WO2015012526A1 - Adhesive composition - Google Patents

Abstract

The present invention relates to an adhesive composition and, more specifically, to an adhesive composition which: contains an ionic antistatic agent and an acryl-based copolymer containing an acrylate-based monomer having an amino alcohol group; accordingly, does not cause detachment, bubbling, peeling, and the like due to the surface migration of the antistatic agent and thus has excellent durability and antistatic properties; and can effectively inhibit the corrosion of a metal layer without separately containing a corrosion inhibitor ingredient.

Description

Pressure-sensitive adhesive composition

The present invention improves the compatibility between the antistatic agent and the acrylic copolymer containing no acid, thereby suppressing the bleed out of the antistatic agent, thereby improving the durability, antistatic property and corrosion resistance at the same time. It is about.

In general, a liquid crystal display device (LCD) is provided with a liquid crystal cell and a polarizing plate containing a liquid crystal, and an appropriate pressure-sensitive adhesive layer for bonding them is used. The pressure sensitive adhesive is often used an acrylic pressure sensitive adhesive based on an acrylic copolymer having excellent adhesiveness and transparency.

In the process of attaching the polarizing plate to the liquid crystal cell, peeling the release film from the pressure-sensitive adhesive layer generates static electricity. The generated static electricity affects the alignment of the liquid crystal and causes defects or flows between the liquid crystal cell and the adhesive due to electrostatic attraction. It causes contamination by foreign objects.

In order to improve this, an ionic antistatic agent is mixed and used in the pressure-sensitive adhesive composition, but a bleed out phenomenon that precipitates due to the surface migration of the ionic antistatic agent may cause lifting, bubbles, and peeling. In particular, this problem may be exacerbated when exposed to a high temperature or high temperature and high humidity environment.

In addition, the liquid crystal cell including a metal layer such as ITO is corroded by H ₂ O and O ₂ contained in the pressure-sensitive adhesive to form metal oxides, hydroxides, and other corrosive products. These may reduce the electrical or mechanical stability of the liquid crystal display, or may cause problems in securing visibility and reliability.

In order to improve the corrosiveness of metals, there is a tendency to exclude the use of hydrogen ion generating monomers (eg, monomers having a carboxyl group) which are essentially used for improving durability of the pressure-sensitive adhesive composition.

As mentioned above, the demand for the adhesive composition excellent in antistatic property and durability is increasing recently, without using a hydrogen ion generating monomer.

In this regard, a method of using an acryl-based copolymer having increased compatibility with an antistatic agent by introducing an amine group or a polyethylene glycol group while excluding a hydrogen ion generating monomer has been proposed (Korean Patent Publication No. 2009-132564, 1). 2011-136760).

However, this method is a situation that the effect is insufficient to improve the durability degradation due to the bleed out phenomenon.

The present invention is excellent in durability as well as antistatic properties because there is no phenomenon such as lifting, bubbles and peeling due to the surface migration of the antistatic agent, it does not contain a corrosion inhibitor component and can effectively suppress the corrosion of the metal layer The purpose is to provide.

In order to achieve the above object, the present invention provides an adhesive composition containing an acrylic copolymer prepared by copolymerizing monomers containing an acrylate monomer having an amino alcohol group and an ionic antistatic agent.

The acrylate monomer having an amino alcohol group may be an acrylate monomer having a β-hydroxydialkylamino group (hydroxycarbon containing a tertiary amino group in adjacent carbon).

The acrylate monomer having the amino alcohol group may include a compound represented by the following formula (1) or (2).

[Formula 1]

(Wherein R ₁ is an aliphatic hydrocarbon containing or not containing N or O hetero atoms having 1 to 12 carbon atoms, and R ₂ is an aliphatic compound containing or not containing N or O hetero atoms having 1 to 12 carbon atoms) hydrocarbons, and, R3 is an aliphatic hydrocarbon group with or without a hetero element of N or O with a carbon number of 1 ~ 6, R4 is hydrogen or a methyl group, and R ₁ and R ₂ is a carbon adjacent to each other 5 ring or It may form a 6 ring, the ring may contain a hetero element.)

[Formula 2]

(Wherein R ₁ is an aliphatic hydrocarbon containing or not containing N or O hetero atoms having 1 to 12 carbon atoms, and R ₂ is an aliphatic compound containing or not containing N or O hetero atoms having 1 to 12 carbon atoms) hydrocarbons, and, R3 is an aliphatic hydrocarbon group with or without a hetero element of N or O with a carbon number of 1 ~ 6, R4 is hydrogen or a methyl group, and R ₁ and R ₂ is a carbon adjacent to each other 5 ring or It may form a 6 ring, the ring may contain a hetero element.)

The acrylate-based monomer having an amino alcohol group may be at least one selected from the group consisting of the following Chemical Formulas 3 to 12.

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

The acrylic copolymer may be prepared by copolymerizing monomers including a (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms and an acrylate monomer having an amino alcohol group.

The acrylate monomer having an amino alcohol group may be included in an amount of 1 to 10 parts by weight based on 100 parts by weight of a (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms.

The ionic antistatic agent is a cation selected from the group consisting of alkali metal salts, ammonium salts, sulfonium salts and phosphonium salts; It may be an ionic salt consisting of an anion selected from the group consisting of fluorine-containing inorganic salts, fluorine-containing organic salts and iodine ions.

The pressure-sensitive adhesive composition may further contain a crosslinking agent.

The pressure-sensitive adhesive composition of the present invention does not have a phenomenon such as lifting, bubbles, and peeling due to the surface migration of the antistatic agent, which is excellent in durability and at the same time has an advantage of satisfying the antistatic property.

The pressure-sensitive adhesive composition of the present invention has an advantage of effectively suppressing corrosion of the metal layer without separately containing a corrosion inhibitor component.

Therefore, the pressure-sensitive adhesive composition is expected to have high utility for anti-static applications in the fields of plastic products, especially electrical / electronic devices, which tend to generate static electricity.

The present invention improves the compatibility between the antistatic agent and the acrylic copolymer containing no acid, thereby suppressing the bleed out of the antistatic agent, thereby improving the durability, antistatic property and corrosion resistance at the same time. It is about.

Hereinafter, the present invention will be described in detail.

The pressure-sensitive adhesive composition of the present invention contains an acrylic copolymer prepared by copolymerizing monomers containing an acrylate monomer having an amino alcohol group and an ionic antistatic agent.

Usually, an acrylic copolymer uses acrylic acid as a monomer in order to improve adhesiveness with glass and compatibility with an antistatic agent.

Specifically, the copolymer is introduced into the carboxylic acid by acrylic acid, and the introduced carboxylic acid forms a hydrogen bond in the copolymer to improve cohesion, and forms a hydrogen bond in silanol groups of the glass to improve adhesion. In addition, the carboxylic acid introduced into the copolymer inhibits the bleed out of the antistatic agent by polar interaction with the ionic antistatic agent, thereby improving durability.

However, in the case of a product including a metal layer such as ITO, corrosion is generated by H ₂ O and O ₂ contained in the pressure sensitive adhesive to form metal oxides, hydroxides, and other corrosive products. Required. Since the acid-free adhesive composition does not have a carboxyl group, there is a problem in that low adhesion, low aggregation, and stabilizing effect of the antistatic agent are insufficient, and durability is difficult to secure.

The pressure-sensitive adhesive composition according to the present invention contains an acrylate monomer having an amino alcohol group as a monomer for producing an acrylic copolymer. As such, when an acrylate monomer having an amino alcohol group is contained, the ionization tends to be large, as in carboxylic acids, and the interaction with glass is increased, thereby improving adhesion, and forming a hydrogen bond in the acrylic copolymer to improve cohesion. have. In addition, since the interaction with the antistatic agent is increased, the bleed-out of the antistatic agent is suppressed, so that the durability of the adhesive is greatly improved, and there is little concern about corrosion of ITO since no acid is generated.

The following structural formula illustrates the functional relationship between an acrylic acid monomer (structure 1) and an acrylate monomer (structure 2) having an aminoalcohol group of the present invention.

(Formula 1)

(Formula 2)

The amine in the molecule acts as a base to remove H ⁺ from the hydroxy group present in the adjacent position, and acts as a scavenger to immobilize the H ⁺ . That is, the pressure-sensitive adhesive composition containing it has the advantage of having a polar group having a carboxyl group, it is understood that the role of ensuring the ITO corrosion protection at the same time.

The acrylate monomer having an aminoalcohol group contained in the acrylic copolymer may be an acrylate monomer having a β-hydroxydialkylamino group (hydroxycarbon containing a tertiary amino group in adjacent carbon).

Preferably, the acrylate monomer having a β-hydroxydialkylamino group may include a compound represented by the following formula (1) or (2).

[Formula 1]

(Wherein R ₁ is an aliphatic hydrocarbon containing or not containing N or O hetero atoms having 1 to 12 carbon atoms, and R ₂ is an aliphatic compound containing or not containing N or O hetero atoms having 1 to 12 carbon atoms) hydrocarbons, and, R3 is an aliphatic hydrocarbon group with or without a hetero element of N or O with a carbon number of 1 ~ 6, R4 is hydrogen or a methyl group, and R ₁ and R ₂ is a carbon adjacent to each other 5 ring or It may form a 6 ring, the ring may contain a hetero element.)

[Formula 2]

(Wherein R ₁ is an aliphatic hydrocarbon containing or not containing N or O hetero atoms having 1 to 12 carbon atoms, and R ₂ is an aliphatic compound containing or not containing N or O hetero atoms having 1 to 12 carbon atoms) hydrocarbons, and, R3 is an aliphatic hydrocarbon group with or without a hetero element of N or O with a carbon number of 1 ~ 6, R4 is hydrogen or a methyl group, and R ₁ and R ₂ is a carbon adjacent to each other 5 ring or It may form a 6 ring, the ring may contain a hetero element.)

More preferably, the acrylate monomer having an amino alcohol group may be at least one selected from the group consisting of the following Chemical Formulas 3 to 12.

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

The acrylic copolymer of the present invention is preferably prepared by copolymerizing monomers including a (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms and an acrylate monomer having an amino alcohol group. In the present invention, (meth) acrylate means acrylate and methacrylate and the content is based on the solid content.

The (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms is n-butyl (meth) acrylate, 2-butyl (meth) acrylate, t-butyl (meth) acrylate, 2-ethylhexyl (meth) Acrylate, ethyl (meth) acrylate, methyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, pentyl (meth) acrylate, n-octyl (meth) acrylate, Isooctyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, lauryl (meth) acrylate, etc. are mentioned, Among these, n-butylacrylate and 2-ethylhexyl acrylate are mentioned. Or mixtures thereof. These can be used individually or in mixture of 2 or more types, respectively.

It is preferable that 1-10 weight part of said acrylate type monomer which has an amino alcohol group is contained with respect to 100 weight part of (meth) acrylate monomers which have a C1-C12 alkyl group, More preferably, it is 2-7 weight part good. When the content is less than 1 part by weight, the effect of improving durability may be insignificant, and when it exceeds 10 parts by weight, it may be difficult to secure other adhesive properties such as rework property.

The monomer for producing the acrylic copolymer of the present invention may further contain a polymerizable monomer having a crosslinkable functional group in addition to the acrylate monomer having the aminoalcohol group.

The polymerizable monomer having a crosslinkable functional group uses a component that does not generate hydrogen ions (H ⁺ ), which can impart cohesion or adhesive strength of the pressure-sensitive adhesive composition by chemical bonding to impart durability and cutting properties.

Examples of the polymerizable monomer having a crosslinkable functional group include a monomer having a hydroxy group, a monomer having an amide group, a monomer having a tertiary amine group, and the like, and these may be used alone or in combination of two or more thereof.

As a monomer which has a hydroxyl group, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 2-hydroxyethylene glycol (meth) acrylate, 2-hydroxypropylene glycol (meth) acrylate, hydroxyalkylene glycol having 2 to 4 carbon atoms of an alkylene group ( Meta) acrylate, 4-hydroxybutyl vinyl ether, 5-hydroxypentyl vinyl ether, 6-hydroxyhexyl vinyl ether, 7-hydroxyheptyl vinyl ether, 8-hydroxyoctyl vinyl ether, 9-hydroxynonyl Vinyl ether, 10-hydroxydecyl vinyl ether, etc. are mentioned, Among these, 4-hydroxybutyl vinyl ether is preferable.

Examples of the monomer having an amide group include (meth) acrylamide, N-isopropylacrylamide, N-tert-butylacrylamide, 3-hydroxypropyl (meth) acrylamide, 4-hydroxybutyl (meth) acrylamide, 6 -Hydroxyhexyl (meth) acrylamide, 8-hydroxyoctyl (meth) acrylamide, 2-hydroxyethylhexyl (meth) acrylamide, etc. are mentioned, and (meth) acrylamide is preferable among these. .

Monomers having a tertiary amine group include N, N- (dimethylamino) ethyl (meth) acrylate, N, N- (diethylamino) ethyl (meth) acrylate, and N, N- (dimethylamino) propyl ( Meth) acrylate etc. are mentioned.

It is preferable that the polymerizable monomer which has such a crosslinkable functional group is contained in 0.05-10 weight part with respect to 100 weight part of (meth) acrylate monomers which have a C1-C12 alkyl group, More preferably, it is 0.1-8 weight part good. If the content is less than 0.05 parts by weight, the cohesive force of the pressure-sensitive adhesive may be reduced, the durability may be lowered. If the content is more than 10 parts by weight, the adhesive strength is lowered by a high gel fraction may cause problems in durability.

In addition, the monomer for preparing the acrylic copolymer of the present invention may further contain other polymerizable monomers other than the above monomers in a range of not lowering the adhesive strength, for example, 10 parts by weight or less based on the total amount of monomers.

The production method of the copolymer is not particularly limited, and may be prepared using a method such as bulk polymerization, solution polymerization, emulsion polymerization or suspension polymerization, which are commonly used in the art, and solution polymerization is preferable. In addition, a solvent, a polymerization initiator, a chain transfer agent for molecular weight control, and the like, which are usually used in the polymerization, may be used.

The ionic antistatic agent is not particularly limited as long as it is an ionic salt composed of an anion and a cation and can impart ionic conductivity to the pressure-sensitive adhesive.

Specifically, a cation selected from the group consisting of alkali metal salts, ammonium salts, sulfonium salts and phosphonium salts; It may be an ionic salt consisting of an anion selected from the group consisting of fluorine-containing inorganic salts, fluorine-containing organic salts and iodine ions.

Such an ionic antistatic agent may contain 0.1 to 15 parts by weight, preferably 0.5 to 10 parts by weight, based on 100 parts by weight of the acrylic copolymer. If the content is less than 0.1 parts by weight may be insufficient antistatic properties and if it exceeds 10 parts by weight it may be difficult to secure durability.

The pressure-sensitive adhesive composition of the present invention may further contain a crosslinking agent.

A crosslinking agent can improve adhesiveness and durability, and can maintain the reliability and shape of an adhesive at high temperature.

The crosslinking agent may be an isocyanate type, an epoxy type, a melamine type, a peroxide type, a metal chelate type, an oxazoline type, or the like, and one or two or more kinds thereof may be used. Double isocyanate type or epoxy type is preferred.

The isocyanate type is tolylene diisocyanate, xylene diisocyanate, 2,4-diphenylmethane diisocyanate, 4,4-diphenylmethane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, tetramethyl xylene diisocyanate, naphthalenedi Diisocyanate compounds such as isocyanate; Diisocyanate obtained from 2 moles of an adduct obtained by reacting 3 moles of a diisocyanate compound with 1 mole of a polyhydric alcohol compound such as trimethylolpropane, an isocyanurate obtained by self-condensing 3 moles of the diisocyanate compound, and 3 moles of the diisocyanate compound The polyfunctional isocyanate compound etc. which contain three functional groups, such as the biuret body, triphenylmethane triisocyanate, and methylene bistriisocyanate which condensed the remaining 1 mol of diisocyanate to urea, are mentioned.

The epoxy-based ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, polypropylene glycol di Glycidyl ether, neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, polytetramethylene glycol diglycidyl ether, glycerol diglycidyl ether, glycerol triglycidyl ether, di Glycerol polyglycidyl ether, polyglycerol polyglycidyl ether, resorcin diglycidyl ether, 2,2-dibromoneopentyl glycol diglycidyl ether, trimethylolpropanetriglycidyl ether, pentaerythritol poly Glycidyl ether, sorbitol polyglycidyl ether, adipic acid diglycidyl ester, phthalic acid diglycidyl ester, tris (glycidyl) isocyanuric Tris (glycidoxyethyl) isocyanurate, 1,3-bis (N, N-glycidylaminomethyl) cyclohexane, N, N, N ', N'-tetraglycidyl-m- Xylylenediamine etc. are mentioned.

Examples of the melamine type include hexametholol melamine, hexamethoxymethylmelamine, hexabutoxymethylmelamine, and the like.

Such a crosslinking agent may be contained in an amount of 0.1 to 15 parts by weight, preferably 0.1 to 5 parts by weight, based on 100 parts by weight of the acrylic copolymer. If the content is less than 0.1 part by weight, the cohesive force may be reduced due to insufficient crosslinking degree, thereby impairing the adhesive durability and the cleavage property. If the content is more than 15 parts by weight, problems may occur in reducing residual stress due to excessive crosslinking reaction.

In addition to the above components, the pressure-sensitive adhesive composition is a silane coupling agent, tackifying resin, antioxidant, leveling agent, surface lubricant, dye, in order to adjust the adhesion, cohesion, viscosity, elastic modulus, glass transition temperature, etc. Additives, such as a pigment, an antifoamer, a filler, and a light stabilizer, can be further contained.

Such additives can be appropriately adjusted in a range not impairing the effects of the present invention.

In particular, the pressure-sensitive adhesive composition of the present invention can be used as a pressure-sensitive adhesive for polarizing plates and a surface protective film for bonding to liquid crystal cells. In addition, it can be used as a general commercial adhesive sheet product as well as a protective film, a reflective sheet, a structural adhesive sheet, a photographic adhesive sheet, a lane marking adhesive sheet, an optical adhesive product, an adhesive for electronic parts, and the like.

Hereinafter, preferred examples are provided to aid the understanding of the present invention, but the following examples are merely for exemplifying the present invention, and it will be apparent to those skilled in the art that various changes and modifications can be made within the scope and spirit of the present invention. It is natural that such variations and modifications fall within the scope of the appended claims.

Preparation Example: Acrylic Copolymer Preparation

<Manufacture example 1>

96 parts by weight of n-butyl acrylate (BA), 1 part by weight of 4-hydroxybutyl acrylate in a 1 L reactor equipped with a refrigeration system for reflux of nitrogen gas and easy temperature control

After the monomer mixture consisting of 3 parts by weight was added, 100 parts by weight of acetone was added as a solvent. After purging nitrogen gas for 1 hour to remove oxygen, it was maintained at 80 ℃. After homogenizing the mixture, 0.07 parts by weight of azobisisobutyronitrile (AIBN) was added as a reaction initiator, and reacted for 6 hours to prepare an acrylic copolymer having a weight average molecular weight of about 1.15 million.

<Manufacture example 2>

The same as in Preparation Example 1,

Instead of

An acrylic copolymer was prepared using.

<Manufacture example 3>

The same as in Preparation Example 1,

Instead of

An acrylic copolymer was prepared using.

<Manufacture example 4>

The same as in Preparation Example 1,

Instead of

An acrylic copolymer was prepared using.

Production Example 5

The same as in Preparation Example 1,

Instead of

An acrylic copolymer was prepared using.

<Manufacture example 6>

The same as in Preparation Example 1,

Instead of

An acrylic copolymer was prepared using.

<Manufacture example 7>

The same as in Preparation Example 1,

Instead of

An acrylic copolymer was prepared using.

<Manufacture example 8>

The same as in Preparation Example 1,

Instead of

An acrylic copolymer was prepared using.

<Manufacture example 9>

In the same manner as in Preparation Example 1, 98 parts by weight of n-butyl acrylate (BA), 1 part by weight of 4-hydroxybutyl acrylate,

An acrylic copolymer was prepared using a monomer mixture consisting of 1 part by weight.

Production Example 10

In the same manner as in Preparation Example 1, 93 parts by weight of n-butyl acrylate (BA), 1 part by weight of 4-hydroxybutyl acrylate,

An acrylic copolymer was prepared using a monomer mixture consisting of 6 parts by weight.

Production Example 11

In the same manner as in Preparation Example 1, 89 parts by weight of n-butyl acrylate (BA), 1 part by weight of 4-hydroxybutyl acrylate,

An acrylic copolymer was prepared using a monomer mixture composed of 10 parts by weight.

Production Example 12

In the same manner as in Preparation Example 1, 98.5 parts by weight of n-butyl acrylate (BA), 1 part by weight of 4-hydroxybutyl acrylate,

An acrylic copolymer was prepared using a monomer mixture composed of 0.5 parts by weight.

Production Example 13

In the same manner as in Preparation Example 1, 84 parts by weight of n-butyl acrylate (BA), 1 part by weight of 4-hydroxybutyl acrylate,

An acrylic copolymer was prepared using a monomer mixture consisting of 15 parts by weight.

Production Example 14

The same as in Preparation Example 1,

Instead of

An acrylic copolymer was prepared using.

<Comparative Production Example 1>

An acrylic copolymer was prepared in the same manner as in Preparation Example 1, using a monomer mixture consisting of 99 parts by weight of n-butyl acrylate (BA) and 1 part by weight of 4-hydroxybutyl acrylate.

<Comparative Production Example 2>

The same as in Preparation Example 1,

Instead, acrylic copolymers were prepared using acrylic acid (AA).

<Comparative Production Example 3>

The same as in Preparation Example 1,

Instead, dimethylaminoethyl acrylate was used to prepare an acrylic copolymer.

<Examples 1-19 and Comparative Examples 1-3>

As shown in Table 1 below, an acrylic copolymer, a crosslinking agent, an ionic antistatic agent, and a silane coupling agent were mixed, and then diluted in ethyl acetate to prepare a pressure-sensitive adhesive composition having a solid content of 15%.

TABLE 1

The pressure-sensitive adhesive composition prepared above was applied on a release film coated with a silicone release agent to have a thickness of 25 μm, and dried at 100 ° C. for 1 minute to form an adhesive layer.

A pressure-sensitive adhesive polarizing plate was prepared by laminating the pressure-sensitive adhesive layer prepared above on an iodine-based polarizing plate having a thickness of 185 μm. The prepared polarizing plate was stored for 20 days under conditions of 23 degreeC and 60% RH.

<Test Example>

The physical properties of the pressure-sensitive adhesive composition and pressure-sensitive adhesive polarizing plate prepared in Examples and Comparative Examples were measured by the following method, and the results are shown in Table 2 below.

1.Adhesion (N / 25mm)

The pressure sensitive adhesive polarizing plate was cut into 25 mm x 100 mm, the release film was peeled off, and then laminated onto a glass substrate (# 1737, Corning) at a pressure of 0.25 MPa and autoclaved to prepare a specimen.

The initial adhesive strength was 24 hours at 23 ° C. and 50% RH, and the warm adhesive was 48 hours at 50 ° C. and 50% RH, respectively, using a universal tensile tester (UTM, Instron). The pressure-sensitive adhesive layer was peeled off at a peel rate of 300 mm / min and a peel angle of 180 °, and measured. At this time, the measurement was performed under the conditions of 23 degreeC and 50% RH.

2. Heat resistance / humidity heat resistance

After peeling the release film of the polarizing plate with an adhesive and bonding the surface of an adhesive layer and Corning glass, after leaving for 300 hours at 80 degreeC (heat resistance) / 60 degreeC, 90 RH% (humidity heat resistance), the external appearance was confirmed.

<Evaluation Criteria>

Very large bubble or peeling visible: ×

Bubble and Peeling Admitted: △

Bubble or peeling is slightly visible but polarizer performance is maintained: ○

Bubbles and Peelings Unidentified: ◎

3.Surface Resistivity (Ω / □)

The prepared pressure-sensitive adhesive polarizing plate was measured 10 times each of three points of the pressure-sensitive adhesive layer using a surface resistance measuring instrument (MCP-HT450, Mitsubishi Chemical Co., Ltd.), and the average value thereof was represented.

Thereafter, the pressure-sensitive adhesive polarizing plate was left at 60 ° C. for 24 hours and then measured in the same manner as above.

4. Corrosion resistance of metal layer

After peeling the release film of the polarizing plate with an adhesive, after bonding the surface of an adhesive layer and an aluminum plate, it left for 250 hours in 60 degreeC and 95% RH atmosphere, and manufactured the specimen.

The adhesive layer was peeled from the said laminated body, the surface of the aluminum plate which contacted the said adhesive layer was visually observed, and the presence or absence of corrosion was evaluated.

<Evaluation Criteria>

The aluminum plate surface is not corroded at all: ◎

The surface of aluminum plate is slightly corroded, but the function of aluminum plate is maintained: ○

Surface of aluminum plate is corroded: ×

TABLE 2

As shown in Table 2, the pressure-sensitive adhesive composition of Examples 1 to 19 according to the present invention is superior to the initial and warm adhesive strength, durability and antistatic properties compared to Comparative Examples 1 to 3 and at the same time does not contain a corrosion inhibitor component separately It was confirmed that the corrosion of the metal layer can be effectively suppressed.

Claims (8)

1. Pressure-sensitive adhesive composition containing an acrylic copolymer and an ionic antistatic agent prepared by copolymerizing monomers containing an acrylate monomer having an amino alcohol group.
2. The pressure-sensitive adhesive composition of claim 1, wherein the acrylate monomer having an amino alcohol group is an acrylate monomer having a β-hydroxydialkylamino group (hydroxycarbon containing a tertiary amino group in adjacent carbon).
3. The pressure-sensitive adhesive composition of claim 1, wherein the acrylate-based monomer having an aminoalcohol group comprises a compound represented by the following Formula 1 or Formula 2:

   [Formula 1]

   

   (Wherein R ₁ is an aliphatic hydrocarbon containing or not containing N or O hetero atoms having 1 to 12 carbon atoms, and R ₂ is an aliphatic compound containing or not containing N or O hetero atoms having 1 to 12 carbon atoms) hydrocarbons, and, R3 is an aliphatic hydrocarbon group with or without a hetero element of N or O with a carbon number of 1 ~ 6, R4 is hydrogen or a methyl group, and R ₁ and R ₂ is a carbon adjacent to each other 5 ring or It may form a 6 ring, the ring may contain a hetero element.)

   [Formula 2]

   

   (Wherein R ₁ is an aliphatic hydrocarbon containing or not containing N or O hetero atoms having 1 to 12 carbon atoms, and R ₂ is an aliphatic compound containing or not containing N or O hetero atoms having 1 to 12 carbon atoms) hydrocarbons, and, R3 is an aliphatic hydrocarbon group with or without a hetero element of N or O with a carbon number of 1 ~ 6, R4 is hydrogen or a methyl group, and R ₁ and R ₂ is a carbon adjacent to each other 5 ring or It may form a 6 ring, the ring may contain a hetero element.)
4. The pressure-sensitive adhesive composition of claim 3, wherein the acrylate monomer having an amino alcohol group is at least one selected from the group consisting of Chemical Formulas 3 to 12:

   [Formula 3]

   

   [Formula 4]

   

   [Formula 5]

   

   [Formula 6]

   

   [Formula 7]

   

   [Formula 8]

   

   [Formula 9]

   

   [Formula 10]

   

   [Formula 11]

   

   [Formula 12]

   
5. The pressure-sensitive adhesive composition of claim 1, wherein the acrylic copolymer is prepared by copolymerizing monomers including a (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms and an acrylate monomer having an amino alcohol group.
6. The pressure-sensitive adhesive composition of claim 5, wherein the acrylate monomer having an amino alcohol group is included in an amount of 1 to 10 parts by weight based on 100 parts by weight of the (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms.
7. The method according to claim 1, wherein the ionic antistatic agent is a cation selected from the group consisting of alkali metal salts, ammonium salts, sulfonium salts and phosphonium salts;

   Pressure-sensitive adhesive composition which is an ionic salt consisting of an anion selected from the group consisting of fluorine-containing inorganic salts, fluorine-containing organic salts and iodine ions.
8. The pressure-sensitive adhesive composition of claim 1, wherein the pressure-sensitive adhesive composition further contains a crosslinking agent.