) acrylate is a reaction between a polyol compound (hereinafter represented by X), a polyisocyanate compound (hereinafter represented by Y) and a hydroxy (meth) acrylate (hereinafter represented by Z) (for example, This refers to urethane (meth) acrylate having a urethane bond in the molecule, which is obtained by polycondensation reaction).
  • polyol compound (X) examples include ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, butylene glycol, 1,4-butanediol, polybutylene glycol, 1, 5-pentanediol, 1,6-hexanediol, 1,8-octanediol, 1,9-nonanediol, 3-methyl-1,5-pentanediol, 2,4-diethyl-1,5-pentanediol, 2,2-butylethyl-1,3-propanediol, neopentyl glycol, cyclohexanedimethanol, hydrogenated bisphenol A, polycaprolactone, trimethylolethane, trimethylolpropane, poly At least a polyhydric alcohol such as trimethylolpropane, pent
  • a polydiene type polyol 1 or more types in the group which consists of a polydiene type polyol, a polyether polyol, and a polyester polyol are preferable, and a polydiene type polyol is more preferable.
  • polydiene-based polyols polybutadiene polyol is preferred.
  • polystyrene-terminated urethane (meth) acrylate for example, polybutadiene polyol can be used, and polyol compound (X) used for polyester-based urethane (meth) acrylate.
  • polybutadiene polyol can be used
  • polyol compound (X) used for polyester-based urethane (meth) acrylate can be, for example, a polyester polyol
  • the polyol compound (X) used in the polyether-based urethane (meth) acrylate can be, for example, a polyether polyol.
  • the polyisocyanate compound (Y) is not particularly limited.
  • aromatic, aliphatic and alicyclic polyisocyanates can be used, among which tolylene diisocyanate (TDI) and diphenylmethane.
  • TDI tolylene diisocyanate
  • H-XDI hydrogenated xylylene diisocyanate
  • IPDI isophorone diisocyanate
  • hydroxy (meth) acrylate (Z) examples include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate and the like.
  • Hydroxyalkyl (meth) acrylate 2-hydroxyethyl (meth) acryloyl phosphate, 2- (meth) acryloyloxyethyl-2-hydroxypropyl phthalate, glycerin di (meth) acrylate, 2-hydroxy-3- (meth) acrylic Leuoxypropyl (meth) acrylate, caprolactone-modified 2-hydroxyethyl (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, caprolac Down-modified 2-hydroxyethyl (meth) acrylate. Of these, hydroxyalkyl (meth) acrylate is preferred.
  • hydroxyalkyl (meth) acrylates one or more members selected from the group consisting of 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, and 2-hydroxybutyl (meth) acrylate are preferable. Hydroxyethyl (meth) acrylate is more preferred.
  • the number average molecular weight of the component (A) is preferably 4000 to 60000, and more preferably 5000 to 40000.
  • the number average molecular weight is obtained by preparing a calibration curve with commercially available standard polystyrene using GPC system (SC-8010 manufactured by Tosoh Corporation) using tetrahydrofuran as a solvent under the following conditions. The measurement conditions used in the experimental examples are shown below. Flow rate: 1.0 ml / min Setting temperature: 40 ° C. Column configuration: “TSK guardcolumn MP ( ⁇ L)” manufactured by Tosoh Corp.
  • Amount of polyfunctional (meth) acrylate containing one or more of the group consisting of diene (meth) acrylate, polyester urethane (meth) acrylate and polyether urethane (meth) acrylate Is preferably 45 to 75 parts by mass, more preferably 50 to 70 parts by mass, in 100 parts by mass of the total amount of (A) to (C). If it is 45 mass parts or more, favorable heat resistance will be obtained, and if it is 75 mass parts or less, favorable curability will be obtained.
  • the component (B) is (B1) a phenoxy (poly) alkylene oxide (meth) acrylate having an alkylene oxide chain and / or (B2) an alkyl (meth) acrylate having an alkyl group having 8 to 20 carbon atoms.
  • monofunctional (meth) acrylate is preferable.
  • Monofunctional (meth) acrylate refers to a compound having one (meth) acryloyl group.
  • a (meth) acrylate represented by the following general formula (3) is preferable. In the formula, n represents a positive integer.
  • R 1 represents a hydrogen atom or a methyl group, and preferably a hydrogen atom.
  • R 2 represents an alkylene group, preferably an alkylene group having 2 to 3 carbon atoms, and most preferably an ethylene group having 2 carbon atoms.
  • R 3 represents a hydrogen atom or an alkyl group, preferably a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 20 carbon atoms, still more preferably an alkyl group having 6 to 12 carbon atoms, Most preferred is a nonyl group having 9 carbon atoms.
  • n is preferably 1 to 15, more preferably 1 to 3, and most preferably 1. These (meth) acrylates can be used alone or in combination of two or more.
  • R 3 is preferably a saturated aliphatic hydrocarbon group.
  • (B1) (Meth) acrylates in which R 3 is a nonyl group include nonylphenol ethylene oxide modified (meth) acrylate, nonylphenol (ethylene oxide 4 mol modified) (meth) acrylate, nonylphenol (ethylene oxide 8 mol modified) (meth) Examples include acrylate, nonylphenol (modified with 2.5 mol of propylene oxide) (meth) acrylate, and the like.
  • the alkyl (meth) acrylate having an alkyl group having 8 to 20 carbon atoms is preferably a (meth) acrylate represented by the following general formula (4).
  • Formula (4) Z-O-R 4 Z represents a (meth) acryloyl group.
  • R 4 represents a linear or branched alkyl group having 8 to 20 carbon atoms, more preferably an alkyl group having 10 to 16 carbon atoms, still more preferably an alkyl group having 11 to 14 carbon atoms, and an alkyl group having 12 carbon atoms. Most preferred.
  • These (meth) acrylates can be used alone or in combination of two or more.
  • R 4 is preferably a saturated aliphatic hydrocarbon group.
  • the alkyl (meth) acrylate having an alkyl group having 8 to 20 carbon atoms includes octyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, nonyl (meth) acrylate, isononyl (meth) acrylate, decyl (meth) ) Acrylate, isodecyl (meth) acrylate, stearyl (meth) acrylate, isostearyl (meth) acrylate, lauryl (meth) acrylate, tridecyl (meth) acrylate, tetradecyl (meth) acrylate, pentadecyl (meth) acrylate, hexadecyl (meth) Linear or branched alkyl groups such as acrylate, heptadecyl (meth) acrylate, octadecyl (meth) acrylate, nonade
  • (B) (B1) monofunctional (meth) containing phenoxy (poly) alkylene oxide (meth) acrylate having an alkylene oxide chain and / or (B2) alkyl (meth) acrylate having an alkyl group having 8 to 20 carbon atoms
  • the total amount of acrylate used is preferably 10 to 50 parts by mass, more preferably 20 to 45 parts by mass, out of 100 parts by mass of the total amount of (A) to (C). If it is 10 mass parts or more, favorable sclerosis
  • Component (C) is 1,3-adamantyl dimethanol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, isocyanuric acid ethylene oxide modified di (meth) acrylate, isocyanuric acid ethylene oxide modified tri (meth) acrylate, 1 selected from the group consisting of pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dimethylolpropane tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, and dipentaerythritol hexa (meth) acrylate.
  • one or more selected from the group consisting of 1,3-adamantyl dimethanol di (meth) acrylate, pentaerythritol tri (meth) acrylate, and pentaerythritol tetra (meth) acrylate are preferable, and pentaerythritol tri (
  • One or more selected from the group consisting of (meth) acrylates and pentaerythritol tetra (meth) acrylates are more preferable, and it is most preferable to use pentaerythritol tri (meth) acrylate and pentaerythritol tetra (meth) acrylate in combination.
  • pentaerythritol tri (meth) acrylate and pentaerythritol tetra (meth) acrylate are used in combination, the content ratio of pentaerythritol tri (meth) acrylate and pentaerythritol tetra (meth) acrylate is pentaerythritol tri (meth) acrylate and pentaerythritol.
  • the total amount of component (C) used is preferably 1 to 20 parts by mass, more preferably 2 to 15 parts by mass, in 100 parts by mass of the total amount of (A) to (C). If it is 1 mass part or more, favorable peelability will be obtained, and if it is 20 mass parts or less, there is no possibility that heat resistance will fall.
  • the mass ratio of (A) / (C) is preferably (3 to 8) / 1, more preferably (4 to 7) / 1, and (5 to 6.8). / 1 is more preferable, and (5.5 to 6.5) / 1 is most preferable. If the mass ratio of (A) / (C) is 3/1 or more, it has heat resistance. If the mass ratio of (A) / (C) is 8/1 or less, it has releasability.
  • the photopolymerization initiator is a photoradical polymerization initiator.
  • the heating mass reduction rate is 15% by mass or less. In this respect, it is preferably 8% by mass or less, and most preferably 6% by mass or less.
  • the heating mass reduction rate is preferably 0.1% by mass or more, and more preferably 4% by mass or more from the viewpoint of economy.
  • the (D) photopolymerization initiator having a heating mass reduction rate of 15% by mass or less includes 2-hydroxy-1- ⁇ 4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl] -phenyl.
  • ⁇ -2-Methyl-propan-1-one 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone-1,2-dimethylamino-2- (4-methyl-benzyl) -1- (4-morpholin-4-yl-phenyl) -butan-1-one, bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, oxy-phenyl -Acetic acid 2- [2-oxo-2-phenyl-acetoxy-ethoxy] -ethyl ester, oxy-phenyl-acetyl Acid 2- [2-hydroxy - ethoxy]
  • 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone-1,2-dimethylamino-2- (4-methyl-benzyl) is preferred in terms of heat resistance and low outgassing properties.
  • bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide More preferably, one or more of the group consisting of 2-dimethylamino-2- (4-methyl-benzyl) -1- (4-morpholin-4-yl-phenyl) -butan-1-one Most preferred.
  • the heating mass reduction rate of the photopolymerization initiator by the heating is, for example, from 30 ° C. to 250 ° C. with a temperature increase rate of 10 ° C./min in a nitrogen stream using a thermal mass spectrometer. Can be expressed as a mass reduction rate (mass%) at 250 ° C. with respect to the mass of the photopolymerization initiator at 30 ° C.
  • the amount of the photopolymerization initiator used is preferably 0.01 to 5 parts by mass with respect to 100 parts by mass of the total amount of (A) to (C). When it is 0.01 part by mass or more, sufficient curability is obtained, and when it is 5 parts by mass or less, low outgassing properties and heat resistance are excellent. In view of curability, low outgassing property, and heat resistance, 0.02 to 3 parts by mass is preferable, and 0.03 to 2 parts by mass is more preferable.
  • photopolymerization is initiated by heating at 250 ° C. relative to the mass of the photopolymerization initiator at 30 ° C.
  • the mass reduction rate of the agent is preferably 15% by mass or less. When it is 15% by mass or less, low outgas and heat resistance are excellent.
  • the amount of the (D) photopolymerization initiator having the mass reduction rate of 15% by mass or less is the total amount of (A) to (C) 100
  • the amount is preferably 0.02 to 3 parts by mass and more preferably 0.03 to 0.7 parts by mass with respect to the mass part.
  • the photopolymerization initiator when the photopolymerization initiator is heated from 30 ° C. to 250 ° C. at a rate of temperature increase of 10 ° C./min in a nitrogen stream, heating at 250 ° C. with respect to the mass of the photopolymerization initiator at 30 ° C. Even when the mass reduction rate of the photopolymerization initiator exceeds 15% by mass, or even when it is 50% by mass or more, it can be applied to the composition according to the present invention.
  • the amount of the photopolymerization initiator (D) having a mass reduction rate of 50% by mass or more is preferably 0.01 to 3 parts by mass with respect to 100 parts by mass of the total amount of (A) to (C). More preferred is 0.8 to 2 parts by mass. Examples of the photopolymerization initiator exceeding 15% by mass include 1-hydroxycyclohexyl phenyl ketone and benzyl dimethyl ketal.
  • a polymerization inhibitor can be used to improve the storage stability.
  • Polymerization inhibitors include methyl hydroquinone, hydroquinone, 2,2-methylene-bis (4-methyl-6-tertiary butylphenol), catechol, hydroquinone monomethyl ether, monotertiary butyl hydroquinone, 2,5-ditertiary butyl hydroquinone.
  • P-benzoquinone 2,5-diphenyl-p-benzoquinone, 2,5-ditertiarybutyl-p-benzoquinone, picric acid, citric acid, phenothiazine, tertiary butylcatechol, 2-butyl-4-hydroxyanisole and 2 , 6-ditertiary butyl-p-cresol and the like.
  • 2,2-methylene-bis (4-methyl-6-tertiarybutylphenol) is preferred. One or more of these may be used.
  • the amount of the polymerization inhibitor used is preferably 0.001 to 3 parts by mass, more preferably 0.01 to 1 part by mass with respect to 100 parts by mass of the total amount of (A) to (C). When it is 0.001 part by mass or more, storage stability is secured, and when it is 3 parts by mass or less, good adhesiveness is obtained, and it is not uncured.
  • an infrared absorber can be used for improving the peelability by irradiation with light having a wavelength of 750 nm to 2000 nm.
  • the infrared absorber a simple substance or a compound having strong absorption in the range of 750 to 2000 nm is usually used.
  • examples of such include inorganic pigments such as carbon black, graphite, copper chromite, and chromium oxide, and dyes such as polyphthalocyanine compounds, cyanine dyes, croconium dyes, and metal thiolate dyes. One or more of these may be used.
  • carbon black is preferable in terms of improving heat resistance.
  • carbon blacks acetylene black is preferable.
  • the amount of the infrared absorber used is preferably 0.001 to 3 parts by mass, more preferably 0.1 to 1 part by mass with respect to 100 parts by mass of the total amount of (A) to (C).
  • the amount of the infrared absorber used is preferably 0.001 to 3 parts by mass, more preferably 0.1 to 1 part by mass with respect to 100 parts by mass of the total amount of (A) to (C).
  • composition of the present invention includes various elastomers such as acrylic rubber, urethane rubber, acrylonitrile-butadiene-styrene rubber, inorganic fillers, solvents, fillers, reinforcing materials, You may use 1 type (s) or 2 or more types, such as a plasticizer, a thickener, dye, a pigment, a flame retardant, a silane coupling agent, and surfactant.
  • elastomers such as acrylic rubber, urethane rubber, acrylonitrile-butadiene-styrene rubber, inorganic fillers, solvents, fillers, reinforcing materials.
  • 1 type (s) or 2 or more types such as a plasticizer, a thickener, dye, a pigment, a flame retardant, a silane coupling agent, and surfactant.
  • the total mass ratio of (A) to (D) in the entire composition is 90% by mass or more from the viewpoint of remarkably exhibiting the effects of the present invention.
  • 95% by mass or more Preferably 98% by mass or more, still more preferably 99% by mass or more, for example 90 to 99.9% by mass. It can be.
  • the composition of the present invention can be used as an adhesive or a coating agent.
  • the composition of the present invention can be used as an easily disassembleable (meth) acrylic resin composition.
  • visible light or ultraviolet light may be irradiated at a wavelength of 365 nm in an energy amount range of 1 to 8000 mJ / cm 2. preferable.
  • the energy amount is 1 mJ / cm 2 or more, sufficient adhesiveness is obtained, and when it is 8000 mJ / cm 2 or less, productivity is excellent, decomposition products from the photopolymerization initiator are hardly generated, and outgassing is also generated. It is suppressed.
  • a range of 100 to 4000 mJ / cm 2 is more preferable in terms of productivity, adhesiveness, and low outgassing property.
  • transmits light is preferable for at least one base material.
  • a transparent substrate is more preferable.
  • the transparent substrate include inorganic substrates such as quartz, glass, quartz, and calcium fluoride, and organic substrates such as plastic.
  • one or more members selected from the group consisting of glass and quartz are preferable because they are versatile and provide a great effect.
  • the easily disassembleable (meth) acrylic resin composition of the present invention is photocurable, and the cured product can have excellent heat resistance.
  • the hardened body of the easily dismantleable (meth) acrylic resin composition of the present invention has a small amount of outgas even when exposed in a high temperature environment, and is used to bond and seal various optical components, optical devices, and electronic components. Suitable for stopping and coating.
  • the cured product of the easily disassembleable (meth) acrylic resin composition of the present invention can be used at a high temperature of preferably 200 ° C. or higher, more preferably 250 ° C. or higher, and most preferably 300 ° C. or higher.
  • cured material of the easily disassembleable (meth) acrylic-type resin composition of this invention becomes like this.
  • it is 500 degrees C or less, More preferably, it is 400 degrees C or less, Most preferably, it can be used at 350 degrees C or less.
  • it can peel by applying external force to the composite_body
  • it can peel by inserting a sheet
  • the material of the sheet or wire to be inserted is not particularly limited, but polyethylene terephthalate (PET), polybutylene terephthalate (PBT), polyethylene naphthalate, polyethylene, polypropylene, cellophane, diacetylcellulose, triacetylcellulose, acetylcellulose butyrate, poly Examples include vinyl chloride, polyvinylidene chloride, polyvinyl alcohol, ethylene-vinyl acetate copolymer, polystyrene, polycarbonate, polymethylpentene, polysulfone, polyetheretherketone, polyethersulfone, polyetherimide, polyimide, nylon, and acrylic resin. It is done.
  • covered the base material with the composition which concerns on this invention can be peeled by irradiating light with a wavelength of 750 to 2000 nm.
  • light having a wavelength of 750 nm to 2000 nm include semiconductor laser light of 750 to 880 nm, Nd—YAG laser light of 1060 nm, and the like.
  • it can peel by immersing the composite_body
  • a solution is 40 degreeC or more.
  • water can be suitably used as the solution.
  • the following compounds were selected as: (A-1) 1,2-polybutadiene oligomer (“TE-2000” manufactured by Nippon Soda Co., Ltd., see the following formula (5) for the structure) (number average molecular weight 5300 in terms of polystyrene by GPC) (A-2) Isoprene oligomer (“UC-102” manufactured by Kuraray Co., Ltd.) (number average molecular weight of 17,000 in terms of polystyrene by GPC, esterified oligomer of maleic anhydride adduct of isoprene polymer and 2-hydroxyethyl methacrylate, formula (2) Y is ethylene group, R is methyl group) (Comparative A-3)
  • the following compounds were selected as the phenoxy (poly) alkylene oxide (meth) acrylate having an alkylene oxide chain as the component (B1).
  • B-1 Nonylphenol ethylene oxide modified acrylate (“M-111” manufactured by Toagosei Co., Ltd., in formula (3), R 1 is a hydrogen atom, R 2 is an ethylene group, R 3 is a nonyl group, and n is 1)
  • M-111 manufactured by Toagosei Co., Ltd., in formula (3), R 1 is a hydrogen atom, R 2 is an ethylene group, R 3 is a nonyl group, and n is 1)
  • the following compounds were selected as the alkyl (meth) acrylate having an alkyl group having 8 to 20 carbon atoms as the component (B2).
  • B-2) Lauryl acrylate (“LA” manufactured by Osaka Organic Chemical Co., Ltd.)
  • Component (C) 1,3-adamantyl dimethanol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, isocyanuric acid ethylene oxide modified di (meth) acrylate, isocyanuric acid ethylene oxide modified tri (meth) acrylate,
  • C-1 Mixture of pentaerythritol triacrylate / pentaerythritol tetraacrylate (55-63 mass% / 37-45 mass% mixture) (“Aronix M-305” manufactured by Toagosei Co., Ltd.)
  • C-2) 1,3-adamantyl dimethanol diacrylate (“Adamantate A-201” manufactured by Idemitsu Kosan Co., Ltd.)
  • C-3) Isocyanuric acid ethylene oxide-modified di (meth) acrylate (“M-215” manufactured by Toagosei Co., Ltd.)
  • component (D) 2-Dimethylamino-2- (4-methyl-benzyl) -1- (4-morpholin-4-yl-phenyl) -butan-1-one (“Irgacure 379” manufactured by Ciba Japan Co., Ltd.) (Abbreviated as “I-379”)
  • D-2) 1-hydroxycyclohexyl phenyl ketone (“Irgacure 184” manufactured by BASF, hereinafter abbreviated as “I-184”)
  • Acetylene black (“Denka Black” manufactured by Denki Kagaku Kogyo)
  • Heating mass reduction rate of photopolymerization initiator (“Heating mass reduction rate of photopolymerization initiator” in the table): 10 mg of photopolymerization initiator was subjected to simultaneous measurement of differential heat and thermal mass “TG-DTA2000SA” manufactured by Bruker AXS. The temperature was increased from 30 ° C. to 250 ° C. at a rate of temperature increase of 10 ° C./min under a nitrogen stream, and the heating mass reduction rate of the photopolymerization initiator was measured.
  • Heated mass reduction rate of cured body (“Heating mass decreased rate of cured body” in the table): The prepared resin composition was sandwiched between PET films using a 5 ⁇ m thick shim plate as a spacer. The resin composition was cured from the upper surface with black light under the condition of an integrated light quantity of 2000 mJ / cm 2 with a wavelength of 365 nm, and then a cured product of the resin composition having a thickness of 5 ⁇ m was produced. 10 mg of the obtained cured product was allowed to stand at 300 ° C. for 10 minutes in a helium stream with a differential thermal and thermal mass simultaneous measurement device “TG-DTA2000SA” manufactured by Bruker AXS Co. It was measured. The rate of temperature increase until leaving at 300 ° C. for 10 minutes was 10 ° C./min.
  • Tensile shear adhesive strength (“Adhesive strength" in the table): Two sheets of the resin composition produced using blue plate glass (25 mm x 25 mm x thickness 0.5 mm) and the bonded part being 25 mm x 25 mm A blue plate glass was laminated and cured with a black light under the condition of an integrated light amount of 2000 mJ / cm 2 (wavelength of 365 nm) (“integrated light amount” in the table) to prepare a tensile shear bond strength test piece. The produced test piece was measured for tensile shear adhesive strength at a tensile speed of 10 mm / min in an environment of a temperature of 23 ° C. and a humidity of 50% using a universal testing machine in accordance with JIS K 6850.
  • Tensile shear adhesive strength after 250 ° C. heat resistance test (“Adhesive strength after 250 ° C. heat resistance test” in the table): Using blue plate glass (25 mm ⁇ 25 mm ⁇ thickness 0.5 mm), the bonding site is 25 mm ⁇ 25 mm, two blue plate glasses were bonded together with the prepared resin composition, and cured with a black light under the condition of an integrated light amount of 2000 mJ / cm 2 (“integrated light amount” in the table) at a wavelength of 365 nm, A test piece was prepared by exposure in an oven heated to 250 ° C. for 10 minutes.
  • the produced test piece was measured for tensile shear adhesive strength at a tensile speed of 10 mm / min in an environment of a temperature of 23 ° C. and a humidity of 50% using a universal testing machine in accordance with JIS K 6850.
  • Tensile shear adhesive strength after 300 ° C. heat resistance test (“Adhesive strength after 300 ° C. heat resistance test” in the table): Using blue plate glass (25 mm ⁇ 25 mm ⁇ thickness 0.5 mm), the bonding site is 25 mm ⁇ 25 mm, two blue plate glasses were bonded together with the prepared resin composition, and cured with a black light under the condition of an integrated light amount of 2000 mJ / cm 2 (“integrated light amount” in the table) at a wavelength of 365 nm, A test piece was prepared by exposure in an oven heated to 300 ° C. for 10 minutes.
  • the produced test piece was measured for tensile shear adhesive strength at a tensile speed of 10 mm / min in an environment of a temperature of 23 ° C. and a humidity of 50% using a universal testing machine in accordance with JIS K 6850.
  • Peeling and dismantling test (1) ((1) Sheet peeling" in the table) A test piece identical to the tensile shear bond strength evaluation was prepared, and the obtained test specimen was exposed to an oven heated to 300 ° C. for 10 minutes, and then a pet sheet was inserted between the obtained test specimens to release the specimen. Evaluated. When the blue plate glass peeled, it was evaluated as “peelable”, and when the blue plate glass did not peel, it was evaluated as “not peelable”. The evaluation results are shown in Table 1.
  • Peeling and dismantling test (2) ("(2) Infrared irradiation peeling" in the table)
  • the same test piece as the evaluation of the tensile shear bond strength was prepared, and the obtained test specimen was exposed to an oven heated to 300 ° C. for 10 minutes, and then the infrared laser (applicable device: Using a fine device / laser micromachining system (MWL-WSO05T), irradiation was performed for 5 minutes at an illuminance of 25 W / cm 2 with a wavelength of 1100 nm, and the peelability was evaluated. When the blue plate glass peeled, it was evaluated as “peelable”, and when the blue plate glass did not peel, it was evaluated as “not peelable”. The evaluation results are shown in Table 1.
  • the resin composition of the present invention has an effect that heat resistance and adhesiveness are large.
  • the adhesiveness between the substrates bonded using the resin composition of the present invention provides an effect that the adhesiveness does not decrease even when used in an environment of 250 ° C. or higher. Even if the cured product of the resin composition of the present invention is exposed at 300 ° C., an effect that there is little outgas is obtained. On the other hand, the resin composition of the present invention also has practical peelability.
  • D When a compound having a large heating mass reduction rate is used as the photopolymerization initiator, the adhesive strength after the heat resistance test is small (Experimental Example 8, Experimental Example 14, Experimental Example 16). From the comparison between Experimental Example 2 and Experimental Example 5, when acetylene black is used, the heat resistance is improved.
  • the composition of the present invention is excellent in workability and productivity because, in the production of various electronic components, optical components and optical devices, strong adhesiveness can be easily expressed simply by irradiating with ultraviolet rays or visible rays.
  • the cured product of the composition of the present invention does not deteriorate the adhesiveness even at a high temperature of 250 ° C., and the amount of outgas is extremely small even at such a high temperature. Therefore, various electronic components, optical components and optical devices bonded using the composition of the present invention can be applied even when vapor deposition at a high temperature exceeding 200 ° C. or baking coating at a high temperature is applied. Is possible.
  • optical components such as image sensors are applied to surface mounting on a circuit board, and in that case, they are passed through high-temperature solder reflow.
  • the temperature conditions for solder reflow have become stricter.
  • the use location of the photocurable resin composition in order to improve the quality of optical components and optical devices, or in order to increase productivity and production yield, the use location of the photocurable resin composition must sufficiently withstand high-temperature heat treatment. Required.
  • Optical components and optical devices produced using the composition of the present invention are very useful in industry because they can sufficiently withstand the high-temperature heat treatment.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Polymerisation Methods In General (AREA)
  • Paints Or Removers (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

L'invention concerne une composition ayant une excellente résistance à la chaleur et de faibles propriétés de dégazage. La composition contient les composants (A)-(D) décrits ci-dessous et présente un rapport en masse (A)/(C) de 3/1 à 8/1. (A) un (méth)acrylate polyfonctionnel, tel qu'un (méth)acrylate à base de diène ; (B) (B1) un phénoxy (méth)acrylate (poly)oxyalkyléné, ayant une chaîne oxyde d'alkylène et/ou (B2) un (méth)acrylate d'alkyle ayant un groupe alkyle ayant 8 à 20 atomes de carbone ; (C) un (méth)acrylate polyfonctionnel, tel que le tri((méth)acrylate de pentaérythritol ; (D) un amorceur de photopolymérisation radicalaire.
PCT/JP2015/075264 2014-09-08 2015-09-04 Composition et procédé de démontage Ceased WO2016039277A1 (fr)

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JP2016138182A (ja) * 2015-01-27 2016-08-04 デンカ株式会社 仮固定用接着剤組成物、それを用いた部材の仮固定方法及び硬化体残渣の除去方法
JP2018177843A (ja) * 2017-04-04 2018-11-15 デンカ株式会社 粘着テープ及び電子部品の製造方法
JP2019178287A (ja) * 2018-03-30 2019-10-17 太陽インキ製造株式会社 インクジェット印刷用の硬化性組成物、その硬化物及びその硬化物を有する電子部品
EP3882323A4 (fr) * 2018-11-14 2022-01-05 Denka Company Limited Composition
JPWO2022085546A1 (fr) * 2020-10-19 2022-04-28
EP4148096A4 (fr) * 2020-05-21 2023-11-01 Denka Company Limited Composition

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JP2016138182A (ja) * 2015-01-27 2016-08-04 デンカ株式会社 仮固定用接着剤組成物、それを用いた部材の仮固定方法及び硬化体残渣の除去方法
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CN105753799A (zh) * 2016-03-28 2016-07-13 西安近代化学研究所 一种含能端炔基固化剂及其制备方法
JP2018177843A (ja) * 2017-04-04 2018-11-15 デンカ株式会社 粘着テープ及び電子部品の製造方法
JP2019178287A (ja) * 2018-03-30 2019-10-17 太陽インキ製造株式会社 インクジェット印刷用の硬化性組成物、その硬化物及びその硬化物を有する電子部品
JP7112170B2 (ja) 2018-03-30 2022-08-03 太陽インキ製造株式会社 インクジェット印刷用の硬化性組成物、その硬化物及びその硬化物を有する電子部品
EP3882323A4 (fr) * 2018-11-14 2022-01-05 Denka Company Limited Composition
US12221534B2 (en) 2018-11-14 2025-02-11 Denka Company Limited Composition
EP4148096A4 (fr) * 2020-05-21 2023-11-01 Denka Company Limited Composition
US12480025B2 (en) 2020-05-21 2025-11-25 Denka Company Limited Composition
JPWO2022085546A1 (fr) * 2020-10-19 2022-04-28
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JP7726904B2 (ja) 2020-10-19 2025-08-20 日東電工株式会社 剥離方法
WO2022085546A1 (fr) * 2020-10-19 2022-04-28 日東電工株式会社 Procédé de séparation

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