WO2012035958A1 - Composition photodurcissable pour utilisation dans une feuille adhésive autocollante transparente - Google Patents

Composition photodurcissable pour utilisation dans une feuille adhésive autocollante transparente Download PDF

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Publication number
WO2012035958A1
WO2012035958A1 PCT/JP2011/069288 JP2011069288W WO2012035958A1 WO 2012035958 A1 WO2012035958 A1 WO 2012035958A1 JP 2011069288 W JP2011069288 W JP 2011069288W WO 2012035958 A1 WO2012035958 A1 WO 2012035958A1
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meth
adhesive sheet
composition
acrylate
transparent
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PCT/JP2011/069288
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English (en)
Japanese (ja)
Inventor
中西　健一
篤 海野
一博 佐々木
雄太 竹内
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昭和電工株式会社
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Priority to KR1020137009611A priority Critical patent/KR101494984B1/ko
Priority to JP2012533934A priority patent/JP5854404B2/ja
Priority to CN201180044682.0A priority patent/CN103108930B/zh
Publication of WO2012035958A1 publication Critical patent/WO2012035958A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/04—Homopolymers or copolymers of ethene
    • C08L23/08—Copolymers of ethene
    • C08L23/0846—Copolymers of ethene with unsaturated hydrocarbons containing other atoms than carbon or hydrogen atoms
    • C08L23/0869—Acids or derivatives thereof
    • 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
    • C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
    • C09J123/02—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers not modified by chemical after-treatment
    • 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
    • B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
    • B32B27/308—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers comprising acrylic (co)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
    • B32B27/36—Layered products comprising a layer of synthetic resin comprising polyesters
    • 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
    • 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
    • C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
    • 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
    • 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
    • B32B2250/00—Layers arrangement
    • B32B2250/02—2 layers
    • 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
    • B32B2250/00—Layers arrangement
    • B32B2250/24—All layers being polymeric
    • 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
    • B32B2255/00—Coating on the layer surface
    • B32B2255/10—Coating on the layer surface on synthetic resin layer or on natural or synthetic rubber layer
    • 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
    • B32B2255/00—Coating on the layer surface
    • B32B2255/20—Inorganic coating
    • 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
    • B32B2270/00—Resin or rubber layer containing a blend of at least two different 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
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/20—Properties of the layers or laminate having particular electrical or magnetic properties, e.g. piezoelectric
    • B32B2307/202—Conductive
    • 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
    • B32B2307/00—Properties of the layers or laminate
    • B32B2307/40—Properties of the layers or laminate having particular optical properties
    • B32B2307/412—Transparent
    • 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
    • B32B2457/00—Electrical equipment
    • B32B2457/20—Displays, e.g. liquid crystal displays, plasma displays
    • B32B2457/208—Touch screens

Definitions

  • the present invention is characterized in that a photocurable transparent adhesive sheet obtained by curing a composition for a photocurable transparent adhesive sheet and a composition for a photocurable transparent adhesive sheet is used for laminating a transparent conductive film.
  • a transparent adhesive sheet for fixing a transparent conductive film, a transparent adhesive sheet for fixing a transparent conductive film, and a transparent adhesive sheet for fixing a transparent conductive film obtained by curing a composition for transparent adhesive sheet for fixing a transparent conductive film are transparent.
  • the present invention relates to a laminate that is bonded to a conductive layer surface of a conductive film.
  • the touch panel is a transparent base material for transparent optical substrates such as ITO (Indium Tin Oxide) and a transparent substrate, glass and a transparent protective sheet for protecting it, and a display device such as a liquid crystal display. It is the laminated body bonded together using the sheet
  • transparent optical substrates such as ITO (Indium Tin Oxide)
  • a display device such as a liquid crystal display. It is the laminated body bonded together using the sheet
  • touch panels There are two types of touch panels: a resistive touch panel that detects mainly the pressure at the time of input, and a capacitive touch panel that detects the input location by static electricity from the human body at the time of input.
  • the capacitive touch panel the conductive layer surface of the transparent conductive film is fixed so as to be in contact with the pressure-sensitive adhesive layer surface of the pressure-sensitive adhesive sheet. Therefore, there is a problem that when the pressure-sensitive adhesive layer is in contact with the conductive layer surface of the transparent conductive film, a metal oxidation reaction occurs due to the acid component contained in the pressure-sensitive adhesive, resulting in a decrease in the conductive function. For this reason, the adhesive sheet for fixing a transparent conductive film is required to have high metal corrosion prevention properties.
  • a pressure-sensitive adhesive sheet having metal corrosion prevention properties As a pressure-sensitive adhesive sheet having metal corrosion prevention properties, a pressure-sensitive adhesive sheet containing a metal corrosion inhibitor (for example, Patent Document 1) has been proposed. Moreover, the adhesive sheet (for example, patent document 2) which reduced the corrosivity with respect to a transparent conductive film by containing a specific amount of nitrogen atom containing components with respect to the acid component of an adhesive layer is proposed.
  • the pressure-sensitive adhesive sheet containing a metal corrosion inhibitor has a problem that the metal corrosion inhibitor is discolored in a durability test and optical properties are deteriorated.
  • the pressure-sensitive adhesive sheet containing a specific amount of a nitrogen atom-containing component has a problem that an increase in the electrical resistance value of ITO cannot be sufficiently suppressed due to the acid component contained in the pressure-sensitive adhesive layer.
  • the problem to be solved by the present invention is that the transparent adhesive sheet obtained by curing does not corrode the conductive layer even if it is directly bonded to the conductive layer surface of the transparent conductive film, and the cohesive force and transparency of the adhesive layer And it is providing the composition for photocurable transparent adhesive sheets which is excellent in punching workability. Furthermore, it is in providing this transparent adhesive sheet.
  • composition for sheets Comprising: The composition for photocurable transparent adhesive sheets whose carboxyl group monomer contained in a photopolymerizable monomer is below a predetermined amount is the composition for photocurable transparent adhesive sheets. It discovered that the transparency of the photocurable transparent adhesive sheet obtained by making it harden
  • the present invention is shown by the following (1) to (11).
  • the photopolymerizable monomer other than the (meth) acrylic acid ester having a hydroxyl group is a monofunctional alkyl (meth) acrylate and / or a cyclic alkyl (meth) acrylate.
  • a (meth) acryl group-containing polyolefin compound having a weight average molecular weight of 10,000 to 300,000 is a polyolefin polyol compound, a (meth) acrylate having a hydroxyl group, and two isocyanate groups in one molecule.
  • composition for a photocurable transparent adhesive sheet according to any one of (1) to (6) above, wherein the acid value is 0.5 mgKOH / g or less.
  • a photocurable transparent adhesive sheet obtained by curing the composition for a photocurable transparent adhesive sheet according to any one of (1) to (7) above is used for laminating a transparent conductive film.
  • a transparent adhesive sheet for fixing a transparent conductive film obtained by curing the composition for transparent adhesive sheet for fixing a transparent conductive film according to (8) above.
  • (11) A laminate characterized in that the transparent conductive sheet fixing transparent adhesive sheet according to (9) or (10) is adhered to a conductive layer surface of a transparent conductive film.
  • the composition for a photocurable transparent pressure-sensitive adhesive sheet of the present invention contains a high molecular weight (meth) acrylic group-containing polyolefin compound in the composition, and therefore is excellent in flexibility and moisture permeability of a pressure-sensitive adhesive sheet obtained by curing. Furthermore, since the composition contains only a small amount of carboxyl groups, corrosion of the conductive layer surface of the transparent conductive film due to the acid component of the transparent adhesive sheet obtained can be suppressed, and the composition has a hydroxyl group (meta) Since acrylic acid ester is contained, the cohesive force of the obtained adhesive sheet and the adhesiveness to a base material are excellent.
  • composition for a photocurable transparent adhesive sheet of the present invention comprises (A) a (meth) acrylic group-containing polyolefin compound having a weight average molecular weight of 10,000 to 300,000, and (B) a (meth) acrylic acid ester having a hydroxyl group. (C) A photopolymerizable monomer other than (meth) acrylic acid ester having a hydroxyl group, and (D) a photopolymerization initiator.
  • any polyolefin compound having a polyolefin skeleton and having a (meth) acryl group introduced therein can be used.
  • the polyolefin skeleton include polyethylene, polypropylene, ethylene / propylene copolymer, butadiene, isoprene, hydrogenated polybutadiene, hydrogenated polyisoprene, cycloolefin, and the like. Hydrogenated polybutadiene and hydrogenated polyisoprene skeleton are preferable in terms of light resistance, transparency (non-crystalline), and workability (liquid).
  • the (meth) acryl group means CH 2 ⁇ CH—CO— or CH 2 ⁇ C (CH 3 ) —CO—.
  • the method for introducing the (meth) acrylic group into the polyolefin is not particularly limited, but the polyolefin having a reactive hydroxyl group at the molecular end or the like is esterified with (meth) acrylic acid,
  • Examples of the method include (meth) acrylation by adding an isocyanate compound having two or more isocyanate groups in one molecule to a hydroxyl group of polyolefin and reacting the (meth) acrylate having an isocyanate group and a hydroxyl group.
  • (meth) acrylic group-containing polyolefin obtained by reacting a polyolefin polyol compound with an isocyanate compound having two or more isocyanate groups in one molecule and then urethanizing a (meth) acrylate having a hydroxyl group.
  • a compound is preferable at the point with the high cohesion force of the adhesive sheet obtained.
  • the polyolefin polyol compound has two or more hydroxyl groups in one molecule, but preferably has 2 to 4 hydroxyl groups. Further, the weight average molecular weight of the polyolefin polyol compound is preferably 5,000 to 30,000, more preferably 10,000 to 15,000. When the weight average molecular weight of the polyolefin polyol compound is lower than 5,000, the molecular weight of the resulting (meth) acryl group-containing polyolefin compound does not increase, and sufficient strength of the pressure-sensitive adhesive sheet tends not to be obtained. Moreover, when the weight average molecular weight of the polyolefin polyol compound is higher than 30,000, the molecular weight of the resulting (meth) acrylic group-containing polyolefin compound becomes too high and the handling tends to be difficult.
  • Examples of the compound having two or more isocyanate groups in one molecule include tolylene diisocyanate, xylylene diisocyanate, diphenylmethane diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, tetramethylxylylene diisocyanate, isophorone diisocyanate and hydrogenation thereof. And diisocyanate compounds such as products. Of these, isophorone diisocyanate is preferable from the viewpoint of light resistance and ease of reactivity control. These compounds having two or more isocyanate groups in one molecule can be used alone or in combination of two or more.
  • the amount of the isocyanate compound having two or more isocyanate groups in one molecule is preferably 8 to 35 parts by mass, more preferably 10 to 30 parts by mass with respect to 100 parts by mass of the polyolefin polyol. More preferably, it is 11 to 25 parts by mass. If the amount of the isocyanate compound having two or more isocyanate groups in one molecule is less than 8 parts by mass, the resulting (meth) acrylic group-containing polyolefin compound becomes too high in molecular weight, making it difficult to handle. When the amount exceeds 35 parts by mass, the molecular weight of the resulting (meth) acrylic group-containing polyolefin compound becomes too low, so that the strength of the pressure-sensitive adhesive sheet tends to be insufficient.
  • Examples of the (meth) acrylate having a hydroxyl group to be reacted with an isocyanate group include hydroxyalkyl (meth) acrylate having an alkyl group having 2 to 7 carbon atoms, and specific examples thereof include 2- Hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 1,3-butanediol (meth) acrylate, 1,4-butanediol (meth) acrylate, 1,6 -Hexanediol (meth) acrylate, 3-methylpentanediol (meth) acrylate, etc.
  • the amount of the (meth) acrylate having a hydroxyl group is preferably 3 to 18 parts by mass, more preferably 4 to 15 parts by mass with respect to 100 parts by mass of the polyolefin polyol. More preferably.
  • the amount of the (meth) acrylate having a hydroxyl group is less than 3 parts by mass, there may be an olefin compound having no (meth) acryl group, and the strength of the pressure-sensitive adhesive sheet is lowered, and the hydroxyl group is )
  • the amount of acrylate used exceeds 18 parts by mass, the pressure-sensitive adhesive sheet tends to be hardened because the amount of (meth) acrylic groups introduced into the olefin is too large.
  • the number of (meth) acrylic groups introduced in the (A) (meth) acrylic group-containing polyolefin compound of the present invention may be one or more (meth) acrylic groups per molecule, preferably 1 to 1 per molecule. Two.
  • the molecular weight of the (meth) acryl group-containing polyolefin compound is preferably 10,000 to 300,000, more preferably 20,000 to 200,000, and even more preferably 30,000 to 100,000. is there.
  • the weight average molecular weight is less than 10,000, the cohesive force of the obtained pressure-sensitive adhesive sheet is low, and thus the strength of the pressure-sensitive adhesive sheet may not be sufficient, which is not preferable.
  • the molecular weight is larger than 300,000, the viscosity of the photocurable transparent pressure-sensitive adhesive sheet composition becomes too high, and handling becomes difficult and workability is remarkably deteriorated.
  • the weight average molecular weight in the present invention is a value obtained by using a standard polystyrene calibration curve, measured at normal temperature under the following conditions using gel permeation chromatography (Shodex GPC-101 manufactured by Showa Denko KK). is there. Column: Showa Denko LF-804 Column temperature: 40 ° C Sample: 0.2 mass% copolymer solution in tetrahydrofuran Flow rate: 1 ml / min Eluent: Tetrahydrofuran detector: RI
  • the content of the (meth) acrylic group-containing polyolefin compound in the photocurable transparent adhesive sheet composition is preferably 10 to 50% by mass, and preferably 15 to 45% by mass in the composition. Is more preferable, and 20 to 40% by mass is even more preferable.
  • the content is less than 10% by mass, the resulting pressure-sensitive adhesive sheet becomes brittle, which is not preferable.
  • the amount is more than 50% by mass, the adhesive strength of the resulting adhesive sheet may be lowered, which is not preferable.
  • the (meth) acrylic acid ester having a hydroxyl group mentioned here preferably has no carboxyl group, and examples thereof include hydroxyalkyl (meth) acrylates having an alkyl group with 2 to 7 carbon atoms.
  • 2-hydroxyethyl (meth) acrylate 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 1,3-butanediol (meth) acrylate, and 1,4-butanediol (Meth) acrylate, 1,6-hexanediol (meth) acrylate, 3-methylpentanediol (meth) acrylate and the like can be exemplified, and these can be used alone or in combination of two or more.
  • 2-hydroxyethyl acrylate is preferable from the viewpoint of the adhesive strength of the obtained adhesive sheet.
  • the content of the (B) hydroxyl group-containing (meth) acrylic acid ester is preferably 1 to 30% by mass, more preferably 5 to 25% by mass, in the photocurable transparent adhesive sheet composition. More preferably, it is 10 to 20% by mass. If it is less than 1% by mass, the adhesiveness of the obtained pressure-sensitive adhesive sheet to the substrate is insufficient, which is not preferable. Moreover, when more than 30 mass%, the water resistance of an adhesive sheet worsens and is unpreferable.
  • a photopolymerizable monomer other than the (meth) acrylic acid ester having a hydroxyl group (hereinafter sometimes referred to as “(C) photopolymerizable monomer”) is a photopolymerizable monomer. Further, it refers to other than (meth) acrylic acid ester having a hydroxyl group, and a monomer not containing a carboxyl group (chemical formula: —COOH) is preferable.
  • the monomer is not particularly limited, and a monofunctional or polyfunctional photopolymerizable monomer having a vinyl group, a (meth) acryl group, or the like can be used alone or in combination of two or more.
  • a (meth) acrylate compound having a (meth) acryl group is preferable.
  • Alkoxyalkyl (meth) acrylates such as ethoxyethyl (meth) acrylate, methoxyethyl (meth) acrylate, butoxyethyl (meth) acrylate, 2-methoxyethoxyethyl (meth) acrylate, 2-ethoxyethoxyethyl (meth) acrylate, methoxy Fluorinated alkyl (meth) acrylates such as alkoxy (poly) alkylene glycol (meth) acrylates such as diethylene glycol (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, methoxydipropylene glycol (meth) acrylate, and octafluoropentyl (meth) acrylate , N, N-dimethylaminoethyl (meth) acrylate, N, N-diethylaminoethyl (meth) acrylate, etc.
  • (Meth) acrylate polyethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, hydroxypivalin Acid ester neopentyl glycol di (meth) acrylate, 1,3-bis (hydroxyethyl) -5,5-dimethylhydantoin di (meth) acrylate, ⁇ , ⁇ -di (meth) acrylbisdiethylene glycol phthalate, trimethylolpropane tri (Meth) acrylate, trimethylolpropane tri (meth) acrylate, ethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, poly Tylene glycol di (meth) acrylate, 1,4-butanediol di (meth)
  • Epoxy group-containing (meth) acrylate and the like Epoxy group-containing (meth) acrylate and the like.
  • the photopolymerizable monomer (C) of the present invention from the viewpoint of miscibility with the (meth) acrylic group-containing polyolefin compound, adhesiveness of the adhesive sheet, strength, light resistance, and heat resistance, monofunctional alkyl ( A (meth) acrylate or a cyclic alkyl (meth) acrylate is preferred.
  • the monofunctional or polyfunctional functional group here refers to a (meth) acrylic group.
  • the content of the photopolymerizable monomer (C) is preferably 20 to 88% by mass, more preferably 20 to 70% by mass in the photocurable transparent adhesive sheet composition. More preferably, it is 40 to 69% by mass.
  • the adhesiveness of the obtained pressure-sensitive adhesive sheet to the substrate is insufficient, which is not preferable. Moreover, when more than 88 mass%, since the cohesion force of an adhesive sheet becomes low, an adhesive force becomes low and is unpreferable.
  • the carboxyl group-containing monomer such as acrylic acid or methacrylic acid contained in the photopolymerizable monomer (C) is 0.1% relative to the total amount of the photopolymerizable monomer (C). It is less than or equal to mass%, more preferably less than or equal to 0.05 mass%. More preferably, the photopolymerizable monomer (C) does not contain a carboxyl group-containing monomer. When the carboxyl group-containing monomer exceeds 0.1% by mass with respect to the total amount of the photopolymerizable monomer (C), it becomes difficult to suppress corrosion of the conductive layer surface of the transparent conductive film.
  • the theoretical glass transition temperature of the polymer comprising the (B) hydroxyl group-containing (meth) acrylic acid ester of the present invention and the photopolymerizable monomer (C) is 0 to 0 from the viewpoint of the strength and adhesive strength of the pressure-sensitive adhesive sheet. It is preferably 50 ° C., more preferably 5 to 45 ° C., and further preferably 10 to 40 ° C. When the temperature is lower than 0 ° C., the resulting pressure-sensitive adhesive sheet becomes too soft due to the influence of the (meth) acrylic group-containing polyolefin compound, so that the adhesive strength of the pressure-sensitive adhesive sheet is lowered, which is not preferable.
  • the theoretical glass transition temperature (Tg) is the following fox (FOX) based on the Tg of the homopolymer (homopolymer) of each monomer constituting the monomer raw material and the mass fraction (copolymerization ratio) of the monomer. It can be calculated from the equation (1).
  • T 1, T 2 ⁇ T n Is the glass transition temperature (absolute temperature) of the homopolymer of each monomer.
  • Tg of the homopolymer a value described in the “Adhesion Technology Handbook” of Nikkan Kogyo Shimbun Co., Ltd. or “Polymer Handbook” of Wiley-Interscience, which is a publicly known material, is adopted.
  • the Tg of a homopolymer of a monomer not described in the above-mentioned publicly known material the value obtained by the following method is adopted.
  • a test sample is prepared by casting and drying a homopolymer solution obtained by solution polymerization of a target monomer on a release liner.
  • differential scanning calorimetry was performed using a differential scanning calorimeter (DSC) at a rate of temperature increase of 10 ° C./min from ⁇ 80 ° C. to 280 ° C., and the endothermic start temperature due to glass transition. Is adopted as the Tg of the homopolymer.
  • Examples of the (D) photopolymerization initiator in the present invention include a carbonyl photopolymerization initiator, a sulfide photopolymerization initiator, a quinone photopolymerization initiator, an azo photopolymerization initiator, and a sulfochloride photopolymerization initiator. Thioxanthone photopolymerization initiator, peroxide photopolymerization initiator, and the like.
  • carbonyl photopolymerization initiator examples include benzophenone, benzyl, benzoin, ⁇ -bromoacetophenone, chloroacetone, acetophenone, 2,2-diethoxyacetophenone, 2,2-dimethoxy-2-phenylacetophenone, p-dimethylamino.
  • Examples of the sulfide photopolymerization initiator include diphenyl disulfide, dibenzyl disulfide, tetraethylthiuram disulfide, tetramethylammonium monosulfide and the like.
  • Examples of the quinone photopolymerization initiator include benzoquinone and anthraquinone.
  • Examples of the azo photopolymerization initiator include azobisisobutyronitrile, 2,2′-azobispropane, hydrazine, and the like.
  • Examples of the thioxanthone photopolymerization initiator include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone and the like.
  • peroxide photopolymerization initiator examples include benzoyl peroxide and di-t-butyl peroxide.
  • photopolymerization initiators 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane-1 is preferred from the viewpoint of solubility in the resulting composition for a photocurable transparent adhesive sheet. -ON is preferred.
  • photoinitiators are used individually or in combination of 2 or more types.
  • the content of the photopolymerization initiator is 0.2 to 5% by mass in the photocurable transparent adhesive sheet composition from the viewpoint of the balance between photocurability and the strength and adhesiveness of the resulting adhesive sheet. It is preferably 0.5 to 3% by mass, more preferably 0.8 to 2% by mass.
  • the content of the photopolymerization initiator is less than 0.2% by mass, the photocuring tends to be insufficient, and when it exceeds 5% by mass, the adhesiveness of the obtained pressure-sensitive adhesive sheet tends to decrease. There is not preferable.
  • the composition for a photocurable transparent pressure-sensitive adhesive sheet of the present invention is preferably 10 to 50% by mass of the component (A) and 1 to 30% by mass of the component (B) based on the total amount of the composition for the photocurable transparent pressure-sensitive adhesive sheet. %, (C) component 20 to 88% by mass, and (D) component 0.2 to 5% by mass. More preferably, the component (A) is 15 to 45% by mass, the component (B) is 5 to 25% by mass, and the component (C) is 20 to 70% by mass based on the total amount of the photocurable transparent adhesive sheet composition. And (D) component 0.2 to 5% by mass.
  • the component (A) is 20 to 40% by mass
  • the component (B) is 10 to 20% by mass
  • the component (C) is 40 to 69% by mass with respect to the total amount of the photocurable transparent adhesive sheet composition.
  • (D) component 0.5 to 3% by mass.
  • a tackifier resin may be added as necessary in order not to lower the transparency in order to improve the adhesive strength of the obtained pressure-sensitive adhesive sheet.
  • tackifying resins include rosin resins such as rosin and rosin esterified products; terpene resins such as diterpene polymers and ⁇ -pinene-phenol copolymers; aliphatic (C5) and aromatic ( Petroleum resin such as C9); styrene resin, phenol resin, xylene resin and the like.
  • an esterified product of hydrogenated rosin or disproportionated rosin with few unsaturated double bonds, aliphatic or aromatic petroleum resin, high Tg acrylic resin, or the like is preferable to add to the adhesive sheet.
  • addition amount of tackifying resin 100 mass parts of total amount of (A) component, (B) component, (C) component, and (D) component with respect to 100 mass parts of composition for photocurable transparent adhesive sheets 1 to 10 parts by mass is preferably added.
  • composition for a photocurable transparent pressure-sensitive adhesive sheet of the present invention may contain various known additives as long as the transparency is not impaired.
  • Additives include plasticizers, surface lubricants, leveling agents, softeners, antioxidants, antioxidants, light stabilizers, UV absorbers, polymerization inhibitors, benzotriazole-based light stabilizers, phosphate esters System and other flame retardants, and antistatic agents such as surfactants.
  • composition for a photocurable transparent adhesive sheet of the present invention may be made into a solution using an organic solvent for the purpose of adjusting the viscosity at the time of coating.
  • organic solvent examples include methyl ethyl ketone, acetone, ethyl acetate, tetrahydrofuran, dioxane, cyclohexanone, n-hexane, toluene, xylene, n-propanol and isopropanol. These organic solvents may be used alone or in combination of two or more.
  • the acid value of the composition for a photocurable transparent adhesive sheet of the present invention is preferably 0 to 0.5 mgKOH / g, more preferably 0 to 0.1 mgKOH / g, and further preferably 0 to 0.05 mgKOH / g. .
  • the acid value of the composition is a value measured according to JIS K0070. For example, measurement is performed as follows.
  • composition for transparent adhesive sheet for fixing transparent conductive film is a composition for pressure-sensitive adhesive sheets for fixing a transparent conductive film comprising the above-described composition for a photocurable transparent pressure-sensitive adhesive sheet.
  • any conductive layer may be used as long as it has a conductive layer on at least one surface layer.
  • the transparent conductive film provided by (1) is mentioned.
  • the conductive material deposited or coated in the conductive layer of the transparent conductive film is not particularly limited, and specific examples include indium tin oxide, indium oxide, tin oxide, zinc oxide, cadmium oxide, gallium oxide, and titanium oxide. It is done. Of these, indium tin oxide having excellent transparency and conductivity is preferably used.
  • the substrate on which the conductive material is deposited or coated is not particularly limited, and examples thereof include glass and resin films.
  • the transparent pressure-sensitive adhesive sheet for fixing a transparent conductive film of the present invention is a transparent pressure-sensitive adhesive sheet for fixing a transparent conductive film obtained by curing the above-described composition for fixing a transparent conductive film. It can be suitably bonded and the conductive layer is unlikely to corrode. Therefore, the laminated body which adhere
  • the adhesive layer consists of a single layer, multiple layers may be laminated
  • it is preferable that it is a double-sided adhesive sheet which does not have a base material but consists only of an adhesive layer from a viewpoint of ensuring transparency and shape followability.
  • the transparent adhesive sheet for fixing a transparent conductive film of the present invention is obtained by applying a transparent adhesive sheet composition for fixing a transparent conductive film to a release PET film, and irradiating the applied composition with ultraviolet rays using an ultraviolet irradiation device or the like. It can be obtained by photocuring.
  • the thickness of the transparent conductive film fixing pressure-sensitive adhesive sheet is preferably 5 to 500 ⁇ m, more preferably 10 to 300 ⁇ m. When the film thickness of the adhesive sheet for fixing a transparent conductive film becomes thinner than 5 ⁇ m, it becomes difficult to bond the adhesive sheet, and when it becomes thicker than 500 ⁇ m, it tends to be difficult to control the film thickness.
  • the pressure-sensitive adhesive sheet for fixing a transparent conductive film of the present invention preferably has a gel fraction determined by the following formula (3) of 80 to 100% when immersed in toluene at room temperature for 24 hours, More preferably, it is 100%.
  • the gel fraction of the pressure-sensitive adhesive sheet is lower than 80%, stringing or the like from the processed end face tends to occur during punching.
  • ⁇ (Meth) acrylic group-containing polyolefin compound (A-1)> A four-necked flask equipped with a thermometer, a stirrer, a dropping funnel, and a cooling tube with a drying tube is mixed with isophorone diisocyanate 101.2 g and hydroxyl-terminated hydrogenated polybutadiene (manufactured by Nippon Soda Co., Ltd., product name: GI-3000, weight average molecular weight). 14,000) was charged at 84 ° C. and reacted at 60 ° C. When the residual isocyanate group became 1% or less, 53.9 g of 2-hydroxyethyl acrylate was charged and the temperature was raised to 70 ° C.
  • ⁇ (Meth) acrylic group-containing polyolefin compound (A-4)> A four-necked flask equipped with a thermometer, a stirrer, a dropping funnel, and a cooling tube with a drying tube, 61.2 g of isophorone diisocyanate and hydrogenated polybutadiene having a hydroxyl group (Product name: GI-3000, manufactured by Nippon Soda Co., Ltd., weight average molecular weight) 14,000) was charged at 91 ° C. and reacted at 60 ° C. When the residual isocyanate group became 1% or less, 21.3 g of 2-hydroxyethyl acrylate was charged and the temperature was raised to 70 ° C. to carry out the reaction. However, it became high molecular weight and gelled during the reaction.
  • Examples 1 to 6, Comparative Examples 1 to 4 Each of the compositions shown in Table 1 was blended and mixed with a disper at room temperature to prepare a uniform photocurable transparent adhesive sheet composition.
  • the prepared composition for a photocurable transparent adhesive sheet is applied to a release PET film (100 mm ⁇ 100 mm ⁇ 100 ⁇ m) using an applicator so that the film thickness is 200 ⁇ m, and the upper surface is a release PET film having a thickness of 25 ⁇ m.
  • the pressure-sensitive adhesive sheet having a thickness of about 200 ⁇ m sandwiched between the release PET films was obtained by irradiating with UV rays and curing under the condition of 2 .
  • the composition for a photocurable transparent pressure-sensitive adhesive sheet containing the (meth) acryl group-containing polyolefin compound having a weight average molecular weight exceeding 300,000 The comparative example could not be prepared.
  • the adhesive sheet obtained above was cut to a size of 50 mm ⁇ 50 mm, the release PET film having a thickness of 25 ⁇ m was peeled off, and bonded to the indium tin oxide film surface of the 100 mm ⁇ 100 mm indium tin oxide-deposited PET film.
  • the electrical resistance value measuring device “Lorestar GP” manufactured by Mitsubishi Chemical Corporation was used at both ends of the bonded adhesive sheet, and the initial electrical resistance value (R 1 ) was measured.
  • the indium tin oxide-deposited PET film to which the adhesive sheet was bonded was left at 90 ° C. for 500 hours and left at 23 ° C. and 50% RH for 1 hour.
  • the resistance value (R 2 ) was measured.
  • the increase rate of the electric resistance value of the indium tin oxide film was calculated by the following formula (4).
  • the rate of increase in electrical resistance value was evaluated according to the following criteria. The results are shown in Table 1. ⁇ : Electrical resistance value increase rate of less than 5% ⁇ ; Electrical resistance value increase rate of 5 to less than 10% ⁇ : Electrical resistance value increase rate of 10% or more
  • the pressure-sensitive adhesive sheet obtained above was cut to a size of 25 ⁇ 100 mm, and after removing the 100 ⁇ m-thick release PET film from the release PET film existing on both sides of the pressure-sensitive adhesive sheet, the pressure-sensitive adhesive surface (measurement surface) was tested.
  • a 2 kg rubber roller (width: about 50 mm) was attached to the plate by reciprocating once to prepare a measurement sample.
  • a glass plate was used as a test plate.
  • the obtained measurement sample is left for 24 hours in an environment of 23 ° C.
  • Total light transmittance measurement The pressure-sensitive adhesive sheet obtained above was cut into a size of 30 mm ⁇ 30 mm, and the release PET film having a thickness of 25 ⁇ m was peeled off from the release PET film existing on both sides of the pressure-sensitive adhesive sheet, and then bonded to a glass plate for measurement. A sample was used. About the sample for a measurement, the total light transmittance (%) was measured using "HR-100 type" by Murakami Color Research Laboratory. The results are shown in Table 1.
  • the pressure-sensitive adhesive sheet was cut into a size of 20 mm ⁇ 40 mm to prepare a measurement sample. After this measurement sample was immersed in toluene at 23 ° C. for 24 hours, the measurement sample was taken out from toluene. Thereafter, the measurement sample was dried at 130 ° C. for 1 hour. Next, the weight of the measurement sample after drying was measured, and the gel fraction was calculated by the above-described formula (3). The results are shown in Table 1.
  • the composition for the photocurable transparent adhesive sheet of the present invention obtained in the examples is superior in the electrical resistance value increase rate, the total light transmittance, and the adhesive strength as compared with the comparative example.
  • composition for a photocurable transparent pressure-sensitive adhesive sheet of the present invention is useful as a pressure-sensitive adhesive sheet for fixing a transparent conductive film because it has high transparency, metal corrosion prevention and is excellent in adhesiveness. This is useful for fixing a transparent conductive film used in a touch panel of the type.

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

Abstract

L'objectif de la présente invention est de produire : une composition photodurcissable pour utilisation dans une feuille adhésive autocollante transparente qui est fortement transparente et correctement adaptée pour poinçonnage, a une couche d'agent adhésif autocollant fortement cohésive, et ne corrode pas une couche conductrice d'un film conducteur transparent même si elle est collée directement sur la surface de ladite couche conductrice ; et une feuille adhésive autocollante. La présente invention est une composition photodurcissable pour utilisation dans une feuille adhésive autocollante transparente, ladite composition comprenant : (A) un composé polyoléfine contenant un groupe (méth)acryle qui a un poids moléculaire moyen en poids de 10 000 à 300 000 ; (B) un ester d'acide (méth)acrylique qui a un groupe hydroxyle ; (C) des monomères photopolymérisables autres que des esters d'acide (méth)acrylique ayant des groupes hydroxyle ; et (D) un initiateur de photopolymérisation. Ladite composition photodurcissable pour utilisation dans une feuille adhésive autocollante transparente est caractérisée en ce que des monomères contenant un groupe carboxyle constituent pas plus de 0,1 % de la masse des monomères photopolymérisables (C).
PCT/JP2011/069288 2010-09-17 2011-08-26 Composition photodurcissable pour utilisation dans une feuille adhésive autocollante transparente WO2012035958A1 (fr)

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JP2012533934A JP5854404B2 (ja) 2010-09-17 2011-08-26 光硬化性透明粘着シート用組成物
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JP2013242724A (ja) * 2012-05-21 2013-12-05 Showa Denko Kk 透明粘着シート用光硬化性組成物及び透明粘着シート
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TWI515281B (zh) 2016-01-01
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KR101494984B1 (ko) 2015-02-23
JPWO2012035958A1 (ja) 2014-02-03
JP5854404B2 (ja) 2016-02-09
CN103108930A (zh) 2013-05-15
CN103108930B (zh) 2014-08-20

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