KR102003584B1 - Adehesive Composition and Polarizing Plate Containing the Same - Google Patents

Abstract

The present invention provides a pressure-sensitive adhesive composition comprising an acrylic copolymer containing a monomer having a hydroxyl group and an ethylene glycol group and a crosslinking agent, a polarizing plate comprising the same, and a liquid crystal display device. The pressure-sensitive adhesive composition according to the present invention exhibits excellent antistatic property and excellent adhesive durability and reworkability.

Description

[0001] The present invention relates to a pressure-sensitive adhesive composition and a polarizing plate comprising the same,

The present invention relates to a pressure-sensitive adhesive composition and a polarizing plate comprising the same, and more particularly, to a pressure-sensitive adhesive composition having excellent antistatic properties as well as durability and reworkability, a polarizing plate and a liquid crystal display including the same.

2. Description of the Related Art A liquid crystal display device (LCD) includes a liquid crystal cell and a liquid crystal panel including a polarizing plate bonded to both sides of the liquid crystal cell via an adhesive layer.

The pressure-sensitive adhesive for bonding a liquid crystal cell and a polarizing plate is preferably a pressure-sensitive adhesive for bonding between a liquid crystal cell and a polarizing plate, in which a durability such as heat resistance, heat resistance, heat shock resistance, thermal shock resistance, cold resistance, And the antistatic property for preventing the static electricity generated when the release film is removed for the polarizing plate bonding must be satisfied at the same time. Among them, the characteristics of the pressure-sensitive adhesive required for durability and reworkability are in conflict with each other, so that satisfying all of them is not completely solved.

Korean Patent Publication No. 10-2012-0109398 discloses a pressure-sensitive adhesive composition comprising an acrylic polymer and an antistatic agent containing a (meth) acrylic acid ester monomer, a hydroxyl group-containing monomer, a carboxyl group-containing monomer and a monomer having an alkylene oxide unit as polymerization units . The pressure-sensitive adhesive composition exhibits a stable antistatic property, but has a problem of poor durability and reworkability.

Korean Patent Publication No. 10-2012-0109398

It is an object of the present invention to provide a pressure-sensitive adhesive composition which is excellent in not only antistatic properties but also durability and reworkability.

Another object of the present invention is to provide a polarizing plate in which a pressure-sensitive adhesive layer composed of the pressure-sensitive adhesive composition is laminated.

It is still another object of the present invention to provide a liquid crystal display having the polarizing plate on at least one side of a liquid crystal cell.

On the other hand, the present invention provides a pressure-sensitive adhesive composition comprising an acrylic copolymer containing a monomer represented by the following formula (1) and a crosslinking agent.

[Chemical Formula 1]

In the above formulas,

n is an integer of 0 to 10,

R is an alkyl group of hydrogen or C ₁ -C _6.

In one embodiment of the present invention, the monomer of Formula 1 may be contained in an amount of 0.1 to 20% by weight based on 100% by weight of the total monomers used in the production of the acrylic copolymer.

In one embodiment of the present invention, the pressure-sensitive adhesive composition may further include an antistatic agent.

On the other hand, the present invention provides a polarizing plate in which a pressure-sensitive adhesive layer composed of the pressure-sensitive adhesive composition is laminated.

On the other hand, the present invention provides a liquid crystal display in which the polarizing plate is provided on at least one surface of a liquid crystal cell.

The pressure-sensitive adhesive composition according to the present invention exhibits excellent antistatic property and excellent adhesive durability under high-temperature or high-temperature and high-humidity conditions, and has excellent reworkability.

Hereinafter, the present invention will be described in more detail.

An embodiment of the present invention relates to a pressure-sensitive adhesive composition comprising an acrylic copolymer containing a monomer represented by the following formula (1) and a crosslinking agent.

[Chemical Formula 1]

In this formula,

n is an integer of 0 to 10, preferably an integer of 0 to 5,

R is hydrogen or methyl is an alkyl group of hydrogen or C ₁ -C _6, preferably.

As used herein, the C ₁ -C ₆ alkyl group means a linear or branched monovalent hydrocarbon having 1 to 6 carbon atoms, for example, methyl, ethyl, n-propyl, i-propyl, , i-butyl, t-butyl, n-pentyl, n-hexyl, and the like.

In one embodiment of the present invention, the monomer of Formula 1 may be contained in an amount of 0.1 to 20% by weight, preferably 1 to 10% by weight, based on 100% by weight of the total monomers used in the production of the acrylic copolymer. If the content is less than 0.1% by weight, sufficient antistatic property and recrystallization resistance can not be exhibited and there may be a problem of poor durability due to poor cohesive strength due to lowering of the degree of crosslinking. When the content is more than 20% by weight, There may be a problem of interfacial peeling due to excessive cohesion due to the above.

In one embodiment of the present invention, the acrylic copolymer may include a (meth) acrylate monomer having an alkyl group of 1-12 carbon atoms and a polymerizable monomer having a crosslinkable functional group.

Here, (meth) acrylate means acrylate and methacrylate.

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-octyl (meth) acrylate, isooctyl (meth) acrylate, n-octyl These may be used alone or in combination of two or more. Of these, n-butyl acrylate, methyl (meth) acrylate or a mixture thereof is preferable. These may be used alone or in combination of two or more.

The (meth) acrylate monomer having an alkyl group having 1-12 carbon atoms is preferably contained in an amount of 13 to 99% by weight, more preferably 80 to 95% by weight, based on 100% by weight of the total monomers used in the production of the acrylic copolymer More preferable. When the content is less than 13% by weight, the adhesive strength is not sufficient, and when it is more than 99% by weight, the cohesive strength may be lowered.

The polymerizable monomer having a cross-linkable functional group is a component for imparting durability and cutability by reinforcing the cohesive force or adhesive strength of the pressure-sensitive adhesive composition by chemical bonding, and examples thereof include monomers having a hydroxy group and monomers having a carboxyl group, These may be used alone or in combination of two or more.

Examples of the monomer having a hydroxy group include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl Hydroxypropyleneglycol (meth) acrylate, hydroxyalkylene glycol having 2 to 4 carbon atoms in the alkylene group (e.g., methoxyethyl (meth) acrylate, Hydroxybutyl vinyl ether, 8-hydroxyoctyl vinyl ether, 9-hydroxynonyl (meth) acrylate, 4-hydroxybutyl vinyl ether, Vinyl ether, and 10-hydroxydecyl vinyl ether. Of these, 2-hydroxyethyl (meth) acrylate and 4-hydroxybutyl vinyl ether are preferable.

Examples of the monomer having a carboxyl group include monovalent acids such as (meth) acrylic acid and crotonic acid; Dicarboxylic acids such as maleic acid, itaconic acid, and fumaric acid, and monoalkyl esters thereof; 3- (meth) acryloylpropionic acid; A succinic anhydride ring-opening addition adduct of 2-hydroxyalkyl (meth) acrylate in which the alkyl group has 2 to 4 carbon atoms, anhydrous succinic ring opening adduct of a hydroxyalkylene glycol (meth) acrylate having 2 to 4 carbon atoms in the alkylene group , And compounds obtained by ring-opening addition of succinic anhydride to a caprolactone adduct of 2-hydroxyalkyl (meth) acrylate in which the alkyl group has 2-3 carbon atoms. Of these, (meth) acrylic acid is preferable.

The acrylic copolymer may further contain other polymerizable monomers other than the monomers in an amount not lowering the adhesive strength, for example, 10% by weight or less based on the total amount.

The method for producing the copolymer is not particularly limited and can be produced by a method such as bulk polymerization, solution polymerization, emulsion polymerization or suspension polymerization, which is 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 generally has a weight average molecular weight (in terms of polystyrene, Mw) measured by gel permeation chromatography (GPC) of usually 50,000 to 2,000,000, preferably 500,000 to 1,700,000. 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.

In one embodiment of the present invention, the cross-linking agent is an isocyanate-based, epoxy-based, peroxide-based, metal chelating-based, oxalate-based, And a zolene series. These may be used singly or in combination of two or more kinds. Of these, an isocyanate-based compound is preferable.

Specifically, diisocyanate compounds such as tolylene diisocyanate, xylene diisocyanate, hexamethylene diisocyanate, 2,4- or 4,4-diphenylmethane diisocyanate, and the like; And adducts of polyhydric alcohol compounds such as trimethylol propane of diisocyanate.

In addition to the isocyanate crosslinking agent, melamine derivatives such as hexamethylol melamine, hexamethoxymethyl melamine, hexabutoxymethyl melamine and the like; Polyepoxy compounds, for example, bisphenol A and epichlorohydrin condensate type epoxy compounds; At least one crosslinking agent selected from the group consisting of polyglycidyl ether of polyoxyalkylene polyol, glycerin di- or triglycidyl ether and tetraglycidyl xylylene diamine may be added and used together.

The crosslinking agent may be contained in an amount of 0.1 to 5 parts by weight, preferably 0.1 to 1 part by weight, based on 100 parts by weight of the acrylic copolymer. If the content is less than 0.1 parts by weight, the cohesive force may become small due to insufficient crosslinking, which may deteriorate the durability of the adhesive durability and the cutability. If the content exceeds 5 parts by weight, a problem may occur in the residual stress relaxation due to the excessive crosslinking reaction.

The pressure-sensitive adhesive composition according to one embodiment of the present invention may further include an antistatic agent.

As the antistatic agent, for example, an organic cation or an alkali metal cation such as ammonium, phosphonium, or sulfonium can be used as the cation. Specific examples of the organic cations include quaternary ammonium salts substituted with four alkyl groups such as tetrabutylammonium, 1-ethylpyridinium, 1-butylpyridinium, 1-hexylpyridinium, 1-butyl- Butyl-4-methylpyridinium, 1-hexyl-3-methylpyridinium, 1-hexyl-4-methylpyridinium, Pyridinium, pyridinium salts in which the N of the pyridine is substituted with an alkyl group, alkyl groups such as 1-methyl-3-butylimidazolium and 1-methyl-3-hexylimidazolium, Substituted imidazolium salts, quaternary phosphonium salts having four alkyl groups such as tetrabutylphosphonium, and tertiary sulfonium salts having three alkyl groups such as tributylsulfonium. The alkali metal may be lithium, sodium, potassium or cesium, preferably lithium, sodium or potassium. These may be used alone or in combination of two or more.

Anion as OTf ^- (methanesulfonate trifluoroacetate), OTs ^- (toluene-4-sulfonate), OMs ^{- (methanesulfonate), Cl -, Br -,} I -, AlCl 4 -, Al 2 Cl 7 - _{^{, BF 4 -, PF 6 -}} , ClO 4 -, NO 3 -, CH 3 COO -, CF 3 COO -, CH 3 SO 3 -, CF 3 SO 3 -, (CF 3 SO 2) 2 N -, ( ^{_{CF 3 SO 2) 3 C -}} , AsF 6 -, SbF 6 -, NbF 6 -, TaF 6 -, F (HF) n -, (CN) 2 N -, C 4 F 9 SO 3 -, (C 2 F ₅ SO ₂ ) ₂ N ^- , C ₃ F ₇ COO ^- , (CF ₃ SO ₂ ) (CF ₃ CO) N ^- and the like.

The content of the antistatic agent is not particularly limited as long as it is within the range of its function, and may be, for example, 0.1 to 4 parts by weight based on 100 parts by weight of the acrylic copolymer. When the above-mentioned range is satisfied, excellent antistatic properties can be exhibited, and optical properties and durability of the polarizing plate can be remarkably improved.

The pressure-sensitive adhesive composition according to one embodiment of the present invention may further include a silane coupling agent.

The type of the silane coupling agent is not particularly limited, and examples thereof include vinylchlorosilane, vinyltrimethoxysilane, vinyltriethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3- Glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethylethoxysilane, 3-glycidoxypropyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, p-styryltrimethoxysilane, 3- Methacryloxypropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-acryloxypropyltrimethoxy Silane, N-2- (aminoethyl) -3-aminopropylmethyldimethoxysilane, N-2- (aminoethyl) Propylmethyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxy Silane, 3-triethoxysilyl-N- (1,3-dimethylbutylidene) propylamine, N-phenyl-3-aminopropyltrimethoxysilane, 3-chloropropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, bis (triethoxysilylpropyl) tetrasulfide, 3-isocyanatopropyltriethoxysilane, and the like. These may be used alone or in combination of two or more.

The silane coupling agent may be added in an amount of 0.01 to 5 parts by weight, preferably 0.1 to 5 parts by weight based on 100 parts by weight of the acrylic copolymer. When the content is less than 0.01 part by weight, the amount is too small and durability is not expected to be improved. If the content is more than 5 parts by weight, the cohesive strength is excessively increased.

The pressure-sensitive adhesive composition according to one embodiment of the present invention may further contain additives such as a tackifier resin, an antioxidant, a corrosion inhibitor, a leveling agent, a surface lubricant, a dye, and the like in order to control adhesion, cohesion, viscosity, elastic modulus, , A pigment, a defoaming agent, a filler, a light stabilizer, and the like.

The pressure-sensitive adhesive composition of the present invention can be used 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. In addition, 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 or a medical patch.

One embodiment of the present invention relates to a polarizing plate in which a pressure-sensitive adhesive layer composed of the pressure-sensitive adhesive composition is laminated.

The thickness of the pressure-sensitive adhesive layer can be adjusted according to the adhesive force, and is preferably 3 to 100 탆, more preferably 10 to 100 탆.

Such a polarizing plate can be applied to all ordinary liquid crystal display devices, and concretely, a liquid crystal display device including a liquid crystal panel in which a polarizing plate in which the pressure-sensitive adhesive layer is laminated is bonded to at least one surface of a liquid crystal cell can be constituted.

Therefore, one embodiment of the present invention relates to a liquid crystal display device provided with the polarizing plate on at least one surface of a liquid crystal cell.

Hereinafter, the present invention will be described more specifically with reference to Examples, Comparative Examples and Experimental Examples. It should be apparent to those skilled in the art that these examples, comparative examples and experimental examples are only for illustrating the present invention, and the scope of the present invention is not limited thereto.

Manufacturing example  1: Preparation of monomer-containing acrylic copolymer of formula (1)

82 parts by weight of n-butyl acrylate (BA), 10 parts by weight of methyl acrylate (MA), 2 parts by weight of 2-hydroxylethyl acrylate (2 parts by weight), and the like were charged in a 1 L reactor equipped with a cooling device, 1 part by weight of acrylic acid (AA) and 6 parts by weight of monomer (A-1) represented by the formula (1) wherein n is 0 and R is hydrogen, 100 parts by weight. Nitrogen gas was then purged for 1 hour to remove oxygen and then maintained at 62 占 폚. After the mixture was homogenized, 0.07 part by weight of azobisisobutyronitrile (AIBN) as a reaction initiator was added and reacted for 8 hours to prepare an acrylic copolymer having a weight average molecular weight of about 1,600,000.

Manufacturing example  2: Preparation of monomer-containing acrylic copolymer of formula (1)

An acrylic copolymer having a weight average molecular weight of about 1,600,000 was prepared in the same manner as in Preparation Example 1, except that 85 parts by weight of n-butyl acrylate (BA) and 3 parts by weight of the monomer (A-1) Respectively.

Manufacturing example  3: Preparation of monomer-containing acrylic copolymer of formula (1)

Except that the monomer (A-2) of the formula (1) wherein n is 1 and R is hydrogen was used instead of the monomer (A-1) of the formula (1) Acrylic copolymer was prepared.

Manufacturing example  4: Preparation of monomer-containing acrylic copolymer of formula (1)

An acrylic copolymer having a weight average molecular weight of about 1,600,000 was prepared in the same manner as in Production Example 2, except that the monomer (A-2) of the formula (1) was used instead of the monomer (A-1)

Manufacturing example  5: Preparation of monomer-containing acrylic copolymer of formula (1)

Was obtained in the same manner as in Preparation Example 1, except for using the monomer (A-3) of the formula (1) wherein n is 1 and R is methyl instead of the monomer (A-1) Acrylic copolymer.

Manufacturing example  6: Preparation of monomer-containing acrylic copolymer of formula (1)

An acrylic copolymer having a weight average molecular weight of about 1,600,000 was prepared in the same manner as in Preparation Example 2, except that the monomer (A-3) of the formula (1) was used instead of the monomer (A-1)

compare Manufacturing example  1: Preparation of acrylic copolymer

88 parts by weight of n-butyl acrylate (BA), 10 parts by weight of methyl acrylate (MA), 2 parts by weight of 2-hydroxylethyl acrylate (2 parts by weight), and the like were charged in a 1 L reactor equipped with a cooling device, -HEA) and 1 part by weight of acrylic acid (AA), and the mixture was stirred for one hour in ethyl acetate 100 parts by weight. Nitrogen gas was then purged for 1 hour to remove oxygen and then maintained at 62 占 폚. After the mixture was homogenized, 0.07 part by weight of azobisisobutyronitrile (AIBN) as a reaction initiator was added and reacted for 8 hours to prepare an acrylic copolymer having a weight average molecular weight of about 1,600,000.

compare Manufacturing example  2: Preparation of acrylic copolymer

An acrylic copolymer having a weight average molecular weight of about 1,600,000 was prepared in the same manner as in Preparation Example 1, except that 4-hydroxybutyl acrylate (4-HBA) was used instead of the monomer (A-1) Respectively.

compare Manufacturing example  3: Preparation of acrylic copolymer

An acrylic copolymer having a weight average molecular weight of about 1,4500 was prepared in the same manner as in Preparation Example 1, except that methoxyethylene glycol acrylate (MEA) was used instead of the monomer (A-1)

compare Manufacturing example  4: Preparation of acrylic copolymer

Except that 3 parts by weight of 4-hydroxybutyl acrylate (4-HBA) and 3 parts by weight of methoxyethylene glycol acrylate (MEA) were used in place of the monomer (A-1) An acrylic copolymer having a weight average molecular weight of about 1,4500 was prepared in the same manner.

Example  1 to 7 and Comparative Example  1 to 6: Preparation of polarizer with adhesive

Each component was mixed with the composition shown in Table 1 below (unit: parts by weight) and diluted with ethyl acetate to prepare a pressure-sensitive adhesive composition having a solid content concentration of 28%.

The pressure-sensitive adhesive composition prepared above was coated on a releasing film coated with silicone release agent to a thickness of 20 탆 and dried at 100 캜 for 1 minute to form a pressure-sensitive adhesive layer.

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

The prepared polarizing plate was stored for a curing period under the conditions of 23 캜 and 60% RH.

division Acrylic copolymer
(100 parts by weight) Cross-linking agent Antistatic agent B-1 B-2 Example 1 Production Example 1 0.3 1.5 Example 2 Production Example 2 0.3 1.5 Example 3 Production Example 3 0.3 1.5 Example 4 Production Example 4 0.3 1.5 Example 5 Production Example 5 0.3 1.5 Example 6 Production Example 6 0.3 1.5 Example 7 Production Example 1 0.3 1.5 Comparative Example 1 Comparative Preparation Example 1 0.3 1.5 Comparative Example 2 Comparative Production Example 2 0.3 1.5 Comparative Example 3 Comparative Production Example 3 0.3 1.5 Comparative Example 4 Comparative Production Example 2 0.3 1.5 Comparative Example 5 Comparative Production Example 3 0.3 1.5 Comparative Example 6 Comparative Production Example 4 0.3 1.5

Crosslinking agent (B-1): Coronate-L (Japan Urethane Co., Ltd.)

Crosslinking agent (B-2): D110N (Mitsui Chemicals, Japan)

Antistatic agent: 1-octyl-4-methylpyridinium hexafluorophosphate

Experimental Example : Evaluation of physical properties of pressure-sensitive adhesive composition

The physical properties of 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) Durability (heat resistance, Wet heat )

The prepared polarizer with a pressure-sensitive adhesive was cut into a size of 90 mm x 170 mm, the release film was peeled off, and the optical absorption axis was perpendicularly attached to both sides of a glass substrate (110 mm x 190 mm x 0.7 mm). At this time, the applied pressure was 5 kg / cm 2, and a clean room operation was performed so that bubbles or foreign matter would not be generated.

The heat resistance characteristics were evaluated by observing the occurrence of bubbles or peeling after being left at a temperature of 90 ° C. for 1000 hours. The moisture resistance characteristics were measured after being left at a temperature of 70 ° C. and a temperature of 90% RH for 1000 hours Respectively. At this time, the sample was allowed to stand at room temperature for 24 hours immediately before evaluating the state of the specimen.

<Evaluation Criteria>

Ⓞ: No bubbles or peeling.

○: Bubbles or peeling <5

?: 5 pieces? Bubbles or peeling <10 pieces

X: 10 pieces &lt; bubble &

(2) Re-workability

The prepared polarizer with a pressure-sensitive adhesive was cut to a size of 25 mm x 100 mm, the release film was peeled off, and the glass substrate (# 1737, Corning) was laminated at a pressure of 0.25 MPa. Lt; RTI ID = 0.0 &gt; C, &lt; / RTI &gt;

The specimens were put in an oven at 80 ° C, which was a heat-resistant condition, and taken out after 10 hours, they were left at room temperature for 120 hours and then peeled at a rate of 1.3 cm / s.

<Evaluation Criteria>

?: No peeling of the adhesive agent on the glass substrate and clear separation without tearing of the polarizing plate

X: Adhesive is left on the glass substrate or tearing of the polarizer during peeling:

(3) Antistatic property Surface resistivity , Ω / □)

After the release film of the produced polarizer with a pressure-sensitive adhesive was peeled off, the pressure-sensitive adhesive layer of the polarizing plate was peeled off using a surface resistance meter (MCP-HT450, Mitsubishi Chemical), a probe (URS, UR100), and a probe checker The surface resistivity was measured 10 times at each of the three points, and the average value was expressed (unit: Ω / □).

division durability Re-workability Surface resistivity
(Ω / □)
Heat resistance Wet heat Example 1 ◎ ◎ ○ 7.2 × 10 ¹⁰ Example 2 ◎ ○ ○ 9.5 × 10 ¹⁰ Example 3 ○ ◎ ○ 6.0 × 10 ¹⁰ Example 4 ○ ◎ ○ 8.1 × 10 ¹⁰ Example 5 ○ ◎ ○ 6.5 × 10 ¹⁰ Example 6 ◎ ○ ○ 8.2 × 10 ¹⁰ Example 7 ○ ◎ ○ 7.0 × 10 ¹⁰ Comparative Example 1 ○ × × 1.9 × 10 ¹⁰ Comparative Example 2 ○ ○ × 1.6 × 10 ¹⁰ Comparative Example 3 × ○ × 6.9 × 10 ¹⁰ Comparative Example 4 ○ × × 2.2 × 10 ¹¹ Comparative Example 5 × ○ × 7.3 × 10 ¹⁰ Comparative Example 6 × ○ × 9.8 × 10 ¹⁰

As shown in Table 2, the pressure-sensitive adhesive compositions of Examples 1 to 7 using the acrylic copolymer containing the monomer of Formula 1 having a hydroxyl group and an ethylene glycol group according to the present invention were prepared in the same manner as in Comparative Example 1 Sensitive adhesive composition of the present invention exhibited excellent durability and reworkability as well as antistatic property.

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 invention. Do. It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims.

Accordingly, the actual scope of the invention is defined by the appended claims and their equivalents.

Claims (8)

1. A pressure-sensitive adhesive composition comprising a monomer of the following formula (1), an acrylic copolymer containing a (meth) acrylate monomer having an alkyl group of 1-12 carbon atoms and a polymerizable monomer having a crosslinkable functional group, and a crosslinking agent, 0.1 to 20% by weight based on 100% by weight of the total monomers used in the preparation of the acrylic copolymer.
[Chemical Formula 1]

In the above formulas,
n is an integer of 0 to 10,
R is an alkyl group of hydrogen or C ₁ -C _6. The method according to claim 1,
n is an integer of 0 to 5,
And R is hydrogen or methyl. delete delete The pressure-sensitive adhesive composition according to claim 1, wherein the pressure-sensitive adhesive composition further comprises an antistatic agent. The pressure-sensitive adhesive composition according to claim 5, wherein the content of the antistatic agent is 0.1 to 4 parts by weight relative to 100 parts by weight of the acrylic copolymer. A polarizing plate comprising a pressure-sensitive adhesive layer comprising the pressure-sensitive adhesive composition according to any one of claims 1, 2, 5, and 6. A liquid crystal display device comprising the liquid crystal cell according to claim 7 on at least one surface thereof.