JP5615608B2 - Adhesive composition and pressure-sensitive adhesive, and pressure-sensitive adhesive for optical members, and optical member with a pressure-sensitive adhesive layer obtained using the same - Google Patents

Description

  The present invention relates to a pressure-sensitive adhesive composition and a pressure-sensitive adhesive, a pressure-sensitive adhesive for optical members, and an optical member with a pressure-sensitive adhesive layer obtained using the same. Specifically, an optical film (polarizing film, retardation film, optical compensation film, brightness enhancement film, etc.) suitably used for liquid crystal display devices, organic EL display devices, image display devices such as PDP, etc. A pressure-sensitive adhesive for an optical member used for bonding an optical laminate in which a polarizing film is coated with a protective film such as a cellulose triacetate film and a glass substrate of a liquid crystal cell, and a pressure-sensitive adhesive layer comprising the pressure-sensitive adhesive for the optical member The present invention relates to an optical member with an adhesive layer, particularly a polarizing plate with an adhesive layer.

  Conventionally, a polarizing film, for example, a polarizing plate coated with a cellulose film, for example, a cellulose triacetate film, on both sides of a polarizing film, for example, a polyvinyl alcohol film having a polarizing property, is a liquid crystal component that is aligned between two glass plates. Lamination is carried out on the surface of the sandwiched liquid crystal cell to form a liquid crystal display panel. This lamination to the liquid crystal cell surface is performed by bringing the pressure-sensitive adhesive layer provided on the polarizing plate surface into contact with the liquid crystal cell surface. This is usually done by pressing.

  The pressure-sensitive adhesive layer provided on the surface of the optical member such as the polarizing plate is provided with a separator for the purpose of preventing scratches or dirt, or the surface for the purpose of preventing scratches or dirt generated during processing and transporting processes. Although a protective film or the like is provided, these separators and the surface protective film are not necessary and are peeled and removed when they are bonded to a liquid crystal cell or the like. Static electricity is generated when the separator or the surface protection film is peeled off from such an optical member, and this static electricity causes dust to adhere to the optical member, causes an abnormal display due to disorder of the liquid crystal alignment, and peripheral circuit elements. There is a problem that problems such as electrostatic breakdown occur.

In addition, when an optical member provided with the above-mentioned pressure-sensitive adhesive layer is bonded to a liquid crystal cell, if foreign matter is mixed, damaged, or an adhesion error occurs, it will be peeled off and re-bonded. As described above, static electricity is generated and a problem occurs.
As a countermeasure for preventing the occurrence of defects due to such static electricity generation, for example, an adhesive type obtained by forming an adhesive layer having a polymer having an glass transition temperature of 0 ° C. or lower and an ionic liquid on one or both surfaces of an optical member An optical member has been proposed (see, for example, Patent Document 1).
In addition, an antistatic pressure-sensitive adhesive composition containing an acrylic polymer and a lithium imide salt having a perfluoroalkyl group as an antistatic agent is used as an antistatic surface protective film (for example, see Patent Document 2). ), An ionic liquid having a fluorine-containing imide anion, and a pressure-sensitive adhesive composition containing a polymer having a glass transition temperature Tg of 0 ° C. or less as a base polymer (see, for example, Patent Document 3).

JP 2006-11365 A JP-A-2005-306937 JP 2006-45475 A

  However, although the technique disclosed in Patent Document 1 describes that the ionic liquid is simply blended with the acrylic polymer, the type of the ionic liquid to be used has not been optimized, and antistatic Durability and light leakage prevention performance, which are important when using such pressure-sensitive adhesives in optical members, particularly polarizing plate applications, are not considered at all and are not sufficient. .

  Furthermore, in the technology disclosed in Patent Document 2 and Patent Document 3, in the pressure-sensitive adhesive composition in which a fluorine-containing lithium imide salt is blended with an acrylic polymer, an imide salt having a perfluoroalkyl group is used as the fluorine-containing imide salt. Although the effect on the antistatic performance is recognized, the durability and light leakage prevention performance, which are important when such an adhesive is used in an optical member, particularly a polarizing plate, are not considered at all. There was room for improvement. In addition, an imide salt having a perfluoroalkyl group needs to use an electrolytic fluorination method for fluorine substitution of an alkyl group in its production, and its production is very difficult and costly.

  By the way, liquid crystal display panels using polarizing plates are widely used as display devices for personal computers, liquid crystal televisions, car navigation systems, etc., and the use environment has become very harsh. It is required to be excellent in durability even in use, for example, there is no phenomenon such as foaming or peeling between the pressure-sensitive adhesive layer and the glass plate even under a severe environment such as high temperature and high humidity, In a high-temperature, high-humidity environment, the polarizing film contracts, whereas the adhesive layer cannot follow the contraction of the polarizing film, and light leaks from the peripheral edge of the liquid crystal display panel. It is required that there is no so-called light leakage phenomenon.

  Therefore, in the present invention, under such a background, the antistatic performance is excellent, and further, even under high temperature and high humidity conditions, the optical laminate, particularly, the adhesive property between the polarizing plate and the glass substrate is excellent, and the pressure-sensitive adhesive. A pressure-sensitive adhesive composition and a pressure-sensitive adhesive, particularly an optical member, which do not cause foaming or peeling between the layer and the glass substrate and can prevent light leakage caused by contraction of the polarizing film. It is intended to provide a pressure-sensitive adhesive composition, a pressure-sensitive adhesive for optical members, and an optical member with a pressure-sensitive adhesive layer obtained using the same.

  However, the present inventors have conducted extensive research in view of such circumstances, and as a result, bis (fluorosulfonyl) having a structure in which a fluorine atom is bonded directly to a sulfonyl group without a carbon atom as an antistatic agent used in combination with an acrylic resin. By using an ionic compound having an imide) anion, it has been found that sufficient antistatic performance is exhibited and excellent durability when used for an optical member, and the present invention has been completed.

That is, the gist of the present invention, the acrylic resin (A), the bis ionic compound having a (fluorosulfonyl) imide anion (B), and contains an oxyalkylene structure, the following general having no hydroxyl group in the molecular chain end It is related with the adhesive composition characterized by including the oxyalkylene group containing compound (C) which is a compound shown by Formula (1) .
Further, it is represented by the following general formula (1) containing an acrylic resin (A), an ionic compound (B) having a bis (fluorosulfonyl) imide anion, an oxyalkylene structure, and no hydroxyl group at the molecular chain terminal. The pressure-sensitive adhesive composition [I] containing the oxyalkylene group-containing compound (C), which is a compound to be obtained, is crosslinked, and relates to a pressure-sensitive adhesive.
Furthermore, the present invention relates to an optical member with an adhesive layer, wherein the adhesive for an optical member using the above-mentioned adhesive and the adhesive for an optical member are laminated on the optical member.

  The pressure-sensitive adhesive of the present invention can be suitably used particularly for optical member applications, has an excellent balance between pressure-sensitive adhesive properties and antistatic performance, and is also an optical laminate, particularly polarized light, even under high temperature and high humidity conditions. Excellent adhesion between the plate and the glass substrate, no foaming or peeling between the pressure-sensitive adhesive layer and the glass substrate, and prevention of light leakage caused by contraction of the polarizing film In addition, an excellent liquid crystal display panel can be obtained.

  The pressure-sensitive adhesive of the present invention can also be used as a temporary surface-protecting pressure-sensitive adhesive; various displays such as word processors, computers, mobile phones, and televisions; optical components such as polarizing plates and laminates equivalent thereto; electronic substrates In general, a transparent surface protection sheet such as polyethylene, polyester, or polypropylene is laminated via an adhesive for the purpose of surface protection and functionalization. For example, the sheet often finishes the role of surface protection after the incorporation of a liquid crystal display or the like is completed and is peeled and removed. In this case, static electricity is generated when the surface protective adhesive sheet is peeled off, and surrounding dust is involved. In addition, there is a trouble that the liquid crystal substrate and the electronic circuit are destroyed by the peeling charge generated when the surface protective adhesive sheet is peeled off. Those having an effect like hardly occurs.

The present invention will be described in detail below, but these show examples of desirable embodiments.
In the present invention, (meth) acryl means acryl or methacryl, (meth) acryloyl means acryloyl or methacryloyl, and (meth) acrylate means acrylate or methacrylate.

First, the pressure-sensitive adhesive composition of the present invention will be described.
The pressure-sensitive adhesive composition of the present invention comprises an acrylic resin (A), an ionic compound (B) having a bis (fluorosulfonyl) imide anion, a compound containing an oxyalkylene structure and containing no hydroxyl group at the molecular chain terminal. And an oxyalkylene group-containing compound (C).

  As the acrylic resin (A), a copolymer component containing the (meth) acrylic monomer (a1) represented by the following general formula (2) is copolymerized with other copolymer components or homopolymerized. It is preferable from the viewpoint of further improving the antistatic performance.

  X in the general formula (2) is an alkylene group, among which an alkylene group having 1 to 10 carbon atoms is preferable, and in particular, an alkylene group having 1 to 4 carbon atoms such as an ethylene group, a propylene group, or a tetramethylene group. And ethylene group is particularly preferable. Further, when n is a polyoxyalkylene chain moiety having 2 or more, a homopolymer of the same oxyalkylene chain may be used, or different oxyalkylene chains may be copolymerized randomly or in a block form.

  Y in the general formula (2) is any one of a hydrogen atom, an alkyl group, an aryl group, and an aralkyl group. Among these, a hydrogen atom, an alkyl group, and an aryl group are preferable, a hydrogen atom, an alkyl group, and a phenyl group are particularly preferable, and an acrylic resin (A) is easily manufactured and an antistatic property is more preferable. From the viewpoint of improving performance, an alkyl group is preferable, and a methyl group is particularly preferable.

  The alkyl group preferably has a relatively short carbon number, specifically 1 to 15 carbon atoms, particularly preferably 1 to 10 carbon atoms, further preferably 1 to 6 carbon atoms. Y) is preferably a methyl group, an ethyl group or a propyl group, and particularly preferably a methyl group. If the number of carbon atoms is too long, the HLB is lowered and the antistatic performance tends to be lowered due to the lipophilicity.

  As the aryl group, those having 6 to 20 carbon atoms, preferably 6 to 15 carbon atoms are usually used, and specific examples include phenyl group, tolyl group, xylyl group, biphenyl group, naphthyl group and the like. Among these, a phenyl group is preferable.

  As the aralkyl group, those having 7 to 20 carbon atoms, preferably 7 to 15 carbon atoms are usually used, and specific examples include a benzyl group.

  The alkyl group, aryl group, and aralkyl group may have a substituent. The substituent is usually a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, a hydroxyl group, an alkoxy group. Group, amino group, sulfanyl group, aryl group, heteroaryl group and the like.

R ₁ in the general formula (2) is a hydrogen atom or a methyl group.

  In the general formula (2), n is an integer of 1 or more, preferably 1 to 10, particularly preferably 1 to 2, and further preferably 1. If the value of n is too large, the moisture and heat resistance of the acrylic resin tends to decrease, and n is preferably small from the viewpoint of easy production of an acrylic resin among the raw materials that can be procured.

When Y in the general formula (2) is a hydrogen atom, examples of the monomer of n = 1 include 2-hydroxyethyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 5-hydroxypentyl (meta 1) Acrylic acid hydroxyalkyl esters such as acrylate, 6-hydroxyhexyl (meth) acrylate, 8-hydroxyoctyl (meth) acrylate, 10-hydroxydecyl (meth) acrylate, and (4-hydroxymethylcyclohexyl) methyl acrylate Secondary hydroxyl group-containing monomer; secondary hydroxyl group-containing monomer such as 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate; 2,2-dimethyl-2 -Hydroxyethyl (Meth) tertiary hydroxyl group-containing monomers such as acrylate.
Examples of the monomer having n of 2 or more include polyethylene glycol derivatives such as polyethylene glycol mono (meth) acrylate, polypropylene glycol derivatives such as polypropylene glycol mono (meth) acrylate, polyethylene glycol-polypropylene glycol-mono (meth) acrylate, poly (Ethylene glycol-tetramethylene glycol) mono (meth) acrylate, poly (propylene glycol-tetramethylene glycol) mono (meth) acrylate, and the like.

  When Y in the general formula (2) is an alkyl group, for example, 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, 2-butoxy Ethyl (meth) acrylate, 2-butoxydiethylene glycol (meth) acrylate, methoxydiethylene glycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, methoxydipropylene glycol (meth) acrylate, methoxypolyethylene glycol (Meth) acrylate, octoxypolyethylene glycol-polypropylene glycol-mono (meth) acrylate, lauroxypolyethylene glycol mono (meth) acrylate , Stearoxy polyethylene glycol mono (meth) acrylate aliphatic of (meth) acrylic acid ester.

  When Y in the general formula (2) is an aryl group, examples thereof include phenoxyethyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, ethylene oxide-modified nonylphenol (meth) acrylate, and the like.

  When Y in the general formula (2) is an aralkyl group, examples thereof include benzyloxyethyl (meth) acrylate and benzyloxydiethylene glycol (meth) acrylate.

  Among the (meth) acrylic monomers (a1), a hydroxyl group-containing monomer and a methoxy group-containing monomer are preferable in terms of effectively imparting hydrophilicity, particularly a primary hydroxyl group-containing monomer and a methoxy group-containing monomer, Hydroxyethyl acrylate and 2-methoxyethyl acrylate are preferred. Moreover, it is also preferable to use 2 or more types of said monomers together, and it is especially preferable to use 2 types together.

  The (meth) acrylic monomer (a1) is preferably contained in an amount of 5 to 100% by weight, particularly preferably 8 to 70% by weight, based on the entire copolymerization component, as a copolymerization component of the acrylic resin (A). More preferably, it is 10 to 50% by weight, particularly preferably 20 to 40% by weight. If the content of the (meth) acrylic monomer (a1) is too small, the antistatic performance tends to be insufficient.

  Other copolymer components other than the above (meth) acrylic monomer (a1) include (meth) acrylic acid ester monomer (a2), and if necessary, a functional group-containing monomer other than (meth) acrylic monomer (a1) And (a3) and other copolymerizable monomers (a4).

  Examples of the (meth) acrylic acid ester monomer (a2) include (meth) acrylic acid alkyl esters. About this (meth) acrylic acid alkyl ester, it is preferable that carbon number of an alkyl group is 1-12 normally, especially 1-8, Furthermore, it is preferable that it is 4-8, Specifically, methyl (meth) acrylate , Ethyl (meth) acrylate, n-butyl (meth) acrylate, iso-butyl (meth) acrylate, tert-butyl (meth) acrylate, n-propyl (meth) acrylate, n-hexyl (meth) acrylate, 2-ethylhexyl (Meth) acrylate, n-octyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, cetyl (meth) acrylate, stearyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, etc. can give. These can be used alone or in combination of two or more.

  Among such (meth) acrylic acid alkyl esters (a2), n-butyl (meth) acrylate and 2-ethylhexyl (meth) acrylate are preferable in terms of copolymerizability, adhesive physical properties, ease of handling, and availability of raw materials. N-Butyl (meth) acrylate is preferably used because it is preferably used and more preferably has excellent antistatic performance.

  Examples of the functional group-containing monomer (a3) include acrylic acid, methacrylic acid, crotonic acid, maleic acid, maleic anhydride, itaconic acid, fumaric acid, acrylamide N-glycolic acid, cinnamic acid, and (meth) acrylic acid. Michael adducts (for example, acrylic acid dimer, methacrylic acid dimer, acrylic acid trimer, methacrylic acid trimer, acrylic acid tetramer, methacrylic acid tetramer, etc.), 2- (meth) acryloyloxyethyldicarboxylic acid monoester (for example, 2- Acryloyloxyethyl succinic acid monoester, 2-methacryloyloxyethyl succinic acid monoester, 2-acryloyloxyethyl phthalic acid monoester, 2-methacryloyloxyethyl phthalic acid monoester, 2-acryloyloxyethyl hexa Carboxyl group-containing monomers such as drophthalic acid monoester and 2-methacryloyloxyethyl hexahydrophthalic acid monoester); glycidyl group-containing monomers such as glycidyl (meth) acrylate and allyl glycidyl ether; acrylamide, methacrylamide, N- (n -Butoxyalkyl) acrylamide, N- (n-butoxyalkyl) methacrylamide, N, N-dimethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, N, N-dimethylaminopropyl (meth) acrylamide, acrylamide Amide group-containing monomers such as -3-methylbutylmethylamine, dimethylaminoalkylacrylamide, dimethylaminoalkylmethacrylamide; dimethylaminoethyl (meth) acrylate, diethyl Amino group-containing monomers such as aminoethyl (meth) acrylate; nitrogen-containing monomers such as acryloylmorpholine; olefin sulfonic acids such as ethylene sulfonic acid, allyl sulfonic acid, methallyl sulfonic acid, 2-acrylamido-2-methylpropane sulfonic acid , Sulfonic acid group-containing monomers such as styrene sulfonic acid or salts thereof, and the like, and are used alone or in combination of two or more.

  Among such functional group-containing monomers (a3), carboxyl group-containing monomers, glycidyl group-containing monomers, amide group-containing monomers, and nitrogen-containing monomers are preferably used. Furthermore, the carboxyl group-containing monomers have excellent release properties and are durable. It is particularly preferably used because it contributes to the properties.

  Examples of other copolymerizable monomers (a4) include acrylonitrile, methacrylonitrile, styrene, α-methylstyrene, vinyl acetate, vinyl propionate, vinyl stearate, vinyl chloride, vinylidene chloride, alkyl vinyl ether, vinyl toluene, Examples include vinyl pyridine, vinyl pyrrolidone, itaconic acid dialkyl ester, fumaric acid dialkyl ester, allyl alcohol, acrylic chloride, methyl vinyl ketone, N-acrylamidomethyltrimethylammonium chloride, allyltrimethylammonium chloride, and dimethylallyl vinylketone.

  For the purpose of increasing the molecular weight, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate A compound having two or more ethylenically unsaturated groups such as divinylbenzene can also be used in combination.

  In the present invention, the acrylic resin (A) is produced by polymerizing the copolymer components including the monomer components (a1) to (a4). The polymerization is performed by a conventionally known method. be able to. For example, in the organic solvent, the above (meth) acrylic monomer (a1), (meth) acrylic acid ester monomer (a2), other functional group-containing monomer (a3), other copolymerizable monomer (a4), etc. The polymerization monomer and polymerization initiator (azobisisobutyronitrile, azobisisovaleronitrile, benzoyl peroxide, etc.) are mixed or dropped and polymerized at reflux or at 50 to 90 ° C. for 2 to 20 hours.

  Moreover, as a content rate of superposition | polymerization components other than (meth) acrylic-type monomer (a1), (meth) acrylic acid ester-type monomer (a2) is 0 to 95 weight%, especially 30 to 92 weight%, Furthermore, 50 It is preferable that it is -90 weight%, It is preferable that it is 60-85 weight%, and functional group containing monomers (a3) other than (meth) acrylic-type monomer (a1) are 0-40 weight%, Especially 0-30. It is preferable that the content is 0 to 20% by weight, and the other copolymerizable monomer (a4) is 0 to 50% by weight, particularly 0 to 40% by weight, and further 0 to 30% by weight. preferable.

The glass transition temperature (Tg) of the acrylic resin (A) is preferably 0 ° C. or less, particularly preferably −15 ° C. or less, and further preferably −30 ° C. or less. The lower limit of the glass transition temperature (Tg) is usually -75 ° C.
The glass transition temperature (Tg) is calculated from the following Fox equation.

  The value of the glass transition temperature (Tg) of the acrylic resin (A) can be adjusted by changing the type and blending ratio of the acrylic monomer used as the copolymerization component.

  The weight average molecular weight of the acrylic resin (A) thus obtained is usually 100,000 to 3,000,000, preferably 300,000 to 2,500,000, particularly preferably 600,000 to 2,000,000, particularly preferably 1,000,000 to 1,500,000. It is. If the weight average molecular weight is too small, sufficient cohesive force tends not to be obtained. If the weight average molecular weight is too large, a large amount of diluent solvent is required, which tends to be undesirable in terms of coating properties and cost.

  The degree of dispersion (weight average molecular weight / number average molecular weight) of the acrylic resin (A) is preferably 20 or less, particularly preferably 15 or less, more preferably 10 or less, and particularly preferably 7 or less. preferable. When the degree of dispersion is too high, the pressure-sensitive adhesive layer tends to be inferior in durability performance such as heat and moisture resistance and light leakage. The lower limit of the degree of dispersion is usually 2 from the viewpoint of production limit.

  In addition, said weight average molecular weight and number average molecular weight are based on standard polystyrene molecular weight conversion, and it is based on high performance liquid chromatography (Nippon Waters, "Waters 2695 (main body)" and "Waters 2414 (detector)"). Column: Shodex GPC KF-806L (exclusion limit molecular weight: 2 × 10 7, separation range: 100 to 2 × 10 7, theoretical plate number: 10,000 plates / piece, filler material: styrene-divinylbenzene copolymer, filler The particle size is 10 μm), and the degree of dispersion is determined from the weight average molecular weight and the number average molecular weight. The glass transition temperature is calculated from the Fox equation.

  In addition, as the acrylic resin (A), it is also preferable to use an HLB value of 6.8 or more, particularly preferably 6.8 to 10, more preferably 7.0 to 8.2, Preferably it is 7.2-8.0. If the HLB value is too small, the antistatic ability tends to be lowered. In addition, when the value of HLB is too large, there exists a tendency for the heat-and-moisture resistance of acrylic resin to fall.

Such HLB (Hydrophilie-Lipophile Balance) is an HLB value according to Davies' theory, and is a value represented by HLB = Σ (base number of hydrophilic group) + Σ (base number of lipophilic group) +7.
Examples of such hydrophilic groups, types of lipophilic groups and values of the number of hydrophilic groups and lipophilic groups include those described in the following [Table 1]. For details, refer to the document “New Edition Surfactant Handbook” ”(Nippon Yushi Co., Ltd., Engineering Books Co., Ltd.), pages 234-242 -5.1.7. It is described in.

  In the present invention, the ionic compound (B) having a bis (fluorosulfonyl) imide anion (hereinafter sometimes simply referred to as “ionic compound (B)”) is a bis (fluorosulfonyl) imide anion (described below). It is only necessary to have general formula (3)), and the cation moiety may have a known general cation.

  Examples of the cation component of the ionic compound (B) include metal cations such as alkali metals, alkaline earth metals, transition metals, rare earth metals, cations of nitrogen atom-containing heterocyclic compounds, and chain-like quaternary quaternary compounds. Ammonium cations and quaternary phosphonium cations can be mentioned. Among these, alkali metal cations, alkaline earth metal cations, cations of heterocyclic compounds containing nitrogen atoms, especially alkali metal cations and nitrogen atoms containing Heterocyclic cation cations are preferably used.

As the alkali metal cation, Li ^+, Na ^+, K ⁺ are preferred, in particular, from the viewpoint of excellent solubility in acrylic polymers, Na ^+, K ⁺ is preferred.

As such an alkaline earth metal cation, Ca ⁺ and Mg ⁺ are preferable.

As the cation of the nitrogen atom-containing heterocyclic compound, an imidazolium cation, a pyrrolidinium cation, a piperidinium cation, and a pyridinium cation are preferable, and an imidazolium cation, a pyridinium cation, and further an imidazolium cation are particularly used. Is preferable in view of good antistatic performance.
Further, as the imidazolium cation, an alkyl imidazolium cation is preferably used, and a dimethylimidazolium cation is particularly preferably used.

  Further, as the imidazolium cation, a polymerizable unsaturated group-containing imidazolium cation such as a (meth) acrylic imidazolium cation or a vinyl imidazolium cation can also be used.

As the ionic compound (B) in the present invention, either a solid or a liquid may be used at room temperature. However, when a solid one is used, a high purity ionic compound can be obtained by recrystallization. It is preferable in that it is easy to make.
Incomplete purification tends to adversely affect moisture and heat resistance due to the inclusion of undesired ions and the like, and the antistatic performance tends to be slightly inferior.
In the present invention, normal temperature means 20 ° C. ± 15 ° C. (5-35 ° C.).

Specific examples of the ionic compound (B) that is solid at room temperature include lithium bis (fluorosulfonyl) imide, sodium bis (fluorosulfonyl) imide, potassium bis (fluorosulfonyl) imide, 1,3-dimethylimidazolium bis ( Fluorosulfonyl) imide and the like. Specific examples of the ionic compound (B) that is liquid at room temperature include 1,3-diethylimidazolium bis (fluorosulfonyl) imide, 1,3-dipropylimidazolium bis (fluorosulfonyl) imide, 3-dibutylimidazolium bis (fluorosulfonyl) imide, 1,3-dipentylimidazolium bis (fluorosulfonyl) imide, 1,3-dihexylimidazolium bis (fluorosulfonyl) imide, 1,3-diheptylimidazolium bis ( Fluorosulfonyl) imide, 1,3-dioctylimidazolium bis (fluorosulfonyl) imide, 1,3-dinonylimidazolium bis (fluorosulfonyl) imide, 1,3-decylimidazolium bis (fluorosulfonyl) imide, 1- Ethyl-3-methyl Midazolium bis (fluorosulfonyl) imide, 1-methyl-3-propylimidazolium bis (fluorosulfonyl) imide, 1-butyl-3-methylimidazolium bis (fluorosulfonyl) imide, 1-pentyl-3-methylimidazolium bis ( Fluorosulfonyl) imide, 1-hexyl-3-methylimidazolium bis (fluorosulfonyl) imide, 1-heptyl-3-methylimidazolium bis (fluorosulfonyl) imide, 1-methyl-3-octylimidazolium bis (fluorosulfonyl) ) Imide, 1-methyl-3-nonylimidazolium bis (fluorosulfonyl) imide, 1-decyl-3-methylimidazolium bis (fluorosulfonyl) imide, 1-methyl-3-undecylimidazolium bis (fluoro Orosulfonyl) imide, 1-dodecyl-3-methylimidazolium bis (fluorosulfonyl) imide, 1-ethyl-3-propylimidazolium bis (fluorosulfonyl) imide, 1-butyl-3-ethylimidazolium bis (fluorosulfonyl) ) Imide, 1-ethyl-3-pentylimidazolium bis (fluorosulfonyl) imide, 1-ethyl-3-hexylimidazolium bis (fluorosulfonyl) imide, 1-ethyl-3-heptylimidazolium bis (fluorosulfonyl) imide 1-ethyl-3-octylimidazolium bis (fluorosulfonyl) imide, 1-ethyl-3-nonylimidazolium bis (fluorosulfonyl) imide, 1-decyl-3-ethylimidazolium bis (fluorosulfonyl) imide, 1-ethyl-3-undecylimidazolium bis (fluorosulfonyl) imide, 1-dodecyl-3-ethylimidazolium bis (fluorosulfonyl) imide, 1-butyl-3-propylimidazolium bis (fluorosulfonyl) imide, 1 -Pentyl-3-propylimidazolium bis (fluorosulfonyl) imide, 1-hexyl-3-propylimidazolium bis (fluorosulfonyl) imide, 1-heptyl-3-propylimidazolium bis (fluorosulfonyl) imide, 1-octyl -3-propylimidazolium bis (fluorosulfonyl) imide, 1-nonyl-3-propylimidazolium bis (fluorosulfonyl) imide, 1-decyl-3-propylimidazolium bis (fluorosulfonyl) imide, 1-pro Lu-3-undecylimidazolium bis (fluorosulfonyl) imide, 1-dodecyl-3-propylimidazolium bis (fluorosulfonyl) imide, 1-butyl-3-pentylimidazolium bis (fluorosulfonyl) imide, 1-butyl -3-hexylimidazolium bis (fluorosulfonyl) imide, 1-butyl-3-heptylimidazolium bis (fluorosulfonyl) imide, 1-butyl-3-octylimidazolium bis (fluorosulfonyl) imide, 1-butyl-3 -Nonylimidazolium bis (fluorosulfonyl) imide, 1-butyl-3-decylimidazolium bis (fluorosulfonyl) imide, 1-butyl-3-undecylimidazolium bis (fluorosulfonyl) imide, 1-butyl-3- Dodeci Imidazolium bis (fluorosulfonyl) imide, 1-hexyl-3-pentylimidazolium bis (fluorosulfonyl) imide, 1-heptyl-3-pentylimidazolium bis (fluorosulfonyl) imide, 1-octyl-3-pentylimidazolium Bis (fluorosulfonyl) imide, 1-nonyl-3-pentylimidazolium bis (fluorosulfonyl) imide, 1-decyl-3-pentylimidazolium bis (fluorosulfonyl) imide, 1-pentyl-3-undecylimidazolium bis (Fluorosulfonyl) imide, 1-dodecyl-3-pentylimidazolium bis (fluorosulfonyl) imide, 1-heptyl-3-hexylimidazolium bis (fluorosulfonyl) imide, 1-hexyl-3-octyl Midazolium bis (fluorosulfonyl) imide, 1-hexyl-3-nonylimidazolium bis (fluorosulfonyl) imide, 1-decyl-3-hexylimidazolium bis (fluorosulfonyl) imide, 1-hexyl-3-undecylimidazolium bis (Fluorosulfonyl) imide, 1-dodecyl-3-hexylimidazolium bis (fluorosulfonyl) imide, 1-heptyl-3-octylimidazolium bis (fluorosulfonyl) imide, 1-heptyl-3-nonylimidazolium bis (fluoro Sulfonyl) imide, 1-decyl-3-heptylimidazolium bis (fluorosulfonyl) imide, 1-heptyl-3-undecylimidazolium bis (fluorosulfonyl) imide, 1-dodecyl-3-heptylimide Bis (fluorosulfonyl) imide, 1-nonyl-3-octylimidazolium bis (fluorosulfonyl) imide, 1-decyl-3-octylimidazolium bis (fluorosulfonyl) imide, 1-octyl-3-undecylimidazolium bis (Fluorosulfonyl) imide, 1-dodecyl-3-octylimidazolium bis (fluorosulfonyl) imide, 1-decyl-3-nonylimidazolium bis (fluorosulfonyl) imide, 1-nonyl-3-undecylimidazolium bis ( Fluorosulfonyl) imide, 1-dodecyl-3-nonyloctylimidazolium bis (fluorosulfonyl) imide, 1-decyl-3-undecylimidazolium bis (fluorosulfonyl) imide, 1-decyl-3-dodecylimidazo Dialkylimidazolium bis (fluorosulfonyl) imide such as umbis (fluorosulfonyl) imide, 1-dodecyl-3-undecylimidazolium bis (fluorosulfonyl) imide, and 3-ethyl-1,2-dimethylimidazolium bis ( Fluorosulfonyl) imide, 1,2-dimethyl-3-propylimidazolium bis (fluorosulfonyl) imide, 1-butyl-2,3-dimethylimidazolium bis (fluorosulfonyl) imide, 1,2-dimethyl-3-hexyl Imidazolium bis (fluorosulfonyl) imide, 1,2-dimethyl-3-octylimidazolium bis (fluorosulfonyl) imide, 1-ethyl-3,4-dimethylimidazolium bis (fluorosulfonyl) imide, 1-isopropyl-2 , 3 -Trialkylimidazolium bis (nonafluorobutanesulfonyl) imide such as dimethylimidazolium bis (fluorosulfonyl) imide.
Among these, lithium bis (fluorosulfonyl) imide, sodium bis (fluorosulfonyl) imide, potassium bis (fluorosulfonyl) imide, and 1,3-dimethylimidazolium bis (fluorosulfonyl) imide have good antistatic performance. Are preferably used.
In addition, these ionic compounds (B) may be used independently and may use 2 or more types together.

  As content of an ionic compound (B), it is preferable that it is 0.01-30 weight part with respect to 100 weight part of acrylic resin (A), Especially 0.1-15 weight part is preferable, Further, 0.5 to 10 parts by weight, particularly 2 to 5 parts by weight is preferable. When the content is too large, the heat and humidity resistance tends to be lowered, and when the content is too small, the antistatic performance tends to be insufficient.

  Moreover, the adhesive composition of this invention contains an oxyalkylene group containing compound (C) at the point which improves the antistatic function and the adhesiveness with respect to an optical member.

  The content of the oxyalkylene group-containing compound (C) is usually set to 0.1 to 90 parts by weight, preferably 1 to 50 parts by weight, particularly 100 parts by weight of the acrylic resin (A). The amount is preferably 3 to 30 parts by weight, particularly 5 to 10 parts by weight. When there is too little content of the said oxyalkylene group containing compound (C), there exists a tendency for the improvement effect of antistatic ability to be hard to be acquired, and when too large, there exists a tendency for adhesive physical property to deteriorate.

The oxyalkylene group-containing compound (C) contains an oxyalkylene structure and has a hydroxyl group at the end of the molecular chain because it is not incorporated into a crosslinking system and has a high degree of freedom in the molecular chain, thereby improving the antistatic function. compounds represented by such have under following general formula (1) is used.

  X in the general formula (1) is an alkylene group, among which an alkylene group having 1 to 10 carbon atoms is preferable, and in particular, an alkylene group having 1 to 4 carbon atoms such as an ethylene group, a propylene group, or a tetramethylene group. And ethylene group is particularly preferable. Further, when n is a polyoxyalkylene chain moiety having 2 or more, a homopolymer of the same oxyalkylene chain may be used, or different oxyalkylene chains may be copolymerized randomly or in a block form.

Y ₁ and Y ₂ in the general formula (1) are any of an alkyl group, an aryl group, and an aralkyl group , and may be the same as or different from each other. Among these, an alkyl group is particularly preferable in that it contributes to the improvement of the antistatic function without inhibiting the degree of freedom of the oxyalkylene chain.

  The alkyl group preferably has a relatively short carbon number, specifically 1 to 15 carbon atoms, particularly preferably 1 to 10 carbon atoms, and further preferably 1 to 6 carbon atoms.

  As the aryl group, those having 6 to 20 carbon atoms, preferably 6 to 15 carbon atoms are usually used, and specific examples include phenyl group, tolyl group, xylyl group, biphenyl group, naphthyl group and the like. Among these, a phenyl group is preferable.

  As the aralkyl group, those having 7 to 20 carbon atoms, preferably 7 to 15 carbon atoms are usually used, and specific examples include a benzyl group.

The above alkyl group, aryl group, aralkyl group may also have a substituent, as the substituent, usually, a fluorine atom, a chlorine atom, a bromine atom, a halogen atom such as iodine atom, an alkoxy group , the aryl group, a heteroaryl group, and the like.

  In the general formula (1), n is an integer of 1 or more, preferably 1 to 10, particularly preferably 1 to 2, and further preferably 1.

Specific examples of the compound represented by the general formula (1) for the oxyalkylene group-containing compound (C) used in the present invention include polyoxyalkylene alkyl phenyl ether, polyoxyalkylene alkyl ether, polyoxyalkylene alkyl allyl ether. nonionic surfactants such as polyoxyalkylene alkyl phenyl allyl ether, and the like.

Among these, an oxyethylene group-containing compound is preferable, and examples of the oxyethylene group-containing polyether polymer include a polypropylene glycol-polyethylene glycol-polypropylene glycol block copolymer, a polypropylene glycol-polyethylene glycol block copolymer, and polyethylene glycol. -Random copolymer and block copolymer of polyethylene glycol and polypropylene glycol such as polypropylene glycol-polyethylene glycol block copolymer and polypropylene glycol-polyethylene glycol random copolymer. End of the glycol chain, A alkyl group may be substituted with a phenyl group.

The polyethylene glycol ratio in the random copolymer or block copolymer of polyethylene glycol and polypropylene glycol is preferably 5 to 75% by weight, more preferably 10 to 70% by weight. If the polyethylene glycol ratio is too small, the compatibility with the ionic liquid tends to be low, and sufficient antistatic properties tend to be difficult to obtain. If it is too high, the crystallinity becomes high and the compatibility with the acrylic polymer decreases. There is a tendency that sufficient antistatic properties cannot be obtained.
These compounds may be used alone or in combination of two or more. Among the oxyethylene group-containing compounds, polyoxyethylene alkyl ether is preferable in terms of effectively increasing the antistatic ability.

  Examples of the polyoxyethylene alkyl ether include diethylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol diethyl ether and the like having 2 repetitions, triethylene glycol diethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol diethyl ether and the like. No. 3, triethylene glycol diethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol diethyl ether, higher polyoxyethylene dimethyl ether, and the like. Among these, tetraethylene glycol dimethyl ether is preferably used.

  Moreover, in this invention, it is preferable that the oxyalkylene group content rate in the said oxyalkylene group containing compound (C) is 5-85 weight%, It is more preferable that it is 7-80 weight%, 9-75 More preferably, it is% by weight. When the content is too low, the antistatic performance tends to be inferior, and when the content is too high, the composition becomes hydrophilic and tends to be inferior in heat and moisture resistance.

  The molecular weight of the oxyalkylene group-containing compound (C) is preferably a number average molecular weight of 100 to 10000, particularly preferably 180 to 1000, and more preferably 200 to 300.

  Thus, an acrylic resin composition comprising the acrylic resin (A), the ionic compound (B) and the oxyalkylene group-containing compound (C) of the present invention is obtained.

  In the present invention, the pressure-sensitive adhesive composition [I] containing the acrylic resin (A), the ionic compound (B), and the oxyalkylene group-containing compound (C) is obtained. In addition to the components (A), (B) and (C), the pressure-sensitive adhesive composition [I] can further contain an unsaturated group-containing compound (D) and a polymerization initiator (E) described later. In order to improve the property, it is preferable to further contain a crosslinking agent (F). And this adhesive composition [I] is bridge | crosslinked and it becomes the adhesive of this invention.

Next, the pressure-sensitive adhesive of the present invention will be described.
The pressure-sensitive adhesive of the present invention is obtained by crosslinking the above-mentioned pressure-sensitive adhesive composition [I].
In the present invention, the pressure-sensitive adhesive composition [I] preferably contains the acrylic resin (A) as a main component. Here, the “main component” means that the acrylic resin ( It means that A) is usually 50% by weight or more, preferably 60% by weight or more, more preferably 70% by weight or more based on the total amount of the pressure-sensitive adhesive composition [I]. The upper limit is usually 99.9% by weight.

  As a method of crosslinking the pressure-sensitive adhesive composition [I], [α] a method of containing an unsaturated group-containing compound (D) and a polymerization initiator (E) and crosslinking with active energy rays and / or heat, [ [beta]] A method of crosslinking using a crosslinking agent (F). As for the degree of crosslinking, sufficient method can be obtained only by the method [α]. However, from the viewpoint of making the crosslinking of the pressure-sensitive adhesive more dense and improving light leakage prevention, It is particularly preferable to use the methods [β] in combination.

  First, the method [α], that is, the unsaturated group-containing compound (D) and the polymerization initiator (E) are contained, and the pressure-sensitive adhesive composition [I] is subjected to active energy rays and / or heat (active energy ray irradiation) And / or a method of crosslinking by heating) will be described.

  In the case of crosslinking by the active energy ray and / or heat (active energy ray irradiation and / or heating), as the pressure-sensitive adhesive composition [I], the above-mentioned acrylic resin (A), ionic compound (B) and In addition to the oxyalkylene group-containing compound (C), an adhesive composition [I] further containing an unsaturated group-containing compound (D) and a polymerization initiator (E) is used. Thus, by containing the unsaturated group-containing compound (D), crosslinking can be adjusted, and it becomes possible to realize adhesive properties suitable for optical member applications. Moreover, the reaction at the time of active energy ray irradiation and / or a heating can be stabilized by containing the said polymerization initiator (E).

  In the case of the cross-linking, the unsaturated group-containing compound (D) is polymerized (polymerized) by active energy rays and / or heat to cross-link (physical cross-linking) with the acrylic resin (A). When the acrylic resin (A) is an unsaturated group-containing acrylic resin, the unsaturated group-containing acrylic is not limited to polymerization of the unsaturated group-containing compound (D) by active energy rays and / or heat. Cross-linking accompanying polymerization of the resin (A) and the unsaturated group-containing compound (D) will also occur.

  The unsaturated group-containing compound (D) used in the present invention may be a monofunctional unsaturated group-containing compound having one unsaturated group in one molecule, or two or more in one molecule. A polyfunctional unsaturated group-containing compound having an unsaturated group may be used, but preferably an unsaturated group-containing compound having two or more unsaturated groups, more preferably an unsaturated group-containing compound having three or more unsaturated groups. A saturated group-containing compound is preferred from the viewpoint of curability during irradiation with active energy rays.

Examples of the structure of the unsaturated group-containing compound (D) include urethane (meth) acrylate compounds, epoxy (meth) acrylate compounds, polyester (meth) acrylate compounds, and one or more ethylene in one molecule. An ethylenically unsaturated monomer containing a polymerizable unsaturated group, for example, a monofunctional monomer, a bifunctional monomer, a trifunctional or higher functional monomer, and the like can be used. Among these, it is preferable to use the urethane (meth) acrylate compound (d1) and the ethylenically unsaturated monomer (d2) from the viewpoint of excellent curing speed and ultimate physical properties.
In addition, the unsaturated group-containing compound (D) preferably contains an oxyalkylene chain, a hydroxyl group, or an acid-base ion pair and / or a structural portion exhibiting hydrophilicity such as a betaine structure from the viewpoint of antistatic performance.

  The urethane (meth) acrylate compound (d1) is a (meth) acrylate compound having a urethane bond in the molecule, a (meth) acrylic compound containing a hydroxyl group and a polyvalent isocyanate compound (if necessary, What is necessary is just to use what is obtained by making a polyol type compound react by a well-known general method, and what is necessary is just to use the thing of 300-4000 normally as the weight average molecular weight.

  The urethane (meth) acrylate compound is not particularly limited, but a polyol compound is not included, but a polyisocyanate compound directly reacted with a (meth) acrylic compound containing a hydroxyl group is preferred.

  Examples of the (meth) acrylic compound containing a hydroxyl group include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, and 4-hydroxybutyl (meth). Acrylate, 6-hydroxyhexyl (meth) acrylate, 2- (meth) acryloyloxyethyl-2-hydroxypropyl phthalate, 2-hydroxy-3- (meth) acryloyloxypropyl (meth) acrylate, caprolactone modified 2-hydroxy Ethyl (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, caprolactone modified dipentaerythritol penta (meth) acrylate, caprolactone modified pen Examples include erythritol tri (meth) acrylate, ethylene oxide-modified dipentaerythritol penta (meth) acrylate, ethylene oxide-modified pentaerythritol tri (meth) acrylate, etc. Among them, a hydroxyl group-containing (meth) acrylic group having three or more acryloyl groups A compound is preferably used. Moreover, these can be used 1 type or in combination of 2 or more types.

  Examples of the polyvalent isocyanate compound include aromatic, aliphatic, and alicyclic polyisocyanates. Among them, tolylene diisocyanate, diphenylmethane diisocyanate, hydrogenated diphenylmethane diisocyanate, polyphenylmethane polyisocyanate, modified Diphenylmethane diisocyanate, hydrogenated xylylene diisocyanate, xylylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, tetramethylxylylene diisocyanate, isophorone diisocyanate, norbornene diisocyanate, 1,3-bis (isocyanatomethyl) cyclohexane, phenylene diisocyanate, Lysine diisocyanate, lysine triisocyanate, naphthalene diiso A polyisocyanate such as an anate or a trimer compound or a multimeric compound of these polyisocyanates, a burette type polyisocyanate, a water-dispersed polyisocyanate (for example, “Aquanate 100”, “Aquanate 110” manufactured by Nippon Polyurethane Industry Co., Ltd., "Aquanate 200", "Aquanate 210", etc.), or the reaction products of these polyisocyanates and polyols. Among these, isophorone diisocyanate, tolylene diisocyanate, hexamethylene diisocyanate, and their trimer compounds or multimeric compounds are preferably used.

  As the ethylenically unsaturated monomer (d2) used in the present invention, a monofunctional monomer, a bifunctional monomer, a trifunctional or higher monomer, and the like can be used.

  As said monofunctional monomer, what is necessary is just a monomer containing one ethylenically unsaturated group, for example, styrene, vinyl toluene, chlorostyrene, (alpha) -methylstyrene, methyl (meth) acrylate, ethyl (meth) acrylate, Acrylonitrile, vinyl acetate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, phenoxyethyl (meth) acrylate, 2-phenoxy-2-hydroxypropyl (meth) Acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, 3-chloro-2-hydroxypropyl (meth) acrylate, glycerin mono (meth) acrylate, glycidyl (meth) acrylate, lauryl (meth) acrylate Lilate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, tricyclodecanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, n-butyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate , Octyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, isodecyl (meth) acrylate, dodecyl (meth) acrylate, n-stearyl (meth) acrylate, benzyl (meth) acrylate, phenol ethylene oxide modified ( Of phthalic acid derivatives such as (meth) acrylate, nonylphenol propylene oxide modified (meth) acrylate, 2- (meth) acryloyloxy-2-hydroxypropyl phthalate Half ester (meth) acrylate, furfuryl (meth) acrylate, carbitol (meth) acrylate, benzyl (meth) acrylate, butoxyethyl (meth) acrylate, allyl (meth) acrylate, acryloylmorpholine, 2-hydroxyethylacrylamide, N -Methylol (meth) acrylamide, N-vinylpyrrolidone, 2-vinylpyridine, 2- (meth) acryloyloxyethyl acid phosphate monoester and the like.

  Examples of the ethylenically unsaturated monomer include, in addition to the above, a Michael adduct of acrylic acid or 2-acryloyloxyethyl dicarboxylic acid monoester, and examples of the Michael adduct of acrylic acid include acrylic acid dimer, methacrylic acid dimer, Examples include acrylic acid trimer, methacrylic acid trimer, acrylic acid tetramer, and methacrylic acid tetramer. Examples of the 2-acryloyloxyethyl dicarboxylic acid monoester that is a carboxylic acid having a specific substituent include 2-acryloyloxyethyl succinic acid monoester, 2-methacryloyloxyethyl succinic acid monoester, and 2-acryloyloxy. Examples thereof include ethylphthalic acid monoester, 2-methacryloyloxyethylphthalic acid monoester, 2-acryloyloxyethyl hexahydrophthalic acid monoester, and 2-methacryloyloxyethyl hexahydrophthalic acid monoester. Furthermore, oligoester acrylate is also mentioned.

  The bifunctional monomer may be any monomer containing two ethylenically unsaturated groups. For example, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene Glycol di (meth) acrylate, propylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, butylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, ethylene Oxide modified bisphenol A type di (meth) acrylate, propylene oxide modified bisphenol A type di (meth) acrylate, 1,6-hexanediol di (meth) acrylate 1,6-hexanediol ethylene oxide modified di (meth) acrylate, glycerin di (meth) acrylate, pentaerythritol di (meth) acrylate, ethylene glycol diglycidyl ether di (meth) acrylate, diethylene glycol diglycidyl ether di ( (Meth) acrylate, diglycidyl phthalate di (meth) acrylate, hydroxypivalic acid-modified neopentyl glycol di (meth) acrylate, isocyanuric acid ethylene oxide-modified diacrylate, 2- (meth) acryloyloxyethyl acid phosphate diester It is done.

  The tri- or higher functional monomer may be any monomer containing three or more ethylenically unsaturated groups. For example, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) ) Acrylate, dipentaerythritol tri (meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tri (meth) acryloyloxyethoxytrimethylolpropane, Glycerin polyglycidyl ether poly (meth) acrylate, isocyanuric acid ethylene oxide modified tri (meth) acrylate, ethylene oxide modified dipentaerythritol (Meth) acrylate, ethylene oxide modified dipentaerythritol hexa (meth) acrylate, ethylene oxide modified pentaerythritol tri (meth) acrylate, ethylene oxide modified pentaerythritol tetra (meth) acrylate, succinic acid modified pentaerythritol tri (meth) acrylate Etc.

  It is also preferable to use a compound in which an oxyalkylene chain is contained in the ethylenically unsaturated monomer (d2).

  Among the unsaturated group-containing compounds (D), a urethane (meth) acrylate compound (d1) or an ethylenically unsaturated monomer (d2) containing an oxyalkylene chain is used in that it exhibits excellent antistatic performance. Is also preferable. In particular, an unsaturated group-containing compound containing an oxyalkylene chain and containing 3 or more unsaturated groups is preferred.

  In addition, it is also preferable to use a (meth) acrylate compound containing an acid-base ion pair and / or a betaine structure in the molecule as the unsaturated group-containing compound (D) from the viewpoint of further improving the antistatic ability. .

  These unsaturated group containing compounds (D) may be used independently and may use 2 or more types together.

  As content of the said unsaturated group containing compound (D), 2-99 weight part is preferable with respect to 100 weight part of acrylic resin (A), More preferably, it is 5-50 weight part, More preferably, it is 8-30. Parts by weight. When there is too much content of the said unsaturated group containing compound (D), compatibility with resin will worsen, the tendency which the coating film whitens will be seen, or the crosslinking density will rise too much and adhesive force will fall too much. Therefore, there is a tendency that peeling is likely to occur in the durability test. When the amount is too small, the crosslinking density of the pressure-sensitive adhesive becomes insufficient, and the light leakage prevention property and durability tend to decrease.

  As the polymerization initiator (E), for example, various polymerization initiators such as a photopolymerization initiator (e1) and a thermal polymerization initiator (e2) can be used, and in particular, a photopolymerization initiator ( Use of e1) is preferable in that it can be crosslinked (cured) by irradiation with active energy rays such as ultraviolet rays for a very short time.

  Moreover, when using the said photoinitiator (e1), adhesive composition [I] is bridge | crosslinked by active energy ray irradiation, and when using a thermal polymerization initiator (e2), an adhesive composition [ I] is cross-linked, but it is also preferable to use both together if necessary.

  Examples of the photopolymerization initiator (e1) include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethyl ketal, 4- (2-hydroxyethoxy) phenyl- (2 -Hydroxy-2-propyl) ketone, 1-hydroxycyclohexyl phenylketone, 2-methyl-2-morpholino (4-thiomethylphenyl) propan-1-one, 2-benzyl-2-dimethylamino-1- (4- Acetophenones such as morpholinophenyl) butanone and 2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl] propanone oligomer; benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl Ben such as ether Ins; benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyl-diphenyl sulfide, 3,3 ', 4,4'-tetra (t-butylperoxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone, 4-benzoyl-N, N-dimethyl-N- [2- (1-oxo-2-propenyloxy) ethyl] benzenemethananium bromide, (4-benzoylbenzyl) trimethylammonium Benzophenones such as chloride; 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone, 2- (3-dimethylamino-2-hydroxy -3 Thioxanthones such as 4-dimethyl-9H-thioxanthone-9-one mesochloride; 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, bis (2,6-dimethoxybenzoyl) -2,4,4-trimethyl- Examples thereof include acyl phosphine oxides such as pentyl phosphine oxide and bis (2,4,6-trimethylbenzoyl) -phenyl phosphine oxide. In addition, as for these photoinitiators (d1), only 1 type may be used independently and 2 or more types may be used together.

  These auxiliary agents include triethanolamine, triisopropanolamine, 4,4′-dimethylaminobenzophenone (Michler ketone), 4,4′-diethylaminobenzophenone, 2-dimethylaminoethylbenzoic acid, 4-dimethylaminobenzoic acid. Ethyl, 4-dimethylaminobenzoic acid (n-butoxy) ethyl, isoamyl 4-dimethylaminobenzoate, 2-ethylhexyl 4-dimethylaminobenzoate, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone Etc. can be used in combination.

  Among these, benzyl dimethyl ketal, 1-hydroxycyclohexyl phenyl ketone, benzoyl isopropyl ether, 4- (2-hydroxyethoxy) -phenyl (2-hydroxy-2-propyl) ketone, 2-hydroxy-2-methyl-1- It is preferable to use phenylpropan-1-one.

  Examples of the thermal polymerization initiator (e2) include methyl ethyl ketone peroxide, cyclohexanone peroxide, methyl cyclohexanone peroxide, methyl acetoacetate peroxide, acetyl acetate peroxide, 1,1-bis (t-hexyl peroxide). ) -3,3,5-trimethylcyclohexane, 1,1-bis (t-hexylperoxy) -cyclohexane, 1,1-bis (t-butylperoxy) -3,3,5-trimethylcyclohexane, 1, 1-bis (t-butylperoxy) -2-methylcyclohexane, 1,1-bis (t-butylperoxy) -cyclohexane, 1,1-bis (t-butylperoxy) cyclododecane, 1,1- Bis (t-butylperoxy) butane, 2,2-bis (4 -Di-t-butylperoxycyclohexyl) propane, p-menthane hydroperoxide, diisopropylbenzene hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, cumene hydroperoxide, t-hexyl hydroper Oxide, t-butyl hydroperoxide, α, α′-bis (t-butylperoxy) diisopropylbenzene, dicumyl peroxide, 2,5-dimethyl-2,5-bis (t-butylperoxy) hexane, t-Butyl cumyl peroxide, di-t-butyl peroxide, 2,5-dimethyl-2,5-bis (t-butylperoxy) hexyne-3, isobutyryl peroxide, 3,5,5-trimethylhexa Noyl peroxide, octanoyl per Oxide, lauroyl peroxide, stearoyl peroxide, succinic acid peroxide, m-toluoyl benzoyl peroxide, benzoyl peroxide, di-n-propyl peroxydicarbonate, diisopropyl peroxydicarbonate, bis (4-t-butyl) (Cyclohexyl) peroxydicarbonate, di-2-ethoxyethyl peroxydicarbonate, di-2-ethoxyhexyl peroxydicarbonate, di-3-methoxybutyl peroxydicarbonate, di-s-butyl peroxydicarbonate, Di (3-methyl-3-methoxybutyl) peroxydicarbonate, α, α'-bis (neodecanoylperoxy) diisopropylbenzene, cumylperoxyneodecanoate, 1,1,3,3-te Lamethylbutyl peroxyneodecanoate, 1-cyclohexyl-1-methylethylperoxyneodecanoate, t-hexylperoxyneodecanoate, t-butylperoxyneodecanoate, t-hexylperoxy Pivalate, t-butylperoxypivalate, 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate, 2,5-dimethyl-2,5-bis (2-ethylhexanoylper) Oxy) hexanoate, 1-cyclohexyl-1-methylethylperoxy-2-ethylhexanoate, t-hexylperoxy-2-ethylhexanoate, t-butylperoxy-2-ethylhexanoate, t- Hexyl peroxyisopropyl monocarbonate, t-butyl peroxyisobutyrate t-butyl peroxymalate, t-butyl peroxy-3,5,5-trimethylhexanoate, t-butyl peroxylaurate, t-butyl peroxyisopropyl monocarbonate, t-butyl peroxy-2 -Ethylhexyl monocarbonate, t-butyl peroxyacetate, t-butyl peroxy-m-toluylbenzoate, t-butyl peroxybenzoate, bis (t-butylperoxy) isophthalate, 2,5-dimethyl-2,5 -Bis (m-toluylperoxy) hexane, t-hexylperoxybenzoate, 2,5-dimethyl-2,5-bis (benzoylperoxy) hexane, t-butylperoxyallyl monocarbonate, t-butyltrimethylsilylper Oxide, 3,3 ', 4,4'-tetra Organic peroxide initiators such as (t-butylperoxycarbonyl) benzophenone and 2,3-dimethyl-2,3-diphenylbutane; 2-phenylazo-4-methoxy-2,4-dimethylvaleronitrile, 1- [(1-cyano-1-methylethyl) azo] formamide, 1,1′-azobis (cyclohexane-1-carbonitrile), 2,2′-azobis (2-methylbutyronitrile), 2,2′- Azobisisobutyronitrile, 2,2'-azobis (2,4-dimethylvaleronitrile), 2,2'-azobis (2-methylpropionamidine) dihydrochloride, 2,2'-azobis (2-methyl- N-phenylpropionamidine) dihydrochloride, 2,2'-azobis [N- (4-chlorophenyl) -2-methylpropionamidine] Hydride chloride, 2,2'-azobis [N- (4-hydrophenyl) -2-methylpropionamidine] dihydrochloride, 2,2'-azobis [2-methyl-N- (phenylmethyl) propionamidine] dihydrochloride 2,2'-azobis [2-methyl-N- (2-propenyl) propionamidine] dihydrochloride, 2,2'-azobis [N- (2-hydroxyethyl) -2-methylpropionamidine] dihydrochloride, 2,2'-azobis [2- (5-methyl-2-imidazolin-2-yl) propane] dihydrochloride, 2,2'-azobis [2- (2-imidazolin-2-yl) propane] dihydrochloride, 2,2'-azobis [2- (4,5,6,7-tetrahydro-1H-1,3-diazepin-2-yl) Lopan] dihydrochloride, 2,2'-azobis [2- (3,4,5,6-tetrahydropyrimidin-2-yl) propane] dihydrochloride, 2,2'-azobis [2- (5-hydroxy-3 , 4,5,6-tetrahydropyrimidin-2-yl) propane] dihydrochloride, 2,2'-azobis [2- [1- (2-hydroxyethyl) -2-imidazolin-2-yl] propane] dihydrochloride 2,2'-azobis [2- (2-imidazolin-2-yl) propane], 2,2'-azobis [2-methyl-N- [1,1-bis (hydroxymethyl) -2-hydroxyethyl] ] Propionamide], 2,2'-azobis [2-methyl-N- [1,1-bis (hydroxymethyl) ethyl] propionamide], 2,2'-azobis [2-me Til-N- (2-hydroxyethyl) propionamide], 2,2'-azobis (2-methylpropionamide), 2,2'-azobis (2,4,4-trimethylpentane), 2,2'- Azobis (2-methylpropane), dimethyl-2,2-azobis (2-methylpropionate), 4,4'-azobis (4-cyanopentanoic acid), 2,2'-azobis [2- (hydroxymethyl And azo initiators such as propionitrile]. In addition, only 1 type may be used independently for these thermal polymerization initiators, and 2 or more types may be used together.

  About content of the said polymerization initiator (E), 0.01-10 weight part with respect to 100 weight part of said acrylic resins (A), Especially 0.1-7 weight part, Furthermore, 0.3 It is preferably ~ 3 parts by weight. If the content of the polymerization initiator (E) is too small, the curability tends to be poor and the physical properties tend to become unstable, and if it is too much, no further effect can be obtained.

  In the active energy ray irradiation, far ultraviolet rays, ultraviolet rays, near ultraviolet rays, infrared rays and other electromagnetic waves, X rays, γ rays and other electromagnetic waves, as well as electron beams, proton rays, neutron rays, etc. can be used. Curing by ultraviolet irradiation is advantageous from the standpoint of availability of the device and price. In addition, when performing electron beam irradiation, it can harden | cure even without using the said photoinitiator (e1).

As a light source for the ultraviolet irradiation, a high pressure mercury lamp, an electrodeless lamp, an ultrahigh pressure mercury lamp, a carbon arc lamp, a xenon lamp, a metal halide lamp, a chemical lamp, a black light, or the like is used. In the case of the high-pressure mercury lamp, for example, it is performed under conditions of 5 to 3000 mJ / cm ² , preferably 10 to 1000 mJ / cm ² . Moreover, in the case of the said electrodeless lamp, it is performed on the conditions of 2-1500 mJ / cm < ² >, for example, Preferably it is 5-500 mJ / cm < ² >. The irradiation time varies depending on the type of the light source, the distance between the light source and the coating surface, the coating thickness, and other conditions, but may be usually from several seconds to several tens of seconds, and in some cases, may be a fraction of a second. On the other hand, in the case of the electron beam irradiation, for example, an electron beam having an energy in the range of 50 to 1000 Kev is used, and the irradiation amount is preferably 2 to 50 Mrad.

  Moreover, when using a thermal-polymerization initiator (e2) as said polymerization initiator (E), a polymerization reaction is started and advanced by heating. The processing temperature and processing time at the time of crosslinking by heating are different depending on the type of the thermal polymerization initiator (e2) used, and are usually calculated from the half-life of the initiator. The temperature is preferably 70 ° C to 170 ° C, and the treatment time is usually preferably 0.2 to 20 minutes, and particularly preferably 0.5 to 10 minutes.

Next, the method [β], that is, the method of crosslinking using the crosslinking agent (F) will be described.
In the case of crosslinking using the crosslinking agent (F), in addition to the acrylic resin (A), the ionic compound (B) and the oxyalkylene group-containing compound (C) as the pressure-sensitive adhesive composition [I], The pressure-sensitive adhesive composition [I] containing the crosslinking agent (F) is used.

  When the crosslinking agent (F) is used, the acrylic resin (A) preferably has a functional group, and crosslinking (chemical crosslinking) is performed by reacting the functional group with the crosslinking agent.

  As said crosslinking agent (F), what is necessary is just a compound which has a functional group which reacts with the functional group contained in the said acrylic resin (A), for example, an isocyanate type compound, an epoxy-type compound, an aziridine type compound, a melamine type Examples include compounds, aldehyde compounds, amine compounds, and metal chelate compounds. Among these, an isocyanate compound is preferably used from the viewpoint of improving the adhesion to the base material and the reactivity with the base polymer.

  Examples of the isocyanate compound include 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, hydrogenated tolylene diisocyanate, 1,3-xylylene diisocyanate, 1,4-xylylene diisocyanate, and hexamethylene diisocyanate. , Diphenylmethane-4,4-diisocyanate, isophorone diisocyanate, 1,3-bis (isocyanatomethyl) cyclohexane, tetramethylxylylene diisocyanate, 1,5-naphthalene diisocyanate, triphenylmethane triisocyanate, and polyisocyanate compounds thereof Examples thereof include adducts with polyol compounds such as trimethylolpropane, burettes and isocyanurates of these polyisocyanate compounds.

  Examples of the epoxy compound include bisphenol A / epichlorohydrin type epoxy resin, ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, glycerin diglycidyl ether, glycerin triglycidyl ether, 1,6-hexanediol diglycidyl ether, Examples include trimethylolpropane triglycidyl ether, sorbitol polyglycidyl ether, polyglycerol polyglycidyl ether, pentaerythritol polyglycidyl erythritol, diglycerol polyglycidyl ether, and the like.

  Examples of the aziridine compound include tetramethylolmethane-tri-β-aziridinylpropionate, trimethylolpropane-tri-β-aziridinylpropionate, N, N′-diphenylmethane-4,4 ′. -Bis (1-aziridinecarboxamide), N, N'-hexamethylene-1,6-bis (1-aziridinecarboxyamide) and the like.

  Examples of the melamine compounds include hexamethoxymethyl melamine, hexaethoxymethyl melamine, hexapropoxymethyl melamine, hexaptoxymethyl melamine, hexapentyloxymethyl melamine, hexahexyloxymethyl melamine, and melamine resin.

  Examples of the aldehyde compounds include glyoxal, malondialdehyde, succindialdehyde, maleindialdehyde, glutardialdehyde, formaldehyde, acetaldehyde, benzaldehyde and the like.

  Examples of the amine compound include hexamethylenediamine, triethyldiamine, polyethyleneimine, hexamethylenetetraamine, diethylenetriamine, triethyltetraamine, isophoronediamine, amino resin, polyamide, and the like.

  Examples thereof include multimetallic acetylacetone and acetoacetyl ester coordination compounds such as aluminum, iron, copper, zinc, tin, titanium, nickel, antimony, magnesium, panadium, chromium and zirconium.

  Moreover, these crosslinking agents (F) may be used independently and may be used together 2 or more types.

  The content of the crosslinking agent (F) can be appropriately selected depending on the amount of the functional group contained in the acrylic resin (A), the molecular weight of the acrylic resin (A), and the purpose of use. (A) It is preferable that it is 0.1-15 weight part with respect to 100 weight part, Furthermore, 0.2-12 weight part, Especially 1.5-10 weight part, Especially 0.5- It is preferably 3 parts by weight. When the amount of the crosslinking agent (F) is too small, there is a tendency that the cohesive force is insufficient and sufficient durability cannot be obtained. When the amount is too large, the flexibility and adhesive strength are lowered, the durability is deteriorated, and peeling is caused. Tends to occur, and it tends to be difficult to bond to an optical film.

  In the present invention, in order to further improve the antistatic performance of the pressure-sensitive adhesive obtained by crosslinking the pressure-sensitive adhesive composition [I], a part of the crosslinking agent (F) has a structure having antistatic performance. It is also preferable to use a cross-linking agent having an introduced site.

  In the present invention, sufficient crosslinking can be obtained only by the above-mentioned [α] active energy rays and / or heat (irradiation and / or heating of active energy rays). It is preferable to use in combination, and the cross-linking density of the pressure-sensitive adhesive is increased and the cohesive force is increased, so that a further superior one in terms of prevention of light leakage and durability can be obtained.

  Moreover, in this invention, it is preferable at the point which the adhesiveness with respect to an optical member improves to contain a silane coupling agent (G) further as adhesive composition [I] which is an adhesive formation material. As content of the said silane coupling agent (G), it is 0.001-10 weight part normally with respect to 100 weight part of acrylic resin (A), More preferably, 0.01-1 weight part, Particularly preferred is 0.03 to 0.8 parts by weight. If the content of the silane coupling agent (G) is too small, there is a tendency that the addition effect cannot be obtained. If the content is too large, the compatibility with the acrylic resin (A) is lowered, and adhesive strength and cohesive strength are obtained. There is a tendency to disappear.

  Examples of the silane coupling agent (G) include an epoxy silane coupling agent, an acrylic silane coupling agent, a mercapto silane coupling agent, a hydroxyl group silane coupling agent, a carboxyl group silane coupling agent, and amino. Examples thereof include a base silane coupling agent, an amide group silane coupling agent, and an isocyanate group silane coupling agent. These may be used alone or in combination of two or more. Among these, an epoxy silane coupling agent and a mercapto silane coupling agent are preferably used, and the combined use of an epoxy silane coupling agent and a mercapto silane coupling agent also improves wet heat durability and has adhesive strength. It is preferable in that it does not rise too much.

  Specific examples of the epoxy-based silane coupling agent include, for example, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, γ-glycidoxypropylmethyldiethoxysilane, and γ-glycid. Examples include xylpropylmethyldimethoxysilane, methyltri (glycidyl) silane, β- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, β- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, and the like. -Glycidoxypropyltrimethoxysilane, [gamma] -glycidoxypropyltriethoxysilane, [gamma] -glycidoxypropylmethyldiethoxysilane, [beta]-(3,4-epoxycyclohexyl) ethyltrimethoxysilane.

  Specific examples of the mercapto silane coupling agent include γ-mercaptopropyltrimethoxysilane, γ-mercaptopropyltriethoxysilane, and γ-mercaptopropyldimethoxymethylsilane.

  In the present invention, the pressure-sensitive adhesive composition [I], which is a pressure-sensitive adhesive forming material, may further contain an antistatic agent (H) other than the ionic compound (B) described above. This is preferable in that the performance is further improved. Examples of the antistatic agent (H) include imidazolium salts (excluding (B)), quaternary ammonium salt cationic antistatic agents such as tetraalkylammonium sulfonates, aliphatic sulfonates, and higher grades. Anionic antistatic agents such as alcohol sulfate ester salts, higher alcohol alkylene oxide adduct sulfate salts, higher alcohol phosphate ester salts, higher alcohol alcohol alkylene oxide adduct phosphate ester salts, lithium perchlorate, lithium chloride, etc. Examples include alkali metal salts, alkaline earth metal salts, higher alcohol alkylene oxide adducts, polyalkylene glycol fatty acid esters, and the like of organic acids or inorganic acids.

  The content of the antistatic agent (H) is usually 0.001 to 20 parts by weight, more preferably 0.01 to 10 parts by weight, particularly 100 parts by weight of the acrylic resin (A). Preferably it is 0.02-5 weight part. If the content of the antistatic agent (H) is too small, the effect of addition tends not to be obtained, and if it is too large, the durability may be lowered or the antistatic agent may bleed out.

In the present invention, the pressure-sensitive adhesive composition [I], which is a pressure-sensitive adhesive-forming material, further includes other acrylic pressure-sensitive adhesives, other pressure-sensitive adhesives, urethane resins, rosins, and rosins, as long as the effects of the present invention are not impaired. Esters, hydrogenated rosin esters, phenol resins, aromatic modified terpene resins, aliphatic petroleum resins, alicyclic petroleum resins, styrene resins, xylene resins, tackifiers, colorants, fillers, anti-aging Conventionally known additives such as an agent, an ultraviolet absorber, a functional dye, and the like, and a compound that causes coloration or discoloration upon irradiation with ultraviolet rays or radiation can be blended.
In addition to the above additives, a small amount of impurities contained in the raw materials for producing the constituent components of the pressure-sensitive adhesive composition [I] may be contained.

Thus, in the present invention, a pressure-sensitive adhesive obtained by crosslinking the pressure-sensitive adhesive composition [I] is obtained.
In addition to the crosslinking method described above, the crosslinking method of the pressure-sensitive adhesive composition [I] containing the acrylic resin (A), the ionic compound (B) and the oxyalkylene group-containing compound (C) The pressure-sensitive adhesive composition [I] can be cross-linked by a method of irradiating active energy rays without substantially containing an unsaturated group. In addition, it is preferable for the reason similar to the above to contain a polymerization initiator (E), a crosslinking agent (F), and a silane coupling agent (G) at this time.

  And the optical member with an adhesive layer can be obtained by carrying out the lamination formation of the adhesive layer which consists of the said adhesive on an optical member (optical laminated body).

  It is preferable that the optical member with the pressure-sensitive adhesive layer is further provided with a release sheet on the surface opposite to the optical member surface of the pressure-sensitive adhesive layer.

  As a manufacturing method of the said optical member with an adhesive layer, after apply | coating and drying adhesive composition [I] on an optical member, for example, the method of further bonding a release sheet, or [2] The adhesive composition [I] can be applied to the release sheet, dried, and then manufactured by a method of bonding an optical member. Especially, the manufacturing method which apply | coats adhesive composition [I] on a release sheet which is the method of said [2] is preferable at the point with a low possibility of degrading an optical member with a dilution solvent.

  Moreover, when using the optical member with an adhesive layer for practical use, the said release sheet is peeled and used. And as said release sheet, it is preferable to use a silicon-type release sheet.

  In the case where the pressure-sensitive adhesive composition [I] is crosslinked by at least one of active energy ray irradiation and heating, [1] after the pressure-sensitive adhesive composition [I] is applied on the optical member and dried, A method in which a release sheet is bonded and a treatment by at least one of active energy ray irradiation and heating is performed. [2] On the release sheet, the adhesive composition [I] is applied and dried, and then an optical member is applied. And a method of performing treatment by at least one of active energy ray irradiation and heating, and [3] applying and drying the adhesive composition [I] on the optical member, and further performing treatment by at least one of active energy ray irradiation and heating. [4] The adhesive composition [I] is applied on the release sheet, dried, and further treated by at least one of irradiation with active energy rays and heating. After performing, it can be to produce a method of bonding an optical member, a. Among these, the case of performing only the active energy ray irradiation by the method [2] is preferable from the viewpoint of not damaging the substrate, workability and stable production.

  When applying the pressure-sensitive adhesive composition [I], it is preferable to dilute the pressure-sensitive adhesive composition [I] in a solvent, and the dilution concentration is preferably 5 to 60% by weight, particularly preferably 10%. ~ 30% by weight. The solvent is not particularly limited as long as it can dissolve the pressure-sensitive adhesive composition [I]. Examples thereof include ester solvents such as methyl acetate, ethyl acetate, methyl acetoacetate, and ethyl acetoacetate, acetone Further, ketone solvents such as methyl ethyl ketone and methyl isobutyl ketone, aromatic solvents such as toluene and xylene, and alcohol solvents such as methanol, ethanol and propyl alcohol can be used. Among these, ethyl acetate and methyl ethyl ketone are preferably used from the viewpoints of solubility, drying property, price, and the like.

  In addition, the application of the pressure-sensitive adhesive composition [I] is performed by a conventional method such as roll coating, die coating, gravure coating, comma coating, or screen printing.

  About the gel fraction of the adhesive layer manufactured by the said method, adhesive composition [I] contains an unsaturated group containing compound (D) and a polymerization initiator (E), an active energy ray and / or In the case of crosslinking by heat, it is preferably 70% or more, particularly 90% or more from the viewpoint of durability performance and light leakage prevention performance. If the gel fraction is too low, the durability and light leakage phenomenon due to insufficient cohesive force tend to be deteriorated. In general, the upper limit of the gel fraction is 100%.

  Further, when the pressure-sensitive adhesive composition [I] contains a crosslinking agent (F) and is crosslinked with a crosslinking agent, it does not contain an unsaturated group-containing compound (D) and a polymerization initiator (E). The gel fraction of the pressure-sensitive adhesive layer produced by the above method is preferably 20 to 90%, particularly preferably 30 to 80% from the viewpoint of the balance between durability and light leakage prevention performance. It is preferably 40 to 70%, particularly preferably 50 to 60%. If the gel fraction is too low, durability tends to be insufficient due to insufficient cohesive force. If the gel fraction is too high, light leakage due to increased cohesive force tends to deteriorate.

  In adjusting the gel fraction of the optical member pressure-sensitive adhesive to the above range, for example, adjusting the irradiation amount and irradiation intensity of the active energy ray, adjusting the type and amount of the unsaturated group-containing compound, This is achieved by adjusting the type of polymerization initiator and the combination ratio thereof, adjusting the blending amount of the polymerization initiator, adjusting the type and amount of the crosslinking agent, and the like. Moreover, since the gel fraction changes by each interaction, the irradiation amount and irradiation intensity | strength of said active energy ray, the composition ratio of a polymerization initiator, and addition amount need to balance each.

  The gel fraction is a measure of the degree of crosslinking, and is calculated, for example, by the following method. That is, a pressure-sensitive adhesive sheet (not provided with a separator) in which a pressure-sensitive adhesive layer is formed on a polymer sheet (for example, polyethylene terephthalate film or the like) as a base material is wrapped with a 200-mesh SUS wire mesh, and 23 in toluene. The weight percentage of the insoluble pressure-sensitive adhesive component immersed in the wire mesh at 24 ° C. for 24 hours is defined as the gel fraction. However, the weight of the substrate is subtracted.

  Moreover, 5-300 micrometers is preferable normally, and, as for the thickness of the adhesive layer in the optical member with an adhesive layer obtained, 10-50 micrometers is especially preferable, Furthermore, 12-30 micrometers is preferable. If the thickness of the pressure-sensitive adhesive layer is too thin, the adhesive physical properties tend to be difficult to stabilize, and if it is too thick, the thickness of the entire optical member tends to increase.

  The optical member with the pressure-sensitive adhesive layer of the present invention has a release sheet, and after the release sheet has been peeled off, the pressure-sensitive adhesive layer surface is bonded to a glass substrate and used for, for example, a liquid crystal display panel.

  In the present invention, the initial adhesive strength of the pressure-sensitive adhesive layer is appropriately determined according to the material of the adherend. For example, when sticking on a glass substrate, it preferably has an adhesive strength of 0.2 N / 25 mm to 20 N / 25 mm, and more preferably 0.5 N / 25 mm to 10 N / 25 mm.

  The initial adhesive force is calculated as follows, for example. About a polarizing plate with an adhesive layer, it cut | judged to width 25mm width, peels a release film, presses the adhesive layer side to a non-alkali glass plate (Corning company make, "Corning 1737"), and a polarizing plate A glass plate is bonded. Then, after performing an autoclave process (50 degreeC, 0.5 MPa, 20 minutes), 23 degreeC and 50% R. H. After leaving for 24 hours, a 180 degree peel test is performed.

  The optical member in the present invention is not particularly limited, and an optical film suitably used for an image display device such as a liquid crystal display device, an organic EL display device, or a PDP, such as a polarizing plate, a retardation plate, or an elliptical polarizing plate. , Optical compensation films, brightness enhancement films, and those in which these are laminated. Among them, a polarizing plate is particularly effective in the present invention.

  The polarizing plate used in the present invention is usually a laminate of a cellulose triacetate film as a protective film on both sides of a polarizing film. The polarizing film has an average degree of polymerization of 1,500 to 10,000, A uniaxially stretched film dyed with an aqueous solution of iodine-potassium iodide or a dichroic dye using a film made of a polyvinyl alcohol resin having a degree of conversion of 85 to 100 mol% as a raw film (usually 2 to 10 times, preferably Is a stretching ratio of about 3 to 7 times.

  The polyvinyl alcohol resin is usually produced by saponifying polyvinyl acetate obtained by polymerizing vinyl acetate, but a small amount of unsaturated carboxylic acid (including salt, ester, amide, nitrile, etc.), olefins, vinyl ether And a component copolymerizable with vinyl acetate, such as an unsaturated sulfonate. Moreover, what is called polyvinyl acetal resin and polyvinyl alcohol derivatives, such as polybutyral resin and polyvinyl formal resin, which are obtained by reacting polyvinyl alcohol with an aldehyde in the presence of an acid are also exemplified.

  Although the case where the pressure-sensitive adhesive of the present invention is used for optical member applications has been described in detail so far, the pressure-sensitive adhesive of the present invention can also be used as a temporary surface protection pressure-sensitive adhesive in temporary surface protection applications. Since it is useful in terms of high-speed peelability depending on the case, an explanation about the use of the pressure-sensitive adhesive of the present invention for temporary surface protection will be described below.

  When used as a temporary surface-protecting pressure-sensitive adhesive, the pressure-sensitive adhesive composition [I] includes the acrylic resin (A), an ionic compound (B) component having a bis (fluorosulfonyl) imide anion, and an oxyalkylene. The group-containing compound (C) may be cured with an electron beam, and in addition, at least one of an unsaturated group-containing compound (D), a polymerization initiator (E), and a crosslinking agent (F) component is contained. The pressure-sensitive adhesive composition [I] is preferably crosslinked to form a pressure-sensitive adhesive. Further, the acrylic resin (A), the ionic compound (B) having a bis (fluorosulfonyl) imide anion, and an oxyalkylene group In addition to the containing compound (C) and the crosslinking agent (F) component, the pressure-sensitive adhesive composition [I] containing the unsaturated group-containing compound (D) and the polymerization initiator (E) is crosslinked to form a pressure-sensitive adhesive. Rukoto is particularly preferred.

  As the acrylic resin (A) used as the temporary surface protecting adhesive, the same acrylic resin (A) as described above can be used.

  As the unsaturated group-containing compound (D) when used as such a temporary surface-protecting pressure-sensitive adhesive, the same unsaturated group-containing compound (D) as described above can be used. In order to increase the density, it is preferable to use a polyfunctional, that is, an unsaturated group-containing compound having 2 or more unsaturated groups, more preferably an unsaturated group-containing compound having 3 or more unsaturated groups. An unsaturated group-containing compound having 4 or more saturated groups is preferred, and an unsaturated group-containing compound having 5 or more unsaturated groups is particularly preferred.

  Moreover, it is also preferable to use the urethane (meth) acrylate type compound and the ethylenically unsaturated monomer containing an alkylene glycol chain at the point which shows the outstanding antistatic performance. In particular, urethane (meth) acrylate compounds containing an alkylene glycol chain and containing 3 or more unsaturated groups are preferred.

  As content of an unsaturated group containing compound (D), it is preferable that it is 200 weight part or less with respect to 100 weight part of acrylic resin (A), More preferably, it is 5-150 weight part, More preferably, it is 10-weight part. 100 parts by weight, particularly preferably 20 to 80 parts by weight. If the content of the unsaturated group-containing compound (D) is too small, the crosslinking is insufficient and the cohesive force tends to be reduced, causing contamination of the adherend. If the content is too large, the adhesive strength tends to be reduced. .

  As the polymerization initiator (E) when used as the temporary surface protecting pressure-sensitive adhesive, those similar to the polymerization initiator (E) described above can be used.

  As the crosslinking agent (F) when used as the temporary surface protecting adhesive, the same crosslinking agent (F) as described above can be used.

  The temporary surface protecting adhesive obtained by curing the above-mentioned adhesive composition [I] can be usefully used as a temporary surface protecting adhesive sheet by laminating on the substrate.

  The “sheet” in the present invention includes a film.

  There is no restriction | limiting in particular as a base material which provides the said adhesive composition [I], For example, polyester-type resin, such as polyethylene naphthalate, a polyethylene terephthalate, a boribylene terephthalate, a polyethylene terephthalate / isophthalate copolymer; Polyethylene, polypropylene Polyolefin resins such as polymethylpentene; Polyfluorinated ethylene resins such as polyvinyl fluoride, polyvinylidene fluoride, and polyfluorinated ethylene; Polyamides such as nylon 6, nylon 6, 6; Polyvinyl chloride, polyvinyl chloride / vinyl acetate Polymers, ethylene-vinyl acetate copolymers, ethylene-vinyl alcohol copolymers, vinyl polymers such as polyvinyl alcohol and vinylon; cellulose resins such as cellulose triacetate and cellophane; polymethyl methacrylate, poly Acrylic resins such as ethyl methacrylate, polyethyl acrylate, and polybutyl acrylate; polystyrene; polycarbonate; polyarylate; synthetic resin film or sheet such as polyimide, aluminum, copper, iron metal foil, fine paper, glassine paper, etc. And woven and non-woven fabrics made of paper, glass fiber, natural fiber, synthetic fiber and the like. These base materials can be used as a single layer body or a multilayer body in which two or more kinds are laminated.

  Among these base materials, a synthetic resin film or sheet such as polyethylene terephthalate, polyethylene, or polypropylene is preferably used in consideration of price.

  In addition, in order to increase the anchoring property of the adhesive to the base material, the surface of the base material is treated to improve easy adhesion properties such as corona discharge treatment, plasma treatment, primer coating, degreasing treatment, and surface roughening treatment. Or an antistatic layer may be provided for further antistatic.

  Although the thickness of the said base material is not specifically limited, Generally it is 500 micrometers or less, Preferably it is 1-300 micrometers, More preferably, it is 5-200 micrometers, Especially preferably, the thickness of about 10-100 micrometers can be illustrated.

  The thickness of the pressure-sensitive adhesive composition [I] provided on the substrate is not particularly limited, but is generally 1 to 200 μm, preferably 2 to 100 μm, more preferably 3 to 50 μm, and particularly preferably 5 to 30 μm after drying. The thickness of the degree can be exemplified. If it is too thick, the adhesive tends to remain on the surface of the adherend when peeling the temporary surface-protecting pressure-sensitive adhesive sheet from the adherend, and if it is too thin, the adhesive force to the adherend will be reduced. After sticking the temporary surface protective adhesive sheet to the adherend, the temporary surface protective adhesive sheet tends to peel off when the adherend and temporary surface protective adhesive sheet are exposed to high temperatures. There is.

  A separator can be laminated on the surface of the pressure-sensitive adhesive for the purpose of protecting the pressure-sensitive adhesive from contamination until the temporary surface-protective pressure-sensitive adhesive sheet is bonded to the adherend. As a separator, what carried out mold release processing of base materials, such as the synthetic resin film or sheet | seat illustrated above, paper, cloth, and a nonwoven fabric, can be used.

  In providing the pressure-sensitive adhesive composition [I] on the substrate, it is usually applied as a solution of the pressure-sensitive adhesive composition [I], particularly to a viscosity suitable for application with a solvent, and then applied to the substrate. Drying is performed. As a method of coating, a direct application method in which the solution-like pressure-sensitive adhesive composition [I] is directly applied to a substrate, or a solution-type pressure-sensitive adhesive composition [I] is applied to a separator and then attached to a substrate. Examples of the transfer coating method are as follows.

  In the direct coating method, the pressure-sensitive adhesive composition [I] is applied to a base material, heated and dried, then irradiated with active energy rays, and then a separator is attached, or the pressure-sensitive adhesive composition [I] ], And after drying by heating, a separator is attached, and then an active energy ray is irradiated. Coating is performed by methods such as roll coating, die coating, gravure coating, comma coating, and screen printing.

  On the other hand, in the transfer coating method, the pressure-sensitive adhesive composition [I] is applied to the separator, heated and dried, then irradiated with active energy rays, and then the substrate is bonded to the pressure-sensitive adhesive composition [ After I] is applied and dried by heating, the substrates are bonded together, and then irradiated with active energy rays. About the coating method, the method similar to direct coating can be used.

  There are no particular restrictions on the type of adherend to which the temporary surface protecting adhesive sheet is applied, but for example, in addition to the metal foil, synthetic resin film or sheet, paper, woven fabric and non-woven fabric exemplified in the above substrate. Examples thereof include a glass plate, a synthetic resin plate, and a metal plate.

  The initial adhesive strength of the temporary surface protecting adhesive sheet is appropriately determined according to the material of the adherend. For example, when sticking to a SUS304BA board, it is preferable to have an adhesive strength of 0.01 N / 25 mm to 50 N / 25 mm, and when used for temporary protection (surface protection, masking) An adhesive force of 01 N / 25 mm to 5 N / 25 mm is preferable, and an adhesive force of 0.02 N / 25 mm to 1 N / 25 mm is particularly preferable.

  The adhesive strength is calculated as follows. First, the obtained pressure-sensitive adhesive sheet was cut into 25 mm × 100 mm, and this was then applied to a stainless steel plate (SUS304BA plate) or acrylic plate (PMMA plate) as an adherend in an atmosphere at 23 ° C. and 50% relative humidity. A test piece is prepared by pressure bonding by reciprocating twice using a 2 kg rubber roller. After leaving this test piece for 30 minutes under the same atmosphere, a 180 ° peel test is performed at a peel rate of 0.3 m / min, and the measured adhesive strength (N / 25 mm) is taken as the initial adhesive strength.

  Further, the high-speed peel adhesive strength of the temporary surface protecting adhesive sheet is usually 6 times or less of the initial adhesive force, particularly preferably 4 times or less, and more preferably 2 times or less. preferable. For such high-speed peel adhesion, a test piece prepared by the same method as the initial adhesion was left for 30 minutes in an atmosphere of 23 ° C. and 50% relative humidity. Thereafter, in the same atmosphere, a 180 ° peel test is performed at a high speed of 30 m / min, and the measured adhesive strength (N / 25 mm) is defined as the high speed peel adhesive strength.

  EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples. However, the present invention is not limited to the following examples unless it exceeds the gist. In the examples, “parts” and “%” mean weight basis unless otherwise specified.

  First, various acrylic resins and various unsaturated group-containing compounds were prepared as follows. In addition, regarding the measurement of the weight average molecular weight of acrylic resin, dispersion degree, and glass transition temperature, it measured according to the above-mentioned method. In addition, regarding the measurement of a viscosity, it measured according to the 4.5.3 rotational viscometer method of JISK5400 (1990).

[Preparation of acrylic resin (A)] (See Table 2)
[Acrylic resin (A-1)]
A 4-neck round bottom flask equipped with a reflux condenser, stirrer, nitrogen gas inlet and thermometer was charged with 100 parts of ethyl acetate, and 0.05 parts of azobisisobutyronitrile (AIBN) as a polymerization initiator. The mixture was heated with stirring, and at 78 ° C., a mixture of 30 parts of 2-hydroxyethyl acrylate (a1), 69 parts of butyl acrylate (a2) and 1 part of acrylic acid (a3) was added dropwise over 2 hours. During polymerization, while sequentially adding a polymerization initiator solution in which 0.05 part of AIBN was dissolved in 10 parts of ethyl acetate, the mixture was polymerized at the ethyl acetate reflux temperature for 3.5 hours, and then diluted with an acrylic resin (A-1 ) Solution (weight average molecular weight (Mw) 800,000, dispersity (Mw / Mn) 4.5, glass transition temperature −45 ° C., solid content 35%, viscosity 7,000 mPa · s (25 ° C.)).
In addition, about HLB of acrylic resin (A-1), it calculated | required by the following calculations and was 7.42.
-When 2-hydroxyethyl acrylate during polymerization is decomposed into each component,
(CH2: -0.475) (CH: -0.475) (COO: 2.4) (CH2: -0.475) (CH2: -0.475) (OH: 1.9)
HLB value = Σ number of hydrophobic machines + Σ number of hydrophilic groups + 7
= {(− 0.475) × 4} + {(2.4) + (1.9)} + 7
= 9.4
Similarly, when acrylic acid (CH2: -0.475) (CH: -0.475) (COOH: 2.1) is calculated,
HLB value = {(− 0.475) × 2} + (2.1) +7
= 8.15
Similarly, butyl acrylate (CH2: -0.475) (CH: -0.475) (COO: -2.4) (CH2: -0.475) (CH2: -0.475) (CH2:- 0.475) (CH3: -0.475)
HLB value = {(− 0.475) × 6} + (2.4) +7
= 6.55
・ Acrylic resin (A-1)
= BA / HEA / AAc
= 69/30/1, so when the above calculated value is multiplied by the content of each monomer,
HLB value = (6.55 × 69 + 9.4 × 30 + 8.15 × 1) / 100
= 7.42

[Acrylic resin (A-2)]
In a 4-neck round bottom flask equipped with a reflux condenser, a stirrer, a nitrogen gas inlet and a thermometer, 10 parts of 2-hydroxyethyl acrylate (a1), 40 parts of 2-methoxyethyl acrylate (a1), butyl acrylate (A2) 49 parts, acrylic acid (a3) 1 part and ethyl acetate 140 parts, acetone 45 parts were charged. After heating to reflux, azobisisobutyronitrile (AIBN) 0.03 part was added as a polymerization initiator, After reacting at reflux temperature for 3 hours, the reaction mixture was diluted with ethyl acetate and diluted with an acrylic resin (A-2) solution (weight average molecular weight (Mw) 1,200,000, dispersity (Mw / Mn) 4.3, glass transition temperature -49. C, solid content 20%, viscosity 5,000 mPa · s (25 ° C)).
The acrylic resin (A-2) had an HLB of 7.55.

[Acrylic resin (A-3)]
In a 4-neck round bottom flask equipped with a reflux condenser, a stirrer, a nitrogen gas inlet and a thermometer, 5 parts of 2-hydroxyethyl acrylate (a1), 94.5 parts of butyl acrylate (a2), acrylic acid ( a3) 0.5 parts, 100 parts of ethyl acetate and 45 parts of acetone were added, and after heating to reflux, 0.03 part of azobisisobutyronitrile (AIBN) was added as a polymerization initiator, and the mixture was refluxed at ethyl acetate for 3 hours. After the reaction, it was diluted with ethyl acetate, and the acrylic resin (A-3) solution (weight average molecular weight (Mw) 1.58 million, dispersity (Mw / Mn) 3.7, glass transition temperature −50 ° C., solid content 18 %, Viscosity 8,000 mPa · s (25 ° C.)).
In addition, regarding HLB of acrylic resin (A-3), it was 6.70.

[Acrylic resin (A-4)]
In a 4-neck round bottom flask equipped with a reflux condenser, a stirrer, a nitrogen gas inlet and a thermometer, 1.5 parts of 2-hydroxyethyl acrylate (a1), 98 parts of butyl acrylate (a2), acrylic acid ( a3) 0.5 parts, 100 parts of ethyl acetate and 45 parts of acetone were added, and after heating to reflux, 0.03 part of azobisisobutyronitrile (AIBN) was added as a polymerization initiator, and the mixture was refluxed at ethyl acetate for 3 hours. After the reaction, the solution was diluted with ethyl acetate, and the acrylic resin (A-4) solution (weight average molecular weight (Mw) 1,650,000, dispersity (Mw / Mn) 3.5, glass transition temperature -55 ° C. solid content 18% And a viscosity of 8,000 mPa · s (25 ° C.)).
The HLB of the acrylic resin (A-4) was 6.60.

[Ionic compound (B)]
The following were prepared as the ionic compound (B-1).
-Potassium bis (fluorosulfonyl) imide The following were prepared as an ionic compound (B'-1).
-Potassium bis (trifluoromethylsulfonyl) imide The following were prepared as an ionic compound (B'-2).
-Potassium bis (nonafluorobutyl sulfonyl) imide The following were prepared as an ionic compound (B'-3).
1-ethyl-3-methylimidazolium bis (nonafluorobutanesulfonyl) imide

  The ionic compounds (B-1), (B′-1), (B′-2) and (B′-3) are all solid at room temperature.

[Oxyalkylene group-containing compound (C)]
The following were prepared as the oxyalkylene group-containing compound (C-1).
Tetraethylene glycol dimethyl ether (Toho Chemical Industry Co., Ltd., “Hisolv MTEM”)

[Production of unsaturated group-containing compound (D-1)]
In a 4-neck round bottom flask equipped with a reflux condenser, a stirrer, a nitrogen gas inlet and a thermometer, 19.2 parts of isophorone diisocyanate, 0.05 part of di-t-butylhydroxyphenol, 0.02 of dibutyltin dilaurate The reaction was continued at 70 ° C. at a temperature of 50 ° C. or less and 80.8 parts of a mixture of pentaerythritol triacrylate and pentaerythritol tetraacrylate (Kyoeisha Chemical Co., Ltd., light acrylate PE-3A, hydroxyl value 120 mg KOH / g). Then, an unsaturated group-containing compound (D-1) was obtained.

[Photoinitiator (E)]
The following were prepared as the photopolymerization initiator (E-1).
A mixture of benzophenone and 1-hydroxycyclohexyl phenyl ketone in a mass ratio of 1: 1 (Ciba Specialty Chemicals, “Irgacure 500”)

[Crosslinking agent (F)]
The following were prepared as a crosslinking agent (F-1).
・ 55% ethyl acetate solution of trimethylolpropane tolylene diisocyanate adduct (manufactured by Nippon Polyurethane Co., Ltd., “Coronate L-55E”)

[Silane coupling agent (G)]
The following were prepared as the silane compound (G-1).
・ Γ-glycidoxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., “KBM403”)

[Examples 1 and 2 and Comparative Examples 1 to 4]
Each of the blended components prepared and prepared as described above is blended in the proportions shown in Tables 3 and 4 below to prepare a pressure-sensitive adhesive composition that becomes a pressure-sensitive adhesive forming material for an optical member. And diluted (viscosity [1000 to 10,000 mPa · s (25 ° C.)]) to prepare an adhesive composition solution.

And after apply | coating the said adhesive composition solution to the polyester-type release sheet so that the thickness after drying may be set to 25 micrometers, and drying for 3 minutes at 90 degreeC, the formed adhesive composition layer side is made into polyethylene. Transferred onto a terephthalate (PET) film (thickness 38 μm), and irradiated with ultraviolet rays at a peak illuminance of 600 mW / cm ² and an integrated exposure amount of 240 mJ / cm ² with a fusion-free electrodeless lamp [H bulb of LH6UV lamp] (120 mJ / cm ² × 2 passes), then 23 ° C. × 65% R.D. H. The film was aged for 10 days under the above conditions to obtain a PET film with an adhesive layer.

[Examples 3 to 5, Comparative Examples 5 and 6]
Each of the blended components prepared and prepared as described above is blended in the proportions shown in Tables 3 and 4 below to prepare a pressure-sensitive adhesive composition that becomes a pressure-sensitive adhesive forming material for an optical member. And diluted (viscosity [1000 to 10,000 mPa · s (25 ° C.)]) to prepare an adhesive composition solution.

  And after apply | coating the said adhesive composition solution to the polyester-type release sheet so that the thickness after drying may be set to 25 micrometers, and drying for 3 minutes at 90 degreeC, the formed adhesive composition layer side is made into polyethylene. After transfer onto a terephthalate (PET) film (thickness 38 μm), the film was transferred at 23 ° C. × 65% R.D. H. The film was aged for 10 days under the above conditions to obtain a PET film with an adhesive layer.

  Using the PET film with the pressure-sensitive adhesive layer thus obtained, the surface resistivity and gel fraction were measured and evaluated according to the following methods. These results are shown in Table 3 and Table 4 below.

[Surface resistivity]
The obtained PET film with the pressure-sensitive adhesive layer was cut into a size of 40 × 40 mm, and this was left to stand for 3 hours under conditions of a temperature of 23 ° C. and a relative humidity of 65%, and then the release sheet was peeled off. About the adhesive layer after 10 to 20 seconds, the surface resistivity was measured using a resistivity meter (manufactured by Mitsubishi Chemical Corporation, Hiresta UP). In addition, it means that antistatic performance is so high that surface resistivity is small.

[Gel fraction]
After the obtained PET film with the pressure-sensitive adhesive layer is cut into 40 × 40 mm, the release sheet is peeled off and the pressure-sensitive adhesive layer side is bonded to a 50 × 100 mm SUS mesh sheet (200 mesh), and then the SUS mesh sheet. The sample was wrapped from the center with respect to the longitudinal direction, and the sample was wrapped. Then, the gel fraction was measured by weight change when immersed in a sealed container containing 250 g of toluene.

  The pressure-sensitive adhesive of the present invention is less likely to be charged with static electricity generated in each process, and is excellent in adhesiveness between the optical laminate and the glass substrate even under high temperature and high humidity conditions. In addition, foaming and peeling do not occur during this period, and the light leakage phenomenon caused by the shrinkage of the optical film can be suppressed. Therefore, a liquid crystal display panel having excellent durability can be obtained, which is very useful.

Claims (7)

A pressure-sensitive adhesive composition comprising an acrylic resin (A), an ionic compound (B) having a bis (fluorosulfonyl) imide anion, and an oxyalkylene group-containing compound (C), the oxyalkylene The pressure-sensitive adhesive composition, wherein the group-containing compound (C) is a compound represented by the following general formula (1) that contains an oxyalkylene structure and does not contain a hydroxyl group at the molecular chain terminal.

Adhesive pressure sensitive adhesive composition of claim 1 Symbol mounting, characterized by comprising cross-linked. Adhesive composition contains an unsaturated group-containing compound (D) and the polymerization initiator (E), the pressure-sensitive adhesive of claim 2, wherein the composed is crosslinked by active energy ray and / or heat. The pressure-sensitive adhesive composition according to claim 2 or 3 , wherein the pressure-sensitive adhesive composition contains a crosslinking agent (F) and is crosslinked by the crosslinking agent (F). An adhesive for optical members, comprising the adhesive according to any one of claims 2 to 4 . 6. The optical member pressure-sensitive adhesive according to claim 5, wherein the optical member is a polarizing plate. An optical member with an adhesive layer, wherein the adhesive for an optical member according to claim 5 or 6 is laminated on the optical member.