WO2024062930A1 - Agent adhésif, produit durci et élément - Google Patents

Agent adhésif, produit durci et élément Download PDF

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Publication number
WO2024062930A1
WO2024062930A1 PCT/JP2023/032628 JP2023032628W WO2024062930A1 WO 2024062930 A1 WO2024062930 A1 WO 2024062930A1 JP 2023032628 W JP2023032628 W JP 2023032628W WO 2024062930 A1 WO2024062930 A1 WO 2024062930A1
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Prior art keywords
group
meth
acrylate
component
adhesive
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PCT/JP2023/032628
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English (en)
Japanese (ja)
Inventor
良太 照沼
直也 加藤
隆司 福本
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株式会社クラレ
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Publication of WO2024062930A1 publication Critical patent/WO2024062930A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • 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
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • 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 relates to an adhesive, a cured product of the adhesive, and a member containing the cured product.
  • a touch panel In a display device in which a touch panel is bonded, there are gaps (sometimes referred to as air gaps) between the transparent conductive film and the LCD (Liquid Crystal Display) or organic EL, and between the transparent conductive film and the cover glass. Since the amount of reflected light increases, the amount of visible light decreases, that is, visibility decreases. Therefore, the transparent conductive film and the LCD or organic EL, and the transparent conductive film and the cover glass are often bonded together by OCR (Optical Clear Resin).
  • OCR Optical Clear Resin
  • the adhesion fills the air gap and reduces reflected light, so the amount of visible light increases, that is, visibility improves. In addition, the adhesion provides effects such as improved level followability, improved mechanical strength, and prevention of foreign matter contamination.
  • the material having high adhesiveness and heat resistance includes a block copolymer having a polymer block (A) and a (meth)acrylic polymer block (B), and a vinyl polymer (C),
  • the vinyl polymer (C) has a glass transition temperature within a predetermined range, a number average molecular weight within a predetermined range, and the content of the vinyl polymer (C) is less than 100% by mass of the block copolymer.
  • a pressure-sensitive adhesive composition for a decorative film is disclosed in which the viscosity is within a predetermined range with respect to the viscosity (see Patent Document 1).
  • Patent Document 1 requires that the block copolymer, which is a raw material component, be synthesized in advance, and the synthesis itself requires time and effort. Furthermore, after drying the composition obtained by mixing each component, it is necessary to leave it at 40° C. for 5 days to age it to obtain an adhesive film, which also requires time. Therefore, there is a need to develop other adhesives with excellent adhesive properties and heat resistance.
  • an object of the present invention is to provide an adhesive with excellent adhesiveness and heat resistance, to provide a cured product of the adhesive, and to provide a member containing the cured product.
  • the present invention includes the embodiments [1] to [13] below.
  • R 1 to R 3 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, or It represents an aralkyl group having 7 to 13 carbon atoms, and R 4 represents a (meth)acryloyl group, a vinylphenyl group, or an alkenyl group having 2 to 6 carbon atoms.
  • n represents an integer from 1 to 6.
  • R 1 and R 2 are hydrogen atoms
  • R 3 is a hydrogen atom or a methyl group
  • n is an integer of 1 to 4
  • R 4 is (meth)acryloyl
  • the component (B1) has a (meth)acryloyl group.
  • the component (B1) contains at least one selected from the group consisting of alkyl or cycloalkyl (meth)acrylate (B1-1) and hydroxyalkyl (meth)acrylate (B1-2). 3].
  • the component (B2) contains poly(meth)acrylate.
  • the poly(meth)acrylate includes at least one selected from the group consisting of urethane poly(meth)acrylate and epoxy poly(meth)acrylate.
  • an adhesive with excellent adhesiveness and heat resistance, to provide a cured product of the adhesive, and to provide a member containing the cured product.
  • the (meth)acryloyl group includes both an acryloyl group and a methacryloyl group.
  • (Meth)acrylate includes both acrylate and methacrylate.
  • the adhesive of this embodiment is A polyfunctional polymerizable compound (A) represented by the following general formula (a1) [hereinafter sometimes simply referred to as "multifunctional polymerizable compound (A)” or “component (A)”. ] 0.05 to 9.5% by mass, and polymerizable monomer (B) [hereinafter sometimes referred to as "component (B)”. ]90.5-99.95% by mass It is an adhesive, including.
  • R 1 to R 3 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, or It represents an aralkyl group having 7 to 13 carbon atoms, and R 4 represents a (meth)acryloyl group, a vinylphenyl group, or an alkenyl group having 2 to 6 carbon atoms.
  • n represents an integer from 1 to 6.
  • the adhesive of this embodiment has excellent adhesive properties and excellent heat resistance, especially since it contains the predetermined amount of the polyfunctional polymerizable compound (A). This is presumed to be due to the fact that the multifunctional polymerizable compound (A) having a predetermined molecular length has a crosslinkable structure, which increases the crosslinking density. However, even if the inference is incorrect, this does not affect the scope of the present invention.
  • liquid refers to having fluidity, and specifically refers to having a viscosity of 10,000 mPa ⁇ s or less when measured with a cone plate type viscometer, and The viscosity value is preferably 7,000 mPa ⁇ s or less, more preferably 5,000 mPa ⁇ s or less.
  • Polyfunctional polymerizable compound (A) Component (A) is a polyfunctional polymerizable compound and is represented by the general formula (a1).
  • polyfunctional polymerizable means that the compound represented by the general formula (a1) has a polymerizable functional group R4 and a polymerizable functional group having the following structure. This is because it has Note that even if the polymerizability may be lowered depending on the type of R 1 to R 3 or the value of n, the compound is referred to as a polyfunctional polymerizable compound in the present invention.
  • R 1 to R 3 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, or a carbon Represents an aralkyl group of numbers 7 to 13.
  • the alkyl group having 1 to 6 carbon atoms each independently represented by R 1 to R 3 is preferably an alkyl group having 1 to 3 carbon atoms, more preferably an alkyl group having 1 or 2 carbon atoms, from the viewpoint of adhesiveness and heat resistance. It is an alkyl group.
  • alkyl group examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, t-butyl group, n-propyl group, n-hexyl group, and the like.
  • the alkenyl group having 2 to 6 carbon atoms each independently represented by R 1 to R 3 is preferably an alkenyl group having 2 to 4 carbon atoms, more preferably an alkenyl group having 2 or 3 carbon atoms, from the viewpoint of adhesiveness and heat resistance. It is an alkenyl group.
  • alkenyl group examples include vinyl group, allyl group, 1-propenyl group, 1-butenyl group, 1-pentenyl group, 3-pentenyl group, 5-pentenyl group, 1-hexenyl group, 3-hexenyl group, 6 -hexenyl group, etc.
  • the aryl group having 6 to 12 carbon atoms each independently represented by R 1 to R 3 is preferably an aryl group having 6 to 10 carbon atoms from the viewpoint of adhesiveness and heat resistance.
  • the aryl group include a phenyl group, a naphthyl group, and a biphenylyl group.
  • the aralkyl group having 7 to 13 carbon atoms each independently represented by R 1 to R 3 is preferably an aralkyl group having 7 to 9 carbon atoms from the viewpoint of adhesiveness and heat resistance.
  • Examples of the aralkyl group include a benzyl group and a phenethyl group.
  • R 1 and R 2 are each preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and more preferably a hydrogen atom.
  • R 3 is preferably a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, more preferably a hydrogen atom or a methyl group, and still more preferably a methyl group.
  • R 4 represents a (meth)acryloyl group, a vinylphenyl group, or an alkenyl group having 2 to 6 carbon atoms.
  • the alkenyl group having 2 to 6 carbon atoms represented by R 4 is preferably an alkenyl group having 2 to 4 carbon atoms, more preferably an alkenyl group having 2 or 3 carbon atoms, from the viewpoint of adhesiveness and heat resistance.
  • Examples of the alkenyl group include the same ones as in the case of R 1 to R 3 .
  • R 4 is preferably a (meth)acryloyl group or a vinylphenyl group, more preferably a (meth)acryloyl group, and still more preferably a methacryloyl group.
  • n represents an integer of 1 to 6. From the viewpoint of adhesiveness and heat resistance, n is preferably an integer of 1 to 4, more preferably an integer of 1 to 3, still more preferably 1 or 2, particularly preferably 1.
  • R 1 and R 2 in general formula (I) are hydrogen atoms
  • R 3 is a hydrogen atom or a methyl group
  • n is an integer from 1 to 4
  • R 4 is a (meth)acryloyl group.
  • an embodiment in which it is a vinyl phenyl group is also preferred, and a more preferred embodiment is as described above.
  • the component (A) is preferably a polyfunctional polymerizable compound represented by the following general formula (a2).
  • R 5 represents a hydrogen atom or a methyl group.
  • R 5 is preferably a methyl group.
  • the polyfunctional polymerizable compound represented by the general formula (a2) can be obtained by, for example, reacting (meth)acrylic acid with an alcohol having an unsaturated double bond structure corresponding to the above structure in a known esterification reaction. This can be obtained by In addition, by referring to or applying the method for producing a polyfunctional polymerizable compound represented by the general formula (a2), the polyfunctional polymerizable compound (A) represented by the general formula (a1) can be easily produced. can do.
  • the adhesive of this embodiment contains component (A) in an amount of 0.05 to 9.5% by mass, preferably 0.10 to 9.0% by mass, more preferably 0.15 to 8.0% by mass, and even more preferably is contained in an amount of 0.15 to 5.0% by weight, particularly preferably 0.15 to 3.0% by weight, and most preferably 0.15 to 1.5% by weight.
  • component (A) in the adhesive of this embodiment is equal to or higher than the lower limit, it is possible to obtain an effect of improving heat resistance while having excellent adhesiveness. Further, by setting the content of the component (A) in the adhesive of the present embodiment to be less than or equal to the upper limit value, it is possible to avoid the possibility that the adhesiveness will deteriorate.
  • component (A) in the adhesive of this embodiment it is preferable not to increase the content of component (A) in the adhesive of this embodiment too much, for example, 8.0% by mass or less.
  • the content is preferably 5.0% by mass or less, more preferably 3.0% by mass or less, and particularly preferably 1.5% by mass or less.
  • Component (B) is a polymerizable monomer (but does not contain component (A)).
  • Component (B) is a monofunctional polymerizable monomer (B1) [hereinafter sometimes referred to as component (B1)] from the viewpoint of adhesiveness and heat resistance. ] or a polyfunctional polymerizable monomer (B2) [hereinafter sometimes referred to as component (B2). ], or may contain both a monofunctional polymerizable monomer (B1) and a polyfunctional polymerizable monomer (B2).
  • Component (B1) is a monomer having one polymerizable functional group.
  • the polymerizable functional group include a (meth)acryloyl group, a vinylphenyl group, and an alkenyl group having 2 to 6 carbon atoms.
  • the alkenyl group having 2 to 6 carbon atoms include the same ones as in the case of R 4 .
  • the polymerizable functional group is preferably a (meth)acryloyl group or a vinylphenyl group, more preferably a (meth)acryloyl group, and even more preferably an acryloyl group.
  • Component (B1) may be used alone or in combination of two or more.
  • component (B1) is preferably used in combination of two or more kinds, more preferably in combination with 2 to 6 kinds, even more preferably in combination with 2 to 4 kinds, and even more preferably in combination of 3 kinds. It is particularly preferable to use them together.
  • component (B1) having a (meth)acryloyl group Methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, t-butyl (meth)acrylate, isobutyl ( meth)acrylate, n-hexyl(meth)acrylate, cyclohexyl(meth)acrylate, 2-ethylhexyl(meth)acrylate, lauryl(meth)acrylate, cetyl(meth)acrylate, stearyl(meth)acrylate, isobornyl(meth)acrylate, etc.
  • alkyl or cycloalkyl (meth)acrylate (B1-1) [however, it does not include hydroxyalkyl (meth)acrylate (B1-2) and halogenated alkyl (meth)acrylate (B1-3) described below.
  • Hydroxyalkyl (meth)acrylate (B1-2) such as 4-hydroxybutyl (meth)acrylate
  • Halogenated alkyl (meth)acrylate (B1-3) such as 2,3-dibromopropyl (meth)acrylate
  • Aromatic (meth)acrylates (B1-4) such as benzyl (meth)acrylate and phenyl (meth)acrylate
  • Silyl group-containing (meth)acrylates (B1-5) such as 3-(meth)acryloyloxypropyltrimethoxysilane and 11-(meth)acryloyloxyundecyltrimethoxysilane; can be mentioned.
  • the component (B1) having a (meth)acryloyl group contains at least one selected from the group consisting of alkyl or cycloalkyl (meth)acrylate (B1-1) and hydroxyalkyl (meth)acrylate (B1-2). It is preferable that at least one selected from the group consisting of isobornyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and lauryl (meth)acrylate is included, and isobornyl acrylate, 4-hydroxybutyl It is more preferable that at least one selected from the group consisting of acrylate and lauryl acrylate is included.
  • the adhesive of the present embodiment contains both of these as the (B1) component.
  • the adhesive of the present embodiment contains both an alkyl or cycloalkyl (meth)acrylate (B1-1) and a hydroxyalkyl (meth)acrylate (B1-2) as the component (B1)
  • the content ratio thereof [(B1-1)/(B1-2)], in mass ratio is preferably 40/60 to 90/10, more preferably 50/50 to 90/10, even more preferably 55/45 to 85/15, particularly preferably 60/40 to 85/15, and most preferably 65/35 to 85/15.
  • the adhesive of the present embodiment contains both an alkyl (meth)acrylate and a cycloalkyl (meth)acrylate as the component (B1-1)
  • the content ratio thereof [alkyl (meth)acrylate/cycloalkyl (meth)acrylate] is preferably 10/90 to 60/40, more preferably 15/85 to 50/50, even more preferably 20/80 to 45/55, and particularly preferably 25/75 to 45/55, by mass.
  • the alkyl group or cycloalkyl group possessed by the alkyl or cycloalkyl (meth)acrylate (B1-1) is preferably an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms, more preferably An alkyl group having 4 to 18 carbon atoms or a cycloalkyl group having 4 to 14 carbon atoms, more preferably an alkyl group having 8 to 14 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms.
  • component (B1) monomers other than the above-mentioned monomers may be used as long as the monomer has one polymerizable functional group.
  • the content of the component (B1) in the adhesive of this embodiment is preferably 60 to 98% from the viewpoint of adhesiveness and heat resistance. It is 5% by mass, more preferably 65 to 98.5% by mass, may be 70 to 98.5% by mass, or may be 80 to 98.5% by mass.
  • Component (B2) is a monomer having two or more polymerizable functional groups. Therefore, component (B2) can also function as a crosslinking agent.
  • the polymerizable functional group is explained in the same manner as in the case of (B1) above, and the preferred ones are also the same.
  • Component (B2) may contain poly(meth)acrylate. Examples of the poly(meth)acrylate include urethane poly(meth)acrylate, epoxy poly(meth)acrylate, and other poly(meth)acrylates.
  • the poly(meth)acrylate preferably includes at least one selected from the group consisting of urethane poly(meth)acrylate and epoxy poly(meth)acrylate.
  • the urethane poly(meth)acrylate is a poly(meth)acrylate having a polyurethane skeleton.
  • the polyurethane skeleton may contain an aliphatic skeleton (excluding the rubber skeleton and hydrogenated rubber skeleton described below), or one or more rubber skeletons selected from the group consisting of polybutadiene and polyisoprene. It may contain one or more hydrogenated rubber skeletons selected from the group consisting of hydrogenated polybutadiene and hydrogenated polyisoprene, or it may contain a polyether skeleton, a polycarbonate skeleton, and a polyester skeleton. It may contain one or more skeletons selected from the group.
  • the urethane poly(meth)acrylate may be urethane di(meth)acrylate.
  • the weight average molecular weight (Mw) of the urethane poly(meth)acrylate is not particularly limited, but from the viewpoint of operability, it is preferably 1,000 to 30,000, more preferably 2,500 to 15,000, and even more preferably is from 3,000 to 10,000, particularly preferably from 3,500 to 7,500.
  • the weight average molecular weight is a polystyrene equivalent weight average molecular weight determined from gel permeation chromatography (GPC) measurements.
  • GPC gel permeation chromatography
  • UV-3700B manufactured by Mitsubishi Chemical Corporation, Mw; 38,000
  • UA10000B manufactured by KSM Corporation, Mw; 25,000
  • UN7700 manufactured by Neagari Industries, Ltd., Mw; 20,000
  • UN-9200A manufactured by Negami Kogyo Co., Ltd., Mw; 15,000
  • UN-9000H manufactured by Negami Kogyo Co., Ltd., Mw; 5,000
  • EBECRYL registered trademark
  • epoxy poly(meth)acrylate examples include bisphenol type epoxy (meth)acrylate, novolak type epoxy (meth)acrylate, aliphatic type epoxy (meth)acrylate, and the like.
  • the weight average molecular weight of the epoxy poly(meth)acrylate is not particularly limited, but from the viewpoint of operability, it is preferably 200 to 3,000, more preferably 300 to 1,700, even more preferably 300 to 1,300, Particularly preferably 300 to 1,000.
  • Examples of other poly(meth)acrylates include dipropylene glycol di(meth)acrylate, 1,6- Di(meth)acrylates such as hexanediol di(meth)acrylate, tripropylene glycol di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate; trimethylolpropane tri(meth)acrylate, trimethylolpropane ethoxytri( Tri(meth)acrylates such as meth)acrylate and pentaerythritol tri(meth)acrylate; Tetra(meth)acrylates such as dipentaerythritol ethoxytetra(meth)acrylate and ditrimethylolpropane tetra(meth)acrylate; Dipentaerythritol hexa( Examples include hexa(meth)acrylates such as meth
  • component (B2) component When component (B) contains a monofunctional polymerizable monomer (B2), the content of component (B2) in the adhesive of this embodiment is preferably 1 to 40% by mass from the viewpoint of adhesiveness and heat resistance. %, more preferably 3 to 35% by weight, may be 5 to 30% by weight, or may be 5 to 15% by weight.
  • the content of component (B2) relative to the total amount of component (B) is preferably 20% by mass or less, more preferably 15% by mass or less, from the viewpoint of adhesiveness and heat resistance, and there is no particular restriction on the lower limit. , may be 1% by mass or more, 3% by mass or more, or 5% by mass or more.
  • the adhesive of this embodiment contains component (B) in an amount of 90.5 to 99.95% by mass, preferably 91 to 99.90% by mass, more preferably 92 to 99.85% by mass. % by weight, more preferably 95-99.85% by weight, particularly preferably 97-99.85% by weight, most preferably 98.5-99.85% by weight.
  • the adhesive of this embodiment may have a total content of component (A) and component (B) of 100% by mass, or a total content including component (C) described below [(A) +(B)+(C)] may be 100% by mass, or the total content including component (C) and other components described below [(A)+(B)+(C)+others ] may be 100% by mass.
  • the adhesive of this embodiment preferably further contains (C) 0.1 to 3% by mass of a polymerization initiator, and (C) a polymerization initiator of 0.5 to 3% by mass, from the viewpoint of further increasing adhesiveness and adhesion speed. More preferably, it contains 2% by mass.
  • the polymerization initiator may be a photopolymerization initiator, a thermal polymerization initiator, or both a photopolymerization initiator and a thermal polymerization initiator.
  • a known photopolymerization initiator can be used, such as an acetophenone polymerization initiator, a benzophenone polymerization initiator, a Michler's ketone polymerization initiator, a benzoin polymerization initiator, and a thioxanthone polymerization initiator.
  • examples include initiators, acylphosphine oxide polymerization initiators, titanocene polymerization initiators, and the like.
  • an acetophenone polymerization initiator and a benzophenone polymerization initiator are preferred, and an acetophenone polymerization initiator is more preferred.
  • One type of photopolymerization initiator may be used alone, or two or more types may be used in combination.
  • the adhesive of this embodiment may further contain a sensitizer.
  • the sensitizer include n-butylamine, di-n-butylamine, tri-n-butylphosphine, allylthiouric acid, triethylamine, diethylaminoethyl methacrylate, and the like.
  • thermal polymerization initiator a known thermal polymerization initiator can be used, and examples thereof include azo compounds, peroxides, persulfates, pinacol, and the like. Among these, azo compounds, peroxides, and persulfates are preferred as thermal polymerization initiators.
  • One type of thermal polymerization initiator may be used alone, or two or more types may be used in combination.
  • the adhesive of this embodiment may further contain a reducing agent. By containing a reducing agent, the amount of thermal polymerization initiator used can be reduced.
  • thermal polymerization initiator and a reducing agent examples include a combination of the above-mentioned persulfate and a reducing agent such as sodium metabisulfite and sodium hydrogensulfite; a combination of the above-mentioned peroxide and a tertiary amine, etc. It will be done.
  • the adhesive of this embodiment may or may not further contain other components.
  • the content of the other components is preferably 0.1 to 5% by mass, more preferably 0.1% by mass from the viewpoint of adhesiveness and adhesion speed. ⁇ 2% by mass.
  • the adhesive of the present embodiment contains two or more other components, the content of each component is preferably within the above range.
  • the other components include, but are not limited to, sensitizers, reducing agents, plasticizers, fillers, anti-aging agents, preservatives, thickeners, and pigments.
  • one type may be used alone, or two or more types may be used in combination.
  • the above (A) component, (B) component, optionally (C) component, and optionally other components are heated preferably at 5 to 60°C, more preferably at 15 to 55°C, even more preferably at 20 to 50°C.
  • the adhesive of this embodiment can be obtained.
  • it is preferable to set the mixing temperature high from the viewpoint of operability for example, 30 to 60°C is preferable, and 40 to 60°C is more preferable. , but is not particularly limited.
  • a cured product of the adhesive can be obtained by irradiation with active energy rays.
  • active energy ray a light beam, an electromagnetic wave, a particle beam, or a combination thereof can be used, but from the viewpoint of curing speed, availability of irradiation equipment, price, etc., ultraviolet rays and electron beams are preferable, and ultraviolet rays are more preferable. preferable.
  • the cumulative amount of active energy rays is preferably 500 to 10,000 mJ/cm 2 , more preferably 1,000 to 5,000 mJ/cm 2 , and still more preferably 3,000 to 4,000 mJ/cm 2 .
  • the adhesive of this embodiment contains a thermal polymerization initiator, a cured product of the adhesive can be obtained by heating.
  • the heating temperature is preferably 50 to 250°C, more preferably 70 to 200°C. Since the heating time varies depending on the type of thermal polymerization initiator, the type of components in the adhesive, the reaction temperature, etc., it may be adjusted as appropriate.
  • the tan ⁇ in the temperature range where the adhesive is applied is preferably It is 0.18 or more, more preferably 0.4 or more, even more preferably 0.5 or more, particularly preferably 0.6 or more, and there is no particular restriction on the upper limit, and it is 1.5 or less. It may be 1.2 or less.
  • the temperature range to which the composition is applied includes, for example, a temperature range including 60°C.
  • the present invention also provides a member containing a cured product of the adhesive of this embodiment.
  • the adhesive of this embodiment is introduced between the transparent conductive film and the LCD or organic EL, and between the transparent conductive film and the cover glass, and the adhesive is activated.
  • the adhesive can be cured and bonded by irradiation with energy rays or heating, and in this way, a member containing the cured product of the adhesive of this embodiment can be manufactured.
  • the member containing the cured adhesive of this embodiment is not particularly limited, and examples thereof include display devices such as liquid crystal displays, plasma displays, organic EL displays, and LED displays.
  • adhesive strength was measured and heat resistance was evaluated according to the following method.
  • Measured method (1) Adhesive strength
  • a PET film was bonded at 23°C at 300 mm/min at 180° using Autograph "AG-IS 5KN" (manufactured by Shimadzu Corporation). The adhesive strength between the glass and the cured adhesive was measured by pulling at an angle.
  • Examples 1 to 3 and Comparative Example 1 The components listed in Table 1 were mixed at 50° C. for Example 1 and Comparative Example 1, and at 25° C. for the other examples in the amounts listed in Table 1 to obtain adhesives. Using the obtained adhesive, it was sandwiched between PET film (manufactured by Toyobo Co., Ltd.) and alkali-free glass (manufactured by As One Corporation) so that the thickness of the adhesive before curing was 100 ⁇ m, and a UV irradiator "CSOT-40D" was used.
  • PET film manufactured by Toyobo Co., Ltd.
  • alkali-free glass manufactured by As One Corporation

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Abstract

La présente invention concerne un agent adhésif présentant une excellente adhésivité et une excellente résistance à la chaleur ; un produit durci de l'agent adhésif et un élément comprenant le produit durci. Plus précisément, l'agent adhésif comprend de 0,05 à 9,5 % en masse d'un composé polymérisable polyfonctionnel (A) représenté par la formule générale (a1) ; et de 90,5 à 99,95 % en masse d'un monomère polymérisable (B). [Dans la formule générale (a1), R1-R3 représentent chacun indépendamment un atome d'hydrogène, un groupe alkyle ayant de 1 à 6 atomes de carbone, un groupe alcényle ayant de 2 à 6 atomes de carbone, un groupe aryle ayant de 6 à 12 atomes de carbone, ou un groupe aralkyle ayant de 7 à 13 atomes de carbone, et R4 représente un groupe (méth)acryloyle, un groupe vinyl-phényle ou un groupe alcényle ayant de 2 à 6 atomes de carbone. N représente un nombre entier de 1 à 6].
PCT/JP2023/032628 2022-09-22 2023-09-07 Agent adhésif, produit durci et élément WO2024062930A1 (fr)

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Citations (5)

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JPS57207664A (en) * 1981-06-01 1982-12-20 Loctite Corp Liquid adhesive and sealant composition
JPH059230A (ja) * 1991-07-01 1993-01-19 Sekisui Chem Co Ltd 光重合性組成物および粘弾性製品の製造方法
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WO2019171989A1 (fr) * 2018-03-09 2019-09-12 富士フイルム株式会社 Film de revêtement dur et film de revêtement dur sur lequel est fixée une couche résistante aux rayures
WO2020262564A1 (fr) * 2019-06-28 2020-12-30 株式会社クラレ Composition durcissable et composition de résine stéréolithographique la comprenant

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