WO2023074554A1 - Feuille adhésive photodurcissable - Google Patents

Feuille adhésive photodurcissable Download PDF

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Publication number
WO2023074554A1
WO2023074554A1 PCT/JP2022/039265 JP2022039265W WO2023074554A1 WO 2023074554 A1 WO2023074554 A1 WO 2023074554A1 JP 2022039265 W JP2022039265 W JP 2022039265W WO 2023074554 A1 WO2023074554 A1 WO 2023074554A1
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WO
WIPO (PCT)
Prior art keywords
adhesive sheet
sensitive adhesive
photocurable
mass
pressure
Prior art date
Application number
PCT/JP2022/039265
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English (en)
Japanese (ja)
Inventor
陽介 清水
大器 下栗
裕貴 小原
崇弘 野中
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日東電工株式会社
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Application filed by 日東電工株式会社 filed Critical 日東電工株式会社
Priority to CN202280071857.5A priority Critical patent/CN118159618A/zh
Publication of WO2023074554A1 publication Critical patent/WO2023074554A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • 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
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C09J7/38—Pressure-sensitive adhesives [PSA]

Definitions

  • the laminated structure of the display panel includes elements with high surface smoothness, such as glass substrates and cover glass. Therefore, adhesive sheets used for manufacturing display panels (adhesive sheets for display panel applications) are required to have high adhesiveness.
  • the present invention provides a photocurable pressure-sensitive adhesive sheet that is suitable for reducing environmental loads and suitable for use in display panels.
  • the adhesive sheet S was attached to an alkali glass plate prepared by the float method, and then the adhesive sheet S on the alkali glass plate was heated under conditions of 50°C, 0.5 MPa, and 15 minutes. After pressure treatment and subsequent photo-curing treatment of the adhesive sheet S under the conditions of an integrated irradiation light amount of 3000 mJ/cm 2 , 23 ° C., 50% relative humidity, peel angle 180 ° and pulling speed 300 mm / min. A peeling test is performed by peeling the adhesive sheet S from the alkali glass plate under the conditions to measure the peel strength (peel strength F1). The first test is more specifically as described below with respect to the examples.
  • Methods for adjusting the peel strength F1 include, for example, selection of the type of base polymer in the adhesive sheet S, adjustment of the molecular weight, and adjustment of the blending amount. Selecting the type of base polymer involves adjusting the composition of the monomers forming the base polymer. Methods for adjusting the peel strength F1 include selection of the types of components other than the base polymer in the pressure-sensitive adhesive sheet S and adjustment of the blending amounts of the components. Such components include photopolymerizable polyfunctional compounds, photopolymerization initiators, silane coupling agents, and oligomers. The method for adjusting the peel strength as described above also applies to the peel strength F2, which will be described later.
  • the light transmittance R2 is preferably 14% or less, more preferably 13% or less, more preferably 12% or less, more preferably 11% or less, more preferably 10% or less, more preferably 9 % or less, more preferably 8% or less, more preferably 7% or less, more preferably 6% or less, more preferably 5% or less.
  • the light transmittance R2 is substantially 0.1% or more.
  • a method for measuring the light transmittance of the pressure-sensitive adhesive sheet S is as described later with regard to Examples.
  • Methods for adjusting the shear storage elastic modulus G1 include, for example, selection of the type of base polymer in the adhesive sheet S, adjustment of the molecular weight, and adjustment of the compounding amount. Selecting the type of base polymer involves adjusting the composition of the monomers forming the base polymer. Moreover, the method for measuring the shear storage modulus G1 is as described later with regard to Examples.
  • the adhesive sheet S contains a base polymer as a photopolymer, a photopolymerizable polyfunctional compound (first photopolymerizable polyfunctional compound), and a photopolymerization initiator, and has photocurability.
  • the adhesive sheet S may contain a monofunctional monomer as a polymerizable component in addition to the photopolymerizable polyfunctional compound.
  • a photopolymer is a polymer produced by photopolymerization.
  • Photopolymerization is a polymerization method in which the polymerization reaction of polymerizable components proceeds by irradiation with active energy rays such as ultraviolet rays.
  • photocurability refers to the property of becoming highly elastic when irradiated with active energy rays such as ultraviolet rays.
  • the ratio of the monofunctional monomer in the polymerizable component forming the base polymer is preferably 50% by mass or more, more preferably 60% by mass or more, and further preferably 60% by mass or more, from the viewpoint of appropriately expressing basic properties such as adhesiveness in the adhesive sheet S. It is preferably 70% by mass or more, particularly preferably 75% by mass or more. The same ratio is, for example, 99% by mass or less.
  • the polymerizable component may contain, as a monofunctional monomer, a copolymerizable monomer that can be copolymerized with the above monofunctional monomer.
  • copolymerizable monomers include monomers having a polar group.
  • Polar group-containing monomers include, for example, hydroxyl group-containing monomers, carboxy group-containing monomers, and monomers having a nitrogen atom-containing ring.
  • a polar group-containing monomer is useful for modifying the acrylic polymer, such as ensuring the cohesive strength of the acrylic polymer.
  • the ratio of the carboxyl group-containing monomer in the polymerizable component is preferably 1% by mass or more, more preferably 3% by mass, from the viewpoint of ensuring the cohesive force of the adhesive sheet S and ensuring the adhesion of the adhesive sheet S to the adherend. It is at least 5% by mass, more preferably at least 5% by mass. The same ratio is preferably 20% by mass or less, more preferably 10% by mass or less, from the viewpoints of adjusting the glass transition temperature of the acrylic polymer and avoiding the risk of acid corrosion of the adherend.
  • bifunctional (meth)acrylates include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol dimethacrylate, 1,6-hexanediol di (meth)acrylate, 1,9-nonanediol di(meth)acrylate, glycerin di(meth)acrylate, neopentyl glycol di(meth)acrylate, stearic acid-modified pentaerythritol di(meth)acrylate, dicyclopentenyl diacrylate, Examples include di(meth)acryloyl isocyanurate and alkylene oxide-modified bisphenol di(meth)acrylate.
  • the molecular weight of the polyfunctional monomer is preferably 5000 or less, more preferably 3000 or less, still more preferably 2000 or less, particularly preferably 1000 or less, and preferably 200 or more. Such a configuration is preferable from the viewpoint of appropriately adjusting the viscoelasticity (for example, shear storage modulus and loss tangent) of the base polymer.
  • the weight average molecular weight (Mw) of the polyfunctional oligomer is preferably 20,000 or less, more preferably 15,000 or less, and preferably 5,000 or more. Such a configuration is preferable from the viewpoint of appropriately adjusting the viscoelasticity (for example, shear storage modulus and loss tangent) of the base polymer.
  • the weight average molecular weight is calculated by measuring with gel permeation chromatography (GPC) and converting to polystyrene.
  • Examples of anions include Cl ⁇ , Br ⁇ , I ⁇ , ZnCl 3 ⁇ , HSO 3 ⁇ , BF 4 ⁇ , PF 6 ⁇ , AsF 6 ⁇ , SbF 6 ⁇ , CH 3 SO 3 ⁇ , CF 3 SO 3 ⁇ , C 4 F 9 HSO 3 ⁇ , (C 6 F 5 ) 4 B ⁇ , and (C 4 H 9 ) 4 B ⁇ .
  • Commercially available cationic photopolymerization initiators include, for example, San-Apro CPI-100, CPI-100P, CPI-101A, CPI-200K, CPI-210S, IK-1, IK-2, CPI-310B, and CPI-410S.
  • Examples of commercially available cationic photopolymerization initiators include SP-056, SP-066, SP-130, SP-140, SP-150, SP-170, SP-171, and SP-172 manufactured by ADEKA. is also mentioned.
  • methyl methacrylate is preferable because it has a high glass transition temperature and excellent compatibility with the base polymer.
  • Preferred alicyclic alkyl (meth)acrylates are dicyclopentanyl acrylate, dicyclopentanyl methacrylate, cyclohexyl acrylate and cyclohexyl methacrylate. That is, the acrylic oligomer is a monomer component containing methyl methacrylate and at least one selected from the group consisting of dicyclopentanyl acrylate, dicyclopentanyl methacrylate, cyclohexyl acrylate, and cyclohexyl methacrylate. A coalescence is preferred.
  • Thermal polymerization initiators include, for example, azo polymerization initiators and peroxide polymerization initiators.
  • azo polymerization initiators include 2,2'-azobisisobutyronitrile, 2,2'-azobis-2-methylbutyronitrile, 2,2'-azobis(2-methylpropionate)dimethyl, 4,4'-azobis-4-cyanovaleric acid, azobisisovaleronitrile, 2,2'-azobis(2-amidinopropane) dihydrochloride, 2,2'-azobis[2-(5-methyl-2- imidazolin-2-yl)propane]dihydrochloride, 2,2'-azobis(2-methylpropionamidine) disulfate, and 2,2'-azobis(N,N'-dimethyleneisobutyramidine) dihydrochloride mentioned.
  • Peroxide polymerization initiators include, for example, dibenzoyl peroxide, t-butyl permaleate, and lauroyl peroxid
  • Chain transfer agents include ⁇ -thioglycerol, lauryl mercaptan, glycidyl mercaptan, mercaptoacetic acid, 2-mercaptoethanol, thioglycolic acid, 2-ethylhexyl thioglycolate, 2,3-dimercapto-1-propanol, and ⁇ -methylstyrene. Dimers are included.
  • a method for measuring the loss tangent tan ⁇ is as described later with regard to Examples.
  • the loss tangent of the pressure-sensitive adhesive sheet can be measured using, for example, a dynamic viscoelasticity measuring device (trade name “Advanced Rheometric Expansion System (ARES)”, manufactured by Rheometric Scientific).
  • the measurement mode is shear mode
  • the measurement temperature range is ⁇ 50° C. to 150° C.
  • the temperature increase rate is 5° C./min
  • the frequency is 1 Hz.
  • a prepolymer composition is prepared (prepolymer composition preparation step). Specifically, first, a mixture (liquid) containing the above-described monofunctional monomer for forming the base polymer and a photopolymerization initiator is prepared. This mixture is solvent-free. Next, by irradiating the mixture with ultraviolet rays, part of the monofunctional monomers in the mixture is photopolymerized to obtain a prepolymer composition (solvent-free prepolymer composition).
  • Light sources for ultraviolet irradiation include, for example, ultraviolet LED lights, black lights, high-pressure mercury lamps, and metal halide lamps.
  • a second photopolymerizable polyfunctional compound, a photopolymerization initiator, and optionally other components are added to the prepolymer composition to prepare an adhesive composition (adhesive composition preparation process).
  • Other ingredients include, for example, antioxidants and silane coupling agents. Since the adhesive composition does not contain a solvent, it is a solvent-free adhesive composition.
  • 3A to 3C show an example of how to use the adhesive sheet S.
  • the adhesive sheet S is photo-cured between members by ultraviolet irradiation (photo-curing step).
  • the ultraviolet irradiation causes the photopolymerization reaction of the first photopolymerizable polyfunctional compound to proceed in the adhesive sheet S, forming a photopolymerized product of the first photopolymerizable polyfunctional compound. Since the photopolymerization reaction proceeds around the base polymer (the first photopolymerization polymer and the second photopolymerization polymer having a photocrosslinking structure), the photopolymerization product of the first photopolymerizable polyfunctional compound interacts with the base polymer. It is formed while forming an interstitial polymer network (IPN).
  • IPN interstitial polymer network
  • ⁇ Preparation of prepolymer composition> In a flask, 71 parts by mass of n-butyl acrylate (BA), 13 parts by mass of N-vinyl-2-pyrrolidone (NVP), 13 parts by mass of 4-hydroxybutyl acrylate (4HBA), and acryloylmorpholine ( ACMO) 3 parts by weight of the monomer mixture, the first photopolymerization initiator (product name "Irgacure 184", 1-hydroxy-cyclohexyl-phenyl-ketone, manufactured by BASF) 0.031 parts by weight, the second photopolymerization After adding 0.031 parts by mass of an initiator (product name “Irgacure 651”, 2,2-dimethoxy-1,2-diphenylethan-1-one, manufactured by BASF), the mixture was exposed to ultraviolet light under a nitrogen atmosphere.
  • BA n-butyl acrylate
  • NDP N-vinyl-2-pyrrolidone
  • 4HBA 4-hydroxybuty
  • the pressure-sensitive adhesive composition C1 was applied onto the release-treated surface of the first release liner (product name “DIAFOIL MRF”, thickness 75 ⁇ m, manufactured by Mitsubishi Chemical Corporation) having a release-treated surface on one side to form a coating film. formed.
  • the release-treated surface of the second release liner product name: "Diafoil MRE", thickness: 75 ⁇ m, manufactured by Mitsubishi Chemical Corporation
  • the coating film between the release liners was irradiated with ultraviolet rays from the second release liner side, and the coating film was photocured to form a pressure-sensitive adhesive layer with a thickness of 100 ⁇ m (ultraviolet irradiation step).
  • ultraviolet irradiation a black light (manufactured by Toshiba) was used as a light source, the illuminance was set at 6.5 mW/cm 2 , and the irradiation integrated light amount was set at 1500 mJ/cm 2 .
  • Example 1 ⁇ Preparation of post-addition component solution> First, 5.8 parts by mass of a polyfunctional acrylate monomer (product name “Viscoat #295”, trimethylolpropane triacrylate (TMPTA), manufactured by Osaka Organic Chemical Industry Co., Ltd.) as a first photopolymerizable polyfunctional compound, and a third 0.3 parts by mass of a photopolymerization initiator (product name “Irgacure 819”, manufactured by BASF), 7 parts by mass of an ultraviolet absorber (product name “Tinosorb S”, manufactured by BASF), and 94.2 parts by mass of ethyl acetate as a solvent were mixed to prepare a post-addition component solution (anything other than the solvent in the solution is a post-addition component).
  • Table 1 shows the composition of the post-addition component solution. In Table 1, the unit of the blending amount of each component is relative "parts by mass”.
  • the base pressure-sensitive adhesive sheet changed into a photocurable pressure-sensitive adhesive sheet due to the permeation of the post-addition component.
  • 1 part by mass of the first photopolymerizable polyfunctional compound per 100 parts by mass of the prepolymer composition and the second photopolymerizable polyfunctional compound i.e., 100 parts by mass of the base polymer
  • the base adhesive sheet parts by mass of the first photopolymerizable polyfunctional compound per 100 parts by mass of the base polymer are shown in Tables 2 and 3).
  • the measurement sample was fixed to a parallel plate jig with a diameter of 7.9 mm using a dynamic viscoelasticity measuring device (product name “Advanced Rheometric Expansion System (ARES)”, manufactured by Rheometric Scientific) and then moved.
  • a viscoelasticity measurement was performed.
  • the measurement mode was the shear mode
  • the measurement temperature range was ⁇ 50° C. to 150° C.
  • the temperature increase rate was 5° C./min
  • the frequency was 1 Hz.
  • the shear storage modulus G1 (MPa) at 25°C was read. The values are shown in Tables 2 and 3.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Adhesive Tapes (AREA)

Abstract

Une feuille adhésive (S) qui est une feuille adhésive photodurcissable comprenant un polymère de base servant de photopolymère. Après qu'une feuille adhésive photodurcissable (S) a été collée à une feuille de verre alcalin fabriquée par un procédé de flottage, on procède à une opération de chauffage et de pressurisation dans des conditions prescrites ultérieures, et on met en œuvre un procédé de photodurcissement, dans une condition ultérieure consistant en une quantité de lumière intégrée irradiée de 3 000 mJ/cm2, la feuille adhésive photodurcissable (S) ayant une résistance au pelage de 1,5 N/10 mm ou plus dans un essai de pelage dans lequel la feuille adhésive photodurcissable (S) est détachée par pelage de la feuille de verre alcalin dans les conditions prescrites.
PCT/JP2022/039265 2021-10-27 2022-10-21 Feuille adhésive photodurcissable WO2023074554A1 (fr)

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CN202280071857.5A CN118159618A (zh) 2021-10-27 2022-10-21 光固化性粘合片

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JP2021175660 2021-10-27

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0260981A (ja) * 1988-08-29 1990-03-01 Sekisui Chem Co Ltd アクリル系粘着テープもしくはシートの製造方法
WO2016117045A1 (fr) * 2015-01-21 2016-07-28 株式会社寺岡製作所 Feuille adhésive autocollante, procédé de fabrication de celle-ci et procédé de production d'élément optique utilisant cette feuille
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
JP2019112505A (ja) * 2017-12-21 2019-07-11 日東電工株式会社 離型フィルム付き粘着シートおよびその製造方法
JP2020186312A (ja) * 2019-05-14 2020-11-19 王子ホールディングス株式会社 粘着シートの製造方法及び積層体の製造方法
WO2022045130A1 (fr) * 2020-08-28 2022-03-03 日東電工株式会社 Feuille adhésive photodurcissable

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0260981A (ja) * 1988-08-29 1990-03-01 Sekisui Chem Co Ltd アクリル系粘着テープもしくはシートの製造方法
WO2016117045A1 (fr) * 2015-01-21 2016-07-28 株式会社寺岡製作所 Feuille adhésive autocollante, procédé de fabrication de celle-ci et procédé de production d'élément optique utilisant cette feuille
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
JP2019112505A (ja) * 2017-12-21 2019-07-11 日東電工株式会社 離型フィルム付き粘着シートおよびその製造方法
JP2020186312A (ja) * 2019-05-14 2020-11-19 王子ホールディングス株式会社 粘着シートの製造方法及び積層体の製造方法
WO2022045130A1 (fr) * 2020-08-28 2022-03-03 日東電工株式会社 Feuille adhésive photodurcissable

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TW202330842A (zh) 2023-08-01
CN118159618A (zh) 2024-06-07

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