TWI454551B - An optical film with an adhesive and an optical laminate using the same - Google Patents

Description

Optical film with adhesive and optical laminate using the same

The present invention relates to an optical film forming an adhesive layer. As the optical film to be the object of the present invention, for example, a polarizing plate or a retardation film can be exemplified. The present invention also relates to an optical laminate for liquid crystal display using an optical film forming the adhesive layer.

The polarizing plate is mounted on the liquid crystal display device, and the transparent protective film is laminated on both surfaces of the polarizing element, and an adhesive layer is formed on the surface of at least one of the protective films, and the adhesive film is adhered to the peeling film to be circulated. Widely used. Further, a retardation film laminated on the polarizing plate in which the protective film is adhered to both surfaces of the polarizing element is used as an elliptically polarizing plate, and an adhesive layer/release film is also attached to the retardation film side. Further, an adhesive layer/release film is also attached to the surface of the retardation film. Before being adhered to the liquid crystal cell, the release film is peeled off from the polarizing plate, the ellipsometer, the retardation film, or the like, and adhered to the liquid crystal cell through the exposed adhesive layer. When the polarizing plate, the elliptically polarizing plate, or the retardation film is peeled off and adhered to the liquid crystal cell, static electricity is generated, and development countermeasures are expected.

In the polarizing plate in which a protective film is laminated on the surface of the polarizing element film and the adhesive is provided on the surface of the protective film, the use of the polarizing plate on the surface of the protective film is disclosed in Japanese Laid-Open Patent Publication No. Hei 6-313807 (Patent Document 1). The composition of the ion conductive composition composed of the electrolyte salt and the organic polyoxyalkylene and the acrylic copolymer is used as an adhesive. By using the adhesive, although the antistatic property can be exhibited, the performance is not necessarily sufficient, and the adhesion durability is insufficient.

On the other hand, JP-A-2004-536940 (Patent Document 2) discloses that an organochlorine-based antistatic agent is blended in a pressure-sensitive adhesive (adhesive) to impart antistatic properties to the adhesive. In the adhesive or the like, a salt composed of a quaternary ammonium cation having a total carbon number of 4 to 20 and an anion containing a fluorine atom is contained in the adhesive to impart electrical conductivity. Japanese Patent Publication No. 2006-307238 (Patent Document 4) discloses that an ionic liquid which becomes a liquid at room temperature (25 ° C) is contained in an adhesive to achieve antistatic. However, when the polarizing plate coated with the adhesive is left for a long period of time, the antistatic property may be deteriorated due to the change with time. Generally speaking, the circulation and storage period of the polarizing plate can be freely produced for up to six months. Therefore, it is required to maintain antistatic performance between the customers before use.

Further, the optical film with an adhesive as described above is adhered to the liquid crystal cell as a liquid crystal display device on the side of the adhesive layer, but is placed in a high temperature or high temperature and high humidity condition in this state, and is repeatedly heated and cooled. Since foaming occurs in the adhesive layer accompanying the change in the size of the optical film, floating or peeling occurs between the optical film and the adhesive layer, or between the adhesive layer and the liquid crystal cell, it is also required to be produced. These defects are excellent in durability. Further, when exposed to a high temperature, the residual stress distribution caused by the optical film becomes uneven, and as a result of stress concentration at the outer periphery of the optical film, it is called white at the outer peripheral portion when it is displayed in black. White phenomenon, but there are cases of uneven color, so it is also required to suppress such whitening or color unevenness. Furthermore, when the optical film with the adhesive is adhered to the liquid crystal cell, the adhesive film is accompanied by the optical layer from the temporary peeling of the optical film to the re-adhesion of the new film in the case of incomplete adhesion. The film is peeled off together, and the adhesive does not remain on the liquid crystal cell glass, and the so-called reworkability such as blurring does not occur.

JP-A-2007-138056 (Patent Document 5) describes the copolymerization of a monomer containing an aromatic ring in an alkyl acrylate to obtain a ratio of a weight average molecular weight (Mw) to a number average molecular weight (Mn) of the obtained resin (Mw). /Mn) indicates a method in which the molecular weight distribution is expanded to 10 to 50, thereby suppressing light leakage. Although the light leakage can be alleviated by using the adhesive, it is not sufficient, and the expansion of the molecular weight distribution may cause foaming under high temperature conditions.

Prior technical literature Patent literature

Patent Document 1: JP-A-6-313807

Patent Document 2: Japanese Patent Publication No. 2004-536940

Patent Document 3: JP-A-2004-114665

Patent Document 4: JP-A-2006-307238

Patent Document 5: JP-A-2007-138056

An object of the present invention is to provide an adhesive for an adhesive layer which is provided on the surface of an optical film and which is excellent in antistatic property and which does not easily change in antistatic property over time, and which is excellent in suppression of large-scale whitening. Optical film. As a result of intensive research to solve the problem, the present inventors have found that an acrylic resin containing a structural unit derived from an unsaturated monomer containing an acrylate as a main component and having an aromatic ring in a molecule, and a specific one are prepared. The ionic compound is provided on an optically thin surface as an adhesive layer, whereby an optical film with an adhesion preventing agent, an antistatic property, and an excellent durability is obtained, and the present invention has been completed.

That is, the present invention is an optical film with an adhesive attached to an optical film of an adhesive layer forming an adhesive layer on at least one side of the optical film, characterized in that the adhesive layer is an adhesive containing the following components. The composition is formed, and the adhesive layer has a gel fraction of 70 to 99% by weight: 100 parts by weight of (A) a weight average molecular weight Mw of 1,000,000 to 2,000,000, and a molecular weight distribution Mw/Mn (weight average molecular weight ( An acrylic resin having a ratio of Mw) to a number average molecular weight (Mn) of 3 to 7 which is a copolymer obtained from a monomer mixture of the following (A-1) to (A-3), 80 to 96% by weight (A-1) (meth) acrylate represented by the following formula (I):

[Chemical 1]

(wherein R ₁ represents a hydrogen atom or a methyl group, R ₂ represents an alkyl group having 1 to 14 carbon atoms which may be substituted by an alkoxy group having 1 to 10 carbon atoms), and 3 to 15% by weight of (A-2) An unsaturated monomer having an olefinic double bond and at least one aromatic ring in the molecule, and 0.1 to 5% by weight of (A-3) an unsaturated monomer having a polar functional group; and 0.2 to 8 parts by weight of (B) having An organic compound having an ionic compound having a melting point of 80 ° C or less; and 0.01 to 5 parts by weight of the (C) crosslinking agent.

Further, according to the present invention, there is provided an optical laminate in which the optical film of the above-mentioned adhesive is laminated on the glass substrate with the adhesive layer side.

In the present invention, by using an acrylic resin (A) having an olefinic double bond and at least one aromatic ring unsaturated monomer (A-2) as a constituent component, and having an organic cation and having a melting point of 80 ° C The composition of the following ionic compound (B) acts as an adhesive composition for forming an adhesive layer, and since it can prevent optical defects caused by uneven stress distribution, it can suppress whitening and can effectively suppress charging of optical members. Even if it is stored for a long time after production, it can maintain the initial antistatic performance.

Moreover, in the case where the optical film with the adhesive of the present invention is laminated on the glass substrate temporarily, if there is any mismatch, even if the adhesive is peeled off from the glass substrate at the same time, the surface of the peeled glass substrate is also It is rare that the paste remains or is blurred, and it can be used again as a glass substrate, and it is excellent in reworkability.

Further, the optical film with an adhesive of the present invention can be effectively prevented as an optical laminate by using an acrylic resin (A) having a molecular weight distribution (Mw/Mn) of 3 to 7 as an adhesive composition for forming an adhesive layer. When it is white, it can also prevent defects such as foaming under high temperature conditions. Furthermore, by making the gel fraction of the adhesive layer 70 to 99% by weight, the durability of the adhesive layer can be improved, and the optical film of the adhesive can be adhered to the glass substrate of the liquid crystal cell. In the state, the change in appearance when subjected to tests such as heat resistance, moist heat resistance, and impact resistance can be suppressed.

The optical film to which the adhesive is applied is laminated, for example, on a glass substrate of a liquid crystal cell to obtain an optical laminate for liquid crystal display. The optical laminate can absorb and alleviate stress caused by dimensional changes of the optical film and the glass substrate under wet heat conditions, thereby reducing local stress concentration and suppressing floating or peeling of the adhesive layer on the glass substrate. .

The invention is described in detail below. The optical film with an adhesive of the present invention is such that an adhesive layer is formed on at least one side of the optical film, and the adhesive composition forming the adhesive layer is formed of a composition comprising the following components:

(A) acrylic resin,

(B) an ionic compound having an organic cation and having a melting point of 80 ° C or less, and

(C) Crosslinker.

First, each component constituting the adhesive composition will be described.

[Acrylic Resin (A)]

In the optical film with an adhesive according to the present invention, the acrylic resin (A) used in the adhesive composition is a structural unit derived from the (meth) acrylate represented by the above formula (I) as a main component, but specifically In addition to the structural units derived from (meth) acrylate, the structural unit derived from an unsaturated monomer having an olefinic double bond and at least one aromatic ring in the molecule is also derived from having a free carboxyl group. The unsaturated monomer having a polar functional group such as a heterocyclic group represented by a hydroxyl group, an amine group or an epoxy ring is preferably one having a structural unit derived from a (meth)acrylic compound having a polar functional group. Here, (meth)acrylic means any of acrylic acid or methacrylic acid. In addition, "(meth)" when it is called (meth)acrylate etc. is also the same meaning.

In the above formula (I) which is a main structural unit of the acrylic resin (A), R ₁ is a hydrogen atom or a methyl group, and R ₂ is an alkyl group having 1 to 14 carbon atoms. The hydrogen atom in each of the alkyl groups represented by R ₂ may be substituted by an alkoxy group having 1 to 10 carbon atoms.

In the (meth) acrylate (A-1) represented by the formula (I), R ₂ is an unsubstituted alkyl group, and specifically exemplified as methyl acrylate, ethyl acrylate, propyl acrylate, acrylic acid. a linear alkyl acrylate of n-butyl ester, n-octyl acrylate or undecyl acrylate; a branched alkyl acrylate such as isobutyl acrylate, 2-ethylhexyl acrylate or isooctyl acrylate; a linear alkyl methacrylate of methyl acrylate, ethyl methacrylate, propyl methacrylate, n-butyl methacrylate, n-octyl methacrylate or undecyl methacrylate; Isobutyl acrylate, 2-ethylhexyl methacrylate, branched methacrylate of isooctyl methacrylate, and the like.

In the above, n-butyl acrylate is preferable. Specifically, among all the monomers constituting the acrylic resin (A), n-butyl acrylate is 50% by weight or more, and the above (meth) acrylate (A) is satisfied. -1) Relevant regulations.

When R ₂ is an alkoxy-substituted alkyl group, that is, when R ₂ is an alkoxyalkyl group, the (meth) acrylate represented by the formula (I) is specifically exemplified as 2-methoxyB acrylate. Ester, ethoxymethyl acrylate, 2-methoxyethyl methacrylate, ethoxymethyl methacrylate, and the like.

These (meth) acrylates may be used singly or in combination of plural kinds and copolymerized.

The unsaturated monomer (A-2) having an olefinic double bond and at least one aromatic ring in the molecule preferably has a (meth) acrylonitrile group as a base containing an olefinic double bond. Examples thereof are benzyl (meth) acrylate, neopentyl glycol benzoate (meth) acrylate, etc., but are preferably unsaturated monomers represented by the following formula (II):

[Chemical 2]

In the formula, R ₃ represents a hydrogen atom or a methyl group, n is an integer of 1 to 8, and R ₄ represents a hydrogen atom, an alkyl group, an aralkyl group or an aryl group. When R ₄ is an alkyl group, the carbon number thereof may be about 1 to 9. Similarly, when it is an aralkyl group, the carbon number may be about 7 to 11, and when it is an aryl group, the carbon number may be 6 to 10. about.

The alkyl group having 1 to 9 carbon atoms is exemplified by a methyl group, a butyl group or a fluorenyl group, and the aralkyl group having a carbon number of 6 to 11 is exemplified by a benzyl group, a phenethyl group, a naphthylmethyl group or the like, and the carbon number is 6 to 10. Examples of the aryl group are a phenyl group, a tolyl group, a naphthyl group and the like.

Specific examples of the unsaturated monomer of the formula (II) include 2-phenoxyethyl (meth)acrylate, 2-(2-phenoxyethoxy)ethyl (meth)acrylate, and epoxy B. Alkyl-modified (meth) acrylate of nonylphenol, 2-(o-phenylphenoxy)ethyl (meth)acrylate, and the like. The unsaturated monomers having one olefinic double bond and at least one aromatic ring in the molecule may be used singly or in combination of plural kinds.

Among these, it is preferred to use 2-phenoxyethyl (meth)acrylate or 2-(o-phenylphenoxy)ethyl (meth)acrylate as the aromatic ring constituting the acrylic resin (A). One of the unsaturated monomers (A-2).

Examples of the unsaturated functional monomer (A-3) having a polar functional group may, for example, be an unsaturated monomer having a free carboxyl group such as acrylic acid, methacrylic acid or β-carboxyethyl acrylate; for example, (meth)acrylic acid 2- Hydroxyethyl ester, 2-hydroxypropyl (meth)acrylate, 2- or 3-chloro-2-hydroxypropyl (meth)acrylate, diethylene glycol mono(meth)acrylate having hydroxyl group unsaturation Monomer; such as acryloyl morpholine, vinyl caprolactam, N-vinyl-2-pyrrolidone, tetrahydrofurfuryl (meth) acrylate, caprolactone modified tetrahydrofurfuryl acrylate, (meth)acrylic acid 3,4-epoxycyclohexyl methyl ester, glycidyl (meth)acrylate, 2,5-dihydrofuran unsaturated monomer having a heterocyclic group; such as (meth)acrylic acid An unsaturated monomer having an amine group different from the heterocyclic ring of N,N-dimethylaminoethyl ester. These polar functional group-containing unsaturated monomers may be used singly or in combination of plural kinds.

Among these, the polar functional group of the unsaturated monomer (A-3) is preferably a free carboxyl group, a hydroxyl group, an amine group or an epoxy group. Among them, an unsaturated monomer having a hydroxyl group is preferably used as one of the polar functional group-containing unsaturated monomers (A-3) constituting the acrylic resin (A). Further, in addition to the unsaturated monomer having a hydroxyl group, it is also effective to use an unsaturated monomer having another polar functional group, for example, an unsaturated monomer having a free carboxyl group.

The content of the (meth) acrylate (A-1) represented by the above formula (I) in the acrylic resin (A) is 80 to 96% by weight, preferably 82% by weight or more, more preferably 85% by weight. The above is preferably 94% by weight or less, more preferably 92% by weight or less. The content of the unsaturated monomer (A-2) having an olefinic double bond and at least one aromatic ring in the molecule is from 3 to 15% by weight, preferably from 5% by weight or more, more preferably in the acrylic resin (A). It is 5.5% by weight or more, more preferably 7% by weight or more, still more preferably 12% by weight or less, more preferably 9.9% by weight or less, still more preferably 9.5% by weight or less, still more preferably 9% by weight or less. The content of the unsaturated functional monomer (A-3) having a polar functional group in the acrylic resin (A) is 0.1 to 5% by weight, preferably 0.5% by weight or more, and more preferably 3% by weight or less.

The acrylic resin (A) used in the present invention also contains (meth) acrylate (A-1) represented by the above formula (I) in addition to the above, having an olefinic double bond and at least one aromaticity in the molecule. A structural monomer of a monomer other than the cyclic unsaturated monomer (A-2) and the unsaturated functional monomer (A-3) having a polar functional group. Examples of such an example are a structural unit derived from a (meth) acrylate having an alicyclic structure in a molecule, a structural unit derived from a styrene monomer, a structural unit derived from a vinyl monomer, and a molecular derived molecule. A structural unit having a plurality of (meth) acrylonitrile groups therein.

The alicyclic structure is a cycloalkane structure having a carbon number of usually 5 or more, preferably about 5 to 7. Specific examples of the acrylate having an alicyclic structure are exemplified isobornyl acrylate, cyclohexyl acrylate, dicyclopentanyl acrylate, cyclododecyl acrylate, methylcyclohexyl acrylate, and trimethylcyclohexyl acrylate. , t-butylcyclohexyl acrylate, cyclohexyl α-ethoxyacrylate, cyclohexyl phenyl acrylate, and the like. Specific examples of the methacrylate having an alicyclic structure are exemplified isobornyl methacrylate, cyclohexyl methacrylate, dicyclopentyl methacrylate, cyclododecyl methacrylate, and methacrylic acid. Cyclohexyl ester, trimethylcyclohexyl methacrylate, t-butylcyclohexyl methacrylate, cyclohexyl phenyl methacrylate, and the like.

Examples of the styrene monomer include styrene, such as methyl styrene, dimethyl styrene, trimethyl styrene, ethyl styrene, diethyl styrene, triethyl styrene, and c. Alkyl styrene of styrene, butyl styrene, hexyl styrene, heptyl styrene, octyl styrene; such as fluorostyrene, chlorostyrene, bromostyrene, dibromostyrene, iodine styrene The halogenated styrene; further examples are nitrostyrene, ethyl styrene styrene, methoxy styrene, divinyl benzene, and the like.

Examples of the vinyl monomer are, for example, vinyl acetate, vinyl propionate, vinyl butyrate, vinyl 2-ethylhexanoate, vinyl acetate of lauric acid; such as ethylene chloride or ethylene bromide. A halogenated ethylene; such as a vinylidene halide of vinylidene chloride; a nitrogen-containing aromatic vinyl such as vinylpyridine, vinylpyrrolidone or vinylcarbazole; such as butadiene, isoprene, and chloroprene The conjugated diene monomer of the alkene; furthermore, acrylonitrile, methacrylonitrile or the like can be exemplified.

Examples of the monomer having a plurality of (meth) acrylonitrile groups in the molecule can be exemplified by, for example, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate. 1,9-nonanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate a monomer having two (meth)acrylonitrile groups in the molecule of tripropylene glycol di(meth)acrylate; for example, trimethylolpropane tri(meth)acrylate has three (methyl) groups in the molecule. A monomer of propylene fluorenyl.

(meth) acrylate (A-1) represented by the above formula (I), an unsaturated monomer (A-2) having an olefinic double bond and at least one aromatic ring in the molecule, and a polar functional group The monomers other than the unsaturated monomer (A-3) may be used singly or in combination of two or more. The structural unit derived from the monomers other than the above (A-1) to (A-3) usually contains 0 to 20 parts by weight, preferably 0 to 10, based on 100 parts by weight of the nonvolatile portion of the acrylic resin (A). The proportion by weight.

The active ingredient of the adhesive may be one or more types including the (meth) acrylate (A-1) derived from the formula (I) as described above, having one olefinic double bond and at least one aromatic group in the molecule. The acrylic resin of the cyclic unsaturated monomer (A-2) and the structural unit of the unsaturated functional monomer (A-3) having a polar functional group. In addition, in the acrylic resin, an acrylic resin different from the above may be used, and specifically, for example, an acrylic resin having a structural unit derived from the (meth) acrylate of the formula (I) and containing no polar functional group may be used. And a (meth) acrylate (A-1) represented by the formula (I), an unsaturated monomer having an olefinic double bond and at least one aromatic ring in the molecule (A-2), and a polar functional group The acrylic resin having a structural unit of the unsaturated monomer (A-3) preferably accounts for 80% by weight or more, more preferably 90% by weight or more, based on the total monomers of the acrylic resin.

An unsaturated monomer (A-2) comprising an (meth) acrylate (A-1) represented by the formula (I), an olefinic double bond in the molecule and at least one aromatic ring, and a polar functional group The acrylic resin (A) of the copolymer obtained from the monomer mixture of the unsaturated monomer (A-3) is an average molecular weight (Mw) of 100 parts by weight of a standard styrene by a gel permeation chromatography (GPC). Within the range of 10,000 to 2 million. When the weight average molecular weight converted to standard polystyrene is 1,000,000 or more, the adhesion under high temperature and high humidity is improved, and the possibility of floating or peeling between the glass substrate and the adhesive layer tends to be low, and It is preferable to have a tendency to improve the reworkability. Further, when the weight average molecular weight is 2,000,000 or less, even if the size of the optical film adhered to the adhesive layer changes, since the adhesive layer changes with the change of the size, the brightness and the center of the peripheral portion of the liquid crystal cell There is no difference in brightness between the parts, so there is a tendency to suppress whitening or uneven color. The molecular weight distribution expressed by the ratio of the weight average molecular weight (Mw) to the number average molecular weight (Mn) (Mw/Mn) is in the range of 3 to 7.

Further, the acrylic resin (A) exhibits adhesiveness, and the glass transition temperature thereof is preferably in the range of -10 to -60 °C. The glass transition temperature of the resin can usually be measured by a differential scanning calorimeter.

The acrylic resin (A) constituting the adhesive layer can be produced by various methods such as a solution polymerization method, an emulsion polymerization method, a bulk polymerization method, or a suspension polymerization method. In the production of the acrylic resin, a polymerization initiator is usually used. The polymerization initiator is used in an amount of about 0.001 to 5 parts by weight based on 100 parts by weight of the total of all the monomers used in the production of the acrylic resin.

As the polymerization initiator, a thermal polymerization initiator or a photopolymerization initiator is used. As the photopolymerization initiator, for example, 4-(2-hydroxyethoxy)phenyl(2-hydroxy-2-propyl) ketone or the like can be exemplified. The thermal polymerization initiator can be exemplified by, for example, 2,2'-azobisisobutyronitrile, 2,2'-azobis(2-methylbutyronitrile), 1,1'-azobis (cyclohexyl) Alkan-1--1-carbonitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobis(2,4-dimethyl-4-methoxy An azo compound of valeronitrile), dimethyl-2,2'-azobis(2-methylpropionate), 2,2'-azobis(2-hydroxymethylpropionitrile); Lauryl peroxide, tert-butyl hydroperoxide, benzammonium peroxide, tert-butylperoxybenzoate, cumyl hydroperoxide, diisopropylperoxydicarbonate, two Propylperoxydicarbonate, tert-butylperoxy neodecanoate, tert-butylperoxyacetate, (3,5,5-trimethylhexyl) peroxide Organic peroxides; such as potassium persulfate, ammonium persulfate, inorganic peroxides of hydrogen peroxide, and the like. Further, a redox initiator such as a peroxide and a reducing agent may be used in combination as a polymerization initiator.

The method for producing an acrylic resin is preferably a solution polymerization method among the methods shown above.

For example, when the solution polymerization method is used, the desired monomer and the organic solvent may be mixed, and a thermal polymerization initiator is added under a nitrogen atmosphere, and the mixture is stirred at about 40 to 90 ° C, preferably at about 60 to 80 ° C. 10 hours or so. Further, in order to control the reaction, the monomer or the thermal polymerization initiator may be added continuously or intermittently in the polymerization, or may be added in a state of being dissolved in an organic solvent. Here, as the organic solvent, for example, an aromatic hydrocarbon such as toluene or xylene; an ester such as ethyl acetate or butyl acetate; an aliphatic alcohol such as propanol or isopropanol; such as acetone or methyl ethyl; Ketones, ketones of methyl isobutyl ketone, and the like.

[Ionic compound (B)]

In the present invention, in addition to the above acrylic resin (A), an ionic compound (B) having a melting point of 80 ° C or lower is also used. The ionic compound (B) has an organic cation.

The cation component constituting the ionic compound (B) is not particularly limited as long as it is an organic cation satisfying an ionic compound having a melting point of 80 ° C or lower. For example, it is an imidazolium cation, a pyridinium cation, an ammonium cation, a phosphonium cation, a phosphonium cation, etc., but when used in an adhesive layer of an optical film, it is difficult to charge when peeling off the release film provided thereon. Preferably, the pyridinium cation or the imidazolium cation is used. The molecular weight of the ionic compound (B) is not particularly limited, and is, for example, preferably 700 or less, more preferably 500 or less.

On the other hand, in the ionic compound (B), the anion component which is a relative ion of the cation component is not particularly limited as long as it satisfies the ionic compound having a melting point of 80 ° C or lower, and may be an inorganic anion or an organic anion. For example, the following may be mentioned.

Chloride anion [Cl ^- ], bromine anion [Br ^- ], iodine anion [I ^- ], tetrachloroaluminate anion [AlCl ₄ ^- ], heptachlorodisuccinate anion [Al ₂ Cl ₇ ^- ], tetrafluoroborate Anion [BF ₄ ^- ], hexafluorophosphate anion [PF ₆ ^- ], perchlorate anion [ClO ₄ ^- ], nitrate anion [NO ₃ ^- ], acetate anion [CH ₃ COO ^- ], trifluoroacetic acid Root anion [CF ₃ COO ^- ], methanesulfonate anion [CH ₃ SO ₃ ^- ], trifluoromethanesulfonate anion [CF ₃ SO ₃ ^- ], p-toluenesulfonate anion [p-CH ₃ C ₆ H ₄ SO ₃ ^- ], bis(trifluoromethanesulfonyl) quinone imine [(CF ₃ SO ₂ ) ₂ N ^- ], ginseng (trifluoromethanesulfonyl) methoxide anion [(CF ₃ SO ₂ ) ₃ C ^- ], hexafluoroarsenate anion [AsF ₆ ^- ], hexafluoroantimonate anion [SbF ₆ ^- ], hexafluoroantimonate anion [NbF ₆ ^- ], hexafluoroantimonate anion [TaF ₆ ^- ], Methyl phosphite anion [(CH ₃ ) ₂ POO ^- ], (poly) hydrogen fluoride hydrofluoride anion [F(HF) _n ^- ] (n is about 1~3), dicyanamide anion [(CN) ₂ N ^- ], thiocyanate anion [SCN ^- ], perfluorobutane sulfonate anion [C ₄ F ₉ SO ₃ ^- ] bis(pentafluoroethanesulfonyl) quinone imine [(C ₂ F ₅ SO ₂ ) ₂ N ^- ] perfluorobutyrate anion [C ₃ F ₇ COO ^- ] (trifluoro Methanesulfonyl) (trifluoromethanecarbonyl) quinone imine [[CF ₃ SO ₂ )(CF ₃ CO)N ^- ].

In particular, the anion component containing a fluorine atom is particularly suitable because it is an ionic compound which can obtain excellent antistatic properties, and among them, a hexafluorophosphate anion or a bis(trifluoromethanesulfonyl) anthracene anion is preferred. .

Specific examples of the ionic compound used in the present invention can be appropriately selected from the combination of the above cationic component and anionic component. Specific compounds of the combination of the cationic component and the anionic component are listed below.

N-hexylpyridinium hexafluorophosphate, N-octylpyridinium hexafluorophosphate, N-butyl-4-methylpyridinium hexafluorophosphate, N-octyl-4-methylpyridinium hexafluorophosphate Phosphate, N-methyl-4-hexylpyridinium hexafluorophosphate, N-butyl-N-methylpyrrolidinium hexafluorophosphate, 1-ethyl-3-methylimidazolium hexafluorophosphate , tetrabutylammonium hexafluorophosphate, 1-ethyl-3-methylimidazolium p-toluenesulfonate, tetrabutylammonium p-toluenesulfonate, 1-butyl-3-methylimidazolium Methanesulfonate, (2-hydroxyethyl)trimethylammonium dimethyl phosphite, (2-hydroxyethyl)trimethylammonium bis(trifluoromethanesulfonyl) quinone imine, N-A 4-ylhexylpyridinium bis(trifluoromethanesulfonyl) quinone imine, N-hexyl-4-methylpyridinium bis(trifluoromethanesulfonyl) quinone imine, tetrahexylammonium bis(trifluoro Methanesulfonyl) quinone imine, trioctylmethylammonium bis(trifluoromethanesulfonyl) quinone imine, tributylmethylammonium bis(trifluoromethanesulfonyl) ruthenium, and the like.

These plasma compounds (B) may be used alone or in combination of two or more. Examples of the ionic compound (B) are not limited to the above-listed materials.

As described above, the ionic compound (B) having a melting point of 80 ° C or less can impart antistatic properties to the adhesive layer formed of the composition containing the acrylic resin (A), and can effectively maintain physical properties as an adhesive. When the ionic compound has a too high melting point, the compatibility with the acrylic resin (A) is deteriorated. Therefore, it is preferred to have a melting point of 80 ° C or lower and further 70 ° C or lower. Further, from the viewpoint of the long-term stability of the antistatic property, the ionic compound (B) preferably has a melting point of 30 ° C or more and further 35 ° C or more. Accordingly, the ionic compound (B) which is solid at normal temperature (25 ° C) can maintain the antistatic property of the adhesive layer for a longer period of time than the ionic compound which is liquid at normal temperature.

The ionic compound (B) contains 0.2 to 8 parts by weight with respect to 100 parts by weight of the nonvolatile matter of the above acrylic resin (A) (the total amount of the structural units derived from the above A-1, A-2 and A-3, respectively) The proportion of the share. When the ionic compound (B) is contained in an amount of 0.2 part by weight or more based on 100 parts by weight of the nonvolatile content of the acrylic resin (A), it is preferably improved in antistatic property, and when the amount is 8 parts by weight or less, It is preferable to be easy to maintain durability. The amount of the ionic compound (B) is preferably 0.5 parts by weight or more and 3 parts by weight or less based on 100 parts by weight of the nonvolatile matter of the acrylic resin (A).

[Crosslinking agent (C)]

In the above acrylic resin (A) and ionic compound (B), the crosslinking agent (C) can be further formulated to form an adhesive composition. The crosslinking agent (C) is a compound having a functional group obtained by crosslinking at least two structural units derived from an unsaturated monomer derived from a specific polar functional group contained in the acrylic resin (A), and specifically exemplified Examples of the isocyanate compound, the epoxy compound, the metal chelate compound, and the aziridine compound.

The isocyanate compound is a compound having at least two isocyanate groups (-NCO) in the molecule, and is exemplified by, for example, toluene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, xylene diisocyanate, and hydrogenated xylene diisocyanate. , diphenylmethane diisocyanate, hydrogenated diphenylmethane diisocyanate, naphthalene diisocyanate, triphenylmethane triisocyanate, and the like. Further, an adduct obtained by reacting the isocyanate compound with a polyhydric alcohol such as glycerin or trimethylolpropane, or a dimer or a trimer of the isocyanate compound may be used as a crosslinking agent in the adhesive. . Two or more kinds of isocyanate compounds may be used in combination.

The epoxy compound is a compound having at least two epoxy groups in the molecule, and examples thereof include, for example, bisphenol A type epoxy resin, ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, and glycerin II. Glycidyl ether, glycerol triglycidyl ether, 1,6-hexanediol diglycidyl ether, trimethylolpropane triglycidyl ether, N,N-diglycidylaniline, N,N,N' , N'-tetraglycidyl-m-xylylenediamine, 1,3-bis(N,N-diglycidylaminomethyl)cyclohexane. Two or more epoxy compounds may be used in combination.

The metal chelating agent compound is exemplified by, for example, coordinating ethyl acetoacetate or ethyl acetoxyacetate on a polyvalent metal such as aluminum, iron, copper, zinc, tin, titanium, nickel, ruthenium, magnesium, osmium, chromium, and zirconium. Compounds and the like.

The aziridine-based compound is a compound having at least two skeletons of a three-membered ring composed of one nitrogen atom and two carbon atoms in the molecule, for example, diphenylmethane-4. 4'-bis(1-aziridine carboxamide), toluene-2,4-bis(1-aziridine carboxamide), tri-ethyl melamine, m-xylylenediyl-1-( 2-methylaziridine), gin-1-aziridine phosphine oxide, hexamethylene-1,6-bis(1-aziridine carboxamide), trimethylolpropane-tri-beta - aziridine propionate, tetramethylolmethane-tri-beta-aziridine propionate, and the like.

Among these crosslinking agents, an isocyanate compound, particularly xylene diisocyanate, toluene diisocyanate or hexamethylene diisocyanate, or a reaction of the isocyanate compound with a polyol such as glycerin or trimethylolpropane The adduct or the isocyanate compound may be used as a dimer or a trimer, or a mixture of such isocyanate compounds, or the like. When the polar functional group-containing unsaturated monomer (A-3) has a polar functional group selected from a free carboxyl group, a hydroxyl group, an amine group and an epoxy ring, it is preferred to use an isocyanate compound as at least a crosslinking agent (C). One. Preferred isocyanate compounds are, for example, toluene diisocyanate, an adduct obtained by reacting toluene diisocyanate with a polyol, a dimer of tolylene diisocyanate, a terpolymer of toluene diisocyanate, or hexamethylene diisocyanate. An adduct obtained by reacting hexamethylene diisocyanate with a polyhydric alcohol, a dimer of hexamethylene diisocyanate, and a trimer of hexamethylene diisocyanate.

The crosslinking agent (C) is formulated in an amount of 0.01 to 5 parts by weight based on 100 parts by weight of the acrylic resin (A). The amount of the crosslinking agent (C) is preferably from 0.1 to 5 parts by weight, more preferably from 0.2 to 3 parts by weight, per 100 parts by weight of the acrylic resin (A). When the amount of the crosslinking agent (C) per 100 parts by weight of the acrylic resin (A) is 0.01 parts by weight or more, particularly 0.1 part by weight or more, since the adhesive tends to be improved, it is preferable, and When it is 5 parts by weight or less, it is preferable that the whitening of the optical film with an adhesive in the liquid crystal display device is inconspicuous.

[Other components constituting the adhesive]

The adhesive composition for forming the adhesive layer in the present invention preferably contains a decane-based compound (D) in order to improve the adhesion between the adhesive layer and the glass substrate, in particular, before the crosslinking agent is formulated. The decane-based compound (D) is preferably contained in the acrylic resin.

The decane-based compound (D) is exemplified by vinyl trimethoxy decane, vinyl triethoxy decane, vinyl ginate (2-methoxyethoxy) decane, and N-(2-aminoethyl)- 3-aminopropylmethyldimethoxydecane, N-(2-aminoethyl)-3-aminopropyltrimethoxydecane, 3-aminopropyltriethoxydecane, 3- Glycidoxypropyltrimethoxydecane, 3-glycidoxypropylmethyldimethoxydecane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxynonane, 3-chloro Propylmethyldimethoxydecane, 3-chloropropyltrimethoxydecane, 3-methylpropenyloxypropyltrimethoxydecane, 3-mercaptopropyltrimethoxydecane, 3-glycidoxy Propyltrimethoxydecane, 3-glycidoxypropyltriethoxydecane, 3-glycidoxypropyldimethoxymethylnonane, 3-glycidoxypropylethoxylate Methyl decane, etc. Two or more kinds of decane-based compounds (D) can also be used.

The decane compound (D) may also be a polyoxyalkylene oligomer. When the polyoxyalkylene oligomer is displayed in the form of a polyhydric alcohol, for example, the following may be mentioned.

a copolymer containing a mercaptopropyl group as follows: 3-mercaptopropyltrimethoxydecane-tetramethoxydecane copolymer, 3-mercaptopropyltrimethoxydecane-tetraethoxydecane copolymer, 3-mercapto a copolymer of propyltriethoxydecane-tetramethoxydecane, a copolymer of 3-mercaptopropyltriethoxydecane-tetraethoxydecane, such as the following copolymer containing mercaptomethyl: mercaptomethyltrimethyl Oxydecane-tetramethoxydecane copolymer, mercaptomethyltrimethoxydecane-tetraethoxydecane copolymer, mercaptomethyltriethoxydecane-tetramethoxydecane copolymer, mercaptomethyltriethyl a oxydecane-tetraethoxydecane copolymer, such as the following copolymer containing methacryloxypropyl: 3-methylpropenyloxypropyltrimethoxydecane-tetramethoxydecane copolymer , 3-methacryloxypropyltrimethoxydecane-tetraethoxydecane copolymer, 3-methylpropenyloxypropyltriethoxydecane-tetramethoxydecane copolymer, 3- Methyl propylene methoxy propyl triethoxy decane-tetraethoxy decane copolymer, 3-methyl propylene methoxy propyl methyl dimethyl Benzalkane-tetramethoxydecane copolymer, 3-methacryloxypropylmethyldimethoxydecane-tetraethoxydecane copolymer, 3-methylpropenyloxypropylmethyldi Ethoxy decane-tetramethoxy decane copolymer, 3-methyl propylene methoxy propyl methyl diethoxy decane-tetraethoxy decane copolymer, such as the following propylene oxy propyl group Copolymer: 3-propenyloxypropyltrimethoxydecane-tetramethoxydecane copolymer, 3-propenyloxypropyltrimethoxydecane-tetraethoxydecane copolymer, 3-propene oxide Propyltriethoxydecane-tetramethoxydecane copolymer, 3-propenyloxypropyltriethoxydecane-tetraethoxydecane copolymer, 3-propenyloxypropylmethyldi Methoxydecane-tetramethoxydecane copolymer, 3-propenylmethoxypropylmethyldimethoxydecane-tetraethoxydecane copolymer, 3-propenyloxypropylmethyldiethoxylate a decyl-tetramethoxydecane copolymer, a 3-propylene methoxy propyl methyl diethoxy decane-tetraethoxy decane copolymer, such as the following vinyl-containing copolymer: vinyl Methoxy decane-tetramethoxy decane copolymer, vinyl trimethoxy decane-tetraethoxy decane copolymer, vinyl triethoxy decane-tetramethoxy decane copolymer, vinyl triethoxy矽-tetraethoxy decane copolymer, vinyl methyl dimethoxy decane-tetramethoxy decane copolymer, vinyl methyl dimethoxy decane - tetraethoxy decane copolymer, vinyl methyl Diethoxydecane-tetramethoxydecane copolymer, vinylmethyldiethoxydecane-tetraethoxydecane copolymer, such as the following amine group-containing copolymer, etc.: 3-aminopropyltrimethyl Oxydecane-tetramethoxydecane copolymer, 3-aminopropyltrimethoxydecane-tetraethoxydecane copolymer, 3-aminopropyltriethoxydecane-tetramethoxydecane copolymer , 3-Aminopropyltriethoxydecane-tetraethoxydecane Copolymer, 3-Aminopropylmethyldimethoxydecane-tetramethoxydecane Copolymer, 3-Aminopropyl A Copolydimethoxydecane-tetraethoxydecane copolymer, 3-aminopropylmethyldiethoxydecane-tetramethoxydecane copolymer, 3-aminopropylmethyl Ethoxy Silane - tetraethyl orthosilicate copolymer.

These decane-based compounds (D) are in many cases liquid. The compounding amount of the decane-based compound in the adhesive is usually 0.01 to 10 parts by weight, preferably 0.03%, based on 100 parts by weight of the non-volatile matter of the acrylic resin (A) (the total amount is used when two or more types are used). The ratio of 1 part by weight. The amount of the decane-based compound per 100 parts by weight of the nonvolatile portion of the acrylic resin is preferably 0.01 parts by weight or more, and particularly preferably 0.03 parts by weight or more, since the adhesion between the pressure-sensitive adhesive layer and the glass substrate can be improved. Moreover, when the amount is 10 parts by weight or less, particularly preferably 1 part by weight or less, it is preferred because the tendency of the decane-based compound to bleed out from the adhesive layer is suppressed.

The adhesive layer described above may further be formulated with a crosslinking catalyst, a weathering stability, a tackifier, a plasticizer, a softener, a dye, a pigment, an inorganic filler, a resin other than the acrylic resin (A), and the like. . Further, it is also useful to prepare an ultraviolet curable compound in an adhesive, and to form an adhesive layer by irradiating ultraviolet rays to form an adhesive layer. Wherein, if the crosslinking agent and the crosslinking catalyst are simultaneously formulated in the adhesive, the adhesive layer can be prepared by a short time of aging, and the occurrence of the occurrence between the resin film and the adhesive layer in the resin film of the obtained adhesive can be suppressed. The floating or peeling causes foaming in the adhesive layer, and the reworkability is also better. As the crosslinking catalyst, for example, such as hexamethylenediamine, ethylenediamine, polyethylenimine, hexamethylenetetramine, diethylidenetriamine, triethylidenetetramine, and the like can be exemplified. A sulfone diamine, a trimethylene diamine, a polyamine resin, an amine compound of a melamine resin, or the like. When an amine compound is formulated as a crosslinking catalyst in the adhesive, the crosslinking agent is preferably an isocyanate compound.

Each of the components constituting the adhesive is an adhesive composition dissolved in a solvent, applied to a suitable substrate, and dried to form an adhesive layer.

[Gel fraction of adhesive layer]

The present invention is as described above, and the adhesive layer has a gel fraction of 70 to 99% by weight. The gel fraction is based on the values measured in the following (I) to (IV).

(I) An adhesive layer having an area of about 8 cm × about 8 cm is adhered to a metal mesh (having a weight of Wm) composed of SUS304 of about 10 cm × about 10 cm.

(II) Weighing the weight of the adhesive obtained in the above (I), the weight of which is set to Ws, and then folded into a four-fold by wrapping the adhesive layer to be weighed by a stapler, and the weight is set. Wb.

(III) A mesh placed in the above-mentioned (II) by the stapler was placed in a glass container, and after impregnation with 60 ml of ethyl acetate, the glass container was stored at room temperature for 3 days.

(IV) The mesh was taken out from the glass container, dried at 120 ° C for 24 hours, weighed and its weight was set to Wa, and the gel fraction was calculated according to the following formula:

Gel fraction (% by weight) = [{Wa - (Wb - Ws) - Wm} / (Ws - Wm)] × 100

The gel fraction of the adhesive is set to 70 to 99% by weight. When the gel fraction is 70% by weight or more, it is preferable to improve the durability of the adhesive, and when the gel fraction is 99% by weight or less, it is preferable because it is easy to manufacture.

The gel fraction of the adhesive can be adjusted by the kind of the acrylic resin (A) or the amount of the crosslinking agent of the active ingredient of the adhesive. Specifically, when the amount of the unsaturated monomer (A-3) having a polar functional group in the acrylic resin (A) is large, or the amount of the crosslinking agent (C) in the adhesive composition is large Further, since the gel fraction is high, the gel fraction can be adjusted by the amount of the unsaturated monomer having a polar functional group and/or the crosslinking agent. Therefore, regarding the unsaturated monomer (A-3) having a polar functional group, the unit amount of the unsaturated monomer (A-3) having the polar functional group in the acrylic resin (A) is 0.1 to 5 The combination of the weight % and the combination of the other components constituting the acrylic resin (A) and the type and amount of the crosslinking agent may be selected and adjusted to have the gel fraction within the above range. Further, the amount of the crosslinking agent (C) is preferably a ratio of the crosslinking agent to 100 parts by weight of the non-volatile content of the acrylic resin (A) constituting the adhesive (the total amount of the two types or more is used) It is selected from the range of 0.1 to 5 parts by weight in combination with the type of acrylic resin.

[Optical film with adhesive]

The optical film with an adhesive of the present invention is one in which an adhesive layer formed of the above adhesive composition is provided on at least one side of the optical film. The optical film used herein is a film having optical characteristics, and examples thereof include, for example, a polarizing plate, a retardation film, and the like.

The so-called polarizing plate is an optical film having a function of emitting polarized light for incident light such as natural light. The polarizing plate has a linear polarizing plate having a property of absorbing a linear polarized light having a vibrating surface in a certain direction and transmitting a linear polarized light having a vibrating surface perpendicular thereto; and having a linear polarized reflection of a vibrating surface having a certain direction, and A polarized light separation film having a property of transmitting a linearly polarized light having a vibration plane perpendicular thereto; and an elliptical polarizing plate obtained by laminating a polarizing plate and a retardation film to be described later. The most preferable examples of the polarizing plate, especially the linear polarizing film (also referred to as a polarizing photon, a polarizing film), are exemplified by adsorbing iodine or a dichroic dye on a uniaxially stretched polyvinyl alcohol resin film. Chromatic pigments and aligners.

The retardation film is an optical film exhibiting optical anisotropy, and is exemplified by, for example, polyvinyl alcohol, polycarbonate, polyester, polyarylate, polyimide, polyolefin, cyclic polyolefin, poly High in composition of styrene, polyfluorene, polyether oxime, polyvinylidene fluoride/polymethyl methacrylate, liquid crystal polyester, acetyl cellulose, ethylene-vinyl acetate copolymer saponified product, polyvinyl chloride, etc. The molecular film is extended to an extended film obtained by about 1.01 to 6 times. Among them, a polymer film in which a polycarbonate film or a cyclic polyolefin film is uniaxially stretched or biaxially stretched is preferred. The uniaxial retardation film is also referred to as a wide viewing angle retardation film or a low photoelasticity retardation film, and any of them can be used.

Further, a film exhibiting optical anisotropy by coating of a liquid crystal compound or a film exhibiting optical anisotropy by coating with an inorganic layer compound may be used as the retardation film. The retardation film is a film called a temperature-compensated retardation film, and a film which is sold by Nippon Oil Co., Ltd. under the trade name "LC Film" to make a rod-like liquid crystal spiral alignment, the same by New Japan. A film that is sold under the trade name of "NH Film", which is a tilt-aligned film of a rod-shaped liquid crystal, which is sold by Fuji Film Co., Ltd. under the trade name "WV Film", which is a film in which the disc-shaped liquid crystal is obliquely aligned. A fully biaxially oriented film sold by Sumitomo Chemical Co., Ltd. under the trade name "VAC Film", the same biaxially oriented film sold by Sumitomo Chemical Co., Ltd. under the trade name "new VAC Film". .

Further, an optical film may be used in which a protective film is adhered to the optical films. As the protective film, a transparent resin film is used, and the transparent resin is exemplified by, for example, an ethylene glycol-based resin typified by triethyl fluorenyl cellulose or diethyl fluorenyl cellulose, and represented by polymethyl methacrylate. A methacrylic resin, a polyester resin, a polyolefin resin, a polycarbonate resin, a polyether ether ketone resin, a polyfluorene resin, or the like. The resin constituting the protective film may be formulated with a UV absorption such as a salicylate-based compound, a benzophenone-based compound, a benzotriazole-based compound, a triazine-based compound, a cyanoacrylate-based compound, or a nickel-salted salt-based compound. Agent. As the protective film, an ethylene glycol-based resin film such as a triethylenesulfonated cellulose film is preferably used.

In the optical film described above, the linear polarizing plate is often used in a state in which a protective film is adhered to one surface or both surfaces of a polarizing film composed of a polyvinyl alcohol resin. Further, the elliptically polarizing plate is formed by laminating a linear polarizing plate and a retardation film, and the polarizing plate is often in a state in which a protective film is adhered to one surface or both surfaces of the polarizing film. When the adhesive layer of the present invention is formed on the elliptically polarizing plates, an adhesive layer is usually formed on the side of the retardation film.

Preferably, the optical film with an adhesive adheres to the release film on the surface of the adhesive layer until the surface of the adhesive layer is protected before use. The optical film provided with the adhesive of the release film can be produced by, for example, coating the above-mentioned adhesive composition on a release film and forming an adhesive layer, and then laminating the optical film on the obtained adhesive layer. The method comprises the steps of: applying an adhesive composition on an optical film and forming an adhesive layer, and adhering a release film on the adhesive surface to protect the optical film with an adhesive layer. The release film used herein may be a film made of various resins such as polyethylene terephthalate, polybutylene terephthalate, polycarbonate, polyarylate, or the like, and The surface on which the substrate and the adhesive layer are bonded is subjected to a release treatment such as an anthrone treatment.

The thickness of the adhesive layer is not particularly limited, but is usually preferably 30 μm or less, more preferably 10 μm or more, and still more preferably 15 to 25 μm. When the thickness of the adhesive layer is 30 μm or less, the adhesion under high temperature and high humidity is improved, and the possibility of occurrence of floating or peeling between the glass substrate and the adhesive layer is lowered, and reworkability is obtained. It is preferable to obtain a tendency to increase, and when the thickness is 10 μm or more, even if the size of the optical film adhered thereon changes, since the adhesive layer changes with the change in size thereof, the brightness of the peripheral portion of the liquid crystal cell There is no difference between the brightness of the center portion and the tendency to suppress whitening or color unevenness. The thickness of the adhesive layer which is generally adhered to the liquid crystal cell glass has been 25 μm. However, in the present invention, even if the thickness is 20 μm or less, the performance as an adhesive layer can be sufficiently exhibited.

When the optical film with the adhesive layer of the present invention is adhered to the glass substrate to form an optical laminate, when the optical film is peeled off from the glass substrate due to mismatch, the adhesive layer is in contact with the adhesive layer due to peeling of the optical film. The surface of the peeled substrate hardly causes blurring or paste-like residue, so that the peeled glass substrate can be easily and directly adhered to the optical film with the adhesive. In other words, the so-called reworkability is excellent.

[optical laminate]

The optical film with an adhesive of the present invention can be laminated on a glass substrate with an adhesive layer to form an optical laminate. An optical laminate obtained by laminating an optical film with an adhesive on a glass substrate, for example, an optical film peeling release film obtained by adhering the above-mentioned adhesive, and adhering the exposed adhesive layer to the surface of the glass substrate can. Here, the glass substrate can be, for example, a glass substrate of a liquid crystal cell, an antiglare glass, or a glass for sunglasses. Wherein, an optical film (upper polarizing plate) with an adhesive is laminated on the glass substrate on the front side (identification side) of the liquid crystal cell, and another optical film with an adhesive is laminated on the glass substrate on the back side of the liquid crystal cell ( The optical laminate formed of the lower polarizing plate is preferable because it can be used as a panel (liquid crystal panel) of a liquid crystal display device. As the material of the glass substrate, for example, soda glass, low alkali glass, alkali-free glass, or the like is exemplified.

Regarding the optical laminate of the present invention, an example of a relatively suitable layer configuration is shown in a sectional view in Fig. 1. In the example shown in Fig. 1(A), the protective film 3 having the surface treated layer 2 is adhered to one surface of the linear polarizing film 1 on the side opposite to the surface treated layer 2, thereby constituting the polarizing plate 5. In this example, the polarizing plate 5 can also be the optical film 10 of the present invention at the same time. The adhesive layer 20 containing an ionic compound described above is provided on the surface of the linear polarizing film 1 opposite to the protective film 3 to constitute an optical film 25 with an adhesive. Next, the surface of the adhesive layer 20 opposite to the polarizing plate 5 is adhered to the liquid crystal cells 30 of the glass substrate to form the optical laminate 40.

An example shown in FIG. 1(B) is that the first protective film 3 having the surface treatment layer 2 is adhered to one side of the linear polarizing film 1 on the side opposite to the surface treatment layer 2, and is linearly polarized. The second protective film 4 is adhered to the other surface of the film 1 to constitute the polarizing plate 5. In this example, the polarizing plate 5 also serves as the optical film 10 of the present invention. An adhesive layer 20 containing an ionic compound described above is provided on the outer side of the second protective film 4 constituting the polarizing plate 5 to constitute an optical film 25 with an adhesive. Next, the surface of the adhesive layer 20 opposite to the polarizing plate 5 is adhered to the liquid crystal cells 30 of the glass substrate to form the optical laminate 40.

In the example shown in Fig. 1(C), the protective film 3 having the surface treated layer 2 is adhered to one surface of the linear polarizing film 1 on the side opposite to the surface treated layer 2 to constitute a polarizing plate 5. The surface of the linear polarizing film 1 opposite to the protective film 3 is adhered to the retardation film 7 through the interlayer adhesive 8 to form the optical film 10. The adhesive layer 20 containing an ionic compound described above is provided on the outer side of the retardation film 7 constituting the optical film 10 to constitute an optical film 25 with an adhesive. Next, the surface of the adhesive layer 20 on the opposite side to the polarizing plate 10 is adhered to the liquid crystal cell 30 of the glass substrate to form the optical laminate 40.

Further, in the example shown in FIG. 1(D), the first protective film 3 having the surface treatment layer 2 is adhered to the single surface of the linear polarizing film 1 on the side opposite to the surface treatment layer 2, and is in a straight line. The second protective film 4 is adhered to the other surface of the polarizing film 1 to constitute the polarizing plate 5. The outer surface of the second protective film 4 constituting the polarizing plate 5 is adhered to the retardation film 7 through the interlayer adhesive 8, and the optical film 10 is formed. The adhesive layer 20 containing an ionic compound described above is provided on the outer side of the retardation film 7 constituting the optical film 10 to constitute an optical film 25 with an adhesive. Next, the surface of the adhesive layer 20 on the opposite side to the optical film 10 is adhered to the liquid crystal cells 30 of the glass substrate to form the optical laminate 40.

In these examples, the first protective film 3 and the second protective film 4 are usually made of a triethylenesulfonated cellulose film, but they may be formed of various transparent resin films as described above. Further, the surface treatment layer formed on the surface of the first protective film 3 may be a hard coat layer, an antiglare layer, an antireflection layer, an antistatic layer or the like. A plurality of layers such as these may also be provided.

As shown in Figs. 1(C) and (D), when the retardation film 7 is laminated on the polarizing plate 5, if it is a small-sized liquid crystal display device, a preferred example of the retardation film 7 can be exemplified as 1/ 4 wavelength plate. In this case, the absorption axis of the polarizing plate 5 and the retardation axis of the retardation film 7 of the quarter-wavelength plate are generally arranged at an intersection of about 45 degrees, but depending on the characteristics of the liquid crystal cells 30, the angle may be from 45 degrees. Offset to some extent. On the other hand, in the case of a large-sized liquid crystal display device such as a television, for the purpose of phase difference compensation or viewing angle compensation of the liquid crystal cell 30, a phase difference film having various phase difference values in accordance with the characteristics of the liquid crystal cells 30 is used. In this case, the absorption axis of the polarizing plate 5 and the slow axis of the retardation film 7 are usually arranged in a substantially vertical or substantially parallel relationship. When the retardation film 7 is formed of a quarter-wave plate, a uniaxial or biaxially stretched film is preferably used. Further, when the retardation film 7 is provided for the purpose of phase difference compensation or viewing angle compensation of the liquid crystal cells 30, in addition to the uniaxial or biaxially stretched film, it is also possible to use the uniaxial or biaxial stretching in the thickness direction. As the retardation film 7, a film called an optical compensation film, such as a film which exhibits a phase difference and a film which is fixed by alignment, is applied to a support film.

Similarly, as shown in Figs. 1(C) and (D), when the interlayer adhesive 8 is adhered to the polarizing plate 5 and the retardation film 7, the interlayer adhesive 8 can be formulated with an ionic compound as described above. An electrostatic agent imparts an antistatic property. However, since the antistatic property is not desired in this portion, a general acrylic adhesive containing no antistatic agent is usually used. Further, as in the large-sized liquid crystal display device described above, when the absorption axis of the polarizing plate 5 is substantially perpendicular or substantially parallel to the slow axis of the retardation film 7, the polarizing plate 5 and the retardation film 7 can be passed through the roller. In the case where the roll is pasted and the peeling property is not required between them, an adhesive which can be strongly bonded once adhered and which does not peel off can be used instead of the interlayer adhesive 8 shown in Figs. 1(C) and (D). The above-mentioned adhesives are exemplified by, for example, an aqueous solution or an aqueous dispersion, an aqueous adhesive which exhibits an adhesive force by evaporating water as a solvent, and an ultraviolet curable adhesive which exhibits an adhesive force by ultraviolet irradiation.

Further, the adhesive layer 20 containing the ionic compound formed on the retardation film 7 shown in Figs. 1(C) and (D) can also be circulated by itself, and becomes the optical of the adhesive of the present invention. film. An optical film having an adhesive layer formed by forming an adhesive layer containing an ionic compound on a retardation film can be used as an optical laminate for adhering the adhesive layer to a liquid crystal cell of a glass substrate, and the phase difference can also be obtained. The film side is pasted with a polarizing plate to become another optical film with an adhesive.

1 is a view showing an example in which an optical film 25 with an adhesive is disposed on the side of the liquid crystal cell 30. However, the optical film with an adhesive of the present invention may be disposed on the back side of the liquid crystal cell, that is, on the side of the backlight. When the optical film with an adhesive of the present invention is disposed on the back side of the liquid crystal cell, the protective film 3 having the surface treatment layer 2 shown in FIG. 1 may be replaced with a protective film having no surface treatment layer, and the other may be as shown in FIG. (A)~(D). In this case, a film for improving brightness, a light-concentrating film, a diffusion film, or the like may be provided on the outer side of the protective film constituting the polarizing plate, and various optical films which are known to be disposed on the back side of the liquid crystal cell may be provided.

As described above, the optical laminate of the present invention can be preferably used in a liquid crystal display device. The liquid crystal display device formed of the optical laminate of the present invention can be used for, for example, a liquid crystal display for personal computers including a notebook type, a desktop type, a PDA (personal digital assistant), a television, a vehicle display, an electronic dictionary, a digital camera, Digital cameras, electronic desktop computers, clocks, etc.

Example

The invention is more specifically illustrated by the following examples, but the invention is not limited thereto. In the example, the "parts" and "%" indicating the amount of use and the content are based on weight unless otherwise specified.

In the following examples, the nonvolatile matter is a value measured in accordance with the method of JIS K 5407. Specifically, the adhesive solution was taken on a shallow bottom plate at an arbitrary weight, and the ratio of the residual non-volatile weight after drying at 115 ° C for 2 hours in an explosion-proof oven was compared with the ratio of the initially measured solution weight. Further, the measurement of the weight average molecular weight is carried out in a GPC apparatus, and four "TSK gel XL" manufactured by TOSOH Co., Ltd. and "GPC KF-802" manufactured by Shodex (stock) are connected in series as a column. Tetrahydrofuran was used as the elution solution, and the sample concentration was 5 mg/ml, the sample introduction amount was 100 μl, the temperature was 40 ° C, and the flow rate was 1 ml/min, which was carried out by standard polystyrene conversion.

First, the acrylic resin (A) specified in the present invention, which is a main component of the adhesive composition, and the like, are examples of the production of an acrylic resin other than those specified in the present invention.

[Polymer Example 1]

81.8 parts of ethyl acetate, 93.6 parts of butyl acrylate (A-1), and 5.0 parts of acrylic acid (A-2) were fed into a reaction vessel equipped with a cooling tube, a nitrogen gas introduction tube, a thermometer, and a stirrer. a mixed solution of phenoxyethyl ester, 1.0 part of 2-hydroxyethyl acrylate (A-3), and 0.4 part of acrylic acid, and the internal air temperature is raised to the point where the air in the apparatus is replaced with nitrogen to be oxygen-free. 55 ° C. Subsequently, a solution of 0.14 parts of azoisobutyronitrile (polymerization initiator) dissolved in 10 parts of ethyl acetate was added in a total amount. After adding a polymerization initiator for 1 hour, the monomer was removed so that the concentration of the acrylic resin was 35%, and ethyl acetate was continuously added to the reaction vessel at an addition rate of 17.3 parts/hr, while the internal temperature was 54 to 56. The mixture was kept at ° C for 12 hours, and finally ethyl acetate was added to adjust the concentration of the acrylic resin to 20%. The weight average molecular weight Mw of the obtained acrylic resin converted into polystyrene by GPC was 1,710,000, and Mw/Mn was 4.3. This is called acrylic resin A. The structural unit of 2-hydroxyethyl acrylate derived from a hydroxyl group-containing unsaturated monomer in the acrylic resin A was 1%, and the structural unit derived from acrylic acid which is a carboxyl group-containing unsaturated monomer was 0.4%.

[Polymer Example 2]

In the monomer composition, except that the amount of butyl acrylate was changed to 90.6 parts, and the amount of 2-phenoxyethyl acrylate was changed to 8.0 parts, the ethyl acetate solution of the acrylic resin was obtained as in Polymerization Example 1. The weight average molecular weight Mw of the obtained acrylic resin converted into polystyrene by GPC was 1,740,000, and Mw/Mn was 4.1. This is called acrylic resin B. The structural unit of 2-hydroxyethyl acrylate derived from a hydroxyl group-containing unsaturated monomer in the acrylic resin B was 1%, and the structural unit derived from acrylic acid which is a carboxyl group-containing unsaturated monomer was 0.4%.

[Polymer Example 3]

In the monomer composition, except that the amount of butyl acrylate was changed to 88.6 parts, and the amount of 2-phenoxyethyl acrylate was changed to 10.0 parts, the ethyl acetate solution of the acrylic resin was obtained as in Polymerization Example 1. The weight average molecular weight Mw of the obtained acrylic resin converted into polystyrene by GPC was 1,560,000, and Mw/Mn was 4.5. This is called acrylic resin C. The structural unit of 2-hydroxyethyl acrylate derived from a hydroxyl group-containing unsaturated monomer in the acrylic resin C was 1%, and the structural unit derived from acrylic acid which is a carboxyl group-containing unsaturated monomer was 0.4%.

[Polymer Example 4: Comparison]

In the monomer composition, except that the amount of butyl acrylate was changed to 78.6 parts, and the amount of 2-phenoxyethyl acrylate was changed to 20.0 parts, the ethyl acetate solution of the acrylic resin was obtained as in the polymerization example 1. The weight average molecular weight Mw of the obtained acrylic resin converted into polystyrene by GPC was 1,370,000, and Mw/Mn was 4.4. This is called acrylic resin D. The structural unit of 2-hydroxyethyl acrylate derived from a hydroxyl group-containing unsaturated monomer in the acrylic resin D was 1%, and the structural unit derived from acrylic acid which is a carboxyl group-containing unsaturated monomer was 0.4%.

[Polymer Example 5: Comparison]

In the monomer composition, except that the amount of butyl acrylate was changed to 58.6 parts, and the amount of 2-phenoxyethyl acrylate was changed to 40.0 parts, the ethyl acetate solution of the acrylic resin was obtained as in Polymerization Example 1. The weight average molecular weight Mw of the obtained acrylic resin converted into polystyrene by GPC was 1,270,000, and Mw/Mn was 4.4. This is called acrylic resin E. The structural unit of 2-hydroxyethyl acrylate derived from a hydroxyl group-containing unsaturated monomer in the acrylic resin E was 1%, and the structural unit derived from acrylic acid which is a carboxyl group-containing unsaturated monomer was 0.4%.

[Polymer Example 6: Comparison]

In the monomer composition, except that the amount of butyl acrylate was changed to 38.6 parts, and the amount of 2-phenoxyethyl acrylate was changed to 60.0 parts, the ethyl acetate solution of the acrylic resin was obtained as in Polymerization Example 1. The weight average molecular weight Mw of the obtained acrylic resin converted into polystyrene by GPC was 1,270,000, and Mw/Mn was 5.0. This is called acrylic resin F. The structural unit of 2-hydroxyethyl acrylate derived from a hydroxyl group-containing unsaturated monomer in the acrylic resin F was 1%, and the structural unit derived from acrylic acid which is a carboxyl group-containing unsaturated monomer was 0.4%.

[Polymer Example 7: Comparison]

In the monomer composition, except that the amount of butyl acrylate was set to 98.6 parts, and 2-phenoxyethyl acrylate was not used, as in Polymerization Example 1, an ethyl acetate solution of an acrylic resin was obtained. The weight average molecular weight Mw of the obtained acrylic resin converted into polystyrene by GPC was 1,470,000, and Mw/Mn was 4.4. This is referred to as acrylic resin G. The structural unit of 2-hydroxyethyl acrylate derived from a hydroxyl group-containing unsaturated monomer in the acrylic resin G was 1%, and the structural unit derived from acrylic acid which is a carboxyl group-containing unsaturated monomer was 0.4%.

[Polymer Example 8]

In the monomer composition, the amount of the butyl acrylate was changed to 88.4 parts, the amount of the 2-phenoxyethyl acrylate was changed to 10.0 parts, and the amount of the acrylic acid was changed to 0.6 parts, and the acrylic resin was obtained as in the polymerization example 1. Ethyl acetate solution. The weight average molecular weight Mw of the obtained acrylic resin converted into polystyrene by GPC was 1,530,000, and Mw/Mn was 4.8. This is called acrylic resin H. The structural unit of 2-hydroxyethyl acrylate derived from a hydroxyl group-containing unsaturated monomer in the acrylic resin H was 1%, and the structural unit derived from acrylic acid which is a carboxyl group-containing unsaturated monomer was 0.6%.

[Polymer Example 9]

The monomer composition was changed to 78.4 parts of butyl acrylate as (A-1), 10.0 parts of 2-methoxyethyl acrylate, and 10.0 parts of 2-phenoxyethyl acrylate as (A-2). An ethyl acetate solution of an acrylic resin was obtained as in Polymerization Example 1 except that 1.0 part of 2-hydroxyethyl acrylate (0.6) of (A-3) and 0.6 part of acrylic acid were used. The weight average molecular weight Mw of the obtained acrylic resin converted into polystyrene by GPC was 1,540,000, and Mw/Mn was 4.9. This is called acrylic resin I. The structural unit of 2-hydroxyethyl acrylate derived from a hydroxyl group-containing unsaturated monomer in the acrylic resin I was 1%, and the structural unit derived from acrylic acid which is a carboxyl group-containing unsaturated monomer was 0.6%.

[Polymer Example 10: Comparison]

Into the same reaction vessel as used in Polymerization Example 1, 81.8 parts of ethyl acetate, 90.6 parts of butyl acrylate (A-1), and 8.0 parts of 2-phenoxyethyl acrylate (A-2) were fed. The ester and 1.0 part of a mixed solution of 2-hydroxyethyl acrylate (A-3) and 0.4 part of acrylic acid were used, and the internal air temperature was raised to 55 ° C while replacing the air in the apparatus with nitrogen. Subsequently, a solution of 0.14 parts of azoisobutyronitrile (polymerization initiator) dissolved in 10 parts of ethyl acetate was added in a total amount. After adding a polymerization initiator for 1 hour, the monomer was removed so that the concentration of the acrylic resin was 35%, and ethyl acetate was continuously added to the reaction vessel at an addition rate of 17.3 parts/hr, while the internal temperature was 54 to 56 °C. Hold for 4 hours. Subsequently, a solution obtained by dissolving 0.2 part of azoisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added in total, and the mixture was kept at the same temperature for 8 hours. Finally, ethyl acetate was added to adjust the concentration of the acrylic resin to 20%. The weight average molecular weight Mw of the obtained acrylic resin converted into polystyrene by GPC was 1,070,000, and Mw/Mn was 8.2. This is called acrylic resin J. The structural unit of 2-hydroxyethyl acrylate derived from a hydroxyl group-containing unsaturated monomer in the acrylic resin J was 1%, and the structural unit derived from acrylic acid which is a carboxyl group-containing unsaturated monomer was 0.4%.

Table 1 shows an overview of the monomer composition, weight average molecular weight, and Mw/Mn of Polymerization Examples 1 to 10. In the table, BA means butyl acrylate, MEA means 2-methoxyethyl acrylate, PEA means 2-phenoxyethyl acrylate, HEA means 2-hydroxyethyl acrylate, and AA means acrylic acid.

Next, the adhesive was prepared using the acrylic resin produced above, and the examples and comparative examples applied to the optical film were shown. In the following examples and comparative examples, the following examples were used as the ionic compound.

Ionic compound 1: N-octyl-4-methylpyridinium hexafluorophosphate (having the structure of the following formula, melting point 44 ° C)

[Chemical 3]

Ionic compound 2: N-hexyl-4-methylpyridinium bis(trifluoromethanesulfonyl) quinone imine (having the structure of the following formula, melting point 18 ° C)

[Chemical 4]

Ionic compound 3: trioctylmethylammonium bis(trifluoromethanesulfonyl) quinone imine (having the structure of the following formula, liquid at normal temperature)

[Chemical 5]

Ionic compound 4: tributylmethylammonium bis(trifluoromethanesulfonyl) quinone imine (having the structure of the following formula, melting point 28 ° C)

[Chemical 6]

Further, the cross-linking agent and the decane-based compound were each shown below (all trade names).

(crosslinking agent)

CORONET L: an ethyl acetate solution of a trimethylolpropane adduct of toluene diisocyanate (solid concentration: 75%), available from Japan Polyurethane (strand).

(decane compound)

KBM-403: glycidoxypropyl trimethoxy decane (liquid), purchased more confident chemical industry (shares).

[Examples 1 to 8 and Comparative Examples 1 to 6] (a) Manufacture of adhesives

The individual components of the ionic compound shown in Table 2, 0.5 parts of the decane-based compound (KBM-403), and Table 2 were mixed with respect to 100 parts of the solid components of the acrylic resins A to J obtained in Polymerization Examples 1 to 10. The individual amount of the cross-linking agent (CORONET L) shown was followed by the addition of ethyl acetate to adjust the solid content to 13% to form an adhesive composition. The crosslinking agent (CORONET L) was an ethyl acetate solution having a solid concentration of 75% as described above, but the addition amount shown in Table 2 was a solid content.

(b) Preparation of optical film with adhesive

Each of the above adhesive compositions was applied to a release-treated polyethylene terephthalate film (trade name "PET 3811", available from LINTEC, using an applicator so that the thickness after drying became 20 μm. The release surface of the film (manufactured by the separator) was dried at 90 ° C for 1 minute to obtain a sheet-like adhesive. Next, the both sides of the polarizing plate of the three-layer structure formed by sandwiching the protective film composed of triethyl fluorenyl cellulose on both sides of the polyvinyl alcohol-adsorbed iodine-adsorbed layer are laminated, and the obtained sheet is laminated. After the surface of the adhesive on the opposite side of the separator (adhesive surface), it was aged at a temperature of 23 ° C and a relative humidity of 65% for 7 days to obtain a polarizing plate with an adhesive.

(c) Evaluation of antistatic properties of optical films with adhesives

The separator of the obtained polarizing plate with an adhesive was peeled off, and the surface resistance value of the adhesive was measured by a surface inherent impedance measuring apparatus [Hirest-up MCP-HT450 (trade name) manufactured by Mitsubishi Chemical Corporation). Antistatic. If the surface resistance value is 10 ¹¹ Ω/□ or less, good antistatic properties are obtained.

(d) Fabrication and evaluation of optical laminates

After peeling off the separator from the polarizing plate with the adhesive prepared in the above (b), it is adhered to the liquid crystal cell glass substrate with the adhesive surface as a cross nicole [1737" manufactured by Corning Incorporated (trade name) On both sides, an optical laminate is produced. The optical laminate was stored under dry conditions at a temperature of 80 ° C for 96 hours for heat resistance test. Subsequently, the appearance state of whitening when light was incident from the side of the polarizing plate on one side was visually observed. The results were classified according to the following criteria and are shown in the column of "whitening (80 ° C drying)" in Table 2.

<The appearance of whitening>

1. No white at all

2. Almost invisible white

3. I saw a little white

4. Significantly confirmed white

Further, the heat resistance test (referred to as "heat resistance" in Table 2) was carried out for 300 hours under dry conditions at a temperature of 80 ° C, and the heat resistance test was carried out for 300 hours at a temperature of 60 ° C and a relative humidity of 90%. The condition referred to as "moisture-resistant heat" in Table 2, and the temperature from 70 ° C to -30 ° C, followed by the temperature rise to 70 ° C as a one-cycle (1 hour), repeated 100 cycles for thermal shock resistance In the case of the test (referred to as "HS resistance" in Table 2), the optical laminate after the test was visually observed. The results are categorized by the following criteria and are all listed in Table 2.

<Evaluation criteria against heat, damp heat and thermal shock (referred to as "heat resistance", "moisture resistance" and "HS resistance" in Table 2)

1. There is no change in appearance such as floating, peeling, foaming, etc.

2. There is almost no change in appearance such as lifting, peeling, foaming, and the like.

3. A slight change in the appearance of floating, peeling, foaming, etc. is observed.

4. Significantly confirmed changes in appearance such as floating, peeling, foaming, and the like.

(e) Reworkability evaluation of optical films with adhesives

The reworkability evaluation was carried out as follows. First, the polarizing plate with the adhesive obtained in the above (b) was cut into a test piece having a size of 25 mm × 150 mm. Next, the test piece was attached to the liquid crystal cell glass substrate with the adhesive side of the "LAMPAKER" (trade name) manufactured by FUJIPLA Co., Ltd. at 50 ° C, 5 kg / cm ² (490.3). High pressure heat treatment was carried out for 20 minutes under kPa). Then, it was heat-treated at 70 ° C for 2 hours, and then stored in an oven at 50 ° C for 48 hours, and then adhered to the test piece at a temperature of 23 ° C and a relative humidity of 50% at a speed of 300 mm/min in a 180° direction. The polarizing plate was peeled off, and the surface state of the glass plate was observed and classified according to the following criteria. The results are combined and listed in Table 2.

<Evaluation criteria for reworkability>

1. Confirm that there is no blur at all on the surface of the glass plate.

2. There is almost no blur on the surface of the glass plate.

3. Confirm the blur on the surface of the glass plate.

4. It is confirmed that the adhesive remains on the surface of the glass plate.

It can be understood from Tables 1 and 2 that Examples 1 to 8 in which a specific amount of an ionic compound and a crosslinking agent are blended in the acrylic resin specified in the present invention constitute an antistatic property, a whitening prevention property, and It is excellent in workability, and even heat resistance, moist heat resistance, and thermal shock resistance are almost satisfactory. In particular, Example 2 has excellent properties such as antistatic property, whitening prevention property, reworkability, heat resistance, moist heat resistance, and thermal shock resistance.

On the other hand, Comparative Examples 1 to 3 containing 20 parts by weight or more of an acrylic resin derived from a structural unit having an aromatic ring-containing unsaturated monomer, and a structure containing no unsaturated monomer derived from an aromatic ring were used. In Comparative Example 4 of the acrylic resin of the unit, the whitening prevention property was insufficient. Further, Comparative Example 5, which did not reach the gel fraction specified in the present invention, was found to have a change in appearance such as floating, peeling, and foaming in the heat resistance test, the damp heat resistance test, and the thermal shock resistance test. On the other hand, Comparative Example 6 using an acrylic resin having a large molecular weight distribution obtained a result of insufficient whitening prevention.

The embodiments and examples disclosed herein are illustrative only and should not be considered as limiting. The scope of the present invention is defined by the scope of the claims and the scope of the claims

[Possibility of industrial use]

The optical film with an adhesive of the present invention can impart high antistatic property while maintaining the antistatic property for a long period of time, and is excellent in durability. The optical film with an adhesive is suitable for a liquid crystal display device.

1‧‧‧Linear polarizing film

2‧‧‧Surface treatment layer

3‧‧‧First protective film

4‧‧‧Second protective film

5‧‧‧Polar plate

7‧‧‧ phase difference film

8‧‧‧Interlayer adhesive

10‧‧‧Optical film

20‧‧‧Adhesive layer containing ionic compounds

25‧‧‧Optical film with adhesive

30‧‧‧Liquid cell (glass substrate)

40‧‧‧Optical laminate

BRIEF DESCRIPTION OF THE DRAWINGS Fig. 1 is a schematic cross-sectional view showing an example of a preferred layer constitution of an optical laminate of the present invention.

1. . . Linear polarizing film

2. . . Surface treatment layer

3. . . First protective film

5. . . Polarizer

10. . . Optical film

20. . . Adhesive layer containing ionic compound

25. . . Optical film with adhesive

30. . . Liquid crystal cell (glass substrate)

40. . . Optical laminate

Claims (9)

An optical film with an adhesive, which is an optical film with an adhesive layer forming an adhesive layer on at least one side of the optical film, characterized in that the adhesive layer is formed of an adhesive composition containing the following: 100 weight The (A) weight average molecular weight Mw is 1 million to 2 million, and the molecular weight distribution Mw/Mn (weight ratio molecular weight (Mw) and number average molecular weight (Mn) ratio) is 3 to 7 acrylic resin, which is a copolymer obtained by the following monomer mixture of (A-1) to (A-3), 80 to 96% by weight of (A-1) (meth) acrylate represented by the following formula (I): (wherein R ₁ represents a hydrogen atom or a methyl group, R ₂ represents an alkyl group having 1 to 14 carbon atoms which may be substituted by an alkoxy group having 1 to 10 carbon atoms), and 3 to 15% by weight of (A-2) An unsaturated monomer having an olefinic double bond and at least one aromatic ring in the molecule, and 0.1 to 5% by weight of (A-3) an unsaturated monomer having a polar functional group; and 0.2 to 8 parts by weight of (B) An ionic compound having an organic cation and having a melting point of 80 ° C or lower and being solid at normal temperature; and 0.01 to 5 parts by weight of the (C) crosslinking agent, the adhesive layer having a gel fraction of 70 to 99% by weight. An optical film with an adhesive according to claim 1, wherein the unsaturated monomer (A-2) having an olefinic double bond and at least one aromatic ring in the molecule is an aromatic ring represented by the following formula (II) (meth)acrylic monomer: (wherein R ₃ represents a hydrogen atom or a methyl group, n is an integer of 1 to 8, and R ₄ is a hydrogen atom, an alkyl group, an aralkyl group or an aryl group). An optical film with an adhesive according to claim 1, wherein the polar functional group of the polar functional group-containing unsaturated monomer (A-3) is selected from the group consisting of a free carboxyl group, a hydroxyl group, an amine group, and an epoxy group. The group formed. An optical film with an adhesive according to claim 3, wherein the crosslinking agent (C) comprises an isocyanate compound. An optical film with an adhesive according to the first aspect of the invention, wherein the ionic compound (B) having an organic cation has a melting point of 30 ° C or higher. An optical film with an adhesive according to the first aspect of the invention, wherein the adhesive composition further contains 0.03 to 1 part by weight of the (D) decane compound. An optical film with an adhesive according to claim 1, wherein the optical film is selected from the group consisting of a polarizing plate and a retardation film. An optical film with an adhesive as disclosed in claim 1, wherein a release film is adhered to the surface of the adhesive layer. An optical laminate characterized in that the optical film with an adhesive attached to the first aspect of the patent application is laminated on the glass substrate with its adhesive layer side.