WO2019123799A1 - Feuille adhésive avec film de démoulage et procédé de fabrication associé - Google Patents

Feuille adhésive avec film de démoulage et procédé de fabrication associé Download PDF

Info

Publication number
WO2019123799A1
WO2019123799A1 PCT/JP2018/038375 JP2018038375W WO2019123799A1 WO 2019123799 A1 WO2019123799 A1 WO 2019123799A1 JP 2018038375 W JP2018038375 W JP 2018038375W WO 2019123799 A1 WO2019123799 A1 WO 2019123799A1
Authority
WO
WIPO (PCT)
Prior art keywords
sensitive adhesive
pressure
adhesive sheet
release film
release
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2018/038375
Other languages
English (en)
Japanese (ja)
Inventor
真理 松本
普史 形見
数馬 三井
崇弘 野中
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nitto Denko Corp
Original Assignee
Nitto Denko Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nitto Denko Corp filed Critical Nitto Denko Corp
Priority to CN201880076662.3A priority Critical patent/CN111465668B/zh
Priority to KR1020207020636A priority patent/KR102567694B1/ko
Priority to SG11202005787TA priority patent/SG11202005787TA/en
Publication of WO2019123799A1 publication Critical patent/WO2019123799A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • 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]
    • C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C09J7/385—Acrylic polymers
    • 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
    • B32B27/18—Layered products comprising a layer of synthetic resin characterised by the use of special additives
    • 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
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3477—Six-membered rings
    • C08K5/3492—Triazines
    • 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
    • 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
    • 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
    • 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
    • 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]
    • 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
    • C09J7/40—Adhesives in the form of films or foils characterised by release liners
    • 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
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
    • C09J2301/312—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier parameters being the characterizing feature
    • 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
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
    • C09J2301/416—Additional features of adhesives in the form of films or foils characterized by the presence of essential components use of irradiation

Definitions

  • the present invention relates to a pressure-sensitive adhesive sheet to which a release film has been temporarily attached and a method for producing the same.
  • a transparent adhesive sheet is used to bond optical members in a display device such as a liquid crystal display or an organic EL display or a display input device such as a touch panel.
  • the transparent adhesive sheet is generally provided as an adhesive sheet with a release film having release films attached on both sides.
  • one of the release films (light release film) is peeled off to expose one surface of the pressure-sensitive adhesive sheet, and bonding with the first adherend is performed. (Heavy release film) is peeled off, and the second adherend is attached to the other side of the pressure-sensitive adhesive sheet.
  • the optical member used for a display device, an input device, etc. may be required to have an ultraviolet ray cut property from the viewpoint of suppression of deterioration of the element due to ultraviolet rays and the like.
  • the optical member disposed on the front of the element is required to have high ultraviolet light cutting properties.
  • a polarizing plate used in a liquid crystal display or an organic EL display is required to have an ultraviolet blocking property to an optical member disposed in front of the polarizer in order to prevent deterioration of the polarizer due to ultraviolet rays (for example, fading of iodine). Be done.
  • Patent Document 1 a pressure-sensitive adhesive composition obtained by adding a UV absorber to a heat-curable acrylic pressure-sensitive adhesive solution is applied in the form of a film, and then dried by heating to obtain a pressure-sensitive adhesive sheet having UV cutability. Is described.
  • Patent Document 2 a photocurable acrylic pressure-sensitive adhesive composition containing a photocurable acrylic composition, a photopolymerization initiator and an ultraviolet light absorber is applied in a layer form on a release film substrate, It is described that photo-curing is performed in a state where another release film is superposed and the contact with air is blocked, and a photo-curable pressure-sensitive adhesive sheet having an ultraviolet ray-cutting property is obtained.
  • Patent Document 2 when a photocurable pressure-sensitive adhesive is used, a solvent is not necessary for forming a pressure-sensitive adhesive sheet, and therefore, it is easy to increase the thickness of the pressure-sensitive adhesive sheet. Moreover, it has the advantage that the smoothness of an adhesive sheet can be improved by photocuring in the state which the release sheet contacted on both surfaces of a sheet-like photocurable adhesive composition.
  • the present invention aims at offer of a pressure sensitive adhesive sheet with a release film which has ultraviolet ray cutability and good releasability with a release film.
  • the release film-attached pressure-sensitive adhesive sheet of the present invention comprises a photocurable pressure-sensitive adhesive sheet having a first main surface and a second main surface, and a first release film temporarily attached to the first main surface of the pressure-sensitive adhesive sheet.
  • the first release film comprises a release layer on a film substrate, and the release layer is in contact with the pressure-sensitive adhesive sheet.
  • the adhesive sheet contains a photocurable acrylic polymer and a UV absorber.
  • the release film-attached pressure-sensitive adhesive sheet may have a second release film temporarily attached to the second main surface of the pressure-sensitive adhesive sheet.
  • the first main surface of the pressure-sensitive adhesive sheet is a light irradiation surface when the photocurable pressure-sensitive adhesive composition is photocured. That is, a photocurable adhesive sheet is formed by performing light irradiation to a photocurable adhesive composition via a first release film.
  • a pressure-sensitive adhesive contains an ultraviolet absorber by using a release film provided with a predetermined silicone-based release layer as the first release film provided on the light irradiation side of the photocurable pressure-sensitive adhesive composition
  • the silicone-based release layer of the first release film preferably has a Si atom content of 0.02 to 0.07 g / m 2 .
  • the pressure-sensitive adhesive sheet preferably contains 0.1 to 10 parts by weight of a UV absorber based on 100 parts by weight of the acrylic polymer.
  • a UV absorber a triazine type ultraviolet absorber is used, for example.
  • the acrylic polymer of the pressure-sensitive adhesive sheet may contain a polyfunctional monomer component having two or more polymerizable functional groups in one molecule as a monomer component.
  • the photocurable pressure-sensitive adhesive composition contains an acrylic material, a UV absorber, and a photopolymerization initiator.
  • the acrylic material contained in the photocurable pressure-sensitive adhesive composition includes acrylic monomers and partially polymerized products thereof.
  • the acrylic material may contain both an acrylic monomer and a partially polymerized acrylic monomer.
  • the laminated body in which the photocurable pressure-sensitive adhesive composition layer is sandwiched between the first release film and the second release film is irradiated with light from the first release film side,
  • a pressure-sensitive adhesive sheet in which a release film is temporarily attached to both sides can be obtained.
  • the peeling force between the first release film and the pressure-sensitive adhesive sheet may be larger than the peeling force between the second release film and the pressure-sensitive adhesive sheet.
  • the pressure-sensitive adhesive sheet having a high visible light transmittance and an ultraviolet ray cutting property is suitably used as an optical pressure-sensitive adhesive sheet for a display device or an input device for a display which is required to have an ultraviolet ray cutting property.
  • the release film-attached pressure-sensitive adhesive sheet of the present invention the excessive increase in the peel force between the pressure-sensitive adhesive sheet and the first release film is suppressed, so the release of the release film from the pressure-sensitive adhesive sheet and the pressure-sensitive adhesive sheet and adherend It is excellent in the workability of bonding with.
  • the release film-attached pressure-sensitive adhesive sheet of the present invention comprises a release film temporarily attached to at least one surface of the pressure-sensitive adhesive sheet.
  • the "temporary attachment” means a state of being attached releasably.
  • the release film may be temporarily attached to both surfaces of the pressure-sensitive adhesive sheet.
  • FIG. 1 is a cross-sectional view of a release film-attached pressure-sensitive adhesive sheet 1 in which release films 10 and 20 are temporarily attached to both sides of a pressure-sensitive adhesive sheet 50.
  • the pressure-sensitive adhesive sheet 50 is a sheet in which a pressure-sensitive adhesive is formed.
  • the adhesive sheet 50 is transparent and has a small absorption of visible light. 85% or more is preferable and, as for the total light transmittance of the adhesive sheet 50, 90% or more is more preferable. 2% or less is preferable and, as for the haze of an adhesive sheet, 1% or less is more preferable.
  • the total light transmittance and the haze are measured according to JIS K7136 using a haze meter.
  • the adhesive sheet 50 is an acrylic adhesive containing a photocurable acrylic polymer, and contains an ultraviolet absorber in addition to the acrylic polymer.
  • the acrylic pressure-sensitive adhesive sheet is formed by applying a photocurable pressure-sensitive adhesive composition including an acrylic monomer and / or a partial polymer (prepolymer) of an acrylic polymer, a UV absorber, and a photopolymerization initiator in a layer, and photocuring It consists of a photocurable adhesive obtained by
  • the “photocurable” pressure-sensitive adhesive is a pressure-sensitive adhesive which is photocurable, containing a photopolymerizable functional group-containing compound such as a vinyl group or a (meth) acryloyl group.
  • photocured adhesive is meant an adhesive after photocuring the photocurable adhesive.
  • the pressure-sensitive adhesive after polymerization of the photocurable pressure-sensitive adhesive when a part of the photopolymerizable compound remains unreacted, the pressure-sensitive adhesive is photocured and photocurable ( There is a case of photocurable).
  • the photocurable pressure-sensitive adhesive composition contains a photopolymerizable acrylic material, a UV absorber, and a photopolymerization initiator.
  • Photopolymerizable acrylic material As a photopolymerizable acrylic material contained in a photocurable adhesive composition, an acryl-type monomer and its partial polymer (prepolymer) are mentioned.
  • a (meth) acrylic acid alkyl ester having 1 to 20 carbon atoms in the alkyl group is preferably used.
  • the alkyl group may have a branch.
  • the content of the (meth) acrylic acid alkyl ester is preferably 40% by weight or more, more preferably 50% by weight or more, and still more preferably 60% by weight or more based on the total amount of monomer components of the acrylic material.
  • the monomer component may contain, in addition to the (meth) acrylic acid alkyl ester, a highly polar monomer such as a hydroxy group-containing monomer or a nitrogen-containing monomer. Since the acrylic polymer contains a high polar monomer unit, the cohesion of the pressure sensitive adhesive is improved to enhance the adhesion of the pressure sensitive adhesive sheet to the adherend, and the white turbidity of the pressure sensitive adhesive under high temperature and high humidity environment is suppressed. And the transparency of the pressure-sensitive adhesive sheet tends to be improved.
  • a highly polar monomer such as a hydroxy group-containing monomer or a nitrogen-containing monomer.
  • hydroxy group-containing monomer 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, (meth) Examples thereof include 8-hydroxyoctyl acrylate, 10-hydroxydecyl (meth) acrylate, 12-hydroxylauryl (meth) acrylate and (4-hydroxymethylcyclohexyl) -methyl acrylate.
  • the content of the hydroxy group-containing monomer is preferably 1 to 40% by weight, more preferably 3 to 30% by weight, and still more preferably 5 to 20% by weight, based on the total amount of the monomer components.
  • Nitrogen-containing monomers such as N-vinyl pyrrolidone, methyl vinyl pyrrolidone, vinyl pyridine, vinyl piperidone, vinyl pyrimidine, vinyl piperazine, vinyl pyrazine, vinyl pyrrole, vinyl pyrrole, vinyl imidazole, vinyl oxazole, vinyl morpholine, (meth) acryloyl morpholine, N-vinyl Examples thereof include vinyl-based monomers such as carboxylic acid amides and N-vinylcaprolactam, and cyanoacrylate-based monomers such as acrylonitrile and methacrylonitrile.
  • the nitrogen-containing monomer is preferably one having a cyclic structure containing a nitrogen atom, and among them, a lactam vinyl monomer such as N-vinyl pyrrolidone is preferable.
  • the content of the nitrogen-containing monomer is preferably 0.5 to 50% by weight, more preferably 1 to 40% by weight, and still more preferably 3 to 30% by weight, based on the total amount of the monomer components.
  • the monomer component may contain monomers other than the above, such as a carboxyl group-containing monomer, a cyclic ether group-containing monomer, and a silane monomer.
  • the monomer component may contain a polyfunctional polymerizable compound having two or more polymerizable functional groups in one molecule.
  • the polyfunctional polymerizable compound may be present in the pressure-sensitive adhesive composition as a monomer or an oligomer, and may be bonded to a functional group such as a hydroxy group of the prepolymer component.
  • polyfunctional acrylates are preferable, and trimethylolpropane tri (meth) acrylate, hexanediol di (meth) acrylate, dipentaerythritol hexa (meth) acrylate and the like are suitably used as polyfunctional monomers.
  • the amount of the polyfunctional monomer used varies depending on the molecular weight, the number of functional groups, etc., but is preferably 5% by weight or less, more preferably 3% by weight or less, and still more preferably 2% by weight or less.
  • the amount of the polyfunctional monomer used may be 0.001 parts by weight or more, 0.01 parts by weight or more, or 0.05 parts by weight or more based on the total amount of the monomer components.
  • the above monomer component may be present as a partial polymer (prepolymer).
  • the prepolymer is a partially polymerized monomer component.
  • the prepolymer can be prepared, for example, by partially polymerizing a composition for forming a prepolymer in which a monomer component and a polymerization initiator are mixed.
  • the composition for forming the prepolymer may contain all the monomer components constituting the acrylic polymer, and may contain only a part of the monomers constituting the acrylic polymer.
  • the monomer component which comprises an acryl-type polymer contains a monofunctional monomer and a polyfunctional monomer
  • a polyfunctional monomer is added to the prepolymer composition which partially polymerized only the monofunctional monomer, and an adhesive composition is prepared.
  • the crosslinking point by a polyfunctional monomer can be uniformly introduced into a polymer by adding a polyfunctional monomer to a prepolymer composition in which only a monofunctional monomer is partially polymerized and performing post-polymerization.
  • a part of the polyfunctional monomer component constituting the acrylic polymer may be contained in the prepolymer-forming composition, and after polymerization of the prepolymer, the remainder of the polyfunctional monomer component may be added to carry out post polymerization.
  • the prepolymer may be prepared in two or more stages or three or more stages of polymerization. For example, after pre-polymerizing only a monofunctional monomer, a polyfunctional monomer is added to carry out partial polymerization to prepare a prepolymer composition, and if necessary, a monomer component is further added to carry out post polymerization. Good.
  • the polymerization method of the prepolymer is not particularly limited. From the viewpoint of adjusting the reaction time to bring the molecular weight (polymerization rate) of the prepolymer into a desired range, photopolymerization by irradiation with actinic rays such as ultraviolet rays is preferable. When performing photopolymerization, it is preferable that a prepolymer composition contains a photoinitiator. Specific examples of the photopolymerization initiator will be described later.
  • the composition for forming a prepolymer may contain a chain transfer agent and the like as required, in addition to the monomer component and the polymerization initiator.
  • the chain transfer agent has the function of receiving radicals from the growing polymer chain to stop the elongation of the polymer, and the chain transfer agent having received the radicals attacks the monomer to start polymerization again.
  • thiols such as ⁇ -thioglycerol, lauryl mercaptan, glycidyl mercaptan, mercaptoacetic acid, 2-mercaptoethanol, thioglycolic acid, 2-ethylhexyl thioglycolate, 2,3-dimercapto-1-propanol and the like are preferable.
  • thiols such as ⁇ -thioglycerol, lauryl mercaptan, glycidyl mercaptan, mercaptoacetic acid, 2-mercaptoethanol, thioglycolic acid, 2-ethylhexyl thioglycolate, 2,3-dimercapto-1-propanol and the like are preferable.
  • thiols such as ⁇ -thioglycerol, lauryl mercaptan, glycidyl mercaptan, mercaptoacetic acid, 2-mercaptoethanol,
  • the polymerization rate of the prepolymer is not particularly limited, but it is preferably 3 to 50%, more preferably 5 to 40%, from the viewpoint of achieving a viscosity suitable for coating on a substrate.
  • the polymerization rate of the prepolymer can be adjusted to a desired range by adjusting the type and amount of the photopolymerization initiator, the irradiation intensity and irradiation time of actinic rays such as ultraviolet light.
  • the polymerization rate is calculated by the following formula from the weight before and after heating (drying) when the prepolymer composition is heated at 130 ° C. for 3 hours.
  • a polymerization rate is calculated by using a value obtained by subtracting the amount of the solvent from the total weight of the prepolymer composition as a weight before heating in the following formula.
  • Polymerization rate of polymer (%) 100 ⁇ (weight after heating / weight before heating)
  • a photocurable pressure-sensitive adhesive by mixing the above-described photopolymerizable acrylic material (monomer and / or partial polymer thereof) with the balance of the monomer component, the ultraviolet light absorber, the photopolymerization initiator, and the other additives, etc. A composition is obtained.
  • UV absorber examples include benzotriazole UV absorber, benzophenone UV absorber, triazine UV absorber, salicylate UV absorber, cyanoacrylate UV absorber and the like.
  • a triazine-based ultraviolet absorber is preferable because it has high UV absorption, is excellent in compatibility with an acrylic polymer, and is easy to obtain a highly transparent acrylic pressure-sensitive adhesive sheet.
  • triazine-based ultraviolet ray absorption containing a hydroxyl group Agents are preferred, and hydroxyphenyl triazine based UV absorbers are particularly preferred.
  • the number of hydroxyl groups in the triazine-based ultraviolet absorber is preferably 2 or less.
  • UV absorber You may use a commercial item as a ultraviolet absorber.
  • Commercially available triazine-based UV absorbers include 2- (4,6-bis (2,4-dimethylphenyl) -1,3,5-triazin-2-yl) -5-hydroxyphenyl and [(alkyloxy)].
  • the content of the ultraviolet absorber in the photocurable pressure-sensitive adhesive composition is preferably 0.1 to 10 parts by weight, more preferably 0.3 to 7 parts by weight, per 100 parts by weight of the monomer component. Further preferred is 5 parts by weight.
  • the photocurable pressure-sensitive adhesive composition contains a photopolymerization initiator.
  • the photopolymerization initiator is a photoradical generator that generates radicals by visible light or ultraviolet light having a wavelength shorter than 450 nm.
  • the photocurable pressure-sensitive adhesive composition contains a UV absorber
  • a part of the irradiation light for photocuring is absorbed by the UV absorber.
  • the photopolymerization initiator sensitive to a wavelength range in which the absorption by the ultraviolet light absorber is small.
  • the photopolymerization initiator is preferably one having sensitivity to a longer wavelength than 380 nm, and more preferably one having sensitivity to a longer wavelength than 400 nm.
  • a photopolymerization initiator having an absorption coefficient of 1 ⁇ 10 2 [mLg ⁇ 1 cm ⁇ 1 ] or more at a wavelength of 405 nm It is preferable to use a photopolymerization initiator having an absorption coefficient of 1 ⁇ 10 2 [mLg ⁇ 1 cm ⁇ 1 ] or more at a wavelength of 405 nm.
  • the photopolymerization initiator having long wavelength photosensitivity may have sensitivity to light having a wavelength of 400 nm or less.
  • the photopolymerization initiator having a photosensitivity having a wavelength of 400 nm or more include 2,4,6-trimethyl benzoyl diphenyl phosphine oxide ("Lucirin TPO” manufactured by BASF), 2,4,6-trimethyl benzoyl phenyl ethoxy phos Acyl phosphine oxides such as fin oxide (“Lucirin TPO-L” manufactured by BASF); 2-benzyl-2-dimethylamino-1- (4 monomorpholinophenyl) butanone-1 (“IRGACURE 369” manufactured by BASF) Amino ketones; bis (2,4,6-trimethylbenzoyl) -phenyl phosphine oxide ("IRGACURE 819" manufactured by BASF), 2,2-dimethoxy-1,2-diphenylethane-1-one (“IRGACURE” manufactured by BASF 651 "), bis (2 6-dimethoxybenzoyl) -2,4,4-trimethyl pentyl phosphine
  • Photopolymerization initiators having long-wavelength photosensitivity and non-long-wavelength photosensitivity (for example, having an absorption coefficient at a wavelength of 405 nm of less than 1 ⁇ 10 2 [mLg ⁇ 1 cm ⁇ 1 ] ) May be used in combination.
  • photopolymerization initiators not having long wavelength photosensitivity include benzoin ether photopolymerization initiator, acetophenone photopolymerization initiator, ⁇ -ketol photopolymerization initiator, photoactive oxime photopolymerization initiator, benzoin photopolymerization initiator Photopolymerization initiator, benzyl photopolymerization initiator, benzophenone photopolymerization initiator, ketal photopolymerization initiator, thioxanthone photopolymerization initiator, acylphosphine oxide photopolymerization initiator, titanocene photopolymerization initiator Etc.
  • the content of the photopolymerization initiator in the photocurable pressure-sensitive adhesive composition is preferably 0.02 to 10 parts by weight with respect to a total of 100 parts by weight of the monomer component and the prepolymer component constituting the acrylic polymer, and 0 More preferably, .05-5 parts by weight. If the amount of the photopolymerization initiator is too small, the polymerization rate may be insufficient. If the amount of the photopolymerization initiator is too large, the molecular weight of the polymer may be low and the adhesive strength of the adhesive may be insufficient.
  • a photoinitiator can be used also in preparation (partial polymerization) of prepolymer.
  • the photopolymerization initiator used for partial polymerization may be the same as or different from the photopolymerization initiator added to the photocurable pressure-sensitive adhesive composition.
  • the photopolymerization initiator used for the partial polymerization may not have the photosensitivity of long wavelength.
  • the unreacted material of the photopolymerization initiator used for partial polymerization may be used as it is as a photopolymerization initiator in the photopolymerizable pressure-sensitive adhesive composition.
  • an ultraviolet absorber to the prepolymer composition after partial polymerization without including the ultraviolet absorber in the composition for forming a prepolymer.
  • partial polymerization is carried out using a photopolymerization initiator which does not have long wavelength photosensitivity as a pre-added polymerization initiator, and the composition after partial polymerization has a long wavelength as an ultraviolet light absorber and a post-added polymerization initiator
  • post polymerization after adding a photopolymerization initiator having photosensitivity to prepare a photocurable pressure-sensitive adhesive composition and applying the photocurable pressure-sensitive adhesive composition in a layer on a substrate.
  • the photocurable pressure-sensitive adhesive composition may contain a chain transfer agent.
  • the chain transfer agent contained in the photocurable pressure-sensitive adhesive composition is not particularly limited, and, for example, the above-mentioned chain transfer agent can be used.
  • the pressure-sensitive adhesive composition may contain a silane coupling agent, a crosslinking agent, a tackifier, a plasticizer, a softener, and the like for the purpose of adjusting the adhesive strength and the like.
  • the pressure-sensitive adhesive composition may contain additives such as an anti-deterioration agent, a filler, a colorant, an antioxidant, a surfactant, an antistatic agent, and the like in the range not to impair the characteristics of the pressure-sensitive adhesive.
  • the photocurable pressure-sensitive adhesive composition preferably has a viscosity (for example, about 5 to 100 poise) suitable for application onto a substrate.
  • the viscosity of the pressure-sensitive adhesive composition can be adjusted, for example, by the addition of various polymers such as a thickening additive, a polyfunctional monomer, and the like, the polymerization rate of the prepolymer, and the like.
  • the content of the acrylic monomer component is preferably 50% by weight or more, and more preferably 70% by weight or more. Preferably, it is 80% by weight or more.
  • An adhesive sheet is obtained by apply
  • the pressure-sensitive adhesive composition may be applied to a substrate by roll coating, kiss roll coating, gravure coating, reverse coating, roll brushing, spray coating, dip roll coating, bar coating, knife coating, air knife coating, curtain coating , Lip coat, die coat. Since photoradical polymerization is inhibited by oxygen in the air, it is preferable to provide a cover sheet on the coating layer of the photocurable pressure-sensitive adhesive composition to block oxygen.
  • the pressure-sensitive adhesive composition may be applied such that the photocurable pressure-sensitive adhesive composition is sandwiched between two sheets (support base and cover sheet).
  • the coating thickness of the photocurable pressure-sensitive adhesive composition (the thickness of the pressure-sensitive adhesive sheet 50) is not particularly limited, and is, for example, about 10 to 500 ⁇ m. From the viewpoint of enhancing the ultraviolet ray absorptivity of the pressure-sensitive adhesive sheet, the thickness of the pressure-sensitive adhesive sheet is preferably 50 ⁇ m or more, more preferably 100 ⁇ m or more, and still more preferably 150 ⁇ m or more. 10% or less is preferable, as for the light transmittance in wavelength 380 nm of the adhesive sheet 50, 5% or less is more preferable, and 3% or less is more preferable.
  • An adhesive sheet is obtained by irradiating an ultraviolet-ray and / or the visible light of a short wavelength, and photocuring the laminated body provided with a photocurable acrylic adhesive composition layer on a support base material.
  • the photocurable pressure-sensitive adhesive composition layer is photocured by light irradiation on a laminate sandwiched between a support base and a cover sheet, light is irradiated from either the support base side or the cover sheet side The light may be irradiated from both sides.
  • a release film 10 provided with a predetermined release layer 15 is used as a supporting substrate or a cover sheet provided on the light irradiation side of the pressure-sensitive adhesive sheet.
  • the light irradiation intensity is preferably 5 mW / cm 2 or more.
  • the light irradiation intensity is preferably 20 mW / cm 2 or less from the viewpoint of sufficiently increasing the molecular weight of the acrylic polymer after photocuring and securing the holding power at high temperature.
  • the integrated light quantity of the irradiation light is preferably about 100 to 5000 mJ / cm 2 .
  • the light source for light irradiation is not particularly limited as long as the photopolymerization initiator contained in the pressure-sensitive adhesive composition can emit light in the wavelength range having sensitivity, and an LED light source, a high pressure mercury lamp, an ultrahigh pressure mercury A lamp, a metal halide lamp, a xenon lamp or the like is preferably used.
  • the ultraviolet light irradiated to the photocurable adhesive composition containing the ultraviolet absorber is absorbed by the ultraviolet absorber. It is preferable to irradiate light in a wavelength range in which light absorption by the ultraviolet light absorber is small, from the viewpoint of suppression of molecular weight reduction due to temperature rise and improvement of utilization efficiency and curing speed of irradiation light. It is preferable to use an LED light source because it emits less heat from the light source and can emit light with a smaller wavelength width. When an LED light source is used, the emission peak wavelength is preferably 350 nm or more, more preferably 380 nm or more, and still more preferably 400 nm or more.
  • the gel fraction of the pressure-sensitive adhesive sheet is preferably 50% or more, more preferably 75% or more, and still more preferably 85% or more.
  • release film The support substrate for applying the pressure-sensitive adhesive composition, and the cover sheet attached to the surface of the application layer of the pressure-sensitive adhesive composition, a release film having a release layer on the contact surface with the application layer (pressure-sensitive adhesive sheet) Is preferably used.
  • the photocuring is performed in a state where the release film (first release film) 11 provided with the predetermined silicone-based release layer 15 is attached to the light irradiation side of the photocurable pressure-sensitive adhesive composition layer 55. To be done.
  • Resin materials include polyester resins such as polyethylene terephthalate and polyethylene naphthalate, acetate resins, polyether sulfone resins, polycarbonate resins, polyamide resins, polyimide resins, polyolefin resins, (meth) acrylic resins, Polyvinyl chloride resin, polyvinylidene chloride resin, polystyrene resin, polyvinyl alcohol resin, polyarylate resin, polyphenylene sulfide resin and the like can be mentioned. Among these, polyester resins such as polyethylene terephthalate are particularly preferable.
  • the thickness of the substrates 11 and 21 is preferably 10 to 200 ⁇ m, and more preferably 25 to 150 ⁇ m.
  • the release layer examples include silicone-based release agents, fluorine-based release agents, long-chain alkyl-based release agents, fatty acid amide-based release agents, silica powder and the like. Since the adhesion to the acrylic pressure-sensitive adhesive sheet and the releasability can be compatible, the release film 20 is provided with a silicone-based release layer 25 formed of a silicone-based release agent on the surface of the film substrate 21. Is preferably used.
  • the release film 10 attached to the light irradiation surface side of the photocurable pressure-sensitive adhesive composition layer 55 includes a silicone-based release layer 15.
  • the silicone-based release layer 15 has a Si atom content per unit area of 0.02 to 0.07 g / m 2 .
  • Si atom content of the silicone-based release layer 15 is preferably 0.025 ⁇ 0.06g / m 2, more preferably 0.03 ⁇ 0.055g / m 2.
  • the silicone-based release layer 15 of the release film 10 contains a curable silicone resin.
  • the silicone-based resin may be of a type having itself as a main component, or may be a silicone-modified resin in which a reactive silicone is introduced to an organic resin such as a urethane resin, an epoxy resin or an alkyd resin by graft polymerization.
  • the silicone resin various curing reaction types such as addition type, condensation type, ultraviolet curing type, electron beam curing type, and non-solvent type can be used. In particular, it is of a type that forms a peelable film by curing due to an addition reaction due to heat since it is excellent in adhesion to a film substrate and can be compatible with appropriate adhesion to an acrylic pressure-sensitive adhesive sheet and releasability.
  • a silicone resin is preferably used.
  • silicone-based materials that cure by addition reaction include polyorganosiloxanes having a vinyl group or an alkenyl group in the molecule.
  • alkenyl group examples include 3-butenyl group, 4-pentenyl group, 5-hexenyl group, 6-heptenyl group, 7-octenyl group, 8-nonenyl group, 9-decenyl group, 10-undecenyl group, 11-dodecenyl group And the like.
  • polyalkyl alkyl siloxanes such as polydimethylsiloxane, polydiethylsiloxane, polymethylethylsiloxane, etc .
  • polyalkylaryl siloxanes plural kinds of Si atom-containing monomer components such as poly (dimethylsiloxane-diethylsiloxane) are used Copolymers, etc.
  • polydimethylsiloxane is preferred.
  • a commercially available composition containing a curable silicone resin may be used as the silicone resin.
  • Commercially available curable silicone-based mold release agents include Shin-Etsu Chemical KS-774, KS-775, KS-778, KS-779H, KS-847H, KS-856, X-62-2422, and X -62-2461; Toshiba Silicone YSR-3022, TPR-6700, TPR-6720, and TPR-6721; Toray Dow Corning LTC300B, LTC303E, LTC310, LTC310, LTC314, SRX357, BY24-749, SD7333, BY24 -179, BY24-840, BY24-842, BY24-850, SP7015, SP7259, SD7220, SD7226, and SD7229; Dow Corning Asia Ltd. DKQ3-202, DKQ3-203, DKQ3-204, DKQ3-205 DKQ3-210, and the like.
  • the curable silicone-based release agent composition may contain an additive (release control agent) for the purpose of adjusting the release property of the release layer.
  • the addition type silicone-based release agent composition may contain a curing catalyst.
  • a curing catalyst a platinum-based catalyst is preferable.
  • platinum catalysts include chloroplatinic acid, olefin complexes of platinum, and olefin complexes of chloroplatinic acid.
  • the amount of the platinum-based catalyst used is about 10 to 1000 ppm in terms of platinum based on the total solid content of the silicone-based release agent composition.
  • the silicone-based release agent composition may contain an organic solvent.
  • Organic solvents include hydrocarbon solvents such as cyclohexane, n-hexane and n-heptane; aromatic solvents such as toluene and xylene; ester solvents such as ethyl acetate and methyl acetate; ketone solvents such as acetone and methyl ethyl ketone And alcohol solvents such as methanol, ethanol and butanol.
  • the organic solvent may be a mixed solvent.
  • the amount of the organic solvent used is preferably about 80 to 99.9% by mass in the silicone-based release agent composition.
  • the silicone-based release agent composition may contain, if necessary, various additives such as a filler, an antistatic agent, an antioxidant, a plasticizer, and a colorant.
  • a silicone-based release layer is formed by applying a silicone-based release agent composition onto the substrate 11 and drying by heating.
  • the coating method include roll coating, kiss roll coating, gravure coating, reverse coating, roll brushing, spray coating, dip roll coating, bar coating, knife coating, air knife coating, curtain coating, lip coating and die coating.
  • the heat drying method includes hot air drying. The conditions for hot air drying vary depending on the heat resistance of the base material, but are usually about 80 to 150 ° C. and about 10 seconds to 10 minutes. If necessary, heat treatment and active energy ray irradiation such as ultraviolet ray irradiation may be used in combination for the purpose of promoting addition reaction of silicone and the like.
  • the application amount of the silicone-based release agent composition may be adjusted so that the amount of silicone resin is about 0.03 to 1 g / m 2 .
  • the thickness of the silicone-based release layer 15 is, for example, 10 to 500 nm.
  • the application amount of the silicone-based release agent composition and the thickness of the silicone-based release layer 15 may be adjusted so that the Si atom content of the silicone-based release layer 15 falls within the above-mentioned range.
  • release film-attached pressure-sensitive adhesive sheet in which release films are temporarily attached to both sides of the pressure-sensitive adhesive sheet, generally, the release force between the pressure-sensitive adhesive sheet and one release film is compared to the release force between the adhesive sheet and the other release film. Relatively small.
  • a release film (light release film) having a low peel strength is peeled off from the pressure-sensitive adhesive sheet and pasted to the first adherend, and then a release film having a relatively large peel strength (Heavy exfoliation film) is exfoliated and pasted to the second adherend.
  • the light release film can be selectively peeled off at the time of bonding with the first adherend, so the work of bonding Can be enhanced.
  • the adhesive force of the pressure-sensitive adhesive is different before and after photocuring, so in consideration of the adhesive properties of the photocurable adhesive sheet, light-peelable film and heavy-peelable film Adhesiveness (peelability) is adjusted.
  • the pressure-sensitive adhesive composition does not contain an ultraviolet light absorber
  • the magnitude relationship between the peel strengths of one release film and the other release film does not change before and after photocuring.
  • the photocurable pressure-sensitive adhesive composition contains an ultraviolet light absorber
  • the increase in the peel strength of the first release film on the light-irradiated surface side is disposed on the opposite surface. There is a tendency to become significantly larger than the increase in the peel force of the two release films.
  • the first release film 10 on the light irradiation surface as a heavy release film and the second release film 20 on the opposite surface as a light release film. That is, it is preferable that the peeling force between the first release film 10 and the adhesive sheet 50 be larger than the peeling force between the second release film 20 and the adhesive sheet 50.
  • the peel force between the pressure-sensitive adhesive sheet 50 after curing and the first release film 10 is preferably 0.1 to 1.1 N / 50 mm, more preferably 0.2 to 0.8 N / 50 mm, 0.3 to 0. .7 N / 50 mm is more preferred.
  • the peeling force of the release film and the pressure-sensitive adhesive sheet is a value measured by a 180 ° peel test at a tensile speed of 0.3 m / min.
  • an excessive increase in the peeling force between the pressure-sensitive adhesive sheet after photocuring and the first release film can be suppressed.
  • the photocurable pressure-sensitive adhesive composition contains a UV absorber
  • the reason why the peel strength of the first release film is increased, and the Si content of the release layer is adjusted to photocure the pressure-sensitive adhesive composition is not clear, but it is presumed that the reaction between the unreacted heat-reactive functional group in the release layer and the compound in the adhesive composition is involved. Ru.
  • the ultraviolet absorber absorbs light, the light energy is converted to heat energy and the temperature rises. In particular, in the vicinity of the interface between the release layer 15 on the light irradiation side and the pressure-sensitive adhesive composition layer 55, the amount of light absorbed by the ultraviolet absorber is large, so the temperature tends to rise.
  • the heat curing reaction tends to proceed. Therefore, the unreacted thermally reactive functional group (vinyl group, alkenyl group, alkoxysilyl group, silanol group, hydrosilyl group, etc.) in the release layer 15 and the compound in the pressure-sensitive adhesive composition in the pressure-sensitive adhesive composition It is considered that the reaction (adhesion force) will increase.
  • the amount of unreacted thermally reactive functional groups in the release layer 15 is reduced. Therefore, in the present invention, the amount of the remaining reactive functional group in the releasing layer 15 capable of reacting with the compound in the pressure-sensitive adhesive composition layer 15 is small, and the adhesive sheet 50 after photocuring and the releasing film 10 It is believed that excessive rise in peel force can be suppressed.
  • the light irradiation to the pressure-sensitive adhesive composition may be performed from any side of the supporting substrate side and the cover sheet side, and the light irradiation may be performed from both sides.
  • the release film 10 provided with the above-mentioned silicone-based release layer 15 may be used as a support substrate on which the pressure-sensitive adhesive composition is applied.
  • the release film 10 provided with the above-mentioned silicone-based release layer 15 may be used as a cover sheet attached on the pressure-sensitive adhesive composition layer 55.
  • the above-described release film may be used as either the support substrate or the cover sheet.
  • the above release film may be used for both the support substrate or the cover sheet.
  • the above-described release film is formed on the surface to which light is first irradiated. It is preferable to use
  • the above-mentioned photo-curable pressure-sensitive adhesive sheet has a high visible light transmittance and has an ultraviolet ray-cutting property, and therefore, is suitably used as an optical pressure-sensitive adhesive for display devices and display input devices which are required to have ultraviolet ray cutting properties.
  • the display device include a liquid crystal display device, an organic EL (electroluminescence) display device, a PDP (plasma display panel), an electronic paper, and the like.
  • a touch panel is mentioned as an input device.
  • the above-mentioned photocurable pressure-sensitive adhesive sheet can also be used for bonding a display device and an input device, bonding with a transparent plate disposed on the surface of a display device or an input device, and the like.
  • the release film-attached pressure-sensitive adhesive sheet having release films temporarily attached on both sides
  • the light release film (second release film 20) is removed to expose the second main surface of the pressure-sensitive adhesive sheet 50, Bond with one adherend.
  • the heavy release film (first release film 10) is released to expose the first main surface of the pressure-sensitive adhesive sheet 50, and bonding with the second adherend is performed. After peeling the release film on both sides, bonding with an adherend may be performed.
  • the pressure-sensitive adhesive sheet has photocurability
  • the pressure-sensitive adhesive sheet after bonding to the adherend may be further irradiated with light.
  • the adhesion reliability with the adherend may be able to be improved by further photocuring the pressure-sensitive adhesive sheet after the lamination with the adherend.
  • ⁇ Adhesive Composition A> In a monomer mixture composed of 78 parts by weight of 2-ethylhexyl acrylate (2EHA), 18 parts by weight of N-vinyl-2-pyrrolidone (NVP), and 4 parts by weight of 2-hydroxyethyl acrylate (HEA) As a photopolymerization initiator (pre-added photopolymerization initiator), 0.035 parts by weight of 1-hydroxycyclohexyl phenyl ketone (“IRGACURE 184" manufactured by BASF), and 2,2-dimethoxy-1,2-diphenylethane-1 -ON (BASF "IRGACURE 651”): 0.035 parts by weight was added. The composition was irradiated with ultraviolet light, prepolymerization was carried out until the viscosity at room temperature was about 20 Pa ⁇ s, and a prepolymer having a polymerization rate of about 8% was obtained.
  • 2EHA 2-ethylhexyl acryl
  • a pressure-sensitive adhesive composition B was obtained in the same manner as in the preparation of the pressure-sensitive adhesive composition 1, except that the addition amount of the post-addition polymerization initiator was changed from 0.15 part by weight to 0.1 part by weight.
  • the composition of the monomer mixture is 2EHA: 30.5 parts by weight, isostearyl acrylate (ISTA): 30.5 parts by weight, isobonyl acrylate (IBXA): 19 parts by weight, and acrylic acid 4-hydroxybutyl (4HBA): changed to 20 parts by weight, and the addition amount of a photopolymerization initiator: 0.05 parts by weight of 1-hydroxycyclohexyl phenyl ketone, and 2,2-dimethoxy-1,2-diphenylethane -1- On: 0.05 parts by weight.
  • the pressure-sensitive adhesive composition C was obtained in the same manner as in the preparation of the pressure-sensitive adhesive composition 1 except for these changes.
  • ⁇ Release agent solution B > 10 parts by weight of a 30% toluene solution of vinyl group-containing addition silicone (Shin-Etsu Chemical "KS-847T”) and 1 part by weight of a platinum catalyst for curing silicone (Shin-Etsu Chemical "CAT-PL-50T”) in volume ratio 1
  • a release agent solution B was prepared by diluting with a mixed solvent of toluene and hexane of 1: 1 so as to obtain a predetermined concentration shown in Table 1.
  • Example 1 ⁇ Production of base material release film> On one side of a 75 ⁇ m thick biaxially stretched polyester film (“Lumirror XD500P” manufactured by Toray Advanced Materials Co., Ltd.), a wire of release agent solution B prepared so that the solid content of silicone is 1.25% by weight, It applied using a bar (# 15), and heated for 1 minute with a 130 degreeC hot-air dryer, and formed the mold release layer.
  • a wire of release agent solution B prepared so that the solid content of silicone is 1.25% by weight
  • a pressure-sensitive adhesive composition A is applied to a thickness of 150 ⁇ m on the release layer-forming surface of the applied substrate release film described above to form an applied layer, and a cover release film is attached to the surface of the applied layer to form a laminate.
  • the laminate is irradiated with ultraviolet light from the cover release film side under the conditions of illuminance: 6.5 mW / cm 2 and integrated light quantity: 1500 mJ / cm 2 to photocure the coated layer to form a photocurable pressure-sensitive adhesive layer.
  • the adhesive sheet which has a peeling film on both sides of this was obtained.
  • Examples 2 to 6 and Comparative Examples 1 to 3 The type and concentration of the release agent solution at the time of preparation of the cover release film, the wire diameter (wire count) of the wire bar, and the type of the pressure-sensitive adhesive composition were changed as shown in Table 1. A photocurable pressure-sensitive adhesive sheet having release films on both sides was produced in the same manner as in Example 1 except for these changes.
  • ⁇ Peeling force of release film> A release film-attached pressure-sensitive adhesive sheet is cut into a width of 50 mm, and a 180 ° peel test is performed at a tension rate of 0.3 m / min using a tensile tester under an environment of 23 ° C. Each peeling force at the time of peeling a cover release film was measured.
  • Table 1 shows the release layer configuration (type of release agent solution and silicone concentration, thickness, and Si amount) in the cover release films of Examples and Comparative Examples, type of pressure sensitive adhesive, and peel strength evaluation results. Show.
  • the peeling force of the substrate release film was about 0.2 N / 50 mm, and no particular difference was observed.
  • Comparative Example 3 in which the same release agent was used for the substrate release film and the cover release film, the release force of the cover release film after photocuring of the pressure-sensitive adhesive sheet is 10% of the release force of the substrate release film. It was more than doubled and peeling was difficult. Also in Comparative Example 1 in which the type of silicone release agent of the cover release film and the composition of the adhesive were changed, the peel force of the cover release film was significantly increased as in Comparative Example 3.
  • Comparative Example 2 in which the concentration and thickness of the release agent solution at the time of producing the cover release film were larger than those in Comparative Example 1, the amount of Si per unit area of the release layer increased, and the pressure-sensitive adhesive sheet was photocured. The peel force of the cover release film was even greater than that of Comparative Example 1.
  • Example 2 and Example 3 in which the composition of the adhesive was changed using the same cover release film as in Example 1, the peel strength of the cover release film was equivalent to that in Example 1. Also in Example 6 using the same pressure-sensitive adhesive sheet as Example 2, the releasability of the cover release film after photocuring the pressure-sensitive adhesive sheet was good.
  • the release of the pressure-sensitive adhesive sheet after photocuring is performed by attaching a release sheet provided with a release layer having a predetermined range of Si atomic weight per unit area to a photocurable pressure-sensitive adhesive sheet containing a UV absorber. It turns out that the excessive raise of the peeling force of a film can be suppressed.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesive Tapes (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Laminated Bodies (AREA)

Abstract

La présente invention concerne une feuille adhésive (1) avec un film de démoulage qui est pourvue : d'une feuille adhésive photodurcissable (50) qui a une première surface principale et une seconde surface principale ; et d'un premier film de démoulage (10) qui est fixé de manière provisoire à la première surface principale de la feuille adhésive. Le premier film de démoulage comprend une couche de démoulage (15) sur un substrat de film (11) ; et la couche de démoulage (15) est en contact avec la feuille adhésive (50). La feuille adhésive (50) contient un polymère acrylique photodurcissable et un absorbant d'ultraviolets. La couche de démoulage (15) est une couche de démoulage à base de silicone, et a une teneur en atomes de Si de 0,02 à 0,07 g/m2.
PCT/JP2018/038375 2017-12-21 2018-10-15 Feuille adhésive avec film de démoulage et procédé de fabrication associé Ceased WO2019123799A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CN201880076662.3A CN111465668B (zh) 2017-12-21 2018-10-15 带脱模膜的粘合片及其制造方法
KR1020207020636A KR102567694B1 (ko) 2017-12-21 2018-10-15 이형 필름을 갖는 점착 시트 및 그 제조 방법
SG11202005787TA SG11202005787TA (en) 2017-12-21 2018-10-15 Release film-equipped pressure sensitive adhesive sheet and method for manufacturing the same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2017245614A JP7659962B2 (ja) 2017-12-21 2017-12-21 離型フィルム付き粘着シート
JP2017-245614 2017-12-21

Publications (1)

Publication Number Publication Date
WO2019123799A1 true WO2019123799A1 (fr) 2019-06-27

Family

ID=66993289

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2018/038375 Ceased WO2019123799A1 (fr) 2017-12-21 2018-10-15 Feuille adhésive avec film de démoulage et procédé de fabrication associé

Country Status (6)

Country Link
JP (3) JP7659962B2 (fr)
KR (1) KR102567694B1 (fr)
CN (1) CN111465668B (fr)
SG (1) SG11202005787TA (fr)
TW (1) TWI791076B (fr)
WO (1) WO2019123799A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114730040A (zh) * 2019-11-19 2022-07-08 日东电工株式会社 带粘合剂的光学薄膜及其制造方法
CN115103887A (zh) * 2020-02-14 2022-09-23 日东电工株式会社 带脱模薄膜的粘合片及其制造方法

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112334530B (zh) 2018-06-21 2023-12-12 凸版印刷株式会社 保护膜和片材
JP7828713B2 (ja) 2019-12-06 2026-03-12 リンテック株式会社 粘着シート、粘着剤層付き光学フィルム、および光学積層体
JP7584906B2 (ja) * 2020-05-01 2024-11-18 日東電工株式会社 粘着シート
KR20240089054A (ko) * 2021-10-27 2024-06-20 닛토덴코 가부시키가이샤 광 경화성 점착 시트
WO2023074555A1 (fr) * 2021-10-27 2023-05-04 日東電工株式会社 Feuille adhésive photodurcissable
JP7435889B1 (ja) 2023-07-05 2024-02-21 王子ホールディングス株式会社 粘着剤シート及び積層体
KR20260029829A (ko) * 2024-08-26 2026-03-05 도레이첨단소재 주식회사 리사이클링 이형필름 및 이를 포함하는 소자

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015151473A (ja) * 2014-02-14 2015-08-24 日東電工株式会社 光反応物層含有シート、及び、その製造方法
JP2016155981A (ja) * 2015-02-26 2016-09-01 日東電工株式会社 紫外線硬化型アクリル系粘着剤組成物、紫外線硬化型アクリル系粘着剤層、粘着剤層付き偏光フィルム、紫外線硬化型アクリル系粘着剤層の製造方法、及び画像表示装置
JP2017003906A (ja) * 2015-06-15 2017-01-05 日東電工株式会社 両面粘着剤層付偏光フィルムおよび画像表示装置

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5107761B2 (ja) * 2008-03-24 2012-12-26 三菱樹脂株式会社 離型フィルム
JP2012193221A (ja) 2011-03-15 2012-10-11 Mitsubishi Plastics Inc 粘着シート
JP5945393B2 (ja) 2011-09-30 2016-07-05 日東電工株式会社 粘着シート
JP5903978B2 (ja) 2012-03-28 2016-04-13 住友化学株式会社 粘着剤付き光学部材の製造方法
KR102176802B1 (ko) * 2013-03-11 2020-11-10 린텍 가부시키가이샤 점착 시트 및 가공된 디바이스 관련 부재의 제조 방법
JP2014189660A (ja) 2013-03-27 2014-10-06 Lintec Corp 積層体、粘着ロール、および当該積層体を用いる粘着剤層含有積層構造体の製造方法
JP2014226923A (ja) * 2013-05-28 2014-12-08 三菱樹脂株式会社 積層フィルム

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015151473A (ja) * 2014-02-14 2015-08-24 日東電工株式会社 光反応物層含有シート、及び、その製造方法
JP2016155981A (ja) * 2015-02-26 2016-09-01 日東電工株式会社 紫外線硬化型アクリル系粘着剤組成物、紫外線硬化型アクリル系粘着剤層、粘着剤層付き偏光フィルム、紫外線硬化型アクリル系粘着剤層の製造方法、及び画像表示装置
JP2017003906A (ja) * 2015-06-15 2017-01-05 日東電工株式会社 両面粘着剤層付偏光フィルムおよび画像表示装置

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114730040A (zh) * 2019-11-19 2022-07-08 日东电工株式会社 带粘合剂的光学薄膜及其制造方法
CN115103887A (zh) * 2020-02-14 2022-09-23 日东电工株式会社 带脱模薄膜的粘合片及其制造方法
CN115103887B (zh) * 2020-02-14 2025-04-01 日东电工株式会社 带脱模薄膜的粘合片及其制造方法

Also Published As

Publication number Publication date
SG11202005787TA (en) 2020-07-29
JP7659962B2 (ja) 2025-04-10
KR102567694B1 (ko) 2023-08-18
CN111465668B (zh) 2022-05-10
CN111465668A (zh) 2020-07-28
TW201930521A (zh) 2019-08-01
KR20200100128A (ko) 2020-08-25
JP2019112505A (ja) 2019-07-11
TWI791076B (zh) 2023-02-01
JP2024138047A (ja) 2024-10-07
JP2023009099A (ja) 2023-01-19

Similar Documents

Publication Publication Date Title
KR102567694B1 (ko) 이형 필름을 갖는 점착 시트 및 그 제조 방법
JP7720688B2 (ja) 光架橋性粘着剤およびその利用
JP7251073B2 (ja) 粘着シート、剥離シート付き粘着シート、積層体及び積層体の製造方法
KR102721050B1 (ko) 이형 필름을 구비한 점착 시트 및 그 제조 방법
JP7305939B2 (ja) 粘着シート、積層体及び積層体の製造方法
JP6323851B2 (ja) 光反応物層含有シート、及び、その製造方法
JP2022039946A (ja) 粘着剤組成物、光硬化性粘着剤層、及び光硬化性粘着シート
JP7207379B2 (ja) 粘着シート、剥離シート付き粘着シート、積層体及び積層体の製造方法
JP7279339B2 (ja) 粘着シート、積層体及び積層体の製造方法
WO2023074554A1 (fr) Feuille adhésive photodurcissable
JP7172058B2 (ja) 積層粘着シート及び積層粘着シートの製造方法
JP2022170568A (ja) 活性エネルギー線硬化型粘着シート及び表示装置
JP2020100748A (ja) 離型フィルム付き粘着シートおよびその製造方法
JP7620749B2 (ja) 粘着シートの製造方法、粘着シート付き光学フィルムの製造方法及び画像表示装置の製造方法
JP7567644B2 (ja) 活性エネルギー線硬化型粘着シート及び表示装置
JP2005023115A (ja) 感圧型両面接着テープ又はシート
JP2025023630A (ja) 光学粘着シート
JP2025023631A (ja) 光学粘着シート
JP2025023632A (ja) 光学粘着シート
WO2024024861A1 (fr) Feuille adhésive et procédé de pelage de feuille adhésive
JP2022170567A (ja) 活性エネルギー線硬化型粘着シート及び表示装置
CN119768480A (zh) 粘合片的制造方法及带粘合片的光学膜的制造方法
WO2022045131A1 (fr) Composition d'adhésif, couche d'adhésif photodurcissable, et feuille adhésive photodurcissable
JP2023084557A (ja) 粘着剤組成物及び粘着シート並びに積層体

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 18892481

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

ENP Entry into the national phase

Ref document number: 20207020636

Country of ref document: KR

Kind code of ref document: A

122 Ep: pct application non-entry in european phase

Ref document number: 18892481

Country of ref document: EP

Kind code of ref document: A1