WO2012005169A1 - Composition de résine durcissable - Google Patents

Composition de résine durcissable Download PDF

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Publication number
WO2012005169A1
WO2012005169A1 PCT/JP2011/065075 JP2011065075W WO2012005169A1 WO 2012005169 A1 WO2012005169 A1 WO 2012005169A1 JP 2011065075 W JP2011065075 W JP 2011065075W WO 2012005169 A1 WO2012005169 A1 WO 2012005169A1
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WO
WIPO (PCT)
Prior art keywords
component
meth
acrylate
resin composition
curable resin
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Application number
PCT/JP2011/065075
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English (en)
Japanese (ja)
Inventor
佑基 比舎
公彦 依田
渡辺　淳
Original Assignee
電気化学工業株式会社
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Application filed by 電気化学工業株式会社 filed Critical 電気化学工業株式会社
Priority to CN201180033945.8A priority Critical patent/CN102985446B/zh
Priority to JP2012523839A priority patent/JPWO2012005169A1/ja
Priority to KR1020137001959A priority patent/KR20130091318A/ko
Publication of WO2012005169A1 publication Critical patent/WO2012005169A1/fr

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Classifications

    • 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
    • C09J109/00—Adhesives based on homopolymers or copolymers of conjugated diene hydrocarbons
    • 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
    • C08F279/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
    • C08F279/02—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00 on to polymers of conjugated dienes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F279/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • 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
    • 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
    • C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
    • C09J151/003—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F2202/00—Materials and properties
    • G02F2202/28—Adhesive materials or arrangements

Definitions

  • the present invention relates to a curable resin composition.
  • the present invention relates to an adhesive composition comprising a curable resin composition.
  • the capacitive touch panel has a structure in which a transparent electrode is formed on a transparent substrate and a transparent plate is bonded thereon.
  • the bonding of the decorative plate and the touch panel, the bonding of the icon sheet and the touch panel, and the bonding of the transparent substrate and the transparent plate have used an adhesive.
  • the technique using such an adhesive has a problem of insufficient adhesion.
  • Patent Document 1 proposes a curable adhesive composition for touch panel adhesion containing (A) a (meth) acrylate oligomer having a polyisoprene, polybutadiene or polyurethane as a skeleton and (B) a softening component.
  • Patent Document 2 a (meth) acrylic monomer mainly composed of isobornyl (meth) acrylate is used for the purpose of excellent workability, long-term reliability, quick curing, and further adhesion and moisture resistance.
  • UV curable type comprising 100 parts by weight, 25-100 parts by weight of a prepolymer having polybutadiene in the main chain and having one or more (meth) acryl groups at both ends or side chains of the main chain, and a photopolymerization initiator
  • An adhesive composition is proposed.
  • Patent Document 3 discloses polyurethane acrylate, polyisoprene acrylate or the like as a resin composition for forming a cured resin layer interposed between an image display portion of an image display device and a translucent protective portion.
  • One or more polymers such as esterified products, terpene hydrogenated resins, butadiene polymers, one or more acrylate monomers such as isobornyl acrylate, dicyclopentenyloxyethyl methacrylate, 2-hydroxybutyl methacrylate, and 1
  • a resin composition containing a photopolymerization initiator such as -hydroxy-cyclohexyl-phenyl-ketone is disclosed.
  • Patent Document 1 discloses phenoxyethyl (meth) acrylate, phenoxypolyethylene glycol (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, cyclohexyl (meth) acrylate, nonylphenol EO adduct (meth) acrylate, methoxytri Cyclic (meth) acrylates such as (meth) acrylate monomers selected from ethylene glycol (meth) acrylate and tetrahydrofurfuryl (meth) acrylate are used.
  • Patent Documents 2 and 3 since it is a highly elastic resin based on a rigid skeleton monomer such as isobornyl (meth) acrylate and dicyclopentenyl (meth) acrylate, it is difficult to expand and contract the adherend in a high-temperature reliability test. It could not endure and could cause peeling.
  • the present invention has been made in view of the above circumstances. For example, when a decorative plate and an icon sheet used for a display body such as a touch panel are bonded together, when a transparent substrate and a transparent plate are bonded together, printing processing is performed. When pasting parts, it is difficult to provide sufficient initial adhesion and wet heat resistance, or when the display body and optical functional material are pasted together, the adhesive surface may peel off or display Provided is a curable resin composition that solves the problem of the prior art that the body glass is broken.
  • the present invention contains the following components (A) to (D), and the total amount of the components (A) and (B) accounts for 80 to 99% by mass of the curable resin composition.
  • the amount of component (D) used is a curable resin composition that is 0 to 10 parts by mass in a total of 100 parts by mass of component (A), component (B) and component (D).
  • (meth) acrylate (meth) acrylate,
  • the curable resin composition of the present invention is a compound of component (B), the general formula (1).
  • General formula (1) Z—O—R 1 Wherein, Z is shown a (meth) acryloyl group, R 1 represents a number 9-20 alkyl group having a carbon. ]
  • the component (A) in a total of 100 parts by mass of the component (A) and the component (B), the component (A) is 30 to 98 parts by mass, and the component (B) is 2 to 70 parts by mass.
  • the component (B) is isostearyl (meth) acrylate, lauryl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-ethylhexyl. From (meth) acrylate, n-butyl (meth) acrylate, t-butyl (meth) acrylate, ethylene glycol di (meth) acrylate, 1,3-butylene glycol di (meth) acrylate, 2-hydroxypropyl (meth) acrylate One or more members of the group.
  • the component (B) is lauryl (meth) acrylate and / or isostearyl (meth) acrylate.
  • a silane coupling agent is further contained as the component (E).
  • the diene-based or hydrogenated diene-based skeleton of the component (A) is polybutadiene, polyisoprene, a hydrogenated polybutadiene, and a hydrogen of polyisoprene.
  • the molecular weight of the oligomer (A) having a diene-based or hydrogenated diene-based skeleton is 500 to 70000.
  • the component (A) is 50 to 90 parts by mass
  • the component (B) is a total of 100 parts by mass of the component (A) and the component (B).
  • the amount of the component (C) used is 0.01 to 10 parts by mass with respect to 100 parts by mass in total of the components (A), (B) and (D).
  • the amount of the component (E) used is 0.01 to 10 parts by mass with respect to 100 parts by mass in total of the components (A), (B) and (D).
  • the present invention is an adhesive composition comprising the curable resin composition described above.
  • the present invention provides a cured product of an adhesive composition comprising the curable resin composition described above.
  • the present invention is a composite in which the adherend is coated or bonded to each other by the cured body described above.
  • the adherend described above is a composite that is at least one selected from the group consisting of triacetylcellulose, a fluorine-based polymer, polyester, polycarbonate, polyolefin, glass, and metal. .
  • the present invention is a touch panel laminate in which an adherend is bonded using the adhesive composition described above.
  • the present invention is a display including the touch panel laminate described above.
  • the curable resin composition of the present invention exhibits high initial adhesion and wet heat resistance.
  • the component (A) in the present invention is an oligomer having a diene-based or hydrogenated diene-based skeleton.
  • the main chain skeleton of the oligomer in the present invention is a diene-based or hydrogenated diene-based skeleton.
  • the diene-based or hydrogenated diene-based skeleton is preferably at least one skeleton selected from the group consisting of polybutadiene, polyisoprene, a hydrogenated polybutadiene, and a hydrogenated polyisoprene.
  • at least one selected from the group consisting of polybutadiene and polyisoprene is preferable, and polybutadiene is more preferable in terms of high adhesion durability.
  • the oligomer preferably has one or more (meth) acryloyl groups at the terminal or side chain of the main chain skeleton. Among these, those having (meth) acryloyl groups at both ends of the main chain skeleton are preferable.
  • the molecular weight of the oligomer is preferably 500 to 70000, more preferably 1000 to 60000, and most preferably 1000 to 55000. If molecular weight is 500 or more, since the hardness of the hardening body obtained by irradiating light to the curable resin composition of this invention is high, it will become easy to form an adhesive bond layer. If the molecular weight is 70,000 or less, the viscosity of the resulting curable resin composition is small, so that the workability in mixing during the production process and the workability in practical applications are improved.
  • the molecular weight of the oligomer refers to the number average molecular weight calculated as the average molecular weight per molecule.
  • the number average molecular weight of polystyrene conversion measured by GPC gel permeation chromatography
  • oligomer of the component (A) “UC-203” manufactured by Kuraray (esterified oligomer of maleic anhydride adduct of isoprene polymer and 2-hydroxyethyl methacrylate), “LIR-50” (isoprene manufactured by Kuraray) Oligomer), Kuraray “LBR-50” “LBR-307” (butadiene oligomer), Nippon Soda "TEAI-1000” (terminal acrylic modified hydrogenated 1,2-polybutadiene oligomer), Nippon Soda "TE -2000 "(terminal methacryl-modified 1,2-polybutadiene oligomer) and the like.
  • esterified oligomers of maleic anhydride adduct of isoprene polymer and 2-hydroxyethyl (meth) acrylate isoprene oligomers
  • terminal (meth) acryl-modified 1,2-polybutadiene oligomers Preferably, one or more members of the group consisting of an esterified oligomer of maleic anhydride adduct of isoprene polymer and 2-hydroxyethyl (meth) acrylate and / or a terminal (meth) acryl-modified 1,2-polybutadiene oligomer are used.
  • esterified oligomer of maleic anhydride adduct of isoprene polymer and 2-hydroxyethyl (meth) acrylate More preferred is an esterified oligomer of maleic anhydride adduct of isoprene polymer and 2-hydroxyethyl (meth) acrylate.
  • the oligomer of a component may be used independently and may mix and use 2 or more types.
  • the component (B) in the present invention is an acyclic (meth) acrylate having a homopolymer glass transition temperature of ⁇ 100 ° C. to 60 ° C.
  • Acyclic refers to (meth) acrylate having no alicyclic group or aromatic ring group, and is typically linear or branched (meth) acrylate. Examples of acyclic (meth) acrylates having a homopolymer glass transition temperature of ⁇ 100 ° C. to 60 ° C.
  • isostearyl (meth) acrylate (homopolymer glass transition temperature of acrylate: ⁇ 58 ° C.), lauryl (meth) acrylate ( Homopolymer glass transition temperature of acrylate: -30 ° C, homopolymer glass transition temperature of methacrylate: -65 ° C, 2-ethylhexyl (meth) acrylate (hompolymer glass transition temperature of acrylate: -85 ° C, homopolymer glass of methacrylate Transition temperature: ⁇ 10 ° C.), n-butyl (meth) acrylate (methacrylate homopolymer glass transition temperature: 20 ° C.), i-butyl (meth) acrylate (methacrylate homopolymer glass transition temperature: 20 ° C.), t- Butyl (meth) acrylate Homopolymer glass transition temperature of methacrylate: 20 ° C, methoxyethyl (meth) acrylate (
  • (meth) acrylates can be used alone or in combination of two or more.
  • isostearyl (meth) acrylate, lauryl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-butyl (meth) acrylate, t-butyl (meth) acrylate , Ethylene glycol di (meth) acrylate, 1,3-butylene glycol di (meth) acrylate, and 2-hydroxypropyl (meth) acrylate are preferably selected from the group consisting of isostearyl (meth) acrylate, lauryl ( One or more members selected from the group consisting of (meth) acrylate and 2-hydroxyethyl (meth) acrylate are more preferable, and lauryl (meth) acrylate and / or isostearyl (meth) acrylate are most preferable.
  • the glass transition refers to, for example, a change in which a substance such as glass that is liquid at a high temperature suddenly increases its viscosity in a certain temperature range due to a temperature drop, almost loses fluidity and becomes an amorphous solid.
  • Examples of the method for measuring the glass transition temperature include thermogravimetry, differential scanning calorimetry, differential heat measurement, and dynamic viscoelasticity measurement. In this invention, it measured by the dynamic viscoelasticity measurement.
  • the glass transition temperature of the (meth) acrylate homopolymer is described in J. Org. Brandrup, E.M. H. Immersut, Polymer Handbook, 2nd Ed. , J .; Wiley, New York 1975, photocuring technology data book (Technonet Books), etc.
  • the compound of the general formula (1) further improves the flexibility of the cured product and further improves the adhesion to polyethylene terephthalate and the like.
  • R 1 is preferably an alkyl group having 10 to 19 carbon atoms, more preferably an alkyl group having 11 to 18 carbon atoms, and most preferably a lauryl group and / or an isostearyl group.
  • These (meth) acrylates can be used alone or in combination of two or more.
  • a component is a photoinitiator (henceforth a photoinitiator).
  • the photopolymerization agent is not particularly limited as long as it initiates polymerization of (meth) acrylate such as component (A), component (B), and component (D).
  • (C) As a photoinitiator although an ultraviolet polymerization initiator, a visible light polymerization initiator, etc. are mentioned, both are used without a restriction
  • the ultraviolet polymerization initiator include benzoin, benzophenone, and acetophenone.
  • visible light polymerization initiators include acylphosphine oxide, thioxanthone, metallocene, quinone, and ⁇ -aminoalkylphenone.
  • Photoinitiators include benzophenone, 4-phenylbenzophenone, benzoylbenzoic acid, 2,2-diethoxyacetophenone, bisdiethylaminobenzophenone, benzyl, benzoin, benzoylisopropyl ether, benzyldimethyl ketal, 1-hydroxycyclohexyl phenyl ketone Thioxanthone, 2-methylthioxanthone, 2,4-dimethylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, 1- (4-isopropylphenyl) 2-hydroxy-2-methylpropane-1 -One, 1- (4- (2-hydroxyethoxy) -phenyl) -2-hydroxy-2-methyl-1-propan-1-one, 2-hydroxy-2-methyl-1-fur Nylpropan-1-one, camphorquinone, 2,4,6-
  • the curable resin composition of the present invention contains (meth) acrylates other than the (A) component and the (B) component as the (D) component, particularly for the purpose of further improving the adhesion to each adherend. can do.
  • (meth) acrylates other than component (A) and component (B) include monofunctional (meth) acrylates, polyfunctional (meth) acrylates such as bifunctional, trifunctional, tetrafunctional, pentafunctional, and hexafunctional. Can be mentioned. Among these, monofunctional (meth) acrylate is preferable.
  • the component (D) lowers the heat and moisture resistance, it is preferable that the component (D) is small, and when importance is attached to the heat and humidity resistance, it is preferable not to contain it at all. The specific addition amount will be described later.
  • monofunctional (meth) acrylates include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, tetrahydrofurfuryl (meth) ) Acrylate, caprolactone modified tetrahydrofurfuryl (meth) acrylate, cyclohexyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, isobornyl (meth) acrylate, benzyl (meth) acrylate, phenyl ( (Meth) acrylate, phenoxyethyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, phenoxytetraethylene glycol (meth) acrylate, phenoxypoly Tylene glycol (meth) acrylate, nonyl (meth) acrylate, methyl (meth) acrylate,
  • dicyclopentenyloxyethyl (meth) acrylate dicyclopentenyloxypropyl (meth) acrylate
  • examples include (meth) acrylates having a dicyclopentenyl group such as dicyclopentenyl (meth) acrylate.
  • isobornyl (meth) acrylate is more preferable in terms of improving adhesion to cycloolefin.
  • a silane coupling agent can be contained as the component (E) for the purpose of improving the adhesion to glass.
  • Silane coupling agents include ⁇ -chloropropyltrimethoxysilane, vinyltrimethoxysilane, vinyltrichlorosilane, vinyltriethoxysilane, vinyl-tris ( ⁇ -methoxyethoxy) silane, ⁇ - (meth) acryloxypropyltrimethoxy.
  • Silane ⁇ - (3,4-epoxycyclohexyl) ethyltrimethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -mercaptopropyltrimethoxysilane, ⁇ -aminopropyltriethoxysilane, N- ⁇ - (aminoethyl) ) - ⁇ -aminopropyltrimethoxysilane, N- ⁇ - (aminoethyl) - ⁇ -aminopropylmethyldimethoxysilane, ⁇ -ureidopropyltriethoxysilane, and the like.
  • ⁇ -glycidoxypropyltrimethoxysilane and / or ⁇ - (meth) acryloxypropyltrimethoxysilane are preferable from the viewpoint of adhesion to glass or the like, and ⁇ -glycidoxypropyltrimethoxysilane is preferable. Is more preferable.
  • the present invention contains the components (A) to (C) as essential components. Therefore, curing with light is possible with the components (A) to (C).
  • the curable resin composition in the present invention contains 30 to 98 parts by weight of component (A) and 2 to 70 parts by weight of component (B) in a total of 100 parts by weight of component (A) and component (B). More preferably, it contains 40 to 95 parts by weight of component (A), 5 to 60 parts by weight of component (B), 50 to 90 parts by weight of component (A), and 10 parts of component (B). Most preferably, it contains ⁇ 50 parts by weight.
  • the total mass of the component (A) and the component (B) accounts for 80 to 99% by mass of the curable resin composition in the present invention, and typically accounts for 90 to 98% by mass. .
  • Component (C) is used in an amount of 0.01 to 10 parts by mass with respect to a total of 100 parts by mass of component (A), component (B) and component (D) used as necessary.
  • the adhesive property of the curable resin composition to the adherend is particularly high, and the curability is favorable, and the content of 0.1 to 5 parts by mass is more preferable.
  • Component (D) is preferably used in an amount of 0 to 10 parts by mass, and 0 to 7 parts by mass, in a total of 100 parts by mass of component (A), component (B) and component (D) used as necessary. More preferred is 0 to 4 parts by mass. (D) It is not necessary to contain a component. When the component (D) is included, the lower limit is preferably 1 part by mass, and more preferably 2 parts by mass.
  • Component (E) is preferably used in an amount of 0.01 to 10 parts by weight, based on a total of 100 parts by weight of component (A), component (B) and component (D) used as necessary. 5 parts by mass is more preferable.
  • a commercially available antioxidant containing a polymerization inhibitor can be used.
  • elastomers various paraffins, plasticizers, fillers, colorants, rust inhibitors and the like can be used as desired.
  • the curable resin composition of the present invention can be used as an adhesive composition.
  • a composite can be produced by bonding or coating an adherend with a cured body of the adhesive composition.
  • the various materials of the adherend are preferably at least one selected from the group consisting of polyolefins such as cycloolefin polymers, triacetyl cellulose, fluorine-based polymers, polyesters, polycarbonates, glasses and metals, and groups consisting of polycarbonates, polyolefins and glasses. 1 or more types selected from are more preferable.
  • the adherend adhered with the curable resin composition of the present invention can be reworked (reused) after being completely cured.
  • the rework method is not particularly limited, but the adherends are disassembled by applying a load of 0.01 to 100 N between the one or two kinds of adherends bonded together, and the adherend after disassembly The body can be reused.
  • A-1 Methacrylate-modified 1,2-polybutadiene oligomer (“TE-2000” manufactured by Nippon Soda Co., Ltd.) (number average molecular weight 2000 in terms of polystyrene by GPC)
  • A-2) Isoprene oligomer (“LIR-50” manufactured by Kuraray Co., Ltd.) (Number average molecular weight in terms of polystyrene by GPC 54000)
  • (B-1) Lauryl methacrylate (“Light Ester L” manufactured by Kyoeisha Chemical Co., Ltd .: homopolymer glass transition temperature: ⁇ 65 ° C.)
  • B-2) 2-hydroxyethyl methacrylate (“Kyoeisha Chemical Co., Ltd.“ Light Ester HO ”: homopolymer glass transition temperature: 55 ° C.)
  • B-3) Isostearyl acrylate (“ISTA” manufactured by Osaka Organic Chemical Industry Co., Ltd .: homopolymer glass transition temperature: ⁇ 58 ° C.)
  • the following compounds were selected as the photoinitiator for component (C).
  • (D) component as the component (A) and (B) other than the component (meth) acrylate, select the following compounds.
  • (D-1) Dicyclopentenyl acrylate (homopolymer glass transition temperature: 120 ° C.)
  • (D-2) Isobornyl methacrylate (homopolymer glass transition temperature: 120 ° C.)
  • the following compounds were selected as the silane coupling agent of component (E).
  • PET Polyethylene terephthalate
  • peel adhesion strength between polyethylene terephthalate test pieces A test piece (width 50 mm ⁇ length 10 mm ⁇ thickness 0.times.) Of a biaxially stretched PET film (Lumirror T60, manufactured by Toray Industries, Inc.). 05 mm) were bonded using a curable resin composition as an adhesive composition with an adhesive layer thickness of 30 ⁇ m and an adhesive area of 40 mm long ⁇ 10 mm wide.
  • the peel adhesion strength (unit: N / cm) was measured using a tensile tester at a temperature of 23 ° C. and a humidity of 50% at a tensile speed of 10 mm / min.
  • the tensile shear bond strength (unit: MPa) was measured using a tensile tester at a temperature of 23 ° C. and a humidity of 50% at a tensile speed of 10 mm / min.
  • the bond strength was measured.
  • the light irradiation conditions followed the method described in [Photocurability].
  • the peel adhesion strength (unit: N / cm) was measured using a tensile tester at a temperature of 23 ° C. and a humidity of 50% at a tensile speed of 10 mm / min.
  • the appearance of the bonded part was visually observed to determine whether it was yellowed.
  • the peel adhesion strength (unit: N / cm) was measured using a tensile tester at a temperature of 23 ° C. and a humidity of 50% at a tensile speed of 10 mm / min.
  • Triacetyl cellulose adhesion evaluation peeleling adhesive strength between triacetyl cellulose test pieces
  • Triacetyl cellulose (TAC) film average thickness 40 ⁇ m, manufactured by Fuji Film Co., Ltd.
  • test piece width 50 mm ⁇ length 10 mm ⁇
  • a thickness of 0.04 mm was bonded to each other with the adhesive layer having a thickness of 10 ⁇ m and a bonding area of 40 mm in length and 10 mm in width by using the curable resin composition as an adhesive composition.
  • the bond strength was measured.
  • the light irradiation conditions followed the method described in [Photocurability].
  • the peel adhesion strength (unit: N / cm) was measured using a tensile tester at a temperature of 23 ° C. and a humidity of 50% at a tensile speed of 50 mm / min.
  • PVDF film average thickness 40 ⁇ m, “DX film” manufactured by Denki Kagaku Kogyo Co., Ltd.
  • test piece width 50 mm ⁇ length 10 mm ⁇ thickness 0.04 mm
  • curable resin composition as an adhesive composition with an adhesive layer thickness of 10 ⁇ m and an adhesive area of 40 mm long ⁇ 10 mm wide.
  • the bond strength was measured.
  • the light irradiation conditions followed the method described in [Photocurability].
  • the peel adhesive strength (unit: N / cm) was measured using a tensile tester at a temperature of 23 ° C. and a humidity of 50% at a tensile speed of 50 mm / min.
  • an adhesive composition “G-55” manufactured by Denki Kagaku Kogyo Co., Ltd. was used on the Tempax test piece side, and a galvanized steel sheet (width 100 mm ⁇ length 25 mm ⁇ A thickness of 2.0 mm, manufactured by Engineering Test Service Co., Ltd.) was adhered.
  • the galvanized steel sheet was chucked, and the initial tensile shear bond strength was measured.
  • the tensile shear bond strength (unit: MPa) was measured using a tensile tester at a temperature of 23 ° C. and a humidity of 50% at a tensile speed of 10 mm / min.
  • the curable resin composition of the present invention exhibits high adhesiveness.
  • the curable resin composition of the present invention exhibits high adhesiveness. In particular, it exhibits high adhesion to polycarbonate, polyolefin, and glass. Since the curable resin composition of the present invention exhibits high adhesiveness, when a display body such as a thin glass LCD is bonded to an optical functional material such as an acrylic plate or a polycarbonate plate, the adhesive surface may be peeled off, or the LCD Will not break or the LCD will not display unevenly.
  • the curable resin composition of the present invention has a high resistance to moist heat and can follow the deformation of the adherend in a heated atmosphere, so that the adherend is not peeled off.
  • Experimental Example 14 does not contain a silane coupling agent, but has higher adhesion than the comparative example.
  • Experimental Example 15 does not contain a component (C)
  • a curable resin composition does not harden
  • cure and adhesiveness is small.
  • Experimental Example 16 and Experimental Example 17 contain a large amount of an alicyclic (meth) acrylate having a rigid skeleton such as isobornyl methacrylate and dicyclopentenyl acrylate, and do not contain the component (B).
  • the resin composition does not have flexibility and has low adhesiveness.
  • the curable resin composition of the present invention can be used for an adhesive composition for a touch panel laminate.
  • the touch panel laminate is generally composed of a cover material / touch panel sensor / liquid crystal panel layer.
  • the curable resin composition according to the present invention can be used as an adhesive for bonding a touch panel sensor and a cover material.
  • a cover material such as a decorative plate or an icon sheet for designating a touch position is bonded to the surface of the touch panel. It can be used as an adhesive. It can also be used as an adhesive that bonds the touch panel sensor and the liquid crystal panel together.
  • a transparent electrode is formed on a transparent substrate, and a transparent plate is bonded thereon.
  • the curable resin composition of the present invention is also suitable as an adhesive when a transparent electrode is formed on a transparent substrate and a transparent plate is bonded thereon.
  • the touch panel laminate of the present invention can be used as a display.

Abstract

'invention concerne une composition de résine durcissable qui présente une adhésivité initiale et une durabilité d'adhérence élevées. La composition de résine durcissable comprend (A) un oligomère avec diène ou u squelette de diène hydrogéné, (B) un (méth)acrylate acyclique avec une température de transition vitreuse pour l'homopolymère de -100°C à 60°C, (C) un initiateur de photopolymérisation, et (D) un (méth)acrylate différent des composants (A) et (B). La quantité totale utilisée des composants (A) et (B) est de 80-99 en masse% de la composition de résine durcissable et la quantité du composant (D) utilisé est de 0 à 10 parts en masse pour 100 parts en masse du total des composants (A), (B) et (D).
PCT/JP2011/065075 2010-07-08 2011-06-30 Composition de résine durcissable WO2012005169A1 (fr)

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014142054A1 (fr) * 2013-03-13 2014-09-18 富士フイルム株式会社 Film adhésif et corps empilé pour écran tactile
WO2014142052A1 (fr) * 2013-03-13 2014-09-18 富士フイルム株式会社 Feuille adhésive, corps empilé pour écran tactile, et écran tactile de type capacitif
JP2014525960A (ja) * 2011-07-25 2014-10-02 ヘンケル・チャイナ・カンパニー・リミテッド 光硬化性接着剤組成物およびその使用
WO2015025803A1 (fr) * 2013-08-21 2015-02-26 富士フイルム株式会社 Feuille adhésive pour panneaux tactiles, laminé pour panneaux tactiles et panneau tactile capacitif
JP2015071683A (ja) * 2013-10-02 2015-04-16 三洋化成工業株式会社 活性エネルギー線硬化性樹脂及びそれを含有する活性エネルギー線硬化性樹脂組成物
JP2015105279A (ja) * 2013-11-28 2015-06-08 株式会社クラレ 硬化性樹脂組成物
WO2015129308A1 (fr) * 2014-02-28 2015-09-03 富士フイルム株式会社 Corps stratifié pour panneau tactile et feuille adhésive
EP2927295A4 (fr) * 2012-11-30 2016-08-03 Lintec Corp Composition d'agent adhésif, feuille adhésive et dispositif électronique
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KR101969339B1 (ko) * 2015-06-30 2019-04-16 주식회사 엘지화학 경화성 조성물
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CN114787213A (zh) * 2019-12-13 2022-07-22 日东新兴有限公司 固化性组合物

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58117207A (ja) * 1981-12-31 1983-07-12 Matsushita Electric Works Ltd 紫外線硬化性樹脂組成物
JP2003266613A (ja) * 2002-03-15 2003-09-24 Toyo Ink Mfg Co Ltd ガスバリア性積層体用基材、およびそれを用いたガスバリア性積層体
JP2006306951A (ja) * 2005-04-27 2006-11-09 Mitsubishi Rayon Co Ltd アクリル系樹脂板の製造方法、並びにタッチパネル用重合性組成物、該重合性組成物を用いた透明基板、透明電極板およびタッチパネル
JP2008069239A (ja) * 2006-09-13 2008-03-27 Denki Kagaku Kogyo Kk 工芸ガラス用アクリル系接着剤
JP2010000434A (ja) * 2008-06-19 2010-01-07 Jsr Corp タッチパネルの製造方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2865534B2 (ja) * 1993-09-22 1999-03-08 積水化学工業株式会社 接着性テープおよび粘着性テープ
JP2003342335A (ja) * 2002-05-28 2003-12-03 Mitsui Takeda Chemicals Inc 水系エマルション組成物および接着性組成物
JP4645797B2 (ja) * 2004-04-23 2011-03-09 株式会社スリーボンド 難接着材質用光硬化性樹脂組成物
JP4916681B2 (ja) * 2005-07-04 2012-04-18 電気化学工業株式会社 仮固定方法用光硬化性接着剤及びそれを用いる部材の仮固定方法
JP5052792B2 (ja) * 2006-01-13 2012-10-17 電気化学工業株式会社 樹脂組成物及びそれを用いる被加工部材の仮固定方法と表面保護方法
JP5570752B2 (ja) * 2008-05-12 2014-08-13 電気化学工業株式会社 接着体
TWI485214B (zh) * 2008-09-05 2015-05-21 Kyoritsu Chemical Co Ltd And a photohardenable resin composition for bonding an optical functional material

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58117207A (ja) * 1981-12-31 1983-07-12 Matsushita Electric Works Ltd 紫外線硬化性樹脂組成物
JP2003266613A (ja) * 2002-03-15 2003-09-24 Toyo Ink Mfg Co Ltd ガスバリア性積層体用基材、およびそれを用いたガスバリア性積層体
JP2006306951A (ja) * 2005-04-27 2006-11-09 Mitsubishi Rayon Co Ltd アクリル系樹脂板の製造方法、並びにタッチパネル用重合性組成物、該重合性組成物を用いた透明基板、透明電極板およびタッチパネル
JP2008069239A (ja) * 2006-09-13 2008-03-27 Denki Kagaku Kogyo Kk 工芸ガラス用アクリル系接着剤
JP2010000434A (ja) * 2008-06-19 2010-01-07 Jsr Corp タッチパネルの製造方法

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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EP2927295A4 (fr) * 2012-11-30 2016-08-03 Lintec Corp Composition d'agent adhésif, feuille adhésive et dispositif électronique
US10081741B2 (en) 2012-11-30 2018-09-25 Lintec Corporation Adhesive agent composition, adhesive sheet, and electronic device
WO2014142052A1 (fr) * 2013-03-13 2014-09-18 富士フイルム株式会社 Feuille adhésive, corps empilé pour écran tactile, et écran tactile de type capacitif
JP2014198811A (ja) * 2013-03-13 2014-10-23 富士フイルム株式会社 粘着シート、タッチパネル用積層体、静電容量式タッチパネル
WO2014142054A1 (fr) * 2013-03-13 2014-09-18 富士フイルム株式会社 Film adhésif et corps empilé pour écran tactile
TWI601642B (zh) * 2013-03-13 2017-10-11 富士軟片股份有限公司 黏著膜、觸控面板用積層體
JPWO2014142054A1 (ja) * 2013-03-13 2017-02-16 富士フイルム株式会社 粘着フィルム、タッチパネル用積層体
WO2015025803A1 (fr) * 2013-08-21 2015-02-26 富士フイルム株式会社 Feuille adhésive pour panneaux tactiles, laminé pour panneaux tactiles et panneau tactile capacitif
CN105492555A (zh) * 2013-08-21 2016-04-13 富士胶片株式会社 触控面板用粘着片、触控面板用层积体、静电电容式触控面板
JP2015172921A (ja) * 2013-08-21 2015-10-01 富士フイルム株式会社 タッチパネル用粘着シート、タッチパネル用積層体、静電容量式タッチパネル
CN105492555B (zh) * 2013-08-21 2017-08-01 富士胶片株式会社 触控面板用粘着片、触控面板用层积体、静电电容式触控面板
KR101847750B1 (ko) 2013-08-21 2018-04-10 후지필름 가부시키가이샤 터치 패널용 점착 시트, 터치 패널용 적층체, 정전 용량식 터치 패널
JP2015071683A (ja) * 2013-10-02 2015-04-16 三洋化成工業株式会社 活性エネルギー線硬化性樹脂及びそれを含有する活性エネルギー線硬化性樹脂組成物
JP2015105279A (ja) * 2013-11-28 2015-06-08 株式会社クラレ 硬化性樹脂組成物
JP2015179498A (ja) * 2014-02-28 2015-10-08 富士フイルム株式会社 タッチパネル用積層体、および、粘着シート
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CN102985446B (zh) 2016-03-02

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