WO2018047903A1 - Composition adhésive acrylique, adhésif, et feuille adhésive - Google Patents

Composition adhésive acrylique, adhésif, et feuille adhésive Download PDF

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Publication number
WO2018047903A1
WO2018047903A1 PCT/JP2017/032257 JP2017032257W WO2018047903A1 WO 2018047903 A1 WO2018047903 A1 WO 2018047903A1 JP 2017032257 W JP2017032257 W JP 2017032257W WO 2018047903 A1 WO2018047903 A1 WO 2018047903A1
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Prior art keywords
meth
sensitive adhesive
pressure
acrylic
ester monomer
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PCT/JP2017/032257
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English (en)
Japanese (ja)
Inventor
鉄也 浅野
貴弘 中島
一樹 野原
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日本合成化学工業株式会社
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Priority to CN201780046953.3A priority Critical patent/CN109563391B/zh
Priority to JP2017547596A priority patent/JP6958358B2/ja
Priority to KR1020197002811A priority patent/KR102340259B1/ko
Publication of WO2018047903A1 publication Critical patent/WO2018047903A1/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
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/08—Homopolymers or copolymers of acrylic acid esters
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • 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
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • 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
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/10—Homopolymers or copolymers of methacrylic acid esters
    • 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
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • 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
    • C09J7/00—Adhesives in the form of films or foils

Definitions

  • the present invention relates to an acrylic pressure-sensitive adhesive composition, a pressure-sensitive adhesive and a pressure-sensitive adhesive sheet comprising the above-mentioned acrylic pressure-sensitive adhesive composition, and in particular, exhibits excellent thermal stability and moist heat resistance, and exhibits a low dielectric constant,
  • the present invention relates to an acrylic pressure-sensitive adhesive composition suitable for thick coating.
  • touch panels that combine liquid crystal displays and position input devices have become widely used in mobile devices such as TVs, monitors for personal computers, notebook computers, mobile phones, and tablet terminals.
  • capacitive touch panels have increased. is doing.
  • the touch panel is usually composed of a liquid crystal display, a transparent conductive film substrate (ITO substrate), and a protective film (glass), and a transparent adhesive sheet is used for bonding these members.
  • a low dielectric constant pressure-sensitive adhesive for example, obtained by polymerizing a monomer component containing as a main component an alkyl (meth) acrylate having a branched alkyl group having 10 to 18 carbon atoms at the terminal of the ester group (meth)
  • a pressure-sensitive adhesive using an acrylic polymer see Patent Document 1, a methacrylic acid alkyl ester monomer having a long-chain alkyl group having 10 or more carbon atoms in the alkyl ester moiety, and 1 to 9 carbon atoms in the alkyl ester moiety
  • a pressure-sensitive adhesive using a copolymer of a monomer mixture (A) containing monomers each containing a specific amount of an alkyl methacrylate monomer having a specific alkyl group is known. Yes.
  • Solventless adhesives that use photopolymerizable unsaturated monomers as dilution monomers instead of solvents used for viscosity adjustment, etc. are used, for example, acrylic resins with dilution monomers and curing components
  • a solventless active energy ray-curable pressure-sensitive adhesive containing a polyfunctional compound is known (see Patent Document 3).
  • the method using a diluted monomer has a problem that durability at a high temperature decreases due to an unreacted monomer remaining in the pressure-sensitive adhesive layer.
  • hot-melt pressure-sensitive adhesives that do not use dilution monomers are used among solventless pressure-sensitive adhesives.
  • the hot-melt pressure-sensitive adhesive can obtain a thick-film pressure-sensitive adhesive layer that is more efficiently excellent in durability at high temperatures.
  • JP 2012-246477 A Japanese Patent Laying-Open No. 2015-40237 JP 2009-57550 A
  • the alkyl (meth) acrylate having a branched alkyl group is easy to extract hydrogen at the branching position, an acrylic resin using a large amount of the alkyl (meth) acrylate having a branched alkyl group has improved thermal stability.
  • the pressure-sensitive adhesive described in Patent Document 1 is not sufficient in terms of thermal stability when used as a hot-melt pressure-sensitive adhesive.
  • the acrylic resin described in Patent Document 2 uses a large amount of methacrylate having a small number of carbon atoms as a monomer of the acrylic resin, the glass transition temperature of the acrylic resin is high, and the hot melt method is used.
  • an acrylic pressure-sensitive adhesive composition that is excellent in thermal stability and heat-and-moisture resistance and that exhibits a low dielectric constant can be obtained and is also suitable for thick coating.
  • the present inventors as a result, in the acrylic pressure-sensitive adhesive composition, as a (meth) acrylic acid alkyl ester monomer, a long-chain and straight-chain alkyl having a certain number of carbon atoms or more.
  • an acrylic resin obtained by copolymerizing a copolymer component containing a (meth) acrylic acid alkyl ester monomer having a group as a main component and further containing a specific amount of a hydroxyl group-containing (meth) acrylic acid ester monomer It has been found that a pressure-sensitive adhesive having excellent thermal stability and heat-and-moisture resistance and a low dielectric constant can be obtained, and an acrylic pressure-sensitive adhesive composition suitable for thick coating can be obtained.
  • the gist of the present invention is an acrylic resin (A) which is a copolymer of a copolymer component containing a hydroxyl group-containing (meth) acrylic acid ester monomer (a1) and a (meth) acrylic acid alkyl ester monomer (a2).
  • the (meth) acrylic acid alkyl ester monomer (a2) is a (meth) acrylic acid alkyl ester monomer (a2-1) having a linear alkyl group having 10 to 24 carbon atoms.
  • An acrylic pressure-sensitive adhesive composition containing 50 to 94% by weight of (a2-1).
  • the present invention also provides a pressure-sensitive adhesive sheet comprising the above-mentioned acrylic pressure-sensitive adhesive composition, and a pressure-sensitive adhesive sheet having a pressure-sensitive adhesive layer composed of the acrylic pressure-sensitive adhesive composition.
  • the acrylic pressure-sensitive adhesive composition of the present invention is an acrylic resin that is a copolymer of a copolymer component containing a hydroxyl group-containing (meth) acrylic acid ester monomer (a1) and a (meth) acrylic acid alkyl ester monomer (a2).
  • a pressure-sensitive adhesive composition comprising (A), wherein the (meth) acrylic acid alkyl ester monomer (a2) has a linear alkyl group having 10 to 24 carbon atoms (meth) acrylic acid alkyl ester monomer (a2) -1), and the copolymerization component is a (meth) acrylic acid having a hydroxyl group-containing (meth) acrylic acid ester monomer (a1) of 5 to 15% by weight and a linear alkyl group having 10 to 24 carbon atoms
  • the alkyl ester monomer (a2-1) is contained in an amount of 50 to 94% by weight.
  • the pressure-sensitive adhesive made of this acrylic pressure-sensitive adhesive composition has no yellowing of the resin due to heating, has excellent thermal stability, exhibits a low dielectric constant, and further has moisture resistance. Excellent heat resistance, shock absorption, and step following ability. And it is useful as an adhesive used especially for bonding of the optical member which comprises a touchscreen, an image display apparatus, etc.
  • the (meth) acrylic acid alkyl ester monomer (a2) in the copolymerization component the (meth) acrylic acid alkyl ester monomer having a linear alkyl group and the alkyl (meth) acrylate having a branched chain-containing alkyl group
  • the content ratio of the ester monomer is 100/0 to 70/30 by weight, the thermal stability is more excellent.
  • the acrylic resin (A) has a weight average molecular weight of 150,000 to 1,500,000, it is more excellent in heat and moisture resistance, shock absorption, and step following ability.
  • the acrylic resin (A) when the acrylic resin (A) has an active energy ray crosslinkable structure site, the acrylic resin (A) can be efficiently cured (crosslinked) and the cohesive force can be increased.
  • the active energy ray crosslinkable structure portion is a benzophenone-based crosslinkable structure
  • the reactivity is excellent and the cohesive force can be further increased.
  • (meth) acryl means acryl or methacryl
  • (meth) acryloyl means acryloyl or methacryloyl
  • (meth) acrylate means acrylate or methacrylate. It is a resin obtained by polymerizing a monomer component containing at least one (meth) acrylic monomer.
  • the “sheet” conceptually includes a sheet, a film, and a tape.
  • the acrylic pressure-sensitive adhesive composition of the present invention comprises a hydroxyl group-containing (meth) acrylic acid ester monomer (a1) of 5 to 15% by weight and a (meth) acrylic acid alkyl ester monomer (a2). It contains an acrylic resin (A) which is a copolymer of a copolymerization component containing 50 to 94% by weight of a (meth) acrylic acid alkyl ester monomer (a2-1) having a chain alkyl group.
  • the hydroxyl group-containing (meth) acrylic acid ester monomer (a1) is usually a hydroxyl group-containing (meth) acrylic group having 5 to 12, preferably 5 to 10 and particularly preferably 5 to 8 carbon atoms from the viewpoint of heat and heat resistance.
  • Acid ester monomers and specific examples include 2-hydroxyethyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 5-hydroxypentyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 8 -Hydroxyalkyl ester of acrylic acid such as hydroxyoctyl (meth) acrylate, caprolactone-modified monomer such as caprolactone-modified 2-hydroxyethyl (meth) acrylate, oxy such as diethylene glycol (meth) acrylate, polyethylene glycol (meth) acrylate, etc.
  • Lukylene-modified monomers other primary hydroxyl group-containing monomers such as 2-acryloyloxyethyl-2-hydroxyethylphthalic acid, N-methylol (meth) acrylamide, hydroxyethylacrylamide; 2-hydroxypropyl (meth) acrylate, 2- Secondary hydroxyl group-containing monomers such as hydroxybutyl (meth) acrylate and 3-chloro-2-hydroxypropyl (meth) acrylate; and tertiary hydroxyl group-containing monomers such as 2,2-dimethyl 2-hydroxyethyl (meth) acrylate. These may be used alone or in combination of two or more.
  • the content of the hydroxyl group-containing (meth) acrylic acid ester monomer (a1) in the copolymer component is preferably 5 to 15% by weight, particularly preferably 8 to 14% by weight, based on the total copolymer component. More preferably, it is 10 to 13% by weight.
  • the content is too small, the moist heat whitening resistance tends to be lowered, and when the content is too large, the dielectric constant tends to be increased.
  • the free acid contained in the hydroxyl group-containing (meth) acrylic acid ester monomer (a1) is preferably 1.0% or less, particularly preferably 0.5% or less, and further preferably 0.1% or less. When there is too much this content, there exists a tendency for the corrosion of a metal-type to-be-adhered body to advance easily, when a heat stability falls and it is set as an adhesive sheet.
  • Examples of the (meth) acrylic acid alkyl ester monomer (a2) include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, iso-butyl (meth) acrylate, and tert-butyl (meth) ) Acrylate, n-propyl (meth) acrylate, n-hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, tridecyl (meth) ) Acrylate, isotridecyl (meth) acrylate, isomyristyl (meth) acrylate, cetyl (meth) acrylate, stearyl (meth) acrylate, isostearyl (meth)
  • the (meth) acrylic acid alkyl ester monomer (a2-1) having a linear alkyl group having 10 to 24 carbon atoms as the (meth) acrylic acid alkyl ester monomer (a2).
  • decyl (meth) acrylate (10 carbon atoms in the alkyl group) lauryl (meth) acrylate (12 carbon atoms), tridecyl (meth) acrylate (13 carbon atoms), hexadecyl (meth) acrylate (16 carbon atoms) ), Stearyl (meth) acrylate (carbon number 18), behenyl (meth) acrylate (carbon number 22), and the like.
  • decyl (meth) acrylate (10 carbon atoms in the alkyl group) lauryl (meth) acrylate (12 carbon atoms), tridecyl (meth) acrylate (13 carbon atoms), hexadecyl (meth) acrylate (16 carbon atoms) ), Ste
  • the dielectric constant can be lowered and the glass transition temperature of the acrylic resin (A) can be lowered.
  • alkyl methacrylate is preferably used, and stearyl methacrylate, lauryl methacrylate, and tridecyl methacrylate are particularly preferable.
  • the content of the (meth) acrylic acid alkyl ester monomer (a2-1) having a linear alkyl group having 10 to 24 carbon atoms is 50 to 94% by weight, preferably 60 to 94% by weight based on the entire copolymerization component. 83% by weight, particularly preferably 70 to 80% by weight. If the content is too small, the dielectric constant tends to increase or the thermal stability of the acrylic resin (A) tends to decrease.
  • the inclusion of the methacrylic acid alkyl ester monomer (a2-2) having an alkyl group having 4 to 8 carbon atoms as the (meth) acrylic acid alkyl ester monomer (a2) improves the cohesive force.
  • the alkyl group of the methacrylic acid alkyl ester monomer (a2-2) having an alkyl group having 4 to 8 carbon atoms may be a linear alkyl group or a branched chain-containing alkyl group.
  • Examples of the methacrylic acid alkyl ester monomer (a2-2) having an alkyl group having 4 to 8 carbon atoms include iso-butyl methacrylate (carbon number 4 of alkyl group), tert-butyl methacrylate (carbon number 4), 2- Examples include ethylhexyl methacrylate (carbon number 8). These may be used alone or in combination of two or more. Among these, monomers having a tertiary carbon in the alkyl group can efficiently extract hydrogen during photocrosslinking to increase cohesion, and other monomers improve cohesion by having a high glass transition temperature. It is something that can be done.
  • tert-butyl methacrylate and 2-ethylhexyl methacrylate can be used because cohesion can be increased while keeping the dielectric constant low. It is preferable to use it.
  • the content of the methacrylic acid alkyl ester monomer (a2-2) having an alkyl group having 4 to 8 carbon atoms is preferably 0.1 to 20% by weight, particularly preferably 1 to It is 18% by weight, more preferably 5 to 15% by weight.
  • the content is too small, the cohesive force tends to decrease, and when the content is too large, the thermal stability decreases and the handling property tends to deteriorate.
  • the (meth) acrylic acid alkyl ester monomer (a2) in the copolymer component the (meth) acrylic acid alkyl ester monomer having a linear alkyl group and the (meth) acrylic having a branched chain-containing alkyl group are used.
  • the content ratio of the acid alkyl ester monomer is preferably 100/0 to 70/30 by weight, particularly preferably 100/0 to 80/20, and more preferably 90/10 to 85/15.
  • a branched chain-containing monomer having a tertiary carbon in the alkyl group or a branched chain having a tert-butyl group is used as a copolymerization component from the viewpoint of efficiently increasing the cohesive force while keeping the dielectric constant low. It is preferable to contain a small amount of a (meth) acrylic acid alkyl ester monomer (a2) having a branched chain-containing alkyl group, such as a containing monomer.
  • a branched chain-containing monomer having a tertiary carbon in the alkyl group can efficiently extract hydrogen during photocrosslinking and increase cohesion.
  • a tert-butyl group such as tert-butyl (meth) acrylate can be used.
  • the branched chain-containing monomer has an ability to improve cohesion by increasing the glass transition temperature.
  • iso-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, and tert-butyl (meth) acrylate may be used as the (meth) acrylic acid alkyl ester monomer (a2) having a branched chain-containing alkyl group.
  • Particularly preferred is 2-ethylhexyl (meth) acrylate or tert-butyl (meth) acrylate.
  • the acrylic resin (A) used in the present invention has an active energy ray crosslinkable structure site in that the acrylic resin can be efficiently cured (crosslinked) and the cohesive force can be increased.
  • the active energy ray crosslinkable structural site is a structural site that can react with a part of the acrylic resin (A) or other curing component contained in the acrylic resin composition to form a crosslinked structure by irradiation with active energy rays. It is.
  • the active energy ray crosslinkable structure site is preferably a benzophenone-based crosslinkable structure in terms of high reactivity and excellent cohesive strength.
  • an active energy ray crosslinkable structure site-containing (meth) acrylic acid ester monomer (a3) as a copolymerization component of the acrylic resin (A).
  • an active energy ray crosslinkable structure site-containing (meth) acrylic acid ester monomer (a3) containing an active energy ray-crosslinkable structure site it is more efficient to contain a (meth) acrylic acid ester monomer having a benzophenone structure by active energy rays such as ultraviolet rays and electron beams.
  • active energy rays such as ultraviolet rays and electron beams.
  • specific examples include 4- (meth) acryloyloxybenzophenone.
  • the content of the active energy ray crosslinkable structure site-containing (meth) acrylic acid ester monomer (a3) is preferably 0.01 to 5% by weight with respect to the entire copolymer component, and in particular, the benzophenone structure
  • the content of the (meth) acrylic acid ester monomer having is preferably from 0.01 to 5% by weight, particularly preferably from 0.1 to 2% by weight, more preferably based on the entire copolymer component. 0.2 to 1% by weight.
  • the holding power when forming a crosslinked structure with active energy rays tends to decrease, and furthermore, in order to create a pressure-sensitive adhesive sheet that can be processed, when forming the crosslinked structure, the active energy A large amount of dose is required, and a large amount of energy is required at the time of preparing the pressure-sensitive adhesive sheet, which tends to make it difficult to produce efficiently.
  • the cohesion force of the whole system will rise too much, and there exists a tendency for adhesive force to fall.
  • copolymerizable ethylenically unsaturated monomer (a4) examples include, for example, phenyl (meth) acrylate, benzyl (meth) acrylate, phenoxyethyl (meth) acrylate, phenyldiethylene glycol (meth) acrylate, 2-hydroxy-3 -Aromatic rings such as phenoxypropyl (meth) acrylate, phenoxypolyethylene glycol (meth) acrylate, phenoxypolyethylene glycol-polypropylene glycol- (meth) acrylate, orthophenylphenoxyethyl (meth) acrylate, nonylphenol ethylene oxide adduct (meth) acrylate, etc.
  • cyclohexyl (meth) acrylate, cyclohexyloxyalkyl (meth) acrylate, tert-butylcyclohexyl Alicyclic ring-containing monomers such as xylethyl (meth) acrylate, isobornyl (meth) acrylate, dicyclopentanyl (meth) acrylate; 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 3-methoxybutyl ( (Meth) acrylate, 2-butoxyethyl (meth) acrylate, 2-butoxydiethylene glycol (meth) acrylate, methoxydiethylene glycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, methoxydipropylene glycol ( (Meth) acrylate, meth
  • a compound having two or more ethylenically unsaturated groups such as propylene glycol di (meth) acrylate and divinylbenzene can also be used in combination.
  • the content of the other copolymerizable ethylenically unsaturated monomer (a4) is preferably 0 to 20% by weight, particularly preferably 0 to 10% by weight, more preferably 0%, based on the entire copolymerization component. ⁇ 5% by weight. If the content is too large, the thermal stability tends to decrease or the adhesive strength tends to decrease.
  • the content is 0 to 0.1% by weight based on the entire copolymerization component. It is preferably 0 to 0.07% by weight, more preferably 0 to 0.05% by weight. When there is too much this content, there exists a possibility of corroding or deteriorating the metal or metal oxide of adherends, such as an ITO film
  • the acrylic resin (A) used in the present invention comprises the hydroxyl group-containing (meth) acrylic acid ester monomer (a1) and a (meth) acrylic acid alkyl ester monomer having a linear alkyl group having 10 to 24 carbon atoms ( It can be produced by using a2-1) as an essential component and appropriately selecting and polymerizing the above optional polymerization components.
  • a polymerization method of the acrylic resin (A) for example, conventionally known polymerization methods such as solution polymerization, suspension polymerization, bulk polymerization, and emulsion polymerization can be used. In the present invention, the polymerization is performed by solution polymerization. It is preferable that the acrylic resin (A) can be produced safely and stably with an arbitrary monomer composition.
  • an example of the preferable manufacturing method of acrylic resin (A) used by this invention is shown.
  • a copolymer component and a polymerization initiator are mixed or dropped in an organic solvent, and solution polymerization is performed to obtain an acrylic resin (A) solution.
  • Organic solvent examples include aromatic hydrocarbons such as toluene and xylene, aliphatic hydrocarbons such as n-hexane, esters such as methyl acetate, ethyl acetate, and butyl acetate, and methyl alcohol.
  • Aliphatic alcohols such as ethyl alcohol, n-propyl alcohol, isopropyl alcohol, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, aliphatic ethers such as dimethyl ether, diethyl ether, methylene chloride, ethylene chloride, etc.
  • Examples thereof include aliphatic halogenated hydrocarbons and cyclic ethers such as tetrahydrofuran.
  • these solvents a solvent having a boiling point of 70 ° C. or less is used in that a solvent-free acrylic resin can be efficiently produced by distilling off the solvent from the acrylic resin solution obtained by solution polymerization. preferable.
  • Examples of the organic solvent having a boiling point of 70 ° C. or lower include hydrocarbons such as n-hexane (67 ° C.), aliphatic alcohols such as methanol (65 ° C.), and methyl acetate (54 ° C.). Esters, ketones such as acetone (56 ° C), aliphatic ethers such as diethyl ether (35 ° C), aliphatic halogenated hydrocarbons such as methylene chloride (40 ° C), tetrahydrofuran (66 ° C) In particular, acetone and methyl acetate are preferably used from the viewpoint of versatility and safety, and acetone is particularly preferable. In addition, the numerical value in () described following each said organic solvent name is a boiling point.
  • the acrylic resin (A) used in the present invention it is preferable to carry out the polymerization at a relatively low temperature using an organic solvent having a boiling point of 70 ° C. or lower as a reaction solvent for solution polymerization.
  • an organic solvent having a boiling point of 70 ° C. or lower as a reaction solvent for solution polymerization.
  • the polymerization initiator tends to remain. If the polymerization initiator remains, gelation of the acrylic resin (A) tends to occur in the step of distilling off the solvent from the acrylic resin (A) solution described later.
  • the amount of the polymerization initiator used is usually 0.001 to 10 parts by weight, preferably 0.1 to 8 parts by weight, particularly preferably 0.5 to 6 parts by weight per 100 parts by weight of the copolymer component. Parts, more preferably 1 to 4 parts by weight, particularly preferably 1.5 to 3 parts by weight, most preferably 2 to 2.5 parts by weight. If the amount of the polymerization initiator used is too small, the polymerization rate of the acrylic resin (A) will decrease, the residual monomer will increase, or the weight average molecular weight of the acrylic resin (A) will tend to increase. If the amount is too large, gelation of the acrylic resin (A) tends to occur in the step of distilling off the solvent from the acrylic resin (A) solution described later.
  • the acrylic resin (A) of the present invention in order to reduce the amount of the residual polymerization initiator, it is preferable to perform additional heating in order to thermally decompose the polymerization initiator.
  • the temperature at which the solvent is distilled off by heating is preferably 60 to 150 ° C., and in particular, the reaction solution after polymerization of the acrylic resin (A) is maintained at 60 to 80 ° C. And then distilling the solvent at 80 to 150 ° C. is preferable in that the amount of the remaining solvent is extremely reduced. In addition, from the point which suppresses gelatinization of acrylic resin (A), it is preferable not to perform the temperature in the case of solvent distillation at 150 degreeC or more.
  • the acrylic resin (A) used in the present invention preferably has a glass transition temperature (Tg) of ⁇ 100 to 50 ° C., particularly ⁇ 50 to 20 ° C., more preferably ⁇ 20 to 0 ° C. preferable. If the glass transition temperature is too high, the melt viscosity of the acrylic resin (A) becomes high, so that the heating temperature required at the time of coating becomes high, which may impair the stability of the acrylic resin (A). There is a tendency for the step following ability and the adhesive strength to decrease. If the glass transition temperature is too low, the thermal durability tends to decrease.
  • Tg glass transition temperature
  • ⁇ Measurement condition Measuring instrument: DVA-225 (made by IT-Measurement Control) Deformation mode: Shear Strain: 0.1% Measurement temperature: -100 ⁇ 20 °C Measurement frequency: 1Hz
  • the acrylic resin (A) has a melt viscosity (mPa ⁇ s) at 100 ° C. of preferably 1,000 to 10,000,000 mPa ⁇ s, particularly preferably 50,000 to 1,000,000 mPa ⁇ s, Preferably, it is 200,000 to 600,000 mPa ⁇ s. If the viscosity is too low, the durability tends to decrease due to a decrease in molecular weight. If the viscosity is too high, the handleability tends to decrease and coating tends to be difficult.
  • mPa ⁇ s melt viscosity
  • said viscosity is the value which measured the load 30kg, the orifice diameter 1.0mm, die
  • the solvent content and the amount of residual monomer in the acrylic resin (A) were obtained by diluting the acrylic resin (A) 20 times with toluene, and using a gas chromatograph / mass fragment detector (GC: 7890A GCsystem manufactured by Agilent Technologies, MSD: a value measured using Agilent Technologies 5975inert).
  • GC gas chromatograph / mass fragment detector
  • auxiliary agents for these photopolymerization initiators (B) include triethanolamine, triisopropanolamine, 4,4′-dimethylaminobenzophenone (Michler ketone), 4,4′-diethylaminobenzophenone, 2-dimethylaminoethylbenzoic acid.
  • active energy ray-curable monomers such as a monofunctional monomer and a polyfunctional monomer
  • active energy ray-curable monomers can be further contained.
  • the active energy ray-curable monomer is preferably a polyfunctional monomer containing two or more ethylenically unsaturated groups in one molecule.
  • the acrylic pressure-sensitive adhesive composition of the present invention may be blended with other pressure-sensitive adhesives as necessary, or a crosslinking agent, a crosslinking accelerator, a silane coupling agent, an antistatic agent, a tackifier, or a functional dye.
  • a conventionally known additive such as may be blended.
  • the acrylic pressure-sensitive adhesive composition of the present invention is a pressure-sensitive adhesive sheet in which a pressure-sensitive adhesive layer using the same is provided on a base sheet, a double-sided pressure-sensitive adhesive sheet in which a pressure-sensitive adhesive layer is provided on a release sheet, and an optical pressure-sensitive adhesive layer. It is preferably used as an optical member with an adhesive layer provided on the member.
  • the pressure-sensitive adhesive layer may be the acrylic pressure-sensitive adhesive composition itself of the present invention or may be formed by curing (crosslinking) the acrylic pressure-sensitive adhesive composition of the present invention. Examples of the curing method include a method of curing with active energy rays. By irradiating with active energy rays, the acrylic resin (A) in the acrylic pressure-sensitive adhesive composition is cross-linked at least either within the molecule or between the molecules. Form a structure.
  • rays such as far ultraviolet rays, ultraviolet rays, near ultraviolet rays, infrared rays, electromagnetic waves such as X-rays and ⁇ rays, electron beams, proton rays, neutron rays, etc. can be used. Curing by ultraviolet irradiation is advantageous because of the availability of the irradiation device and the price.
  • optical member examples include a liquid crystal display, a transparent conductive film substrate (ITO substrate), and a protective film (glass) that constitute a touch panel and an image display device.
  • ITO substrate transparent conductive film substrate
  • glass protective film
  • the gel fraction is a measure of the degree of crosslinking (curing degree), and is calculated, for example, by the following method. That is, a 200-mesh SUS metal mesh is used to wrap a pressure-sensitive adhesive sheet (without a release sheet) in which a pressure-sensitive adhesive layer is formed on a polymer sheet (eg, polyethylene terephthalate (PET) film).
  • PET polyethylene terephthalate
  • the weight percentage of the insoluble pressure-sensitive adhesive component remaining in the wire mesh is immersed in toluene maintained at 23 ° C. for 24 hours, and is defined as a gel fraction. However, the weight of the substrate is subtracted.
  • the acrylic resin [A-1] solution obtained above was used in a flask in which the solvent could be distilled out of the system by using a toroidal connecting tube, at a jacket temperature of 80 ° C. for 1 hour, and further The pressure was reduced to 10 kPa, and the jacket temperature was maintained at 90 ° C. for 2 hours to distill off the solvent.
  • the acrylic resin [A-1] (weight average molecular weight: 339000, volatile content: 0.9%, A glass transition temperature of ⁇ 8.9 ° C.) was obtained.
  • Example 1 The acrylic resin [A-1] obtained above was sandwiched between two polyester release sheets (thickness: 176 ⁇ m) and pressed while heating at 100 ° C. so that the thickness of the adhesive layer was 175 ⁇ m.
  • the substrate-less double-sided pressure-sensitive adhesive sheet was obtained by performing ultraviolet irradiation with a high-pressure mercury UV irradiation apparatus at a peak illuminance of 150 mW / cm 2 and an integrated exposure amount of 1000 mJ / cm 2 (500 mJ / cm 2 ⁇ 2 passes).
  • the release sheet on one side is peeled off from the pressure-sensitive adhesive layer of the substrate-less double-sided pressure-sensitive adhesive sheet obtained above, and pressed onto an easy-adhesion-treated polyethylene terephthalate (PET) film (thickness 125 ⁇ m), and the thickness of the pressure-sensitive adhesive layer Gave a PET film with an adhesive layer of 175 ⁇ m.
  • PET polyethylene terephthalate
  • Example 1 In Example 1, except that the acrylic resin [A-1] was changed to the acrylic resin [A′-1], the substrate-less double-sided pressure-sensitive adhesive sheet and adhesive of Comparative Example 1 were used in the same manner as in Example 1. A PET film with an agent layer was obtained.
  • UV irradiation was performed with a UV irradiation apparatus at a peak illuminance of 150 mW / cm 2 and an integrated exposure amount of 2000 mJ / cm 2 (1000 mJ / cm 2 ⁇ 2 passes), and left for 30 minutes at 23 ° C. ⁇ 50% RH Thereafter, the 180 ° peel strength (N / 25 mm) was measured at a peel rate of 300 mm / min at room temperature (23 ° C.).
  • haze value Using the obtained test piece, haze value, total light transmittance, color difference b * value, and YI value were measured. [Haze value and total light transmittance]
  • diffuse transmittance and total light transmittance are measured using HAZE MATER NDH2000 (manufactured by Nippon Denshoku Industries Co., Ltd.), and the obtained diffuse transmittance and total light transmittance value are substituted into the following formula.
  • the haze value was calculated. This machine conforms to JIS K7361-1.
  • Rate of increase (%) (haze value after test ⁇ haze value before test) / haze value before test ⁇ 100
  • alkali-free glass Corning Corp., Eagle XG
  • autoclaved 50 ° C. ⁇ 0.5 MPa ⁇ 20 minutes
  • a thermal stability test for 168 hours was performed in an atmosphere of 150 ° C.
  • a b * value after the thermal stability test was measured, and evaluated according to the following criteria.
  • the b * value was measured by the same method as the measurement of the optical properties of the pressure-sensitive adhesive layer. (Evaluation) ⁇ ... b * value immediately after thermal stability test is 0.5 or less ⁇ ... b * value immediately after thermal stability test is greater than 0.5
  • the release sheet on one side is peeled off from the pressure-sensitive adhesive layer of the substrate-less double-sided pressure-sensitive adhesive sheet and pressed onto an untreated PET film (thickness 50 ⁇ m), and then the other release sheet is peeled off and the same untreated PET film as above.
  • an adhesive layer having a configuration of “PET film / adhesive layer / PET film”.
  • the PET film with the pressure-sensitive adhesive layer is cut into 7 cm ⁇ 7 cm, and irradiated with ultraviolet rays at a peak illuminance of 150 mW / cm 2 and an integrated exposure amount of 2000 mJ / cm 2 (1000 mJ / cm 2 ⁇ 2 passes) using a high-pressure mercury UV irradiation apparatus. Went.
  • the test piece for dielectric constant measurement using an HP4284A Precision LCR meter (manufactured by Agilent), the test piece is sandwiched between electrodes in an atmosphere of 23 ° C. ⁇ 50% RH and an electric field is applied at a frequency of 100 Hz to measure the capacitance.
  • the relative dielectric constant of the adhesive layer at 100 KHz is 3.0 or less.
  • ⁇ ... The relative dielectric constant of the adhesive layer at 100 KHz is greater than 3.0.
  • the pressure-sensitive adhesive sheets using the pressure-sensitive adhesive compositions of Examples 1 and 2 were excellent in a well-balanced thermal stability and heat-and-moisture resistance while being low dielectric.
  • Comparative Example 1 in which the content of the hydroxyl group-containing (meth) acrylic acid ester monomer (a1) is small, the heat and moisture resistance was poor.
  • Comparative Example 2 in which the content of the linear (meth) acrylic acid alkyl ester monomer (a2-1) having an alkyl group having 10 to 24 carbon atoms is small, the thermal stability is poor and the relative dielectric constant is also low. It was expensive.
  • the acrylic pressure-sensitive adhesive composition of the present invention can be applied by thick coating, and the pressure-sensitive adhesive using the acrylic pressure-sensitive adhesive composition is excellent in thermal stability without yellowing of the resin due to heating and exhibiting a low dielectric constant.
  • it since it is also excellent in moisture and heat resistance, shock absorption, and step followability, it is particularly useful as an adhesive used for bonding optical members that constitute touch panels, image display devices, etc., and for sealing organic EL displays. .

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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)
  • Adhesive Tapes (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne une composition adhésive acrylique qui est appropriée pour des revêtements épais, et à partir de laquelle un adhésif ayant une excellente stabilité thermique et une excellente résistance à l'humidité et à la chaleur, et présentant une faible constante diélectrique, peut être obtenu. La composition adhésive contient une résine acrylique (A) qui est un copolymère de composants copolymérisables contenant un monomère d'ester d'acide (méth)acrylique contenant un groupe hydroxyle (a1) et un monomère d'ester alkylique d'acide (méth)acrylique (a2), le monomère d'ester alkylique d'acide (méth)acrylique (a2) contenant un monomère d'ester alkylique d'acide (méth)acrylique (a2-1) ayant un groupe alkyle linéaire ayant de 10 à 24 atomes de carbone, et les composants copolymérisables contenant 5 à 15 % en poids d'un monomère d'ester d'acide (méth)acrylique contenant un groupe hydroxyle (a1) et 50 à 94 % en poids d'un monomère ester alkylique d'acide (méth)acrylique (a2-1) ayant un groupe alkyle linéaire ayant de 10 à 24 atomes de carbone.
PCT/JP2017/032257 2016-09-09 2017-09-07 Composition adhésive acrylique, adhésif, et feuille adhésive WO2018047903A1 (fr)

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CN201780046953.3A CN109563391B (zh) 2016-09-09 2017-09-07 丙烯酸系粘合剂组合物、粘合剂及粘合片
JP2017547596A JP6958358B2 (ja) 2016-09-09 2017-09-07 アクリル系粘着剤組成物、粘着剤及び粘着シート
KR1020197002811A KR102340259B1 (ko) 2016-09-09 2017-09-07 아크릴계 점착제 조성물, 점착제 및 점착 시트

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US20230050611A1 (en) * 2019-12-10 2023-02-16 Lg Chem, Ltd. Pressure-sensitive adhesive layer
WO2024195441A1 (fr) * 2023-03-22 2024-09-26 三菱ケミカル株式会社 Feuille adhésive, feuille adhésive avec film de démoulage, feuille adhésive pour composant de dispositif d'affichage d'image flexible, stratifié pour dispositif d'affichage d'image, dispositif d'affichage d'image flexible, feuille adhésive photodurcissable et composition adhésive

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KR102229883B1 (ko) * 2020-07-01 2021-03-18 동우 화인켐 주식회사 점착제 조성물 및 그를 이용한 점착 시트

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WO2024195441A1 (fr) * 2023-03-22 2024-09-26 三菱ケミカル株式会社 Feuille adhésive, feuille adhésive avec film de démoulage, feuille adhésive pour composant de dispositif d'affichage d'image flexible, stratifié pour dispositif d'affichage d'image, dispositif d'affichage d'image flexible, feuille adhésive photodurcissable et composition adhésive

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CN109563391B (zh) 2021-04-13
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TW201817841A (zh) 2018-05-16
TWI735646B (zh) 2021-08-11
KR102340259B1 (ko) 2021-12-16
JPWO2018047903A1 (ja) 2019-06-24
CN109563391A (zh) 2019-04-02

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