Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
  • C09J133/04—Homopolymers or copolymers of esters
  • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
  • C09J133/062—Copolymers with monomers not covered by C09J133/06
  • C09J133/066—Copolymers with monomers not covered by C09J133/06 containing -OH groups
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
  • C09J133/04—Homopolymers or copolymers of esters
  • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
  • C09J133/08—Homopolymers or copolymers of acrylic acid esters
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J7/00—Adhesives in the form of films or foils
  • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
  • C09J7/38—Pressure-sensitive adhesives [PSA]
  • C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
  • C09J7/385—Acrylic polymers
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
  • C09J9/02—Electrically-conducting adhesives
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J2301/00—Additional features of adhesives in the form of films or foils
  • C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
  • C09J2301/302—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C

Definitions

• the present invention relates to an antistatic pressure-sensitive adhesive and a protective film for an optical member that carries a pressure-sensitive adhesive layer formed from the antistatic pressure-sensitive adhesive. More specifically, the present invention relates to an adhesive suitable for a surface protective film for mechanically and electrically protecting an adherend surface for a predetermined period. More specifically, the pressure-sensitive adhesive of the present invention is suitably used for forming a surface protective pressure-sensitive adhesive film for optical parts such as liquid crystal panels, plasma displays, polarizing plates, and CRTs (CRTs).
• CRTs CRTs
• a transparent surface protective film such as polyethylene, polyester, or polypropylene is laminated via an adhesive layer.
• the method (1) includes a thermoplastic resin such as polyester or polyethylene, which is a raw material of the base film, and a resin compound such as an organic sulfonate group, metal powder, carbon black, or the like.
• a conductive substrate film is obtained by kneading and mixing a conductive filler. In this case, the transparency of the substrate film is lowered or the film is colored.
• the substrate film itself is required to be excellent in transparency and optically free from defects.
• the method (2) has various variations as shown below (for example, Patent Documents 1 to 3;
• a light-on surfactant such as a long-chain alkyl compound having a sulfonate group has a relatively low molecular weight
• a part of the antistatic agent migrates through the antistatic coating film.
• the method (3) is a method of imparting antistatic performance to a peeling interface where static electricity is generated.
• There is a method of forming an adhesive layer with an adhesive Patent Document 6).
• examples of the antistatic agent used include various surfactants and conductive powders such as carbon black.
• the surfactant generally tends to concentrate on the surface of the pressure-sensitive adhesive layer, i.e., the bonding interface with the adherend. Very susceptible to That is, water reduces the cohesive force of the pressure-sensitive adhesive layer, and part of the pressure-sensitive adhesive layer tends to remain on the adherend (so-called “glue residue”) when the surface protective pressure-sensitive adhesive film is peeled off.
• a conductive pressure-sensitive adhesive containing conductive powder such as carbon black
• Patent Document 7 (For example, Patent Document 7).
• Patent Document 7 is for an electrode pad that is used by being attached to a living body although it relates to a conductive adhesive
• the conductive adhesive described in Patent Document 7 is a surface protective adhesive film. For use, it was hard to use.
• the curing agent is used for the purpose of ensuring the pot life of the pressure-sensitive adhesive. It is a common usage form that is separated and blended with a curing agent just before using the adhesive.
• main agent the pressure-sensitive adhesive solution containing no curing agent.
• the pressure-sensitive adhesive containing the main agent and the curing agent is applied to various substrates such as a plastic film, dried and cured to form a pressure-sensitive adhesive layer, and then adhered to the adherend.
• substrates such as a plastic film
• the decomposition of the alkylene oxide chain proceeds as time elapses after the main agent and the curing agent react and the adhesive layer is formed. .
• the conductivity decreased.
• Patent Document 1 Japanese Patent Laid-Open No. 7-26223
• Patent Document 2 Japanese Patent Laid-Open No. 11-256116
• Patent Document 3 Japanese Patent Laid-Open No. 2001-219520
• Patent Document 4 Japanese Patent Laid-Open No. 2002-060707
• Patent Document 5 JP 2002-275296 A
• Patent Document 6 JP-A-1-253482
• Patent Document 7 Japanese Patent No. 2718519
• the object of the present invention is to be suitable as a pressure-sensitive adhesive for surface protective adhesive films of optical members such as various displays and polarizing plates, with good storage stability of the main agent, excellent transparency, and mostly coloring.
• An object of the present invention is to provide an antistatic pressure-sensitive adhesive that has excellent re-peelability and has little peeling charge upon peeling.
• an antistatic pressure-sensitive adhesive having good storage stability of the main agent and appropriate conductivity was obtained, and the present invention was completed.
• the present invention contains an acrylic copolymer (A) having a hydroxyl group and an alkylene oxide chain in the side chain, an ionic compound (B), a curing agent (C), and an antioxidant (D). And an antistatic acrylic pressure-sensitive adhesive characterized by
• a preferable aspect of the acrylic pressure-sensitive adhesive of the present invention is that the alkylene oxide has a caloric number power of ⁇ 16.
• the alkylene oxide chain is an ethylene oxide chain.
• the antioxidant (D) is
• the acrylic copolymer (A) has a weight average molecular weight of 50,000 to 1,000,000.
• the ionic compound (B) is an ionic compound (
• B) is liquid or solid at room temperature.
• the ionic compound (B) is an alkali metal inorganic salt or alkali metal organic salt.
• the acrylic pressure-sensitive adhesive further contains an acrylic copolymer (E) having no alkylene oxide chain.
• the ionic compound (A) and (E) are combined with respect to a total of 100 parts by weight of the ionic copolymer (A) and (E). Contains 0.1 to 50 parts by weight of B).
• the acrylic copolymer (A) is obtained by subjecting a monomer having an alkylene oxide chain to copolymerization.
• the monomer having an alkylene oxide chain is 1 to 60% by weight.
• an acrylic copolymer is used.
• the alkylene oxide monomers having a chain is 1 to 60 weight 0/0.
• a curing agent (C) force trifunctional isocyanate compound and Z or polyfunctional epoxy compound are used.
• the present invention relates to a protective film for an optical member, characterized in that a pressure-sensitive adhesive layer formed from the above antistatic acrylic pressure-sensitive adhesive is laminated on at least one surface of a plastic film substrate.
• an antistatic pressure-sensitive adhesive having good storage stability of the main agent, an appropriate surface resistance, and excellent transparency and removability can be obtained.
• FIG. 1 An antistatic pressure-sensitive adhesive film according to the present invention comprising a PET film substrate and an antistatic acrylic pressure-sensitive adhesive layer carried on one surface of the anti-static acrylic pressure-sensitive adhesive layer by means of an antistatic acrylic pressure-sensitive adhesive layer. It is typical sectional drawing which shows the state stuck on.
• FIG. 2 shows a state in which an antistatic pressure-sensitive adhesive film according to the present invention in which an antistatic acrylic pressure-sensitive adhesive layer is provided on both sides of a PET film substrate is attached to a polarizing plate with one antistatic acrylic pressure-sensitive adhesive layer. It is typical sectional drawing.
• FIG. 3 An antistatic adhesive film according to the present invention in which an antistatic coating agent layer is provided on one surface of a PET film substrate and an antistatic acrylic adhesive layer is further supported thereon is used as the antistatic acrylic film.
• FIG. 5 is a schematic cross-sectional view showing a state where the adhesive layer is attached to the polarizing plate 3.
• FIG. 4 An antistatic adhesive film according to the present invention comprising an antistatic acrylic adhesive layer provided on one surface of a PET film substrate and an antistatic coating agent layer provided on the opposite surface of the antistatic adhesive film according to the present invention.
• FIG. 5 is a schematic cross-sectional view showing a state of being attached to the polarizing plate 3 with an acrylic pressure-sensitive adhesive layer.
• the acrylic copolymer (A) used in the present invention has a hydroxyl group and an alkylene oxide chain.
• other acrylate monomers (a3) copolymerizable with these ie acrylic monomers (a3) having both hydroxyl groups and alkylene oxide chains and acrylic monomers (a3)) can do.
• the acrylic monomer (al) having a hydroxyl group used in the present invention is an acrylic monomer (al) having a hydroxyl group but having no alkylene oxide chain.
• the purpose of using the acrylic monomer (al) having a hydroxyl group is to ensure the removability while ensuring the adhesive force to the adherend. More specifically, a crosslinked structure is formed by utilizing a reaction between a curing agent (C), such as an isocyanate curing agent, which will be described later used in forming the pressure-sensitive adhesive layer, and these hydroxyl groups, and as described later.
• a curing agent (C) such as an isocyanate curing agent, which will be described later used in forming the pressure-sensitive adhesive layer, and these hydroxyl groups, and as described later.
• the acrylic monomer (al) having a hydroxyl group is preferably 1 to 30% by weight. More preferably, it is 3 to 10% by weight.
• the acrylic copolymer (A) and the acrylic copolymer (E) are used in combination, the acrylic monomer having a hydroxyl group is assumed when the total monomer constituting (A) and (E) is 100% by weight.
• the system monomer (al) is preferably 1 to 30% by weight. More preferably, 3-10 weight %.
• the acrylic monomer having a hydroxyl group (al) is less than 1% by weight, the degree of cross-linking and cohesion as the pressure-sensitive adhesive layer is insufficient, the adhesive strength becomes too large, and adhesive residue is generated. Since it is easy to do, it is not preferable. If it exceeds 30% by weight, the degree of crosslinking becomes so high that the adhesiveness becomes poor, which is preferable.
• Examples of the acrylic monomer (a2) having an alkylene oxide chain used in the present invention include a monomer having an ethylene oxide chain, a monomer having a propylene oxide chain, and a monomer having both.
• the number of added moles of the alkylene oxide chain that is, the number of repeating units, 3 to 20 is preferable, 4 to 16 is more preferable, and 6 to 12 is more preferable.
• the number of added moles of the alkylene oxide chain is increased, handling during polymerization tends to be complicated, and the crystallinity of the copolymer obtained as a result of the polymerization tends to increase, and the formed pressure-sensitive adhesive layer tends to become hard.
• the added mole number of the alkylene oxide chain becomes small, it is necessary to use a large amount of the monomer (a2) in order to obtain the desired conductivity. In such a case, there is a tendency to become gely during polymerization due to the influence of the bifunctional monomer that is produced as a by-product in the production process of the monomer (a2) and contained as an impurity in the monomer (a2).
• Monomers having an ethylene oxide chain include alkoxypolyethylene glycol (meth) acrylate and polyethylene glycol (meth) acrylate, such as methoxy polyethylene glycol (meth) acrylate, ethoxy polyethylene glycol (meth) acrylate, etc. Is mentioned.
• Examples of monomers having a propylene oxide chain include alkoxy polypropylene glycol (meth) acrylates such as methoxy polypropylene glycol (meth) acrylate and ethoxy polypropylene glycol (meth) acrylate, and polypropylene glycol (meth) aterrata ⁇ . Monkey.
• a monomer having an ethylene oxide chain is preferred in consideration of compatibility with the later-described ionic compound (B).
• the alkoxy group in which the hydroxyl group at the end of the alkylene oxide chain is blocked with an alkyl group from the viewpoint of not inhibiting the reactivity between the isocyanate-based crosslinking agent and the hydroxyl group derived from the monomer (al) in the main agent.
• the acrylic monomer (a2) having an alkylene oxide chain used in the present invention methoxy polyethylene glycol (meth) acrylate and ethoxy polyethylene glycol (meth) acrylate are particularly preferable.
• the purpose of using the acrylic monomer (a2) having an alkylene oxide chain in the present invention is to form a complex with the ionic compound (B) and the alkylene oxide chain to develop conductivity. Therefore, the role of the alkylene oxide chain is very large, and it also serves as a transfer medium for the ionic compound (B), which merely provides a field for complex formation. In other words, the conductivity in the present invention varies greatly depending on the amount of the ionic compound (B) and the content of the monomer (a2) having an alkylene oxide chain.
• the total amount of monomers constituting the acrylic copolymer (A) is 100% by weight.
• the acrylic monomer (a2) having an alkylene oxide chain is preferably 1 to 60% by weight. More preferably, it is 5-50 weight%, and it is still more preferable that it is 8-40 weight%.
• the acrylic copolymer (A) and the acrylic copolymer (E) are used in combination, the alkylene oxide chain is changed when the total monomers constituting (A) and (E) are 100% by weight.
• the acrylic monomer (a2) is preferably 1 to 60% by weight. More preferably, it is 5-50 weight%, and it is still more preferable that it is 8-40 weight%.
• the amount of the acrylic monomer ( a2 ) having an alkylene oxide chain is small, the antistatic effect tends to be small.
• the amount is large, the crystallinity is high, and the high-speed peelability and antistatic property tend to be poor.
• the monomer (a3) copolymerizable with the acrylic monomer used in the present invention methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl ( (Meth) acrylate, pentyl (meth) acrylate, 2-ethyl hexyl (meth) acrylate, heptyl (meth) acrylate, hexyl (meth) acrylate, octyl (meth) acrylate, nor (meta ) Atalylate, Decyl (meth) Atalylate, Undecyl (meth) Atalylate, Dodecyl (Meth) Atylate, Tridecyl (Meth) Atylate, Tetradecyl (Meth) Atylate, Pentadecyl (Meth) Atarylate, Hexadecyl (Meta ) Atalylate, hept
• the acrylic monomer (a3) having a carbon number of ⁇ 12 it is preferable to subject the acrylic monomer (a3) having a carbon number of ⁇ 12 to copolymerization from the viewpoint of ensuring the adhesive properties. More preferred are butyl (meth) acrylate and 2-ethylhexyl (meth) acrylate.
• the acrylic copolymer (A) obtained by copolymerizing the acrylic monomer (al) having a hydroxyl group, the acrylic monomer (a2) having an alkylene oxide chain, and other monomers (a3), etc.
• the weight average molecular weight (Mw) is preferably from 50,000 to 1,000,000, more preferably from 50,000 to 200,000, a low molecular weight acrylic copolymer (A1).
• the pressure-sensitive adhesive for the protective film for an optical member is required to have an antistatic function, removability and transparency. Therefore, from the viewpoint of the antistatic function, it is preferable that the talyl copolymer (A) contains more alkylene oxide chains.
• optical members are very thin and fragile, while others are relatively strong.
• the protective film and the adhesive are required. The magnitude of the peel force applied is different.
• the peeling force is preferably 200 gZ25 mm or less so as not to damage the adherend when the protective film is peeled off after the sticking. More preferably, it is 100 gZ25 mm or less.
• the peel force can be allowed to be about 1000 gZ25 mm.
• the peel strength of the pressure sensitive adhesive is greatly influenced by the cohesive strength of the main component itself constituting the pressure sensitive adhesive and the state of crosslinking between the main component and the curing agent (C) described later.
• the peeling force can be reduced by using a large amount of the curing agent (C) relative to the main component.
• increasing the molecular weight of the main component increases the cohesion of the main component itself. can do.
• the curing agent (C) is used with respect to 100 parts by weight of the main component, that is, the acrylic copolymer (A). Is preferably used in an amount of 1 to 30 parts by weight, more preferably 2 to 20 parts by weight, and even more preferably 3 to 15 parts by weight. From the viewpoint of low peel strength, it is preferable that the curing agent (C) is large. However, if the amount is too large, the cross-linking becomes excessive, and it cannot be peeled off by sliding force.
• the acrylic monomer (a2) having an alkylene oxide chain used in the present invention can generally be easily copolymerized with other acrylic monomers (al) and (a3). Is big. Accordingly, if the viewpoint of improving conductivity is to increase the content of alkylene oxide chains, the molecular weight of the resulting acrylic copolymer (A) tends to decrease. When the molecular weight decreases, the cohesive force of the acrylic copolymer (A) itself tends to decrease, and the adhesive tends to remain on the adherend during peeling.
• a larger amount of the acrylic monomer (a2) having an alkylene oxide chain is copolymerized as the acrylate copolymer (A). It is preferable to use a low molecular weight acrylic copolymer (A1) having a weight average molecular weight (Mw) of 50,000 to 200,000.
• a high molecular weight acrylic copolymer (A2) having a weight average molecular weight (Mw) of 200,000 to 1,000,000 may be used as the acrylic copolymer (A). it can.
• Mw weight average molecular weight
• multistage polymerization refers to an operation in which a monomer is divided into a plurality of parts and used for polymerization. For example, when all monomers are charged in a reaction vessel and polymerized, or when no monomer is charged in the reaction vessel and all monomers are added dropwise to polymerize, both steps This is a two-stage polymerization in which a part of the monomer is charged in a reaction vessel and polymerized while dropping the remaining monomers. Further, when the remaining monomer is dropped and polymerized in two stages, this is a three-stage polymerization.
• Any of these polymerization methods can be selected for the purpose of adjusting the molecular weight of the resulting polymer.
• a monomer other than (a2) is used with little or no use of an acrylic monomer (a2) having an alkylene oxide chain for copolymerization at the initial stage of polymerization (reaction vessel). After the polymerization is progressed to the extent that it is a main component, the molecular weight of the acrylic copolymer (A2) is increased by subjecting all or most of the acrylic monomer (a2) having an alkylene oxide chain to polymerization. ) Can be obtained.
• a polymerization initiator can be further used when the main amount of the acryl-based monomer (a2) having an alkylene oxide chain is polymerized.
• the high molecular weight acrylic copolymer (A2) has a larger cohesive force than the low molecular weight acrylic copolymer (A 1), and therefore the amount of the curing agent (C) is reduced.
• the peel force is 100 gZ25 mm or less, preferably 50 gZ25 mm or less, it is preferable to form a dense cross-linked structure in the pressure-sensitive adhesive layer.
• the curing agent (C) should be used in an amount of about 1 to 30 parts by weight with respect to 100 parts by weight of the high molecular weight acrylic copolymer (A2) as in the case of the low molecular weight acrylic copolymer (A1). I like it.
• an acrylic copolymer (E) having no alkylene oxide chain can be used in combination, and an alkylene oxide chain having a weight average molecular weight (Mw) of 200,000 to 1,000,000 is used. Do not have! /, High molecular weight acrylic copolymer (E1) with weight average molecular weight ( Mw) It is also one of the embodiments of the present invention to use together with a low molecular weight acrylic copolymer (A1) having an alkylene oxide chain of 10,000 to 200,000.
• the low molecular weight acrylic copolymer (A1) is excellent in conductivity in many cases, but because of its low cohesive force, it has the power to suppress and prevent adhesive residue and a large amount of curing agent (C). Must be used.
• the high molecular weight acrylic copolymer (E1) in combination with such a low molecular weight acrylic copolymer (A1), the amount of the curing agent (C) used can be reduced.
• the curing agent (C) should be used in an amount of 0.1 to 20 parts by weight with respect to a total of 100 parts by weight of the low molecular weight acrylic copolymer (A1) and the high molecular weight acrylic copolymer ( ⁇ 1).
• it can be used in an amount of 0.5 to 10 parts by weight.
• various levels of electrification can be achieved by reducing the curing agent (C) while using the high molecular weight acrylic copolymer (E1) in this way. It can meet the requirements for prevention and removability.
• the curing agent (C) is used in an amount of 1 to 30 parts by weight based on 100 parts by weight of the total of the low molecular weight acrylic copolymer (A1) and the high molecular weight acrylic copolymer (E1), It is possible to obtain an adhesive with peel strength.
• the acrylic copolymer (E) having no alkylene oxide chain used in the present invention is an acrylic copolymer (E), except that an acrylic monomer having an alkylene oxide chain is not subjected to polymerization. It can be obtained as in A).
• the acrylic copolymer (A) and the acrylic copolymer (E) are used in combination, both are obtained after obtaining (A) and (E), respectively.
• the acrylic copolymer (A) may be obtained first, and the monomer constituting the acrylic copolymer (E) may be polymerized in the presence of the (A).
• a copolymer (E) is obtained, and the monomer constituting the acrylic copolymer (A) may be polymerized in the presence of the (E)! /.
• Examples of the ionic compound (B) used in the present invention include any ionic compounds that are liquid or solid at room temperature.
• room temperature means 25 ° C.
• Examples of the ionic compound (B) used in the method include inorganic salts of alkali metals or organic salts of alkali metals.
• so-called surfactants and other salts such as salt-ammonium, salt-aluminum, copper chloride, ferrous chloride, ferric chloride, ammonium sulfate and the like can be mentioned. These may be used singly or in combination, and alkali metal salts, liquid ionic compounds, and solid ionic compounds are preferred, and alkali metal salts and liquid ionic compounds are more preferred.
• alkali metal salt used in the present invention examples include metal salts having lithium, sodium, and potassium strength, and are composed of a cation moiety comprising Li +, Na +, K + and various key-on moieties. Depending on the type of cation part, it can be divided into inorganic salts and organic salts.
• Inorganic salts of alkali metals include sodium chloride, potassium salt, lithium chloride, lithium perchlorate (LiCIO), potassium chlorate, potassium nitrate, sodium nitrate, sodium carbonate.
• sodium chloride sodium, potassium potassium salt, lithium perchlorate and the like are preferable.
• alkali metal organic salts include sodium acetate, sodium alginate, sodium lignate sulfonate, sodium toluenesulfonate, LiCF SO, Li (CF SO) N, Li (
• Fluorine-containing lithium imide salts such as N, Li (C F SO) IN, especially (perfluoroalkyl)
• Preferable is a sulfonyl) imidolithium salt.
• the liquid ionic compound that can be used as the ionic compound (B) is a compound that exhibits liquid properties at room temperature, and is composed of a cation component and a cation component. ing.
• cation component of the ionic compound (B) of the present invention pyridinium cation, piperidium cation, pyrrolidinium cation, cation having pyrroline skeleton, cation having pyrrole skeleton, imidazolium cation, tetrahydropyrimidium Cation, dihydropyrimidinium cation, pyrazolium cation, virazolinium cation, tetraalkylammonium cation, trialkylsulfonium cation, tetraalkylphosphine Examples include home cations.
• the on-component is not particularly limited as long as it satisfies that it becomes a liquid ionic compounds, e.g., Cl _, Br ", ⁇ , A1C1-, Al CI "
• N N_, C F SO _, (C F SO) N_, C F COO ", (CF SO) (CF CO) N— etc.
• a cation component containing a fluorine atom is preferably used because an ionic compound having a low melting point can be obtained.
• liquid ionic compound used in the present invention are appropriately selected from the combination of the cation component and the cation component, and include, for example, 1 butyl pyridinium tetrafunoleoloborate, 1-Butylpyri-hexahexoleophthalate phosphate, 1-Butyl- 3 Methylpyridi-mu-tetrafluoroborate, 1-Butyl-3 Methylpyridi-mu-trifluoromethanesulfonate, 1-Butyl-3-methylpyridi-umbis (trifluoromethanesulfo- ) Imide, 1-butyl-3-methylpyridumumbis (pentafluoroethanesulfol) imide, 1-hexylpyridyl-tetrafluoroborate, 2-methyl-1-pyrrolinetetrafluoroborate, 1-ethyl 2-phenolindole Tetrafluoroborate,
• the solid ionic compound that can be used as the ionic compound (B) in the present invention is a combination of the force thione component and the cation component and exhibits a solid property at room temperature.
• examples of the surfactant that can be used as the ionic compound (B) include a cationic surfactant and an anionic surfactant.
• Examples of cationic surfactants include alkyl trimethyl ammonium salts, acylamidopropyl trimethyl ammonium methosulfate, alkyl benzyl methyl ammonium salts, choline chloride, polydimethyl (Meth) acrylate copolymer having a quaternary ammonium group such as aminoethyl methacrylate, styrene copolymer having a quaternary ammonium group such as polybutenyl trimethyl ammonium chloride, And diarylamine copolymers having a quaternary ammonium group such as polydiaryldimethylammonium chloride. These compounds can be used alone or in combination of two or more.
• anionic surfactant examples include alkyl sulfonate, alkyl benzene sulfonate, alkyl sulfate ester salt, alkyl ethoxy sulfate ester salt, alkyl phosphate ester salt, and sulfonate group-containing styrene copolymer. Is mentioned. These compounds may be used alone or in admixture of two or more.
• the content of the ionic compound (B) is 100 parts by weight of the acrylic copolymer (A), or when the acrylic copolymer (E) is used in combination,
• the total content is preferably 100 to 50 parts by weight with respect to 100 parts by weight. More preferably 1-30 parts by weight.
• the 0.1 If less than 1 part by weight, sufficient ionic conductivity cannot be obtained, and even if it contains more than 50 parts by weight of ionic compound (B), almost no improvement in conductivity can be expected, and the adhesive properties are further reduced. Also, it is not preferable because the coating film is likely to be whitened due to a decrease in compatibility with the resin.
• the stability over time of the pressure-sensitive adhesive film using the antistatic acrylic pressure-sensitive adhesive includes the amount of the ionic compound (B) and the acrylic copolymer (A).
• the amount of alkylene oxide chain greatly affects.
• the amount of the alkylene oxide chain contained in the pressure-sensitive adhesive layer is increased as much as possible, and a minimum amount of the ionic compound (B) capable of expressing the required conductivity is added.
• the curing agent (C) can be preferably used.
• the curing agent (C) of the present invention preferably two or more functional groups capable of reacting with a functional group such as a hydroxyl group contained in the acrylic copolymers (A) and (E) are contained in one molecule.
• a functional group such as a hydroxyl group contained in the acrylic copolymers (A) and (E)
• a known trifunctional isocyanate compound or a known polyfunctional epoxy compound can be suitably used. These can also be used in combination.
• a known trifunctional isocyanate compound a known diisocyanate compound is modified with a three-functional polyol component, so that a so-called adduct, diisocyanate compound is water and A reacted burette, diisocyanate compound, or a trimer (isocyanurate) having an isocyanurate ring that also forms a molecular force can be used.
• diisocyanate compounds include aromatic diisocyanates, aliphatic diisocyanates, araliphatic diisocyanates, alicyclic diisocyanates, and the like.
• Aromatic diisocyanates include 1,3-phenolic diisocyanate, 4, 4, Ninoresiocyanate, 1,4 Phenylene Diisocyanate, 4, 4, Di-Dimethane Diisocyanate, 2, 4 Tolylene Diisocyanate, 2, 6 Tolylene Diisocyanate, 4, 4, One Toluidine Examples thereof include isocyanate, di-cidin diisocyanate, 4,4′-diphenylenoyl monoterdiisocyanate, and the like.
• Aliphatic diisocyanates include trimethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, pentamethylene diisocyanate, 1,2-propylene diisocyanate, 2, 3 Examples include butylene diisocyanate, 1,3 butylene diisocyanate, dodecamethylene diisocyanate, and 2,4,4 trimethylhexamethylene diisocyanate.
• the aromatic aliphatic diisocyanate includes ⁇ , ⁇ , monodiisocyanate, 1,3 dimethylbenzene, ⁇ , ⁇ , monodiisocyanate, 1,4 dimethylbenzene, ⁇ , ⁇ , monodiisocyanate, 1,4-jetylbenzene. 1, 4-tetramethylxylylene diisocyanate, 1,3-tetramethylxylylene diisocyanate, and the like.
• the alicyclic diisocyanates include 3-isocyanate methyl-1,3,5,5 trimethylcyclohexenoylisocyanate, 1,3 cyclopentane diisocyanate, 1,3 cyclohexanediiso Cyanate, 1,4-cyclohexanediisocyanate, methyl-2,4 cyclohexanediisocyanate, methyl-2,6 cyclohexanediisocyanate, 4,4, -methylenebis (cyclohexyliso Cyanate), 1,4 bis (isocyanate methyl) cyclohexane, 1,4 bis (isocyanate methyl) cyclohexane, and the like.
• the diisocyanate compounds used in the present invention include 4,4'-diphenylmethane diisocyanate, hexamethylene diisocyanate, 3-isocyanate methyl-3, 5, 5-trimethyl. It is preferable to use cyclohexyl isocyanate (also referred to as “isophorone diisocyanate”).
• the known polyfunctional epoxy compound is not particularly limited as long as it is a compound having a plurality of epoxy groups in the molecule.
• Specific examples of the polyfunctional epoxy compound include ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, 1,6 hexanediol diglycidyl ether, and bisphenol.
• Enol ⁇ -epoxychlorohydrin type epoxy resin N, N, N, N, monotetraglycidyl 1 m-xylenediamine, 1,3-bis (N, N-diglycidylaminomethyl) cyclohexane, N, N-diglycidyl dilin, N, N-diglycidyl toluidine and the like can be mentioned.
• a trifunctional isocyanate compound and a polyfunctional epoxy compound can be used alone or in combination.
• a polyfunctional epoxy compound when heat resistance is required, which preferably uses a trifunctional isocyanate compound.
• the curing agent (C) should be used with respect to 100 parts by weight of the acrylic copolymer (A). It is more preferable to use 2 to 20 parts by weight, and more preferable to use 3 to 15 parts by weight.
• the acrylic copolymer (A) contains acrylic acid or methacrylic acid in order to act as a crosslinking agent more effectively.
• the content is preferably 0.5 to 5% by weight in the total acrylic monomer. If it is less than 5%, it does not sufficiently act as a crosslinking agent, and if it exceeds 5%, the pot life after the addition of the curing agent (C) tends to be short.
• One of the purposes is to suppress the increase in viscosity of the main agent over time.
• Another object is to prevent the conductivity of the pressure-sensitive adhesive layer after the reaction between the main agent and the curing agent from decreasing with time.
• the acrylic copolymer (A) of the present invention a monomer having many alkylene oxide chains is used.
• the acrylic copolymer (A) is not resistant to heat.
• a stable ether bond portion is decomposed to generate a radical.
• the residual monomers remaining in the acrylic copolymer (A) and acrylic copolymer (E) are polymerized over time, resulting in a thickening of the main agent. End up.
• the antioxidant (D) decomposition of the ether bond of the alkylene oxide chain can be suppressed, and an increase in the viscosity of the main agent over time can be suppressed.
• the use of the antioxidant (D) enables alkylene oxide after the reaction between the main agent and the curing agent. This suppresses the decomposition of the ether bond of the oxide chain and suppresses the deterioration of the conductivity of the adhesive layer over time.
• the amount of the antioxidation agent (D) used is preferably 0.01-10.0 parts by weight, more preferably 0.1-0.1 parts by weight per 100 parts by weight of the acrylic copolymer (A). 3. 0 parts by weight. If the amount is less than 0.01 parts by weight, the effect of suppressing the viscosity increase of the main agent is insufficient. If the amount is more than 10.0 parts by weight, contamination of the adherend may be caused by the antioxidant component.
• anti-oxidation agent (D) used in the present invention a known anti-oxidation agent can be used.
• antioxidant (D) examples include phenolic acid antioxidants, phosphite acid antioxidants, thioether acid antioxidants, and the like. These can be used alone, but in some cases, they can also be used in combination. In the present invention, phenolic acid antioxidants are preferred. Particularly, hindered phenol acid antioxidants are also preferable in terms of heat resistance, weather resistance, and compatibility.
• phenolic antioxidants include compounds having the following CAS numbers. 2767 6—62—6, 1843—03—4, 85—60—9, 2082—79—3, 6683—19—8, 3644
• Examples of the phosphite-based anti-oxidation agent include compounds having the following CAS numbers. 5266
• the antistatic pressure-sensitive adhesive of the present invention can be used in combination with other resin, such as acrylic resin, polyester resin, amino resin, epoxy resin, and polyurethane resin, if necessary. .
• resin such as acrylic resin, polyester resin, amino resin, epoxy resin, and polyurethane resin, if necessary.
• tackifiers such as talc, calcium carbonate, titanium oxide, etc. You may mix
• blend additives such as a filler, a coloring agent, a ultraviolet absorber, an antifoamer, and a light stabilizer.
• a pressure-sensitive adhesive sheet is obtained in which a pressure-sensitive adhesive layer formed from the pressure-sensitive adhesive and a substrate such as a plastic film, paper, cloth, or foam are laminated.
• the surface of the pressure-sensitive adhesive layer can be covered with a release sheet.
• the pressure-sensitive adhesive sheet can be obtained by applying or impregnating various types of base materials with a pressure-sensitive adhesive and drying and curing it. Alternatively, a pressure-sensitive adhesive is applied onto the release sheet, dried, and various substrates are laminated on the surface of the pressure-sensitive adhesive layer that is being formed, and the hydroxyl group in the pressure-sensitive adhesive and the isocyanate group in the curing agent (C), or It can also be obtained by advancing the reaction between the carboxyl group in the adhesive and the epoxy group in the curing agent (C).
• a surface protective pressure-sensitive adhesive film for an optical member can be suitably obtained.
• plastic film examples include a polychlorinated butyl film, a polyethylene film, a polyethylene terephthalate (PET) film, a polyurethane film, a nylon film, a treated polyolefin film, and an untreated polyolefin film.
• PET polyethylene terephthalate
• the antistatic pressure-sensitive adhesive of the present invention is preferably applied to a substrate or the like so as to have a thickness of about 2 to 200 m when dried and cured. If it is less than 2 m, the ionic conductivity becomes poor, and if it exceeds 200 m, it becomes difficult to produce and handle the adhesive sheet.
• FIG. 1 shows an antistatic pressure-sensitive adhesive film according to the present invention comprising a PET (polyethylene terephthalate) film substrate 1 and an antistatic acrylic pressure-sensitive adhesive layer 2 held on one surface thereof.
• FIG. 6 is a schematic cross-sectional view showing a state where the film is attached to the polarizing plate 3.
• Figure 2 shows a book with an antistatic acrylic adhesive layer 2 on both sides of a PET film substrate 1.
• 2 is a schematic cross-sectional view showing a state in which an antistatic pressure-sensitive adhesive film according to the invention is attached to a polarizing plate 3 with one antistatic acrylic pressure-sensitive adhesive layer 2.
• FIG. 1 is a schematic cross-sectional view showing a state in which an antistatic pressure-sensitive adhesive film according to the invention is attached to a polarizing plate 3 with one antistatic acrylic pressure-sensitive adhesive layer 2.
• FIG. 3 shows an antistatic pressure-sensitive adhesive film according to the present invention in which an antistatic coating agent layer 4 is provided on one surface of a PET film substrate 1 and an antistatic acrylic pressure-sensitive adhesive layer 2 is further supported thereon.
• FIG. 3 is a schematic cross-sectional view showing a state where the protective acrylic pressure-sensitive adhesive layer 2 is attached to the polarizing plate 3.
• FIG. 4 shows an antistatic pressure-sensitive adhesive film according to the present invention in which an antistatic acrylic pressure-sensitive adhesive layer 2 is provided on one surface of a PET film substrate 1 and an antistatic coating agent layer 4 is provided on the opposite surface.
• FIG. 3 is a schematic cross-sectional view showing a state where the protective acrylic pressure-sensitive adhesive layer 2 is attached to the polarizing plate 3.
• an antistatic coating agent layer should be provided as shown in FIGS. 3 and 4 in order to further reduce the peel charge amount. Is also possible.
• antistatic acrylic adhesive layers are provided on both sides of the base film, and one antistatic acrylic adhesive layer has functionalities.
• a film for example, a retardation film, an optical compensation film, a light diffusion film, an electromagnetic wave shielding film, etc.
• FIG. 1 Considering workability and production cost, the embodiment shown in FIG. 1 is most preferable.
• the antistatic agent used for forming the antistatic coating layer include metal fillers, quaternary ammonium salt derivatives, surfactants, and conductive resins.
• Examples of the metal filler include metal oxides such as tin oxide, zinc oxide, iron oxide and antimony oxide, metals such as carbon, silver and copper. In consideration of the transparency of the coating film, tin oxide, antimony oxide and the like are preferable.
• the antistatic coating agent layer preferably has a thickness of 0.1 ⁇ m to 50 ⁇ m as a coating film, more preferably 1 ⁇ m to 20 ⁇ m. If it is less than 0.1 m, the antistatic performance cannot be sufficiently exerted, and if it exceeds 50 m, there are problems in cost, coating properties, and the like.
• reaction kettle was 46% by weight of 2EHA [46 of 68% by weight of “68” in Table 1].
• the reaction kettle was 44% by weight of 2EHA, 50% by weight of 2HEA, the total amount of M40G, and ethyl acetate as a solvent.
• Add an appropriate amount of azobisisobutyl-tolyl as an initiator add the remaining monomer, ethyl acetate, and azobisisobutyl-tolyl in an appropriate amount, add dropwise over about 1 hour, and then add about 80 ° C under nitrogen atmosphere. For 5 hours. After completion of the reaction, it was cooled and diluted with ethyl acetate.
• This reaction solution had a solid content of 41%, a viscosity of 1200 mPa's, and Mw (weight average molecular weight) of 350,000.
• An acrylic copolymer (A) having a monomer force with the composition ratio shown in Table 1 was obtained as follows. In other words, a stirrer, a reflux condenser, nitrogen inlet, thermometer, using a 4 Roff flask equipped with a dropping funnel, 35% by weight of 2EHA to the reaction kettle, 30 wt% of BA, 30 wt 0/0 of 2HEA, acetate as a solvent Echiru, Azobisuisopuchi port as initiator - qs tolyl charged, then 42 weight 2EHA 0/0, 40 weight 40 weight 0/0, 2HEA of BA 0/0, 30% by weight of M90G, acetic acid A solution prepared by adding a suitable amount of ethyl and azobisisobutyl-tolyl was added dropwise over about 1 hour and polymerized at about 80 ° C. for 1 hour in a nitrogen atmosphere.
• the reaction kettle was 40% by weight of 2EHA, 30% by weight of BA, 30% by weight of 2HEA, acetate Echiru, Azobisuisopuchi port as initiator - qs tolyl charged, then, 40 weight 46 weight 0/0, BA of 2EHA 0/0, 40 weight 2HEA 0/0, 20% by weight of M90G, acetic Echiru, A solution prepared by adding an appropriate amount of azobisisobutyl-tolyl was added dropwise over about 1 hour and polymerized at about 80 ° C. for 1 hour in a nitrogen atmosphere.
• a solution prepared by adding a suitable amount of the remaining monomers, ethyl acetate, toluene, and azobisisobuty-tolyl was added dropwise over about 1 hour and polymerized at about 80 ° C. for 5 hours in a nitrogen atmosphere. After completion of the reaction, the reaction mixture was cooled and diluted with toluene. This reaction solution had a solid content of 41%, a viscosity of 100 OmPa's, and Mw (weight average molecular weight) of 110,000.
• reaction kettle was 44% by weight of 2EHA, 50% by weight of BA, 50% by weight of 2HEA, 50% by weight, total amount of M40G, ethyl acetate as solvent, azobisisopropylonitrile as initiator,
• reaction kettle was 88% by weight of 2EHA, 50% by weight of 2HEA, ethyl acetate as solvent, initiator As azobis isopuchi mouth-tolyl
• a solution prepared by adding a suitable amount of the remaining monomers, ethyl acetate, toluene, and azobisisobuty-tolyl was added dropwise over about 1 hour and polymerized at about 80 ° C. for 5 hours in a nitrogen atmosphere. After completion of the reaction, the reaction mixture was cooled and diluted with toluene. This reaction solution had a solid content of 40%, a viscosity of 400 mPa's, and Mw (weight average molecular weight) of 105,000.
• This reaction solution had a solid content of 41%, a viscosity of 1700 mPa's, and Mw (weight average molecular weight) of 400,000.
• a monomer power having a composition ratio shown in Table 1 was formed, and no hydroxyl group was contained.
• An acrylic copolymer was obtained as follows.
• reaction kettle was 35% by weight of 2EHA, 30% by weight of BA, ethyl acetate as the solvent, start An appropriate amount of azobisisopetite-tolyl is added as an agent,
• AM9 OG Metoxypolyethyleneglycol acrylate (ethylene oxide 9 mo I)
• the obtained pressure-sensitive adhesive was coated on a release paper to a dry coating thickness of 20 m, dried at 100 ° C for 2 minutes, and then formed into a polyethylene terephthalate film (thickness 38 ⁇ m) ) And laminated for 2 days at room temperature in this state to obtain a test adhesive tape.
• the adhesive strength, surface resistance value, removability and transparency were evaluated according to the following methods. Furthermore, the storage stability of the main component of the adhesive was evaluated.
• the release paper of the test pressure-sensitive adhesive tape was peeled off, and the exposed pressure-sensitive adhesive layer was attached to a glass plate having a thickness of 2 mm at 23 ° C.-50% RH, and roll-bonded according to JIS Z-0237. After 24 hours, the peel strength (180 degree peel, tensile speed 3 OOmmZ; unit gZ25mm width) was measured with a shopper type peel tester.
• the release paper of the test pressure-sensitive adhesive tape was peeled off, and the surface resistance value of the exposed pressure-sensitive adhesive layer surface was measured using a surface resistance measurement device (Mitsubishi Chemical Corporation) ( ⁇ Z port).
• the main component of the pressure-sensitive adhesive (among the blended components, a curing agent was added!) was placed in a sealed container, and the rate of increase in viscosity after one month was measured in an oven at 50 ° C. Viscosity increase rate is less than 10% ⁇
• Viscosity increase rate is 10% or more and less than 20% ⁇
• Viscosity increase rate is 20% or more and less than 50% ⁇
• Viscosity increase rate is 50% or more or gelation X
• a pressure-sensitive adhesive was obtained in the same manner as in Example 1 except that each acrylic resin obtained in Synthesis Examples 2, 3, and 5 was used, and lithium perchlorate was used in an amount of 5 g. evaluated.
• a pressure-sensitive adhesive was obtained in the same manner as in Example 1 except that the acrylic resin obtained in Synthesis Example 4 was used and lithium chloride was used in an amount of 3 g, and evaluation was performed in the same manner as in Example 1.
• a pressure-sensitive adhesive was obtained in the same manner as in Example 1 except that the acrylic resin obtained in Synthesis Example 7 was used and lithium perchlorate was used in an amount of lg, and evaluation was performed in the same manner as in Example 1.
• a pressure-sensitive adhesive was obtained in the same manner as in Example 1 except that 3 g of lithium perchlorate was used using the acrylic resin obtained in Synthesis Example 7, and evaluation was performed in the same manner as in Example 1.
• Example 2 Evaluation was performed in the same manner as in Example 1 except that the acrylic resin obtained in Synthesis Examples 5 and 7 was used, lithium perchlorate lg was used, and the test adhesive tape was obtained after 7 days at room temperature.
• Example 2 Evaluation was performed in the same manner as in Example 1 except that the acrylic resin obtained in Synthesis Example 7 was used, lithium perchlorate lg was used, and a test adhesive tape was obtained after 30 days at 50 ° C.
• CIL-314 (manufactured by Nippon Carlit Co., Ltd .: liquid ionic compound; pyridi-um derivative) was used in the same manner as in Example 8 except that 0.5 g was used. Obtained and evaluated in the same manner as in Example 1.
• a pressure-sensitive adhesive was obtained in the same manner as in Example 8, except that 0.3 g of lithium bis (pentafluoroethanesulfol) imide was used instead of lithium perchlorate lg. Rated 7.
• a pressure-sensitive adhesive was obtained in the same manner as in Example 8 except that Elegan C-114 (manufactured by Yuki Oil Co., Ltd .: Cationic surfactant) lg was used instead of lithium perchlorate lg.
• Example 1 It was evaluated in the same way. [0116] [Example 17]
• a pressure-sensitive adhesive was obtained in the same manner as in Example 8 except that 1 g of KS-1262 (manufactured by Kao Corporation: a-on surfactant) was used instead of lithium perchlorate lg. Evaluated.
• Elegan C-114 (0, manufactured by Yuki Yushi Co., Ltd .: Cationic surfactant) 0.9g and PEL-20A (Nihon Carlit, Inc .: lithium perchlorate Z polyester monopolyol ) was used in the same manner as in Example 8 except that 0.1 lg was used, and evaluated in the same manner as in Example 1.
• Adekastab HP-10 Adekastab HP-10 (Asahi Denka Co., Ltd .: Phosphite-based anti-oxidation agent) 0.3 g was used in the same manner as in Example 8 except that 0.3 g was used. An adhesive was obtained and evaluated in the same manner as in Example 1.
• Adekastab AO-80 Adhesive similar to Example 8 except that 0.2g of Adekastab AO-23 (Asahi Denka Co., Ltd .: thioether antioxidant) was used instead of 0.2g. And evaluated in the same manner as in Example 1.
• Example 8 “Adeka Stub AO-80” Instead of 0.2 g, Tinuvin T-123 (Cibas Specialty Chemicals Co., Ltd .: hindered amine acid / antioxidant) 0.2 g was used in the same manner as in Example 8, except that 0.2 g was used. An adhesive was obtained and evaluated in the same manner as in Example 1.
• a pressure-sensitive adhesive was obtained in the same manner as in Example 8 except that ILA2-2 (made by Guangei Chemical Co., Ltd .: solid ionic compound) lg was used instead of lithium perchlorate lg. It was evaluated in the same way. [0123] [Comparative Examples 1 and 4]
• a pressure-sensitive adhesive was obtained in the same manner as in Example 1 except that “AO-80” was used, and evaluated in the same manner as in Example 1.
• a pressure-sensitive adhesive was obtained in the same manner as in Example 1 except that the acrylic resin obtained in Synthesis Example 9 was used, lithium perchlorate was used in an amount of 5 g, and “ADK STAB AO-80” was used. Evaluation was conducted in the same manner as in Example 1.
• the acrylic resin solution obtained in Synthesis Example 10 was desolvated and then dissolved in acetylethylacetone, and 3% by weight of lithium perchlorate was added to the acryl resin solid content and dissolved. This uniform viscous liquid was cast on an aluminum foil and dried at 80 ° C. for about 2 days to completely evaporate the acetone.
• the obtained resin sheet was laminated on a polyethylene terephthalate film (thickness 38 ⁇ m) and evaluated in the same manner as in Example 1.
• Example 7 The test was carried out except that the acrylic resin obtained in Synthesis Example 7 was used, Adeka Stub AO-80 was not used, lithium perchlorate lg was used, and a test adhesive tape was obtained after 7 days at room temperature. A pressure-sensitive adhesive was obtained in the same manner as in Example 1, and evaluated in the same manner as in Example 1.
• Antistatic pressure-sensitive adhesive of the present invention as above: agent, storage stability of the base resin, the surface resistivity (conductivity Property), transparency and removability.
• the pressure-sensitive adhesive shown in Comparative Example 1 has no conductivity because it contains no alkylene oxide chain and ion compound. Since the pressure-sensitive adhesive shown in Comparative Example 2 does not have an alkylene oxide chain, the ionic compound does not dissolve and aggregates, resulting in poor transparency and surface resistance. As shown in Comparative Example 3, the pressure-sensitive adhesive does not contain a hydroxyl group-containing monomer, so that the crosslinking effect by the curing agent cannot be obtained, the removability is poor, and an antioxidant is further contained. The storage stability of the main agent was poor. The pressure-sensitive adhesive shown in Comparative Example 4 had poor conductivity because it did not contain ionic compounds, and further contained antioxidants, so the storage stability of the main agent was poor. Since the adhesive shown in Comparative Example 5 did not use any curing agent, the cohesive force was insufficient and the removability was poor.
• the acrylic copolymer (A) was further crosslinked with a hardener between the release paper and the polyethylene terephthalate film.
• the acrylic layer is not simply formed on the polyethylene terephthalate film and the curing agent is not used.Therefore, the cohesive force as an adhesive is insufficient and the removability is poor. became.
• the pressure-sensitive adhesives shown in Comparative Examples 7 and 8 did not contain an anti-oxidation agent, so the storage stability of the main agent was poor.
• the antioxidant is not contained, the surface resistance value of the adhesive layer after the reaction between the main agent and the curing agent also increases with the passage of time, so the antistatic performance is not stable.
• the antistatic pressure-sensitive adhesive of the present invention has good storage stability of the main agent, has an appropriate surface resistance value, and is excellent in transparency and removability.
• it is suitable for forming adhesive films for surface protection of optical parts such as liquid crystal panels, plasma displays, polarizing plates, and CRTs (CRTs). .

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