KR20110089908A - Adhesive composition and polarizing plate comprising the same - Google Patents

Abstract

PURPOSE: An adhesive composition is provided to ensure reliable durability and reworkability and to improve the change in the condition of a high temperature or high temperature and high humidity condition. CONSTITUTION: An adhesive composition comprises an organic silane compound represented by chemical formula 1. In chemical formula 1, n is the integer of 1~3; R1 is independently a C2~5 aliphatic hydrocarbon group; R2 and R3 are a methyl group or ethyl group; X is an amine group, alkylamine group, or hetero atom; Y is a methoxy group, ethoxy group, dimethylamine group, diethylamine group, halogen element or functional group represented by chemical formula 1-a; m is the integer of 1~3; R4 is independently a C2~5 aliphatic hydrocarbon group; R5 and R6 are a methyl group or ethyl group; and Z is an amine group, alkylamine group or heteroelement.

Description

Adhesive composition and polarizing plate containing same TECHNICAL FIELD

The present invention has excellent reliability and durability, and at the same time improves the change over time in high temperature or high temperature and high humidity conditions, and does not excessively increase the adhesive force so that the reworking property can be re-peeled without leaving the adhesive on the substrate, and the same. It relates to a polarizing plate to include.

In general, a liquid crystal display device (LCD) is formed on an adhesive layer or an adhesive layer based on a liquid crystal cell composed of a transparent glass plate or a plastic plate-like material including a liquid crystal layer and a transparent electrode layer which are arranged in a constant manner. It includes a polarizing plate incorporated by. In addition, a retardation plate, a wide viewing angle compensation plate, a brightness enhancement film, and the like are further included to improve the function of the liquid crystal display.

In addition, the polarizing plate is a polyvinyl alcohol (PVA) polarizer (or 'polarizing film') that is stretched in a predetermined direction and the iodine-based compound or dichroic polarizing material is adsorbed and oriented to protect both sides of the polarizer. It includes a polarizer protective film laminated in order to. Specifically, one side of the polarizer is provided with a polarizer protective film such as triacetyl cellulose (TAC), and an adhesive layer and a release film to be bonded to the liquid crystal cell on the protective film in turn, and on the other side The polarizer protective film and the surface protective film are composed of multiple layers stacked in this order.

The pressure-sensitive adhesive for bonding the polarizing plate to the liquid crystal cell generally requires physical properties such as heat resistance, moisture heat resistance, rework resistance, and light leakage resistance, among which in particular, in order to satisfy durability and rework resistance such as heat resistance or moisture resistance. Since the properties of the pressure-sensitive adhesives are mutually conflicting, satisfying all of them has not been completely solved. For example, durability is improved when the peeling force between the glass plate and the pressure-sensitive adhesive is high, while reworkability is improved as the peeling force on the glass is low. As such, it is difficult to satisfy two types of physical properties at the same time.

Korean Patent No. 840114 discloses a pressure-sensitive adhesive composition comprising a silane compound containing a cyanoacetyl group. This technique has a problem in that durability and reworkability are improved to a certain degree by a silane compound, but the reworkability required by a large panel is not provided by cyanoacetyl groups.

The present invention includes a malonyl group-containing organic silane compound has excellent reliability durability, and the pressure-sensitive adhesive composition that can be reworked to improve the rework without leaving an adhesive on the substrate is not excessively increased according to time and temperature The purpose is to provide.

Another object of the present invention is to provide a pressure-sensitive adhesive composition which is improved over time in high temperature or high temperature and high humidity conditions.

Another object of the present invention is to provide a polarizing plate in which an adhesive layer made of the adhesive composition is laminated.

1.A pressure-sensitive adhesive composition comprising an organosilane compound represented by the following formula (1):

이며, m은 1~3인 정수이며; R₄는 각각 독립적으로 탄소수 2~5의 지방족 탄화수소기이고; R₅ 및 R₆은 메틸기 또는 에틸기이며; Z는 아민기, 알킬아민기 또는 헤테로 원소임).(Wherein n is an integer of 1 to 3; R ₁ is each independently an aliphatic hydrocarbon group having 2 to 5 carbon atoms; R ₂ and R ₃ are a methyl group or an ethyl group; X is an amine group, an alkylamine group, or a hetero group) Y is a methoxy group, ethoxy group, dimethylamine group, diethylamine group, halogen element or

M is an integer of 1 to 3; Each R ₄ is independently an aliphatic hydrocarbon group having 2 to 5 carbon atoms; R ₅ and R ₆ are a methyl group or an ethyl group; Z is an amine group, an alkylamine group or a hetero element.

2. according to the above 1, wherein the organic silane compound is represented by the following formula 2 pressure-sensitive adhesive composition:

3. In the above 1, wherein the organic silane compound is represented by the following formula 3 pressure-sensitive adhesive composition:

4. In the above 1, wherein the organic silane compound is represented by the following formula 4 pressure-sensitive adhesive composition:

5. In the above 1, the organic silane compound is a pressure-sensitive adhesive composition represented by the following formula (5):

6. In the above 1, the organic silane compound represented by Formula 1 is included in the pressure-sensitive adhesive composition 0.01 to 5 parts by weight based on 100 parts by weight of the pressure-sensitive adhesive resin (solids content).

7. In the above 6, the organic silane compound represented by Formula 1 is included in the pressure-sensitive adhesive composition 0.1 to 4 parts by weight based on 100 parts by weight of the pressure-sensitive adhesive resin (solid content).

8. In the above 6, the pressure-sensitive adhesive composition containing 0.1 to 15 parts by weight of the crosslinking agent based on 100 parts by weight of the pressure-sensitive adhesive resin (solids content).

9. In the above 6, the pressure-sensitive adhesive resin is 80 to 99% by weight of an alkyl (meth) acrylate monomer having 4 to 12 carbon atoms; 1 to 10% by weight of at least one polymerizable monomer selected from carboxylic acid group, hydroxyl group, amide group and tertiary amine group; And 0-10% by weight of other monomers.

10. Polarizing plate in which the pressure-sensitive adhesive layer made of the composition of any one of claims 1 to 9 is laminated on one surface.

The pressure-sensitive adhesive composition of the present invention includes a malonyl group-containing organic silane compound, and has excellent reliability and durability, and does not excessively increase the adhesive strength with time and temperature.

In particular, the pressure-sensitive adhesive composition of the present invention can be re-peeled without leaving the pressure-sensitive adhesive on the substrate because the adhesive force does not excessively increase even under high temperature or high temperature and high humidity conditions.

The pressure-sensitive adhesive composition of the present invention has little change over time in high temperature or high temperature and high humidity conditions, and is excellent in substrate and initial adhesive strength.

The present invention has excellent reliability and durability by using a malonyl group-containing organic silane compound, and at the same time, it is possible to re-peel without leaving an adhesive on the substrate because not only the aging change is improved in high temperature or high temperature and high humidity conditions but the adhesive force is not excessively increased. The present invention relates to an adhesive composition having improved reworkability and a polarizing plate including the same.

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

The pressure-sensitive adhesive composition of the present invention includes an organosilane compound represented by the formula (1) containing a malonyl group, and may include other pressure-sensitive adhesive resins and crosslinking agents.

[Formula 1]

이다. 이때 m은 1~3인 정수이며; R₄는 각각 독립적으로 탄소수 2~5의 지방족 탄화수소기이고; R₅ 및 R₆은 메틸기 또는 에틸기이며; Z는 아민기, 알킬아민기 또는 헤테로 원소이다.In the formula, n is an integer of 1 to 3; Each R ₁ is independently an aliphatic hydrocarbon group having 2 to 5 carbon atoms; R ₂ and R ₃ are a methyl group or an ethyl group; X is an amine group, an alkylamine group or a hetero element; Y is a methoxy group, ethoxy group, dimethylamine group, diethylamine group, halogen element or

to be. M is an integer of 1 to 3; Each R ₄ is independently an aliphatic hydrocarbon group having 2 to 5 carbon atoms; R ₅ and R ₆ are a methyl group or an ethyl group; Z is an amine group, an alkylamine group or a hetero element.

Examples of the hetero element include sulfur (S) and oxygen (O), and examples of the halogen element include fluorine, chlorine, boron, and iodine.

The organosilane compound is prepared at a temperature of 10 to 200 ° C, preferably 50 to 150 ° C, under a chloroplatinic acid catalyst and an organic solvent. Examples of the organic solvent include halogenated alkyl solvents such as chloroform, methylene chloride, dichloroethane and the like; Cyclic ether solvents such as tetrahydrofuran, dioxin and the like; Aromatic organic solvent, such as benzene, toluene, xylene, etc. are mentioned.

Since the malonyl group-containing organic silane compound represented by the formula (1) controls the reactivity by adjusting the element of the alpha position of the malonyl group, it is possible to satisfy rework and reliability durability at the same time.

인 화합물이 바람직하다. 이때, m은 3, R₄는 프로필렌기, R₅는 메틸기, Z는 아민기인 화합물이 바람직하다.N is 3, R ₁ is a propylene group, R ₂ is a methyl group or an ethyl group, X is an amine group or a methylamine group, Y is an ethoxy group,

Phosphorus compounds are preferred. In this case, a compound in which m is 3, R ₄ is a propylene group, R ₅ is a methyl group, and Z is an amine group is preferable.

The organic silane compound represented by the formula (1) is preferably 0.01 to 5 parts by weight, preferably 0.1 to 4 parts by weight, most preferably 0.5 to 4 parts by weight based on 100 parts by weight of the pressure-sensitive adhesive resin (based on the solid content). If the content is less than 0.01 parts by weight, the effect of increasing the adhesive strength at high temperature and high humidity may be insignificant. If the content is more than 5 parts by weight, bubbles are formed between the substrate and peeling occurs, thereby reducing reliability durability. Can be.

The pressure-sensitive adhesive resin is a resin having an adhesive force that can act as an adhesive, and specific examples thereof include an acrylic copolymer, natural rubber, styrene-isoprene-styrene (SIS) block copolymer, styrene-butadiene-styrene (SBS) block copolymer, and styrene- Common polymers such as ethylene butylene-styrene (SEBS) block copolymer, styrene-butadiene rubber, polybutadiene, polyisoprene, polyisobutylene, butyl rubber, chloroprene rubber, silicone rubber, and the like. Copolymers can be used.

As the acrylic copolymer, an alkyl (meth) acrylate copolymer composed of an alkyl (meth) acrylate monomer having 4 to 12 carbon atoms, a polymerizable monomer having a crosslinkable functional group, and other monomers can be used. In this case, (meth) acrylate means both acrylate and methacrylate.

Specific examples of the alkyl (meth) methacrylate monomer having 4 to 12 carbon atoms include (meth) acrylates derived from aliphatic alcohols having 4 to 12 carbon atoms, such as n-butyl (meth) acrylate and 2-butyl (meth) acryl. Late, t-butyl (meth) acrylate, pentyl (meth) acrylate, octyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, Usyl (meth) acrylate etc. can be mentioned, These can be used individually or in mixture of 2 or more types. Among them, n-butyl acrylate, 2-ethylhexyl acrylate or a mixture thereof may be preferably used.

The alkyl (meth) methacrylate monomer having 4 to 12 carbon atoms is included in an amount of 80 to 99% by weight, preferably 90 to 95% by weight, based on 100% by weight of the pressure-sensitive adhesive resin (based on the solid content). If the content is less than 80% by weight, the adhesion may be lowered, and if the content is more than 99% by weight, the cohesion may be lowered.

The polymerizable monomer having a crosslinkable functional group reacts with a crosslinking agent to impart cohesion force or adhesive strength by chemical bonding so that cohesive force destruction of the pressure sensitive adhesive does not occur under high temperature or high humidity conditions. The polymerizable monomer which has a hydroxyl group, the polymerizable monomer which has an amide group, the polymerizable monomer which has a tertiary amine group, etc. are mentioned.

Examples of the 'polymerizable monomer having a carboxylic acid group include monovalent acids such as (meth) acrylic acid and crotonic acid; Monoalkyl esters of diacids and diacids, such as maleic acid, itaconic acid and fumaric acid; 3- (meth) acryloylpropionic acid; Succinic anhydride ring-opening adduct to 2-hydroxyalkyl (2 to 3 carbon) (meth) acrylate, Succinic anhydride ring opening adduct to polyoxyalkylene (2 to 4) glycol mono (meth) acrylate, 2 The compound etc. which ring-opened and added amber acid anhydride to the caprolactone adduct to -hydroxyalkyl (C2-C3) (meth) acrylate are mentioned, Among these, acrylic acid is preferable.

In addition, examples of the polymerizable monomer having a hydroxyl group include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, and polyoxyalkylene (C2-4) glycol mono (meth) acrylate etc. are mentioned, It is preferable to use 2-hydroxyethyl (meth) acrylate among these.

In addition, examples of the polymerizable monomer having an amide group include (meth) acrylamide, N-isopropylacrylamide, N-tert-butylacrylamide, and among these, it is preferable to use (meth) acrylamide. .

In addition, examples of the polymerizable monomer having a tertiary amine group include N, N-dimethylaminoethyl (meth) acrylate, N, N-diethylaminoethyl methacrylate, N, N-dimethylaminopropyl acrylate, and the like. Can be.

The polymerizable monomer having a crosslinkable functional group is included in an amount of 1 to 10% by weight, preferably 1 to 5% by weight, based on 100% by weight of the pressure-sensitive adhesive resin (based on the solid content). When the content is less than 1% by weight, cohesion may be lowered, and when it is more than 10% by weight, cohesiveness may be lowered.

In addition, other monomers are included in an amount of 0 to 10% by weight, preferably 0 to 5% by weight, based on 100% by weight of the pressure-sensitive adhesive resin (based on the solid content). When the content is more than 10% by weight, the adhesive force of the pressure-sensitive adhesive composition may be lowered. "0" in the content indicates that the component is not included.

The acrylic copolymer has a weight average molecular weight (polystyrene equivalent) measured by gel permeation chromatography (GPC) is usually 50,000 to 2,000,000, preferably 100,000 to 1,800,000, more preferably 500,000 to 1,500,000 It is good.

The crosslinking agent is used to reinforce the cohesive force of the pressure-sensitive adhesive by appropriately crosslinking the acrylic copolymer, and an isocyanate compound, an epoxy compound, a melamine resin, an aziridine compound, or the like may be used. Preferably, an isocyanate compound or melamine resin is used. Can be. These can be used individually or in combination of 2 or more types. In particular, it is also possible to add a melamine resin to the isocyanate compound.

Examples of the isocyanate compound include diisocyanate compounds such as toluene diisocyanate, xylene diisocyanate, hexamethylene diisocyanate, 2,4-diphenylmethane diisocyanate, 4,4-diphenylmethane diisocyanate, and trimethylol of diisocyanate. Additives to polyhydric alcohol compounds such as propane and the like can be used.

As the melamine resin, polyepoxy compounds such as hexamethylol melamine, hexamethoxymethylmelamine, hexabutoxymethylmelamine, bisphenol A and epichlorohydrin condensate-type epoxy compounds, and polyglycidyl of polyoxyalkylene polyols Ethers, glycerin diglycidyl ether, glycerin triglycidyl ether, tetraglycidyl xylenediamine and the like can be used.

The crosslinking agent is included in an amount of 0.1 to 15 parts by weight, preferably 1 to 5 parts by weight, based on 100 parts by weight of the adhesive resin (based on the solid content). If the content is less than 0.1 part by weight, the cohesive strength may be reduced due to insufficient crosslinking degree, thereby impairing the properties such as reliability, durability, and cutting properties. If the content is more than 15 parts by weight, problems may occur in reducing residual stress due to excessive crosslinking reaction. .

The pressure-sensitive adhesive composition comprising the above components is a tackifying resin, antioxidant, corrosion inhibitor, leveling agent, surface in order to adjust the adhesion, cohesion, viscosity, elastic modulus, glass transition temperature, antistatic properties, etc. required according to the application Additives such as lubricants, dyes, pigments, antifoams, fillers, light stabilizers, antistatic agents and the like may be further included.

The adhesive composition of this invention can be used as an adhesive for polarizing plates or a surface protection film. In addition, it can be used as a protective film, a reflective sheet, a structural adhesive sheet, a photo adhesive sheet, a lane display adhesive sheet, an optical adhesive product, an adhesive for an electronic component, as well as a general commercial adhesive sheet product and a medical patch.

Polarizing plate of the present invention is characterized in that the pressure-sensitive adhesive layer made of the pressure-sensitive adhesive composition is laminated.

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

Such a polarizing plate can be applied to all conventional liquid crystal display devices, and specifically, a liquid crystal display device including a liquid crystal panel in which a polarizing plate on which an adhesive layer is laminated is bonded to at least one surface of a liquid crystal cell can be configured.

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.

[Example]

Synthesis Example 1 Synthesis of Compound of Formula 2

Into a 1 liter reactor equipped with a thermometer and a condenser, 200 ml of tetrahydrofuran (THF), 40 g (0.25 mol) of 3-malonic diethyl ester, 45 g (0.25 mol) of aminopropyltrimethoxysilane were added and the temperature was raised to 60 ° C. After the addition, 0.05 g of chloroplatinic acid was added and reacted for 4 hours. After the completion of the reaction, the solvent and the unreacted substance were removed and vacuum distilled to obtain 73 g of Chemical Formula 2.

[Formula 2]

Synthesis Example 2 Synthesis of Compound of Formula 3

200 ml of tetrahydrofuran (THF), 40 g (0.25 mol) of 3-malonic diethyl ester, 90 g (0.5 mol) of aminopropyltriethoxysilane were added to a 1 L reactor equipped with a thermometer and a condenser. After the addition, 0.05 g of chloroplatinic acid was added and reacted for 4 hours. After the reaction was completed, the solvent and the unreacted substance were removed, and vacuum distillation yielded 65 g of Chemical Formula 3.

(3)

Synthesis Example 3 Synthesis of Compound of Formula 4

200 ml of tetrahydrofuran (THF), 40 g (0.25 mol) of 3-malonic diethyl ester, 90 g (0.5 mol) of methylaminopropyltrimethoxysilane were added to a 1 L reactor equipped with a thermometer and a condenser. After the addition, the reaction was performed for 4 hours by adding 0.05 g of chloroplatinic acid. After completion of the reaction, the solvent and the unreacted substance were removed, and vacuum distillation yielded 68 g of Chemical Formula 4.

[Formula 4]

Synthesis Example 4 Synthesis of Compound of Formula 5

200 ml of tetrahydrofuran (THF), 40 g (0.25 mol) of 3-malonic diethyl ester, 90 g (0.5 mol) of methylaminopropyltrimethoxysilane were added to a 1 L reactor equipped with a thermometer and a condenser. After the addition, the reaction was performed for 4 hours by adding 0.1 g of chloroplatinic acid. After completion of the reaction, the solvent and the unreacted substance were removed and vacuum distilled to obtain 86 g of Chemical Formula 5.

[Chemical Formula 5]

Preparation Example: Preparation of Acrylic Copolymer

98.1 parts by weight of n-butyl acrylate (BA), 1.4 parts by weight of acrylic acid (AA), 2-hydroxyethyl methacrylate (2-HEMA) in a 1 L reactor equipped with a refrigeration system for easy reflux of nitrogen gas ) 0.5 parts by weight of 100 parts by weight of ethyl acetate (EAc) was added as a solvent. Thereafter, nitrogen gas was purged for 1 hour to remove oxygen, and kept at 62 ° C. After homogenizing the mixture, 0.07 parts by weight of azobisisobutyronitrile (AIBN) was added as a reaction initiator, and reacted for 8 hours to prepare an acrylic copolymer having a weight average molecular weight of 600,000 or more.

Example 1

0.5 parts by weight of toluene diisocyanate (TMP-TDI) of trimethylolpropane (TMP-TDI) was added as a crosslinking agent with respect to 100 parts by weight of the acrylic copolymer (based on the solid content) of Preparation Example 1 The mixture was diluted with and then mixed uniformly to prepare an adhesive composition.

The pressure-sensitive adhesive composition was applied to a PET film (41 cm x 34 cm) coated with a silicone release agent to have a dry film thickness of 25 μm, and dried at 100 ° C. for 1 minute to form an adhesive layer. An adhesive sheet was prepared by laminating another release film thereon.

Example 2

It carried out in the same manner as in Example 1, to prepare a pressure-sensitive adhesive composition with a content of the formula (2) to 3 parts by weight.

Example 3

The same procedure as in Example 1 was carried out, but the pressure-sensitive adhesive composition was prepared using 3 parts by weight of Formula 3 instead of Formula 2.

Example 4

The same procedure as in Example 1 was carried out, but the pressure-sensitive adhesive composition was prepared using 3 parts by weight of Formula 4 instead of Formula 2.

Example 5

The same procedure as in Example 1 was carried out, but the pressure-sensitive adhesive composition was prepared using 3 parts by weight of the formula (5) instead of the formula (2).

Comparative Example 1

In the same manner as in Example 1, using an organic silane compound 3-glycidoxypropyltrimethoxysilane (3-glycidoxypropyltrimethoxysilane, KBM-403, Shin-Etsu Corp.) to 1 part by weight to prepare a pressure-sensitive adhesive composition.

Comparative Example 2

In the same manner as in Example 1, an adhesive composition was prepared using 3-glycidoxypropyltrimethoxysilane (KBM-403, Shin-Etsu Corp.) as 3 parts by weight of an organic silane compound.

Comparative Example 3

In the same manner as in Example 1, but instead of the organic silane compound, an adhesive composition was prepared using 3-aminopropyltrimethoxysilane (3-aminopropyltrimethoxysilane, KBM-903, Shin-Etsu Co., Ltd.) as 3 parts by weight.

The components of the pressure-sensitive adhesive composition prepared in Examples and Comparative Examples and their contents are shown in Table 1 below. At this time, the content of each component represents parts by weight.

division Organosilane compounds Formula 2 (3) Formula 4 Formula 5 KBM403 KBM903 Example 1 One - - - - - Example 2 3 - - - - - Example 3 - 3 - - - - Example 4 - - 3 - - - Example 5 - - - 3 - - Comparative Example 1 - - - - One - Comparative Example 2 - - - - 3 - Comparative Example 3 - - - - - 3

Test Example

1. Measurement of adhesion

In the adhesive sheets of Examples 1 to 5 and Comparative Examples 1 to 3, the release film was peeled off and bonded to the polarizing plate, thereby preparing a polarizing plate in which the adhesive layer was laminated.

The polarizing plate thus produced was cut out to a size of 25 mm in width and 100 mm in length, the release film was peeled off, and laminated on a glass plate at a pressure of 0.25 MPa to prepare an evaluation sample. The laminated samples were left for 24 hours in an environment of 23 ° C. and 50% RH after autoclave treatment of 5 kg / cm 2 × 20 minutes at a temperature of 50 ° C. and for 48 hours in an environment of 50 ° C. and 50% RH. The adhesive force at the time of peeling at a peel rate of 10 m / min and a peel angle of 180 ° was measured using UTM (Universal Tensile Testing Machine, Instron). The measurement was performed at 23 degreeC and 50% RH environment.

2. Reworkability Measurement

The pressure-sensitive adhesive layer is cut into 25 mm in width and 100 mm in length, and the release film is peeled off. After laminating to Corning's # 1737 glass at a pressure of 0.25 MPa, autoclave is carried out at 5 atmospheres and 50 ° C. for 20 minutes. Was processed to prepare an evaluation sample. After putting it in the oven at 80 ℃ for heat condition and taking it out after 10 hours, it was left at room temperature for 120 hours and then peeled off at a speed of 1.3cm / s. It peeled at the speed of 1.3 cm / s.

-In both conditions, there is no adhesive left on the glass substrate and peeling off without tearing of the polarizing plate: ○

The adhesive remains on the panel under more than one condition or the polarizer is torn during the peeling process: ×

3. Reliability and Durability

The polarizing plate on which the pressure-sensitive adhesive layer was laminated was cut into a width of 90 mm and a length of 170 mm and attached to both surfaces of the glass substrate (110 mm X 190 mm X 0.7 mm) with the optical absorption axis crossed. At this time, the pressure applied was 5kg / cm ² and clean room work was performed to prevent bubbles or foreign substances from being generated. In order to determine the heat and humidity resistance of the samples, the resultant was observed for 1,000 hours at a temperature of 60 ° C. and a relative humidity of 90%, and then bubbles or peelings were observed. The heat resistance was observed for 1,000 hours at the temperature of 80 ℃ after the occurrence of bubbles or peeling. Immediately after evaluating the state of the sample, it was left to stand at room temperature for 24 hours. In addition, after the samples prepared above were left for 5 months or more to evaluate the reliability by the above method. The evaluation criteria for reliability are as follows.

<Evaluation Criteria>

Ⓞ: no bubbles or peeling

○: less than 5 bubbles or peeling

(Triangle | delta): Five or more bubbles and peelings are less than ten

×: 10 or more bubbles or peelings

division trust
durability Adhesion (N / 25㎜) Reworkability 23 ℃, 24 hours 50 ° C, 48 hours 80 ° C, 10 hours 60 ° C, 90% RH,
12 hours Example 1 ○ 1.5 3.5 ○ ○ Example 2 Ⓞ 2.0 4.2 ○ ○ Example 3 ○ 1.8 3.3 ○ ○ Example 4 ○ 2.1 3.8 ○ ○ Example 5 Ⓞ 2.2 5.4 ○ ○ Comparative Example 1 ○ 1.6 8.9 × × Comparative Example 2 Ⓞ 2.2 10.4 × × Comparative Example 3 △ 2.0 6.7 × ×

As shown in the above table, the pressure-sensitive adhesive composition of Examples 1 to 5 comprising the organic silane compound represented by Formula 1 according to the present invention is compared to Comparative Examples 1 to 3 including the conventional silane coupling agent according to time and temperature It did not excessively increase, and it was confirmed that re-peelability was possible without leaving an adhesive on the substrate because the reworkability was excellent under high temperature or high temperature and high humidity conditions. It was also confirmed that excellent durability was maintained.

Claims (10)

Pressure-sensitive adhesive composition comprising an organosilane compound represented by the following formula (1):
[Formula 1]

(Wherein n is an integer of 1 to 3; R ₁ is each independently an aliphatic hydrocarbon group having 2 to 5 carbon atoms; R ₂ and R ₃ are a methyl group or an ethyl group; X is an amine group, an alkylamine group, or a hetero group) Y is a methoxy group, ethoxy group, dimethylamine group, diethylamine group, halogen element or

M is an integer of 1 to 3; Each R ₄ is independently an aliphatic hydrocarbon group having 2 to 5 carbon atoms; R ₅ and R ₆ are a methyl group or an ethyl group; Z is an amine group, an alkylamine group or a hetero element.
The pressure-sensitive adhesive composition of claim 1, wherein the organosilane compound is represented by the following Chemical Formula 2:
(2)

.
The pressure-sensitive adhesive composition of claim 1, wherein the organosilane compound is represented by the following Chemical Formula 3:
(3)

.
The pressure-sensitive adhesive composition of claim 1, wherein the organosilane compound is represented by the following Chemical Formula 4:
[Chemical Formula 4]

.
The pressure-sensitive adhesive composition of claim 1, wherein the organosilane compound is represented by the following Formula 5:
[Chemical Formula 5]

.
The pressure-sensitive adhesive composition of claim 1, wherein the organic silane compound represented by Formula 1 is included in an amount of 0.01 to 5 parts by weight based on 100 parts by weight of the pressure-sensitive adhesive resin (based on the solid content).
The pressure-sensitive adhesive composition of claim 6, wherein the organic silane compound represented by Formula 1 is included in an amount of 0.1 to 4 parts by weight based on 100 parts by weight of the pressure-sensitive adhesive resin (based on the solid content).
The pressure-sensitive adhesive composition of claim 6, wherein the crosslinking agent is included in an amount of 0.1 to 15 parts by weight based on 100 parts by weight of the pressure-sensitive adhesive resin (based on the solid content).
The pressure-sensitive adhesive resin of claim 6, wherein the pressure-sensitive adhesive resin has 80 to 99% by weight of an alkyl (meth) acrylate monomer having 4 to 12 carbon atoms; 1 to 10% by weight of at least one polymerizable monomer selected from carboxylic acid group, hydroxyl group, amide group and tertiary amine group; And 0-10% by weight of other monomers.
The polarizing plate in which the adhesive layer which consists of a composition of any one of Claims 1-9 was laminated on one side.