WO2015156517A1 - Antistatic adhesive composition and polarizing plate manufactured using same - Google Patents

Abstract

The present invention relates to an antistatic adhesive composition and a polarizing plate manufactured using the same and, more specifically, to an antistatic adhesive composition and a polarizing plate manufactured using the same, wherein the antistatic adhesive composition can exhibit excellent antistatic properties and durability by containing an acryl-based copolymer, a cross-linking agent, an antistatic agent, and a polyaminoether compound having two or more tertiary amines and one or more ether groups in one molecule.

Description

Antistatic adhesive composition and polarizing plate manufactured using the same

The present invention relates to an antistatic pressure-sensitive adhesive composition, and more particularly, to an antistatic pressure-sensitive adhesive composition excellent in antistatic properties and durability, and a polarizing plate manufactured using the same.

The image display device is composed of a liquid crystal cell containing a liquid crystal and a polarizing plate, which is mainly bonded by forming an adhesive layer on one surface of the polarizing plate. In addition, a surface protection film such as a retardation plate, a wide viewing angle compensation plate, and brightness enhancement is additionally attached to the polarizing plate through an adhesive or the like to improve the function of the image display device. Optical members such as surface protection films and polarizing plates are used as plastics, so static electricity is generated during friction or peeling. In addition, when a voltage is applied to the liquid crystal in a state where static electricity remains, various orientations of antistatic treatments are performed to prevent such a problem because orientation of liquid crystal molecules may be lost or defects may occur in the panel.

For example, there is a method of adding an antistatic agent composed of a polyether polyol and an alkali metal salt to an acrylic adhesive, but in this case, bleeding of the antistatic agent occurs, so that durability after the curing of the adhesive is significantly reduced, and when applied to a protective film, Bleed-out easily occurs under the conditions, causing a problem in that the adherend is contaminated.

In addition, in the case of adding at least one surfactant to the pressure-sensitive adhesive and transfer the surfactant to the adhesive, the surfactant is easily bleeding on the pressure-sensitive adhesive surface, there was a problem that the adhesive is contaminated when applied to the protective film.

Korean Laid-Open Patent Publication No. 2010-0093470 discloses that an alkylene glycol dialkyl ether compound is included as an adhesive composition in order to increase antistatic property by using an additive having a large interaction with ions in addition to properties sufficient for optical applications. , Korean Laid-Open Patent Publication No. 2012-0132396 discloses that a polyether compound having a reactive silyl group at at least one end thereof is included in a pressure-sensitive adhesive composition for satisfying antistatic properties and durability. However, there has been a problem that the effect of improving the compatibility of the antistatic agent is not sufficient, and thus the durability deterioration due to the bleed out of the antistatic agent is not sufficiently suppressed.

[Preceding technical literature]

[Patent Documents]

(Patent Document 1) Korean Patent Publication No. 2010-0093470

(Patent Document 2) Korean Patent Publication No. 2012-0132396

An object of the present invention is to provide an antistatic adhesive composition which is remarkably excellent in antistatic property and durability.

1. A pressure-sensitive adhesive composition comprising a polyaminoether compound having at least two tertiary amines and at least one ether group, an acrylic copolymer, a crosslinking agent and an antistatic agent in a molecule.

2. In the above 1, wherein the polyamino ether compound having at least two tertiary amines and at least one ether group in the molecule is a compound represented by the following formula (1), pressure-sensitive adhesive composition:

 [Formula 1]

Wherein R ₁ , R ₂ , R ₃ and R ₄ are each independently a substituted or unsubstituted linear or branched C1-C12 alkyl or C6-C12 aryl group having 6 to 12 carbon atoms. R ₁ and R ₂ or R ₃ and R ₄ may be linked to each other to form a hydrocarbon ring, and when n is 2 or more, R ₁ may be changed for each repeating unit, and n is an integer of 1 to 5 ).

3. In the above 2, wherein the compound represented by Formula 1 is at least one selected from the group consisting of Formula 2 to 14, the pressure-sensitive adhesive composition:

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

[Formula 14]

4. according to the above 1, wherein the polyamino ether compound having at least two tertiary amines and at least one ether group in the molecule is contained in 0.1 to 10 parts by weight based on 100 parts by weight of the acrylic copolymer, the pressure-sensitive adhesive composition .

5. The method according to the above 1, wherein the antistatic agent is at least one of bis (fluorosulfonyl) imide potassium (KN (FSO ₂ ) ₂ ) or bis (fluorosulfonyl) imide sodium (NaN (FSO ₂ ) ₂ ) One, adhesive composition.

6. The pressure-sensitive adhesive sheet comprising a pressure-sensitive adhesive layer formed of the pressure-sensitive adhesive composition of any one of 1 to 5 above.

7. At least one surface having a pressure-sensitive adhesive layer formed of the pressure-sensitive adhesive composition of any one of 1 to 5, the polarizing plate.

8. Image display device including the polarizing plate of the above seven.

The polyaminoether compound having at least two tertiary amines and at least one ether group in the molecule according to the present invention has a higher hydrophilicity than the case where the additive used in the prior art is a polyethylene glycol compound, and thus effectively coordinates the antistatic agent to prevent the antistatic agent. Since it is possible to increase the degree of ionization of the pressure-sensitive adhesive composition, the pressure-sensitive adhesive composition of the present invention exhibits excellent antistatic property compared with the conventional pressure-sensitive adhesive composition. In addition, by increasing the coordination force of the antistatic agent it is possible to prevent the bleed out to improve the durability.

The present invention comprises an acrylic copolymer, a crosslinking agent, an antistatic agent and a polyamino ether compound having at least two tertiary amines and at least one ether group in a molecule thereof, thereby providing an antistatic adhesive composition having excellent antistatic property and durability and using the same It relates to a polarizing plate manufactured by.

<Adhesive Composition>

The pressure-sensitive adhesive composition of the present invention includes an acrylic copolymer, a crosslinking agent and an antistatic agent, and a polyaminoether compound having at least two tertiary amines and at least one ether group in the molecule.

Hereinafter, the present invention will be described in detail.

The polyamino ether compound according to the present invention may have more than one of the tertiary amines and one or more ether groups in the molecule, thereby having an antistatic property and durability superior to the prior art.

Specifically, the polyamino ether compound according to the present invention has a specific structure of formula (1), has a high hydrophilicity compared to polyethylene glycol used as an additive in the conventional pressure-sensitive adhesive composition, effectively folds the antistatic agent with a non-covalent electron pair of nitrogen and oxygen For this reason, it is judged that the degree of ionization of the antistatic agent can be increased. Therefore, it is judged that the adhesive composition of this invention can exhibit the outstanding antistatic property. In addition, the polyamino ether compound according to the present invention can immobilize the antistatic agent by increasing the coordination force of the antistatic agent, thereby preventing bleeding out, thereby remarkably improving the durability of the pressure-sensitive adhesive composition.

The polyamino ether compound according to the present invention can be used as long as the compound contains at least two tertiary amines and at least one ether group in the molecule. Preferably, a polyaminoether compound containing two or more tertiary amines and one or more ether groups in the molecule may be represented by the following formula (1).

 [Formula 1]

Wherein R ₁ , R ₂ , R ₃ and R ₄ are each independently a substituted or unsubstituted linear or branched C1-C12 alkyl or C6-C12 aryl group having 6 to 12 carbon atoms. R ₁ and R ₂ or R ₃ and R ₄ may be linked to each other to form a hydrocarbon ring, and when n is 2 or more, R ₁ may be changed for each repeating unit, and n is an integer of 1 to 5 ).

For more specific examples of the compound of Formula 1, the compound of Formula 1 may be a compound of Formula 2 to 14. These can be used individually or in mixture of 2 or more types, respectively.

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

[Formula 10]

[Formula 11]

[Formula 12]

[Formula 13]

[Formula 14]

The content of the polyamino ether compound according to the present invention is not particularly limited. For example, the polyamino ether compound may be included in an amount of 0.1 to 10 parts by weight, preferably 1 to 5 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 durability improvement effect, if more than 10 parts by weight may cause a decrease in durability due to the bleed out of the polyamino ether compound itself.

Acrylic copolymers of the present invention can be used without particular limitation those known in the art.

For example, it may be polymerized including a (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms and a polymerizable monomer having a crosslinkable functional group, wherein the (meth) acrylate may be a acrylate and methacrylate. All means.

As a (meth) acrylate monomer which has a C1-C12 alkyl group, 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, and the like, among which n-butyl acrylate, 2-ethylhexyl acrylate or Mixtures of these are preferred. These can be used individually or in mixture of 2 or more types.

The content and mixing ratio of the (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms is not particularly limited. For example, the content may be 85 to 99.9 parts by weight based on 100 parts by weight of the total monomers, based on solid content. Preferably it is 90 to 95 parts by weight. If the content is less than 85 parts by weight, sufficient adhesion cannot be exerted, and if it exceeds 99.9 parts by weight, the cohesion may be lowered.

The polymerizable monomer having a crosslinkable functional group is a component for reinforcing the cohesive force or adhesive strength of the pressure-sensitive adhesive composition by chemical bonding and imparting durability and cutting property, such as a monomer having a carboxyl group, a monomer having a hydroxy group, a monomer having an amide group, The monomer etc. which have a tertiary amine group are mentioned, These can be used individually or in mixture of 2 or more types, It is preferable not to contain acrylic acid from the viewpoint of corrosion prevention improvement.

As a monomer which has a carboxy group, Monovalent acids, such as (meth) acrylic acid and a crotonic acid; Diacids such as maleic acid, itaconic acid and fumaric acid, and monoalkyl esters thereof; 3- (meth) acryloylpropionic acid; Succinic anhydride ring-opening adduct of 2-hydroxyalkyl (meth) acrylate with 2-3 carbon atoms of an alkyl group, Succinic anhydride ring opening adduct of hydroxyalkylene glycol (meth) acrylate with 2-4 carbon atoms of an alkylene group And a compound obtained by ring-opening addition of succinic anhydride to a caprolactone adduct of 2-hydroxyalkyl (meth) acrylate having 2 or 3 carbon atoms of an alkyl group, and among these, (meth) acrylic acid is preferable.

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, Among these, (meth) acrylamide is preferable.

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 ) Acrylates and the like.

The content and the mixing ratio of the polymerizable monomer having a crosslinkable functional group are not particularly limited. For example, the polymerizable monomer may be included in an amount of 0.1 to 15 parts by weight, and preferably 0.5 to 8 parts by weight based on 100 parts by weight of the total monomers. It is good. If the content is less than 0.1 parts by weight, the cohesive force of the pressure-sensitive adhesive may be lowered, the durability may be lowered. If the content is more than 15 parts by weight, the adhesive strength is lowered and durability may be lowered by a high gel fraction.

The acrylic copolymer may further include a polymerizable monomer known in the art in addition to the above monomers in a range that does not lower the adhesive strength, such as 10 wt% or less of the total weight of the 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 acrylic copolymer preferably has a weight average molecular weight (polystyrene equivalent, Mw) measured by gel permeation chromatography (GPC) of 50,000 to 2 million, more preferably 400,000 to 2 million. If the weight average molecular weight is less than 50,000, there is a lack of cohesion between the copolymers may cause problems in adhesion durability, if the weight average molecular weight is more than 2 million may require a large amount of dilution solvent to ensure fairness during coating.

The crosslinking agent is a component for improving the cohesion force by appropriately crosslinking the copolymer, and the kind thereof is not particularly limited. For example, an isocyanate type, an epoxy type, or the like may be used, and these may be used alone or in combination of two or more thereof.

Isocyanate type crosslinking agent specifically, tolylene diisocyanate, xylene diisocyanate, 2, 4- diphenylmethane diisocyanate, 4, 4- diphenylmethane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, tetramethylene xylene diisocyanate, Diisocyanate compounds such as naphthalene diisocyanate, adducts of polyhydric alcohol-based compounds such as diisocyanate and trimethanol propane, isocyanurates obtained by self-condensing diisocyanates, biuret bodies condensed with diisocyanates in diisocyanate urea, and tri The polyfunctional isocyanate compound containing three functional groups, such as phenylmethane triisocyanate and methylene bistriisocyanate, etc. are mentioned.

Epoxy type crosslinking agent specifically, ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, polypropylene Glycol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, polytetramethylene glycol diglycidyl ether, glycerol diglycidyl ether, glycerol triglycidyl ether , Diglycerol polyglycidyl ether, polyglycerol polyglycidyl ether, resorcin diglycidyl ether, 2,2-dibromoneopentyl glycol diglycidyl ether, trimethylol propane triglycidyl ether, pentaerythrate Lithol polyglycidyl ether, sorbitol polyglycidyl ether, adipic acid diglycidyl ester, phthalic acid diglycidyl ester, tris (glycidyl) Isocyanurate, tris (glycidoxyethyl) isocyanurate, 1,3-bis (N, N-glycidylaminomethyl) cyclohexane, N, N, N ', N'-tetraglycidyl- m-xylylenediamine etc. are mentioned.

Further, in addition to the isocyanate-based crosslinking agent and the epoxy-based crosslinking agent, at least one crosslinking agent selected from the group consisting of melamine derivatives such as hexamethyrolmelamine, hexamethoxymethylmelamine, hexabutoxymethylmelamine and the like may be further added. Can be used together

Commercially available examples of the crosslinking agent include Cor-L (Japan Polyurethane Industry Co., Ltd.).

The content of the crosslinking agent is not particularly limited within the range capable of performing its function, for example, 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. Can be. If the content is less than 0.1 parts by weight, the cohesive force may be reduced due to insufficient crosslinking degree, thereby impairing the adhesive durability and the cutting property. If the content is more than 15 parts by weight, problems may occur in relieving residual stress due to an excessive crosslinking reaction.

The antistatic agent is not particularly limited as long as it is used in the art. For example, as the cation, organic cationic or alkali metal cations such as ammonium, pyridinium, imidazolium, phosphonium, and sulfonium may be used, and these may be used alone or in combination of two or more thereof.

Specific examples of ammonium include quaternary ammonium salts in which four alkyl groups such as tetrabutylamnonium are substituted. Specific examples of pyridinium include 1-ethylpyridinium, 1-butylpyridinium, 1-hexylpyridinium, 1 -Butyl-3-methylpyridinium, 1-butyl-4-methylpyridinium, 1-hexyl-3-methylpyridinium, 1-butyl-3,4-dimethylpyridinium, 1-octyl-4-methylpyridinium Pyridinium in which an alkyl group is substituted in N of the pyridine, and specific examples of imidazolium include imidazole, such as 1-methyl-3-butylimidazolium and 1-methyl-3-hexyl imidazolium. And imidazolium in which an alkyl group is substituted at the 1,3-position of. Examples of phosphonium include quaternary phosphonium salts having four alkyl substituents, such as tetrabutyl phosphonium, and sulfonium. Specific examples thereof include tertiary sulfonium salts having three alkyl substituents, such as tributyl sulfonium. In addition, specific examples of alkali metal cations include lithium salts, sodium salts, or potassium salts.

As the anion (sulfonate trifluoromethyl) OTf, OTs (toluene-4-sulfonate), OMs ^{(sulfonate), Cl -, Br -,} I -, AlCl 4 -, Al 2 Cl 7 -, BF 4 _{^{-, PF6 -, ClO 4 -}} , NO 3 -, CH3COO -, 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 ^-, and the like ^-, C ₃ F ₇ COO ^- or _{(CF 3 SO 2) (CF} 3 CO) N.

Among them, in view of durability and antistatic properties, sulfonylimide compounds are preferable, and examples thereof include compounds represented by the following general formula (15). In Formula 15, the sulfonylimide-based anion has a high electronegativity of fluorine atoms contained in the anion, and thus has a large stabilizing effect on the anion present in the nitrogen atom, thereby improving hydrophobicity of the antistatic agent and improving compatibility with the acrylic copolymer. It is preferable in that it is excellent in surface migration property and provides antistatic property with durability reliability.

[Formula 15]

M ⁺ [(SO ₂ R) ₂ N] ^-

Wherein M is an alkali metal and R is a fluorine atom or a perfluoroalkyl group having 1 to 4 carbon atoms.

The alkali metal may be lithium, sodium, potassium or cesium, preferably lithium, sodium or potassium.

More specific examples of the antistatic agent of Formula 15 include bis (fluorosulfonyl) imide potassium (KN (FSO ₂ ) ₂ ), bis (fluorosulfonyl) imide sodium (NaN (FSO ₂ ) ₂ ), Bis (fluorosulfonyl) imide lithium (LiN (FSO ₂ ) ₂ ), bis (trifluorosulfonyl) imide potassium (KN (CF ₃ SO ₂ ) ₂ ), bis (trifluorosulfonyl) imide Desodium (NaN (CF ₃ SO ₂ ) ₂ ) or bis (trifluorosulfonyl) imide lithium (LiN (CF ₃ SO ₂ ) ₂ ), and the like, and preferably bis (fluorosulfonyl) Potassium imide (KN (FSO ₂ ) ₂ ), bis (fluorosulfonyl) imide sodium (NaN (FSO ₂ ) ₂ ), and these may be used alone or in combination of two or more thereof.

The antistatic agent is preferably included in an amount of 0.1 to 10 parts by weight, and more preferably 0.5 to 5 parts by weight, based on 100 parts by weight of the acrylic copolymer based on solid content.

If the content is less than 0.1 parts by weight, the effect of imparting antistatic properties may be insignificant. If the content is more than 10 parts by weight, bleed out may occur easily, resulting in poor peeling under heat conditions.

The pressure-sensitive adhesive composition of the present invention may further include a silane coupling agent. The silane coupling agent covalently bonds to the adherend surface polar group, thereby improving adhesion.

A silane coupling agent will not be specifically limited if it contains functional groups, such as an amino group, an epoxy group, an acetoacetyl group, a polyalkylene glycol group, an acryl group, and an alkyl group, For example, vinyl trimethoxysilane, vinyl triethoxysilane, vinyl Tris (2-methoxyethoxy) silane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, 3-amino Propyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-chloropropylmeth Toxyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glyci Doxypropyldimethoxymethylsilane, 3-glycidoxypropylethoxydimethylsil Column; and the like. These can be used individually or in mixture of 2 or more types.

Commercially available examples of silane coupling agents include KBM-403 (Shin-Etsu Co., Ltd.).

The content of the silane coupling agent is not particularly limited. For example, the silane coupling agent may be included in an amount of 0.1 to 2 parts by weight, preferably 0.1 to 0.5 parts by weight, based on 100 parts by weight of the acrylic copolymer. When the content is less than 0.1 parts by weight, the adhesion to the substrate may be insufficient, so that peeling may occur under moisture-resistant heat conditions. When the content is more than 2 parts by weight, the cohesion may be excessively increased, and thus the durability may be lowered as the adhesive properties such as adhesive strength are lowered. have.

In addition, the pressure-sensitive adhesive composition of the present invention, antioxidants, leveling agents, surface lubricants, dyes, pigments, light stabilizers, corrosion inhibitors, antifoaming agents, fillers, commonly used in the art within the scope without departing from the object of the present invention It may further include an additive such as an antistatic agent.

<Adhesive sheet>

In addition, the present invention provides a pressure-sensitive adhesive sheet comprising a pressure-sensitive adhesive layer formed of the pressure-sensitive adhesive composition.

The thickness of the adhesive layer is not particularly limited, and may be, for example, 3 to 100 μm, preferably 10 to 100 μm.

The adhesive sheet of the present invention includes an adhesive layer formed on at least one surface of the release film.

The pressure-sensitive adhesive layer can be formed by coating the pressure-sensitive adhesive composition on at least one surface of the release film. The coating method is not particularly limited, and methods known in the art may be used. For example, methods such as a bar coater, air knife, gravure, reverse roll, kiss roll, spray, blade, die coater, casting, and spin coating may be used. It is available.

The release film is not particularly limited, and a release film commonly used in an adhesive sheet may be used, for example, polyester resins such as polyethylene terephthalate, polybutyrene terephthalate, polyethylene naphthalate, and polybutylene naphthalate; Polyimide resins; Acrylic resins; Styrene resins such as polystyrene and acrylonitrile-styrene; Polycarbonate resins; Polylactic acid resins; Polyurethane resins; Polyolefin resins such as polyethylene, polypropylene, ethylene-propylene copolymers; Vinyl resins such as polyvinyl chloride and polyvinylidene chloride; Polyamide resins; Sulfone resins; Polyether ether ketone resins; Allyl resins; Or it may be formed of a mixture of the resin.

The thickness of the release film is not particularly limited, and may be, for example, 5 to 500 μm, and preferably 10 to 100 μm.

<Polarizing plate>

In addition, the present invention provides a polarizing plate including a pressure-sensitive adhesive layer formed on at least one surface of the pressure-sensitive adhesive composition.

The polarizing plate of the present invention includes a polarizer, a protective film bonded to at least one surface of the polarizer, and an adhesive layer formed of the pressure-sensitive adhesive composition on the protective film.

The polarizer may be a polarizer known in the art, and for example, may be manufactured by swelling, dyeing, crosslinking, stretching, washing, drying, and the like of a polyvinyl alcohol-based film.

The protective film is not particularly limited as long as the film is excellent in transparency, mechanical strength, thermal stability, moisture shielding, and isotropy. Specifically, polyester film, such as polyethylene terephthalate, polyethylene isophthalate, polybutylene terephthalate; Cellulose films such as diacetyl cellulose and triacetyl cellulose; Polycarbonate film; Acrylic films such as polymethyl (meth) acrylate and polyethyl (meth) acrylate; Styrene films such as polystyrene and acrylonitrile-styrene copolymers; Polyolefin-based film; Vinyl chloride film; Polyamide films such as nylon and aromatic polyamides; Imide film; Sulfone film; Polyether ketone film; Sulfided polyphenylene-based films; Vinyl alcohol film; Vinylidene chloride-based film; Vinyl butyral film; Allylate film; Polyoxymethylene film; Urethane film; Epoxy film; Silicone film etc. are mentioned. Among these, especially the cellulose type film which has the surface saponified by saponification by alkali etc. is preferable in consideration of polarization characteristic or durability. In addition, the protective film may have a function of the optical layer.

The adhesive layer may be directly coated on the protective film, or may be formed by attaching the adhesive sheet to the protective film.

<Image display device>

In addition, the present invention provides an image display device including the polarizing plate.

The image display apparatus of the present invention may further include a configuration known in the art in addition to the polarizing plate.

Hereinafter, preferred examples are provided to aid the understanding of the present invention, but these examples are merely illustrative of the present invention and are not intended to limit the scope of the appended claims, which are within the scope and spirit of the present invention. It is apparent to those skilled in the art that various changes and modifications can be made to the present invention, and such modifications and changes belong to the appended claims.

Preparation Example: Preparation of Acrylic Copolymer

Nitrogen gas is refluxed, 90 parts by weight of n-butyl acrylate, 7 parts by weight of methacrylate, 2 parts by weight of 2-hydroxyethyl acrylate, 1 weight of acrylic acid in a 1 L reactor equipped with a cooling device for easy temperature control After adding a monomer mixture consisting of parts, 100 parts by weight of ethyl acetate was added as a solvent. Nitrogen gas was then purged for 1 hour to remove oxygen and then held at 62 ° C. After the mixture was uniformly mixed, 0.07 parts by weight of azobisisobutyronitrile (AIBN) was added as a reaction initiator, and reacted for 8 hours to prepare an acrylic copolymer (a weight average molecular weight of about 1 million).

Example

 (1) Preparation of Pressure-Sensitive Adhesive Composition

To prepare a pressure-sensitive adhesive composition having the composition and content shown in Table 1.

(2) Production of an adhesive sheet

After preparing the pressure-sensitive adhesive composition, it was applied on a film coated with a silicone release agent, and dried at 100 ° C. for 1 minute to form a pressure-sensitive adhesive layer of 25 μm.

Thereafter, a release film was laminated on the pressure-sensitive adhesive layer to prepare a pressure-sensitive adhesive sheet.

(3) Production of adhesive polarizing plate

After peeling the release film of the prepared pressure-sensitive adhesive sheet, a pressure-sensitive adhesive layer was laminated on an iodine polarizing plate containing a TAC protective film of 185㎛ thickness to prepare a polarizing plate with pressure-sensitive adhesive.

Table 1

Experimental Example

The pressure-sensitive adhesive compositions of Examples and Comparative Examples were applied on a release film coated with a silicone release agent so as to have a thickness of 25 μm, and dried at 100 ° C. for 1 minute to form an adhesive layer.

Subsequently, the adhesive layer prepared above was laminated on the iodine-based polarizing film (total thickness 185 μm) to which a triacetyl cellulose protective film was bonded on both sides, to prepare a polarizing plate. The prepared polarizing plate was stored for 7 days under the condition of 23 ° C., 60% RH.

(1) Antistatic evaluation

The surface resistivity of the prepared polarizing plate was measured. (Unit: Ω cm)

 (2) heat resistance evaluation

After removing the release film of the prepared polarizing plate, bonded to the Corning glass, and subjected to autoclave treatment, and left for 300 hours at a temperature of 60 ℃ after evaluating whether the occurrence of bubbles or peeling was evaluated.

Χ: Bubbles or peelings from the front.

(Triangle | delta): 3-10 bubbles or peelings were confirmed.

○: One or two bubbles or peelings were confirmed.

(Double-circle): Bubble or peeling is not visually recognized.

TABLE 2

As can be seen from Table 2, in the case of the pressure-sensitive adhesive composition in which the polyamino ether compound of the present invention is used, not only exhibits excellent antistatic property, but also high heat resistance in which peeling does not easily occur even under conditions of high temperature and high humidity.

However, it was found that the heat resistance was somewhat lowered in the case of Example 9 containing the antistatic agent in an excessive amount.

In the case of the comparative examples, it can be seen that the antistatic property and the heat resistance is significantly reduced as a whole, in particular, in the case of Comparative Example 2 has a better effect than Comparative Example 1 does not include an additive corresponding to the polyamino ether compound, but compared It was found that the heat resistance was low as compared with Example 2 containing the same amount of polyamino ether compound as in Example 2.

Claims (8)

1. A pressure-sensitive adhesive composition comprising a polyaminoether compound having at least two tertiary amines and at least one ether group in the molecule, an acrylic copolymer, a crosslinking agent and an antistatic agent.
2. The pressure-sensitive adhesive composition of claim 1, wherein the polyaminoether compound having at least two tertiary amines and at least one ether group in the molecule is a compound represented by Formula 1 below:

   [Formula 1]

   

   Wherein R ₁ , R ₂ , R ₃ and R ₄ are each independently a substituted or unsubstituted linear or branched C1-C12 alkyl or C6-C12 aryl group having 6 to 12 carbon atoms. R ₁ and R ₂ or R ₃ and R ₄ may be linked to each other to form a hydrocarbon ring, and when n is 2 or more, R ₁ may be changed for each repeating unit, and n is an integer of 1 to 5 ).
3. The pressure-sensitive adhesive composition of claim 2, wherein the compound represented by Chemical Formula 1 is at least one selected from the group consisting of Chemical Formulas 2 to 14:

    [Formula 2]

   

   [Formula 3]

   

   [Formula 4]

   

   [Formula 5]

   

   [Formula 6]

   

   [Formula 7]

   

   [Formula 8]

   

   [Formula 9]

   

   [Formula 10]

   

   [Formula 11]

   

   [Formula 12]

   

   [Formula 13]

   

   [Formula 14]

   

   .
4. The pressure-sensitive adhesive composition of claim 1, wherein the polyaminoether compound having at least two tertiary amines and at least one ether group is included in an amount of 0.1 to 10 parts by weight based on 100 parts by weight of the acrylic copolymer based on solid content.
5. The method of claim 1, wherein the antistatic agent is at least one of bis (fluorosulfonyl) imide potassium (KN (FSO ₂ ) ₂ ) or bis (fluorosulfonyl) imide sodium (NaN (FSO ₂ ) ₂ ). , Pressure-sensitive adhesive composition.
6. The adhesive sheet containing the adhesion layer formed from the adhesive composition of any one of Claims 1-5.
7. The polarizing plate provided with the adhesion layer formed from the adhesive composition of any one of Claims 1-5 on at least one surface.
8. An image display device comprising the polarizing plate of claim 7.