KR20130050041A - Copolymer and pressure-sensitive adhesive composion comprising the same - Google Patents
Copolymer and pressure-sensitive adhesive composion comprising the same Download PDFInfo
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- KR20130050041A KR20130050041A KR1020110115171A KR20110115171A KR20130050041A KR 20130050041 A KR20130050041 A KR 20130050041A KR 1020110115171 A KR1020110115171 A KR 1020110115171A KR 20110115171 A KR20110115171 A KR 20110115171A KR 20130050041 A KR20130050041 A KR 20130050041A
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- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
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- G02B5/00—Optical elements other than lenses
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- G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
- G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid
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Abstract
Description
본 발명은 양생이 빠르고 경시안정성이 우수한 점착제 조성물을 제공할 수 있는 공중합체 및 이를 포함하는 점착제 조성물에 관한 것이다.
The present invention relates to a copolymer that can provide a pressure-sensitive adhesive fast and excellent aging stability, and a pressure-sensitive adhesive composition comprising the same.
액정표시장치(Liquid crystal display device, LCD)는 액정셀과 상기 액정셀의 양면에 점착제층을 매개로 접합된 편광판을 포함하는 액정패널을 구비한다.A liquid crystal display device (LCD) includes a liquid crystal panel including a liquid crystal cell and a polarizing plate bonded to both surfaces of the liquid crystal cell via an adhesive layer.
액정셀과 편광판의 접합을 위한 점착제는 기재와의 밀착성, 빛샘 방지성, 내열 및 내습열 내구성뿐만 아니라 리워크성과 같은 물성을 동시에 만족시켜야 한다. 또한, 상기 언급된 물성과 함께 점착제는 양생 기간을 단축시켜 생산성도 향상시킬 것이 요구된다.The pressure-sensitive adhesive for bonding the liquid crystal cell and the polarizing plate must satisfy physical properties such as reworkability as well as adhesion to the substrate, light leakage resistance, heat and moisture resistance. In addition, the pressure-sensitive adhesive together with the above-mentioned physical properties is required to shorten the curing period to improve productivity.
이와 같이 종래 점착제로서 요구되는 물성을 유지하면서도 양생 기간을 단축시키기 위한 방법으로 가교반응을 촉진시키는 가교촉진제를 이용하는 방법이 제안되었다.As such, a method of using a crosslinking accelerator which promotes a crosslinking reaction has been proposed as a method for shortening the curing period while maintaining physical properties required as a conventional adhesive.
한국공개특허 제2009-0132116호에는 특정 구조의 루이스 염기를 포함하는 점착제 조성물이 개시되어 있고, 한국공개특허 제2008-0047030호에는 루이스 산을 포함하는 점착제 조성물이 개시되어 있다. 상기 문헌들에 기재된 점착제 조성물은 양생 단축의 효과는 있으나, 가교촉진제의 첨가로 인해 점착제 조성물의 점도가 급격하게 변화되어 저장 안정성을 저하시키고 점착제의 포트-라이프를 단축시키는 단점이 있으며, 이로 인해 공정 안정성에 문제를 일으킬 수 있다.
Korean Patent Publication No. 2009-0132116 discloses an adhesive composition comprising a Lewis base having a specific structure, and Korean Patent Publication No. 2008-0047030 discloses an adhesive composition containing a Lewis acid. Although the pressure-sensitive adhesive composition described in the above documents has an effect of shortening curing, the viscosity of the pressure-sensitive adhesive composition changes rapidly due to the addition of a crosslinking accelerator, which lowers the storage stability and shortens the pot-life of the pressure-sensitive adhesive, and thus the process It may cause stability problems.
본 발명은 양생 시간이 짧을 뿐만 아니라 경시 안정성이 우수한 점착제 조성물을 제공할 수 있는 공중합체를 제공하는 것을 목적으로 한다.An object of the present invention is to provide a copolymer capable of providing a pressure-sensitive adhesive composition having a short curing time and excellent stability over time.
또한, 본 발명은 위 공중합체를 포함하는 점착제 조성물을 제공하는 것을 목적으로 한다.In addition, an object of the present invention is to provide a pressure-sensitive adhesive composition containing the above copolymer.
또한, 본 발명은 위 점착제 조성물을 사용한 액정표시장치를 제공하는 것을 목적으로 한다.
In addition, an object of the present invention is to provide a liquid crystal display device using the pressure-sensitive adhesive composition.
1. 하기 화학식 1로 표시되는 단량체로 형성되는 반복단위를 포함하는 아크릴계 공중합체:1. Acrylic copolymer comprising a repeating unit formed of a monomer represented by the following formula (1):
(식 중, R1은 수소 또는 메틸기이며, R2는 -CN, -NO2, -COCF3, -SO2CF3 , -Ph-CN 또는 -Ph-NO2이며, n은 1 내지 4의 정수임).(Wherein R 1 is hydrogen or methyl group, R 2 is —CN, —NO 2 , —COCF 3 , —SO 2 CF 3 , —Ph-CN or —Ph-NO 2 , n is 1-4); Integer).
2. 위 1에 있어서, 위 공중합체는 탄소수 1 내지 12인 알킬기를 포함하는 (메타)아크릴레이트계 단량체와 상기 화학식 1로 표시되는 단량체가 공중합되어 형성되는 공중합체.2. The copolymer according to 1 above, wherein the copolymer is formed by copolymerizing a (meth) acrylate-based monomer including an alkyl group having 1 to 12 carbon atoms with the monomer represented by Formula 1.
3. 위 2에 있어서, 위 공중합체는 탄소수 1 내지 12인 알킬기를 포함하는 (메타)아크릴레이트계 단량체 100 중량부 및 상기 화학식 1로 표시되는 단량체 0.01 내지 10 중량부가 중합되어 형성되는 공중합체.3. The copolymer according to the above 2, wherein the copolymer is formed by polymerizing 100 parts by weight of a (meth) acrylate monomer including an alkyl group having 1 to 12 carbon atoms and 0.01 to 10 parts by weight of the monomer represented by Formula 1.
4. 위 2에 있어서, 위 (메타)아크릴레이트계 단량체는 메틸 (메타)아크릴레이트, 에틸 (메타)아크릴레이트, n-프로필 (메타)아크릴레이트, 이소프로필(메타)아크릴레이트, n-부틸 (메타)아크릴레이트, 2-부틸 (메타)아크릴레이트, t-부틸 (메타)아크릴레이트, 2-에틸헥실 (메타)아크릴레이트, 2-에틸부틸 (메타)아크릴레이트, 펜틸 (메타)아크릴레이트, n-옥틸 (메타)아크릴레이트, 이소옥틸 (메타)아크릴레이트, n-노닐 (메타)아크릴레이트, 이소노닐 (메타)아크릴레이트, 데실 (메타)아크릴레이트 및 라우릴 (메타)아크릴레이트로 이루어진 군에서 선택되는 적어도 1종인 공중합체.4. In the above 2, the (meth) acrylate monomers are methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (Meth) acrylate, 2-butyl (meth) acrylate, t-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, 2-ethylbutyl (meth) acrylate, pentyl (meth) acrylate with n-octyl (meth) acrylate, isooctyl (meth) acrylate, n-nonyl (meth) acrylate, isononyl (meth) acrylate, decyl (meth) acrylate and lauryl (meth) acrylate At least one copolymer selected from the group consisting of.
5. 위 1에 있어서, 가교성 관능기를 갖는 단량체를 더 포함하여 중합되는 공중합체.5. The copolymer according to the above 1, further comprising a monomer having a crosslinkable functional group.
6. 위 5에 있어서, 위 가교성 관능기는 히드록시기, 카르복시기, 아미드기 또는 3차 아민기인 공중합체.6. The copolymer according to the above 5, wherein the crosslinkable functional group is a hydroxy group, a carboxy group, an amide group or a tertiary amine group.
7. 위 5에 있어서, 위 가교성 관능기를 갖는 단량체는 전체 단량체 총 중량에 대하여 0.1 내지 15중량%로 포함되는 공중합체.7. The copolymer of the above 5, wherein the monomer having a cross-linkable functional group is included in 0.1 to 15% by weight relative to the total weight of the monomer.
8. 위 1에 있어서, 중량평균 분자량이 20만 내지 150만인 공중합체.8. In the above 1, the weight average molecular weight is 200,000 to 1.5 million copolymers.
9. 위 1 내지 8 중 어느 하나의 공중합체 및 가교제를 포함하는 점착제 조성물.9. Pressure-sensitive adhesive composition comprising any one of the copolymers 1 to 8 and the crosslinking agent.
10. 위 9에 있어서, 위 가교제는 위 공중합체 고형분 100 중량부에 대하여 0.1 내지 15 중량부로 포함되는 점착제 조성물.10. The pressure-sensitive adhesive composition of 9, 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 above copolymer solids.
11. 위 9의 점착제 조성물로 형성된 점착제층이 구비된 편광판.11. The polarizing plate with a pressure-sensitive adhesive layer formed of the pressure-sensitive adhesive composition of the above 9.
12. 위 11의 편광판이 구비된 액정표시장치.
12. A liquid crystal display device having a polarizing plate of 11 above.
본 발명의 공중합체는 카르보닐기의 β위치에 전자끌게(electron withdrawing group)를 도입하여 α위치의 탄소의 반응성이 높은 구조를 가짐으로써 점착제 조성물에 사용되면 양생 시간이 짧고 경시 안정성은 우수하게 유지할 수 있다.The copolymer of the present invention has a structure having high reactivity of carbon at the α position by introducing an electron withdrawing group at the β position of the carbonyl group, so that the curing time is short and the stability over time can be kept excellent when used in the adhesive composition. .
본 발명의 공중합체를 포함하는 점착제 조성물은 내열성, 내습열성, 점착력, 리워크성, 내구성 등이 우수하다.
The adhesive composition containing the copolymer of this invention is excellent in heat resistance, heat and humidity resistance, adhesive force, rework property, durability, etc.
본 발명은 화학식 1로 표시되는 단량체로 형성되는 반복단위를 포함함으로써, 점착제 조성물에 사용되면 양생 시간이 짧고 경시 안정성은 우수하게 유지할 수 있는 공중합체 및 이를 포함하는 점착제 조성물에 관한 것이다.The present invention relates to a copolymer and a pressure-sensitive adhesive composition comprising a repeating unit formed of a monomer represented by the formula (1), when used in the pressure-sensitive adhesive composition, the curing time is short and excellent stability over time.
이하, 본 발명을 상세히 설명하기로 한다. Hereinafter, the present invention will be described in detail.
본 발명의 아크릴계 공중합체는 하기 화학식 1로 표시되는 단량체로 형성되는 반복단위를 포함하는 것을 특징으로 한다:Acrylic copolymer of the present invention is characterized in that it comprises a repeating unit formed of a monomer represented by the formula (1):
[화학식 1][Formula 1]
식 중, R1은 수소 또는 메틸기이며, R2는 -CN, -NO2, -COCF3, -SO2CF3 , -Ph-CN 또는 -Ph-NO2이며, n은 1 내지 4의 정수임. 여기서 Ph는 페닐기를 의미한다.Wherein R 1 is hydrogen or methyl, R 2 is -CN, -NO 2 , -COCF 3 , -SO 2 CF 3 , -Ph-CN or -Ph-NO 2 , n is an integer from 1 to 4 . Ph here means a phenyl group.
본 발명의 공중합체는 카르보닐기의 β위치에 전자끌게인 -CN, -NO2, -COCF3, -SO2CF3, -Ph-CN 또는 -Ph-NO2를 도입하여 α위치의 탄소의 반응성이 높은 구조를 갖는 단량체가 공중합되어 형성됨으로써 양생 시간이 짧고 경시 안정성은 우수하게 유지할 수 있다.The copolymer of the present invention is introduced at the β-position of the carbonyl group -CN, -NO 2 , -COCF 3 , -SO 2 CF 3 , -Ph-CN or -Ph-NO 2 by introducing a carbon reactivity of the α position By copolymerizing and forming the monomer which has this high structure, curing time is short and stability with time can be maintained excellent.
또한, 위 화학식 1에서 에틸렌글리콜 구조는 대전방지성을 나타내어 본 발명의 공중합체가 점착제로 사용되면 대전방지성능을 갖는 점착제로 사용될 수 있다.In addition, the ethylene glycol structure in the above formula (1) shows an antistatic property can be used as an adhesive having an antistatic performance when the copolymer of the present invention is used as an adhesive.
본 발명의 아크릴계 공중합체는 위 화학식 1의 단량체와 (메타)아크릴레이트계 단량체를 공중합하여 형성될 수 있는데, (메타)아크릴레이트 단량체는 공중합체의 주된 구조를 형성하고 점착성을 발휘한다. (메타)아크릴레이트계 단량체는 탄소수 1 내지 12인 알킬기를 포함하는 (메타)아크릴레이트계 단량체가 바람직하다. The acrylic copolymer of the present invention can be formed by copolymerizing the monomer of Formula 1 with (meth) acrylate monomer, wherein the (meth) acrylate monomer forms the main structure of the copolymer and exhibits stickiness. (Meth) acrylate monomer is preferably a (meth) acrylate monomer containing an alkyl group having 1 to 12 carbon atoms.
본 발명의 화학식 1의 단량체가 탄소수 1 내지 12인 알킬기를 포함하는 (메타)아크릴레이트계 단량체와 공중합하는 경우, 위 화학식 1로 표시되는 단량체는 (메타)아크릴레이트계 단량체 100 중량부 대비 0.01 내지 10 중량부, 바람직하게는 0.1 내지 8중량부로 포함되어 공중합체를 형성한다. 그 함량이 0.01 중량부 미만이면 점착제 조성물에 사용될 경우 양생 시간 단축 효과가 미미하고, 10 중량부 초과이면 점착제 조성물의 내구성이 저하된다.When the monomer of Formula 1 of the present invention is copolymerized with a (meth) acrylate monomer including an alkyl group having 1 to 12 carbon atoms, the monomer represented by Formula 1 is 0.01 to 100 parts by weight based on 100 parts by weight of the (meth) acrylate monomer. 10 parts by weight, preferably 0.1 to 8 parts by weight to form a copolymer. If the content is less than 0.01 parts by weight, the curing time shortening effect is insignificant when used in the pressure-sensitive adhesive composition, the durability of the pressure-sensitive adhesive composition is lowered if it is more than 10 parts by weight.
탄소수 1 내지 12인 알킬기를 포함하는 (메타)아크릴레이트 단량체의 구체적인 예시로는 메틸 (메타)아크릴레이트, 에틸 (메타)아크릴레이트, n-프로필 (메타)아크릴레이트, 이소프로필(메타)아크릴레이트, n-부틸 (메타)아크릴레이트, 2-부틸 (메타)아크릴레이트, t-부틸 (메타)아크릴레이트, 2-에틸헥실 (메타)아크릴레이트, 2-에틸부틸 (메타)아크릴레이트, 펜틸 (메타)아크릴레이트, n-옥틸 (메타)아크릴레이트, 이소옥틸 (메타)아크릴레이트, n-노닐 (메타)아크릴레이트, 이소노닐 (메타)아크릴레이트, 데실 (메타)아크릴레이트, 라우릴 (메타)아크릴레이트 등을 각각 단독으로 또는 2종 이상 혼합하여 사용할 수 있다.Specific examples of the (meth) acrylate monomer containing an alkyl group having 1 to 12 carbon atoms include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, and isopropyl (meth) acrylate. , n-butyl (meth) acrylate, 2-butyl (meth) acrylate, t-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, 2-ethylbutyl (meth) acrylate, pentyl ( Meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, n-nonyl (meth) acrylate, isononyl (meth) acrylate, decyl (meth) acrylate, lauryl (meth) ) Acrylate etc. can be used individually or in mixture of 2 or more types, respectively.
선택적으로, 본 발명의 공중합체는 가교성 관능기를 갖는 단량체를 더 포함할 수 있다. 가교성 관능기를 갖는 단량체는 화학 결합에 의해 점착제 조성물의 응집력 또는 점착 강도를 보강하여 내구성과 절단성을 부여하기 위한 성분으로서, 예컨대 히드록시기를 갖는 단량체, 카르복시기를 갖는 단량체, 아미드기를 갖는 단량체, 3차 아민기를 갖는 단량체 등을 들 수 있으며, 이들은 단독 또는 2종 이상 혼합하여 사용할 수 있고, 바람직하게는 히드록시기를 갖는 단량체를 사용할 수 있다.Alternatively, the copolymer of the present invention may further comprise a monomer having a crosslinkable functional group. The monomer having a crosslinkable functional group is a component for imparting durability and cutability by reinforcing the cohesive strength or adhesive strength of the pressure-sensitive adhesive composition by chemical bonding, and examples thereof include monomers having a hydroxy group, monomers having a carboxyl group, monomers having an amide group, And amine group-containing monomers. These monomers may be used alone or in admixture of two or more, preferably monomers having a hydroxy group.
히드록시기를 갖는 단량체로는 2-히드록시에틸(메타)아크릴레이트, 2-히드록시프로필(메타)아크릴레이트, 2-히드록시부틸(메타)아크릴레이트, 4-히드록시부틸(메타)아크릴레이트, 6-히드록시헥실(메타)아크릴레이트, 2-히드록시에틸렌글리콜(메타)아크릴레이트, 2-히드록시프로필렌글리콜(메타)아크릴레이트, 알킬렌기의 탄소수가 2-4인 히드록시알킬렌글리콜(메타)아크릴레이트, 4-히드록시부틸비닐에테르, 5-히드록시펜틸비닐에테르, 6-히드록시헥실비닐에테르, 7-히드록시헵틸비닐에테르, 8-히드록시옥틸비닐에테르, 9-히드록시노닐비닐에테르, 10-히드록시데실비닐에테르 등을 들 수 있으며, 이들 중에서 4-히드록시부틸비닐에테르가 바람직하다.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, 4-hydroxybutyl vinyl ether is preferable.
카르복시기를 갖는 단량체로는 (메타)아크릴산, 크로톤산 등의 1가산; 말레인산, 이타콘산, 푸마르산 등의 2가산 및 이들의 모노알킬에스테르; 3-(메타)아크릴로일프로피온산; 알킬기의 탄소수가 2-3인 2-히드록시알킬(메타)아크릴레이트의 무수호박산 개환 부가체, 알킬렌기의 탄소수가 2-4인 히드록시알킬렌글리콜(메타)아크릴레이트의 무수 호박산 개환 부가체, 알킬기의 탄소수가 2-3인 2-히드록시알킬(메타)아크릴레이트의 카프로락톤 부가체에 무수 호박산을 개환 부가시킨 화합물 등을 들 수 있으며, 이들 중에서 (메타)아크릴산이 바람직하다.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 , Compounds obtained by ring-opening addition of succinic anhydride to caprolactone adducts of 2-hydroxyalkyl (meth) acrylates whose alkyl groups have 2-3 carbon atoms, and among these, (meth) acrylic acid is preferable.
아미드기를 갖는 단량체로는 (메타)아크릴아미드, N-이소프로필아크릴아미드, N-3차부틸아크릴아미드, 3-히드록시프로필(메타)아크릴아미드, 4-히드록시부틸(메타)아크릴아미드, 6-히드록시헥실(메타)아크릴아미드, 8-히드록시옥틸(메타)아크릴아미드, 2-히드록시에틸헥실(메타)아크릴아미드 등을 들 수 있으며, 이들 중에서 (메타)아크릴아미드가 바람직하다.Examples of the monomer having an amide group include (meth) acrylamide, N-isopropyl acrylamide, N-tertiary butyl acrylamide, 3-hydroxypropyl (meth) acrylamide, 4-hydroxybutyl (Meth) acrylamide, 8-hydroxyoctyl (meth) acrylamide and 2-hydroxyethylhexyl (meth) acrylamide. Of these, (meth) acrylamide is preferable.
3차 아민기를 갖는 단량체로는 N,N-(디메틸아미노)에틸(메타)아크릴레이트, N,N-(디에틸아미노)에틸(메타)아크릴레이트, N,N-(디메틸아미노)프로필(메타)아크릴레이트 등을 들 수 있다.Examples of the monomer having a tertiary amine group include N, N- (dimethylamino) ethyl (meth) acrylate, N, N- (diethylamino) ethyl (meth) ) Acrylate, and the like.
가교성 관능기를 갖는 단량체는 전체 단량체 총 중량에 대하여 0.1 내지 15중량%로 포함될 수 있고, 보다 바람직하게는 1 내지 10중량%로 포함될 수 있다. 함량이 0.1중량% 미만인 경우 점착제의 응집력이 작아지게 되어 내구성이 저하될 수 있으며, 10중량% 초과인 경우 높은 겔분율에 의해 점착력이 떨어지고 내구성에 문제를 야기할 수 있다.The monomer having a crosslinkable functional group may be contained in an amount of 0.1 to 15% by weight, more preferably 1 to 10% by weight based on the total weight of the total monomers. If the content is less than 0.1% by weight, the cohesive force of the pressure-sensitive adhesive may be reduced, the durability may be lowered. When the content is more than 10% by weight, the adhesive strength may be degraded by a high gel fraction and may cause a problem in durability.
또한, 상기 단량체들 이외에 다른 중합성 단량체가 점착력을 저하시키지 않는 범위, 예컨대 10중량% 이하로 더 포함될 수 있다.In addition, other polymerizable monomers in addition to the monomers may be further included in a range that does not lower the adhesion, such as 10% by weight or less.
공중합체의 제조방법은 특별히 한정되지 않으며, 당 분야에서 통상적으로 사용되는 괴상중합, 용액중합, 유화중합 또는 현탁중합 등의 방법을 이용하여 제조할 수 있으며, 용액중합이 바람직하다. 또한, 중합 시 통상 사용되는 용매, 중합개시제, 분자량 제어를 위한 연쇄이동제 등을 사용할 수 있다.The method for producing the copolymer is not particularly limited and can be produced by methods such as bulk polymerization, solution polymerization, emulsion polymerization or suspension polymerization, which are commonly used in the art, and solution polymerization is preferable. In addition, a solvent, a polymerization initiator, a chain transfer agent for molecular weight control and the like which are usually used in polymerization can be used.
공중합체는 겔투과크로마토그래피(Gel permeation chromatography, GPC)에 의해 측정된 중량평균 분자량(폴리스티렌 환산, Mw)이 20만 내지 150만, 바람직하게 40만 내지 100만일 수 있다. 분자량이 20만 미만이면 공중합체 간의 응집력이 부족하여 점착 내구성에 문제를 야기할 수 있고, 150만 초과이면 도공 시 공정성을 확보하기 위하여 다량의 희석 용매를 필요로 하는 문제가 있다.The copolymer may have a weight average molecular weight (polystyrene equivalent, Mw) measured by gel permeation chromatography (GPC) of 200,000 to 1.50,000, preferably 400,000 to 1 million. When the molecular weight is less than 200,000, cohesion between copolymers may be insufficient, which may cause problems in adhesion durability. When the molecular weight is more than 1.5 million, a large amount of diluting solvent is required to ensure fairness during coating.
본 발명의 공중합체는 가교제와 함께 혼합되어 점착제 조성물로 사용될 수 있다.The copolymer of the present invention can be mixed with a crosslinking agent and used as a pressure-sensitive adhesive composition.
가교제는 공중합체를 적절히 가교함으로써 점착제의 응집력을 강화하기 위한 성분으로서, 그 종류는 특별히 한정되지 않는다. 예컨대, 이소시아네이트계 화합물, 에폭시계 화합물 등을 들 수 있으며, 이들은 단독 또는 2종 이상 혼합하여 사용할 수 있다.A crosslinking agent is a component for strengthening the cohesion force of an adhesive by crosslinking a copolymer suitably, The kind is not specifically limited. For example, an isocyanate type compound, an epoxy type compound, etc. are mentioned, These can be used individually or in mixture of 2 or more types.
이소시아네이트계 화합물로는 톨릴렌디이소시아네이트, 자일렌디이소시아네이트, 2,4-디페닐메탄디이소시아네트, 4,4-디페닐메탄디이소시아네트, 헥사메틸렌디이소시아네이트, 이소포론디이소시아네이트, 테트라메틸자일렌디이소시아네이트, 나프탈렌디이소시아네이트 등의 디이소시아네이트 화합물; 트리메틸올프로판 등의 다가 알콜계 화합물 1몰에 디이소시아네이트 화합물 3몰을 반응시킨 부가체, 디이소시아네이트 화합물 3몰을 자기 축합시킨 이소시아누레이트체, 디이소시아네이트 화합물 3몰 중 2몰로부터 얻어지는 디이소시아네이트 우레아에 나머지 1몰의 디이소시아네이트가 축합된 뷰렛체, 트리페닐메탄트리이소시아네이트, 메틸렌비스트리이소시아네이트 등의 3개의 관능기를 함유하는 다관능 이소시아네이트 화합물 등을 들 수 있다.As the isocyanate compound, tolylene diisocyanate, xylene diisocyanate, 2,4-diphenylmethane diisocyanate, 4,4-diphenylmethane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, tetramethyl xylene diisocyanate Diisocyanate compounds such as naphthalene diisocyanate; Diisocyanate obtained from 2 moles of an adduct obtained by reacting 3 moles of a diisocyanate compound with 1 mole of a polyhydric alcohol compound such as trimethylolpropane, an isocyanurate obtained by self-condensing 3 moles of the diisocyanate compound, and 3 moles of the diisocyanate compound And polyfunctional isocyanate compounds containing three functional groups such as biuret, triphenylmethanetriisocyanate, and methylenebistriisocyanate, in which the remaining 1 mole of diisocyanate is condensed to urea.
에폭시계 화합물로는 에틸렌글리콜디글리시딜에테르, 디에틸렌글리콜디글리시딜에테르, 폴리에틸렌글리콜디글리시딜에테르, 프로필렌글리콜디글리시딜에테르, 트리프로필렌글리콜디글리시딜에테르, 폴리프로필렌글리콜디글리시딜에테르, 네오펜틸글리콜디글리시딜에테르, 1,6-헥산디올디글리시딜에테르, 폴리테트라메틸렌글리콜디글리시딜에테르, 글리세롤디글리시딜에테르, 글리세롤트리글리시딜에테르, 디글리세롤폴리글리시딜에테르, 폴리글리세롤폴리글리시딜에테르, 레졸신디글리시딜에테르, 2,2-디브로모네오펜틸글리콜디글리시딜에테르, 트리메틸올프로판트리글리시딜에테르, 펜타에리트리톨폴리글리시딜에테르, 소르비톨폴리글리시딜에테르, 아디핀산디글리시딜에스테르, 프탈산디글리시딜에스테르, 트리스(글리시딜)이소시아누레이트, 트리스(글리시독시에틸)이소시아누레이트, 1,3-비스(N,N-글리시딜아미노메틸)시클로헥산, N,N,N',N'-테트라글리시딜-m-자일릴렌디아민 등을 들 수 있다.Examples of the epoxy compound include ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, and 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, trimethylolpropanetriglycidyl ether, pentaerythritol Polyglycidyl ether, sorbitol polyglycidyl ether, adipic acid diglycidyl ester, phthalic acid diglycidyl ester, tris (glycidyl) isocyanur Tris (glycidoxyethyl) isocyanurate, 1,3-bis (N, N-glycidylaminomethyl) cyclohexane, N, N, N ', N'-tetraglycidyl-m- Xylylenediamine etc. are mentioned.
또한, 이소시아네이트계 화합물, 에폭시계 화합물과 함께 멜라민계 화합물을 단독 또는 2종 이상 혼합하여 추가로 사용할 수 있다.Moreover, melamine type compound can be used individually or in mixture of 2 or more types together with an isocyanate type compound and an epoxy type compound.
멜리민계 화합물로는 헥사메틸올멜라민, 헥사메톡시메틸멜라민, 헥사부톡시메틸멜라민 등을 들 수 있다.Hexamethylol melamine, hexamethoxymethylmelamine, hexabutoxymethylmelamine, etc. are mentioned as a melamine type compound.
가교제는 고형분 함량을 기준으로 공중합체 100중량부에 대하여 0.1 내지 15중량부로 포함되는 것이 바람직하고, 보다 바람직하게는 0.1 내지 5중량부인 것이 좋다. 함량이 0.1중량부 미만인 경우 부족한 가교도로 인해 응집력이 작아지게 되어 들뜸과 같은 내구성 저하가 유발되고 절단성을 해칠 수 있으며, 15중량부 초과인 경우 과다 가교반응에 의해 잔류응력 완화에 문제가 발생할 수 있다.The crosslinking agent is preferably included in an amount of 0.1 to 15 parts by weight, and more preferably 0.1 to 5 parts by weight, based on 100 parts by weight of the copolymer. If the content is less than 0.1 part by weight, the cohesion force becomes small due to insufficient crosslinking degree, which may cause durability deterioration such as lifting and damage of cutting property. If the content is more than 15 parts by weight, problem of relaxation of residual stress may occur due to excessive crosslinking reaction. have.
상기와 같은 성분 이외에, 본 발명에 따른 점착제 조성물은 용도에 따라 요구되는 점착력, 응집력, 점성, 탄성률, 유리전이온도, 대전방지성 등을 조절하기 위하여, 점착성 부여 수지, 산화방지제, 부식방지제, 레벨링제, 표면윤활제, 염료, 안료, 소포제, 충전제, 광안정제, 대전방지제 등의 첨가제를 더 포함할 수 있다.In addition to the components as described above, the pressure-sensitive adhesive composition according to the present invention, in order to adjust the adhesion, cohesion, viscosity, elastic modulus, glass transition temperature, antistatic properties, etc. required according to the use, tackifying resin, antioxidant, corrosion inhibitor, leveling Agents may further include additives such as surface lubricants, dyes, pigments, antifoams, fillers, light stabilizers, antistatic agents and the like.
이와 같이 구성된 점착제 조성물은 특히 화학식 1로 표시되는 단량체가 중합된 공중합체를 포함함으로써 양생 기간을 단축시킴과 동시에 우수한 경시안정성을 갖는다. 또한, 점착력, 내열/내습열성 및 리워크성과 같은 물성도 만족시킬 수 있다.The pressure-sensitive adhesive composition thus constructed includes a copolymer in which the monomer represented by the general formula (1) is polymerized, thereby shortening the curing period and having excellent aging stability. In addition, physical properties such as adhesive strength, heat / humidity heat resistance, and rework property can also be satisfied.
본 발명의 점착제 조성물은 액정셀과의 접합을 위한 편광판용 점착제뿐만 아니라 표면보호필름용 점착제로서도 모두 사용할 수 있다. 또한, 보호필름, 반사시트, 구조용 점착시트, 사진용 점착시트, 차선표시용 점착시트, 광학용 점착제품, 전자부품용 점착제뿐만 아니라 일반 상업용 점착시트제품, 의료용 패치로도 사용 가능하다.The pressure-sensitive adhesive composition of the present invention can be used both as a pressure-sensitive adhesive for surface protection film as well as pressure-sensitive adhesive for polarizing plate for bonding with a liquid crystal cell. 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.
본 발명의 편광판은 점착제 조성물로 이루어진 점착제층이 적층된 것을 특징으로 한다.The polarizing plate of the present invention is characterized in that an adhesive layer made of an adhesive composition is laminated.
점착제층의 두께는 그 점착력에 따라 조절될 수 있으며, 통상 3 내지 100㎛인 것이 바람직하며, 보다 바람직하게는 10 내지 100㎛인 것이 좋다.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㎛.
이러한 편광판은 통상의 액정표시장치에 모두 적용 가능하며, 구체적으로 점착제층이 적층된 편광판을 액정셀의 적어도 한 면에 접합한 액정패널을 포함하는 액정표시장치를 구성할 수 있다.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.
이하, 본 발명의 이해를 돕기 위하여 바람직한 실시예를 제시하나, 이들 실시예는 본 발명을 예시하는 것일 뿐 첨부된 특허청구범위를 제한하는 것이 아니며, 본 발명의 범주 및 기술사상 범위 내에서 실시예에 대한 다양한 변경 및 수정이 가능함은 당업자에게 있어서 명백한 것이며, 이러한 변형 및 수정이 첨부된 특허청구범위에 속하는 것도 당연한 것이다.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.
합성예Synthetic example 1 One
1000mL 용량의 둥근플라스크를 60℃ 항온조에 담그고, 2-하이드록시에틸메타아크릴레이트 90g과 포타슘 카보네이트 0.5g 및 디클로로메탄 용매 300g을 첨가한 후, 4,4,4-트리플로로-3-옥소-부트릭 산 100g을 더 첨가하였다. 7시간 동안 교반한 뒤, 증류수 500mL를 추가하고 10분간 교반 후, 분별깔대기로 디클로로메탄층을 분리하고, 컬럼을 통하여 화학식2로 표시되는 화합물 150g을 얻었다.A 1000 mL volumetric flask was immersed in a 60 ° C. thermostat, 90 g of 2-hydroxyethyl methacrylate, 0.5 g of potassium carbonate, and 300 g of dichloromethane solvent were added, followed by 4,4,4-trifluoro-3-oxo- An additional 100 g of butric acid was added. After stirring for 7 hours, 500 mL of distilled water was added and stirred for 10 minutes. The dichloromethane layer was separated with a separatory funnel, and 150 g of the compound represented by Chemical Formula 2 was obtained through a column.
합성예Synthetic example 2 2
1000mL 용량의 둥근플라스크를 60℃ 항온조에 담그고, 2-하이드록시에틸메타아크릴레이트 100g과 포타슘 카보네이트 0.5g 및 디클로로메탄 용매 300g을 첨가한 후, 시아노 아크릴산 90g을 더 첨가하였다. 7시간 동안 교반한 뒤, 증류수 500mL를 추가하고 10분간 교반 후, 분별깔대기로 디클로로메탄층을 분리하고, 컬럼을 통하여 화학식3으로 표시되는 화합물 150g을 얻었다.A 1000 mL volumetric flask was immersed in a 60 ° C thermostat, 100 g of 2-hydroxyethyl methacrylate, 0.5 g of potassium carbonate, and 300 g of dichloromethane solvent were added, followed by further addition of 90 g of cyanoacrylic acid. After stirring for 7 hours, 500 mL of distilled water was added and stirred for 10 minutes. The dichloromethane layer was separated with a separatory funnel, and 150 g of the compound represented by Chemical Formula 3 was obtained through a column.
합성예Synthetic example 3 3
1000mL 용량의 둥근플라스크를 60℃ 항온조에 담그고, 2-하이드록시에틸메타아크릴레이트 90g과 포타슘 카보네이트 0.5g 및 디클로로메탄 용매 300g을 첨가한 후, 트리플로로메탄설폰닐아세트산 100g을 더 첨가하였다. 7시간 동안 교반한 뒤, 증류수 500mL를 추가하고 10분간 교반 후, 분별깔대기로 디클로로메탄층을 분리하고, 컬럼을 통하여 화학식4로 표시되는 화합물 150g을 얻었다.A 1000 mL volumetric flask was immersed in a 60 ° C. thermostat, 90 g of 2-hydroxyethyl methacrylate, 0.5 g of potassium carbonate, and 300 g of dichloromethane solvent were added, followed by further addition of trichloromethanesulfonyl acetic acid. After stirring for 7 hours, 500 mL of distilled water was added and stirred for 10 minutes. The dichloromethane layer was separated with a separatory funnel, and 150 g of the compound represented by Chemical Formula 4 was obtained through a column.
합성예Synthetic example 4 4
1000mL 용량의 둥근플라스크를 60℃ 항온조에 담그고, 2-메틸메타아크릴산 2-(2-하이드록시에톡시)에틸에스터 110g과 포타슘 카보네이트 0.5g 및 디클로로메탄 용매 300g을 첨가한 후, 시아노아세트산 90g을 더 첨가하였다. 7시간 동안 교반한 뒤, 증류수 500mL를 추가하고 10분간 교반 후, 분별깔대기로 디클로로메탄층을 분리하고, 컬럼을 통하여 화학식5로 표시되는 화합물 150g을 얻었다.A 1000 mL volumetric flask was immersed in a 60 ° C. thermostat, 110 g of 2- (2-hydroxyethoxy) ethyl ester, 0.5 g of potassium carbonate and 300 g of dichloromethane solvent were added, followed by 90 g of cyanoacetic acid. More was added. After stirring for 7 hours, 500 mL of distilled water was added and stirred for 10 minutes. The dichloromethane layer was separated with a separatory funnel, and 150 g of the compound represented by Formula 5 was obtained through a column.
실시예Example 1-6 및 1-6 and 비교예Comparative example 1-3 1-3
하기 표 1에 기재된 성분과 조성비로 공중합체 및 점착제 조성물을 제조하였다(단위: 중량%).To the copolymer and pressure-sensitive adhesive composition was prepared in the component and composition ratio shown in Table 1 (unit: wt%).
공중합체는 질소가스가 환류되고 온도조절이 용이하도록 냉각장치를 설치한 1 L의 반응기에 하기 표 1의 성분 및 조성비로 이루어진 단량체 혼합물을 투입한 후, 용제로 에틸아세테이트(EAc)를 단량체 혼합물과 동일한 중량으로 투입하였다. 그 다음 산소를 제거하기 위하여 질소가스를 1 시간 동안 퍼징한 후, 62 ℃로 유지하였다. 상기 혼합물을 균일하게 한 후, 반응개시제로 아조비 스이소부티로니트릴(AIBN)을 단량체 혼합물 100 중량부 대비 0.07 중량부로 투입하고, 8 시간 동안 반응시켜 제조하였다.In the copolymer, nitrogen monomer was refluxed, and a monomer mixture composed of the components and composition ratios of Table 1 was added to a 1 L reactor equipped with a cooling device to facilitate temperature control, and then ethyl acetate (EAc) was added to the monomer mixture as a solvent. Was added at the same weight. Then, after purging nitrogen gas for 1 hour to remove oxygen, it was maintained at 62 ℃. After the mixture was homogenized, azobis isobutyronitrile (AIBN) was added as 0.07 parts by weight based on 100 parts by weight of the monomer mixture as a reaction initiator, and reacted for 8 hours.
폴리머Base
Polymer
AA : 아크릴산
2HEA : 2-하이드록시에틸아크릴레이트
Cor-L : 코로네이트-L(니혼폴리우레탄코교주식회사 제품)
Cor-HXR : 코로네이트-HXR(니혼폴리우레탄코교주식회사 제품)BA: Butyl acrylate
AA: acrylic acid
2HEA: 2-hydroxyethyl acrylate
Cor-L: Coronate-L (product of Nippon Polyurethane Co., Ltd.)
Cor-HXR: Coronate-HXR (product of Nippon Polyurethane Co., Ltd.)
실험예Experimental Example
상기 표 1에 따라 제조된 실시예 1-6과 비교예 1-3의 점착제 조성물 용액을 박리필름에 코팅하여 건조한 후 25 ㎛가 되도록 도포하고, 100℃ 1분간 건조시켜, 점착제 조성물로 이루어진 점착층을 형성하였다. The pressure-sensitive adhesive composition of Example 1-6 and Comparative Example 1-3 prepared according to Table 1 was coated on a release film and dried to apply to 25 ㎛, dried at 100 ℃ 1 minute, the pressure-sensitive adhesive layer made of pressure-sensitive adhesive composition Formed.
상기 제조된 점착층을 185 ㎛ 두께의 요오드계 편광판에 점착가공한 후, 충분한 숙성과정을 위하여 23 ℃의 온도와 60%의 습도조건에서 양생일 동안 보관하여 실시예 1-6와 비교예 1-3에 해당하는 편광판을 얻었다. The pressure-sensitive adhesive layer prepared on the 185 μm-thick iodine-based polarizing plate was then adhesively stored and stored for 2 days at a temperature of 23 ° C. and 60% humidity for curing. Example 1-6 and Comparative Example 1- The polarizing plate corresponding to 3 was obtained.
얻어진 편광판은 적절한 크기로 절단하여 하기 평가에 사용하였으며, 그 결과를 하기 표 2에 기재하였다.The obtained polarizing plate was cut to an appropriate size and used for the following evaluation, and the results are shown in Table 2 below.
1. 내열/1. Heat resistant / 내습열Wet heat 신뢰성 responsibility
시험예 1에서 제조한 점착제 시트로부터 이형필름을 박리한 후, 두께 185㎛의 요오드계 편광판에 점착 가공하였다. 상기의 편광판을 90mmX170mm로 절단하고 유리기판 (110mm X 190mm X 0.7mm)에 양면으로 광학 흡수축이 크로스된 상태로 부착시켰다. 이때 가해진 압력은 5kg/cm2으로 기포나 이물이 생기지 않도록 크린룸 작업을 하였다. 이 시편들을 내열특성은 80℃의 온도에서 1000시간 동안 방치한 후에 기포나 박리의 발생 여부를 관찰하였다. 시편의 상태를 평가하기 직전에 상온에서 24시간 방치한 후 실시하였다. 내습열 특성을 파악하기 위하여 60℃의 온도 및 90%의 상대습도 조건하에서 1000시간 방치한 후에 기포나 박리의 발생 여부를 관찰하였다. 또한, 상기에서 제조된 점착 편광판을 5개월 이상 방치 후 상기의 방법으로 신뢰성을 평가하였다. 신뢰성에 대한 평가기준은 다음과 같다.After peeling a release film from the adhesive sheet manufactured in the test example 1, it carried out the adhesion process to the iodine type polarizing plate of thickness 185 micrometers. The polarizing plate was cut into 90 mm × 170 mm and attached to a glass substrate (110 mm × 190 mm × 0.7 mm) with the optical absorption axis crossed on both sides. At this time, the pressure applied was 5kg / cm 2 to clean room to prevent bubbles or foreign matter. Heat resistance of these specimens was observed for 1000 hours at a temperature of 80 ℃ after the bubble or peeling was observed. The specimens were allowed to stand at room temperature for 24 hours immediately before evaluating the state of the specimens. In order to understand the heat and moisture resistance, bubbles and peeling were observed after being left for 1000 hours at a temperature of 60 ° C. and a relative humidity of 90%. In addition, after leaving the pressure-sensitive adhesive polarizing plate prepared for 5 months or more, the reliability was evaluated by the above method. The evaluation criteria for reliability are as follows.
<평가기준><Evaluation Criteria>
ⓞ: 기포나 박리 없음Ⓞ: no bubbles or peeling
○: 기포나 박리 5개미만○: less than 5 bubbles or peeling
△: 기포나 박리 5개이상 10개미만△: less than 10 or more bubbles or peeling
×: 기포나 박리 10개이상×: 10 or more bubbles or peelings
2. 점착력 측정2. Adhesion measurement
점착제 시트를 폭 25mm, 길이 100mm의 크기로 잘라내고, 이형필름을 박리한 후, 트리아세틸셀룰로오스(보호필름)와 폴리비닐알코올(편광자)로 구성된 편광판에 0.25 MPa의 압력으로 라미네이션하고 오토클레이브를 처리하여 평가 샘플을 제조하였다.The pressure-sensitive adhesive sheet is cut into a width of 25 mm and a length of 100 mm, the release film is peeled off, and then laminated on a polarizing plate made of triacetyl cellulose (protective film) and polyvinyl alcohol (polarizer) at a pressure of 0.25 MPa and the autoclave is treated. To prepare an evaluation sample.
제조한 샘플을 23℃ X 50% RH의 환경하에서 24시간 방치한 샘플과, 50℃ X 50% RH의 환경하에서 48시간 방치한 샘플을 UTM (만능인장시험기, Instron)을 사용하여 박리 속도 10 m / min, 박리각도 180°로 박리할 때의 점착력을 측정하였다. 측정은 23℃ X 50% RH의 환경하에서 실시하였다.Peeling rate 10 m using a UTM (Universal Tensile Tester, Instron) was used to prepare the samples left for 24 hours in a 23 ℃ X 50% RH environment and a sample left for 48 hours in a 50 ℃ X 50% RH environment Adhesion at peeling at / min and a peeling angle of 180 ° was measured. The measurement was carried out in an environment of 23 ° C. X 50% RH.
3. 3. 리워크성Reworkability 측정 Measure
편광판을 폭 25mm, 길이 100mm의 크기로 잘라내고, 이형필름을 박리한 후, 코닝사 #1737 유리에 0.25 MPa의 압력으로 라미네이션하고 5기압, 50℃의 조건으로 20분 동안 오토클레이브를 처리하여 평가 샘플을 제조하였다. 내열조건인 80℃ 오븐에 넣은 후 10시간 뒤 꺼내어 120시간 상온 방치 후 1.3cm/s의 속도로 박리하고, 내습조건인 60℃, 90RH% 오븐에 넣은 후 12시간 뒤 꺼내어 120시간 상온 방치 후 1.3cm/s 의 속도로 박리하였다.The polarizing plate was cut out to a size of 25 mm in width and 100 mm in length, the release film was peeled off, and then laminated to Corning's # 1737 glass at a pressure of 0.25 MPa, and the autoclave was treated at 5 atmospheres and 50 ° C. for 20 minutes. Was prepared. After putting it in the oven at 80 ℃ for heat condition and taking it out after 10 hours, it was peeled at a speed of 1.3cm / s after being left at room temperature for 120 hours. Peeling was carried out at a speed of cm / s.
○: 양쪽 조건 모두에서 유리 기판에 점착제의 남음이 없고 편광판의 찢어짐 없이 깨끗이 박리(Circle): There is no adhesive left in a glass substrate in both conditions, and peeling is clean without tearing of a polarizing plate.
×: 어느 한쪽 조건 이상에서 패널에 점착제가 남아있거나 박리과정에서 편광판이 찢어짐X: The adhesive remains on the panel under any one condition or the polarizing plate is torn during the peeling process
4. 4. 겔분율Gel fraction
제조된 점착제 부착 편광판을 23℃ 65%RH에서 3일 동안 양생하였다. 정칭(精秤)한 250메쉬의 철망(100㎜×100㎜)에 양생된 점착제 부착 편광판의 점착제층을 약 0.25g 첩부하고, 겔분이 새어나가지 않도록 감싼다. 정밀 천칭으로 중량을 정확하게 측정한 후, 철망을 에틸아세테이트 용액에 3일간 침지한다. 침지된 철망을 꺼내어 소량의 에틸아세테이트 용액으로 세정하고, 120℃에서 4시간 건조한 후 중량을 측정한다. 측정된 중량을 이용하여 하기 수학식 1로 겔분율을 계산하였다.The prepared pressure-sensitive adhesive polarizing plate was cured at 23 ° C. 65% RH for 3 days. About 0.25 g of the pressure-sensitive adhesive layer of the pressure-sensitive adhesive polarizing plate cured on a regular 250 mesh wire mesh (100 mm x 100 mm) is affixed and wrapped so that the gel powder does not leak out. After precisely weighing by precision balance, the wire mesh is immersed in ethyl acetate solution for 3 days. The immersed wire mesh is taken out, washed with a small amount of ethyl acetate solution, dried at 120 ° C. for 4 hours, and weighed. The gel fraction was calculated by the following equation 1 using the measured weight.
[식 중, A는 철망의 중량(g), B는 점착제층을 첩부한 철망의 중량(점착제 중량, g), C는 침지 후 건조한 철망의 중량(겔화된 수지의 중량, g)임)].[Wherein A is the weight of the wire mesh (g), B is the weight of the wire mesh with the adhesive layer (adhesive weight, g), and C is the weight of the dry wire mesh after immersion (weight of the gelled resin, g)) .
25℃ 24hrRoom temperature adhesion
25 ℃ 24hr
50℃ 48hrWarm adhesion
50 ℃ 48hr
상기 표 2에 기재된 바와 같이, 실시예들의 점착제 조성물에 비하여, 비교예들의 점착제 조성물은 내열성/내습열성이 저하되는 것을 알 수 있다.As shown in Table 2, compared to the pressure-sensitive adhesive composition of the embodiments, it can be seen that the pressure-sensitive adhesive composition of the comparative examples is reduced in heat resistance / heat-and-moisture resistance.
또한, 점착제 조성물의 양생시간 단축효과는 3일차 겔분율로 평가할 수 있는데, 실시예들의 점착제 조성물은 내열성/내습열성 등과 함께 겔분율도 비교예들에 비해 우수한 것을 알 수 있다.
In addition, the curing time shortening effect of the pressure-sensitive adhesive composition can be evaluated by the 3rd day gel fraction, it can be seen that the pressure-sensitive adhesive composition of the embodiments together with the heat resistance / moisture heat resistance and the like, the gel fraction is also superior to the comparative examples.
Claims (12)
[화학식 1]
(식 중, R1은 수소 또는 메틸기이며, R2는 -CN, -NO2, -COCF3, -SO2CF3 , -Ph-CN 또는 -Ph-NO2이며, n은 1 내지 4의 정수임).
An acrylic copolymer comprising a repeating unit formed of a monomer represented by Formula 1 below:
[Formula 1]
(Wherein R 1 is hydrogen or methyl group, R 2 is —CN, —NO 2 , —COCF 3 , —SO 2 CF 3 , —Ph-CN or —Ph-NO 2 , n is 1-4); Integer).
The copolymer according to claim 1, wherein the copolymer is formed by copolymerization of a (meth) acrylate monomer containing an alkyl group having 1 to 12 carbon atoms and a monomer represented by the formula (1).
The copolymer according to claim 2, wherein the copolymer is formed by polymerizing 100 parts by weight of a (meth) acrylate monomer containing an alkyl group having 1 to 12 carbon atoms and 0.01 to 10 parts by weight of the monomer represented by Formula 1.
The method according to claim 1, wherein the (meth) acrylate monomers are methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth ) Acrylate, 2-butyl (meth) acrylate, t-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, 2-ethylbutyl (meth) acrylate, pentyl (meth) acrylate, n -Octyl (meth) acrylate, isooctyl (meth) acrylate, n-nonyl (meth) acrylate, isononyl (meth) acrylate, decyl (meth) acrylate and lauryl (meth) acrylate At least one copolymer selected from.
The copolymer according to claim 1, further comprising a monomer having a crosslinkable functional group.
The copolymer according to claim 5, wherein the crosslinkable functional group is a hydroxy group, a carboxy group, an amide group or a tertiary amine group.
The copolymer of claim 5, wherein the monomer having a crosslinkable functional group is included in an amount of 0.1 to 15% by weight based on the total weight of the monomers.
The copolymer of claim 1 wherein the weight average molecular weight is 200,000 to 1.5 million.
An adhesive composition comprising the copolymer of any one of claims 1 to 8 and a crosslinking agent.
The pressure-sensitive adhesive composition of claim 9, 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 copolymer solids.
Polarizing plate with a pressure-sensitive adhesive layer formed of the pressure-sensitive adhesive composition of claim 9.
Liquid crystal display device provided with a polarizing plate of claim 11.
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| WO2018182120A1 (en) * | 2017-03-31 | 2018-10-04 | 동우화인켐 주식회사 | Polarizing plate and image display device comprising same |
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| WO2018159921A1 (en) * | 2017-02-28 | 2018-09-07 | 동우화인켐 주식회사 | Adhesive composition, polarization plate comprising same, and image display device |
| WO2018182120A1 (en) * | 2017-03-31 | 2018-10-04 | 동우화인켐 주식회사 | Polarizing plate and image display device comprising same |
| KR20180111227A (en) * | 2017-03-31 | 2018-10-11 | 동우 화인켐 주식회사 | Polarizing plate and image display device comprising the same |
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