CN115584226A - Adhesive composition for optical film, adhesive layer for optical film, and adhesive film for optical film - Google Patents

Adhesive composition for optical film, adhesive layer for optical film, and adhesive film for optical film Download PDF

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Publication number
CN115584226A
CN115584226A CN202211370331.5A CN202211370331A CN115584226A CN 115584226 A CN115584226 A CN 115584226A CN 202211370331 A CN202211370331 A CN 202211370331A CN 115584226 A CN115584226 A CN 115584226A
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meth
acrylate
group
film
optical film
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Inventor
长仓毅
长谷川良
吉田弘幸
菱沼昌世
铃木史惠
大津贺健太郎
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Fujimori Kogyo Co Ltd
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Fujimori Kogyo Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/062—Copolymers with monomers not covered by C09J133/06
    • C09J133/068—Copolymers with monomers not covered by C09J133/06 containing glycidyl groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/062—Copolymers with monomers not covered by C09J133/06
    • C09J133/066—Copolymers with monomers not covered by C09J133/06 containing -OH groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/08—Homopolymers or copolymers of acrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/10—Homopolymers or copolymers of methacrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/10—Homopolymers or copolymers of methacrylic acid esters
    • C09J133/12—Homopolymers or copolymers of methyl methacrylate
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • 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
    • C09J7/22—Plastics; Metallised plastics
    • C09J7/25—Plastics; Metallised plastics based on macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C09J7/255—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
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/40—Adhesives in the form of films or foils characterised by release liners
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising 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
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/318—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
    • C09J2301/312—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier parameters being the characterizing feature

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Polarising Elements (AREA)
  • Adhesive Tapes (AREA)
  • Liquid Crystal (AREA)
  • Electroluminescent Light Sources (AREA)
  • Laminated Bodies (AREA)

Abstract

The invention provides an adhesive layer for an optical film, an adhesive film for an optical film and an adhesive composition for an optical film, wherein the adhesive layer is used for bonding the optical film assembled in an image display device and has excellent heat resistance and durability. The adhesive layer for an optical film is formed by crosslinking an acrylic polymer, wherein the acrylic polymer is formed by a copolymer which is formed by copolymerizing the following components and has Tg of-60 ℃ to-30 ℃, and the components are as follows: 100 parts by weight of at least two or more monomers selected from the group consisting of alkyl (meth) acrylate monomers, aromatic group-containing (meth) acrylate monomers, and nitrogen-containing vinyl monomers, 0.1 to 10.0 parts by weight of a carboxyl group-containing copolymerizable vinyl monomer, and 0.05 to 4.5 parts by weight of a hydroxyl group-containing copolymerizable vinyl monomer.

Description

Adhesive composition for optical film, adhesive layer for optical film, and adhesive film for optical film
The present invention is a divisional application of chinese patent application having application numbers 201610266429.4, 2016, 4, 26, entitled "adhesive composition for optical film, adhesive layer for optical film, and adhesive film for optical film", and the application claims priority based on japanese patent application No. 2015-115427, which was filed on 8/6/2015.
Technical Field
The present invention relates to an adhesive layer for an optical film, an adhesive film for an optical film, and an adhesive composition for an optical film for producing the same. More particularly, the present invention relates to an adhesive layer for an optical film, an adhesive film for an optical film, and an adhesive composition for an optical film for producing the same, each having excellent heat resistance and durability, for bonding an optical film incorporated in an image display device.
Background
In recent years, various optical films have been used in various image display devices. For example, optical films such as polarizing films and retardation films are used for the purpose of improving contrast and preventing reflection of external light. In order to bond these optical films to an adherend such as a liquid crystal panel or an organic EL (electroluminescence) panel, various adhesive films have been proposed (for example, refer to patent document 1). Further, it is known that reflection of external light can be suppressed by disposing one 1/4 λ phase difference film having a polarization axis angle of-45 ° with respect to the polarizing film, or one-15 ° 1/2 λ phase difference film and one-75 ° 1/4 λ phase difference film between the reflective layer on the back surface of the organic EL panel and the polarizing film.
Documents of the prior art
Patent document
Patent document 1: japanese unexamined patent publication No. 2012-201734
Disclosure of Invention
Technical problems to be solved by the invention
As described above, in order to prevent reflection of external light from the organic EL panel, a 1/4 λ retardation film having reverse wavelength dispersion (birefringence increases as the wavelength increases) is provided between the polarizing film and the organic EL panel. In addition, conventionally, as a retardation film of 1/4 λ, a retardation film made of a polycarbonate film is widely used. However, when a polycarbonate-based film is used, there is a problem that foaming due to outgassing from the polycarbonate cannot be suppressed.
The present invention has been made in view of the above circumstances, and an object of the present invention is to provide an adhesive layer for an optical film, an adhesive film for an optical film, and an adhesive composition for an optical film for producing the same, which are used for bonding an optical film incorporated in an image display device and have excellent heat resistance and durability.
Means for solving the problems
In order to solve the above-mentioned problems, the technical idea of the present invention is to obtain an adhesive agent layer having excellent heat resistance and durability by using, as a crosslinked adhesive agent layer, an acrylic polymer composed of a copolymer having a Tg of-60 ℃ to-30 ℃ which is obtained by copolymerizing: 100 parts by weight of total amount of at least two monomers selected from the group consisting of alkyl (meth) acrylate monomers having alkyl groups and carbon atoms of 1 to 14 carbon atoms, (meth) acrylate monomers having aromatic groups, and nitrogen-containing vinyl monomers, 0.1 to 10.0 parts by weight of a copolymerizable vinyl monomer having a carboxyl group, and 0.05 to 4.5 parts by weight of a copolymerizable vinyl monomer having a hydroxyl group.
In order to solve the above-mentioned technical problems, the present invention provides an adhesive composition for an optical film, comprising an acrylic polymer and a crosslinkable compound, wherein the acrylic polymer is composed of a copolymer having a Tg of-60 ℃ to-30 ℃ which is obtained by copolymerizing: 100 parts by weight in total of (A) at least two or more monomers selected from the group consisting of alkyl (meth) acrylate monomers (a 1) having alkyl groups of C1 to C14, aromatic group-containing (meth) acrylate monomers (a 2), and nitrogen-containing vinyl monomers (a 3), 0.1 to 10.0 parts by weight of (B) carboxyl group-containing copolymerizable vinyl monomers, and 0.05 to 4.5 parts by weight of (C) hydroxyl group-containing copolymerizable vinyl monomers, wherein one of the monomers belonging to (a 1) is 51 parts by weight or more and 95 parts by weight or less, the total of the other or more monomers selected from the group consisting of the monomers (a 1) to (a 3) is 5 parts by weight or more and 49 parts by weight or less, and the total of these is 100 parts by weight.
Preferably, the crosslinkable compound is an epoxy compound having 2 or more functional groups, and is contained in an amount of 0.001 to 0.5 part by weight based on 100 parts by weight of the total amount of at least two or more monomers selected from the group consisting of the monomers (a 1) to (a 3).
Preferably, the (B) carboxyl group-containing copolymerizable vinyl monomer copolymerized in the acrylic polymer is at least one or more selected from the group consisting of (meth) acrylic acid, carboxyethyl (meth) acrylate, carboxypentyl (meth) acrylate, 2- (meth) acryloyloxyethylhexahydrophthalic acid, 2- (meth) acryloyloxyethylphthalic acid, 2- (meth) acryloyloxyethylsuccinic acid, 2- (meth) acryloyloxyethylmaleic acid, carboxypolycaprolactone mono (meth) acrylate, 2- (meth) acryloyloxyethyltetrahydrophthalic acid, and the (C) hydroxyl group-containing copolymerizable vinyl monomer copolymerized in the acrylic polymer is at least one selected from the group consisting of 8-hydroxyoctyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, N-hydroxy (meth) acrylamide, N-hydroxymethyl (meth) acrylamide, N-hydroxyethyl (meth) acrylamide.
The (a 2) aromatic group-containing (meth) acrylate monomer copolymerized in the acrylic polymer is preferably at least one selected from the group consisting of benzyl (meth) acrylate, naphthyl (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxybutyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, 2- (1-naphthyloxy) ethyl (meth) acrylate, 6- (1-naphthyloxy) hexyl (meth) acrylate, 6- (2-naphthyloxy) hexyl (meth) acrylate, 8- (1-naphthyloxy) octyl (meth) acrylate, and 8- (2-naphthyloxy) octyl (meth) acrylate.
The adhesive layer for an optical film is characterized in that the gel fraction of the adhesive layer for an optical film obtained by crosslinking the adhesive composition for an optical film is 60 to 90%, and the thickness of the adhesive layer for an optical film is 5 to 25 [ mu ] m.
The present invention also provides an adhesive layer for an optical film, which is characterized in that the adhesive layer for an optical film formed by crosslinking the adhesive composition for an optical film is transferred on both surfaces of a retardation film made of a polycarbonate resin film, and a laminate of an optical film with an adhesive layer formed by laminating a polarizing film on one surface thereof is laminated on alkali-free glass, and then stored in a dry atmosphere at 85 ℃ for 200 hours, and then taken out and placed in an atmosphere of 23 ℃ x 50% rh for 1 hour, and then observed, and has durability against foaming.
The present invention also provides an adhesive film for an optical film, wherein the adhesive composition for an optical film is coated on one surface of a release film to form an adhesive layer for an optical film, and the adhesive layer has a structure of release film/adhesive layer for an optical film/release film.
The present invention also provides an adhesive film for an optical film, which is characterized in that an adhesive layer for an optical film, which is obtained by crosslinking the adhesive composition for an optical film, is laminated on one surface of a substrate.
In addition, the present invention provides an image display device, wherein the adhesive composition for an optical film is crosslinked to form an adhesive layer for an optical film, which is used for bonding the optical film.
The present invention also provides a polarizing plate with an adhesive layer, wherein the adhesive layer for an optical film is formed by crosslinking the adhesive composition for an optical film.
The invention also provides a polarizing plate with an adhesive layer, which uses the adhesive layer for the optical film formed by crosslinking the adhesive composition for the optical film, and uses a phase difference film with a phase difference of 1/4 lambda as a constituent material.
The present invention also provides an optical film having an adhesive layer, wherein the adhesive layer for an optical film obtained by crosslinking the adhesive composition for an optical film is laminated on at least one surface of the optical film.
Effects of the invention
According to the present invention, an adhesive layer for an optical film, an adhesive film for an optical film, and an adhesive composition for an optical film used for them, which have excellent heat resistance and durability, can be provided by forming the adhesive layer by crosslinking an acrylic polymer composed of a copolymer of: a copolymer having a Tg of-60 ℃ to-30 ℃ which is obtained by copolymerizing 100 parts by weight in total of at least two or more members selected from the group consisting of alkyl (meth) acrylate monomers, (meth) acrylate monomers having an aromatic group and nitrogen-containing vinyl monomers, 0.1 to 10.0 parts by weight of a copolymerizable vinyl monomer having a carboxyl group and 0.05 to 4.5 parts by weight of a copolymerizable vinyl monomer having a hydroxyl group.
The adhesive layer for optical films of the present invention was transferred to both sides of a retardation film made of a polycarbonate resin film, and the laminate of the optical film with the adhesive layer, which was obtained by laminating a polarizing film on one side thereof, was laminated on alkali-free glass, and then stored in a dry atmosphere at 85 ℃ for 200 hours, and then taken out and placed in an atmosphere of 23 ℃ x 50% rh for 1 hour, and then observed, and the durability against foaming was exhibited. Therefore, the adhesive layer for an optical film of the present invention can exert an extremely excellent effect in the bonding of a retardation film made of a polycarbonate resin film.
Detailed Description
The present invention will be described below based on preferred embodiments.
The pressure-sensitive adhesive composition for an optical film of the present invention contains an acrylic polymer and a crosslinkable compound. The adhesive composition for an optical film is crosslinked to form the adhesive layer for an optical film of the present invention. The pressure-sensitive adhesive composition for optical films of the present invention comprises an acrylic polymer and a crosslinkable compound, wherein the acrylic polymer is composed of a copolymer having a Tg of-60 ℃ to-30 ℃ which is obtained by copolymerizing: 100 parts by weight in total of (A) at least two or more selected from the group consisting of alkyl (meth) acrylate monomers (a 1) having an alkyl group and having 1 to 14 carbon atoms, aromatic group-containing (meth) acrylate monomers (a 2), and nitrogen-containing vinyl monomers (a 3), 0.1 to 10.0 parts by weight of (B) a carboxyl group-containing copolymerizable vinyl monomer, and 0.05 to 4.5 parts by weight of (C) a hydroxyl group-containing copolymerizable vinyl monomer, wherein one of the monomers belonging to the group (a 1) is 51 parts by weight or more and 95 parts by weight or less, the total amount of the other or more selected from the group consisting of the monomers (a 1) to (a 3) is 5 parts by weight or more and 49 parts by weight or less, and the total amount of these is 100 parts by weight.
The adhesive layer for optical films of the present invention has durability against foaming, and is obtained by transferring the adhesive layer for optical films onto both surfaces of a retardation film made of a polycarbonate resin film, bonding a laminate of an optical film with an adhesive layer, which is obtained by bonding a polarizing film onto one surface of the laminate, to alkali-free glass, storing the laminate in a dry atmosphere at 85 ℃ for 200 hours, taking out the laminate, and observing the laminate in an atmosphere of 23 ℃ x 50% rh for 1 hour.
The acrylic polymer of the pressure-sensitive adhesive composition for optical films of the present invention is a copolymer obtained by copolymerizing two or more compounds selected from the group consisting of monomers (main component monomers) belonging to group (a) and one or more compounds selected from the group consisting of monomers (functional group monomers) belonging to groups (B) and (C), respectively. The monomer belonging to group (a) may be at least two or more monomers selected from the group consisting of alkyl (meth) acrylate monomers (a 1) having an alkyl group having 1 to 14 carbon atoms, (meth) acrylate monomers (a 2) having an aromatic group, and nitrogen-containing vinyl monomers (a 3). As the monomer belonging to the group (B), at least one or more of carboxyl group-containing copolymerizable vinyl monomers can be used, and as the monomer belonging to the group (C), at least one or more of hydroxyl group-containing copolymerizable vinyl monomers can be used. In the present specification, a (meth) acrylate is a generic name of an acrylate and a methacrylate.
In the adhesive composition of the adhesive layer for an optical film of the present invention, as (a 1) an alkyl (meth) acrylate monomer having an alkyl group with a carbon number of C1 to C14 belonging to group (A), examples of the organic solvent include at least one selected from the group consisting of methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, pentyl (meth) acrylate, isoamyl (meth) acrylate, hexyl (meth) acrylate, isohexyl (meth) acrylate, heptyl (meth) acrylate, isoheptyl (meth) acrylate, octyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, nonyl (meth) acrylate, isononyl (meth) acrylate, decyl (meth) acrylate, isodecyl (meth) acrylate, undecyl (meth) acrylate, isoundecyl (meth) acrylate, dodecyl (meth) acrylate, isotridecyl (meth) acrylate, isopropyl (meth) acrylate, tetradecyl (meth) acrylate, and isotetradecyl (meth) acrylate. The alkyl group of the alkyl (meth) acrylate monomer may be linear, branched, or cyclic (alicyclic).
The acrylic polymer of the pressure-sensitive adhesive composition for optical films of the present invention preferably contains one of the monomers selected from the group consisting of (a 1) alkyl (meth) acrylate monomers having an alkyl group of C1 to C14 in a proportion of 51 to 95 parts by weight, based on 100 parts by weight of the total amount of at least two or more monomers selected from the group consisting of monomers (a 1) to (a 3) belonging to group (a).
Further, (a 1) the alkyl (meth) acrylate monomer having an alkyl group having a carbon number of C1 to C14 is an extremely common compound used in a large amount in the chemical field, and therefore is easily available, is a relatively inexpensive material, and is a compound that can be used to effectively control the production cost of the adhesive composition as a product.
Further, (a 1) the alkyl (meth) acrylate monomer having an alkyl group having 1 to 14 carbon atoms includes a large amount of a compound having a glass transition temperature (Tg) of-30 ℃ or lower, and therefore, the compound is a compound having high utility value in terms of easy selection as a method for adjusting the physical properties of the adhesive layer for an optical film of the present invention.
In the adhesive composition of the adhesive layer for an optical film of the present invention, the (meth) acrylate monomer (a 2) having an aromatic group belonging to the group (a) includes at least one selected from the group consisting of benzyl (meth) acrylate, naphthyl (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxybutyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, 2- (1-naphthyloxy) ethyl (meth) acrylate, 2- (2-naphthyloxy) ethyl (meth) acrylate, 6- (1-naphthyloxy) hexyl (meth) acrylate, 6- (2-naphthyloxy) hexyl (meth) acrylate, 8- (1-naphthyloxy) octyl (meth) acrylate, and 8- (2-naphthyloxy) octyl (meth) acrylate. In order to obtain an adhesive layer for an optical film having a high refractive index, at least one or more (meth) acrylate monomers having an aromatic group are preferably copolymerized in an acrylic polymer.
The acrylic polymer of the pressure-sensitive adhesive composition for an optical film of the present invention may contain (a 2) a (meth) acrylate monomer having an aromatic group in an amount of 0 to 30 parts by weight based on 100 parts by weight of the total amount of at least two or more monomers selected from the group consisting of monomers (a 1) to (a 3) belonging to group (a).
When the acrylic polymer of the present invention contains (a 2) the (meth) acrylate monomer having an aromatic group, the acrylic polymer is preferably contained in a proportion of 3 to 25 parts by weight, more preferably 8 to 20 parts by weight, based on 100 parts by weight of the total amount of at least two or more monomers selected from the monomer groups consisting of (a 1) to (a 3) belonging to group (a).
In the adhesive composition of the adhesive layer for an optical film of the present invention, examples of the nitrogen-containing vinyl monomer (a 3) belonging to the group (a) include an amide bond-containing (meth) acrylic monomer, an amino group-containing (meth) acrylic monomer, and the like. More specifically, cyclic nitrogen vinyl compounds having an N- (meth) acryloyl-substituted heterocyclic structure, such as N- (meth) acryloyl morpholine, N- (meth) acryloyl piperazine, N- (meth) acryloyl aziridine, N- (meth) acryloyl azetidine, N- (meth) acryloyl pyrrolidine, N- (meth) acryloyl piperidine, N- (meth) acryloyl azepane, and N- (meth) acryloyl azocane; unsubstituted or monoalkyl-substituted (meth) acrylamides such as (meth) acrylamide, N-methyl (meth) acrylamide, N-isopropyl (meth) acrylamide, and N-tert-butyl (meth) acrylamide; dialkyl-substituted (meth) acrylamides such as N, N-dimethyl (meth) acrylamide, N-diethyl (meth) acrylamide, N-dipropylacrylamide, N-diisopropyl (meth) acrylamide, N-dibutyl (meth) acrylamide, N-ethyl-N-methyl (meth) acrylamide, N-methyl-N-propyl (meth) acrylamide, and N-methyl-N-isopropyl (meth) acrylamide; n, N-dimethylaminomethyl (meth) acrylate, N-dimethylaminoethyl (meth) acrylate, N-dimethylaminopropyl (meth) acrylate, N-dimethylaminoisopropyl (meth) acrylate, N-dimethylaminobutyl (meth) acrylate, N-diethylaminomethyl (meth) acrylate, N, dialkylamino (meth) acrylates such as N-diethylaminoethyl (meth) acrylate, N-ethyl-N-methylaminoethyl (meth) acrylate, N-methyl-N-propylaminoethyl (meth) acrylate, N-methyl-N-isopropylaminoethyl (meth) acrylate, N-dibutylaminoethyl (meth) acrylate, and tert-butylaminoethyl (meth) acrylate; n, N-dialkyl-substituted aminopropyl (meth) acrylamides such as N, N-dimethylaminopropyl (meth) acrylamide, N-diethylaminopropyl (meth) acrylamide, N-dipropylaminopropyl (meth) acrylamide, N-diisopropylaminopropyl (meth) acrylamide, N-ethyl-N-methylaminopropyl (meth) acrylamide, N-methyl-N-propylaminopropyl (meth) acrylamide, and N-methyl-N-isopropylaminopropyl (meth) acrylamide; at least one selected from the group consisting of (meth) acrylonitrile. The nitrogen-containing vinyl monomer (a 3) preferably does not contain a hydroxyl group, and more preferably does not contain a hydroxyl group or a carboxyl group.
The acrylic polymer of the pressure-sensitive adhesive composition for an optical film of the present invention may contain (a 3) a nitrogen-containing vinyl monomer in a proportion of 0 to 20 parts by weight based on 100 parts by weight of the total amount of at least two or more monomers selected from the group consisting of monomers (a 1) to (a 3) belonging to group (a).
When the acrylic polymer of the present invention contains (a 3) a nitrogen-containing vinyl monomer, the total amount of at least two monomers selected from the group consisting of monomers (a 1) to (a 3) belonging to group (a) is 100 parts by weight, more preferably 2 to 20 parts by weight, and particularly preferably 2 to 12 parts by weight.
The monomers (functional group monomers) belonging to the groups (B) and (C) contain a functional group reactive with the crosslinkable compound. Examples of such functional groups include carboxyl groups and hydroxyl groups. Further, the monomer belonging to the group (a) may not contain a functional group reactive with the crosslinkable compound.
In the adhesive composition of the adhesive layer for an optical film of the present invention, the carboxyl group-containing copolymerizable vinyl monomer (B) includes at least one selected from the group consisting of (meth) acrylic acid, carboxyethyl (meth) acrylate, carboxypentyl (meth) acrylate, 2- (meth) acryloyloxyethylhexahydrophthalic acid, 2- (meth) acryloyloxyethylphthalic acid, 2- (meth) acryloyloxyethylsuccinic acid, 2- (meth) acryloyloxyethylmaleic acid, carboxypolycaprolactone mono (meth) acrylate, and 2- (meth) acryloyloxyethyltetrahydrophthalic acid.
The acrylic polymer of the present invention preferably contains the carboxyl group-containing copolymerizable vinyl monomer (B) in an amount of 0.1 to 10.0 parts by weight, more preferably 0.3 to 9.0 parts by weight, and particularly preferably 0.5 to 9.0 parts by weight, based on 100 parts by weight of the total amount of at least two or more monomers selected from the group consisting of monomers (a 1) to (a 3) belonging to group (a).
In the adhesive composition of the adhesive layer for an optical film of the present invention, examples of the (C) hydroxyl group-containing copolymerizable vinyl monomer include at least one or more of hydroxyl group-containing alkyl (meth) acrylates such as 8-hydroxyoctyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, and 2-hydroxyethyl (meth) acrylate, and hydroxyl group-containing (meth) acrylamides such as N-hydroxy (meth) acrylamide, N-hydroxymethyl (meth) acrylamide, and N-hydroxyethyl (meth) acrylamide. Among these, the hydroxyl group-containing copolymerizable vinyl monomer is preferably at least one selected from the group consisting of 8-hydroxyoctyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, N-hydroxy (meth) acrylamide, N-hydroxymethyl (meth) acrylamide and N-hydroxyethyl (meth) acrylamide.
The acrylic polymer of the adhesive layer for an optical film of the present invention preferably contains 0.05 to 4.5 parts by weight of (C) a hydroxyl group-containing copolymerizable vinyl monomer, more preferably 0.05 to 1.2 parts by weight, and particularly preferably 0.05 to 0.5 parts by weight, based on 100 parts by weight of the total amount of at least two or more monomers selected from the group consisting of monomers (a 1) to (a 3) belonging to group (a).
The polymerization method of the copolymer used as the acrylic polymer is not particularly limited, and a suitable known polymerization method such as a solution polymerization method or an emulsion polymerization method can be used. In the monomer composition of the acrylic polymer, out of 100 parts by weight of the total amount of at least two or more monomers selected from the group consisting of monomers (a 1) to (a 3) belonging to group (a), one of the monomers belonging to the alkyl (meth) acrylate monomer having an alkyl group of C1 to C14 is set to 51 parts by weight or more and 95 parts by weight or less (abbreviated as M1), the total amount of the other or more monomers selected from the group consisting of monomers (a 1) to (a 3) is set to 5 parts by weight or more and 49 parts by weight or less (abbreviated as M2), and the total amount of M1 and M2 is set to 100 parts by weight. M1 is composed of only one monomer, and M2 is composed of a monomer other than M1. As long as each monomer constituting M2 belongs to any one of (a 1) to (a 3), M2 may or may not contain a monomer belonging to (a 1) (other than the monomer corresponding to M1); m2 may or may not contain the monomer belonging to (a 2); m2 may or may not contain the monomer belonging to (a 3).
In the present invention, the glass transition temperature (hereinafter referred to as Tg) of the acrylic polymer is preferably from-60 ℃ to-30 ℃. If the Tg exceeds-30 ℃, the foaming resistance (durability) is lowered, which is not preferable. Further, the Tg of the acrylic polymer of the present invention is more preferably from-50 ℃ to-30 ℃. The weight average molecular weight of the acrylic polymer of the present invention is preferably 100 ten thousand or more, and more preferably in the range of 100 to 200 ten thousand.
The pressure-sensitive adhesive composition of the pressure-sensitive adhesive layer for an optical film of the present invention can be adjusted to desired physical property values by adding a crosslinkable compound or a suitable optional additive to the acrylic polymer.
The crosslinkable compound of the adhesive composition for an optical film of the present invention is a compound (crosslinking agent) for crosslinking an acrylic polymer. The crosslinkable compound is preferably an epoxy compound having 2 or more functional groups. The epoxy compound having 2 or more functions is not particularly limited as long as it has 2 or more epoxy groups in 1 molecule, and examples thereof include compounds prepared from 1, 3-bis (diglycidylaminomethyl) cyclohexane, 1, 3-bis (diglycidylaminomethyl) benzene [ another name: at least one member selected from among polyglycidyl amines such as N, N, N ', N' -tetraglycidyl-m-xylylenediamine ], diglycidyl aniline, etc., sorbitol polyglycidyl ether, (poly) ethylene glycol diglycidyl ether, 1, 6-hexanediol diglycidyl ether, glycerol polyglycidyl ether, trimethylolpropane polyglycidyl ether, bisphenol A diglycidyl ether, etc., polyglycidyl ethers such as diglycidyl hexahydrophthalate, diglycidyl maleate, etc.
Examples of the commercially available epoxy compounds that can be generally obtained include 1, 3-bis (diglycidylaminomethyl) cyclohexane, 1, 3-bis (diglycidylaminomethyl) benzene, and the like.
The pressure-sensitive adhesive composition for optical films of the present invention preferably contains 0.001 to 0.5 parts by weight of a crosslinkable compound, based on 100 parts by weight of the total amount of at least two or more monomers selected from the group consisting of monomers (a 1) to (a 3) belonging to group (a). As the crosslinkable compound, only an epoxy compound having 2 or more functions can be used.
As other optional components, known additives such as an antioxidant, an antistatic agent, a silane coupling agent, a surfactant, a curing accelerator, a plasticizer, a filler, a crosslinking catalyst, a crosslinking retarder, a curing retarder, a processing aid, and an aging inhibitor may be added as appropriate. These may be used alone or in combination of two or more.
The adhesive layer for an optical film of the present invention can be formed by applying the adhesive composition to a substrate or a release film and then crosslinking the adhesive composition. The gel fraction of the crosslinked adhesive layer for an optical film is preferably 60 to 90%. If the gel fraction of the adhesive layer for an optical film is outside this range, the heat resistance and durability are reduced, which is not preferable.
When the adhesive layer for an optical film of the present invention is used for laminating optical members between layers, a thin adhesive layer is preferable. The thickness of the adhesive layer for an optical film is preferably 5 to 25 μm. In order to reduce light reflection at the interface between the adhesive layer for an optical film and the optical member, the difference in refractive index between the adherend and the adhesive layer for an optical film is preferably as small as possible.
The adhesive film for optical films of the present invention can be produced by forming the adhesive layer for optical films of the present invention on one surface of a substrate, an optical film, or a release film. As a base film used for forming the adhesive layer for an optical film or a release film (spacer) for protecting the adhesive surface, a resin film such as a polyester film or the like can be used. The base film may be subjected to an anti-fouling treatment with a silicone or fluorine-based release agent, a coating agent, silica fine particles, or the like, and to an antistatic treatment with an antistatic agent or the like applied or blended to the surface of the resin film opposite to the side on which the adhesive layer for an optical film is formed.
The release film may be subjected to a release treatment with a silicone-based or fluorine-based release agent on the surface thereof to be bonded to the pressure-sensitive adhesive surface of the adhesive layer for an optical film. The release film/the adhesive layer for an optical film/the release film can be formed by bonding the release-treated surface of the release film to each of both surfaces of one adhesive layer for an optical film. In this case, the release films on both sides are peeled off sequentially or simultaneously to expose the adhesive surface, and the adhesive surface is bonded to an optical member such as an optical film. Examples of the optical film include a polarizing film, a retardation film, an antireflection film, an Anti-glare (Anti-glare) film, an ultraviolet absorbing film, an infrared absorbing film, an optical compensation film, and a brightness enhancement film.
The adhesive layer for an optical film of the present invention is excellent in heat resistance and durability, and therefore can be suitably used for laminating a retardation film and a polarizing film or an organic EL panel in a structure of a polarizing film/an adhesive layer for an optical film/a retardation film/an adhesive layer for an optical film/an organic EL panel.
The adhesive layer for an optical film and the adhesive film for an optical film of the present invention can be used for bonding various optical films incorporated in an image display device, various optical films for a touch panel, various optical films for electronic paper, various optical films incorporated in a liquid crystal panel, and various optical films incorporated in an organic EL panel. In addition, an optical film with an adhesive layer may be formed by laminating the adhesive layer for an optical film on at least one surface of the optical film. In the case of having an adhesive layer for an optical film protected by a release film, the adhesive layer for an optical film is exposed as the "adhesive layer for an optical film" by peeling the release film, and is bonded to another optical film, whereby a structure such as "adhesive layer for an optical film/optical film" using the adhesive layer for an optical film between layers can be obtained.
The adhesive layer for an optical film of the present invention is suitable for bonding various optical films incorporated in an image display device. The adhesive layer for optical films of the present invention can be applied to structures such as "polarizing film/adhesive layer for optical films", "polarizing film/adhesive layer for optical films/release film", "polarizing film/adhesive layer for optical films/retardation film/adhesive layer for optical films/release film".
Examples of the image display device of the present invention include, but are not limited to, a liquid crystal display device (liquid crystal panel), an organic EL display device (liquid crystal panel), a touch panel, and electronic paper. Hereinafter, an organic EL panel will be described as a representative example, and the present invention based on these concepts can be applied to other image display devices such as a liquid crystal panel.
As a material of the retardation film incorporated in the organic EL panel, a polycarbonate compound may be mentioned, and a material having reverse wavelength dispersion (birefringence increases as the wavelength is longer) is preferable. The polycarbonate compound is a resin containing a carbonate linkage (-O-CO-O-) in a polymer repeating unit, and various types such as aromatic type and aliphatic type are known as chemical structures contained between the carbonate linkages. The number of the repeating units may be one or two or more. Examples of the retardation film include 1/4. Lamda. Or 1/2. Lamda. (1/4 times or 1/2 times of the wavelength. Lamda.).
Among them, in recent years, in an organic EL panel, a circularly polarizing plate for preventing reflection of external light is required, and since the circularly polarizing plate has a structure in which two linear polarizing films and a 1/4 λ retardation film are stacked and the retardation film surface is bonded to the organic EL panel, there is a disadvantage that durability and foaming resistance are poor due to a polycarbonate-based resin.
The adhesive layer for an optical film of the present invention is used for bonding of a polarizing film and an organic EL panel, in which a 1/4 λ retardation film made of a polycarbonate resin is incorporated, to an optical film, and has an extremely high utility value.
As the polarizing film, the following structure is generally used: will contain iodine molecules (I) 2 ) As a polarizer (japanese: polarizing element), laminated on both sides thereof using triacetyl celluloseA resin film made of a material having excellent optical characteristics (such as transparency) such as cellulose (TAC), COP (cycloolefin polymer), acrylic resin, and polypropylene (PP) is used as a protective layer (also referred to as a protective film for a polarizer). Further, the resin film of the protective layer may also function as a retardation film.
As the organic EL panel, the following structures can be cited: the light emitting device has an Organic Light Emitting Diode (OLED) structure, and has a plurality of functional layers such as a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer formed and stacked between positive and negative electrodes. Examples of the electrode include a transparent electrode layer having light transmittance and an opaque metal electrode layer. A flexible organic EL panel can also be manufactured, and electrodes, wiring, functional layers, and the like can be formed on a flexible substrate such as a resin by foil, plating, printing, vapor deposition, sputtering, and the like.
Examples
The present invention will be specifically described below with reference to examples.
< preparation of acrylic Polymer >
[ example 1]
Nitrogen gas was introduced into a reaction apparatus equipped with a reaction vessel, a stirrer, a thermometer, a reflux condenser and a nitrogen gas inlet tube, and the air in the reaction vessel was replaced with nitrogen gas. Then, to the reaction vessel were added 70 parts by weight of 2-ethylhexyl acrylate, 30 parts by weight of t-butyl acrylate, 0.5 part by weight of 2-acryloyloxyethylhexahydrophthalic acid, and 0.3 part by weight of 8-hydroxyoctyl acrylate, together with 60 parts by weight of a solvent (ethyl acetate). Then, 0.1 part by weight of azobisisobutyronitrile as a polymerization initiator was added dropwise over 2 hours, and the reaction was carried out at 65 ℃ for 6 hours to obtain an acrylic polymer solution of example 1.
Examples 2 to 5 and comparative examples 1 to 3
Acrylic polymer solutions of examples 2 to 5 and comparative examples 1 to 3 were obtained in the same manner as in example 1 above, except that the kinds and addition ratios of the respective monomers constituting the acrylic polymer were as described in groups (a) to (C) of table 1.
< adhesive composition, adhesive layer for optical film, and production of adhesive film for optical film
[ example 1]
To the acrylic polymer solution of example 1 in the reaction vessel prepared as described above, 0.01 part by weight of 1, 3-bis (diglycidylaminomethyl) cyclohexane was added, and mixed with stirring to obtain the pressure-sensitive adhesive composition of example 1. The adhesive composition was coated on a release film (silicone resin-coated polyethylene terephthalate (PET) film) so that the thickness after drying was 10 μm, and then dried at 90 ℃ for 5 minutes to form an adhesive layer. Then, a release film subjected to release treatment is superimposed on the dried adhesive layer to form a layer structure composed of a release film/an adhesive layer for optical films/a release film. Further, the adhesive film for an optical film of example 1 was obtained by aging (maintenance) at 23 ℃ in an atmosphere of 50% RH for 7 days.
Examples 2 to 5 and comparative examples 1 to 3
Adhesive films for optical films of examples 2 to 5 and comparative examples 1 to 3 were obtained in the same manner as in example 1 above, except that the kinds and the addition ratios of the crosslinkable compounds were as shown in group (D) of table 1, and the thickness of the adhesive agent layer after drying was the value shown in table 3.
[ Table 1]
Figure BDA0003924588150000151
In table 1, the total amount of two or more monomers selected from the group consisting of (meth) acrylic acid alkyl ester monomer (a 1) having an alkyl group with a carbon number of C1 to C14, (meth) acrylic acid ester monomer (a 2) having an aromatic group, and nitrogen-containing vinyl monomer (a 3) in group (a) is 100 parts by weight (wherein one of the monomers belonging to group (a 1) is 51 parts by weight or more and 95 parts by weight or less, the total amount of one or more monomers selected from the group consisting of group (a 1) to group (a 3) is 5 parts by weight or more and 49 parts by weight or less, and the total amount thereof is 100 parts by weight). Further, the ratio of the addition from the group (B) to the group (D) is indicated by the numerical value of the part by weight enclosed in parentheses. The component (B) is a copolymerizable vinyl monomer having a carboxyl group, the component (C) is a copolymerizable vinyl monomer having a hydroxyl group, and the component (D) is a crosslinkable compound.
In addition, compound names corresponding to the abbreviations of the respective components shown in table 1 are shown in table 2. TETRAD (registered trademark) -C and TETRAD-X are trade names of Mitsubishi gas chemical, and CORONATE (registered trademark) HX and L are trade names of Tosoh corporation. TDI represents toluene diisocyanate, TMP represents trimethylolpropane, and HDI represents hexamethylene diisocyanate.
[ Table 2]
Figure BDA0003924588150000161
< test method and evaluation >
The release film (silicone resin-coated PET film) was peeled from the obtained adhesive films for optical films of examples 1 to 5 and comparative examples 1 to 3, and the adhesive layer for optical films was exposed to be used as various measurement and test samples.
< method for measuring gel fraction of adhesive layer for optical film >
The mass of the adhesive layer of the measurement sample was measured accurately, and then the sample was immersed in toluene at room temperature for 24 hours to elute dissolved components, and then the sample was filtered through a 200-mesh wire gauze. Then, the filtrate was dried at 100 ℃ for 1 hour, and the mass of the residue was accurately measured, and the gel fraction of the adhesive layer for optical film (crosslinked adhesive layer for optical film) was calculated by the following formula.
Gel fraction (%) = mass of insoluble portion (g)/mass of adhesive agent layer (g) × 100 in the adhesive agent layer for optical film
< method for testing durability >
Adhesive layers for optical films were transferred onto both surfaces of a retardation film (model number PURE-ACE WR, manufactured by teichoic corporation) made of a polycarbonate resin film, and further, a laminate of the optical film with the adhesive layer, which was obtained by laminating a polarizing film on one surface thereof, was laminated on alkali-free glass (EAGLE-XG, manufactured by Corning) and was autoclaved (50 ℃,5 atm × 20 min), and then stored in a dry atmosphere at 85 ℃ for 200 hours, and then taken out and placed in a dry atmosphere at 23 ℃ × 50 rh for 1 hour, and then the durability was judged by visual observation. The criteria for determination of visual confirmation are as follows.
O: the adhesive layer for an optical film was not peeled off or foamed.
And (delta): peeling and foaming occur in the adhesive layer for an optical film.
X: peeling and foaming occur in the entire adhesive layer for an optical film.
The evaluation results are shown in table 3. The "thickness of the adhesive layer for optical film" represents the thickness of the adhesive layer for optical film used in the durability test.
[ Table 3]
Figure BDA0003924588150000181
The adhesive layer for optical films of the present invention exposed from the adhesive film for optical films of examples 1 to 5 was prepared as a laminate imitating an organic EL panel in a structure of a polarizing film/adhesive layer for optical films/retardation film/adhesive layer for optical films/alkali-free glass, and was not foamed in durability after 200 hours at 85 ℃. That is, the adhesive layer for an optical film of the present invention has excellent heat resistance and durability when used for interlayer adhesion between a retardation film and a polarizing film or an organic EL panel.
In the adhesive film for an optical film of comparative example 1, in the acrylic polymer of the adhesive composition for an optical film, the amount of the carboxyl group-containing copolymerizable vinyl monomer used was too small, the Tg of the acrylic polymer was high, the gel fraction of the adhesive layer for an optical film was high, and partial foaming was observed in the adhesive layer for an optical film in the durability test.
The pressure-sensitive adhesive film for an optical film of comparative example 2 was not formed using a hydroxyl group-containing copolymerizable vinyl monomer in the acrylic polymer of the pressure-sensitive adhesive composition for an optical film, but instead, the amount of the carboxyl group-containing copolymerizable vinyl monomer was too large, and the reactivity between the acrylic polymer and the crosslinking agent was high, and the coating could not be performed because gelation had been performed before the coating (in this case, it can be said that the gel fraction after crosslinking was approximately 100%).
In the adhesive film for an optical film of comparative example 3, the gel fraction of the adhesive layer for an optical film was low, and significant foaming was observed in the durability test.
Thus, in the adhesive films for optical films of comparative examples 1 to 3, the adhesive layer for optical films could not have durability.

Claims (8)

1. An adhesive composition for an optical film, which comprises an acrylic polymer and a crosslinkable compound, characterized in that,
the acrylic polymer is composed of a copolymer which is copolymerized by the following components and has Tg of-60 ℃ to-30 ℃: 100 parts by weight of the total amount of (A) at least two or more monomers selected from the group consisting of (meth) acrylic acid alkyl ester monomers (a 1) having an alkyl group with carbon atoms of C1 to C14 and (meth) acrylic acid ester monomers (a 2) having an aromatic group, (B) 0.1 to 10.0 parts by weight of a copolymerizable vinyl monomer having a carboxyl group, and (C) 0.05 to 0.5 parts by weight of a copolymerizable vinyl monomer having a hydroxyl group,
wherein one of the monomers (a 1) is 51 to 95 parts by weight, the total amount of the other or more monomers selected from the group consisting of the monomers (a 1) and (a 2) is 5 to 49 parts by weight, and the total amount thereof is 100 parts by weight,
the crosslinkable compound is an epoxy compound having 2 or more functions.
2. The pressure-sensitive adhesive composition for optical films according to claim 1, wherein the crosslinkable compound is contained in an amount of 0.001 to 0.5 part by weight based on 100 parts by weight of the total amount of at least two or more monomers selected from the group consisting of the monomers (a 1) and (a 2).
3. The adhesive composition for optical films according to claim 1 or 2,
the carboxyl group-containing copolymerizable vinyl monomer (B) is at least one selected from the group consisting of (meth) acrylic acid, carboxyethyl (meth) acrylate, carboxypentyl (meth) acrylate, 2- (meth) acryloyloxyethyl hexahydrophthalic acid, 2- (meth) acryloyloxyethyl phthalic acid, 2- (meth) acryloyloxyethyl succinic acid, 2- (meth) acryloyloxyethyl maleic acid, carboxypolycaprolactone mono (meth) acrylate, and 2- (meth) acryloyloxyethyl tetrahydrophthalic acid,
the hydroxyl group-containing copolymerizable vinyl monomer (C) is at least one selected from the group consisting of 8-hydroxyoctyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, N-hydroxy (meth) acrylamide, N-hydroxymethyl (meth) acrylamide and N-hydroxyethyl (meth) acrylamide.
4. The adhesive composition for optical films according to claim 1 or 2,
the (a 1) alkyl (meth) acrylate monomer having an alkyl group with carbon atoms of C1 to C14 is at least one compound selected from the group consisting of methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, pentyl (meth) acrylate, isoamyl (meth) acrylate, hexyl (meth) acrylate, isohexyl (meth) acrylate, heptyl (meth) acrylate, isoheptyl (meth) acrylate, octyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, nonyl (meth) acrylate, isononyl (meth) acrylate, decyl (meth) acrylate, isodecyl (meth) acrylate, undecyl (meth) acrylate, isoundecyl (meth) acrylate, dodecyl (meth) acrylate, isododecyl (meth) acrylate, tridecyl (meth) acrylate, isotridecyl (meth) acrylate, tetradecyl (meth) acrylate, and isotetradecyl (meth) acrylate,
the (a 2) aromatic group-containing (meth) acrylate monomer is at least one selected from the group consisting of benzyl (meth) acrylate, naphthyl (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxybutyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, 2- (1-naphthyloxy) ethyl (meth) acrylate, 6- (1-naphthyloxy) hexyl (meth) acrylate, 6- (2-naphthyloxy) hexyl (meth) acrylate, 8- (1-naphthyloxy) octyl (meth) acrylate, and 8- (2-naphthyloxy) octyl (meth) acrylate.
5. An adhesive film for optical films, which is characterized in that the adhesive composition for optical films according to any one of claims 1 to 4 is coated on one surface of a release film to form an adhesive layer for optical films, and which has a structure of release film/adhesive layer for optical films/release film.
6. An adhesive film for optical films, characterized in that an adhesive layer for optical films obtained by crosslinking the adhesive composition for optical films according to any one of claims 1 to 4 is laminated on one surface of a substrate.
7. An image display device, wherein the adhesive composition for optical films according to any one of claims 1 to 4 is crosslinked to form an adhesive layer for optical films, and the adhesive layer is used for bonding optical films.
8. A polarizing plate with an adhesive layer, wherein the adhesive layer for an optical film obtained by crosslinking the adhesive composition for an optical film according to any one of claims 1 to 4 is used.
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