WO2015020322A1 - Composition adhésive et plaque polarisante composite utilisant celle-ci - Google Patents

Composition adhésive et plaque polarisante composite utilisant celle-ci Download PDF

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Publication number
WO2015020322A1
WO2015020322A1 PCT/KR2014/006577 KR2014006577W WO2015020322A1 WO 2015020322 A1 WO2015020322 A1 WO 2015020322A1 KR 2014006577 W KR2014006577 W KR 2014006577W WO 2015020322 A1 WO2015020322 A1 WO 2015020322A1
Authority
WO
WIPO (PCT)
Prior art keywords
meth
acrylate
diisocyanate
polarizing plate
adhesive composition
Prior art date
Application number
PCT/KR2014/006577
Other languages
English (en)
Korean (ko)
Inventor
최한영
문제욱
이도규
Original Assignee
동우화인켐 주식회사
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 동우화인켐 주식회사 filed Critical 동우화인켐 주식회사
Publication of WO2015020322A1 publication Critical patent/WO2015020322A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • 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
    • C09J133/04—Homopolymers or copolymers of esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
    • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
    • C08G18/7621—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
    • C08G18/7628—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group
    • C08G18/7642—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group containing at least two isocyanate or isothiocyanate groups linked to the aromatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate groups, e.g. xylylene diisocyanate or homologues substituted on the aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
    • C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
    • C08G18/8009—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203
    • C08G18/8022—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203 with polyols having at least three hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C09J175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state

Definitions

  • the patterned retardation film is usually bonded to one side of the polarizing plate through an adhesive or a pressure-sensitive adhesive, and in recent years also bonded to one side of the polyvinyl alcohol polarizer for thinner film weight.
  • Korean Unexamined Patent Publication No. 2013-0028881 discloses a method for producing a film patterned retarder, and a film patterned retarder, and a polarizing plate and an image display device having the same.
  • Patent Document 1 Korean Patent Publication No. 2013-0028881
  • the isocyanate crosslinking agent is an isocyanurate body self-condensed at least one of 3 moles of xylene diisocyanate, hexamethylene diisocyanate and isophorone diisocyanate, and the isocyanate crosslinking agent is xylene diisocyanate
  • the adhesive composition which is at least 1 sort (s) chosen from the group which consists of an adduct of 3 mol of at least 1 sort (s) of hexamethylene diisocyanate and isophorone diisocyanate, and a trimethylol propane body.
  • crosslinkable functional group is a hydroxyl group, carboxyl group, amide group or tertiary amine group
  • pressure-sensitive adhesive composition is a hydroxyl group, carboxyl group, amide group or tertiary amine group
  • the patterned retardation layer comprises a liquid crystal coating layer containing a reactive liquid crystal monomer including an ester bond.
  • the peel force between the polarizer and the patterned retardation layer is 3 N / 25mm or more, composite polarizing plate.
  • the patterned retardation layer does not include an alignment film, a composite polarizing plate.
  • Image display device including the composite polarizer of the above seven.
  • the composite polarizing plate bonded with the pressure-sensitive adhesive composition of the present invention is excellent in heat resistance and heat-and-moisture resistance, and even when exposed to high temperature and high humidity conditions for a long time, peeling and rolling phenomenon are suppressed.
  • the acrylic copolymer according to the present invention is polymerized to include a (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms and a monomer having a crosslinkable functional group.
  • (meth) acrylate refers to acrylate, methacrylate or both at the same time.
  • (meth) acrylate monomer having an alkyl group having 1 to 12 carbon atoms examples include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, and isopropyl (meth) acrylate.
  • 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 isocyanate is included in an excessive amount as in the above content range, in which case the unreacted isocyanate group is contacted with moisture to be converted into an amino group (-NH 2 ).
  • the amino group forms a hydrogen bond with the polar group included in the polarizer surface polar group and the liquid crystal coating layer of the patterned retardation layer, and includes a reactive liquid crystal monomer contained on the liquid crystal coating layer.
  • the bonding strength of the polarizer and the patterned retardation layer is significantly improved by the hydrogen bond and the covalent bond.
  • the present invention provides a composite polarizing plate prepared using the pressure-sensitive adhesive composition.
  • the composite polarizing plate of the present invention can be used at a position where a conventional polarizing plate and a patterned retardation layer are stacked.
  • a crosslinking agent was added as shown in Table 2 to prepare a pressure-sensitive adhesive composition.
  • L C Center luminance of left eye image
  • L e Average luminance of peripheral part of left eye image

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Nonlinear Science (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Polarising Elements (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

La présente invention concerne une composition adhésive et une plaque polarisante composite utilisant celle-ci, plus particulièrement une composition adhésive et une plaque polarisante composite utilisant celle-ci dans laquelle la composition adhésive comprend : un copolymère polymérisé contenant des monomères de (méth)acrylate ayant un groupe alkyle composé de 1 à 12 atomes de carbone, et des monomères comprenant un groupe fonctionnel réticulable ; et de 200 à 2 000 % en poids d'un agent de réticulation isocyanate rapportés aux 100 % en poids de monomères réticulables, améliorant ainsi sensiblement l'adhésivité entre un polariseur et une couche de retardement à motifs lorsqu'elle est utilisée pour produire une plaque polarisante composite en amenant le polariseur et la couche de retardement à motifs à adhérer ensemble, et contribuant à améliorer la résistance à la chaleur et la résistance à la chaleur humide, ainsi qu'à donner un superbe effet tridimensionnel.
PCT/KR2014/006577 2013-08-08 2014-07-21 Composition adhésive et plaque polarisante composite utilisant celle-ci WO2015020322A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020130093993A KR20150017859A (ko) 2013-08-08 2013-08-08 점착제 조성물 및 이를 이용한 복합 편광판
KR10-2013-0093993 2013-08-08

Publications (1)

Publication Number Publication Date
WO2015020322A1 true WO2015020322A1 (fr) 2015-02-12

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Application Number Title Priority Date Filing Date
PCT/KR2014/006577 WO2015020322A1 (fr) 2013-08-08 2014-07-21 Composition adhésive et plaque polarisante composite utilisant celle-ci

Country Status (3)

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KR (1) KR20150017859A (fr)
TW (1) TW201506109A (fr)
WO (1) WO2015020322A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111171766A (zh) * 2020-03-17 2020-05-19 苏州世华新材料科技股份有限公司 一种超低吸水丙烯酸酯压敏胶及其制备方法
CN113056531A (zh) * 2018-11-20 2021-06-29 乐金华奥斯有限公司 自修复性涂敷组合物及利用其的片

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20060018883A (ko) * 2003-06-30 2006-03-02 소켄 케미칼 앤드 엔지니어링 캄파니, 리미티드 표면 보호 필름용 점착제 및 표면 보호 필름
KR20120120076A (ko) * 2011-04-22 2012-11-01 후지모리 고교 가부시키가이샤 점착제 조성물 및 표면보호필름
KR20120120078A (ko) * 2011-04-22 2012-11-01 후지모리 고교 가부시키가이샤 점착제 조성물 및 표면보호필름
KR20130056169A (ko) * 2011-11-21 2013-05-29 후지모리 고교 가부시키가이샤 점착제 조성물 및 표면 보호 필름

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20060018883A (ko) * 2003-06-30 2006-03-02 소켄 케미칼 앤드 엔지니어링 캄파니, 리미티드 표면 보호 필름용 점착제 및 표면 보호 필름
KR20120120076A (ko) * 2011-04-22 2012-11-01 후지모리 고교 가부시키가이샤 점착제 조성물 및 표면보호필름
KR20120120078A (ko) * 2011-04-22 2012-11-01 후지모리 고교 가부시키가이샤 점착제 조성물 및 표면보호필름
KR20130056169A (ko) * 2011-11-21 2013-05-29 후지모리 고교 가부시키가이샤 점착제 조성물 및 표면 보호 필름

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113056531A (zh) * 2018-11-20 2021-06-29 乐金华奥斯有限公司 自修复性涂敷组合物及利用其的片
CN113056531B (zh) * 2018-11-20 2022-05-31 乐金华奥斯有限公司 自修复性涂敷组合物及利用其的片
CN111171766A (zh) * 2020-03-17 2020-05-19 苏州世华新材料科技股份有限公司 一种超低吸水丙烯酸酯压敏胶及其制备方法

Also Published As

Publication number Publication date
KR20150017859A (ko) 2015-02-23
TW201506109A (zh) 2015-02-16

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