KR20140109705A - Adhesive composition - Google Patents

Abstract

The present invention relates to an adhesive composition and, more specifically, to an adhesive composition which has excellent durability and antistatic properties, since phenomena such as floating, bubbles, exfoliation and the like due to the surface transition of antistatic agents are not generated, by including ionic antistatic agents and acrylic copolymers containing monomers of chemical formula 1, and which is able to maintain light leakage preventing properties equal or superior to an existing adhesive composition. (In the formula, R_1 is H or CH_3; R_2 is a linear or cyclic hydrocarbon group of C1-C12; X is O, S, NR_3 or COO; R_3 is an alkyl group of C1-C6; and Y is a substituted or nonsubstituted aromatic hydrocarbon group).

Description

[0001] ADHESIVE COMPOSITION [0002]

The present invention relates to a pressure-sensitive adhesive composition having excellent light-shielding properties, antistatic properties and durability.

2. Description of the Related Art Generally, a liquid crystal display device (LCD) is provided with a liquid crystal cell containing a liquid crystal and a polarizer, and a suitable adhesive layer is used to bond the liquid crystal cell. As the pressure-sensitive adhesive, an acrylic pressure-sensitive adhesive based on an acrylic copolymer having excellent tackiness and transparency is often used.

When the releasing film is peeled off from the pressure-sensitive adhesive layer in the process of attaching the polarizing plate to the liquid crystal cell, static electricity is generated, and the generated static electricity affects the orientation of the liquid crystal to cause defects or to be introduced between the liquid crystal cell and the pressure- It causes pollution by foreign matter.

To improve this, an ionic antistatic agent is mixed in a pressure-sensitive adhesive composition. However, bleed-out phenomenon precipitated on the surface of the ionic antistatic agent may cause lifting, bubbling and peeling. In particular, such problems can be exacerbated by exposure to high temperature or high temperature and high humidity environments.

Further, the pressure-sensitive adhesive layer requires a high-temperature cohesive force in order to maintain durability, and a partially crosslinked viscoelastic material is used for this purpose. When a partially crosslinked structure is introduced into the pressure-sensitive adhesive layer, the pressure-sensitive adhesive layer has residual stress under a given deformation, and the polymer in the crosslinked structure is oriented in a specific direction to exhibit birefringence.

In recent years, as the liquid crystal panel has become larger, the polarizing plate becomes larger, and the residual stress of the protective film and the pressure-sensitive adhesive layer becomes larger. As a result, birefringence becomes large, and light leakage becomes very severe.

As a method for minimizing the light leakage occurring under such residual stress, a material showing birefringence of a positive value under residual stress is added (blended) to the final pressure-sensitive adhesive layer [Korean Patent Laid-Open Publication No. 2003-0069461] A method of copolymerizing monomers to minimize the total birefringence has been proposed (Japanese Laid-Open Patent Publication No. 2002-332468). In addition, a method of controlling birefringence by introducing an acrylic monomer containing an aromatic group has been proposed (Korean Patent No. 948,778).

Although the above methods can improve the light leakage phenomenon, there is a problem that the antistatic agent bleeds out due to the poor compatibility with the ionic antistatic agent contained in the pressure-sensitive adhesive, resulting in deteriorated durability.

The present invention provides a pressure-sensitive adhesive composition which is excellent in durability and can satisfy antistatic property because there is no phenomenon of lifting, bubbling and peeling due to surface migration of an antistatic agent while preventing light leakage occurring under residual stress, There is a purpose.

In order to achieve the above object, the present invention provides a pressure-sensitive adhesive composition comprising an acrylic copolymer containing an acrylic monomer represented by the following general formula (I) and an ionic antistatic agent.

Wherein R ₁ is H or CH ₃ , R ₂ is a linear or cyclic hydrocarbon group having 1 to 12 carbon atoms, X is O, S, NR ₃ or COO, and R ₃ is a C 1-6 And Y is a substituted or unsubstituted aromatic hydrocarbon group)

Preferably, R ₁ in the formula (1) is H or CH ₃ , R ₂ is an alkyl group having 1 to 12 carbon atoms, X is O, S, NR ₃ or COO and R ₃ is an alkyl group having 1 to 6 carbon atoms , And Y may be a phenyl group, a naphthyl group or a biphenyl group.

More preferably, the formula (1) may be at least one selected from the following formulas (2) to (7).

The acrylic copolymer may contain a (meth) acrylate monomer having an alkyl group of 1-12 carbon atoms and an acrylic monomer of the formula (1).

The acrylic monomer of Formula 1 may be contained in an amount of 5 to 30 parts by weight based on 100 parts by weight of the (meth) acrylate monomer having an alkyl group having 1-12 carbon atoms.

Wherein the ionic antistatic agent is selected from the group consisting of an alkali metal salt, an ammonium salt, a sulfonium salt, and a phosphonium salt; An ionic salt consisting of an anion selected from the group consisting of a fluorine-containing inorganic salt, a fluorine-containing organic salt and an iodide ion.

The ionic antistatic agent may be contained in an amount of 0.1 to 5 parts by weight based on 100 parts by weight of the acrylic copolymer.

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

The pressure-sensitive adhesive composition of the present invention maintains the light-shielding property equivalent to that of the prior art and has the advantage of being excellent in durability and satisfying the antistatic property because there is no phenomenon of lifting, bubbling and peeling due to surface migration of the antistatic agent .

Therefore, the pressure-sensitive adhesive composition of the present invention is highly applicable to static electricity avoiding applications in the field of plastic products, particularly electric / electronic devices, where static electricity is easily generated.

The present invention relates to a pressure-sensitive adhesive composition having excellent light-shielding properties, antistatic properties and durability.

Hereinafter, the present invention will be described in detail.

The pressure-sensitive adhesive composition of the present invention contains an acrylic copolymer containing an acrylic monomer represented by the following formula (1) and an ionic antistatic agent.

[Chemical Formula 1]

Wherein R ₁ is H or CH ₃ , R ₂ is a linear or cyclic hydrocarbon group having 1 to 12 carbon atoms, X is O, S, NR ₃ or COO, and R ₃ is a C 1-6 And Y is a substituted or unsubstituted aromatic hydrocarbon group)

The pressure-sensitive adhesive composition of the present invention contains an acrylic monomer of formula (1) having both a secondary hydroxy group and an aromatic hydrocarbon group in the acrylic copolymer, so that compatibility with the ionic antistatic agent is improved. The improvement in compatibility leads to suppression of the bleed-out phenomenon in which the antistatic agent component migrates to the surface and precipitates, and is excellent in durability. This can be suppressed even in a high temperature or high temperature / high humidity environment, and excellent durability can be maintained.

Further, the light leakage phenomenon can be prevented by the aromatic hydrocarbon group of the acrylic monomer.

Preferably, R ₁ in the formula (1) is H or CH ₃ , R ₂ is an alkyl group having 1 to 12 carbon atoms, X is O, S, NR ₃ or COO and R ₃ is an alkyl group having 1 to 6 carbon atoms , And Y may be a phenyl group, a naphthyl group or a biphenyl group.

More preferably, the formula (1) may be at least one selected from the following formulas (2) to (7).

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

The acrylic copolymer of the present invention preferably contains a (meth) acrylate monomer having an alkyl group of 1-12 carbon atoms and an acrylic monomer of the above formula (1). In the present invention, (meth) acrylate means acrylate and methacrylate, and the content of each component is based on the solid content.

Examples of the (meth) acrylate monomer having an alkyl group having 1-12 carbon atoms include n-butyl (meth) acrylate, 2-butyl (meth) acrylate, (Meth) acrylate, ethyl (meth) acrylate, methyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (Meth) acrylate, n-butyl acrylate, nonyl (meth) acrylate, decyl (meth) acrylate and lauryl Or a mixture thereof. These may be used alone or in combination of two or more.

The acrylic monomer of Formula 1 preferably contains 5 to 30 parts by weight, more preferably 8 to 15 parts by weight, based on 100 parts by weight of the (meth) acrylate monomer having an alkyl group having 1-12 carbon atoms. When the content is less than 5 parts by weight, the effect of improving the compatibility of the antistatic agent is insufficient, so that it is difficult to secure durability, or the content of the aromatic ring may be small and the light leakage improving effect may be insufficient. Also, when the content exceeds 30 parts by weight, the light leakage property and the heat resistance property may be deteriorated.

The acrylic copolymer of the present invention may further contain a polymerizable monomer having a crosslinkable functional group in addition to the acrylic monomer of the above formula (1). The polymerizable monomer having a crosslinkable functional group has a role of reinforcing the cohesive strength or adhesive strength of the pressure-sensitive adhesive composition by chemical bonding to impart durability and cutability.

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 a monomer having a carboxyl group. These polymerizable monomers may be used singly or in combination.

It is more preferable to suppress the occurrence of corrosion by the pressure-sensitive adhesive composition by using a component that does not generate the hydrogen ion (H ⁺ ). That is, it is preferable to exclude the monomer having a carboxylic acid group and the like.

Specific examples of the monomer having a hydroxyl group include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl Hydroxyethyl (meth) acrylate, 2-hydroxypropylene glycol (meth) acrylate, hydroxyalkylene having 2 to 4 carbon atoms in the alkylene group (Meth) acrylate, 4-hydroxybutyl vinyl ether, 5-hydroxypentyl vinyl ether, 6-hydroxyhexyl vinyl ether, 7-hydroxyheptyl vinyl ether, 8-hydroxyoctyl vinyl ether, 4-hydroxybutyl vinyl ether, and 2-hydroxybutyl vinyl ether. Of these, 4-hydroxybutyl vinyl ether is preferable.

Examples of the monomer having an amide group include (meth) acrylamide, N-isopropyl acrylamide, N-tertiary butyl acrylamide, 3-hydroxypropyl (meth) acrylamide, 4-hydroxybutyl (Meth) acrylamide, 8-hydroxyoctyl (meth) acrylamide, and 2-hydroxyethylhexyl (meth) acrylamide. Of these, (meth) acrylamide is preferable.

Examples of the monomer having a tertiary amine group include N, N- (dimethylamino) ethyl (meth) acrylate, N, N- (diethylamino) ethyl (meth) Methacrylate, and the like.

The polymerizable monomer having such a crosslinkable functional group is preferably contained in an amount of 0.05 to 10 parts by weight, more preferably 0.1 to 8 parts by weight, per 100 parts by weight of the (meth) acrylate monomer having an alkyl group having 1-12 carbon atoms good. When the content is less than 0.05 part by weight, the cohesive force of the pressure-sensitive adhesive becomes small and durability may be deteriorated. When the content is more than 10 parts by weight, a high gel fraction may lower the adhesive strength and cause durability problems.

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

The method for producing the copolymer is not particularly limited and can be produced by methods 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 polymerization can be used.

The acrylic copolymer preferably has a weight average molecular weight (polystyrene conversion, Mw) of 50,000 to 2,000,000, more preferably 400,000 to 2,000,000 as measured by Gel Permeation Chromatography (GPC). When the weight-average molecular weight is less than 50,000, cohesion between co-polymers may be insufficient, which may cause problems in adhesion durability. If the weight average molecular weight is more than 2,000,000, a large amount of a diluting solvent may be required in order to ensure fairness in coating.

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

A cation selected from the group consisting of an alkali metal salt, an ammonium salt, a sulfonium salt and a phosphonium salt; An ionic salt consisting of an anion selected from the group consisting of a fluorine-containing inorganic salt, a fluorine-containing organic salt and an iodide ion.

Such an ionic antistatic agent may be contained in an amount of 0.1 to 5 parts by weight, preferably 0.5 to 3 parts by weight, based on 100 parts by weight of the acrylic copolymer. When the content is less than 0.1 part by weight, the antistatic property may be insufficient. When the content is more than 5 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.

The crosslinking agent can improve the adhesion and durability, and can maintain the reliability at a high temperature and the shape of the pressure-sensitive adhesive.

The cross-linking agent may be an isocyanate-based, epoxy-based, melamine-based, peroxide-based, metal chelating-based, oxazoline-based, or the like. Preferred is a double isocyanate-based or epoxy-based.

Examples of the isocyanate-based isocyanate include isocyanate-based compounds such as tolylene diisocyanate, xylene diisocyanate, 2,4-diphenylmethane diisocyanate, 4,4-diphenylmethane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, tetramethyl xylene diisocyanate, Diisocyanate compounds such as isocyanate; An adduct obtained by reacting 3 moles of a diisocyanate compound with 1 mole of a polyhydric alcohol compound such as trimethylolpropane, an isocyanurate compound in which 3 moles of a diisocyanate compound is self-condensed, a diisocyanate obtained from 2 moles of 3 moles of a diisocyanate compound And multifunctional isocyanate compounds containing three functional groups such as burette, triphenylmethane triisocyanate and methylene bistriisocyanate in which the remaining one mole of diisocyanate is condensed in urea.

The epoxy system may be an ethylene glycol diglycidyl ether, a diethylene glycol diglycidyl ether, a polyethylene glycol diglycidyl ether, a propylene glycol diglycidyl ether, a tripropylene glycol diglycidyl ether, a polypropylene glycol di Hexanediol diglycidyl ether, polytetramethylene glycol diglycidyl ether, glycerol diglycidyl ether, glycerol triglycidyl ether, diethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, Glycerol polyglycidyl ether, polyglycerol polyglycidyl ether, resorcinol diglycidyl ether, 2,2-dibromoneopentyl glycol diglycidyl ether, trimethylol propane triglycidyl ether, pentaerythritol poly Glycidyl ether, sorbitol polyglycidyl ether, adipic acid diglycidyl ester, phthalic acid diglycidyl ester, tris (glycidyl) isocyanurate N, N, N ', N'-tetraglycidyl-m-hexyldicyclohexyl) isocyanurate, 1,3-bis (N, N-glycidylaminomethyl) cyclohexane, Xylylenediamine, and the like.

Examples of the melamine type include hexamethylol melamine, hexamethoxymethyl melamine, and hexabutoxymethyl melamine.

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 strength may be decreased due to insufficient crosslinking, which may deteriorate the durability of the adhesive durability and the cutability. If the content is more than 15 parts by weight, the residual stress due to the excessive crosslinking reaction may be deteriorated.

In addition to the above components, the pressure-sensitive adhesive composition may further contain various additives such as a silane coupling agent, a tackifier resin, an antioxidant, a leveling agent, a surface lubricant, a dye, an antioxidant, and the like in order to control the adhesion, cohesion, viscosity, A pigment, a defoaming agent, a filler, a light stabilizer, and the like.

The double silane coupling agent serves to improve the adhesion between the pressure-sensitive adhesive and the substrate. Therefore, it is preferable that the double silane coupling agent contains an alkoxysilane containing an amino group, an epoxy group, an acetoacetyl group, a polyalkylene glycol group, an acryl group, Can be used.

The amount of such an additive can be appropriately controlled within a range that does not impair the effect of the present invention. For example, the silane coupling agent is added in an amount of 0.1 to 2 parts by weight, preferably 0.1 to 2 parts by weight, per 100 parts by weight of the acrylic copolymer, May be contained in an amount of 0.1 to 0.5 parts by weight. If the content is less than 0.1 parts by weight, the adhesion may be deteriorated. If the content is more than 2 parts by weight, peeling may occur under heat-resistant conditions.

The pressure-sensitive adhesive composition of the present invention can be used particularly as a pressure-sensitive adhesive for a polarizing plate or a pressure-sensitive adhesive for a surface protective film for bonding with a liquid crystal cell. It can be used not only 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 electronic component adhesive, but also a general commercial adhesive sheet product.

It will be apparent to those skilled in the art that various modifications and variations can be made in the present invention without departing from the spirit or scope of the present invention. Such variations and modifications are intended to be within the scope of the appended claims.

Manufacturing example  : Acrylic copolymer preparation

Manufacturing example  One

의 아크릴 단량체(화학식 2) 10중량부로 이루어진 단량체 혼합물을 투입한 후, 용제로 아세톤 100중량부를 투입하였다. 그 다음 산소를 제거하기 위하여 질소가스를 1시간 동안 퍼징한 후, 62℃로 유지하였다. 상기 혼합물을 균일하게 한 후, 반응개시제로 아조비스이소부티로니트릴(AIBN) 0.07중량부를 투입하고, 6시간 동안 반응시켜 중량평균분자량이 약 100만인 아크릴계 공중합체를 제조하였다.
80 parts by weight of n-butyl acrylate (BA), 8.0 parts by weight of methyl acrylate (MA), and 2.0 parts by weight of 2-hydroxyethyl acrylate (weight ratio) were added to a 1 L reactor equipped with a cooling device, part,

And 10 parts by weight of an acrylic monomer (Formula 2), and then 100 parts by weight of acetone was added as a solvent. Nitrogen gas was then purged for 1 hour to remove oxygen and then maintained at 62 ° C. After the mixture was homogenized, 0.07 part 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 1,000,000.

Manufacturing example  2

(화학식 2) 대신에

(화학식 3)을 사용하여 중량평균분자량이 약 100만인 아크릴계 공중합체를 제조하였다.
The procedure of Preparation Example 1 was repeated, except that the acrylic monomer

(2) instead of

(Formula 3), an acrylic copolymer having a weight average molecular weight of about 1,000,000 was prepared.

Manufacturing example  3

(화학식 2) 대신에

(화학식 4)을 사용하여 중량평균분자량이 약 100만인 아크릴계 공중합체를 제조하였다.
The procedure of Preparation Example 1 was repeated, except that the acrylic monomer

(2) instead of

(Formula 4), an acrylic copolymer having a weight average molecular weight of about 1,000,000 was prepared.

Manufacturing example  4

(화학식 2) 대신에

(화학식 5)을 사용하여 중량평균분자량이 약 100만인 아크릴계 공중합체를 제조하였다.
The procedure of Preparation Example 1 was repeated, except that the acrylic monomer

(2) instead of

(Formula 5), an acrylic copolymer having a weight average molecular weight of about 1,000,000 was prepared.

Manufacturing example  5

(화학식 2) 대신에

(화학식 6)을 사용하여 중량평균분자량이 약 100만인 아크릴계 공중합체를 제조하였다.
The procedure of Preparation Example 1 was repeated, except that the acrylic monomer

(2) instead of

(Formula 6), an acrylic copolymer having a weight average molecular weight of about 1,000,000 was prepared.

Manufacturing example  6

(화학식 2) 대신에

(화학식 7)을 사용하여 중량평균분자량이 약 100만인 아크릴계 공중합체를 제조하였다.
The procedure of Preparation Example 1 was repeated, except that the acrylic monomer

(2) instead of

(Formula 7), an acrylic copolymer having a weight average molecular weight of about 1,000,000 was prepared.

Manufacturing example  7

의 아크릴 단량체(화학식 2) 5중량부를 사용하고, n-부틸아크릴레이트(BA) 85중량부를 사용하여 중량평균분자량이 약 100만인 아크릴계 공중합체를 제조하였다.
The procedure of Preparation Example 1 was repeated,

5 parts by weight of an acrylic monomer (Formula 2) and 85 parts by weight of n-butyl acrylate (BA) were used to prepare an acrylic copolymer having a weight average molecular weight of about 1,000,000.

Manufacturing example  8

의 아크릴 단량체(화학식 2) 20중량부를 사용하고, n-부틸아크릴레이트(BA) 70중량부를 사용하여 중량평균분자량이 약 100만인 아크릴계 공중합체를 제조하였다.
The procedure of Preparation Example 1 was repeated,

20 parts by weight of an acrylic monomer (Formula 2) was used and 70 parts by weight of n-butyl acrylate (BA) was used to prepare an acrylic copolymer having a weight average molecular weight of about 1,000,000.

compare Manufacturing example  One

의 아크릴 단량체(화학식 2)의 사용없이, n-부틸아크릴레이트(BA) 90중량부를 사용하여 중량평균분자량이 약 100만인 아크릴계 공중합체를 제조하였다.
The procedure of Preparation Example 1 was repeated,

Acrylic copolymer having a weight average molecular weight of about 1,000,000 was prepared by using 90 parts by weight of n-butyl acrylate (BA) without using the acrylic monomer (Formula 2).

compare Manufacturing example  2

(화학식 2) 대신에 페녹시에틸아크릴레이트(PEA)를 사용하여 중량평균분자량이 약 100만인 아크릴계 공중합체를 제조하였다.
The procedure of Preparation Example 1 was repeated, except that the acrylic monomer

An acrylic copolymer having a weight average molecular weight of about 1,000,000 was prepared by using phenoxyethyl acrylate (PEA) instead of the compound represented by Formula (2).

compare Manufacturing example  3

(화학식 2) 대신에 벤질메타크릴레이트(BzMA)를 사용하여 중량평균분자량이 약 100만인 아크릴계 공중합체를 제조하였다.
The procedure of Preparation Example 1 was repeated, except that the acrylic monomer

(BzMA) was used instead of benzyl methacrylate (BzMA) to prepare an acrylic copolymer having a weight average molecular weight of about 1,000,000.

compare Manufacturing example  4

(화학식 2) 대신에 (페녹시)에톡시에틸아크릴레이트(PEA-2)를 사용하여 중량평균분자량이 약 100만인 아크릴계 공중합체를 제조하였다.
The procedure of Preparation Example 1 was repeated, except that the acrylic monomer

(PEA-2) was used instead of (Phenoxy) ethoxyethyl acrylate (Formula 2) to prepare an acrylic copolymer having a weight average molecular weight of about 1,000,000.

Example  1-12 and Comparative Example  1-4

An acrylic copolymer, an ionic antistatic agent, a crosslinking agent and a silane coupling agent (Shin-Etsu KBM-403, 0.5 part by weight) were mixed and diluted with ethyl acetate to prepare a pressure-sensitive adhesive composition having a solid concentration of 15%. At this time, Table 1 shows an acrylic copolymer, an ionic antistatic agent, and a crosslinking agent, and the same components and contents were used for the silane coupling agent.

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

The pressure-sensitive adhesive layer prepared above was laminated to an iodine-based polarizing plate having a thickness of 185 μm by pressure-sensitive adhesive processing to produce a polarizer with a pressure-sensitive adhesive.

division
(Parts by weight) Acrylic copolymer Ionic antistatic agent Cross-linking agent Manufacturing example Comparative Manufacturing Example A-1 A-2 A-3 B-1 B-2 B-3 Example 1 1 (100) - 2.0 - - 1.0 - - Example 2 2 (100) - 2.0 - - 1.0 - - Example 3 3 (100) - 2.0 - - 1.0 - - Example 4 4 (100) - 2.0 - - 1.0 - - Example 5 5 (100) - 2.0 - - 1.0 - - Example 6 6 (100) - 2.0 - - 1.0 - - Example 7 7 (100) - 2.0 - - 1.0 - - Example 8 8 (100) - 2.0 - - 1.0 - - Example 9 1 (100) - - 2.0 - 1.0 - - Example 10 1 (100) - - - 2.0 1.0 - - Example 11 1 (100) - 2.0 - - - 1.0 - Example 12 1 (100) - 2.0 - - - - 1.0 Comparative Example 1 - 1 (100) 2.0 - - 1.0 - - Comparative Example 2 - 2 (100) 2.0 - - 1.0 - - Comparative Example 3 - 3 (100) 2.0 - - 1.0 - - Comparative Example 4 - 4 (100) 2.0 - - 1.0 - - A-1; 1-hexyl-4-methylpyridinium hexafluorophosphate
A-2; LiI
A-3; NaPF ₆
B-1: Coronate-L (TDI crosslinking agent, CORONATE-L, Japan Urethane Industry)
B-2: Coronate-HXR (HDI crosslinking agent, CORONATE-HXR, Japan Urethane Industry)
B-3: Takenate-110N (XDI crosslinking agent, TAKENATE-110N Mitsui Chemicals)

Test Example

The properties of the pressure-sensitive adhesive composition and the polarizer with a pressure-sensitive adhesive prepared in the above Examples and Comparative Examples were measured by the following methods, and the results are shown in Table 2 below.

1. Heat resistance

The release film of the polarizing plate with a pressure-sensitive adhesive was removed, bonded to the surface of the pressure-sensitive adhesive layer and Corning glass, and then left at 60 DEG C for 300 hours.

<Evaluation Criteria>

Bubbles and peeling phenomena More than 3 poisoned: ×

Bubbles and peeling phenomena Less than 2 poised: ○

Bubbles and peeling phenomenon are observed: ◎

2. Light resistance

In order to investigate the uniformity of light transmittance using the same specimen as above, it was observed whether light leaks from the dark room using a backlight. As a method of testing the light transmission uniformity, a coated polarizing plate (200 mm x 200 mm) was attached to both surfaces of a glass substrate (210 mm x 210 mm x 0.7 mm) at 90 degrees.

<Evaluation Criteria>

&Amp; cir &amp; &amp; cir &amp; &amp; cir &amp; &amp; cir &

○: slight non-uniformity of light transmittance

?: Slight non-uniformity of light transmittance

X: large amount of non-uniformity of light transmittance

division Heat resistance Light resistance Example 1 ◎ ◎ Example 2 ◎ ◎ Example 3 ◎ ◎ Example 4 ◎ ◎ Example 5 ◎ ◎ Example 6 ◎ ◎ Example 7 ○ ○ Example 8 ◎ ○ Example 9 ○ ◎ Example 10 ○ ◎ Example 11 ◎ ◎ Example 12 ◎ ◎ Comparative Example 1 × × Comparative Example 2 × ○ Comparative Example 3 × ○ Comparative Example 4 × ○

As shown in Table 2, the pressure-sensitive adhesive compositions of Examples 1 to 12 containing an acrylic copolymer containing an acrylic monomer of Formula 1 according to the present invention had heat resistance and light-shielding properties as compared with Comparative Examples 1 to 4 And it was confirmed that it was excellent.

Claims (8)

A pressure-sensitive adhesive composition comprising an acrylic copolymer containing an acrylic monomer represented by the following formula (1) and an ionic antistatic agent:
[Chemical Formula 1]

Wherein R ₁ is H or CH ₃ , R ₂ is a linear or cyclic hydrocarbon group having 1 to 12 carbon atoms, X is O, S, NR ₃ or COO, and R ₃ is a C 1-6 And Y is a substituted or unsubstituted aromatic hydrocarbon group)
[3] The compound according to claim 1, wherein R ₁ is H or CH ₃ , R ₂ is an alkyl group having 1 to 12 carbon atoms, X is O, S, NR ₃ or COO, R ₃ is an alkyl group having 1 to 6 carbon atoms And Y is a phenyl group, a naphthyl group or a biphenyl group.
The pressure-sensitive adhesive composition according to claim 2, wherein the compound represented by Formula 1 is at least one selected from the following Formulas 2 to 7:
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

The pressure-sensitive adhesive composition according to claim 1, wherein the acrylic copolymer contains a (meth) acrylate monomer having an alkyl group of 1-12 carbon atoms and an acrylic monomer of the formula (1).
The pressure-sensitive adhesive composition according to claim 4, wherein the acrylic monomer of Formula 1 contains 5 to 30 parts by weight per 100 parts by weight of the (meth) acrylate monomer having an alkyl group having 1-12 carbon atoms.
The ionic antistatic composition of claim 1, wherein the ionic antistatic agent is selected from the group consisting of an alkali metal salt, an ammonium salt, a sulfonium salt, and a phosphonium salt;
Is an ionic salt comprising an anion selected from the group consisting of a fluorine-containing inorganic salt, a fluorine-containing organic salt and an iodide ion.
The pressure-sensitive adhesive composition according to claim 6, wherein the ionic antistatic agent is contained in an amount of 0.1 to 5 parts by weight based on 100 parts by weight of the acrylic copolymer.
The pressure-sensitive adhesive composition according to claim 1, wherein the pressure-sensitive adhesive composition further comprises a crosslinking agent.