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WO2015060567A1 - Composition adhésive et plaque polarisante composite l'utilisant - Google Patents

Composition adhésive et plaque polarisante composite l'utilisant Download PDF

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Publication number
WO2015060567A1
WO2015060567A1 PCT/KR2014/009520 KR2014009520W WO2015060567A1 WO 2015060567 A1 WO2015060567 A1 WO 2015060567A1 KR 2014009520 W KR2014009520 W KR 2014009520W WO 2015060567 A1 WO2015060567 A1 WO 2015060567A1
Authority
WO
WIPO (PCT)
Prior art keywords
adhesive composition
monomer
polarizing plate
group
polarizer
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/KR2014/009520
Other languages
English (en)
Korean (ko)
Inventor
최한영
이도규
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dongwoo Fine Chem Co Ltd
Original Assignee
Dongwoo Fine Chem Co Ltd
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 Dongwoo Fine Chem Co Ltd filed Critical Dongwoo Fine Chem Co Ltd
Priority to CN201480044077.7A priority Critical patent/CN105473677B/zh
Publication of WO2015060567A1 publication Critical patent/WO2015060567A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • 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
    • C09J125/00—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 an aromatic carbocyclic ring; Adhesives based on derivatives of such polymers
    • C09J125/18—Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen
    • 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
    • C09J125/00—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 an aromatic carbocyclic ring; Adhesives based on derivatives of such polymers
    • C09J125/02—Homopolymers or copolymers of hydrocarbons
    • C09J125/04—Homopolymers or copolymers of styrene

Definitions

  • the present invention relates to an adhesive composition and a composite polarizing plate using the same.
  • Displays such as liquid crystal displays for stereoscopic image implementation often include a patterned retardation film.
  • the patterned retardation film configures the optical axis of each pattern region in different directions to implement a stereoscopic image by different images transmitted to the left and right eyes of a viewer wearing polarized glasses.
  • the patterned retardation film can typically be formed by forming an alignment film on a glass substrate and coating and aligning the liquid crystal on the alignment film.
  • the photoreactive liquid crystal material is oriented on the alignment film and then crosslinked by light irradiation such as ultraviolet light to form a polymer liquid crystal film.
  • the retarder pattern functions according to the alignment direction of the liquid crystal corresponding to the surface alignment of the alignment film.
  • 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.
  • the conventional polyvinyl alcohol polarizer may shrink in the stretching direction. Accordingly, the phase difference may be different for each position of the phase difference layer, thereby reducing the 3D stereoscopic feeling.
  • 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
  • An object of the present invention is to provide an adhesive composition capable of significantly improving the bonding force between a polarizer and a patterned retardation layer when used to bond a polarizer and a patterned retardation layer to produce a composite polarizing plate.
  • An object of the present invention is to provide a composite polarizing plate bonded through the adhesive composition.
  • An adhesive composition comprising a binder resin and a crosslinking agent polymerized including a styrene-based monomer having a hydroxy group.
  • R 1 is a hydrogen atom or a methyl group
  • R 2 is a direct bond, a linear or branched alkylene group having 1 to 6 carbon atoms, -CO- or -SO 2- ,
  • the alkylene group may be interrupted by an oxygen atom).
  • the adhesive composition In the above 1, wherein the styrene-based monomer having a hydroxy group is polymerized, including at least 50% by weight of the total weight of the total monomer, the adhesive composition.
  • binder resin is polymerized further including an ionic monomer, adhesive composition.
  • the ionic monomer is at least one selected from the group consisting of acrylic ammonium salt, styrene ammonium salt and vinyl imidazonium salt, adhesive composition.
  • the adhesive composition wherein the ionic monomer is polymerized to include 7 to 30% by weight of the total weight of the monomer, the adhesive composition.
  • the binder resin is polymerized by further comprising at least one of an acrylic monomer having a hydroxy group and an acrylic monomer having a carboxyl group, the adhesive composition.
  • the acrylic monomer having a hydroxy group and the acrylic monomer having a carboxyl group is polymerized by including a total content of 7 to 30% by weight of the total weight of the total monomer.
  • the cross-linking agent is monoaldehyde, dialdehyde, amino-formaldehyde resin, glyoxalate, acetal compound, divalent metal, divalent metal salt, trivalent metal, tetravalent metal, metal chelate compound
  • Adhesive composition which is at least one selected from the group consisting of logistics, oxazolines, melamines, aziridines and polyorganic acids.
  • Composite polarizing plate comprising a patterned retardation layer bonded to one surface of the polarizer through the adhesive composition of any one of 1 to 9 above.
  • the polarizer is a composite polarizing plate is a film having a function of a protective film or a retardation film is bonded on the opposite side of the surface is bonded with the patterned retardation layer.
  • the composite polarizing plate of 10 above, wherein the patterned retardation layer comprises a liquid crystal coating layer containing a reactive liquid crystal monomer including a benzene ring.
  • the patterned retardation layer does not include an alignment film, a composite polarizing plate.
  • the peeling force between the polarizer and the patterned retardation layer is 1.0 N / 25mm or more, composite polarizing plate.
  • Image display device including the composite polarizing plate of 10 above.
  • the pressure-sensitive adhesive composition of the present invention significantly improves the bonding force between the polarizer and the patterned retardation layer when used to bond the polarizer and the patterned retardation layer to produce a composite polarizing plate.
  • 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 composite polarizing plate bonded with the pressure-sensitive adhesive composition of the present invention simultaneously has a polarizing function and an improved 3D stereoscopic effect.
  • the present invention includes a binder resin and a crosslinking agent polymerized by including a styrene-based monomer having a hydroxy group, and when used to bond a polarizer and a patterned retardation layer to produce a composite polarizing plate,
  • the present invention relates to an adhesive composition that significantly improves bonding strength, improves heat resistance and heat and moisture resistance, as well as has an excellent 3D steric effect.
  • the adhesive composition of this invention contains a binder resin as an aqueous adhesive composition.
  • the binder resin according to the present invention is polymerized including a styrene monomer having a hydroxyl group.
  • the adhesive composition of the present invention has excellent bonding strength when used to bond the polarizer and the patterned retardation layer, and heat and moisture resistance are also improved by such bonding strength improvement.
  • This is a styrene-based monomer according to the invention comprises a hydroxyl group, the hydroxy group is a hydrogen bond with the polar group contained in the liquid crystal coating layer of the polarizer surface polar group and the patterned retardation layer, the benzene ring of the styrene monomer is a patterned phase difference It is judged by the pi bond interaction with the benzene ring contained in the liquid crystal coating layer of the layer.
  • the styrene monomer having a hydroxy group according to the present invention is not particularly limited, and examples thereof include monomers represented by the following general formula (1):
  • R 1 is a hydrogen atom or a methyl group
  • R 2 is a direct bond, a linear or branched alkylene group having 1 to 6 carbon atoms, -CO- or -SO 2- ,
  • the alkylene group may be interrupted by an oxygen atom).
  • the styrene-based monomer having a hydroxy group include the following formulas a-1 to a-5, which may be used alone or in combination of two or more.
  • the monomer of Formula (a-4) has a carboxy group but has -OH and R 2 in Formula 1 is -CO-
  • the monomer of Formula (a-5) has a sulfonic acid group but has -OH group
  • R 2 is -SO 2-
  • the content of the styrene-based monomer having a hydroxyl group is not particularly limited within the range capable of performing the above function, for example, 50% by weight or more of the total weight of the entire monomer may be included and polymerized. When the content is within the above range, it is possible to maximize the bonding force between the polarizer and the patterned retardation layer. In such aspect, it may preferably be included in 50 to 85% by weight of the total weight of the monomers.
  • the binder resin according to the present invention may further polymerize by including an ionic monomer.
  • the solubility in a solvent can be remarkably improved, the bonding strength can be improved, and the occurrence of the poor viscosity due to the remaining foreign matter can be suppressed.
  • the ionic monomer according to the present invention is not particularly limited as long as it can perform the above functions, and examples thereof include acrylic ammonium salts, styrene ammonium salts, and vinylimidazonium salts. Specifically, the monomer represented by following Chemical formulas 2-6 is mentioned. These can be used individually or in mixture of 2 or more types.
  • the content of the ionic monomer is not particularly limited within the range capable of performing the above function, for example, it may be included in the content of 7 to 30% by weight of the total weight of the monomers and polymerized.
  • the content of the ionic monomer is less than 7% by weight solubility improvement effect may be insignificant, and when the content of more than 30% by weight may be reduced heat and moisture resistance and adhesion.
  • the molecular weight of the binder resin is not particularly limited, and for example, the weight average molecular weight may be 5,000 to 100,000.
  • the binder resin may be prepared by a conventional polymerization method, and the weight average molecular weight may be adjusted by changing conditions such as the content of the initiator, the reaction temperature, the reaction time, the type and content of the catalyst, and the use of other components.
  • the kind of the solvent and the polymerization initiator is not particularly limited, and those known in the art may be used.
  • the binder resin according to the present invention may be polymerized further including at least one of an acrylic monomer having a hydroxy group and an acrylic monomer having a carboxyl group.
  • an acrylic monomer having a hydroxyl group or a carboxyl group By further including and polymerizing an acrylic monomer having a hydroxyl group or a carboxyl group, the wettability of the resin may be improved and the bonding force may be further improved.
  • the acrylic monomer having a hydroxy group according to the present invention may be represented by the following formula (7):
  • R 1 is hydrogen or methyl
  • X is oxygen or —NH—
  • R 2 is a straight or branched chain alkylene group having 1 to 6 carbon atoms and is interrupted by a cycloalkylene group having 3 to 6 carbon atoms Can be).
  • acrylic monomer having a hydroxy group according to the present invention include the following formula b-1 to formula b-6, which may be used alone or mixed two or more kinds.
  • acrylic monomer having a carboxyl group according to the present invention include the following formulas c-1 to c-9, which may be used alone or in combination of two or more.
  • the acrylic monomer having a hydroxy group and the acrylic monomer having a carboxyl group may be polymerized by including a total content of 7 to 30% by weight of the total weight of the entire monomer.
  • the total content is less than 7% by weight, the effect of improving the bonding strength due to the improvement of the wettability may be insignificant, and when the total content is more than 30% by weight, the interaction with the patterned retardation layer may be lowered, thereby lowering the bonding strength.
  • the adhesive composition of the present invention further includes a crosslinking agent.
  • the crosslinking agent is not particularly limited and may be a crosslinking agent commonly used in the art.
  • monoaldehydes such as formaldehyde, acetaldehyde, propionaldehyde, butylaldehyde, etc .
  • Glyoxal malondialdehyde, succinic aldehyde, glutaraldehyde, malealdehyde dialdehyde, phthalaldehyde, etc .
  • Amino-formaldehyde resins such as methylolurea, methylolmelamine, alkylated methylolurea, alkylated methylolated melamine, acetoguanamine, benzoguanamine and formaldehyde condensate
  • glyoxylic acid metal salts examples include alkali metals such as lithium, sodium and potassium, alkaline earth metals such as magnesium and calcium, transition metals such as titanium, zirconium, chromium, manga
  • Glyoxylates such as glyoxylic acid amine salts (such as ammonia, monomethylamine, dimethylamine, trimethylamine, etc.); Divalent metal or a salt of magnesium, calcium, aluminum, iron, nickel, zinc, and the like; methoxy bullet, diethoxy bullet, bullet-dialkoxy acetal such as the compound of the; Trivalent metals; Tetravalent metals; Metal chelate compounds; Oxazolines; Melamines; Aziridines; Polyvalent inorganic acids, such as boric acid, phosphoric acid, and sulfuric acid, etc. are mentioned. These can be used individually or in mixture of 2 or more types.
  • the content of the crosslinking agent is not particularly limited, and may be included, for example, in an amount of 0.5 to 20 parts by weight based on 100 parts by weight of the binder resin.
  • the content of the crosslinking agent is within the above range, the effect of improving the bonding strength between the polarizer and the patterned retardation layer is excellent.
  • the present invention provides a composite polarizing plate manufactured using the adhesive composition.
  • the composite polarizing plate of the present invention includes a polarizer and a patterned retardation layer bonded to one surface of the polarizer through the adhesive composition.
  • the polarizer and the patterned retardation layer are bonded through the adhesive composition, and the bonding strength is excellent.
  • the adhesive composition layer forms a hydrogen bond with the polarizer, a hydrogen bond with the patterned retardation layer, and a pi bond interaction may occur.
  • the polarizer is generally used in the display field, and the polarizer is not limited as long as it can polarize incident light.
  • a film made of polyvinyl alcohol (PVA) may be used by dyeing iodine or dichroic dye and drawing it in a predetermined direction.
  • PVA polyvinyl alcohol
  • On the opposite side of the surface to be bonded to the patterned retardation layer may be a film having a function of a protective film or retardation film is bonded.
  • the configuration of the patterned retardation layer is not particularly limited and may include a configuration generally used in the art.
  • it may have a structure laminated in the order of the substrate, the alignment film and the liquid crystal coating layer, or may be a structure that does not include the alignment film.
  • the patterned retardation layer is bonded so that the liquid crystal coating layer faces the polarizer.
  • the base material is not particularly limited as long as it is formed of a material having excellent transparency, mechanical strength, thermal stability, moisture shielding property, retardation uniformity, and isotropy.
  • the polyolefin resin, polyester resin, cellulose resin, and polycarbonate resin Acrylic resin, styrene resin, vinyl chloride resin, amide resin, imide resin, polyether sulfone resin, sulfone resin, polyether sulfone resin, polyether ether ketone resin, sulfonated polyphenylene resin,
  • a substrate formed of at least one material selected from the group consisting of vinyl alcohol resin, vinylidene chloride resin, vinyl butyral resin, allylate resin, polyoxymethylene resin and epoxy resin can be used.
  • the alignment layer is formed by coating a composition for forming an alignment layer commonly used in the art on the substrate and imparting orientation, and then patterning the substrate to have different orientation directions. Can be.
  • the orientation providing method may include a rubbing method, a photo alignment method, and the like, and the patterning method may be based on a plurality of exposure processes using a photomask, but is not limited thereto.
  • the light used for the exposure is not particularly limited, but for example, polarized ultraviolet irradiation, ion beam or plasma beam irradiation, radiation irradiation, or the like can be used.
  • polarized ultraviolet irradiation ion beam or plasma beam irradiation, radiation irradiation, or the like can be used.
  • the liquid crystal coating layer may be formed by applying a composition for forming a liquid crystal coating layer, including a reactive liquid crystal monomer (RM), which is commonly used in the art, on an alignment layer and crosslinking the same.
  • a composition for forming a liquid crystal coating layer including a reactive liquid crystal monomer (RM), which is commonly used in the art, on an alignment layer and crosslinking the same.
  • RM reactive liquid crystal monomer
  • the reactive liquid crystal monomer is not particularly limited and may be a monomer commonly used in the art, but may preferably be a monomer having a benzene ring.
  • the composition for forming a liquid crystal coating layer may be applied onto the substrate without the alignment layer, and may be exposed to simultaneously perform patterning and orientation to form a patterned retardation layer.
  • composition for forming a liquid crystal coating layer may further include a compound which can be aligned by polarized ultraviolet light such as a linear photopolymerizable polymer for alignment.
  • the patterned retardation layer does not include an alignment layer, a thinner display can be realized.
  • the composite polarizing plate of the present invention prepared using the adhesive composition has excellent bonding strength between the polarizer and the patterned retardation layer.
  • the peeling force between the polarizer and the patterned retardation layer may be 1.0 N / 25 mm or more, preferably 1.0 to 3.0 N / 25 mm It can be longer.
  • the present invention provides an image display device including the composite polarizing plate.
  • the image display device is not particularly limited, and examples thereof include stereoscopic image implementation or semi-transmissive liquid crystal display device, plasma display device, organic EL display device, and the like.
  • 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.
  • an adhesive composition having the composition and content of Table 1.
  • a weight average molecular weight was prepared to be 10,000 g / mol.
  • MPR32, DNP patterned retardation layer
  • DNP triacetyl cellulose protective film
  • the mixture was dried at 100 ° C. for 3 minutes and allowed to stand at room temperature for 48 hours to cure.
  • Peel force was measured by cutting the prepared composite polarizing plate sample in a width of 25mm, peeling at a rate of 300mm / min in the 180 degree peeling direction.
  • a composite polarizing plate was prepared in the same manner as in Experimental Example (1), an acrylic pressure-sensitive adhesive was applied to the protective film and cured, and then bonded to soda glass and subjected to autoclave treatment.
  • the heat resistance test was performed at 80 ° C. for 500 hours and the humidity and heat resistance test at 60 ° C. and 90% RH for 500 hours, and then confirmed the occurrence of bubbles or peeling at the bonding surface of the liquid crystal coating layer and the polarizer. The heat and humidity resistance was evaluated.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Polarising Elements (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

La présente invention concerne une composition adhésive, et plus spécifiquement, une composition adhésive comprenant: une résine liante polymérisée contenant un monomère à base de styrène présentant un groupe hydroxy; et un agent de réticulation, améliorant ainsi notablement l'adhésivité entre un polarisant et une couche de déphasage à motifs lorsqu'elle est utilisée pour produire une plaque polarisante composite par adhésion du polarisant à la couche de déphasage à motifs, et contribuant à améliorer la résistance à la chaleur et la résistance à à la chaleur humide, ainsi que conférant un superbe effet tridimensionnel.
PCT/KR2014/009520 2013-10-23 2014-10-10 Composition adhésive et plaque polarisante composite l'utilisant Ceased WO2015060567A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201480044077.7A CN105473677B (zh) 2013-10-23 2014-10-10 粘合剂组合物和使用其的复合偏光板

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2013-0126474 2013-10-23
KR1020130126474A KR101918623B1 (ko) 2013-10-23 2013-10-23 접착제 조성물 및 이를 이용한 복합 편광판

Publications (1)

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WO2015060567A1 true WO2015060567A1 (fr) 2015-04-30

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KR (1) KR101918623B1 (fr)
CN (1) CN105473677B (fr)
TW (1) TW201516107A (fr)
WO (1) WO2015060567A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3469032A1 (fr) * 2016-06-13 2019-04-17 Acatechol, Inc. Polymères ioniques et leur utilisation comme adhésifs et revêtements humides
CN119735732B (zh) * 2025-03-04 2025-06-24 浙江工业大学 一种罗丹明聚合物超分辨纳米探针的合成方法

Citations (6)

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Publication number Priority date Publication date Assignee Title
US4880487A (en) * 1988-06-24 1989-11-14 Hoechst Celanese Corporation Hot melt adhesives containing poly(p-hydroxystyrene) homopolymers and copolymers and bonding methods employing same
KR20070021128A (ko) * 2004-01-16 2007-02-22 테사 악티엔게젤샤프트 배향된 아크릴레이트 접착 물질, 이의 제조 방법 및 용도
KR20080100852A (ko) * 2006-04-14 2008-11-19 오츠카 가가쿠 가부시키가이샤 수지 조성물 및 내열성 점착제
KR20100131423A (ko) * 2008-01-31 2010-12-15 닛토덴코 가부시키가이샤 편광자 보호 필름, 편광판 및 화상 표시 장치
JP2011032412A (ja) * 2009-08-04 2011-02-17 Tokyo Ohka Kogyo Co Ltd 接着剤組成物、及び接着フィルム
KR20140031117A (ko) * 2012-09-04 2014-03-12 동우 화인켐 주식회사 점착제 조성물

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Publication number Priority date Publication date Assignee Title
JPS5136771B2 (fr) * 1971-12-27 1976-10-12
WO2008053590A1 (fr) * 2006-10-30 2008-05-08 Sumitomo Bakelite Co., Ltd. Composition de résine liquide, tranche semi-conductrice avec couche adhésive, élément semi-conducteur avec couche adhésive, boîtier semi-conducteur, procédé de fabrication d'un élément semi-conducteur et procédé de fabrication d'un boîtier semi-con

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4880487A (en) * 1988-06-24 1989-11-14 Hoechst Celanese Corporation Hot melt adhesives containing poly(p-hydroxystyrene) homopolymers and copolymers and bonding methods employing same
KR20070021128A (ko) * 2004-01-16 2007-02-22 테사 악티엔게젤샤프트 배향된 아크릴레이트 접착 물질, 이의 제조 방법 및 용도
KR20080100852A (ko) * 2006-04-14 2008-11-19 오츠카 가가쿠 가부시키가이샤 수지 조성물 및 내열성 점착제
KR20100131423A (ko) * 2008-01-31 2010-12-15 닛토덴코 가부시키가이샤 편광자 보호 필름, 편광판 및 화상 표시 장치
JP2011032412A (ja) * 2009-08-04 2011-02-17 Tokyo Ohka Kogyo Co Ltd 接着剤組成物、及び接着フィルム
KR20140031117A (ko) * 2012-09-04 2014-03-12 동우 화인켐 주식회사 점착제 조성물

Also Published As

Publication number Publication date
KR20150046907A (ko) 2015-05-04
CN105473677B (zh) 2017-10-17
KR101918623B1 (ko) 2018-11-14
TW201516107A (zh) 2015-05-01
CN105473677A (zh) 2016-04-06

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