JP4927856B2 - Adhesive composition containing organosilane compound for adhesive for polarizing plate of liquid crystal display device - Google Patents
Adhesive composition containing organosilane compound for adhesive for polarizing plate of liquid crystal display device Download PDFInfo
- Publication number
- JP4927856B2 JP4927856B2 JP2008536497A JP2008536497A JP4927856B2 JP 4927856 B2 JP4927856 B2 JP 4927856B2 JP 2008536497 A JP2008536497 A JP 2008536497A JP 2008536497 A JP2008536497 A JP 2008536497A JP 4927856 B2 JP4927856 B2 JP 4927856B2
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- JP
- Japan
- Prior art keywords
- adhesive
- polarizing plate
- liquid crystal
- display device
- crystal display
- Prior art date
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- 239000000853 adhesive Substances 0.000 title claims abstract description 37
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 37
- -1 organosilane compound Chemical class 0.000 title claims abstract description 36
- 239000000203 mixture Substances 0.000 title claims abstract description 28
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 11
- 239000000126 substance Substances 0.000 claims description 24
- 239000004925 Acrylic resin Substances 0.000 claims description 10
- 229920000178 Acrylic resin Polymers 0.000 claims description 10
- XWERYQNBEFQKJM-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-cyanoacetate Chemical compound CO[Si](OC)(OC)CCCOC(=O)CC#N XWERYQNBEFQKJM-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- BCZOHPNAYUGLQG-UHFFFAOYSA-N 2-cyano-n-methyl-n-(3-trimethoxysilylpropyl)acetamide Chemical group CO[Si](OC)(OC)CCCN(C)C(=O)CC#N BCZOHPNAYUGLQG-UHFFFAOYSA-N 0.000 claims description 6
- 239000003377 acid catalyst Substances 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 239000011342 resin composition Substances 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- 238000006140 methanolysis reaction Methods 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 229920005992 thermoplastic resin Polymers 0.000 claims description 2
- 229920001187 thermosetting polymer Polymers 0.000 claims description 2
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 claims description 2
- 239000005052 trichlorosilane Substances 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims 1
- 239000012346 acetyl chloride Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000000758 substrate Substances 0.000 abstract description 8
- 229910000077 silane Inorganic materials 0.000 abstract description 6
- 239000004820 Pressure-sensitive adhesive Substances 0.000 abstract 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 15
- 239000011347 resin Substances 0.000 description 12
- 229920005989 resin Polymers 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- 239000011159 matrix material Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- GEQZTCMVWVDEDF-UHFFFAOYSA-N 2-cyanoacetyl chloride Chemical compound ClC(=O)CC#N GEQZTCMVWVDEDF-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229920006243 acrylic copolymer Polymers 0.000 description 3
- 239000011247 coating layer Substances 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 239000011256 inorganic filler Substances 0.000 description 3
- 229910003475 inorganic filler Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229960004132 diethyl ether Drugs 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002635 aromatic organic solvent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LDKSTCHEYCNPDS-UHFFFAOYSA-L carbon monoxide;dichloroplatinum Chemical compound O=C=[Pt](Cl)(Cl)=C=O LDKSTCHEYCNPDS-UHFFFAOYSA-L 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- VIBDJEWPNNCFQO-UHFFFAOYSA-N ethane-1,1,2-triol Chemical compound OCC(O)O VIBDJEWPNNCFQO-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- DVYVMJLSUSGYMH-UHFFFAOYSA-N n-methyl-3-trimethoxysilylpropan-1-amine Chemical compound CNCCC[Si](OC)(OC)OC DVYVMJLSUSGYMH-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- UOMUPDCRXJLVGR-UHFFFAOYSA-N propane-1,2,2-triol Chemical compound CC(O)(O)CO UOMUPDCRXJLVGR-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/544—Silicon-containing compounds containing nitrogen
- C08K5/5475—Silicon-containing compounds containing nitrogen containing at least one C≡N bond
-
- 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
-
- 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
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/08—Homopolymers or copolymers of acrylic acid esters
-
- 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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/20—Adhesives in the form of films or foils characterised by their carriers
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Nonlinear Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polarising Elements (AREA)
- Adhesive Tapes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
本発明は、新規な有機シラン化合物に関する。より詳しくは有機樹脂と無機フィラーとの親和性を高める目的、あるいはマトリックス樹脂を含むコーティング層と基材との間の接着性を向上させる目的で多様な用途に有用であり、特に、液晶表示装置の偏光板用接着剤のガラス基板との接着性を向上させ、高温高湿下においても経時変化を少なくするために有用である、新規な有機シラン化合物に関するものである。 The present invention relates to a novel organosilane compound. More specifically, it is useful for various applications for the purpose of increasing the affinity between the organic resin and the inorganic filler, or for improving the adhesion between the coating layer containing the matrix resin and the base material. The present invention relates to a novel organosilane compound that is useful for improving the adhesion of a polarizing plate adhesive to a glass substrate and reducing a change with time even under high temperature and high humidity.
従来のシラン化合物を含有する接着剤組成物としては、エポキシ基を有するシラン化合物を含む接着剤組成物が開示されている（特許文献１参照）。また、炭化水素基を有するシラン化合物を含む接着剤組成物が開示されている（特許文献２参照）。 As an adhesive composition containing a conventional silane compound, an adhesive composition containing a silane compound having an epoxy group is disclosed (see Patent Document 1). Moreover, the adhesive composition containing the silane compound which has a hydrocarbon group is disclosed (refer patent document 2).
しかし、前記のようなシラン化合物を含む接着剤組成物の場合、基板または偏光板が実際に使用される環境において要求される程度の適切な接着力を保持することができず、高温高湿の条件で接着力が過度に上昇する、あるいは剥離後に接着剤が基材に残存するという問題点があった。
前記のような従来の技術の問題点を解決するために、本発明は、有機樹脂と無機フィラーとの親和性を高める目的、あるいはマトリックス樹脂を含むコーティング層と基材との間の接着性を向上させる目的で多様な用途に有用である新規な有機シラン化合物を提供することを目的とする。 In order to solve the problems of the prior art as described above, the present invention aims to increase the affinity between the organic resin and the inorganic filler, or the adhesion between the coating layer containing the matrix resin and the substrate. An object of the present invention is to provide a novel organosilane compound that is useful for various purposes for the purpose of improvement.
本発明の他の目的は、液晶表示装置の偏光板用接着剤に含有させると、ガラス基板との接着性を向上させ、高温高湿下においても経時変化を少なくする、新規な有機シラン化合物を提供することである。 Another object of the present invention is to provide a novel organosilane compound that, when incorporated in an adhesive for a polarizing plate of a liquid crystal display device, improves adhesion to a glass substrate and reduces aging even under high temperature and high humidity. Is to provide.
前記目的を達成するために、本発明は、下記化学式１で表される有機シラン化合物を提供する。
以下、本発明を詳しく説明する。 The present invention will be described in detail below.
本発明の新規な有機シラン化合物は化学式１で表されることを特徴とする。 The novel organosilane compound of the present invention is represented by Formula 1.
化学式１で表示される有機シラン化合物は、１段階（one‐step）のプロセスまたは２段階（two‐step）のプロセスで製造することができる。 The organosilane compound represented by Chemical Formula 1 can be manufactured by a one-step process or a two-step process.
１段階のプロセスでは、本有機シラン化合物は、１‐アルケニルシアノアセテートとトリアルコキシシランとを、塩化白金酸触媒、 カールシュテット（Karstedt）触媒（即ち、塩化白金酸とｓｙｍ‐ジビニルテトラメチルジシロキサンとの錯体）、ジクロロビストリフェニルフォスフィン白金（ＩＩ）、シス‐ジクロロビスアセトニトリル白金（ＩＩ）、またはジカルボニルジクロロ白金（ＩＩ）の存在下で反応させることによって製造することができる。好ましくは、触媒は、塩化白金酸または白金‐ビニルシロキサン錯体から選ばれる。あるいは、本有機シラン化合物は、３級アミンの存在下で、シアノアセチルクロライドとＮ‐アルキルアミノアルキルトリアルコキシドとを反応させることによって製造することもできる。 In a one-step process, the organosilane compound comprises 1-alkenyl cyanoacetate and trialkoxysilane, a chloroplatinic acid catalyst, a Karlstedt catalyst (ie, chloroplatinic acid and sym-divinyltetramethyldisiloxane). Complex), dichlorobistriphenylphosphine platinum (II), cis-dichlorobisacetonitrile platinum (II), or dicarbonyldichloroplatinum (II). Preferably, the catalyst is selected from chloroplatinic acid or a platinum-vinylsiloxane complex. Alternatively, the organosilane compound can also be produced by reacting cyanoacetyl chloride and N-alkylaminoalkyltrialkoxide in the presence of a tertiary amine.
有機シラン化合物を製造するための２段階のプロセスでは、先ず、１‐アルケニルシアノアセテートとトリクロロシランとを塩化白金酸触媒または白金‐ビニルシロキサン触媒の存在下で反応させた後、メタノールを用いて反応生成物のメタノリシス（methanolysis）を行うことによって新規有機シラン化合物を製造することができる。 In the two-step process for producing organosilane compounds, first, 1-alkenyl cyanoacetate and trichlorosilane are reacted in the presence of a chloroplatinic acid catalyst or a platinum-vinylsiloxane catalyst, and then reacted with methanol. A novel organosilane compound can be produced by methanolysis of the product.
化学式１で表される有機シラン化合物は、１‐アルケニルシアノアセテートとトリアルコキシシランとを塩化白金酸触媒の存在下で反応させることによって製造することもでき、３級アミンの存在下でシアノアセチルクロライドとＮ‐アルキルアミノアルキルトリアルコキシドとを反応させることによって製造することもできる。 The organosilane compound represented by Chemical Formula 1 can also be produced by reacting 1-alkenyl cyanoacetate with trialkoxysilane in the presence of a chloroplatinic acid catalyst, and cyanoacetyl chloride in the presence of a tertiary amine. It can also be produced by reacting N-alkylaminoalkyltrialkoxide with N-alkylaminoalkyltrialkoxide.
上記反応は、クロロホルム、メチレンクロライド、ジクロロエタン等のハロゲン化アルキル溶媒；テトラハイドロフラン、ジオキサン等のような環状エーテル溶媒；またはベンゼン、トルエン、キシレン等のような芳香族有機溶媒中で行うことができる。 The above reaction can be carried out in a halogenated alkyl solvent such as chloroform, methylene chloride, dichloroethane; a cyclic ether solvent such as tetrahydrofuran, dioxane or the like; or an aromatic organic solvent such as benzene, toluene, xylene or the like. .
反応は、１０乃至２００℃の温度範囲で実施されることが望ましく、より望ましくは５０乃至１５０℃の温度範囲で実施される。また、精製のために真空蒸留を実施することもできる。 The reaction is preferably performed in a temperature range of 10 to 200 ° C, more preferably in a temperature range of 50 to 150 ° C. Also, vacuum distillation can be performed for purification.
前記のような反応を通じて製造される化学式１で表される本発明の有機シラン化合物の置換基Ｒ１は、特に、水素であることが望ましい。 The substituent R 1 of the organosilane compound of the present invention represented by the chemical formula 1 produced through the above reaction is particularly preferably hydrogen.
化学式１で表される本発明の有機シラン化合物の具体例には、下記化学式２で表されるシアノアセトキシプロピルトリメトキシシラン、下記化学式３で表される Ｎ‐メチル‐Ｎ‐（３‐トリメトキシシリルプロピル）シアノアセトアミドが含まれる。
化学式１で表れる本発明の有機シラン化合物は、アクリル系樹脂組成物、熱硬化性樹脂組成物、または熱可塑性樹脂組成物等に使用するのに適している。 The organosilane compound of the present invention represented by Chemical Formula 1 is suitable for use in an acrylic resin composition, a thermosetting resin composition, a thermoplastic resin composition, or the like.
前記のような方法で製造される化学式１で表される本発明の新規な有機シラン化合物は、マトリックス樹脂に有用に用いることができる。基材に対する接着力を向上させる添加剤（接着促進剤）としての効果があるかを確認するために、本発明の有機シラン化合物を用いて、アクリル系マトリックス樹脂を合成し、ガラスに対する接着力を試験した。 The novel organosilane compound of the present invention represented by Chemical Formula 1 produced by the above method can be usefully used for a matrix resin. In order to confirm whether there is an effect as an additive (adhesion promoter) that improves the adhesion to the base material, the organic silane compound of the present invention is used to synthesize an acrylic matrix resin and to improve the adhesion to glass. Tested.
アクリル系マトリックス樹脂は、炭素数１乃至１２のアルキル基を有する（メタ）アクリル酸エステルモノマーと水酸基を含むビニル系モノマーとを共重合させることによって得ることができる。 The acrylic matrix resin can be obtained by copolymerizing a (meth) acrylic acid ester monomer having an alkyl group having 1 to 12 carbon atoms and a vinyl monomer containing a hydroxyl group.
炭素数１乃至１２のアルキル基を有する（メタ）アクリル酸エステルモノマーとして、ブチル（メタ）アクリレート、２‐エチルヘキシル（メタ）アクリレート、エチル（メタ）アクリレート、メチル（メタ）アクリレート、ｎ‐プロピル（メタ）アクリレート、イソプロピル（メタ）アクリレート、ｔ‐ブチル（メタ）アクリレート、ペンチル（メタ）アクリレート、ｎ‐オクチル（メタ）アクリレート、イソオクチル（メタ）アクリレート、またはイソノニル（メタ）アクリレート等を、単独または２種以上混合して使用することができる。また、前記水酸基を含むビニル系モノマーとして、２‐ヒドロキシエチル（メタ）アクリレート、２‐ヒドロキシプロピル（メタ）アクリレート、２‐ヒドロキシエチレングリコール（メタ）アクリレート、または２‐ヒドロキシプロピレングリコール（メタ）アクリレート等を使用することができる。 Examples of the (meth) acrylic acid ester monomer having an alkyl group having 1 to 12 carbon atoms include butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, ethyl (meth) acrylate, methyl (meth) acrylate, n-propyl (meth) ) Acrylate, isopropyl (meth) acrylate, t-butyl (meth) acrylate, pentyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, or isononyl (meth) acrylate, alone or in combination They can be used in combination. Examples of the vinyl monomer containing a hydroxyl group include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxyethylene glycol (meth) acrylate, and 2-hydroxypropylene glycol (meth) acrylate. Can be used.
前記試験において、化学式１で表される本発明の有機シラン化合物およびアクリル系マトリックス樹脂に加えて、架橋剤を使用することができる。この架橋剤として、トリレンジイソシアナート、ジフェニルメタンジイソシアナート、ヘキサメチレンジイソシアナート、またはトリレンジイソシアナートのトリメチロールプロパン付加体等を使用することができる。 In the test, a crosslinking agent can be used in addition to the organosilane compound of the present invention represented by Chemical Formula 1 and the acrylic matrix resin. As the crosslinking agent, tolylene diisocyanate, diphenylmethane diisocyanate, hexamethylene diisocyanate, or a trimethylolpropane adduct of tolylene diisocyanate can be used.
また、前記アクリル系マトリックス樹脂に、必要に応じて、可塑剤、アクリル系オリゴマー、乳化剤、複屈折性低分子量化合物、エポキシ樹脂、硬化剤、紫外線安定剤、酸化防止剤、着色剤、改質剤、または フィラー等の添加剤を添加することもできる。 In addition, the acrylic matrix resin may include a plasticizer, an acrylic oligomer, an emulsifier, a birefringent low molecular weight compound, an epoxy resin, a curing agent, an ultraviolet stabilizer, an antioxidant, a colorant, and a modifier as necessary. Or additives such as fillers can be added.
以下、本発明の理解を助けるために望ましい実施例を提示するが、下記の実施例は本発明を例示するものであり、本発明の範囲が下記の実施例に限定されるものではない。 Hereinafter, preferred examples are presented to help the understanding of the present invention. However, the following examples illustrate the present invention, and the scope of the present invention is not limited to the following examples.
［実施例１］：シアノアセトキシプロピルトリメトキシシラン （cyanoacetoxypropyl trimethoxy silane、化学式２）の合成
温度計と凝縮機が備えられた１Ｌの反応器に、ＴＨＦ２００ｍＬ、アルキルシアノアセテート４０ｇ（０．３１９ｍｏｌ）、及びトリメトキシシラン４０ｇ（０．３２７ｍｏｌ）を入れた。温度を６０℃に高めた後、塩化白金酸０．０５ｇを添加し４時間反応させた。反応終了後、溶媒及び未反応物を除去し、真空蒸留して、シアノアセトキシプロピルトリメトキシシラン（化学式２）７３ｇを得た。収率は９１％であった。
[Example 1]: Synthesis of cyanoacetoxypropyl trimethoxysilane (Chemical Formula 2) In a 1 L reactor equipped with a thermometer and a condenser, 200 mL of THF, 40 g of alkyl cyanoacetate (0.319 mol), and 40 g (0.327 mol) of trimethoxysilane was added. After raising the temperature to 60 ° C., 0.05 g of chloroplatinic acid was added and allowed to react for 4 hours. After completion of the reaction, the solvent and unreacted substances were removed and vacuum distillation was performed to obtain 73 g of cyanoacetoxypropyltrimethoxysilane (Chemical Formula 2). The yield was 91%.
製造したシアノアセトキシプロピルトリメトキシシランは、無色の液体であった。ＮＭＲ分析の結果は次の通りである。
1Ｈ ＮＭＲ（ＣＤＣｌ３、３００ＭＨｚ）：０．７０（ｔ、２Ｈ）、１．８３（ｐ、２Ｈ）、３．５０（ｓ、２Ｈ）、３．６１（ｓ、９Ｈ）、４．２２（ｔ、 ２Ｈ）
１３Ｃ ＮＭＲ（ＣＤＣｌ３、３００ＭＨｚ）：４．６、２１．４、２４．０、 ４９．９、６７．９、１１３．３、１６３．１
The produced cyanoacetoxypropyltrimethoxysilane was a colorless liquid. The results of NMR analysis are as follows.
1 H NMR (CDCl 3 , 300 MHz): 0.70 (t, 2H), 1.83 (p, 2H), 3.50 (s, 2H), 3.61 (s, 9H), 4.22 ( t, 2H)
13 C NMR (CDCl 3 , 300 MHz): 4.6, 21.4, 24.0, 49.9, 67.9, 113.3, 163.1
［実施例２］：Ｎ‐メチル‐Ｎ‐（３‐トリメトキシシリルプロピル）シアノアセトアミド（N-methyl-N-(3-trimethoxysilylpropyl)cyanoacetamide、化学式３）の合成
温度計、凝縮機、及び滴下用ガラスボトルが備えられた１Ｌの反応器に、ジエチルエテール２００ｍＬ及びシアノアセチルクロライド１１ｇ（０．１１ｍｏｌ）を入れ、常温、窒素雰囲気で攪拌した。Ｎ‐メチルアミノプロピルメトキシシラン（N-methylaminopropyl trimethoxysilane）２０ｇ（０．１０４ｍｏｌ）及びピリジン１１ｇ（０．１４ｍｏｌ）をジエチルエテール１００ｍＬに溶解した溶液を、滴下用ガラス漏斗を用いて反応器に徐々に添加した。この反応物を２時間間常温で攪拌した後、沈殿したピリジニウム塩、溶媒、及び未反応物を除去した後、真空蒸留して、Ｎ‐メチル‐Ｎ‐（３‐トリメトキシシリルプロピル）シアノアセトアミド（化学式３）２１ｇを得た。収率は７５％であった。
Example 2 Synthesis of N-methyl-N- (3-trimethoxysilylpropyl) cyanoacetamide (N-methyl-N- (3-trimethoxysilylpropyl) cyanoacetamide, Chemical Formula 3) Thermometer, condenser, and dropping In a 1 L reactor equipped with a glass bottle, 200 mL of diethyl ether and 11 g (0.11 mol) of cyanoacetyl chloride were added and stirred at room temperature in a nitrogen atmosphere. A solution prepared by dissolving 20 g (0.104 mol) of N-methylaminopropyl trimethoxysilane and 11 g (0.14 mol) of pyridine in 100 mL of diethylether is gradually added to the reactor using a dropping funnel. Added. The reaction was stirred for 2 hours at room temperature, then the precipitated pyridinium salt, solvent and unreacted material was removed and then vacuum distilled to give N-methyl-N- (3-trimethoxysilylpropyl) cyanoacetamide. (Chemical formula 3) 21 g was obtained. The yield was 75%.
製造した Ｎ‐メチル‐Ｎ‐（３‐トリメトキシシリルプロピル）シアノアセトアミドは、無色の液体であった。ＮＭＲ分析の結果は次の通りである。
1Ｈ ＮＭＲ（ＣＤＣｌ３、３００ＭＨｚ）：０．６５（ｔ、２Ｈ）、１．２８（ｐ、２Ｈ）、２．９７（ｓ、３Ｈ）、３．３７（ｓ、９Ｈ）、３．４７（ｓ、９Ｈ）、３．５５（ｔ、 ２Ｈ）
１３Ｃ ＮＭＲ（ＣＤＣｌ３、３００ＭＨｚ）：３．５４、２１．０、２４．９５、３６．０１、４８．５７、５０．７３、１１５．１９、１６２．３２
The produced N-methyl-N- (3-trimethoxysilylpropyl) cyanoacetamide was a colorless liquid. The results of NMR analysis are as follows.
1 H NMR (CDCl 3 , 300 MHz): 0.65 (t, 2H), 1.28 (p, 2H), 2.97 (s, 3H), 3.37 (s, 9H), 3.47 ( s, 9H), 3.55 (t, 2H)
13 C NMR (CDCl 3 , 300 MHz): 3.54, 21.0, 24.95, 36.01, 48.57, 50.73, 115.19, 162.32
［実施例３］
（アクリル系共重合体の製造）
窒素ガスの還流ユニットと、温度調節が容易な冷却装置とが設けられた、１、０００ｃｃの反応器に、ｎ‐エチルアクリレート（ＥＡ）９８重量部、及び２‐ヒドロキシエチルメタアクリレート（２‐ＨＥＭＡ）２重量部とを含む単量体混合物を投入した。その後、溶剤としてエチルアセテート（ＥＡｃ）２３０重量部を投入した。酸素を除去するために窒素ガスを２０分間パージングした後、この反応器を７０℃で保持した。均一化した後、反応開始剤として、エチルアセテート中５０％の濃度に希釈したアゾビスイソブチロニトリル（ＡＩＢＮ）０．０３重量部を投入した。この混合物を７時間反応させた後、分子量が（ポリスチレンの標準サンプルを用いて測定して）９０万であるアクリル系共重合体が得られた。
[Example 3]
(Manufacture of acrylic copolymer)
A 1,000 cc reactor equipped with a nitrogen gas reflux unit and a cooling device with easy temperature control was charged with 98 parts by weight of n-ethyl acrylate (EA) and 2-hydroxyethyl methacrylate (2-HEMA). ) A monomer mixture containing 2 parts by weight was charged. Thereafter, 230 parts by weight of ethyl acetate (EAc) was added as a solvent. After purging with nitrogen gas for 20 minutes to remove oxygen, the reactor was held at 70 ° C. After homogenization, 0.03 parts by weight of azobisisobutyronitrile (AIBN) diluted to a concentration of 50% in ethyl acetate was added as a reaction initiator. After the mixture was reacted for 7 hours, an acrylic copolymer having a molecular weight of 900,000 (measured using a standard polystyrene sample) was obtained.
（アクリル系樹脂組成物の製造）
製造したアクリル系共重合体１００重量部に、多官能性イソシアネート系架橋剤としてトリメチロールプロパンのトリレンジイソシアナート付加物１．５重量部と、実施例１で合成したシアノアセトキシプロピルトリメトキシシラン（化学式２）０．１重量部とを添加した。この組成物を適切な濃度に希釈し、均一に混合した後、ＰＥＴフィルム上にコーティングした。
(Manufacture of acrylic resin composition)
To 100 parts by weight of the produced acrylic copolymer, 1.5 parts by weight of a tolylene diisocyanate adduct of trimethylolpropane as a polyfunctional isocyanate-based crosslinking agent, and the cyanoacetoxypropyltrimethoxysilane synthesized in Example 1 ( Chemical formula 2) 0.1 part by weight was added. This composition was diluted to an appropriate concentration, mixed uniformly, and then coated on a PET film.
［実施例４］
実施例１で合成したシアノアセトキシプロピルトリメトキシシラン（化学式２）の代わりに、実施例２で合成したＮ‐メチル‐Ｎ‐（３‐トリメトキシシリルプロピル）シアノアセトアミド（化学式３）を使用したことを除いて、実施例３と同一の方法でアクリル系樹脂組成物の製造を実施した。
[Example 4]
Use of N-methyl-N- (3-trimethoxysilylpropyl) cyanoacetamide (Chemical Formula 3) synthesized in Example 2 instead of cyanoacetoxypropyltrimethoxysilane (Chemical Formula 2) synthesized in Example 1 Except for, the acrylic resin composition was produced in the same manner as in Example 3.
［比較例１］
実施例１で合成したシアノアセトキシプロピルトリメトキシシラン（化学式２）を添加しなかったことを除いて、実施例３と同一の方法でアクリル系樹脂組成物の製造を実施した。
[Comparative Example 1]
An acrylic resin composition was produced in the same manner as in Example 3 except that cyanoacetoxypropyltrimethoxysilane (Chemical Formula 2) synthesized in Example 1 was not added.
［比較例２］
実施例１で合成したシアノアセトキシプロピルトリメトキシシラン（化学式２）の代わりに３‐ グリシドキシプロピルトリメトキシシラン（glycidoxypropyl)trimethoxysilane）を使用したことを除いては実施例３と同一の方法でアクリル系樹脂組成物の製造を実施した。
[Comparative Example 2]
An acrylic resin was prepared in the same manner as in Example 3 except that 3-glycidoxypropyl trimethoxysilane was used instead of cyanoacetoxypropyltrimethoxysilane (chemical formula 2) synthesized in Example 1. Production of a resin-based resin composition was carried out.
〔接着力の測定〕
実施例３乃至４及び比較例１乃至２で製造したアクリル系樹脂組成物のガラスに対する接着力を次のような方法で評価した。
[Measurement of adhesive strength]
The adhesive strength of the acrylic resin compositions produced in Examples 3 to 4 and Comparative Examples 1 and 2 to glass was evaluated by the following method.
実施例３乃至４及び比較例１乃至２で製造したアクリル系樹脂組成物がそれぞれコーティングされたＰＥＴフィルムを、清潔なガラス板と共に加圧ローラーを用いてラミネートし、常温で１時間間保持した。その後、ｉ）常温条件（常温で１０時間間放置）、ｉｉ）ｄｒｙ条件（６０℃の温度で１０時間放置）、およびｉｉｉ）ｗｅｔ条件（６０℃、９０％相対湿度の条件で１０時間放置）に保持した後、再び常温で２時間保持した。次いで、 引張試験機を用いて３００ｍｍ／分の速度および１８０°の剥離角度でガラスに対する接着力（１８０℃ 剥離強度）を測定した。結果を下記表１に示す。 The PET films coated with the acrylic resin compositions produced in Examples 3 to 4 and Comparative Examples 1 to 2 were laminated with a clean glass plate using a pressure roller, and held at room temperature for 1 hour. Then, i) normal temperature conditions (left at normal temperature for 10 hours), ii) dry conditions (left at 60 ° C. for 10 hours), and iii) wet conditions (left at 60 ° C., 90% relative humidity for 10 hours) And then held again at room temperature for 2 hours. Subsequently, the adhesive strength (180 degreeC peeling strength) with respect to glass was measured with the speed | rate of 300 mm / min and the peeling angle of 180 degrees using the tensile tester. The results are shown in Table 1 below.
表１に示したように、本発明の化学式１で表される新規な有機シラン化合物を用いた実施例３及び４のアクリル系樹脂組成物は、比較例１及び２のアクリル系樹脂組成物と比べて、常温条件、ｄｒｙ条件、ｗｅｔ条件の全てにおいて、ガラス接着力に優れていることが分かる。 As shown in Table 1, the acrylic resin compositions of Examples 3 and 4 using the novel organosilane compound represented by Chemical Formula 1 of the present invention are the same as the acrylic resin compositions of Comparative Examples 1 and 2. In comparison, it can be seen that the glass adhesive force is excellent in all of the room temperature conditions, the dry conditions, and the wet conditions.
本発明による新規な有機シラン化合物は、有機樹脂と無機フィラーとの親和性を高める目的、あるいはマトリックス樹脂を含むコーティング層と基材との間の接着性を向上させる目的で多様な用途に有用であり、特に、液晶表示装置の偏光板用接着剤のガラス基板との接着性を向上させ、高温高湿下における経時変化を低下させるために有用である。 The novel organosilane compound according to the present invention is useful for various applications for the purpose of increasing the affinity between the organic resin and the inorganic filler, or for improving the adhesion between the coating layer containing the matrix resin and the substrate. In particular, it is useful for improving the adhesiveness of the adhesive for a polarizing plate of a liquid crystal display device to a glass substrate and reducing the change with time under high temperature and high humidity.
これまで、本発明の概念および具体例を詳しく説明してきたが、これらの記載に基づいて、本発明の技術思想の範囲内で他の多様な変形及び修正が可能であることが当業者に理解されるであろう。当業者であれば、このような変形及び修正が添付された特許請求の精神および範囲に包含されること理解するであろう。 Although the concept and specific examples of the present invention have been described in detail so far, those skilled in the art will understand that various other variations and modifications can be made within the scope of the technical idea of the present invention based on these descriptions. Will be done. Those skilled in the art will appreciate that such changes and modifications are encompassed within the spirit and scope of the appended claims.
Claims (8)
前記有機シラン化合物が下記化学式１：
で表される、接着剤組成物。 An adhesive composition for an adhesive for a polarizing plate of a liquid crystal display device comprising an organosilane compound,
The organosilane compound is represented by the following chemical formula 1 :
An adhesive composition represented by:
下記化学式３：
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2005-0099190 | 2005-10-20 | ||
| KR20050099190 | 2005-10-20 | ||
| KR10-2005-0127182 | 2005-12-21 | ||
| KR1020050127182A KR100822142B1 (en) | 2005-10-20 | 2005-12-21 | Novel organic silane compound |
| PCT/KR2006/004264 WO2007046646A1 (en) | 2005-10-20 | 2006-10-19 | Novel organic silane compound |
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| JP2009512683A JP2009512683A (en) | 2009-03-26 |
| JP4927856B2 true JP4927856B2 (en) | 2012-05-09 |
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| JP2008536497A Active JP4927856B2 (en) | 2005-10-20 | 2006-10-19 | Adhesive composition containing organosilane compound for adhesive for polarizing plate of liquid crystal display device |
| JP2008536498A Active JP4819128B2 (en) | 2005-10-20 | 2006-10-19 | Adhesive composition |
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| JP2008536498A Active JP4819128B2 (en) | 2005-10-20 | 2006-10-19 | Adhesive composition |
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| JP (2) | JP4927856B2 (en) |
| KR (2) | KR100840114B1 (en) |
| CN (2) | CN101291941B (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR100840114B1 (en) * | 2005-10-20 | 2008-06-19 | 주식회사 엘지화학 | Pressure-sensitive adhesive composition |
| JP4448183B2 (en) * | 2007-09-28 | 2010-04-07 | 日東電工株式会社 | Polarizing plate, manufacturing method thereof, optical film, and image display device |
| KR101042214B1 (en) * | 2009-04-09 | 2011-06-20 | 주식회사 엘지화학 | An alignment film composition, an alignment film prepared therefrom, a method for manufacturing an alignment film, an optical film comprising the same, and a display device including the optical film |
| KR101628091B1 (en) * | 2010-02-02 | 2016-06-08 | 동우 화인켐 주식회사 | Adhesive composition and polarizing plate comprising the same |
| KR101707863B1 (en) * | 2010-12-27 | 2017-02-17 | 미쓰비시 쥬시 가부시끼가이샤 | Mold release film |
| KR101435252B1 (en) | 2012-03-30 | 2014-08-28 | 주식회사 엘지화학 | Pressure sensitive adhesive tape |
| KR101466230B1 (en) * | 2013-06-14 | 2014-11-28 | 주식회사 연우 | Removable adhesive composition, method for preparing thereof, adhesive film comprising removable adhesive composition and method for manufacturing thereof |
| KR101391297B1 (en) | 2013-07-22 | 2014-05-02 | 동우 화인켐 주식회사 | Adhesive composition |
| KR101692609B1 (en) * | 2014-02-26 | 2017-01-03 | 주식회사 엘지화학 | Encapsulant for light module, method for manufacturing the same and light module comprising the same |
| CN107407765A (en) * | 2015-03-24 | 2017-11-28 | 综研化学株式会社 | Polarizer and its manufacture method with adhesive phase |
| CN105838294B (en) * | 2016-05-30 | 2018-09-11 | 成都市惠家胶粘制品有限公司 | The preparation process of high temperature resistant line paper self-adhesive tape |
| KR102335316B1 (en) * | 2017-12-27 | 2021-12-06 | 주식회사 엘지화학 | Adhesive composition and protection film using the same |
| KR102238704B1 (en) * | 2018-12-21 | 2021-04-08 | 주식회사 엘지화학 | Cross-linking agent compound, photosensitive composition comprising the same, and photosensitive material using the same |
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| JPH0572723A (en) * | 1991-09-12 | 1993-03-26 | Fuji Photo Film Co Ltd | Photosensitive composition |
| JP4819128B2 (en) * | 2005-10-20 | 2011-11-24 | エルジー・ケム・リミテッド | Adhesive composition |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101292007A (en) | 2008-10-22 |
| JP4819128B2 (en) | 2011-11-24 |
| DE602006020608D1 (en) | 2011-04-21 |
| KR20070043558A (en) | 2007-04-25 |
| CN101291941B (en) | 2011-08-17 |
| TWI324627B (en) | 2010-05-11 |
| KR100840114B1 (en) | 2008-06-19 |
| CN101291941A (en) | 2008-10-22 |
| KR100822142B1 (en) | 2008-04-14 |
| TW200716657A (en) | 2007-05-01 |
| JP2009512753A (en) | 2009-03-26 |
| TWI304405B (en) | 2008-12-21 |
| KR20070043557A (en) | 2007-04-25 |
| ATE501228T1 (en) | 2011-03-15 |
| TW200716718A (en) | 2007-05-01 |
| JP2009512683A (en) | 2009-03-26 |
| CN101292007B (en) | 2012-07-25 |
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