WO2014021622A1 - Adhesive composition - Google Patents

Adhesive composition Download PDF

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Publication number
WO2014021622A1
WO2014021622A1 PCT/KR2013/006868 KR2013006868W WO2014021622A1 WO 2014021622 A1 WO2014021622 A1 WO 2014021622A1 KR 2013006868 W KR2013006868 W KR 2013006868W WO 2014021622 A1 WO2014021622 A1 WO 2014021622A1
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WIPO (PCT)
Prior art keywords
weight
pressure
sensitive adhesive
adhesive composition
parts
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PCT/KR2013/006868
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French (fr)
Korean (ko)
Inventor
최한영
허지혜
Original Assignee
동우화인켐 주식회사
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Priority claimed from KR1020130090172A external-priority patent/KR20140019229A/en
Application filed by 동우화인켐 주식회사 filed Critical 동우화인켐 주식회사
Publication of WO2014021622A1 publication Critical patent/WO2014021622A1/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02Non-macromolecular additives
    • C09J11/06Non-macromolecular additives organic
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00Adhesives 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
    • C09J133/04Homopolymers or copolymers of esters
    • C09J133/06Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/08Homopolymers or copolymers of acrylic acid esters
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2203/00Applications
    • C08L2203/20Applications use in electrical or conductive gadgets

Definitions

  • the present invention relates to a pressure-sensitive adhesive composition which can be applied to an organic solvent system while having a corrosion preventing function of a metal.
  • a liquid crystal display device includes a liquid crystal cell and a polarizing plate containing liquid crystal, and various optical films (phase difference plate, viewing angle magnification film, Brightness enhancement film, etc.) is used.
  • Such a polarizing plate and an optical film are bonded to a liquid crystal cell using an adhesive.
  • the pressure sensitive adhesive is often used an acrylic pressure sensitive adhesive based on an acrylic polymer having excellent adhesion and transparency.
  • Crosslinking of the acrylic pressure sensitive adhesive utilizes a bond between a crosslinking agent and a functional monomer of an acrylic polymer.
  • the liquid crystal cell including a metal layer such as ITO is corroded by H 2 O and O 2 contained in the pressure-sensitive adhesive to form metal oxides, hydroxides and other corrosive products. These may reduce the electrical or mechanical stability of the liquid crystal display, or may cause problems in securing visibility and reliability.
  • this problem may be exacerbated when exposed to high temperature and high humidity environments.
  • Corrosion inhibitors include azo compounds (Korean Patent Publication No. 2010-31111), monomers containing carboxyl groups (Korean Patent No. 671,356), and compounds containing at least one atom such as phosphorus, sulfur, nitrogen, or oxygen ( Korean Patent No. 1,047,925) and the like.
  • the double phosphorus compound is used as a corrosion inhibitor in various fields, but it is usually dissolved in water, and thus there is a limit in the field of use thereof. In particular, there is a problem that cannot be used in the electric / electronic field, such as a liquid crystal display device that restricts the use of water.
  • An object of the present invention is to provide a pressure-sensitive adhesive composition which can suppress corrosion of a metal layer while exhibiting excellent solubility in an organic solvent using a specific compound having a phosphoric acid functional group.
  • the present invention provides a pressure-sensitive adhesive composition containing a compound of formula (1).
  • R 1 is hydrogen or a methyl group
  • R 2 is an alkyl group having 1 to 10 carbon atoms
  • X is an integer of 1 to 10
  • n is an integer of 1 to 2).
  • Formula 1 may be R 2 is an alkyl group having 1 to 4 carbon atoms and X may be an integer of 1 to 6.
  • the pressure-sensitive adhesive composition may contain an acrylic copolymer and a compound of Formula 1.
  • the compound of Formula 1 may contain 1 to 20 parts by weight based on 100 parts by weight of the acrylic copolymer.
  • the pressure-sensitive adhesive composition may contain an acrylic copolymer copolymerized with the compound of Formula 1.
  • the acrylic copolymer may contain a (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms, a polymerizable monomer having a crosslinkable functional group, and a compound of Formula 1.
  • the compound of Formula 1 may contain 1 to 20 parts by weight based on 100 parts by weight of the (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms.
  • the acrylic copolymer may have a weight average molecular weight (polystyrene equivalent, Mw) of 50,000 to 2 million.
  • the pressure-sensitive adhesive composition may contain an acrylic copolymer copolymerized with a compound of Formula 1, and a compound of Formula 1.
  • the pressure-sensitive adhesive composition of the present invention has the advantage of being excellent in solubility in organic solvents and at the same time effectively suppressing corrosion of the metal layer.
  • the pressure-sensitive adhesive composition of the present invention is not only excellent in adhesive force with the metal layer, but also has an advantage of excellent adhesive durability under high temperature or high temperature and high humidity conditions.
  • the pressure-sensitive adhesive composition is expected to have high utility in the field of electrical / electronic components, which require much bonding of metals or metal oxide semiconductors.
  • the present invention relates to a pressure-sensitive adhesive composition which can be applied to an organic solvent system while having a corrosion preventing function of a metal.
  • the pressure-sensitive adhesive composition of the present invention contains a compound of formula (1).
  • R 1 is hydrogen or a methyl group
  • R 2 is an alkyl group having 1 to 10 carbon atoms
  • X is an integer of 1 to 10
  • n is an integer of 1 to 2).
  • R ⁇ 2> is a C1-C4 alkyl group and X is an integer of 1-6.
  • the compound of Formula 1 may effectively inhibit corrosion of the metal layer by chemically reacting with the metal surface to form a kind of protective film (corrosion preventing film).
  • the compound is absorbed by the metal surface to form a stable protective film on the adhesive interface to prevent water from acting on the surface of the metal layer can suppress corrosion.
  • compounds containing phosphoric acid such as the compound of Formula 1
  • Such compounds of formula (1) may be used synthetic or commercially available products.
  • the PAM series by RHODIA company can be used as an example.
  • PAM100 and PAM200 are preferred because of their excellent compatibility with polar organic solvents.
  • the pressure-sensitive adhesive composition of the present invention may contain an acrylic copolymer copolymerized by containing the compound of formula (1).
  • the compound of Formula 1 is used as a component of the monomer forming the acrylic copolymer.
  • the acryl-type copolymer of this invention contains the (meth) acrylate monomer which has a C1-C12 alkyl group, the polymerizable monomer which has a crosslinkable functional group, and the compound of General formula (1).
  • (meth) acrylate means acrylate and methacrylate.
  • Examples of the (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms include n-butyl (meth) acrylate, 2-butyl (meth) acrylate, t-butyl (meth) acrylate, and 2-ethylhexyl (meth).
  • the polymerizable monomer having a crosslinkable functional group serves to provide durability and cutability by reinforcing the cohesive force or adhesive strength of the pressure-sensitive adhesive composition by chemical bonding.
  • the monomer which has a hydroxyl group, the monomer which has a carboxy group, the monomer which has an amide group, the monomer which has a tertiary amine group, etc. are mentioned, These can be used individually or in mixture of 2 or more types.
  • 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 to 3 carbon atoms of an alkyl group, and among these, (meth) acrylic acid is preferable.
  • (meth) acrylic acid 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) acrylate, etc. are mentioned.
  • the polymerizable monomer which has such a crosslinkable functional group is contained in 0.05-10 weight part with respect to 100 weight part of (meth) acrylate monomers which have a C1-C12 alkyl group, More preferably, it is 0.1-8 weight part good. If the content is less than 0.05 parts by weight, the cohesive force of the pressure-sensitive adhesive may be reduced, the durability may be lowered. If the content is more than 10 parts by weight, the adhesive strength is lowered by a high gel fraction may cause problems in durability.
  • the compound of Formula 1 is preferably contained in 1 to 20 parts by weight, more preferably 2 to 10 parts by weight based on 100 parts by weight of the (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms. If the content is less than 1 part by weight, the corrosion protection effect may be insignificant, and when it contains 20 parts by weight, there is a problem in that the adhesive force is too high to reduce reworkability.
  • the acrylic copolymer may further contain other polymerizable monomers in addition to the above monomers in a range of not lowering the adhesive strength, for example, 10 parts by weight or less based on the total amount.
  • 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.
  • 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.
  • Mw polystyrene equivalent
  • the pressure-sensitive adhesive composition of the present invention may further contain a crosslinking agent.
  • a crosslinking agent can improve adhesiveness and durability, and can maintain the reliability and shape of an adhesive at high temperature.
  • the crosslinking agent may be an isocyanate type, an epoxy type, a melamine type, a peroxide type, a metal chelate type, an oxazoline type, or the like, and one or two or more kinds thereof may be used. Double isocyanate type or epoxy type is preferred.
  • the isocyanate type is tolylene diisocyanate, xylene diisocyanate, 2,4-diphenylmethane diisocyanate, 4,4-diphenylmethane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, tetramethyl xylene diisocyanate, naphthalenedi Diisocyanate compounds such as isocyanate; 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 mo
  • Examples of the melamine type include hexametholol melamine, hexamethoxymethyl melamine, hexabutoxymethyl melamine, and the like.
  • Such a crosslinking agent may be contained in an amount of 0.1 to 15 parts by weight, preferably 0.3 to 5 parts by weight, based on 100 parts by weight of the acrylic copolymer. If the content is less than 0.1 part by weight, the cohesive force may be reduced due to insufficient crosslinking degree, thereby impairing the adhesive durability and the cleavage property. 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 of the present invention may contain an acrylic copolymer and the compound of Formula 1.
  • the compound of Formula 1 is used as a component of an additive of the pressure-sensitive adhesive composition.
  • the compound of Formula 1 is preferably contained in 1 to 20 parts by weight, more preferably 2 to 15 parts by weight with respect to 100 parts by weight of the acrylic copolymer. If the content is less than 1 part by weight, the anti-corrosion effect may be insignificant, and if it exceeds 20 parts by weight, the adhesive force may be too high to reduce reworkability (reworkability).
  • the pressure-sensitive adhesive composition of the present invention may contain an acrylic copolymer copolymerized by containing a compound of Formula 1, and a compound of Formula 1.
  • Formula 1 is used as an additive component of the pressure-sensitive adhesive composition at the same time as the component to form an acrylic copolymer.
  • the compound of Formula 1 contained in the acrylic copolymer may be included in an amount of 1 to 10 parts by weight based on 100 parts by weight of the (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms.
  • the compound of Formula 1 used as an additive of the pressure-sensitive adhesive composition may be included in 1 to 10 parts by weight based on 100 parts by weight of the acrylic copolymer.
  • the pressure-sensitive adhesive composition may further contain a crosslinking agent, and the type, content and physical properties of the acrylic copolymer and the crosslinking agent are the same as mentioned above.
  • the pressure-sensitive adhesive composition is a silane coupling agent, tackifying resin, antioxidant, leveling agent, surface lubricant, dye, in order to adjust the adhesion, cohesion, viscosity, elastic modulus, glass transition temperature, etc.
  • Additives such as a pigment, an antifoamer, a filler, a light stabilizer, an antistatic agent, can be further contained.
  • the double silane coupling agent serves to improve the adhesion between the pressure-sensitive adhesive and the base material, it is preferable to contain it. Can be used.
  • the silane coupling agent may contain 0.1 to 2 parts by weight based on 100 parts by weight of the acrylic copolymer in consideration of adhesion and durability. have.
  • the pressure-sensitive adhesive composition of the present invention can be used as a pressure-sensitive adhesive for polarizing plates and a surface protective film for bonding to liquid crystal cells.
  • it can be used as a general commercial adhesive sheet product as well as a protective film, a reflective sheet, a structural adhesive sheet, a photographic adhesive sheet, a lane marking adhesive sheet, an optical adhesive product, an adhesive for electronic parts, and the like.
  • n-butyl acrylate BA
  • MA methyl acrylate
  • 2-hydroxyethyl acrylate 2.0 85 parts by weight of n-butyl acrylate (BA), 7 parts by weight of methyl acrylate (MA), 2-hydroxyethyl acrylate 2.0 in a 1 L reactor equipped with a refrigeration system to facilitate nitrogen temperature reflux and temperature control.
  • monomer mixture consisting of parts by weight, 1.0 part by weight of acrylic acid and 5.0 parts by weight of PAM200 product (Rhodia)
  • 100 parts by weight of acetone was added as a solvent. Then, after purging nitrogen gas for 1 hour to remove oxygen, it was maintained at 62 ° C.
  • AIBN azobisisobutyronitrile
  • An acrylic copolymer F having a weight average molecular weight of about 1 million was prepared in the same manner as in Preparation Example 1, but using PAM100 (Rhodia) instead of PAM200 (Rhodia).
  • a monomer mixture consisting of 90 parts by weight of n-butyl acrylate (BA), 7 parts by weight of methyl acrylate (MA), 2.0 parts by weight of 2-hydroxyethyl acrylate, and 1.0 parts by weight of acrylic acid was carried out in the same manner as in Preparation Example 1.
  • the pressure-sensitive adhesive composition prepared above was applied on a release film coated with a silicone release agent to have a thickness of 25 ⁇ m, and dried at 100 ° C. for 1 minute to form an adhesive layer.
  • a pressure-sensitive adhesive polarizing plate was prepared by laminating the pressure-sensitive adhesive layer prepared above on an iodine-based polarizing plate having a thickness of 185 ⁇ m.
  • the prepared polarizing plate was stored under curing conditions at 23 ° C. and 60% RH.
  • the release film of the polarizing plate with pressure-sensitive adhesive was peeled off, the surface of the pressure-sensitive adhesive layer and the aluminum plate were bonded together, and left to stand for 250 hours at 60 ° C. and 95% RH% to prepare a laminate specimen.
  • the adhesive layer was peeled from the said laminated body, the surface of the aluminum plate which contacted the said adhesive layer was visually observed, and the presence or absence of corrosion was evaluated.
  • the surface of the aluminum plate is not corroded at all: ⁇
  • the polarizing plate was peeled from the said laminated body at the speed
  • the laminate specimen was stored for 300 hours under a drying condition at a temperature of 80 ° C., and then the appearance was confirmed (heat test).
  • Bubble and exfoliation are admitted but less than 3 are admitted: ⁇
  • the polarizing plate was cut out to a width of 25 mm and a length of 100 mm, 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. Evaluation samples were prepared. After putting it in an oven at 80 ° C., which was heat-resistant, it was taken out after 10 hours, left at room temperature for 120 hours, and then peeled at a speed of 1.3 cm / s. In addition, after being put into an oven at 60 ° C. and 90 RH% of humidity conditions, it was taken out after 12 hours, and left at room temperature for 120 hours, followed by peeling at a speed of 1.3 cm / s.
  • the adhesive remains on the panel under more than one condition or the polarizer is torn during the peeling process: ⁇
  • the pressure-sensitive adhesive composition of Examples 1 to 14 containing the compound of Formula 1 according to the present invention is superior in corrosion resistance, adhesive strength and adhesive durability (heat resistance conditions) of the metal layer at the same time compared to Comparative Examples 1 to 2 I could confirm that.

Abstract

The present invention relates to an adhesive composition and, more specifically, to an adhesive composition which contains a specific compound as an additive component thereof, or as a component of a copolymer contained in the adhesive composition, thus having excellent solubility in an organic solvent, effectively inhibiting the corrosion of a metal layer, and having excellent adhesive durability with the metal layer under severe conditions (high temperature and high humidity).

Description

점착제 조성물Pressure-sensitive adhesive composition
본 발명은 유기용매계에 적용이 가능하면서 금속의 부식방지 기능을 갖는 점착제 조성물에 관한 것이다.The present invention relates to a pressure-sensitive adhesive composition which can be applied to an organic solvent system while having a corrosion preventing function of a metal.
일반적으로 액정표시장치(Liquid crystal display device, LCD)는 액정을 포함하고 있는 액정셀과 편광판이 구비되며, 상기 액정표시장치의 표시 품위를 향상시키기 위하여 여러 가지 광학필름(위상차판, 시야각 확대필름, 휘도 향상필름 등)이 사용된다. In general, a liquid crystal display device (LCD) includes a liquid crystal cell and a polarizing plate containing liquid crystal, and various optical films (phase difference plate, viewing angle magnification film, Brightness enhancement film, etc.) is used.
이러한 편광판 및 광학필름은 점착제를 사용하여 액정셀에 접합한다. 점착제는 접착성 및 투명성이 우수한 아크릴계 중합체를 베이스로 하는 아크릴계 점착제가 많이 사용된다. 아크릴계 점착제의 가교는 가교제와 아크릴계 중합체의 관능성 단량체와의 결합을 이용한다. Such a polarizing plate and an optical film are bonded to a liquid crystal cell using an adhesive. The pressure sensitive adhesive is often used an acrylic pressure sensitive adhesive based on an acrylic polymer having excellent adhesion and transparency. Crosslinking of the acrylic pressure sensitive adhesive utilizes a bond between a crosslinking agent and a functional monomer of an acrylic polymer.
그러나, ITO 등의 금속층을 포함하는 액정셀은 점착제 내부에 함유된 H2O 및 O2에 의해 부식이 발생되어 금속 산화물, 수산화물, 기타 부식성 생성물이 형성된다. 이들은 액정표시장치의 전기적 또는 기계적 안정성을 저하시키거나 시인성 확보 및 신뢰성에 문제를 발생시킬 수 있다.However, the liquid crystal cell including a metal layer such as ITO is corroded by H 2 O and O 2 contained in the pressure-sensitive adhesive to form metal oxides, hydroxides and other corrosive products. These may reduce the electrical or mechanical stability of the liquid crystal display, or may cause problems in securing visibility and reliability.
특히, 이러한 문제는 고온 및 다습한 환경에 노출된 경우 더욱 악화될 수 있다.In particular, this problem may be exacerbated when exposed to high temperature and high humidity environments.
금속의 부식성을 개선하기 위하여, 점착제 조성물에 다양한 부식방지제를 사용하는 방법이 공지되어 있다. 부식방지제로는 아조화합물(한국공개특허 제2010-31111호), 카르복시기를 함유한 단량체(한국등록특허 제671,356호) 및 인, 황, 질소, 또는 산소 등의 원자를 적어도 하나 이상 함유하는 화합물(한국등록특허 제1,047,925호) 등이 제시되어 있다.In order to improve the corrosiveness of metals, methods of using various preservatives in the pressure-sensitive adhesive composition are known. Corrosion inhibitors include azo compounds (Korean Patent Publication No. 2010-31111), monomers containing carboxyl groups (Korean Patent No. 671,356), and compounds containing at least one atom such as phosphorus, sulfur, nitrogen, or oxygen ( Korean Patent No. 1,047,925) and the like.
이중 인계 화합물은 다양한 분야에서 부식방지제로 사용되고 있으나 통상 물에 용해되므로 그 사용 분야가 제한되는 한계가 있다. 특히 물의 사용을 제한하고 있는 액정표시장치 등의 전기/전자 분야에서는 사용할 수 없는 문제가 있다.The double phosphorus compound is used as a corrosion inhibitor in various fields, but it is usually dissolved in water, and thus there is a limit in the field of use thereof. In particular, there is a problem that cannot be used in the electric / electronic field, such as a liquid crystal display device that restricts the use of water.
본 발명은 인산 작용기를 갖는 특정의 화합물을 사용하여, 유기용매에 대하여 우수한 용해성을 나타내면서 동시에 금속층의 부식을 억제할 수 있는 점착제 조성물을 제공하는 데 그 목적이 있다.An object of the present invention is to provide a pressure-sensitive adhesive composition which can suppress corrosion of a metal layer while exhibiting excellent solubility in an organic solvent using a specific compound having a phosphoric acid functional group.
상기한 목적을 달성하기 위하여, 본 발명은 하기 화학식 1의 화합물을 함유하는 점착제 조성물을 제공한다.In order to achieve the above object, the present invention provides a pressure-sensitive adhesive composition containing a compound of formula (1).
[화학식 1][Formula 1]
Figure PCTKR2013006868-appb-I000001
Figure PCTKR2013006868-appb-I000001
(상기 식 중, R1은 수소 또는 메틸기이고, R2는 탄소수 1 내지 10의 알킬기이고, X는 1 내지 10의 정수이며, n은 1 내지 2의 정수임).(Wherein R 1 is hydrogen or a methyl group, R 2 is an alkyl group having 1 to 10 carbon atoms, X is an integer of 1 to 10, and n is an integer of 1 to 2).
바람직하기로, 상기 화학식 1은 R2가 탄소수 1 내지 4의 알킬기이고 X는 1 내지 6의 정수일 수 있다. Preferably, Formula 1 may be R 2 is an alkyl group having 1 to 4 carbon atoms and X may be an integer of 1 to 6.
상기 점착제 조성물은 아크릴계 공중합체 및 화학식 1의 화합물을 함유할 수 있다.The pressure-sensitive adhesive composition may contain an acrylic copolymer and a compound of Formula 1.
상기 화학식 1의 화합물은 아크릴계 공중합체 100중량부에 대하여 1 내지 20중량부를 함유할 수 있다.The compound of Formula 1 may contain 1 to 20 parts by weight based on 100 parts by weight of the acrylic copolymer.
상기 점착제 조성물은 화학식 1의 화합물을 함유하여 공중합된 아크릴계 공중합체를 함유할 수 있다.The pressure-sensitive adhesive composition may contain an acrylic copolymer copolymerized with the compound of Formula 1.
상기 아크릴계 공중합체는 탄소수 1-12의 알킬기를 갖는 (메타)아크릴레이트 단량체, 가교 가능한 관능기를 갖는 중합성 단량체, 및 화학식 1의 화합물을 함유할 수 있다.The acrylic copolymer may contain a (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms, a polymerizable monomer having a crosslinkable functional group, and a compound of Formula 1.
상기 화학식 1의 화합물은 탄소수 1-12의 알킬기를 갖는 (메타)아크릴레이트 단량체 100중량부에 대하여, 1 내지 20중량부를 함유할 수 있다.The compound of Formula 1 may contain 1 to 20 parts by weight based on 100 parts by weight of the (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms.
상기 아크릴계 공중합체는 중량평균분자량(폴리스티렌 환산, Mw)이 5만 내지 200만일 수 있다.The acrylic copolymer may have a weight average molecular weight (polystyrene equivalent, Mw) of 50,000 to 2 million.
상기 점착제 조성물은 화학식 1의 화합물을 함유하여 공중합된 아크릴계 공중합체, 및 화학식 1의 화합물을 함유할 수 있다.The pressure-sensitive adhesive composition may contain an acrylic copolymer copolymerized with a compound of Formula 1, and a compound of Formula 1.
본 발명의 점착제 조성물은 유기용매에 대한 용해성이 우수하면서 동시에 금속층의 부식을 효과적으로 억제할 수 있는 이점이 있다. The pressure-sensitive adhesive composition of the present invention has the advantage of being excellent in solubility in organic solvents and at the same time effectively suppressing corrosion of the metal layer.
또한, 본 발명의 점착제 조성물은 금속층과의 점착력이 우수할 뿐만 아니라, 고온 또는 고온 다습한 조건하에서의 점착 내구성이 우수한 이점이 있다. In addition, the pressure-sensitive adhesive composition of the present invention is not only excellent in adhesive force with the metal layer, but also has an advantage of excellent adhesive durability under high temperature or high temperature and high humidity conditions.
따라서, 상기 점착제 조성물은 금속 또는 금속산화물 반도체 등의 접합이 많이 요구되는 전기/전자 부품 분야에서 그 활용도가 높을 것으로 예상된다.Therefore, the pressure-sensitive adhesive composition is expected to have high utility in the field of electrical / electronic components, which require much bonding of metals or metal oxide semiconductors.
본 발명은 유기용매계에 적용이 가능하면서 금속의 부식방지 기능을 갖는 점착제 조성물에 관한 것이다.The present invention relates to a pressure-sensitive adhesive composition which can be applied to an organic solvent system while having a corrosion preventing function of a metal.
이하 본 발명을 상세히 설명하면 다음과 같다.Hereinafter, the present invention will be described in detail.
본 발명의 점착제 조성물은 하기 화학식 1의 화합물을 함유한다.The pressure-sensitive adhesive composition of the present invention contains a compound of formula (1).
[화학식 1][Formula 1]
Figure PCTKR2013006868-appb-I000002
Figure PCTKR2013006868-appb-I000002
(상기 식 중, R1은 수소 또는 메틸기이고, R2는 탄소수 1 내지 10의 알킬기이고, X는 1 내지 10의 정수이며, n은 1 내지 2의 정수임).(Wherein R 1 is hydrogen or a methyl group, R 2 is an alkyl group having 1 to 10 carbon atoms, X is an integer of 1 to 10, and n is an integer of 1 to 2).
바람직하기로는 R2가 탄소수 1 내지 4의 알킬기이고, X는 1 내지 6의 정수인 것이 좋다.Preferably, R <2> is a C1-C4 alkyl group and X is an integer of 1-6.
상기 화학식 1의 화합물은 금속 표면과 화학적으로 반응하여 자연적으로 일종의 보호막(부식 방지 피막)을 형성함으로써 금속층의 부식을 효과적으로 억제할 수 있다. 상기 화합물은 금속 표면에 흡수되어 점착 계면에 안정한 보호막을 형성하여 물이 금속층의 표면에 작용하는 것을 방지하므로 부식을 억제할 수 있는 것이다.The compound of Formula 1 may effectively inhibit corrosion of the metal layer by chemically reacting with the metal surface to form a kind of protective film (corrosion preventing film). The compound is absorbed by the metal surface to form a stable protective film on the adhesive interface to prevent water from acting on the surface of the metal layer can suppress corrosion.
또한, 화학식 1에 함유된 -(O-R2)- 작용기의 반복에 의해 유기용매에 용해가 가능할 수 있다. In addition, it may be possible to dissolve in the organic solvent by the repetition of the-(OR 2 )-functional group contained in the formula (1).
또한, 일반적으로 상기 화학식 1의 화합물 등과 같은 인산이 함유된 화합물은 알코올 또는 물에 대한 용해도는 높으나 유기용매 중 특히 비극성 유기용매에는 용해도가 낮은 특성이 있다. In general, compounds containing phosphoric acid, such as the compound of Formula 1, have high solubility in alcohol or water, but have low solubility in organic solvents, particularly nonpolar organic solvents.
그러나, 본 발명과 같이 점착제 분야에 사용되는 경우에는 점착제의 용매로 아세톤 또는 메틸에틸케톤 등의 극성용매가 사용되므로 상기 화학식 1의 화합물의 용해성은 특별히 고려하지 않아도 된다.However, when used in the field of pressure-sensitive adhesive as in the present invention, since a polar solvent such as acetone or methyl ethyl ketone is used as the solvent of the pressure-sensitive adhesive, the solubility of the compound of Formula 1 does not need to be specifically considered.
이러한 화학식 1의 화합물은 합성되거나 시판되는 제품을 사용할 수있다. 시판품으로는 일례로 로디아(RHODIA)사 제품의 PAM 시리즈를 사용할 수 있다. 그 중에서 PAM100, PAM200이 극성유기용매와의 상용성이 우수하여 바람직하다.Such compounds of formula (1) may be used synthetic or commercially available products. As a commercial item, the PAM series by RHODIA company can be used as an example. Among them, PAM100 and PAM200 are preferred because of their excellent compatibility with polar organic solvents.
한편, 본 발명의 점착제 조성물은 상기 화학식 1의 화합물을 함유하여 공중합된 아크릴계 공중합체를 함유할 수 있다. 상기 화학식 1의 화합물은 아크릴계 공중합체를 형성하는 단량체의 성분으로 사용된다.On the other hand, the pressure-sensitive adhesive composition of the present invention may contain an acrylic copolymer copolymerized by containing the compound of formula (1). The compound of Formula 1 is used as a component of the monomer forming the acrylic copolymer.
본 발명의 아크릴계 공중합체는 탄소수 1-12의 알킬기를 갖는 (메타)아크릴레이트 단량체, 가교 가능한 관능기를 갖는 중합성 단량체 및 화학식 1의 화합물을 함유하는 것이 바람직하다. 여기서, (메타)아크릴레이트는 아크릴레이트 및 메타크릴레이트를 의미한다. It is preferable that the acryl-type copolymer of this invention contains the (meth) acrylate monomer which has a C1-C12 alkyl group, the polymerizable monomer which has a crosslinkable functional group, and the compound of General formula (1). Here, (meth) acrylate means acrylate and methacrylate.
상기 탄소수 1-12의 알킬기를 갖는 (메타)아크릴레이트 단량체로는 n-부틸(메타)아크릴레이트, 2-부틸(메타)아크릴레이트, t-부틸(메타)아크릴레이트, 2-에틸헥실(메타)아크릴레이트, 에틸(메타)아크릴레이트, 메틸(메타)아크릴레이트, n-프로필(메타)아크릴레이트, 이소프로필(메타)아크릴레이트, 펜틸(메타)아크릴레이트, n-옥틸(메타)아크릴레이트, 이소옥틸(메타)아크릴레이트, 노닐(메타)아크릴레이트, 데실(메타)아크릴레이트, 라우릴(메타)아크릴레이트 등을 들 수 있으며, 이들 중에서 n-부틸아크릴레이트, 2-에틸헥실아크릴레이트 또는 이들의 혼합물이 바람직하다. 이들은 단독 또는 2종 이상 혼합하여 사용할 수 있다.Examples of the (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms include n-butyl (meth) acrylate, 2-butyl (meth) acrylate, t-butyl (meth) acrylate, and 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 and 2-ethylhexyl acrylate Or mixtures thereof. These can be used individually or in mixture of 2 or more types.
상기 가교 가능한 관능기를 갖는 중합성 단량체는 화학 결합에 의해 점착제 조성물의 응집력 또는 점착 강도를 보강하여 내구성과 절단성을 부여하기 위한 역할을 한다. 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 있다.The polymerizable monomer having a crosslinkable functional group serves to provide durability and cutability by reinforcing the cohesive force or adhesive strength of the pressure-sensitive adhesive composition by chemical bonding. For example, the monomer which has a hydroxyl group, the monomer which has a carboxy group, the monomer which has an amide group, the monomer which has a tertiary amine group, etc. are mentioned, These can be used individually or in mixture of 2 or more types.
히드록시기를 갖는 단량체로는 2-히드록시에틸(메타)아크릴레이트, 2-히드록시프로필(메타)아크릴레이트, 2-드록시부틸(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, 및 10-히드록시데실비닐에테르 등을 들 수 있으며, 이들 중에서 4-히드록시부틸비닐에테르가 바람직하다.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.
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, 및 알킬기의 탄소수가 2-3인 2-히드록시알킬(메타)아크릴레이트의 카프로락톤 부가체에 무수 호박산을 개환 부가시킨 화합물 등을 들 수 있으며, 이들 중에서 (메타)아크릴산이 바람직하다. 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 to 3 carbon atoms of an alkyl group, 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, 및 2-히드록시에틸헥실(메타)아크릴아미드 등을 들 수 있으며, 이들중에서 (메타)아크릴아미드가 바람직하다. 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.
3차 아민기를 갖는 단량체로는 N,N-(디메틸아미노)에틸(메타)아크릴레이트, N,N-(디에틸아미노)에틸(메타)아크릴레이트, 및 N,N-(디메틸아미노)프로필(메타)아크릴레이트 등을 들 수 있다. 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) acrylate, etc. are mentioned.
이러한 가교 가능한 관능기를 갖는 중합성 단량체는 탄소수 1-12의 알킬기를 갖는 (메타)아크릴레이트 단량체 100중량부에 대하여 0.05 내지 10중량부로 포함되는 것이 바람직하고, 보다 바람직하게는 0.1 내지 8중량부인 것이 좋다. 함량이 0.05중량부 미만인 경우 점착제의 응집력이 작아지게 되어 내구성이 저하될 수 있으며, 10중량부 초과인 경우 높은 겔분율에 의해 점착력이 떨어지고 내구성에 문제를 야기할 수 있다.It is preferable that the polymerizable monomer which has such a crosslinkable functional group is contained in 0.05-10 weight part with respect to 100 weight part of (meth) acrylate monomers which have a C1-C12 alkyl group, More preferably, it is 0.1-8 weight part good. If the content is less than 0.05 parts by weight, the cohesive force of the pressure-sensitive adhesive may be reduced, the durability may be lowered. If the content is more than 10 parts by weight, the adhesive strength is lowered by a high gel fraction may cause problems in durability.
상기 화학식 1의 화합물은 탄소수 1-12의 알킬기를 갖는 (메타)아크릴레이트 단량체 100중량부에 대하여 1 내지 20중량부로 포함되는 것이 바람직하고, 보다 바람직하기로는 2 내지 10중량부인 것이 좋다. 함량이 1중량부 미만이면 부식 방지 효과가 미비할 수 있고 20중량부를 포함하는 경우에는 점착력이 너무 높아 재작업성을 저하시킬 수 있는 문제가 있다.The compound of Formula 1 is preferably contained in 1 to 20 parts by weight, more preferably 2 to 10 parts by weight based on 100 parts by weight of the (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms. If the content is less than 1 part by weight, the corrosion protection effect may be insignificant, and when it contains 20 parts by weight, there is a problem in that the adhesive force is too high to reduce reworkability.
아크릴계 공중합체는 상기 단량체들 이외에 다른 중합성 단량체를 점착력을 저하시키지 않는 범위, 예컨대 총량에 대하여 10중량부 이하로 더 함유할 수 있다.The acrylic copolymer may further contain other polymerizable monomers in addition to the above monomers in a range of not lowering the adhesive strength, for example, 10 parts by weight or less based on the total amount.
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 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.
아크릴계 공중합체는 겔투과크로마토그래피(Gel permeation chromatography, GPC)에 의해 측정된 중량평균분자량(폴리스티렌 환산, Mw)이 5만 내지 200만인 것이 바람직하며, 보다 바람직하기로는 40만 내지 200만인 것이 좋다. 중량평균분자량이 5만 미만인 경우 공중합체 간의 응집력이 부족하여 점착 내구성에 문제를 야기할 수 있고, 200만 초과인 경우 도공 시 공정성을 확보하기 위하여 다량의 희석 용매를 필요로 할 수 있다. 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.
본 발명의 점착제 조성물은 가교제를 추가로 함유할 수 있다.The pressure-sensitive adhesive composition of the present invention may further contain a crosslinking agent.
가교제는 밀착성 및 내구성을 향상시킬 수 있고, 고온에서의 신뢰성 및 점착제의 형상을 유지시킬 수 있다. A crosslinking agent can improve adhesiveness and durability, and can maintain the reliability and shape of an adhesive at high temperature.
상기 가교제는 이소시아네이트계, 에폭시계, 멜라민계, 과산화물계, 금속킬레이트계, 옥사졸린계 등이 사용될 수 있으며, 1종 또는 2종 이상을 혼합 사용할 수 있다. 이중 이소시아네이트계 또는 에폭시계가 바람직하다. The crosslinking agent may be an isocyanate type, an epoxy type, a melamine type, a peroxide type, a metal chelate type, an oxazoline type, or the like, and one or two or more kinds thereof may be used. Double isocyanate type or epoxy type is preferred.
상기 이소시아네이트계는 톨릴렌디이소시아네이트, 자일렌디이소시아네이트, 2,4-디페닐메탄디이소시아네이트, 4,4-디페닐메탄디이소시아네이트, 헥사메틸렌디이소시아네이트, 이소포론디이소시아네이트, 테트라메틸자일렌디이소시아네이트, 나프탈렌디이소시아네이트 등의 디이소시아네이트화합물; 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.The isocyanate type is tolylene diisocyanate, xylene diisocyanate, 2,4-diphenylmethane diisocyanate, 4,4-diphenylmethane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, tetramethyl xylene diisocyanate, naphthalenedi Diisocyanate compounds such as isocyanate; 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.
상기 에폭시계는 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.The epoxy-based ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, polypropylene glycol di Glycidyl ether, neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, polytetramethylene glycol diglycidyl ether, glycerol diglycidyl ether, glycerol triglycidyl ether, di Glycerol polyglycidyl ether, polyglycerol polyglycidyl ether, resorcin diglycidyl ether, 2,2-dibromoneopentyl glycol diglycidyl ether, trimethylolpropanetriglycidyl ether, pentaerythritol poly Glycidyl ether, sorbitol polyglycidyl ether, adipic acid diglycidyl ester, phthalic acid diglycidyl ester, tris (glycidyl) isocyanuric Tris (glycidoxyethyl) isocyanurate, 1,3-bis (N, N-glycidylaminomethyl) cyclohexane, N, N, N ', N'-tetraglycidyl-m- Xylylenediamine etc. are mentioned.
상기 멜라민계는 헥사메티롤멜라민, 헥사메톡시메틸멜라민, 헥사부톡시메틸멜라민 등을 들 수 있다.Examples of the melamine type include hexametholol melamine, hexamethoxymethyl melamine, hexabutoxymethyl melamine, and the like.
이러한 가교제는 상기 아크릴계 공중합체 100중량부에 대하여 0.1 내지 15중량부, 바람직하기로는 0.3 내지 5중량부 함유될 수 있다. 함유량이 0.1중량부 미만이면 부족한 가교도로 인해 응집력이 작게 되어 점착 내구성 및 절단성의 물성을 해칠 수 있으며, 15중량부를 초과할 경우에는 과다 가교반응에 의한 잔류응력 완화에 문제가 발생할 수 있다. Such a crosslinking agent may be contained in an amount of 0.1 to 15 parts by weight, preferably 0.3 to 5 parts by weight, based on 100 parts by weight of the acrylic copolymer. If the content is less than 0.1 part by weight, the cohesive force may be reduced due to insufficient crosslinking degree, thereby impairing the adhesive durability and the cleavage property. If the content is more than 15 parts by weight, problems may occur in reducing residual stress due to excessive crosslinking reaction.
또한, 본 발명의 점착제 조성물은 아크릴계 공중합체 및 상기 화학식 1의 화합물을 함유할 수 있다. 상기 화학식 1의 화합물은 점착제 조성물의 첨가제의 성분으로 사용된다. In addition, the pressure-sensitive adhesive composition of the present invention may contain an acrylic copolymer and the compound of Formula 1. The compound of Formula 1 is used as a component of an additive of the pressure-sensitive adhesive composition.
이때, 화학식 1의 화합물은 아크릴계 공중합체 100중량부에 대하여 1 내지 20중량부로 포함되는 것이 바람직하고, 보다 바람직하기로는 2 내지 15 중량부인 것이 좋다. 함량이 1중량부 미만이면 부식 방지 효과가 미비할 수 있고 20중량부를 초과하는 경우에는 점착력이 너무 높아 재작업성(리워크성)을 저하시킬 수 있는 문제가 있다.At this time, the compound of Formula 1 is preferably contained in 1 to 20 parts by weight, more preferably 2 to 15 parts by weight with respect to 100 parts by weight of the acrylic copolymer. If the content is less than 1 part by weight, the anti-corrosion effect may be insignificant, and if it exceeds 20 parts by weight, the adhesive force may be too high to reduce reworkability (reworkability).
또한, 본 발명의 점착제 조성물은 화학식 1의 화합물을 함유하여 공중합된 아크릴계 공중합체, 및 화학식 1의 화합물을 함유할 수 있다. 상기 화학식 1은 아크릴계 공중합체를 형성하는 성분과 동시에 점착제 조성물의 첨가제 성분으로 사용된다.In addition, the pressure-sensitive adhesive composition of the present invention may contain an acrylic copolymer copolymerized by containing a compound of Formula 1, and a compound of Formula 1. Formula 1 is used as an additive component of the pressure-sensitive adhesive composition at the same time as the component to form an acrylic copolymer.
이때, 상기 아크릴계 공중합체에 함유되는 화학식 1의 화합물은 탄소수 1-12의 알킬기를 갖는 (메타)아크릴레이트 단량체 100중량부에 대하여 1 내지 10중량부로 포함될 수 있다. 또한, 점착제 조성물의 첨가제로 사용되는 화학식 1의 화합물은 아크릴계 공중합체 100중량부에 대하여 1 내지 10중량부로 포함될 수 있다.In this case, the compound of Formula 1 contained in the acrylic copolymer may be included in an amount of 1 to 10 parts by weight based on 100 parts by weight of the (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms. In addition, the compound of Formula 1 used as an additive of the pressure-sensitive adhesive composition may be included in 1 to 10 parts by weight based on 100 parts by weight of the acrylic copolymer.
이외에 상기 점착제 조성물은 가교제를 추가로 함유할 수 있으며, 상기 아크릴계 공중합체와 가교제 각각 그 종류, 함량 및 물성 등은 상기에서 언급한 바와 동일하다.In addition, the pressure-sensitive adhesive composition may further contain a crosslinking agent, and the type, content and physical properties of the acrylic copolymer and the crosslinking agent are the same as mentioned above.
상기와 같은 성분 이외에, 점착제 조성물은 용도에 따라 요구되는 점착력, 응집력, 점성, 탄성률, 유리전이온도 등을 조절하기 위하여, 실란커플링제, 점착성 부여 수지, 산화방지제, 레벨링제, 표면윤활제, 염료, 안료, 소포제, 충전제, 광안정제, 대전방지제 등의 첨가제를 더 함유할 수 있다. In addition to the above components, the pressure-sensitive adhesive composition is a silane coupling agent, tackifying resin, antioxidant, leveling agent, surface lubricant, dye, in order to adjust the adhesion, cohesion, viscosity, elastic modulus, glass transition temperature, etc. Additives, such as a pigment, an antifoamer, a filler, a light stabilizer, an antistatic agent, can be further contained.
이중 실란커플링제는 점착제와 기재와의 밀착력을 향상시키는 역할함으므로 함유하는 것이 바람직하며, 아미노기, 에폭시기, 아세토아세틸기, 폴리알킬렌글리콜기, 아크릴기, 알킬기 등의 관능기를 함유하는 알콕시실란을 사용할 수 있다.Since the double silane coupling agent serves to improve the adhesion between the pressure-sensitive adhesive and the base material, it is preferable to contain it. Can be used.
이러한 첨가제는 본 발명의 효과를 저해하지 않는 범위내에서 적절히 함량을 조절할 수 있으며, 일례로 실란커플링제는 밀착력 및 내구성 등을 고려하여 아크릴계 공중합체 100중량부에 대하여 0.1 내지 2중량부 함유할 수 있다. Such additives may be appropriately adjusted in a range not impairing the effects of the present invention, for example, the silane coupling agent may contain 0.1 to 2 parts by weight based on 100 parts by weight of the acrylic copolymer in consideration of adhesion and durability. have.
본 발명의 점착제 조성물은 특히 액정셀과의 접합을 위한 편광판용 점착제, 표면보호필름용 점착제로 사용할 수 있다. 또한, 보호필름, 반사시트, 구조용 점착시트, 사진용 점착시트, 차선표시용 점착시트, 광학용 점착제품, 전자부품용 점착제뿐만 아니라 일반 상업용 점착시트제품으로도 사용 가능하다. In particular, the pressure-sensitive adhesive composition of the present invention can be used as a pressure-sensitive adhesive for polarizing plates and a surface protective film for bonding to liquid crystal cells. In addition, it can be used as a general commercial adhesive sheet product as well as a protective film, a reflective sheet, a structural adhesive sheet, a photographic adhesive sheet, a lane marking adhesive sheet, an optical adhesive product, an adhesive for electronic parts, and the like.
이하, 본 발명의 이해를 돕기 위하여 바람직한 실시예를 제시하나, 하기 실시예는 본 발명을 예시하는 것일 뿐 본 발명의 범주 및 기술사상 범위 내에서 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 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.
제조예 : 아크릴계 공중합체 제조 Preparation Example: Acrylic Copolymer Preparation
제조예 1 : 아크릴계 공중합체 APreparation Example 1 Acrylic Copolymer A
질소가스가 환류되고 온도조절이 용이하도록 냉각장치를 설치한 1 L의 반응기에 n-부틸아크릴레이트(BA) 85중량부, 메틸아크릴레이트(MA) 7중량부, 2-하이드록에틸아크릴레이트 2.0중량부, 아크릴산 1.0중량부, PAM200 제품(로디아사) 5.0중량부로 이루어진 단량체 혼합물을 투입한 후, 용제로 아세톤 100중량부를 투입하였다. 그 다음 산소를 제거하기 위하여 질소가스를 1시간 동안 퍼징한 후, 62 ℃로 유지하였다. 상기 혼합물을 균일하게 혼합한 후, 반응개시제로 아조비스이소부티로니트릴(AIBN) 0.07중량부를 투입하고, 6시간 동안 반응시켜 중량평균분자량이 약 100만인 아크릴계 공중합체 A를 제조하였다.85 parts by weight of n-butyl acrylate (BA), 7 parts by weight of methyl acrylate (MA), 2-hydroxyethyl acrylate 2.0 in a 1 L reactor equipped with a refrigeration system to facilitate nitrogen temperature reflux and temperature control. After the addition of the monomer mixture consisting of parts by weight, 1.0 part by weight of acrylic acid and 5.0 parts by weight of PAM200 product (Rhodia), 100 parts by weight of acetone was added as a solvent. Then, after purging nitrogen gas for 1 hour to remove oxygen, it was maintained 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 6 hours to prepare an acrylic copolymer A having a weight average molecular weight of about 1 million.
제조예 2 : 아크릴계 공중합체 BPreparation Example 2 Acrylic Copolymer B
상기 제조예 1과 동일하게 실시하되, n-부틸아크릴레이트(BA) 80중량부, 메틸아크릴레이트(MA) 7중량부, 2-하이드록에틸아크릴레이트 2.0중량부, 아크릴산 1.0중량부, PAM200 제품(로디아사) 10.0중량부로 이루어진 단량체 혼합물을 사용하여 중량평균분자량이 약 100만인 아크릴계 공중합체 B를 제조하였다.In the same manner as in Preparation Example 1, 80 parts by weight of n-butyl acrylate (BA), 7 parts by weight of methyl acrylate (MA), 2.0 parts by weight of 2-hydroxyethyl acrylate, 1.0 parts by weight of acrylic acid, PAM200 products (Rhodia Co., Ltd.) An acrylic copolymer B having a weight average molecular weight of about 1 million was prepared using a monomer mixture composed of 10.0 parts by weight.
제조예 3 : 아크릴계 공중합체 CPreparation Example 3 Acrylic Copolymer C
상기 제조예 1과 동일하게 실시하되, n-부틸아크릴레이트(BA) 75중량부, 메틸아크릴레이트(MA) 7중량부, 2-하이드록에틸아크릴레이트 2.0중량부, 아크릴산 1.0중량부, PAM200 제품(로디아사) 15.0중량부로 이루어진 단량체 혼합물을 사용하여 중량평균분자량이 약 100만인 아크릴계 공중합체 C를 제조하였다.In the same manner as in Preparation Example 1, 75 parts by weight of n-butyl acrylate (BA), 7 parts by weight of methyl acrylate (MA), 2.0 parts by weight of 2-hydroxyethyl acrylate, 1.0 parts by weight of acrylic acid, PAM200 products (Rhodia Co., Ltd.) An acrylic copolymer C having a weight average molecular weight of about 1 million was prepared using a monomer mixture composed of 15.0 parts by weight.
제조예 4: 아크릴계 공중합체 DPreparation Example 4 Acrylic Copolymer D
상기 제조예 1과 동일하게 실시하되, n-부틸아크릴레이트(BA) 65중량부, 메틸아크릴레이트(MA) 7중량부, 2-하이드록에틸아크릴레이트 2.0중량부, 아크릴산 1.0중량부, PAM200 제품(로디아사) 25.0중량부로 이루어진 단량체 혼합물을 사용하여 중량평균분자량이 약 100만인 아크릴계 공중합체 D를 제조하였다.In the same manner as in Preparation Example 1, 65 parts by weight of n-butyl acrylate (BA), 7 parts by weight of methyl acrylate (MA), 2.0 parts by weight of 2-hydroxyethyl acrylate, 1.0 parts by weight of acrylic acid, PAM200 products (Rhodia Co., Ltd.) An acrylic copolymer D having a weight average molecular weight of about 1 million was prepared using a monomer mixture composed of 25.0 parts by weight.
제조예 5: 아크릴계 공중합체 EPreparation Example 5 Acrylic Copolymer E
상기 제조예 1과 동일하게 실시하되, n-부틸아크릴레이트(BA) 55중량부, 메틸아크릴레이트(MA) 7중량부, 2-하이드록에틸아크릴레이트 2.0중량부, 아크릴산 1.0중량부, PAM200 제품(로디아사) 35.0중량부로 이루어진 단량체 혼합물을 사용하여 중량평균분자량이 약 100만인 아크릴계 공중합체 E를 제조하였다.In the same manner as in Preparation Example 1, 55 parts by weight of n-butyl acrylate (BA), 7 parts by weight of methyl acrylate (MA), 2.0 parts by weight of 2-hydroxyethyl acrylate, 1.0 parts by weight of acrylic acid, PAM200 products (Rhodia) An acrylic copolymer E having a weight average molecular weight of about 1 million was prepared using a monomer mixture composed of 35.0 parts by weight.
제조예 6 : 아크릴계 공중합체 F Preparation Example 6 Acrylic Copolymer F
상기 제조예 1과 동일하게 실시하되, PAM200 제품(로디아사) 대신에 PAM100 제품(로디아사)을 사용하여 중량평균분자량이 약 100만인 아크릴계 공중합체 F를 제조하였다.An acrylic copolymer F having a weight average molecular weight of about 1 million was prepared in the same manner as in Preparation Example 1, but using PAM100 (Rhodia) instead of PAM200 (Rhodia).
제조예 7 : 아크릴계 공중합체 GPreparation Example 7 Acrylic Copolymer G
상기 제조예 1과 동일하게 실시하되, n-부틸아크릴레이트(BA) 90중량부, 메틸아크릴레이트(MA) 7중량부, 2-하이드록에틸아크릴레이트 2.0중량부, 아크릴산 1.0중량부로 이루어진 단량체 혼합물을 사용하여 중량평균분자량이 약 100만인 아크릴계 공중합체 G를 제조하였다.A monomer mixture consisting of 90 parts by weight of n-butyl acrylate (BA), 7 parts by weight of methyl acrylate (MA), 2.0 parts by weight of 2-hydroxyethyl acrylate, and 1.0 parts by weight of acrylic acid was carried out in the same manner as in Preparation Example 1. Using to prepare an acrylic copolymer G having a weight average molecular weight of about 1 million.
실시예 및 비교예 : 점착제 조성물 제조Examples and Comparative Examples: Pressure-sensitive adhesive composition
실시예 1-14 및 비교예 1-2Example 1-14 and Comparative Example 1-2
하기 표 1과 같이, 각 성분을 혼합한 후 유기용매에 희석하여 점착제 조성물을 제조하였다.As shown in Table 1 below, the components were mixed and then diluted in an organic solvent to prepare a pressure-sensitive adhesive composition.
[표 1]TABLE 1
Figure PCTKR2013006868-appb-I000003
Figure PCTKR2013006868-appb-I000003
상기에서 제조된 점착제 조성물을 실리콘 이형제가 코팅된 이형필름 상에 두께가 25㎛가 되도록 도포하고 100℃에서 1분 동안 건조시켜 점착층을 형성하였다. The pressure-sensitive adhesive composition prepared above was applied on a release film coated with a silicone release agent to have a thickness of 25 μm, and dried at 100 ° C. for 1 minute to form an adhesive layer.
두께 185㎛의 요오드계 편광판에 상기 제조된 점착층을 점착 가공으로 적층하여 점착제 부착 편광판을 제조하였다. 제조된 편광판을 23℃, 60%RH의 조건 하에서 양생 기간 동안 보관하였다. A pressure-sensitive adhesive polarizing plate was prepared by laminating the pressure-sensitive adhesive layer prepared above on an iodine-based polarizing plate having a thickness of 185 μm. The prepared polarizing plate was stored under curing conditions at 23 ° C. and 60% RH.
시험예Test Example
상기 실시예 및 비교예에서 제조된 점착제 조성물, 점착제 부착 편광판의 물성을 하기의 방법으로 측정하고, 그 결과를 하기 표 2에 나타내었다. The physical properties of the pressure-sensitive adhesive composition and pressure-sensitive adhesive polarizing plate prepared in Examples and Comparative Examples were measured by the following method, and the results are shown in Table 2 below.
1. 금속층의 내부식성1. Corrosion resistance of metal layer
점착제 부착 편광판의 이형필름을 박리하고, 점착제층 표면과 알루미늄판을 접합한 후 60℃, 95%RH%의 분위기 하에서 250시간 방치하여 적층체 시편을 제조하였다.The release film of the polarizing plate with pressure-sensitive adhesive was peeled off, the surface of the pressure-sensitive adhesive layer and the aluminum plate were bonded together, and left to stand for 250 hours at 60 ° C. and 95% RH% to prepare a laminate specimen.
상기 적층체로부터 점착제층을 박리하고, 상기 점착제층과 접촉한 알루미늄판의 표면을 육안으로 관찰하여, 부식의 유무를 평가했다.The adhesive layer was peeled from the said laminated body, the surface of the aluminum plate which contacted the said adhesive layer was visually observed, and the presence or absence of corrosion was evaluated.
<평가기준><Evaluation Criteria>
알루미늄판 표면이 전혀 부식되지 않음: ○The surface of the aluminum plate is not corroded at all: ○
알루미늄판 표면이 부식됨: ×Surface of aluminum plate is corroded: ×
2. 금속층과의 점착력 (N/25mm) 2. Adhesive force with metal layer (N / 25mm)
점착제 부착 편광판의 이형필름을 박리하고 점착제층 표면과 알루미늄판을 접합한 후. 50℃, 5㎏/㎠(490.3 ㎪)로 20분간 오토크레이브 처리를 수행하였다. 이후에 23℃, 50RH%의 분위기 하에서 24시간 방치하여 적층체 시편을 제조하였다.After peeling the release film of the polarizing plate with an adhesive, and bonding the surface of an adhesive layer and an aluminum plate. Autoclave treatment was performed at 50 ° C. and 5 kg / cm 2 (490.3 kPa) for 20 minutes. Thereafter, the mixture was left for 24 hours in an atmosphere of 23 ° C. and 50 RH% to prepare a laminate specimen.
상기 적층체로부터 편광판을 300㎜/분의 속도 및 180°방향으로 박리하여 점착력을 측정하였다.The polarizing plate was peeled from the said laminated body at the speed | rate of 300 mm / min, and 180 degree direction, and the adhesive force was measured.
3. 금속층과의 점착 내구성3. Durability of adhesion with metal layer
점착제 부착 편광판의 이형필름을 박리하고 점착제층 표면과 알루미늄판을 접합한 후. 50℃, 5㎏/㎠(490.3 ㎪)로 20분간 오토크레이브 처리를 수행하였다. 이후에 23℃, 50RH%의 분위기 하에서 24시간 방치하여 적층체 시편을 제조하였다.After peeling the release film of the polarizing plate with an adhesive, and bonding the surface of an adhesive layer and an aluminum plate. Autoclave treatment was performed at 50 ° C. and 5 kg / cm 2 (490.3 kPa) for 20 minutes. Thereafter, the mixture was left for 24 hours in an atmosphere of 23 ° C. and 50 RH% to prepare a laminate specimen.
이후에 상기 적층체 시편을 온도 80℃의 건조조건 하에서 300시간 보관한 후 외관을 확인하였다(내열시험). Thereafter, the laminate specimen was stored for 300 hours under a drying condition at a temperature of 80 ° C., and then the appearance was confirmed (heat test).
<평가기준><Evaluation Criteria>
기포와 박리현상 3 개이상 시인됨: ×Bubble and exfoliation 3 or more acknowledged: ×
기포와 박리현상 시인되나 3개 미만 시인됨: △Bubble and exfoliation are admitted but less than 3 are admitted: △
기포와 박리현상 미시인됨: ○Bubbles and Peelings Unidentified: ○
4. 리워크성 4. Reworkability
편광판을 폭 25㎜, 길이 100㎜의 크기로 잘라내고, 이형필름을 박리한 후, 코닝사 #1737 유리에 0.25MPa의 압력으로 라미네이션하고 5기압, 50℃의 조건으로 20분 동안 오토클레이브를 처리하여 평가 샘플을 제조하였다. 내열조건인 80℃ 오븐에 넣은 후 10시간 뒤에 꺼내어 120시간 동안 상온에서 방치한 후 1.3㎝/s의 속도로 박리하였다. 또한, 내습조건인 60℃, 90RH% 오븐에 넣은 후 12시간 뒤에 꺼내어 120시간 동안 상온에서 방치한 후 1.3㎝/s의 속도로 박리하였다. The polarizing plate was cut out to a width of 25 mm and a length of 100 mm, 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. Evaluation samples were prepared. After putting it in an oven at 80 ° C., which was heat-resistant, it was taken out after 10 hours, left at room temperature for 120 hours, and then peeled at a speed of 1.3 cm / s. In addition, after being put into an oven at 60 ° C. and 90 RH% of humidity conditions, it was taken out after 12 hours, and left at room temperature for 120 hours, followed by peeling at a speed of 1.3 cm / s.
<평가기준><Evaluation Criteria>
-양쪽 조건 모두에서 유리 기판에 점착제의 남음이 없고 편광판의 찢어짐 없이 깨끗이 박리: ○-In both conditions, there is no adhesive left on the glass substrate and peeling off without tearing of the polarizing plate: ○
-어느 한쪽 조건 이상에서 패널에 점착제가 남아있거나 박리과정에서 편광판이 찢어는 현상은 없으나, 글라스 표면에 약간의 헤이즈가 관찰됨: △There is no adhesive left on the panel under more than one condition or the polarizer is torn during peeling, but some haze is observed on the glass surface:
-어느 한쪽 조건 이상에서 패널에 점착제가 남아있거나 박리과정에서 편광판이 찢어짐: ×The adhesive remains on the panel under more than one condition or the polarizer is torn during the peeling process: ×
[표 2]TABLE 2
Figure PCTKR2013006868-appb-I000004
Figure PCTKR2013006868-appb-I000004
상기 표 2와 같이, 본 발명에 따라 상기 화학식 1의 화합물을 함유하는 실시예 1 내지 14의 점착제 조성물은 비교예 1 내지 2에 비해 금속층의 내부식성, 점착력 및 점착 내구성(내열 조건)이 동시에 우수하다는 것을 확인할 수 있었다.As shown in Table 2, the pressure-sensitive adhesive composition of Examples 1 to 14 containing the compound of Formula 1 according to the present invention is superior in corrosion resistance, adhesive strength and adhesive durability (heat resistance conditions) of the metal layer at the same time compared to Comparative Examples 1 to 2 I could confirm that.
또한, 상기와 같은 점착력 및 점착 내구성 등의 물성 측정이 가능한 것으로 보아 화학식 1의 화합물이 유기용매에 용해되었음을 확인할 수 있었다.In addition, it was confirmed that the physical properties such as adhesion and adhesion durability as described above was confirmed that the compound of Formula 1 was dissolved in the organic solvent.

Claims (9)

  1. 하기 화학식 1의 화합물을 함유하는 점착제 조성물:Pressure-sensitive adhesive composition containing a compound of formula
    [화학식 1][Formula 1]
    Figure PCTKR2013006868-appb-I000005
    Figure PCTKR2013006868-appb-I000005
    (상기 식 중, R1은 수소 또는 메틸기이고, R2는 탄소수 1 내지 10의 알킬기이고, X는 1 내지 10의 정수이며, n은 1 내지 2의 정수임).(Wherein R 1 is hydrogen or a methyl group, R 2 is an alkyl group having 1 to 10 carbon atoms, X is an integer of 1 to 10, and n is an integer of 1 to 2).
  2. 청구항 1에 있어서, 상기 화학식 1은 R2가 탄소수 1 내지 4의 알킬기이고 X는 1 내지 6의 정수인 것인 점착제 조성물.The pressure-sensitive adhesive composition of claim 1, wherein in Formula 1, R 2 is an alkyl group having 1 to 4 carbon atoms and X is an integer of 1 to 6.
  3. 청구항 1에 있어서, 상기 점착제 조성물은 아크릴계 공중합체 및 화학식 1의 화합물을 함유하는 것인 점착제 조성물.The pressure-sensitive adhesive composition of claim 1, wherein the pressure-sensitive adhesive composition contains an acrylic copolymer and a compound of Formula 1.
  4. 청구항 3에 있어서, 상기 아크릴계 공중합체 100중량부에 대하여 및 화학식 1의 화합물 1 내지 20중량부를 함유하는 것인 점착제 조성물.The pressure-sensitive adhesive composition of claim 3, which contains 1 to 20 parts by weight of the compound of Formula 1 and 100 parts by weight of the acrylic copolymer.
  5. 청구항 1에 있어서, 상기 점착제 조성물은 화학식 1의 화합물을 함유하여 공중합된 아크릴계 공중합체를 함유하는 것인 점착제 조성물.The pressure-sensitive adhesive composition of claim 1, wherein the pressure-sensitive adhesive composition contains an acrylic copolymer copolymerized with a compound of Formula 1.
  6. 청구항 5에 있어서, 상기 아크릴계 공중합체는 탄소수 1-12의 알킬기를 갖는 (메타)아크릴레이트 단량체, 가교 가능한 관능기를 갖는 중합성 단량체, 및 화학식 1의 화합물을 함유하는 것인 점착제 조성물.The pressure-sensitive adhesive composition of claim 5, wherein the acrylic copolymer contains a (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms, a polymerizable monomer having a crosslinkable functional group, and a compound of Formula 1.
  7. 청구항 6에 있어서, 상기 화학식 1의 화합물은 탄소수 1-12의 알킬기를 갖는 (메타)아크릴레이트 단량체 100중량부에 대하여 1 내지 20중량부를 함유하는 점착제 조성물.The pressure-sensitive adhesive composition of claim 6, wherein the compound of Formula 1 contains 1 to 20 parts by weight based on 100 parts by weight of the (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms.
  8. 청구항 6에 있어서, 상기 아크릴계 공중합체는 중량평균분자량(폴리스티렌 환산, Mw)이 5만 내지 200만인 것인 점착제 조성물.The pressure-sensitive adhesive composition of claim 6, wherein the acrylic copolymer has a weight average molecular weight (polystyrene equivalent, Mw) of 50,000 to 2 million.
  9. 청구항 1에 있어서, 상기 점착제 조성물은 화학식 1의 화합물을 함유하여 공중합된 아크릴계 공중합체, 및 화학식 1의 화합물을 함유하는 것인 점착제 조성물.The pressure-sensitive adhesive composition of claim 1, wherein the pressure-sensitive adhesive composition contains an acrylic copolymer copolymerized with a compound of Formula 1, and a compound of Formula 1.
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