WO2021085136A1 - 粘着剤組成物、粘着シートおよび光学部材 - Google Patents

粘着剤組成物、粘着シートおよび光学部材 Download PDF

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WO2021085136A1
WO2021085136A1 PCT/JP2020/038756 JP2020038756W WO2021085136A1 WO 2021085136 A1 WO2021085136 A1 WO 2021085136A1 JP 2020038756 W JP2020038756 W JP 2020038756W WO 2021085136 A1 WO2021085136 A1 WO 2021085136A1
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meth
sensitive adhesive
pressure
mass
copolymer
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PCT/JP2020/038756
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English (en)
French (fr)
Japanese (ja)
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雄也 米川
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綜研化学株式会社
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Priority to JP2021554323A priority Critical patent/JPWO2021085136A1/ja
Priority to CN202080073345.3A priority patent/CN114599756A/zh
Priority to KR1020227012308A priority patent/KR20220062091A/ko
Publication of WO2021085136A1 publication Critical patent/WO2021085136A1/ja

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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
    • C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0025—Crosslinking or vulcanising agents; including accelerators
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/15—Heterocyclic compounds having oxygen in the ring
    • C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
    • C08K5/1515—Three-membered rings
    • 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
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/08—Macromolecular additives
    • 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
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements

Definitions

  • One embodiment of the present invention relates to an adhesive composition, an adhesive sheet or an optical member.
  • the touch panel is a laminate of various materials, and an adhesive composition is used for bonding the various materials.
  • the development of touch panels for in-vehicle devices is also expanding, and because the touch panel is placed in a high-temperature and high-humidity environment in the summer, the adhesive composition for that application is required to have more humidity and heat resistance than general applications. Be done.
  • Various adhesive compositions have been conventionally studied (see, for example, Patent Documents 1 and 2).
  • an adhesive composition having excellent various performances such as blister resistance, whitening resistance and adhesiveness is required.
  • One embodiment of the present invention provides a pressure-sensitive adhesive composition capable of forming a pressure-sensitive adhesive layer having excellent various performances such as blister resistance, whitening resistance, and adhesive strength in a high-temperature and high-humidity environment.
  • the present inventors have conducted diligent studies to solve the above problems. As a result, they have found that a pressure-sensitive adhesive composition having the following constitution can solve the above-mentioned problems, and have completed the present invention.
  • the present invention relates to, for example, the following [1] to [5].
  • an adhesive layer having excellent various performances such as blister resistance and whitening resistance in a high temperature and high humidity environment such as 85 ° C./85% RH (relative humidity), and adhesive strength.
  • a suitable pressure-sensitive adhesive composition can be provided.
  • acrylic and methacrylic are collectively referred to as “(meth) acrylic", and acrylate and methacrylate are also collectively referred to as “(meth) acrylate”.
  • the pressure-sensitive adhesive composition includes a (meth) acrylic copolymer (A) (also simply referred to as “copolymer (A)”) and a (meth) acrylic copolymer, which will be described below. It contains a copolymer (B) (also simply referred to as “copolymer (B)”) and a cross-linking agent (C).
  • A acrylic copolymer
  • B copolymer
  • C cross-linking agent
  • the total content of the copolymer (A), the copolymer (B), and the cross-linking agent (C) in the pressure-sensitive adhesive composition is usually 60% by mass or more in 100% by mass of the solid content of the pressure-sensitive adhesive composition. , It is preferably 65% by mass or more, and more preferably 70% by mass or more.
  • the solid content is a component excluding the organic solvent.
  • the (meth) acrylic copolymer (A) contains 50 to 97% by mass of the alkoxyalkyl (meth) acrylate (a1) and 3 to 10% by mass of the carboxy group or acid anhydride group-containing monomer (a2). It is a copolymer of a monomer component, and is obtained by copolymerizing the monomer component.
  • the monomer component usually consists of a polymerizable double bond-containing monomer.
  • the copolymer (A) one kind or two or more kinds can be used.
  • Alkoxyalkyl (meth) acrylate (a1) By using the copolymer (A) having a structural unit derived from alkoxyalkyl (meth) acrylate (a1) as a main component, the water absorption of the obtained pressure-sensitive adhesive layer is improved, and the pressure-sensitive adhesive layer is used in a high humidity environment. The water absorbed therein is dispersed in the pressure-sensitive adhesive layer, and the whitening phenomenon caused by the water can be suppressed, and the blister phenomenon can also be suppressed. When the pressure-sensitive adhesive layer according to the embodiment of the present invention is formed on a highly breathable adherend such as a polycarbonate substrate, the moisture brought from the adherend can be dissolved and trapped by the pressure-sensitive adhesive layer. Therefore, the effect tends to be more prominent.
  • a highly breathable adherend such as a polycarbonate substrate
  • the copolymer (A) having a structural unit derived from alkoxyalkyl (meth) acrylate (a1) as a main component the wettability of the obtained pressure-sensitive adhesive layer to the adherend surface is lowered. Since the adhesive strength immediately after application is suppressed to a low level, the reworkability of the adhesive sheet tends to be improved.
  • the number of carbon atoms of the alkoxyalkyl group in the alkoxyalkyl (meth) acrylate (a1) is usually 2 to 18, preferably 2 to 12, and more preferably 2 to 10.
  • Examples of the alkoxyalkyl (meth) acrylate (a1) include methoxymethyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 3-methoxypropyl (meth) acrylate, and 3-. Examples thereof include ethoxypropyl (meth) acrylate, 4-methoxybutyl (meth) acrylate, and 4-ethoxybutyl (meth) acrylate.
  • the copolymer (A) can have one or more structural units derived from the alkoxyalkyl (meth) acrylate (a1).
  • the amount of alkoxyalkyl (meth) acrylate (a1) in all the monomer components used to obtain the copolymer (A) is 50 to 97% by mass, preferably 55 to 96% by mass, and more preferably 60 to 60. It is 95% by mass.
  • the amount of the alkoxyalkyl (meth) acrylate (a1) is at least the above lower limit value, the moisture that has penetrated into the pressure-sensitive adhesive layer can be efficiently dispersed, and the whitening resistance and the blister resistance are increased, and below the above upper limit value. If it is, it is advantageous for increasing the adhesive strength.
  • the copolymer (A) contains a structural unit derived from the alkoxyalkyl (meth) acrylate (a1), preferably 50 to 97% by mass, more preferably 55 to 96% by mass, and further preferably 60 to 95% by mass. Have%.
  • the amount of the structural unit can be grasped from, for example, the amount of the monomer component charged. The same applies to other structural unit quantities.
  • Examples of the carboxy group or acid anhydride group-containing monomer (a2) include carboxy group-containing monomers such as (meth) acrylic acid, itaconic acid, crotonic acid, fumaric acid, and maleic acid; phthalic anhydride, maleic anhydride, and the like. Acid anhydride group-containing monomer; ⁇ -carboxyethyl (meth) acrylate, 5-carboxypentyl (meth) acrylate, mono (meth) acryloyloxyethyl ester of succinate, ⁇ -carboxypolycaprolactone mono (meth) acrylate, etc. Examples include carboxy group-containing (meth) acrylates.
  • the copolymer (A) can have a structural unit derived from one or more carboxy groups or acid anhydride group-containing monomers (a2).
  • the amount of the carboxy group or acid anhydride group-containing monomer (a2) in all the monomer components used to obtain the copolymer (A) is 3 to 10% by mass, preferably 4 to 8% by mass, and more preferably. Is 5 to 8% by mass.
  • the copolymer (A) contains a structural unit derived from the carboxy group or acid anhydride group-containing monomer (a2), preferably 3 to 10% by mass, more preferably 4 to 8% by mass, and further preferably 5. Has ⁇ 8% by mass.
  • the copolymer (A) obtained by copolymerizing the carboxy group or acid anhydride group-containing monomer (a2) in the above amount the wettability of the obtained pressure-sensitive adhesive layer to the adherend surface is lowered. Since the adhesive strength immediately after sticking is suppressed to a low level, the reworkability of the adhesive sheet tends to be improved.
  • the obtained pressure-sensitive adhesive layer is formed after a certain period of time has passed from the attachment to the adherend. Adhesive strength increases and tends to develop high adhesive strength.
  • the copolymer (A) may have a structural unit derived from a monomer other than the above-mentioned (a1) to (a2).
  • examples of other monomers include alkyl (meth) acrylates, alicyclic hydrocarbon groups or aromatic hydrocarbon group-containing (meth) acrylates, alkoxypolyalkylene glycol mono (meth) acrylates, styrene-based monomers, and hydroxyl group-containing monomers.
  • examples thereof include an amino group-containing monomer, an amide group-containing monomer, a nitrogen-based heterocyclic ring-containing monomer, a cyano group-containing monomer, vinyl acetate, and a polymerizable macromonomer.
  • the number of carbon atoms of the alkyl group in the alkyl (meth) acrylate is preferably 1 to 20.
  • the alkyl (meth) acrylate include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, iso-propyl (meth) acrylate, n-butyl (meth) acrylate, and iso-butyl (iso-butyl).
  • Examples of the alicyclic hydrocarbon group or aromatic hydrocarbon group-containing (meth) acrylate include cyclohexyl (meth) acrylate, benzyl (meth) acrylate, and phenyl (meth) acrylate.
  • alkoxypolyalkylene glycol mono (meth) acrylate examples include methoxydiethylene glycol mono (meth) acrylate, methoxydipropylene glycol mono (meth) acrylate, ethoxytriethylene glycol mono (meth) acrylate, and ethoxydiethylene glycol mono (meth) acrylate. Examples thereof include methoxytriethylene glycol mono (meth) acrylate.
  • styrene-based monomer examples include styrene; alkyl styrene such as methyl styrene, dimethyl styrene, trimethyl styrene, propyl styrene, butyl styrene, hexyl styrene, heptyl styrene, and octyl styrene; fluorostyrene, chloro styrene, bromo styrene, and dibromo styrene.
  • halogenated styrene such as halogenated styrene
  • functionalized styrene such as nitrostyrene, acetylstyrene, and methoxystyrene.
  • hydroxyl group-containing monomer examples include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroshikibutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, and 8-hydroxyoctyl ( Examples thereof include hydroxyl group-containing (meth) acrylates such as hydroxyalkyl (meth) acrylates such as meta) acrylates.
  • Examples of the amino group-containing monomer include N, N-dialkylaminoalkyl (meth) acrylates such as N, N-dimethylaminoethyl (meth) acrylate and N, N-diethylaminoethyl (meth) acrylate.
  • Examples of the amide group-containing monomer include N-alkyl such as (meth) acrylamide, N-methyl (meth) acrylamide, N-ethyl (meth) acrylamide, N-propyl (meth) acrylamide, and N-hexyl (meth) acrylamide.
  • N, N-dialkyl (meth) acrylamide such as N, N-dimethyl (meth) acrylamide and N, N-diethyl (meth) acrylamide can be mentioned.
  • nitrogen-based heterocyclic-containing monomer include N-vinylpyrrolidone, N-vinylcaprolactam, and (meth) acryloylmorpholine.
  • cyano group-containing monomer include cyano (meth) acrylate, acrylonitrile, and methacrylonitrile.
  • Examples of the monomer of the polymer chain (main chain) portion constituting the polymerizable macromonomer include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, iso-butyl (meth) acrylate and Examples thereof include alkyl (meth) acrylates such as tert-butyl (meth) acrylates, and the alkyl group preferably has 1 to 20 carbon atoms, and (meth) acrylonitrile; styrene, ⁇ -methylstyrene and the like. A styrene-based monomer can also be mentioned.
  • the macromonomer for example, (meth) acrylic macromonomer, (meth) acrylonitrile-based macromonomer, and styrene-based macromonomer are preferable.
  • alkyl (meth) acrylates alicyclic hydrocarbon groups or aromatic hydrocarbon group-containing (meth) acrylates, and styrene-based monomers are preferable, and alkyl (meth) acrylates are more preferable.
  • the copolymer (A) can have a structural unit derived from one or more other monomers.
  • the amount of other monomers in the total monomer components used to obtain the copolymer (A) is preferably 47% by mass or less, more preferably 41% by mass or less, still more preferably 35% by mass or less. Further, in the copolymer (A), the amount of structural units derived from other monomers is preferably 47% by mass or less, more preferably 41% by mass or less, and further preferably 35% by mass or less.
  • the weight average molecular weight (Mw) of the copolymer (A) measured by the gel permeation chromatography (GPC) method is usually 200,000 to 2 million, preferably 400,000 to 1.5 million, and more preferably 500,000 to 500,000. It is one million. In such an embodiment, there is a tendency to obtain a pressure-sensitive adhesive composition having excellent high-temperature durability.
  • the molecular weight distribution (Mw / Mn) of the copolymer (A), which is the ratio of Mw to the number average molecular weight (Mn), is usually 2 to 15, preferably 2.5 to 10, and more preferably 3 to 8. Is. In such an embodiment, there is a tendency to obtain a pressure-sensitive adhesive composition having excellent high-temperature durability. Mw and Mw / Mn can be measured, for example, by the method described in Examples.
  • the glass transition temperature (Tg) of the copolymer (A) is usually ⁇ 70 ° C. or higher and lower than 0 ° C., preferably ⁇ 70 to ⁇ 30 ° C. In such an embodiment, there is a tendency to obtain a pressure-sensitive adhesive composition having excellent adhesive strength at room temperature.
  • the glass transition temperature can be calculated by the so-called Fox formula. The same applies to the (meth) acrylic copolymer (B) described later.
  • Tg is the glass transition temperature (K) of the (meth) acrylic copolymer (A)
  • Tg 1 , Tg 2 , ..., Tg m are the glass transition temperatures of the homopolymer formed from each monomer.
  • K glass transition temperature
  • W 1 , W 2 , ..., W m are the mass fractions of the structural units derived from each monomer in the copolymer (A).
  • the charging ratio of each monomer to all the monomers at the time of copolymer synthesis can be used.
  • the glass transition temperature (Tg) of the homopolymer formed from each monomer for example, the value described in Polymer Handbook Fourth Edition (Wiley-Interscience 2003) can be adopted.
  • the copolymer (A) can be produced by a known method, and is preferably produced by solution polymerization. Specifically, a monomer component and a polymerization solvent are charged in a reaction vessel, a polymerization initiator is added, and the mixture is heated to a reaction temperature of about 50 to 90 ° C. and reacted for 2 to 20 hours. For example, the polymerization is carried out in an atmosphere of an inert gas such as nitrogen gas. Further, a polymerization initiator, a chain transfer agent, a monomer component, and a polymerization solvent may be additionally added as appropriate during the polymerization reaction.
  • Examples of the polymerization solvent include organic solvents described later.
  • Examples of the polymerization initiator include organic polymerization initiators, specifically, peroxides such as benzoyl peroxide and lauroyl peroxide, and azo compounds such as 2,2'-azobisisobutyronitrile. Can be mentioned. Among these, the azo compound is preferable. One kind or two or more kinds of polymerization initiators can be used.
  • the amount of the polymerization initiator used is usually 0.01 to 5 parts by mass with respect to 100 parts by mass of the monomer component.
  • the Mw of the copolymer (A) can be adjusted within an appropriate range.
  • the (meth) acrylic copolymer (B) is a copolymer of a monomer component containing an amino group-containing monomer (b1) in an amount of 1 to 10% by mass, and is obtained by copolymerizing the monomer component and having a glass transition temperature. Is 0 ° C. or higher.
  • the copolymer (B) is a copolymer other than the copolymer (A).
  • a pressure-sensitive adhesive layer having excellent various performances such as blister resistance, whitening resistance, adhesive strength and reworkability can be easily formed. Can be formed.
  • the amino group in the amino group-containing monomer (b1) includes, for example, a group represented by -NHR and a group represented by -NR 2 in addition to the group represented by -NH 2.
  • R is, for example, an alkyl group.
  • Examples of the amino group-containing monomer (b1) include N, N-dialkylaminoalkyl (meth) acrylates such as N, N-dimethylaminoethyl (meth) acrylate and N, N-diethylaminoethyl (meth) acrylate. ..
  • the number of carbon atoms of the dialkylaminoalkyl group in the N, N-dialkylaminoalkyl (meth) acrylate is preferably 3 to 20, more preferably 3 to 10.
  • the amount of the amino group-containing monomer (b1) in all the monomer components used to obtain the copolymer (B) is 1 to 10% by mass, preferably 3 to 10% by mass, and more preferably 5 to 10% by mass. %. Further, the copolymer (B) has a structural unit derived from the amino group-containing monomer (b1), preferably 1 to 10% by mass, more preferably 3 to 10% by mass, and further preferably 5 to 10% by mass. ..
  • Copolymerization by adding a copolymer (B) having a high (0 ° C. or higher) glass transition temperature, which is obtained by copolymerizing an amino group-containing monomer (b1) in the above amount, to the copolymer (A).
  • the blister resistance can be improved by compensating for the decrease in the cohesive force derived from the structural unit derived from the alkoxyalkyl (meth) acrylate (a1) which is the main component of the coalescence (A).
  • the copolymer (B) preferably further has a structural unit derived from the (meth) acrylic acid ester (b2) (excluding the (meth) acrylic acid ester corresponding to the amino group-containing monomer (b1)). ..
  • Examples of the (meth) acrylic acid ester (b2) include alkyl (meth) acrylates, alicyclic hydrocarbon groups or aromatic hydrocarbon group-containing (meth) acrylates, and alkoxypolyalkylene glycol mono (meth) acrylates. .. Specific examples of these include the monomers described in the ⁇ Other Monomers >> column of the (meth) acrylic copolymer (A).
  • the amount of (meth) acrylic acid ester (b2) in all the monomer components used to obtain the copolymer (B) is preferably 50 to 99% by mass, more preferably 60 to 97% by mass, still more preferably. Is 70 to 95% by mass. Further, the copolymer (B) contains a structural unit derived from the (meth) acrylic acid ester (b2), preferably 50 to 99% by mass, more preferably 60 to 97% by mass, and further preferably 70 to 95% by mass. Have%.
  • the copolymer (B) may further have a structural unit derived from a monomer other than the amino group-containing monomer (b1) and the (meth) acrylic acid ester (b2) described above.
  • Examples of other monomers include styrene-based monomers, amide group-containing monomers, nitrogen-based heterocyclic ring-containing monomers, cyano group-containing monomers, and vinyl acetate. However, the monomer corresponding to the (meth) acrylic acid ester (b2) is excluded.
  • the weight average molecular weight (Mw) of the copolymer (B) measured by the GPC method is usually 10,000 to 50,000, preferably 10,000 to 40,000, more preferably 15,000 to 30, It is 000.
  • Mw weight average molecular weight
  • the copolymer (B) is less likely to be unevenly distributed in the pressure-sensitive adhesive layer, and a good compatible state tends to be obtained.
  • the molecular weight distribution (Mw / Mn) of the copolymer (B) is usually 2 to 15, preferably 2.5 to 10, and more preferably 3 to 8. In such an embodiment, a good compatibility state tends to be obtained. Mw and Mw / Mn can be measured, for example, by the method described in Examples.
  • the glass transition temperature (Tg) of the copolymer (B) is 0 ° C. or higher, preferably 50 to 200 ° C., and more preferably 80 to 150 ° C. In such an embodiment, there is a tendency to obtain a pressure-sensitive adhesive composition having excellent blister resistance and adhesive strength.
  • the glass transition temperature can be calculated by the so-called Fox formula.
  • the copolymer (B) one kind or two or more kinds can be used.
  • the content of the copolymer (B) is 2 to 19 parts by mass, preferably 3 to 19 parts by mass with respect to 100 parts by mass of the copolymer (A). It is 17 parts by mass, more preferably 3 to 15 parts by mass.
  • the content of the copolymer (B) is at least the above lower limit value, a pressure-sensitive adhesive layer having excellent blister resistance tends to be obtained, and when the content of the copolymer (B) is at least the above upper limit value. , There is a tendency to obtain an adhesive layer having excellent adhesive strength.
  • the copolymer (B) can be produced by a known method, and is preferably produced by solution polymerization.
  • specific production conditions for example, the production conditions described in the copolymer (A) column can be referred to.
  • the cross-linking agent (C) is not particularly limited as long as it is a component capable of causing a cross-linking reaction with the copolymer (A).
  • an epoxy-based cross-linking agent (C1), a metal chelate-based cross-linking agent (C2), and an isocyanate-based cross-linking agent (C3) can be mentioned.
  • the cross-linking agent (C) one kind or two or more kinds can be used.
  • the content of the cross-linking agent (C) is preferably 0.01 to 5% by mass with respect to 100 parts by mass of the (meth) acrylic copolymer (A). Parts, more preferably 0.01 to 3 parts by mass, still more preferably 0.01 to 1 part by mass.
  • Epoxy cross-linking agent (C1) examples include epoxy compounds having two or more epoxy groups in one molecule, and specific examples thereof include ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, and glycerin diglycidyl ether.
  • Glycerin triglycidyl ether 1,3-bis (N, N-diglycidylaminomethyl) cyclohexane, N, N, N', N'-tetraglycidyl-m-xylylene diamine, N, N, N', N' -Tetraglycidyl aminophenyl methane, triglycidyl isocyanurate, mn, N-diglycidyl aminophenyl glycidyl ether, N, N-diglycidyl toluidine, N, N-diglycidyl aniline.
  • the number of epoxy groups in one molecule of the epoxy compound is, for example, 2 to 10.
  • the epoxy-based cross-linking agent (C1) one type or two or more types can be used.
  • Metal chelate cross-linking agent (C2) examples include polyvalent metals such as aluminum, iron, copper, zinc, tin, titanium, nickel, antimony, magnesium, vanadium, chromium, and zirconium, as well as alkoxide, acetylacetone, and ethyl acetoacetate. Examples thereof include compounds in which such components are coordinated. Among these, an aluminum chelate compound is preferable.
  • metal chelate-based cross-linking agent (C2) one kind or two or more kinds can be used.
  • Isocyanate-based cross-linking agent (C3) Examples of the isocyanate-based cross-linking agent (C3) include isocyanate compounds having two or more isocyanate groups in one molecule.
  • Examples of the diisocyanate compound having 2 isocyanate groups in one molecule include aliphatic diisocyanates, alicyclic diisocyanates, and aromatic diisocyanates.
  • Examples of the isocyanate compound having 3 or more isocyanate groups in one molecule include aromatic polyisocyanates, aliphatic polyisocyanates, and alicyclic polyisocyanates.
  • Examples of the isocyanate compound include multimers (for example, dimer or trimer, biuret, isocyanurate) and derivatives (for example, polyhydric alcohol) of the isocyanate compound having 2 or 3 or more isocyanate groups. Addition reaction products with two or more molecules of diisocyanate compounds) and polymers.
  • As the isocyanate-based cross-linking agent (C3) one type or two or more types can be used.
  • the pressure-sensitive adhesive composition according to one embodiment of the present invention includes, for example, an antistatic agent, a silane coupling agent, an ultraviolet absorber, an antioxidant, and a pressure-sensitive adhesive, as long as the effects of the present invention are not impaired. It may contain at least one selected from resins, plasticizers, defoamers, fillers, stabilizers, softeners, and wettability modifiers.
  • the pressure-sensitive adhesive composition according to one embodiment of the present invention preferably contains an organic solvent.
  • the organic solvent include aromatic hydrocarbons such as benzene, toluene and xylene; aliphatic hydrocarbons such as n-pentane, n-hexane, n-heptane and n-octane; cyclopentane, cyclohexane, cycloheptane and cyclo.
  • Alicyclic hydrocarbons such as octane; ethers such as diethyl ether, diisopropyl ether, 1,2-dimethoxyethane, dibutyl ether, tetrahydrofuran, dioxane, anisole, phenylethyl ether, diphenyl ether; chloroform, carbon tetrachloride, 1,2- Halogenized hydrocarbons such as dichloroethane and chlorobenzene; esters such as ethyl acetate, propyl acetate, butyl acetate and methyl propionate; ketones such as acetone, methyl ethyl ketone, diethyl ketone, methyl isobutyl ketone and cyclohexanone; N, N-dimethylformamide, N , N-dimethylacetamide, amides such as N-methylpyrrolidone; nitriles such as acetonitrile and
  • the content ratio of the organic solvent is usually 0 to 90% by mass, preferably 10 to 80% by mass.
  • the pressure-sensitive adhesive sheet according to an embodiment of the present invention has a pressure-sensitive adhesive layer obtained from the above-mentioned pressure-sensitive adhesive composition.
  • the pressure-sensitive adhesive layer can be obtained by cross-linking the above-mentioned pressure-sensitive adhesive composition, specifically, by cross-linking at least the (meth) acrylic copolymer (A) with the cross-linking agent (C).
  • the pressure-sensitive adhesive sheet for example, one of a double-sided pressure-sensitive adhesive sheet having only the pressure-sensitive adhesive layer, a base material, and a double-sided pressure-sensitive adhesive sheet having the pressure-sensitive adhesive layers formed on both sides of the base material, the base material, and the base material.
  • Examples thereof include a single-sided pressure-sensitive adhesive sheet having the pressure-sensitive adhesive layer formed on a surface, and a pressure-sensitive adhesive sheet in which a peel-treated separator is attached to a surface of these pressure-sensitive adhesive sheets that is not in contact with another layer.
  • the conditions for forming the pressure-sensitive adhesive layer are as follows, for example.
  • the composition is applied onto a separator or substrate and dried at usually 60 to 120 ° C., preferably 70 to 110 ° C., usually 1 to 10 minutes, preferably 2 to 5 minutes to form a coating film.
  • the base material or the separator is attached to the coating film on the side without the separator, and when applied on the base material, the separator is attached onto the coating film.
  • it is usually cured for 1 day or more, preferably for 2 to 10 days, usually in an environment of 5 to 60 ° C., preferably 15 to 50 ° C., usually 30 to 70% RH, preferably 40 to 70% RH. (Aging).
  • a cross-linked product (network polymer) can be efficiently formed.
  • one of the separators may be peeled off after aging and the base material may be attached to the exposed pressure-sensitive adhesive layer.
  • the base material and the separator include plastic films such as polyester (eg, polyethylene terephthalate), polyethylene, polypropylene, and ethylene-vinyl acetate copolymer; non-woven fabric; and paper separators.
  • plastic films such as polyester (eg, polyethylene terephthalate), polyethylene, polypropylene, and ethylene-vinyl acetate copolymer; non-woven fabric; and paper separators.
  • the surfaces of the base material and the separator may be peeled off.
  • the thickness of the pressure-sensitive adhesive layer is usually 3 to 1000 ⁇ m, preferably 5 to 500 ⁇ m.
  • the thickness of the base material and the separator is usually 10 to 1000 ⁇ m.
  • Examples of the method for applying the pressure-sensitive adhesive composition include a known method, for example, a spin coating method, a knife coating method, a roll coating method, a bar coating method, a blade coating method, a die coating method, and a gravure coating method.
  • the pressure-sensitive adhesive layer can be formed by applying and drying in such a manner.
  • the pressure-sensitive adhesive sheet according to the embodiment of the present invention has a pressure-sensitive adhesive layer having high moisture and heat resistance as described above.
  • the pressure-sensitive adhesive layer exhibits excellent blister resistance and whitening resistance.
  • the adhesive sheet according to the embodiment of the present invention has excellent reworkability and high adhesive strength after a lapse of a certain period of time after being attached to the adherend.
  • the adhesive sheet according to the embodiment of the present invention can be used as an industrial adhesive sheet or for laminating various resin films, and is particularly contained in a product placed in a high temperature and high humidity environment. It is preferably used to form a pressure-sensitive adhesive layer.
  • Examples of the adherend of the pressure-sensitive adhesive sheet according to the embodiment of the present invention include a transparent resin film such as polycarbonate (PC), polyethylene terephthalate (PET), and polymethylmethacrylate (PMMA); and a transparent plate such as glass. ..
  • a transparent resin film such as polycarbonate (PC), polyethylene terephthalate (PET), and polymethylmethacrylate (PMMA)
  • a transparent plate such as glass. ..
  • the optical member according to the embodiment of the present invention has a pressure-sensitive adhesive layer obtained from the above-mentioned pressure-sensitive adhesive composition.
  • the optical member include optical films such as a polarizing film, a retardation film, an elliptical polarizing film, an antireflection film, a brightness improving film, a light diffusing film, and a hard coat film, and having the pressure-sensitive adhesive layer. Be done.
  • the pressure-sensitive adhesive sheet according to the embodiment of the present invention can be attached to various members, and is particularly suitable for attaching a touch panel member for attaching different types of members.
  • the touch panel is mounted on, for example, a smartphone, a tablet computer, and an in-vehicle device such as a car navigation device.
  • the touch panel includes a touch panel unit, which is transparent, for example, composed of a transparent member, a pressure-sensitive adhesive layer obtained from the pressure-sensitive adhesive composition according to an embodiment of the present invention, and a metal or a metal oxide. It has a conductive film, or a transparent conductive film made of a metal with a support or a metal oxide with a support.
  • the transparent member examples include a transparent resin film such as polycarbonate (PC), polyethylene terephthalate (PET), and polymethylmethacrylate (PMMA); and a transparent plate such as glass.
  • a transparent resin film such as polycarbonate (PC), polyethylene terephthalate (PET), and polymethylmethacrylate (PMMA)
  • metals and metal oxides include indium tin oxide (ITO), antimonthine oxide (ATO), and tin oxide.
  • Examples of the touch panel unit include a resistive touch panel unit and a capacitance type touch panel unit. These are laminates of various materials, and the bonding of the various materials relates to an embodiment of the present invention.
  • a pressure-sensitive adhesive composition can be used. Applications of the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition include, for example, a pressure-sensitive adhesive layer for bonding transparent members to each other, a pressure-sensitive adhesive layer for bonding a transparent member and a transparent conductive film, and a touch panel. An adhesive layer for bonding the unit and the polarizing plate can be mentioned.
  • the adhesive layer used is required to have high transparency, and further, characteristics such as high humidity and heat resistance are required.
  • the pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive composition according to one embodiment of the present invention has high wet heat resistance as described above. Therefore, the pressure-sensitive adhesive layer can be suitably used for the touch panel unit.
  • the glass transition temperature (Tg) of the (meth) acrylic copolymer was calculated from the Fox formula.
  • Weight average molecular weight (Mw) and molecular weight distribution (Mw / Mn) For the (meth) acrylic copolymer, the weight average molecular weight (Mw) and the molecular weight distribution (Mw / Mn) in terms of standard polystyrene were determined by the gel permeation chromatography (GPC) method under the following conditions.
  • -Measuring device HLC-8120GPC (manufactured by Tosoh) -GPC column configuration: The following 5-column column (all manufactured by Tosoh) (1) TSK-GEL HXL-H (guard column) (2) TSK-GEL G7000HXL (3) TSK-GEL GMHXL (4) TSK-GEL GMHXL (5) TSK-GEL G2500HXL ⁇ Dilute with tetrahydrofuran so that the sample concentration is 1.0 mg / cm 3. ⁇ Mobile phase solvent: tetrahydrofuran ⁇ Flow rate: 1.0 cm 3 / min -Column temperature: 40 ° C
  • Polymerization was carried out in the same manner as in Polymerization Example 1 except that the monomer composition was changed as described in Table 1 (the unit of composition is parts by mass), and the (meth) acrylic copolymers (A2) to (A3), (CA1) to (cA3) were obtained.
  • the obtained (meth) acrylic copolymer (B1) had a Mw of 21000 and a Mw / Mn of 4.5.
  • Example 1 The polymer solution of the (meth) acrylic copolymer (A1) obtained in Polymerization Example 1, the polymer solution of the (meth) acrylic copolymer (B1) obtained in Polymerization Example 2, and the epoxy compound ""E-AX" (tetrafunctional epoxy compound; manufactured by Soken Kagaku Co., Ltd., solid content 5%) was added to obtain a pressure-sensitive adhesive composition.
  • the blending amount of each was 100 parts of the (meth) acrylic copolymer (A1), 10 parts of the (meth) acrylic copolymer (B1), and the solid content of the epoxy compound "E-AX" was 0. It is an amount of 045 parts.
  • Examples 2 to 5 Comparative Examples 1 to 12
  • a pressure-sensitive adhesive composition was obtained in the same manner as in Example 1 except that the compounding composition was changed as described in Table 3.
  • the amount of each component is the amount (parts by mass) with respect to 100 parts of the (meth) acrylic copolymer (A) or the comparative copolymer (cA1) to (cA3).
  • PET polyethylene terephthalate
  • PC polycarbonate
  • ⁇ Blister resistance> The adhesive layer of the aged sheet sample was transferred to a PET film having a thickness of 100 ⁇ m, cut into a size of 60 mm ⁇ 50 mm, attached to one side of a polycarbonate plate, and then adjusted to 50 ° C. and 5 atm.
  • a test plate was prepared by holding it in an autoclave for 20 minutes. Then, the test plate was left to stand for 72 hours under the conditions of a temperature of 85 ° C. and a humidity of 85% RH, and the generation of floats (blisters) from the foam / substrate was visually confirmed and evaluated according to the following criteria. Criteria AA: No appearance defects such as foaming / floating were observed.
  • BB Poor appearance such as foaming / floating is observed very slightly, but it is within the range where there is no problem in actual use.
  • CC Poor appearance such as foaming / floating was observed.
  • DD Poor appearance such as foaming / floating was observed over a wide area.
  • the adhesive layer of the aged sheet sample was transferred to a PET film having a thickness of 100 ⁇ m, cut into a size of 60 mm ⁇ 50 mm, attached to one side of a polycarbonate plate, and then adjusted to 50 ° C. and 5 atm.
  • a test plate was prepared by holding in an autoclave for 20 minutes, and the initial haze value was measured. Then, the test plate was left to stand for 72 hours under the conditions of a temperature of 85 ° C. and a humidity of 85% RH, and the haze value after moist heat treatment (durability) was measured with a haze meter.
  • BB The haze value after wet heat treatment (durability) was 1.5 or more and less than 2.0.
  • CC The haze value after wet heat treatment (durability) was 2.0 or more.
  • the adhesive layer of the aged sheet sample was transferred to a PET film having a thickness of 100 ⁇ m, cut into a size of 25 mm ⁇ 100 mm, attached to one side of a polycarbonate plate, and pressure-bonded three times with a 2 kg roller. .. After leaving for 20 minutes, the PET film was peeled off at a peeling angle of 180 degrees and a tensile speed of 300 mm / min, and the initial adhesive strength was measured. Criteria AA: The initial adhesive strength was less than 0.5 N / 25 mm. BB: The initial adhesive strength was 0.5 N / 25 mm or more and less than 1.0 N / 25 mm. CC: The initial adhesive strength was 1.0 N / 25 mm or more.
  • ⁇ Adhesive strength> The adhesive layer of the aged sheet sample is transferred to a PET film having a thickness of 100 ⁇ m, cut into a size of 25 mm ⁇ 100 mm, attached to one side of a polycarbonate plate or a glass plate, and then heated to 50 ° C. and 5 atm.
  • the PET film was held in an adjusted autoclave for 20 minutes, left in a room temperature environment for 60 minutes, and then the PET film was peeled off at a peeling angle of 180 degrees and a tensile speed of 300 mm / min, and the adhesive strength was measured.
  • BB The adhesive strength was 10 N / 25 mm or more and less than 20 N / 25 mm.
  • CC Adhesive strength was less than 10 N / 25 mm.
  • ZIPPING Secure-Slip phenomenon
  • Y-75 Isocyanate-based compound (isocyanate-based cross-linking agent; manufactured by Soken Chemical Co., Ltd., isocyanurate of hexamethylene diisocyanate: solid content 75%, ethyl acetate solution)
  • E-AX Epoxy compound (epoxy cross-linking agent; manufactured by Soken Chemical, tetrafunctional epoxy compound: solid content 5%, toluene / isopropyl alcohol solution)
  • the amount of the cross-linking agent in Table 3 is the amount of solid content.
  • Example 1 From the comparison between Example 1 and Comparative Example 3, by using the copolymer (A) containing the structural unit derived from the carboxy group or acid anhydride group-containing monomer (a2), the structural unit derived from the hydroxyl group-containing monomer can be obtained. It can be seen that the reworkability and adhesive strength are improved with respect to the copolymer containing the copolymer.
  • Example 1 From the comparison of Example 1 and Comparative Examples 4 to 6, the copolymer (B) containing a specific amount of the structural unit derived from the amino group-containing monomer (b1) and the copolymer (A) are used in combination to withstand resistance. It can be seen that the blister property and the whitening resistance are improved.
  • Example 1 From the comparison between Example 1 and Comparative Example 7, the blister resistance and adhesive strength can be improved by using the copolymer (B) having a glass transition temperature of 0 ° C. or higher and the copolymer (A) in combination. Understand. From the comparison between Examples 4 to 5 and Comparative Examples 8 to 10, it can be seen that the blister resistance and the adhesive strength are improved by using a specific amount of the copolymer (B) with respect to the copolymer (A).

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WO2023085083A1 (ja) * 2021-11-15 2023-05-19 日東電工株式会社 光学積層体、画像表示パネル及び画像表示装置
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