WO2015190558A1 - Feuille adhésive double face pour dispositifs d'affichage d'images et article correspondant - Google Patents

Feuille adhésive double face pour dispositifs d'affichage d'images et article correspondant Download PDF

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Publication number
WO2015190558A1
WO2015190558A1 PCT/JP2015/066885 JP2015066885W WO2015190558A1 WO 2015190558 A1 WO2015190558 A1 WO 2015190558A1 JP 2015066885 W JP2015066885 W JP 2015066885W WO 2015190558 A1 WO2015190558 A1 WO 2015190558A1
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Prior art keywords
meth
acrylate
compound
image display
double
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PCT/JP2015/066885
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English (en)
Japanese (ja)
Inventor
照士 高橋
研二 芥
康弘 穂積
吉浩 箱根
徳田　清久
貴文 水口
英照 亀谷
隼 本橋
Original Assignee
日本化薬株式会社
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Priority claimed from JP2015112948A external-priority patent/JP2016222861A/ja
Application filed by 日本化薬株式会社 filed Critical 日本化薬株式会社
Priority to CN201580030851.3A priority Critical patent/CN106459724A/zh
Publication of WO2015190558A1 publication Critical patent/WO2015190558A1/fr

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    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C09J175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers

Definitions

  • the present invention relates to an ultraviolet curable adhesive composition for image display for laminating at least two optical substrates, a double-sided pressure-sensitive adhesive sheet using the ultraviolet curable adhesive composition for image display, and an optical device using the same
  • the present invention relates to a method of manufacturing a member.
  • a touch panel In recent years, display devices that allow screen input by attaching a touch panel to a display screen of a display device such as a liquid crystal display, a plasma display, or an organic EL display have been widely used.
  • a glass plate or a resin film on which a transparent electrode is formed is bonded with a slight gap facing each other. If necessary, a transparent protection made of glass or resin is provided on the touch surface. It has a structure in which plates are bonded together.
  • Patent Document 2 a technique for bonding a transparent protective plate and an image display device with an ultraviolet curable adhesive composition has been proposed (Patent Document 2).
  • Patent Document 2 since the production efficiency can be improved by using the transparent double-sided pressure-sensitive adhesive sheet as compared with the method using the ultraviolet curable adhesive composition, there is an advantage over the ultraviolet curable adhesive composition.
  • the curable component is not polymerized, it is difficult to form a sheet in the case where a conventional general ultraviolet curable adhesive composition is made into a transparent double-sided pressure-sensitive adhesive sheet, and the desired curing is achieved. It was difficult to obtain physical properties. Therefore, it has been desired to develop a transparent double-sided pressure-sensitive adhesive sheet that can ensure cured properties such as low dielectric constant, adhesion, and low shrinkage.
  • the present invention can obtain an optical member such as a display unit having little damage to the optical substrate, good productivity, good curability and adhesion, and has high adhesion to the substrate. It aims at providing the double-sided adhesive sheet for image display apparatuses which can obtain an optical member (touch panel etc.) with high intensity
  • the present invention relates to the following (1) to (15).
  • (meth) acrylate (K) selected from the group consisting of urethane (meth) acrylate, (meth) acrylate having a polyisoprene skeleton or (meth) acrylate having a butadiene skeleton, a softener component
  • the double-sided adhesive sheet for image display apparatuses obtained by drying the ultraviolet curable resin composition containing (G) at 80 degreeC or more.
  • the (meth) acrylate is urethane (meth) acrylate, and the urethane (meth) acrylate reacts the compound (A), the compound (B), the compound (C) and the compound (D) shown below.
  • a double-sided pressure-sensitive adhesive sheet for an image display device comprising the polyurethane compound (E) according to (3), wherein the hydrogenated polybutadiene polyol compound (A) has an iodine value of 20 or less.
  • the double-sided pressure-sensitive adhesive sheet for an image display device comprising the polyurethane compound (E) according to (3) or (4), wherein the polyisocyanate compound (B) is an aliphatic diisocyanate compound.
  • a double-sided pressure-sensitive adhesive sheet for an image display device comprising: (7)
  • the diol compound (D) other than the compound (A) includes the polyurethane compound (E) according to any one of (3) to (6), which is a polyether polyol. Double-sided adhesive sheet.
  • a double-sided pressure-sensitive adhesive sheet for an image display device comprising the polyurethane compound (E) according to any one of (1) to (7) and a polymerizable compound (F) other than (E).
  • the softening agent component (G) includes any one of a hydroxyl group-containing polymer and a terpene resin, or both, according to any one of (1) to (8) Double-sided pressure-sensitive adhesive sheet for image display devices.
  • a touch panel comprising the double-sided pressure-sensitive adhesive sheet for an image display device according to any one of (1) to (9).
  • K urethane
  • G urethane
  • the optical base material is pasted by the following steps 1 and 2 using the double-sided pressure-sensitive adhesive sheet for an image display device according to any one of (1) to (9) and (12) to (13).
  • a method for manufacturing an image display device which also provides an image display device.
  • Process 1 The process of peeling the single-sided release film of the double-sided adhesive sheet for image display apparatuses with a release film with respect to at least 1 optical base material, and arrange
  • Process 2 The process of peeling off the release film of the remaining single side
  • Process 3 The process of irradiating an ultraviolet-ray through the optical base material which has a light-shielding part to the double-sided adhesive sheet for image display apparatuses in the bonded optical base material, and hardening this hardened
  • the cured film of the double-sided pressure-sensitive adhesive sheet for image display device of the present invention is excellent in flexibility and has high moisture resistance, heat resistance, and light resistance. It is possible to effectively prevent problems from occurring.
  • the double-sided PSA sheet for an image display device of the present invention is at least one (meth) selected from the group consisting of urethane (meth) acrylate, (meth) acrylate having a polyisoprene skeleton, or (meth) acrylate having a butadiene skeleton.
  • a urethane (meth) acrylate urethane (meth) acrylate, (meth) acrylate having a polyisoprene skeleton, or (meth) acrylate having a butadiene skeleton.
  • it is preferable that both the said (meth) acrylate (K) and the softening agent component (G) are included.
  • the double-sided pressure-sensitive adhesive sheet for an image display device of the present invention is selected from the group consisting of urethane (meth) acrylate, (meth) acrylate having a polyisoprene skeleton, and (meth) acrylate having a polybutadiene skeleton as (meth) acrylate (K).
  • urethane (meth) acrylate Preferably, it is an embodiment containing at least one of urethane (meth) acrylate or (meth) acrylate having a polyisoprene skeleton.
  • the (meth) acrylate compound is preferably a high molecular weight oligomer or polymer.
  • the polymer means a high molecular weight body that does not include a (meth) acrylic polymer that is a high molecular weight body in which a (meth) acryl group is polymerized, and a (meth) acryloyl group remains.
  • (meth) acrylate means either one or both of methacrylate and acrylate. The same applies to “(meth) acrylic acid” and the like.
  • the urethane (meth) acrylate that can be suitably used for the double-sided pressure-sensitive adhesive sheet for an image display device of the present invention is obtained by reacting at least one hydroxy compound having a (meth) acryloyloxy group and an isocyanate compound (further as an optional component, a polyol). It is the (meth) acrylate obtained.
  • hydroxy compound having at least one (meth) acryloyloxy group include, for example, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4- Hydroxyethyl (meth) acrylate, cyclohexanedimethanol mono (meth) acrylate, polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, pentaerythritol tri (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) )
  • a (meth) acrylate compound having various hydroxyl groups such as acrylate, and a ring-opening reaction product of the above-mentioned (meth) acrylate compound having a hydroxyl group and ⁇ -caprolactone. Door can be.
  • isocyanate compound examples include, for example, P-phenylene diisocyanate, m-phenylene diisocyanate, P-xylene diisocyanate, m-xylene diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 4,4 ′.
  • -Aromatic diisocyanates such as diphenylmethane diisocyanate and naphthalene diisocyanate; aliphatic or alicyclic diisocyanates such as isophorone diisocyanate, hexamethylene diisocyanate, 4,4'-dicyclohexylmethane diisocyanate, hydrogenated xylene diisocyanate, norbornene diisocyanate, lysine diisocyanate ; Trimerization of one or more burettes of isocyanate monomers or the above diisocyanate compounds Polyisocyanates of the isocyanate and the like; the and the isocyanate compound include polyisocyanates obtained by urethane reaction of the polyol compound.
  • the polyol that can be used as an optional component is not particularly limited as long as it is a known polyol.
  • Specific examples include, for example, polyether polyols such as polyethylene glycol, polybutylene glycol, polytetramethylene glycol, polypropylene glycol and polyethylene glycol, and polyester polyols such as polyethylene glycol adipate, poly 1,4-butanediol adipate and polycaprolactone.
  • Glycols such as ethylene glycol, propylene glycol, butanediol, pentanediol, hexanediol and neopentyl glycol, cyclohexane dimethylol, polyisoprene glycol, polybutadiene glycol, hydrogenated bisphenol A, hydrogenated bisphenol F, spiro skeleton-containing alcohol, Alicyclic alkanes such as tricyclodecane dimethylol and pentacyclopentadecane dimethylol And alkylene oxide adducts thereof, hydrogenated polyisoprene, branched or linear long chain alkyl diols such as diols of hydrogenated polybutadiene, bisphenols such as bisphenol A and bisphenol F, and alkylene oxide adducts of bisphenols, Examples include polyols such as trimethylolpropane, ditrimethylolpropane, pentaerythritol and dip
  • the weight average molecular weight of the urethane (meth) acrylate is preferably about 5,000 to 100,000, and more preferably 10,000 to 80,000. When the weight average molecular weight is less than 5000, shrinkage increases, and when the weight average molecular weight is greater than 100,000, the curability is poor.
  • urethane (meth) acrylate can be used alone or in combination of two or more at any ratio.
  • the weight ratio of urethane (meth) acrylate in the ultraviolet curable agent composition for obtaining the double-sided pressure-sensitive adhesive sheet for an image display device of the present invention is usually 20 to 80% by weight, preferably 30 to 70% by weight.
  • the (meth) acrylate having the polyisoprene skeleton has a (meth) acryloyl group at the terminal or side chain of the polyisoprene molecule.
  • a (meth) acrylate having a polyisoprene skeleton can be obtained as “UC-203” (manufactured by Kuraray Co., Ltd.).
  • the (meth) acrylate having a polyisoprene skeleton preferably has a polystyrene-equivalent number average molecular weight of 1,000 to 50,000, more preferably about 25,000 to 45,000.
  • the weight ratio of the (meth) acrylate having a polyisoprene skeleton in the photocurable transparent adhesive composition for obtaining the double-sided pressure-sensitive adhesive sheet for an image display device of the present invention is usually 20 to 80% by weight, preferably 30 to 70% by weight. %.
  • the (meth) acrylate having the polybutadiene skeleton has a (meth) acryloyl group at the terminal or side chain of the polybutadiene molecule.
  • the (meth) acrylates having a polybutadiene skeleton are "TEAI-1000 (Nippon Soda Co., Ltd.)", “TE-2000 (Nippon Soda Co., Ltd.)", “EMA-3000 (Nippon Soda Co., Ltd.)” Manufactured by Kogyo Co., Ltd.).
  • the (meth) acrylate having a polybutadiene skeleton preferably has a polystyrene-equivalent number average molecular weight of 1,000 to 30,000, more preferably about 1,000 to 10,000.
  • the weight ratio of the (meth) acrylate having a polybutadiene skeleton in the photocurable transparent adhesive composition for obtaining the double-sided pressure-sensitive adhesive sheet for an image display device of the present invention is usually 10 to 80% by weight, preferably 20 to 70% by weight. It is.
  • the polyurethane compound (E) that can be used particularly preferably in the present invention is a reaction between the hydrogenated polybutadiene polyol (A) and the diol compound (D) other than the compound (A) and the polyisocyanate compound (B) (hereinafter referred to as “first”). And a (meth) acrylate compound (C) having at least one hydroxyl group is reacted with the remaining isocyanate group (hereinafter referred to as a second reaction).
  • the resulting polyurethane compound (E) preferably has a weight average molecular weight of 5,000 to 100,000, more preferably 10,000 to 80,000, particularly preferably 30,000 to 70,000.
  • the R value is preferably 1.1 to 2.0, more preferably 1.1 to 1.5.
  • any hydrogenated reduction product of a general polybutadiene polyol can be used.
  • the iodine value is particularly preferably 20 or less.
  • the hydroxyl value is preferably 400 or less, and more preferably 300 or less. Although a minimum is not specifically limited, For example, what is necessary is just 0.1 or more.
  • the molecular weight of (A) all generally available molecular weight distributions can be used, but those having a weight average molecular weight of 500 to 3000 are particularly preferred particularly when the balance between flexibility and curability is achieved. .
  • the molecular weight of (A) all generally available molecular weight distributions can be used, but those having a number average molecular weight of 500 to 5000 are preferred particularly when the balance between flexibility and curability is achieved. Those of 500 to 3000 are particularly preferred.
  • Examples of commercially available hydrogenated polybutadiene polyols (A) include Nippon Soda Co., Ltd .: GI-1000, GI-2000, GI-3000, CRAY VALLEY KRASOL HLBP-H 1000, HLBP-H 2000, HLBP-H 3000 etc. are mentioned. In addition, what contains an alkali salt can be used conveniently.
  • diol compound (D) other than the compound (A) used in the first reaction of the present invention include, for example, polyethers such as polyethylene glycol, polybutylene glycol, polytetramethylene glycol, polypropylene glycol, and polyethylene glycol.
  • Polyols polyethylene glycol adipate, poly 1,4-butanediol adipate, polyester polyols such as polycaprolactone, glycols such as ethylene glycol, propylene glycol, butanediol, pentanediol, hexanediol and neopentyl glycol, cyclohexane dimethylol, Polyisoprene glycol, polybutadiene glycol, hydrogenated bisphenol A, hydrogenated bisphenol F, spiro skeleton-containing alcohol, tricyclodeca Aliphatic alcohols such as dimethylol and pentacyclopentadecane dimethylol and their alkylene oxide adducts, hydrogenated polyisoprene, branched or linear long chain alkyl diols such as hydrogenated polybutadiene diols, bisphenol A, bisphenol F, etc.
  • polyester polyols such as polycaprolactone
  • the polyester polyol obtained by reaction of an acid etc. can be mentioned.
  • polyether polyols in order to improve flexibility and compatibility in the cured product of the ultraviolet curable adhesive composition of the present invention.
  • the molecular weight of the diol compound (D) other than the compound (A) all generally available molecular weight distributions can be used, but the number average molecular weight is particularly 50 when the balance between flexibility and curability is achieved. ⁇ 6000 is preferred, and 100 ⁇ 4000 is particularly preferred.
  • the structure derived from the diol compound (D) other than the compound (A) particularly preferably a polyether polyol such as polyethylene glycol
  • the polyethylene glycol skeleton and water are incorporated.
  • the number average molecular weight of polyethylene glycol is more preferably 2000 or less, and particularly preferably 500 or less.
  • a diol compound (D) other than the compound (A) is a diol other than the hydrogenated polybutadiene polyol (A) and the compound (A).
  • the compound (D) is preferably incorporated in an amount of 5 to 10 mol%.
  • the hydroxyl value is preferably 400 or less, and more preferably 300 or less.
  • polyethylene glycol which is an example of polyether polyols that can be suitably used in the first reaction of the present invention
  • all commercially available polyethylene glycols can be used.
  • PEG # 200T, PEG # 200, PEG # 300, PEG # 400, PEG # 600, PEG # 1000, PEG # 1500, PEG # 1540, PEG # 200, PEG # 4000, PEG # 4000P, PEG # 6000, PEG # 6000P, PEG # 11000, PEG # 20000, and the like, and urethane grades and the like whose moisture are controlled can also be used.
  • the water content is preferably 2% or less, particularly preferably 1% or less, in order to suppress thickening due to an increase in molecular weight.
  • hydrogenated polybutadiene polyol (A) and diol compound (D) other than compound (A) (particularly preferably polyether polyol such as polyethylene glycol) are used for the reaction.
  • diol compound (D) other than compound (A) (particularly preferably, a polyether polyol such as polyethylene glycol) is not particularly limited, but (A) component: (D) component is 9.999 in molar ratio. : 0.001 to 1: 9 is preferable, 9.999: 0.001 to 3: 7 is more preferable, and 9.999: 0.001 to 4: 6 is particularly preferable.
  • the number average molecular weight of the hydrogenated polybutadiene polyol (A) used in the present invention is the number average molecular weight of a diol compound (D) other than the compound (A) used (particularly preferably a polyether polyol such as polyethylene glycol). It is preferable to use a larger one in combination.
  • the number average molecular weight of the diol compound (D) other than the compound (A) (particularly preferably a polyether polyol such as polyethylene glycol) +500 is used as a hydrogenated polybutadiene polyol ( More preferably, the hydrogenated polybutadiene polyol (A) has a number average molecular weight of the diol compound (D) other than the compound (A) (particularly preferably a polyether polyol such as polyethylene glycol) +1000. Especially to have Masui.
  • the polyisocyanate compound (B) used in the first reaction is a compound comprising two or more isocyanate groups in one molecule.
  • an aliphatic diisocyanate compound, an aromatic diisocyanate compound, These trimers are exemplified.
  • the aliphatic diisocyanate compound as used herein means a diisocyanate compound in which an isocyanate group is bonded to a chain carbon atom, and a diisocyanate compound in which an isocyanate group is bonded to a carbon atom of a cyclic saturated hydrocarbon, and an aromatic diisocyanate compound.
  • an isocyanate compound in which an isocyanate group is bonded to a carbon atom of an aromatic ring means an isocyanate compound in which an isocyanate group is bonded to a carbon atom of an aromatic ring.
  • Examples of the aliphatic diisocyanate compound include 1,6-hexamethylene diisocyanate, isophorone diisocyanate, hydrogenated tolylene diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated diphenylmethane diisocyanate, 1,3-diisocyanate cyclohexane, 1,4-diisocyanate.
  • aromatic diisocyanate compounds include tolylene diisocyanate, xylylene diisocyanate, diphenylmethane diisocyanate, 1,5-naphthalene diisocyanate, tolidine diisocyanate, 1,6-phenylene diisocyanate, 1,4-phenylene diisocyanate, 1,6-phenylene. And diisocyanate monomers such as diisocyanate.
  • an aliphatic diisocyanate compound and a trimer of the aliphatic diisocyanate compound are preferable because they improve the moisture resistance and heat resistance of the coating film.
  • the trimer of the aliphatic diisocyanate compound include the above-mentioned aliphatic isocyanate-based isocyanurate-type polyisocyanates, and specific examples include hexamethylene diisocyanate and isophorone diisocyanate. These may be used alone or in a mixture.
  • the first reaction is charged in an equivalent relationship (B / (A + D)> 1: [NCO] / [OH] molar ratio) such that isocyanate groups remain after the reaction.
  • B / (A + D)> 1: [NCO] / [OH] molar ratio a large amount of unreacted polyisocyanate compound (B) is present, which may affect the flexibility of the ultraviolet curable adhesive composition.
  • the preparation ratio is reduced, the molecular weight increases and the curability of the ultraviolet curable adhesive composition may be affected.
  • the OH group of the alcohol compound (A + D) is 0.1 to 0.9 mol with respect to 1.0 mol of the NCO group of the polyisocyanate compound (B).
  • the first reaction can be carried out without a solvent, but in a solvent having a high viscosity of the product and having no alcoholic hydroxyl group for improving workability or in a polymerizable compound (F) described later. It is preferable to do so.
  • the solvent include ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone, aromatic hydrocarbons such as benzene, toluene, xylene, and tetramethylbenzene, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, and dipropylene glycol.
  • Glycol ethers such as dimethyl ether, dipropylene glycol diethyl ether, triethylene glycol dimethyl ether, triethylene glycol diethyl ether, ethyl acetate, butyl acetate, methyl cellosolve acetate, ethyl cellosolve acetate, butyl cellosolve acetate, carbitol acetate, propylene glycol monomethyl ether acetate , Propylene glycol monoethyl ether acetate, Propylene glycol monomethyl ether acetate, esters such as dialkyl glutarate, dialkyl succinate, dialkyl adipate, cyclic esters such as ⁇ -butyrolactone, petroleum solvents such as petroleum ether, petroleum naphtha, hydrogenated petroleum naphtha, solvent naphtha, etc. Can be carried out alone or in a mixed organic solvent.
  • the reaction temperature is usually in the range of 30 to 150 ° C, preferably 50 to 100 ° C.
  • the end point of the reaction is confirmed by a decrease in the amount of isocyanate.
  • a catalyst may be added for the purpose of shortening the reaction time.
  • this catalyst either a basic catalyst or an acidic catalyst is used.
  • the basic catalyst include amines such as pyridine, pyrrole, triethylamine, diethylamine, dibutylamine and ammonia, and phosphines such as tributylphosphine and triphenylphosphine.
  • acidic catalysts examples include copper naphthenate, cobalt naphthenate, zinc naphthenate, tributoxyaluminum, titanium tetraisopropoxide, zirconium tetrabutoxide, aluminum chloride, tin octylate, octyltin trilaurate, dibutyltin dilaurate, Mention may be made of Lewis acid catalysts such as octyltin diacetate. The amount of these catalysts added is usually 0.1 to 1 part by weight based on 100 parts by weight of the total weight of the diol compound (A + D) and the polyisocyanate compound (B).
  • the polyurethane compound (E) of the present invention is obtained by reacting (second reaction) a (meth) acrylate compound (C) having at least one hydroxyl group with respect to the remaining isocyanate group after the first reaction. be able to.
  • the (meth) acrylate compound (C) having at least one hydroxyl group used in the second reaction is a compound having at least one hydroxyl group and one (meth) acrylate in each molecule. Include 2-hydroxyethyl (meth) acrylate, propylene glycol mono (meth) acrylate, butanediol mono (meth) acrylate, pentanediol mono (meth) acrylate, hexanediol mono (meth) acrylate, diethylene glycol mono (meth) acrylate , Dipropylene glycol mono (meth) acrylate, triethylene glycol mono (meth) acrylate, tripropylene glycol mono (meth) acrylate, tetraethylene glycol mono (meth) acrylate, polyethylene glycol Dihydric alcohols such as mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, neopentyl glycol mono (meth)
  • the second reaction of the present invention is charged in an equivalent relationship such that the isocyanate group of the intermediate obtained after the first reaction is eliminated.
  • the OH group of the (meth) acrylate compound (C) having at least one hydroxyl group is 1.0 to 3.3 mol per 1.0 mol of the NCO group of the intermediate obtained after the first reaction.
  • the amount is 0 mol, more preferably 1.0 to 2.0 mol.
  • the second reaction can also be carried out in the absence of a solvent, but it is preferably carried out in the above-mentioned solvent and / or in the polymerizable compound (F) described later in order to improve the workability because the product has a high viscosity.
  • the reaction temperature is usually in the range of 30 to 150 ° C, preferably 50 to 100 ° C.
  • the end point of the reaction is confirmed by a decrease in the amount of isocyanate.
  • the aforementioned catalyst may be added for the purpose of shortening the reaction time.
  • a polymerization inhibitor such as 4-methoxyphenol is already added to the acrylate compound used as a raw material, but a polymerization inhibitor may be added again during the reaction.
  • examples of such polymerization inhibitors include hydroquinone, 4-methoxyphenol, 2,4-dimethyl-6-t-butylphenol, 2,6-di-t-butyl-4-cresol, 3-hydroxythiophenol, Examples include p-benzoquinone, 2,5-dihydroxy-p-benzoquinone, and phenothiazine. The amount used is 0.01 to 1% by weight based on the reaction raw material mixture.
  • the softener component (G) is used for the double-sided pressure-sensitive adhesive sheet for an image display device of the present invention.
  • Specific examples of the softener component that can be used include polymers or oligomers, phthalates, phosphates, glycol esters, citrates, aliphatic dibasic esters, fatty acid esters, epoxy plastics Agent, castor oil, terpene-based hydrogenated resin, terpene-based resin, the following general formula (1)
  • R 1 and R 2 may be the same or different.
  • R 1 and R 2 each have 1 to 18 alkyl groups, alkenyl groups having 1 to 18 carbon atoms, alkynyl groups having 1 to 18 carbon atoms, and aryl groups having 5 to 18 carbon atoms.
  • the oligomer and polymer include an oligomer or a polymer having a polyisoprene skeleton, a polybutadiene skeleton, a polybutene skeleton or a xylene skeleton and an esterified product thereof.
  • a polymer or an oligomer having a polybutadiene skeleton and an ester thereof are used. It is preferable to use a compound.
  • polystyrene resin examples include butadiene homopolymer, epoxy-modified polybutadiene, butadiene-styrene random copolymer, maleic acid-modified polybutadiene, and terminal hydroxyl group-modified liquid polybutadiene.
  • these softening agent components can be used in combination of two or more of the above components.
  • a solid softener component at room temperature (25 ° C.) because the sheet shape can be maintained while ensuring adhesion and low shrinkage.
  • the weight ratio of the softening agent component in the ultraviolet curable adhesive composition for obtaining the double-sided pressure-sensitive adhesive sheet for an image display device is usually 10 to 80% by weight, preferably 10 to 70% by weight.
  • an organic solvent is usually contained together with the (meth) acrylate (K) and the softening agent component (G).
  • an organic solvent which can be used, For example, alcohol, such as methanol, ethanol, isopropyl alcohol, dimethyl sulfone, dimethyl sulfoxide, tetrahydrofuran, a dioxane, toluene, xylene etc. are mentioned.
  • the double-sided pressure-sensitive adhesive sheet for an image display device of the present invention can contain a (meth) acrylate monomer as an optional component.
  • a (meth) acrylate monomer a (meth) acrylate having one (meth) acryloyl group in the molecule can be preferably used.
  • the (meth) acrylate monomer indicates (meth) acrylate excluding the urethane (meth) acrylate, the following epoxy (meth) acrylate, and the (meth) acrylate having the polyisoprene skeleton.
  • the (meth) acrylate having one (meth) acryloyl basis in the molecule include isooctyl (meth) acrylate, isoamyl (meth) acrylate, lauryl (meth) acrylate, isodecyl (meth) acrylate, stearyl ( Alkyl (meth) acrylates having 5 to 20 carbon atoms such as (meth) acrylate, cetyl (meth) acrylate, isomyristyl (meth) acrylate, tridecyl (meth) acrylate, etc.
  • alkyl (meth) acrylates preferably 10 carbon atoms from the viewpoint of volatility and solubility
  • alkyl (meth) acrylates more preferably 10 to 20 carbon atoms having a branched chain (meth) acrylate), benzyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, acryloylmorpholine, phenylglycine (Meth) acrylate, tricyclodecane (meth) acrylate, dicyclopentenyl acrylate, dicyclopentenyloxyethyl (meth) acrylate, isobornyl (meth) acrylate, dicyclopentanyl (meth) acrylate, 1-adamantyl acrylate, 2 -Having a cyclic skeleton such as methyl-2-adamantyl acrylate, 2-ethyl-2-adamantyl acrylate, 1-adamantyl methacrylate, polypropy
  • alkyl (meth) acrylates having 10 to 20 carbon atoms, 2-ethylhexyl carbitol acrylate, acryloylmorpholine, 4-hydroxybutyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, isostearyl (meth) acrylate, dicyclo Pentenyloxyethyl (meth) acrylate and polypropylene oxide-modified nonylphenyl (meth) acrylate are preferred.
  • alkyl (meth) acrylate having 10 to 20 carbon atoms, dicyclopentenyloxyethyl (meth) Preferred are acrylate, polypropylene oxide-modified nonylphenyl (meth) acrylate, and tetrahydrofurfuryl (meth) acrylate.
  • an alkyl (meth) acrylate having 1 to 5 carbon atoms having a hydroxyl group and acryloylmorpholine are preferable, and acryloylmorpholine is particularly preferable.
  • the (meth) acrylate monomer refers to (meth) acrylate excluding urethane (meth) acrylate, epoxy (meth) acrylate, and (meth) acrylate having a polyisoprene skeleton.
  • composition of the present invention can contain (meth) acrylates other than (meth) acrylate having one (meth) acryloyl group as long as the characteristics of the present invention are not impaired.
  • Trimethylol C2-C10 alkanes such as caprolactone-modified hydroxypivalic acid neopentyl glycol di (meth) acrylate and ethylene oxide-modified phosphoric acid di (meth) acrylate
  • Tri (meth) acrylate trimethylolpropane polyethoxytri (me
  • these (meth) acrylate monomer components can be used 1 type or in mixture of 2 or more types in arbitrary ratios.
  • the weight ratio of the (meth) acrylate monomer in the photocurable transparent adhesive composition of the present invention is usually 5 to 70% by weight, preferably 10 to 50% by weight. When it is less than 5% by weight, the curability is poor, and when it is more than 70% by weight, shrinkage increases.
  • (I) and (ii) are generally 25 to 90% by weight, 40 to 90% by weight, more preferably 40 to 80% by weight, based on the total amount of the resin composition.
  • epoxy (meth) acrylate can be used as long as the characteristics of the present invention are not impaired.
  • Epoxy (meth) acrylate has a function of improving curability and improving the hardness and curing speed of a cured product.
  • Epoxy (meth) acrylate is a general term for (meth) acrylate obtained by reacting an epoxy resin containing one or more functional epoxy groups with (meth) acrylic acid. (Meth) acrylic acid is reacted at a ratio of 0.9 to 1.5 mol, more preferably 0.95 to 1.1 mol, per 1 equivalent of epoxy group of the glycidyl ether type epoxy compound.
  • the reaction temperature is preferably 80 to 120 ° C., and the reaction time is about 10 to 35 hours.
  • a catalyst such as triphenylphosphine, TAP, triethanolamine, or tetraethylammonium chloride.
  • paramethoxyphenol, methylhydroquinone or the like can be used as a polymerization inhibitor.
  • epoxy resins used as raw materials for epoxy (meth) acrylates include phenyl diglycidyl ethers such as hydroquinone diglycidyl ether, catechol diglycidyl ether, resorcinol diglycidyl ether; bisphenol-A type epoxy resin, bisphenol-F type epoxy Bisphenol-type epoxy compounds such as resins, bisphenol-S type epoxy resins, 2,2-bis (4-hydroxyphenyl) -1,1,1,3,3,3-hexafluoropropane epoxy compounds; A type epoxy resin, hydrogenated bisphenol-F type epoxy resin, hydrogenated bisphenol-S type epoxy resin, hydrogenated 2,2-bis (4-hydroxyphenyl) -1,1,1,3,3,3-hexa Fluoropropane Epoxy Hydrogenated bisphenol-type epoxy compounds such as compounds; Halogenated bisphenol-type epoxy compounds such as brominated bisphenol-A type epoxy resins and brominated bisphenol-F type epoxy resins; Alicyclic diglycidyl such as cyclohex
  • An epoxy (meth) acrylate that can be suitably used in the present invention is a bisphenol A type epoxy (meth) acrylate obtained from a bisphenol A type epoxy compound.
  • the weight average molecular weight of the epoxy (meth) acrylate is preferably 500 to 10,000.
  • the weight ratio of the epoxy (meth) acrylate in the ultraviolet curable adhesive composition of the present invention is usually 1 to 80% by weight, preferably 5 to 30% by weight.
  • the content ratio of (meth) acrylate in the ultraviolet curable resin composition for obtaining the double-sided pressure-sensitive adhesive sheet for an image display device of the present invention is preferably 25 to 90% by weight, based on the total amount of the ultraviolet curable adhesive composition. Is 40 to 90% by weight, more preferably 40 to 80% by weight.
  • the (meth) acrylate at least one selected from the group consisting of the urethane (meth) acrylate, the (meth) acrylate having a polyisoprene skeleton, and the (meth) acrylate monomer
  • the urethane (meth) acrylate content is 20 to 80% by weight, preferably 30 to 70% by weight
  • the polyisoprene skeleton-containing (meth) acrylate content is 20 to 80% by weight. It is more preferable when the content ratio of the (meth) acrylate monomer is 5 to 70% by weight, preferably 10 to 50% by weight.
  • the urethane (meth) acrylate or the (meth) acrylate having a polyisoprene skeleton is contained as the (meth) acrylate, and the content ratio is 20 to 80% by weight, preferably 30 to More preferably, it is 70% by weight and contains a (meth) acrylate monomer, and its content is 5 to 70% by weight, preferably 10 to 50% by weight.
  • Examples of the (meth) acrylamide compound that can be used in the double-sided pressure-sensitive adhesive sheet for an image display device of the present invention include monofunctional (meth) acrylamides such as acryloylmorpholine and N-isopropyl (meth) acrylamide; methylenebis (meth) acrylamide And polyfunctional (meth) acrylamides.
  • the content is 25 to 90% by weight, preferably 40 to 90% by weight, more preferably 40 to 90% by weight, based on the total amount of the ultraviolet curable adhesive composition for obtaining a double-sided pressure-sensitive adhesive sheet for an image display device. 80% by weight.
  • an acyl phosphine oxide compound for example, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,4,6-trimethylbenzoylphenylethoxyphosphine oxide, bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide, bis (2, 6-dimethoxybenzoyl) -2,4,4-trimethyl-pentylphosphine oxide.
  • an uncured portion 2,4,6-trimethylbenzoyldiphenylphosphine oxide is particularly preferable from the viewpoint of the ease of formation of the resin and the transparency of the cured resin layer.
  • photopolymerization initiators include 1-hydroxycyclohexyl phenyl ketone (Irgacure 184; manufactured by BASF), 2-hydroxy-2-methyl- [4- (1-methylvinyl) phenyl] propanol oligomer (Esacure ONE; Lambarti 1- [4- (2-hydroxyethoxy) -phenyl] -2-hydroxy-2-methyl-1-propan-1-one (Irgacure 2959; manufactured by BASF), 2-hydroxy-1- ⁇ 4 -[4- (2-Hydroxy-2-methyl-propionyl) -benzyl] -phenyl ⁇ -2-methyl-propan-1-one (Irgacure 127; manufactured by BASF), 2,2-dimethoxy-2-phenylacetophenone (Irgacure 651; manufactured by BASF), 2-hydroxy-2-methyl-1-phenyl- Lopan-1-one (Darocur 1173; manufactured by BASF), 2-methyl-1- [4
  • an ⁇ -hydroxyketone polymer manufactured by ESACURE, KIP150 is used. It is preferable to use it.
  • these photopolymerization initiators can be used alone or in a mixture of two or more.
  • the weight ratio of the photopolymerization initiator in the photocurable resin composition for obtaining the double-sided pressure-sensitive adhesive sheet for an image display device of the present invention is usually 0.2 to 5% by weight, preferably 0.3 to 3% by weight. .
  • it is more than 5% by weight when obtaining a cured product layer having a cured part and an uncured part on the side opposite to the optical substrate side, the uncured part cannot be formed or the transparency of the resin cured product layer is low. There is a risk of getting worse.
  • accelerators such as tertiary amines such as triethanolamine and methyldiethanolamine, and benzoic acid derivatives such as N, N-dimethylaminobenzoic acid ethyl ester and N, N-dimethylaminobenzoic acid isoamyl ester. can do.
  • accelerators such as tertiary amines such as triethanolamine and methyldiethanolamine
  • benzoic acid derivatives such as N, N-dimethylaminobenzoic acid ethyl ester and N, N-dimethylaminobenzoic acid isoamyl ester.
  • an amount of 100% by weight or less is added to the photopolymerization initiator as necessary.
  • the double-sided pressure-sensitive adhesive sheet for an image display device of the present invention can contain, in addition to the (meth) acrylate and the photopolymerization initiator, the following photopolymerization initiation assistant, additives described below, and the like.
  • the content ratio of the other components with respect to the total amount of the ultraviolet curable adhesive composition of the present invention is a balance obtained by subtracting the total amount of the (meth) acrylate and the photopolymerization initiator from the total amount.
  • the total amount of the other components is 0 to 74% by weight, preferably 5 to 70% by weight, based on the total amount of the ultraviolet curable adhesive composition for obtaining the double-sided pressure-sensitive adhesive sheet for an image display device of the present invention. %.
  • amines that can serve as photopolymerization initiation assistants can be used in combination with the above photopolymerization initiator.
  • examples of amines that can be used include benzoic acid 2-dimethylaminoethyl ester, dimethylaminoacetophenone, p-dimethylaminobenzoic acid ethyl ester, and p-dimethylaminobenzoic acid isoamyl ester.
  • the content in the adhesive resin composition for obtaining the double-sided pressure-sensitive adhesive sheet for image display device of the present invention is usually 0.005 to 5% by weight, preferably 0.01 to 3% by weight.
  • the double-sided pressure-sensitive adhesive sheet for the image display device of the present invention includes an antioxidant, an organic solvent, a silane coupling agent, a polymerization inhibitor, a leveling agent, an antistatic agent, a surface lubricant, a fluorescent whitening agent, light as necessary. You may add additives, such as a stabilizer (for example, hindered amine compound etc.) and a filler.
  • a stabilizer for example, hindered amine compound etc.
  • antioxidants include, for example, BHT, 2,4-bis- (n-octylthio) -6- (4-hydroxy-3,5-di-t-butylanilino) -1,3,5-triazine Pentaerythrityl tetrakis [3- (3,5-di-t-butyl-4-hydroxyphenyl) propionate], 2,2-thio-diethylenebis [3- (3,5-di-t-butyl- 4-hydroxyphenyl) propionate], triethylene glycol-bis [3- (3-tert-butyl-5-methyl-4-hydroxyphenyl) propionate], 1,6-hexanediol-bis [3- (3-t -Butyl-5-methyl-4-hydroxyphenyl) propionate], octadecyl-3- (3,5-di-t-butyl-4-hydroxyphenyl) propionate, , N-hexamethylenebis (3,5-di-di
  • organic solvent examples include alcohols such as methanol, ethanol and isopropyl alcohol, dimethyl sulfone, dimethyl sulfoxide, tetrahydrofuran, dioxane, toluene, xylene and the like.
  • silane coupling agent examples include, for example, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (3,4-epoxy) (Cyclohexyl) ethyltrimethoxysilane, N- (2-aminoethyl) 3-aminopropylmethyldimethoxysilane, ⁇ -mercapropropyltrimethoxysilane, N- (2-aminoethyl) 3-aminopropylmethyltrimethoxysilane, 3 -Aminopropyltriethoxysilane, 3-mercaptopropyltrimethoxysilane, vinyltrimethoxysilane, N- (2- (vinylbenzylamino) ethyl) 3-aminopropyltrimethoxysilane hydrochloride, 3-methacryloxypropyltri
  • polymerization inhibitor examples include paramethoxyphenol and methylhydroquinone.
  • the light stabilizer include, for example, 1,2,2,6,6-pentamethyl-4-piperidyl alcohol, 2,2,6,6-tetramethyl-4-piperidyl alcohol, 1,2,2, 6,6-pentamethyl-4-piperidyl (meth) acrylate (LA-82, manufactured by ADEKA Corporation), tetrakis (1,2,2,6,6-pentamethyl-4-piperidyl) -1,2,3 4-butanetetracarboxylate, tetrakis (2,2,6,6-totramethyl-4-piperidyl) -1,2,3,4-butanetetracarboxylate, 1,2,3,4-butanetetracarboxylic acid and 1,2,2,6,6-pentamethyl-4-piperidinol and 3,9-bis (2-hydroxy-1,1-dimethylethyl) -2,4,8,10-tetraoxaspiro [5.5] Unde Mixed ester with decanoic acid bis (2,2,6,6-tetramethyl-4-
  • the filler include, for example, crystalline silica, fused silica, alumina, zircon, calcium silicate, calcium carbonate, silicon carbide, silicon nitride, boron nitride, zirconia, fosterite, steatite, spinel, titania, talc and the like.
  • examples thereof include powder or beads obtained by spheroidizing these.
  • the weight ratio of the various additives in the photocurable transparent adhesive composition for obtaining the double-sided pressure-sensitive adhesive sheet for an image display device is preferably 0.01 to 3% by weight. Is 0.01 to 1% by weight, more preferably 0.02 to 0.5% by weight.
  • the ultraviolet curable adhesive composition for obtaining the double-sided pressure-sensitive adhesive sheet for an image display device of the present invention can be obtained by mixing and dissolving each of the above-mentioned components at room temperature to 80 ° C. It may be removed by operation.
  • the adhesive resin composition of the present invention it is preferable to appropriately adjust the blending ratio of the components so that the viscosity at 25 ° C. is in the range of 300 to 15000 mPa ⁇ s in view of applicability.
  • the ultraviolet curable adhesive composition containing the (meth) acrylate (K) and the softening agent component (G) usually further contains the organic solvent.
  • the said ultraviolet curing adhesive composition is apply
  • An apparatus double-sided sheet can be obtained.
  • the drying conditions are not particularly limited as long as they are necessary for the solvent to be removed. Conditions for drying (about 1 to 60 minutes) can be used.
  • the sheet thus obtained is in the form in which no solvent is present or a small amount remains.
  • the residual solvent amount is preferably 5000 ppm or less, more preferably 1000 ppm or less, and particularly preferably 100 ppm or less.
  • the kind of release film is not particularly limited, but, for example, a PET film can be used.
  • the double-sided pressure-sensitive adhesive sheet for an image display device thus obtained has a structure in which the (meth) acrylate in the component is not crosslinked and polymerized, and the (meth) acryloyl group remains as it is and is laminated.
  • the double-sided pressure-sensitive adhesive sheet for an image display device of the present invention is preferably used for the purpose of producing a touch panel by attaching at least two optical substrates, at least one of which is an optical substrate having a light shielding part.
  • the curing shrinkage of the cured product of the double-sided pressure-sensitive adhesive sheet for an image display device of the present invention is preferably 3.0% or less, and particularly preferably 2.0% or less.
  • Step 1 the method for producing an optical member of the present invention.
  • Step 3 it is preferable that at least two optical substrates are bonded together by the following (Step 1) to (Step 3). If it is determined that sufficient adhesive strength can be secured at the stage of (Process 2), (Process 3) can be omitted.
  • Process 1 The process of peeling the single-sided release film of the double-sided adhesive sheet for image display apparatuses with a release film with respect to at least 1 optical base material, and arrange
  • a liquid crystal display unit is a liquid crystal display unit in which a liquid crystal material is sealed between a pair of substrates on which electrodes are formed, and a polarizing plate, a driving circuit, a signal input cable, and a backlight unit are provided.
  • the transparent substrate is a transparent substrate such as a glass plate, a polymethyl methacrylate (PMMA) plate, a polycarbonate (PC) plate, an alicyclic polyolefin polymer (COP) plate, an acrylic resin, or polyethylene terephthalate.
  • the transparent substrate may be subjected to hard coat treatment or antireflection treatment on one side or both sides.
  • a transparent substrate having a black frame-shaped light-shielding portion on the surface of the transparent substrate can be suitably used, and the light-shielding portion is formed by applying a tape, applying a paint, or printing.
  • the present invention can be applied to a device that does not have a light shielding portion.
  • a case where a light shielding portion is provided will be described as a specific example.
  • “transparent substrate” having the light-shielding part can be read as “transparent substrate”, which can be considered as an example of the case where the light-shielding part is not provided.
  • the optical member obtained by bonding the transparent substrate and the liquid crystal display unit is irradiated with ultraviolet rays from the side of the transparent substrate having the light-shielding portion to cure the double-sided pressure-sensitive adhesive sheet for image display devices.
  • the dose of ultraviolet rays is preferably about 100 ⁇ 4000mJ / cm 2 in accumulated light quantity, particularly preferably 200 ⁇ 3000mJ / cm 2 approximately.
  • the light source used for curing by irradiation with ultraviolet to near ultraviolet light may be any lamp as long as it is a lamp that emits ultraviolet to near ultraviolet light.
  • a low-pressure, high-pressure or ultrahigh-pressure mercury lamp, metal halide lamp, (pulse) xenon lamp, or electrodeless lamp can be used. In this way, an optical member can be obtained.
  • the transmittance at 400 nm to 800 nm of the cured product of the double-sided pressure-sensitive adhesive sheet for an image display device of the present invention is preferably 90% or more. This is because when the transmittance is less than 90%, it is difficult for light to pass therethrough and the visibility is lowered when used in a display device. Further, when the cured product has a high transmittance at 400 to 450 nm, the visibility can be further improved. Therefore, the transmittance at 400 to 450 nm is preferably 90% or more.
  • the double-sided pressure-sensitive adhesive sheet for an image display device of the present invention can be suitably used as an adhesive for producing an optical member by laminating a plurality of optical substrates.
  • the optical substrate used in the method for producing an optical member of the present invention include a transparent plate, a sheet, a touch panel, and a display unit.
  • the “optical substrate” means both an optical substrate having no light shielding part on the surface and an optical substrate having a light shielding part on the surface.
  • at least one of the plurality of optical base materials used is an optical base material having a light shielding portion. The position of the light shielding part in the optical substrate having the light shielding part is not particularly limited.
  • a band-shaped light shielding portion having a width of 0.05 to 20 mm, preferably about 0.05 to 10 mm, more preferably about 0.1 to 6 mm is formed in the peripheral portion of the optical substrate.
  • the light-shielding portion on the optical substrate can be formed by attaching a tape, applying a coating or printing.
  • Various materials can be used as the material of the optical substrate used in the present invention. Specifically, resins such as PET, PC, PMMA, a composite of PC and PMMA, glass, COC, COP, plastic (such as acrylic resin), and the like can be given.
  • an optical substrate used in the present invention for example, a transparent plate or sheet, a sheet or transparent plate obtained by laminating a plurality of films or sheets such as polarizing plates, a non-laminated sheet or transparent plate, and a transparent made from inorganic glass Plates (inorganic glass plates and processed products thereof, such as lenses, prisms, ITO glass) and the like can be used.
  • the optical substrate used in the present invention is a laminate composed of a plurality of functional plates or sheets (hereinafter referred to as “functional laminate”) such as a touch panel (touch panel input sensor) or the following display unit in addition to the polarizing plate described above. Also called “body”).
  • Examples of the sheet that can be used as the optical substrate used in the present invention include an icon sheet, a decorative sheet, and a protective sheet.
  • Examples of the plate (transparent plate) that can be used in the method for producing an optical member of the present invention include a decorative plate and a protective plate.
  • materials for these sheets or plates those listed as materials for transparent plates can be applied.
  • Examples of the material of the touch panel surface that can be used as the optical substrate used in the present invention include glass, PET, PC, PMMA, a composite of PC and PMMA, COC, and COP.
  • the thickness of a plate-like or sheet-like optical substrate such as a transparent plate or a sheet is not particularly limited, and is usually about 5 ⁇ m to 5 cm, preferably about 10 ⁇ m to 10 mm, more preferably about 50 ⁇ m to 3 mm. Is the thickness.
  • a plate-shaped or sheet-shaped transparent optical substrate having a light-shielding portion and the functional laminate are attached with a cured product of the ultraviolet curable adhesive composition for a touch panel of the present invention.
  • the combined optical member can be mentioned.
  • a display unit such as a liquid crystal display device as one of the optical substrates and using an optical functional material as the other optical substrate, a display unit with an optical functional material (hereinafter also referred to as a display panel). ) Can be manufactured.
  • the display unit include display devices such as LCD, EL display, EL illumination, electronic paper, and plasma display in which a polarizing plate is attached to glass.
  • the optical functional material include transparent plastic plates such as acrylic plates, PC plates, PET plates, and PEN plates, tempered glass, and touch panel input sensors.
  • the refractive index of the cured product is 1.45 to 1.55 in order to improve the visibility because the visibility of the display image is further improved.
  • the difference in refractive index from the base material used as the optical base material can be reduced, and the light loss can be reduced by suppressing the irregular reflection of light.
  • the optical member including the display unit knit obtained by the manufacturing method of the present invention and the optical base material having the light shielding portion can be incorporated into an electronic device such as a television, a small game machine, a mobile phone, and a personal computer.
  • the double-sided pressure-sensitive adhesive sheet for an image display device of the present invention is excellent in flexibility, has high moisture resistance, heat resistance, and light resistance, and fills an air gap in a display device such as a liquid crystal display device, an organic EL display device, or a touch panel image display device It is useful for applications such as agents.
  • toluene 208 g was charged and stirred until uniform, and the internal temperature was adjusted to 50 ° C. Subsequently, 61.35 g (0.28 mol) of isophorone diisocyanate was added as a polyisocyanate compound and reacted at 80 ° C. until the target NCO content was reached. Next, 0.37 g of 4-methoxyphenol as a polymerization inhibitor was added and stirred until uniform, and 2-hydroxyethyl produced by Osaka Organic Chemical Co., Ltd. as a (meth) acrylate compound having at least one hydroxyl group.
  • toluene 73.4 g was charged and stirred until uniform, and the internal temperature was adjusted to 50 ° C.
  • 88.9 g (0.40 mol) of isophorone diisocyanate was added as a polyisocyanate compound and reacted at 80 ° C. until the target NCO content was reached.
  • 0.37 g of 4-methoxyphenol as a polymerization inhibitor was added and stirred until uniform, and 2-hydroxyethyl produced by Osaka Organic Chemical Co., Ltd. as a (meth) acrylate compound having at least one hydroxyl group.
  • Example 1 109 parts of E-1 (polyurethane compound) of Synthesis Example 1, 18 parts of Clearon TO-125 (aromatic modified terpene resin) manufactured by Yashara Chemical Co., Ltd., 5 parts of KIP150 ( ⁇ -hydroxyketone polymer) manufactured by ESACURE 40 parts of toluene Were mixed and dissolved to obtain a resin composition.
  • the resulting resin composition is applied to a comma coater so that the thickness of the resin composition layer after drying is 100 ⁇ m on the release-treated surface of a PET film (thickness 50 ⁇ m) treated with a silicon release agent. And uniformly dried at 120 ° C. for 3 minutes. After drying, the release treatment surface of the PET film treated with the silicon mold release agent is bonded onto the resin composition layer, and the composition of the present invention (configuration: release) Mold-treated PET / resin composition layer / release-treated PET) resin composition sheet was obtained.
  • Example 2 100 parts of Synthesis Example 1 E-1 (polyurethane compound), 2 parts of Bremer LA (lauryl acrylate) manufactured by NOF Corporation, 18 parts of Clearon M-105 (aromatic modified hydrogenated terpene resin) manufactured by Yashara Chemical Co., Ltd. Nippon Soda Co., Ltd. GI-2000 (1,2-hydrogenated polybutadiene glycol) 5 parts, LAMBSON speed cure TPO (2,4,6-trimethylbenzoyldiphenylphosphine oxide) 0.4 parts, ESACURE KIP150 ( A resin composition was obtained by mixing and dissolving 2 parts of toluene with 2 parts of an ⁇ -hydroxyketone polymer. The obtained resin composition was applied and dried in the same manner as in Example 1 to obtain a resin composition sheet.
  • Example 3 100 parts of Synthesis Example 1 E-1 (polyurethane compound), 2 parts of Bremer LA (lauryl acrylate) manufactured by NOF Corporation, 18 parts of Clearon M-105 (aromatic modified hydrogenated terpene resin) manufactured by Yashara Chemical Co., Ltd. JX Nippon Mining & Energy Co., Ltd. (polybutene) 5 parts, LAMBSON speed cure TPO (2,4,6-trimethylbenzoyldiphenylphosphine oxide) 0.4 parts, ESACURE KIP150 ( ⁇ -hydroxyketone polymer) Two parts of 42 parts of toluene were mixed and dissolved to obtain a resin composition. The obtained resin composition was applied and dried in the same manner as in Example 1 to obtain a resin composition sheet.
  • Example 4 67 parts of E-1 (polyurethane compound) in Synthesis Example 1, 28 parts of E-2 (Polyurethane Compound) in Synthesis Example 2, 2 parts of Bremer LA (lauryl acrylate) manufactured by NOF Corporation, Clearon M manufactured by Yashara Chemical Co., Ltd. -105 (Aromatically modified hydrogenated terpene resin) 18 parts, Nippon Soda Co., Ltd.
  • GI-2000 (1,2-hydrogenated polybutadiene glycol) 5 parts, LAMBSON speed cure TPO (2,4,6-trimethylbenzoyl) Diphenylphosphine oxide) 0.4 part and ESACURE 2 parts KIP150 ( ⁇ -hydroxyketone polymer) 47 parts toluene were mixed and dissolved to obtain a resin composition.
  • the obtained resin composition was applied and dried in the same manner as in Example 1 to obtain a resin composition sheet.
  • Examples 1 to 4 are shown in Table 1 and evaluated as follows.
  • the resin composition sheet of the present invention was irradiated with ultraviolet rays having an integrated light amount of 3000 mJ / cm 2 with a high-pressure mercury lamp (120 W / cm, ozone-less) through a release-treated PET to cure the resin composition layer.
  • the refractive index (20 ° C.) of the cured resin layer was measured with RX-7000CX (manufactured by ATAGO).
  • the resin composition sheet of the present invention was irradiated with ultraviolet rays having an integrated light amount of 3000 mJ / cm 2 with a high-pressure mercury lamp (120 W / cm, ozone-less) through a release-treated PET to cure the resin composition layer.
  • the rigidity (30 ° C.) of the cured resin layer was measured with ARES (TA Instruments).
  • the release treatment PET of the resin composition sheet of the present invention was peeled off and bonded to a glass plate having a thickness of 1 mm (configuration: 1 mm glass plate / resin composition layer / 1 mm glass plate) to prepare a test piece.
  • the resin composition layer was cured by irradiating the prepared test piece with ultraviolet rays through a glass with a high-pressure mercury lamp (120 W / cm, ozone-less) with an integrated light amount of 3000 mJ / cm 2.
  • the transmittance of the obtained resin cured test piece was measured with a spectrophotometer UV-3600 (manufactured by Shimadzu Corporation). As a result, the transmittance at 380 nm to 780 nm was 95% or more.
  • the release treatment PET of the resin composition sheet of the present invention was peeled off and bonded to a glass plate having a thickness of 1 mm (configuration: 1 mm glass plate / resin composition layer / 1 mm glass plate) to prepare a test piece.
  • the resin composition layer was cured by irradiating the prepared test piece with ultraviolet rays having a cumulative light amount of 3000 mJ / cm 2 through a glass with a high-pressure mercury lamp (120 W / cm, ozone-less).
  • the haze value of the obtained resin cured test piece was measured with a haze meter TC-HIIIDPK (manufactured by Tokyo Denshoku). As a result, the haze value was 0.5 or less and it was transparent.
  • the release-treated PET on one side of the resin composition sheet of the present invention was peeled off, bonded to a 100 ⁇ m COP film (manufactured by Nippon Zeon Co., Ltd.), and cut into a 25 mm width strip. Half of the cut strip-shaped film is peeled off from the other release-treated PET, and bonded to a glass plate. From the glass plate side, UV light with an integrated light intensity of 3000 mJ / cm 2 is irradiated with a high-pressure mercury lamp (120 W / cm, ozone-less) The composition layer was cured. The obtained resin cured test pieces were subjected to an adhesion test (180 ° peeling, peeling speed 300 mm / min) using EZ-Test (manufactured by Shimadzu Corporation).
  • the release treatment PET of the resin composition sheet of the present invention is peeled off and bonded to a glass plate having a thickness of 1 mm (configuration 1: 1 mm glass plate / resin composition layer / 1 mm glass plate) (configuration 2: 1 mm glass plate / resin).
  • Composition layer / polarizing film / acrylic adhesive layer / 1 mm glass plate) A test piece was prepared.
  • the resin composition layer was cured by irradiating the prepared test piece with ultraviolet rays having a cumulative light amount of 3000 mJ / cm 2 through a glass with a high-pressure mercury lamp (120 W / cm, ozone-less). Using the obtained resin cured test piece, an 85 ° C.
  • the double-sided pressure-sensitive adhesive sheet for image display device of the present invention has high transmittance, low haze value, and excellent adhesion, heat resistance, and moist heat resistance.
  • the double-sided pressure-sensitive adhesive sheet for an image display device of the present invention is useful as an optical application member because of its high transparency and excellent adhesion and durability. Furthermore, the resin composition sheet of the present invention is useful as an adhesive for bonding a transparent display substrate.

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  • Macromonomer-Based Addition Polymer (AREA)

Abstract

　L'invention concerne une feuille adhésive double face pour des dispositifs d'affichage d'images, ladite feuille adhésive étant aisément productible et provoquant un endommagement minimal de matériaux de base optiques, permettant d'obtenir des éléments optiques tels que des unités d'affichage ayant de bonnes aptitude au durcissement et adhésivité et permettant d'obtenir des éléments optiques (écrans tactiles) ayant une adhésivité et une résistance d'adhérence élevées par rapport à des matériaux de base. Ladite feuille adhésive comprend : un constituant plastifiant (G) et un (méth)acrylate (K) comprenant au moins un composé choisi dans le groupe constitué par un uréthane-(méth)acrylate, un (méth)acrylate ayant un squelette polyisoprène et un (méth)acrylate ayant un squelette de butadiène.
PCT/JP2015/066885 2014-06-11 2015-06-11 Feuille adhésive double face pour dispositifs d'affichage d'images et article correspondant WO2015190558A1 (fr)

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JP2014-120621 2014-06-11
JP2014120621 2014-06-11
JP2015-112948 2015-06-03
JP2015112948A JP2016222861A (ja) 2015-06-03 2015-06-03 画像表示装置用両面粘着シート及び物品

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CN108473827A (zh) * 2016-02-02 2018-08-31 阪东化学株式会社 光学透明粘着片、光学透明粘着片的制造方法、层叠体及带触摸屏的显示装置
CN109071695A (zh) * 2016-03-31 2018-12-21 哈利玛化成株式会社 固化性组合物、保形涂布剂和固化物
US11447662B2 (en) 2015-11-26 2022-09-20 Bando Chemical Industries, Ltd. Optical transparent adhesive sheet, method for producing optical transparent adhesive sheet, laminated body, and display device with touch panel
US11466185B2 (en) 2015-05-08 2022-10-11 Bando Chemical Industries, Ltd. Optical transparent adhesive sheet, method for producing optical transparent adhesive sheet, laminate and display device with touch panel
US11530337B2 (en) 2015-09-29 2022-12-20 Bando Chemical Industries, Ltd. Optically transparent pressure-sensitive adhesive sheet, laminate, process for producing laminate, and display device with touch panel

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CN108977102B (zh) * 2017-06-01 2021-03-09 株式会社有泽制作所 双面粘接片材、3d液晶面板及其制造方法

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JP2014065790A (ja) * 2012-09-25 2014-04-17 Nippon Shokubai Co Ltd 表示装置用紫外線硬化型樹脂組成物、硬化物及び表示装置

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JP5701892B2 (ja) * 2010-10-01 2015-04-15 昭和電工株式会社 光硬化性透明粘着シート用組成物
JP5952013B2 (ja) * 2011-03-23 2016-07-13 三菱樹脂株式会社 画像表示装置用透明両面粘着シートおよび画像表示装置
JP6104244B2 (ja) * 2012-06-15 2017-03-29 昭和電工株式会社 重合性組成物、重合物、光学用粘着シート、画像表示装置およびその製造方法

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JP2013196551A (ja) * 2012-03-22 2013-09-30 Toray Advanced Film Co Ltd タッチパネル用粘着シート、タッチパネルおよび表示装置
JP2014065790A (ja) * 2012-09-25 2014-04-17 Nippon Shokubai Co Ltd 表示装置用紫外線硬化型樹脂組成物、硬化物及び表示装置

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Publication number Priority date Publication date Assignee Title
US11466185B2 (en) 2015-05-08 2022-10-11 Bando Chemical Industries, Ltd. Optical transparent adhesive sheet, method for producing optical transparent adhesive sheet, laminate and display device with touch panel
US11530337B2 (en) 2015-09-29 2022-12-20 Bando Chemical Industries, Ltd. Optically transparent pressure-sensitive adhesive sheet, laminate, process for producing laminate, and display device with touch panel
US11447662B2 (en) 2015-11-26 2022-09-20 Bando Chemical Industries, Ltd. Optical transparent adhesive sheet, method for producing optical transparent adhesive sheet, laminated body, and display device with touch panel
CN108473827A (zh) * 2016-02-02 2018-08-31 阪东化学株式会社 光学透明粘着片、光学透明粘着片的制造方法、层叠体及带触摸屏的显示装置
EP3412740A4 (fr) * 2016-02-02 2019-09-25 Bando Chemical Industries, Ltd. Feuille adhésive transparente optique, procédé de production d'une feuille adhésive transparente optique, stratifié, et dispositif d'affichage doté d'un panneau tactile
CN109071695A (zh) * 2016-03-31 2018-12-21 哈利玛化成株式会社 固化性组合物、保形涂布剂和固化物
CN109071695B (zh) * 2016-03-31 2021-03-26 哈利玛化成株式会社 固化性组合物、保形涂布剂和固化物

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