KR20160096958A - Adhesive Composition and Polarizing Plate Comprising the Same - Google Patents
Adhesive Composition and Polarizing Plate Comprising the Same Download PDFInfo
- Publication number
- KR20160096958A KR20160096958A KR1020150018694A KR20150018694A KR20160096958A KR 20160096958 A KR20160096958 A KR 20160096958A KR 1020150018694 A KR1020150018694 A KR 1020150018694A KR 20150018694 A KR20150018694 A KR 20150018694A KR 20160096958 A KR20160096958 A KR 20160096958A
- Authority
- KR
- South Korea
- Prior art keywords
- pressure
- sensitive adhesive
- group
- adhesive composition
- acrylate
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 34
- 239000000853 adhesive Substances 0.000 title abstract description 24
- 230000001070 adhesive effect Effects 0.000 title abstract description 24
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 37
- 229920006243 acrylic copolymer Polymers 0.000 claims abstract description 24
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 22
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 16
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 10
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 10
- 239000012948 isocyanate Substances 0.000 claims abstract description 9
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 8
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 52
- 239000000178 monomer Substances 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 13
- 239000010410 layer Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 210000002858 crystal cell Anatomy 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 229920001577 copolymer Polymers 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 description 38
- -1 silane compound Chemical class 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 13
- 239000000758 substrate Substances 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 5
- 230000007797 corrosion Effects 0.000 description 5
- 238000005260 corrosion Methods 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 239000002216 antistatic agent Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000012790 adhesive layer Substances 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XBTRYWRVOBZSGM-UHFFFAOYSA-N (4-methylphenyl)methanediamine Chemical compound CC1=CC=C(C(N)N)C=C1 XBTRYWRVOBZSGM-UHFFFAOYSA-N 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- BNCADMBVWNPPIZ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COCN(COC)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 BNCADMBVWNPPIZ-UHFFFAOYSA-N 0.000 description 1
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 1
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- NASFLIJUMKUCFU-UHFFFAOYSA-N CC(C(OCCCN(O)O)=O)=C Chemical compound CC(C(OCCCN(O)O)=O)=C NASFLIJUMKUCFU-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- YGCOKJWKWLYHTG-UHFFFAOYSA-N [[4,6-bis[bis(hydroxymethyl)amino]-1,3,5-triazin-2-yl]-(hydroxymethyl)amino]methanol Chemical compound OCN(CO)C1=NC(N(CO)CO)=NC(N(CO)CO)=N1 YGCOKJWKWLYHTG-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000004299 exfoliation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- CWGQLCONGDBUKZ-UHFFFAOYSA-N heptane-1,5,5,6-tetrol Chemical compound OCCCCC(C(C)O)(O)O CWGQLCONGDBUKZ-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 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 1
- 239000013638 trimer Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000004260 weight control Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C07F7/0834—Compounds having one or more O-Si linkage
-
- 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
- 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
-
- 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
- C09J201/00—Adhesives based on unspecified macromolecular compounds
- C09J201/02—Adhesives based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
- C09J201/10—Adhesives based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing hydrolysable silane groups
-
- 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
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Nonlinear Science (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polarising Elements (AREA)
Abstract
Description
본 발명은 점착제 조성물 및 이를 포함하는 편광판에 관한 것으로, 보다 상세하게는 점착력이 높고, 내구성 및 리워크성이 우수한 점착제 조성물, 이를 포함하는 편광판 및 액정표시장치에 관한 것이다.The present invention relates to a pressure-sensitive adhesive composition and a polarizing plate comprising the same, and more particularly, to a pressure-sensitive adhesive composition having a high adhesive strength and excellent durability and reworkability, a polarizing plate and a liquid crystal display including the same.
액정표시장치(Liquid crystal display device, LCD)는 액정셀과 상기 액정셀의 양면에 점착제층을 매개로 접합된 편광판을 포함하는 액정패널을 구비한다.2. Description of the Related Art A liquid crystal display device (LCD) includes a liquid crystal cell and a liquid crystal panel including a polarizing plate bonded to both sides of the liquid crystal cell via an adhesive layer.
액정셀과 편광판의 접합을 위한 점착제는 기재와의 밀착성, 빛샘 방지성, 내열 및 내습열 내구성뿐만 아니라 리워크성(재박리성)과 같은 물성을 동시에 만족시켜야 한다. 이 중에서도 특히 내구성과 리워크성을 만족시키기 위해서 요구되는 점착제의 특성이 서로 상충되기 때문에 이들 모두를 만족시키는 것은 완전히 해결되지 못하고 있다.The pressure-sensitive adhesive for bonding the liquid crystal cell and the polarizing plate should satisfy not only the adhesion to the substrate, the light-shielding property, the heat resistance and the resistance to moisture and heat, but also the physical properties such as reworkability (re-peelability). Among them, the properties of the pressure-sensitive adhesive required to satisfy the durability and the workability are in conflict with each other, so that satisfying all of them is not completely solved.
상기한 바와 같은 문제를 해결하기 위하여, 점착제에 실란커플링제를 첨가하는 방법이 제안되었다. 일본공개특허 평 8-104855호에는 기판의 표면에 편광판을 양호한 접착 강도로 접착할 수 있을 뿐만 아니라, 필요에 따라 기판에 손상을 주거나 점착제를 잔존시키지 않고 기판의 표면으로부터 편광판을 박리하기 위하여 아크릴계 폴리머에 β-케토에스테르기와 알콕시기를 가지는 실란 화합물이 함유된 점착제 조성물이 개시되어 있다.In order to solve the above problems, a method of adding a silane coupling agent to a pressure-sensitive adhesive has been proposed. Japanese Unexamined Patent Application, First Publication No. Hei 8-104855 discloses that not only a polarizing plate can be adhered to the surface of a substrate with good adhesive strength but also an acrylic polymer is used to peel the polarizing plate from the surface of the substrate without damaging the substrate or leaving a pressure- Discloses a pressure-sensitive adhesive composition containing a silane compound having a? -Keto ester group and an alkoxy group.
그러나, 상기 점착제 조성물은 고온 또는 고온 다습 조건에서 내구성이 저하되는 문제점이 있다. However, the pressure-sensitive adhesive composition has a problem that the durability of the pressure-sensitive adhesive composition deteriorates under high temperature or high temperature and high humidity conditions.
본 발명은 상기와 같은 문제점을 해결하기 위한 것으로, 본 발명의 한 목적은 점착력이 높고, 내구성 및 리워크성이 우수한 점착제 조성물을 제공하는 것이다.DISCLOSURE OF THE INVENTION An object of the present invention is to provide a pressure-sensitive adhesive composition having high adhesion and excellent durability and reworkability.
본 발명의 다른 목적은 상기 점착제 조성물로 이루어진 점착제층이 적층된 편광판을 제공하는 것이다.Another object of the present invention is to provide a polarizing plate in which a pressure-sensitive adhesive layer composed of the pressure-sensitive adhesive composition is laminated.
본 발명의 또 다른 목적은 액정셀의 적어도 한 면에 상기 편광판이 구비된 액정표시장치를 제공하는 것이다.It is still another object of the present invention to provide a liquid crystal display having the polarizing plate on at least one side of a liquid crystal cell.
한편으로, 본 발명은 산가가 1㎎KOH/g 이하인 실란기를 함유하는 아크릴계 공중합체, 이소시아네이트계 가교제 및 에틸렌옥사이드기를 함유하는 (메타)아크릴레이트를 포함하는 점착제 조성물을 제공한다.On the other hand, the present invention provides a pressure-sensitive adhesive composition comprising an acrylic copolymer containing an silane group having an acid value of 1 mgKOH / g or less, an isocyanate-based crosslinking agent and (meth) acrylate containing an ethylene oxide group.
본 발명의 일 실시형태에서, 상기 아크릴계 공중합체는 탄소수 1-12의 알킬기를 갖는 (메타)아크릴레이트 단량체, 히드록시기를 갖는 단량체 및 실란기를 갖는 단량체의 공중합체일 수 있다.In one embodiment of the present invention, the acrylic copolymer may be a copolymer of a (meth) acrylate monomer having an alkyl group having 1-12 carbon atoms, a monomer having a hydroxy group and a monomer having a silane group.
본 발명의 일 실시형태에서, 상기 실란기를 갖는 단량체는 하기 화학식 1의 화합물을 포함할 수 있다. In one embodiment of the present invention, the monomer having a silane group may include a compound represented by the following formula (1).
[화학식 1][Chemical Formula 1]
상기 식에서,In this formula,
A는 C1-C10의 알킬렌기 또는 -(CH2)p-L-(CH2)q-이고,A is a C 1 -C 10 alkylene group or - (CH 2 ) p -L- (CH 2 ) q -
L은 -NHCOO-, NH 또는 O, 바람직하게는 -NHCOO-이며,L is -NHCOO-, NH or O, preferably -NHCOO-,
R1은 수소 또는 메틸이고, R < 1 > is hydrogen or methyl,
R2는 C1-C6의 알킬기 또는 C1-C6의 알콕시기, 바람직하게는 메틸, 메톡시 또는 에톡시이며,R 2 is a C 1 -C 6 alkyl group or a C 1 -C 6 alkoxy group, preferably methyl, methoxy or ethoxy,
p 및 q는 각각 독립적으로 1 내지 5의 정수이다. p and q are each independently an integer of 1 to 5;
본 발명의 일 실시형태에서, 상기 에틸렌옥사이드기를 함유하는 (메타)아크릴레이트는 하기 화학식 6의 화합물을 포함할 수 있다.In one embodiment of the present invention, the (meth) acrylate containing the ethylene oxide group may include a compound of the following formula (6).
[화학식 6][Chemical Formula 6]
상기 식에서,In this formula,
X는 수소 또는 메틸이고,X is hydrogen or methyl,
n은 5 내지 25의 정수이다.
n is an integer of 5 to 25;
다른 한편으로, 본 발명은 상기 점착제 조성물로 이루어진 점착제층이 적층된 편광판을 제공한다.On the other hand, the present invention provides a polarizing plate in which a pressure-sensitive adhesive layer composed of the pressure-sensitive adhesive composition is laminated.
또 다른 한편으로, 본 발명은 액정셀의 적어도 한 면에 상기 편광판이 구비된 액정표시장치를 제공한다.On the other hand, the present invention provides a liquid crystal display in which the polarizing plate is provided on at least one surface of a liquid crystal cell.
본 발명에 따른 점착제 조성물은 점착력이 우수할 뿐만 아니라 내구성 및 리워크성을 동시에 만족시킬 수 있고 금속 산화물에 대한 부식성이 낮아 편광판을 액정셀에 접합시키는데 효과적으로 사용될 수 있다.The pressure-sensitive adhesive composition according to the present invention can be used effectively for bonding a polarizing plate to a liquid crystal cell because it has both excellent durability and reworkability and low corrosiveness against metal oxides.
이하, 본 발명을 보다 상세히 설명한다.
Hereinafter, the present invention will be described in more detail.
본 발명의 일 실시형태는 산가가 1㎎KOH/g 이하인 실란기를 함유하는 아크릴계 공중합체, 이소시아네이트계 가교제 및 에틸렌옥사이드기를 함유하는 (메타)아크릴레이트를 포함하는 점착제 조성물에 관한 것이다.
An embodiment of the present invention relates to a pressure-sensitive adhesive composition comprising an acrylic copolymer containing an silane group having an acid value of 1 mg KOH / g or less, an isocyanate-based crosslinking agent and (meth) acrylate containing an ethylene oxide group.
본 발명의 일 실시형태에서, 상기 아크릴계 공중합체는 산성기, 예컨대 카르복시기를 함유하지 않는 산 비함유 공중합체로서, 산가가 1 ㎎KOH/g 이하이다. 산가가 1 ㎎KOH/g 초과, 즉 산 함유 공중합체인 경우에는 초기 점착력의 조절이 어려워 리워크성(재박리성)의 확보가 어려울 수 있으며, 금속 산화물이 코팅된 액정셀에 적용 시 금속 산화물의 부식을 야기할 수 있다.In one embodiment of the present invention, the acrylic copolymer is an acidic group, for example, an acid-free copolymer containing no carboxyl group, and has an acid value of 1 mgKOH / g or less. When the acid value is more than 1 mgKOH / g, that is, in the case of an acid-containing copolymer, it is difficult to control the initial cohesive force and it may be difficult to secure the reworkability (re-releasability). In application to a liquid crystal cell coated with a metal oxide, It can cause corrosion.
본 발명에 따른 아크릴계 공중합체는 산성기를 갖는 단량체의 사용을 배제하고 실란기를 갖는 단량체를 사용하여, 고온에서 실란기가 활성화됨으로써 산 성분을 대신하여 기재와의 밀착력을 향상시킬 수 있다.
The acrylic copolymer according to the present invention can improve adhesion with a substrate in place of an acid component by using a monomer having a silane group, by excluding the use of a monomer having an acidic group and activating the silane group at a high temperature.
본 발명의 일 실시형태에서, 상기 아크릴계 공중합체는 탄소수 1-12의 알킬기를 갖는 (메타)아크릴레이트 단량체, 히드록시기를 갖는 단량체 및 실란기를 갖는 단량체의 공중합체일 수 있다. 여기서, (메타)아크릴레이트는 아크릴레이트 및 메타크릴레이트를 의미한다.
In one embodiment of the present invention, the acrylic copolymer may be a copolymer of a (meth) acrylate monomer having an alkyl group having 1-12 carbon atoms, a monomer having a hydroxy group and a monomer having a silane group. 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, 2-에틸부틸(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, n-노닐(메타)아크릴레이트, 이소노닐(메타)아크릴레이트, 데실(메타)아크릴레이트, 라우릴(메타)아크릴레이트, 도데실(메타)아크릴레이트 등을 들 수 있으며, 이들은 단독 또는 2종 이상 혼합하여 사용할 수 있다. Examples of the (meth) acrylate monomer having an alkyl group having 1-12 carbon atoms include n-butyl (meth) acrylate, 2-butyl (meth) acrylate, (Meth) acrylate, ethyl (meth) acrylate, methyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (Meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, n-octyl , And dodecyl (meth) acrylate. These may be used alone or in combination of two or more.
탄소수 1-12의 알킬기를 갖는 (메타)아크릴레이트 단량체는 아크릴계 공중합체의 제조에 사용되는 총 단량체 100중량%에 대하여 90 내지 98중량%로 포함되는 것이 바람직하다. 함량이 90중량% 미만인 경우 점착력이 충분하지 못하고, 98중량% 초과인 경우 응집력이 저하될 수 있다.
The (meth) acrylate monomer having an alkyl group having from 1 to 12 carbon atoms is preferably contained in an amount of 90 to 98% by weight based on 100% by weight of the total monomers used in the production of the acrylic copolymer. When the content is less than 90% by weight, the adhesive strength is not sufficient. When the content is more than 98% by weight, the cohesive strength may be lowered.
상기 히드록시기를 갖는 단량체는 이소시아네이트계 가교제의 이소시아네이트기와 반응하여 부분 가교 구조를 형성함으로써 승온 시 점착제의 응집 파괴가 일어나지 않도록 화학결합에 의한 응집력을 부여하는 성분이다.The monomer having a hydroxy group reacts with an isocyanate group of an isocyanate crosslinking agent to form a partially crosslinked structure, thereby giving a cohesive force by chemical bonding so that cohesive failure of the pressure-sensitive adhesive does not occur at a temperature rise.
히드록시기를 갖는 단량체로는 2-히드록시에틸(메타)아크릴레이트, 2-히드록시프로필(메타)아크릴레이트, 2-히드록시부틸(메타)아크릴레이트, 4-히드록시부틸(메타)아크릴레이트, 6-히드록시헥실(메타)아크릴레이트, 2-히드록시에틸렌글리콜(메타)아크릴레이트, 2-히드록시프로필렌글리콜(메타)아크릴레이트, 알킬렌기의 탄소수가 2-4인 히드록시알킬렌글리콜(메타)아크릴레이트 등을 들 수 있으며, 이들은 단독 또는 2종 이상 혼합하여 사용할 수 있다. Examples of the monomer having a hydroxy group include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl Hydroxypropyleneglycol (meth) acrylate, hydroxyalkylene glycol having 2 to 4 carbon atoms in the alkylene group (e.g., methoxyethyl (meth) acrylate, (Meth) acrylate, etc. These may be used alone or in combination of two or more.
히드록시기를 갖는 단량체는 아크릴계 공중합체의 제조에 사용되는 총 단량체 100중량%에 대하여 1.0 내지 5.0중량%로 포함되는 것이 바람직하다. 함량이 1.0중량% 미만인 경우 승온 시 응집 파괴가 일어나기 쉽고, 5.0중량% 초과인 경우 승온 시 유동 특성을 저하시킬 수 있다.
The monomer having a hydroxy group is preferably contained in an amount of 1.0 to 5.0% by weight based on 100% by weight of the total monomers used in the production of the acrylic copolymer. When the content is less than 1.0% by weight, cohesive failure tends to occur at the time of temperature rise, and when it is more than 5.0% by weight, flow characteristics at the time of temperature rise may be lowered.
본 발명의 일 실시형태에서, 상기 실란기를 갖는 단량체는 하기 화학식 1의 화합물을 포함한다.In one embodiment of the present invention, the monomer having a silane group includes a compound represented by the following formula (1).
[화학식 1][Chemical Formula 1]
상기 식에서,In this formula,
A는 C1-C10의 알킬렌기 또는 -(CH2)p-L-(CH2)q-이고,A is a C 1 -C 10 alkylene group or - (CH 2 ) p -L- (CH 2 ) q -
L은 -NHCOO-, NH 또는 O, 바람직하게는 -NHCOO-이며,L is -NHCOO-, NH or O, preferably -NHCOO-,
R1은 수소 또는 메틸이고, R < 1 > is hydrogen or methyl,
R2는 C1-C6의 알킬기 또는 C1-C6의 알콕시기, 바람직하게는 메틸, 메톡시 또는 에톡시이며,R 2 is a C 1 -C 6 alkyl group or a C 1 -C 6 alkoxy group, preferably methyl, methoxy or ethoxy,
p 및 q는 각각 독립적으로 1 내지 5의 정수이다.
p and q are each independently an integer of 1 to 5;
본 명세서에서 사용되는 C1-C10의 알킬렌기는 탄소수 1 내지 10개로 구성된 직쇄형 또는 분지형의 2가 탄화수소를 의미하며, 예를 들어 메틸렌, 에틸렌, 프로필렌, 부틸렌 등이 포함되나 이에 한정되는 것은 아니다.As used herein, the C 1 -C 10 alkylene group means a linear or branched divalent hydrocarbon having 1 to 10 carbon atoms, and includes, for example, methylene, ethylene, propylene, and butylene. It is not.
본 명세서에서 사용되는 C1-C6의 알킬기는 탄소수 1 내지 6개로 구성된 직쇄형 또는 분지형의 1가 탄화수소를 의미하며, 예를 들어 메틸, 에틸, n-프로필, i-프로필, n-부틸, n-펜틸, n-헥실 등이 포함되나 이에 한정되는 것은 아니다. As used herein, the C 1 -C 6 alkyl group means a linear or branched monovalent hydrocarbon having 1 to 6 carbon atoms, for example, methyl, ethyl, n-propyl, i-propyl, , n-pentyl, n-hexyl, and the like.
본 명세서에서 사용되는 C1-C6의 알콕시기는 탄소수 1 내지 6개로 구성된 직쇄형 또는 분지형 알콕시기를 의미하며, 메톡시, 에톡시, n-프로판옥시 등이 포함되나 이에 한정되는 것은 아니다.
As used herein, the C 1 -C 6 alkoxy group means a straight or branched alkoxy group having 1 to 6 carbon atoms, and includes, but is not limited to, methoxy, ethoxy, n-propaneoxy, and the like.
본 발명의 일 실시형태에서, 상기 실란기를 갖는 단량체는 하기 화학식 2 내지 5의 화합물로 구성된 군으로부터 선택된 1종 이상을 포함할 수 있다.In one embodiment of the present invention, the silane group-containing monomer may include at least one member selected from the group consisting of compounds represented by the following general formulas (2) to (5).
[화학식 2](2)
[화학식 3](3)
[화학식 4][Chemical Formula 4]
[화학식 5][Chemical Formula 5]
상기 실란기를 갖는 단량체는 아크릴계 공중합체의 제조에 사용되는 총 단량체 100중량%에 대하여 0.05 내지 5중량%로 포함되는 것이 바람직하다. 함량이 0.05중량% 미만인 경우 점착력 증가 효과가 미미하고, 5중량% 초과인 경우 리워크성이 저하될 수 있다.
The silane group-containing monomer is preferably contained in an amount of 0.05 to 5% by weight based on 100% by weight of the total monomers used in the production of the acrylic copolymer. When the content is less than 0.05% by weight, the adhesive strength increase effect is insignificant. When the content is more than 5% by weight, the workability may be deteriorated.
또한, 상기 단량체들 이외에 다른 중합성 단량체가 점착력을 저하시키지 않는 범위, 예컨대 10중량% 이하, 바람직하게는 5중량% 이하로 더 포함될 수 있다.
In addition, other polymerizable monomers other than the above-mentioned monomers may be further added in such a range as not to lower the adhesive force, for example, 10% by weight or less, preferably 5% by weight or less.
공중합체의 제조방법은 특별히 한정되지 않으며, 당해 분야에서 통상적으로 사용되는 괴상중합, 용액중합, 유화중합 또는 현탁중합 등의 방법을 이용하여 제조할 수 있으며, 용액중합이 바람직하다. 또한, 중합 시 통상 사용되는 용매, 중합개시제, 분자량 제어를 위한 연쇄이동제 등을 사용할 수 있다.
The method for producing the copolymer is not particularly limited and can be produced by a method such as bulk polymerization, solution polymerization, emulsion polymerization or suspension polymerization, which is commonly used in the art, and solution polymerization is preferable. In addition, a solvent, a polymerization initiator, a chain transfer agent for molecular weight control and the like which are usually used in polymerization can be used.
상기 아크릴계 공중합체는 겔투과크로마토그래피(Gel permeation chromatography, GPC)에 의해 측정된 중량평균분자량(폴리스티렌 환산)이 통상 50,000 내지 2,000,000이며, 바람직하게는 1,000,000 내지 2,000,000이다.
The acrylic copolymer generally has a weight average molecular weight (in terms of polystyrene) measured by Gel Permeation Chromatography (GPC) of usually 50,000 to 2,000,000, preferably 1,000,000 to 2,000,000.
본 발명의 일 실시형태에서, 상기 이소시아네이트계 가교제는 공중합체를 적절히 가교함으로써 점착제의 응집력을 강화하기 위한 성분으로서, 구체적으로 톨릴렌디이소시아네이트, 자일렌디이소시아네이트, 2,4-디페닐메탄디이소시아네트, 4,4-디페닐메탄디이소시아네트, 헥사메틸렌디이소시아네이트, 이소포론디이소시아네이트, 테트라메틸자일렌디이소시아네이트, 나프탈렌디이소시아네이트 등의 디이소시아네이트 화합물; 트리메틸올프로판 등의 다가 알콜계 화합물 1몰에 디이소시아네이트 화합물 3몰을 반응시킨 부가체, 디이소시아네이트 화합물 3몰을 자기 축합시킨 이소시아누레이트체, 디이소시아네이트 화합물 3몰 중 2몰로부터 얻어지는 디이소시아네이트 우레아에 나머지 1몰의 디이소시아네이트가 축합된 뷰렛체, 트리페닐메탄트리이소시아네이트, 메틸렌비스트리이소시아네이트 등의 3개의 관능기를 함유하는 다관능 이소시아네이트 화합물 등을 들 수 있으며, 이들은 단독 또는 2종 이상 혼합하여 사용할 수 있다. In one embodiment of the present invention, the isocyanate crosslinking agent is a component for reinforcing the cohesive force of the pressure-sensitive adhesive by appropriately crosslinking the copolymer, and specifically includes tolylene diisocyanate, xylylene diisocyanate, 2,4-diphenylmethane diisocyanate, Diisocyanate compounds such as 4,4-diphenylmethane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, tetramethyl xylene diisocyanate and naphthalene diisocyanate; An adduct obtained by reacting 3 moles of a diisocyanate compound with 1 mole of a polyhydric alcohol compound such as trimethylolpropane, an isocyanurate compound in which 3 moles of a diisocyanate compound is self-condensed, a diisocyanate obtained from 2 moles of 3 moles of a diisocyanate compound And multifunctional isocyanate compounds containing three functional groups such as burette, triphenylmethane triisocyanate and methylene bistriisocyanate in which the remaining one mole of diisocyanate is condensed with urea, and these may be used alone or in combination of two or more kinds. Can be used.
또한, 이소시아네이트계 가교제와 함께 헥사메틸올멜라민, 헥사메톡시메틸멜라민, 헥사부톡시메틸멜라민 등과 같은 멜라민계 화합물; 비스페놀 A와 에피클로로히드린의 축합체, 폴리옥시알킬렌폴리올의 폴리글리시딜에테르, 글리세린 디- 또는 트리글리시딜에테르, 테트라글리시딜자일렌디아민 등과 같은 에폭시계 화합물을 단독 또는 2종 이상 혼합하여 추가로 사용할 수 있다.In addition, a melamine-based compound such as hexamethylol melamine, hexamethoxymethyl melamine, hexabutoxymethyl melamine and the like together with an isocyanate-based cross-linking agent; Epoxy compounds such as condensates of bisphenol A and epichlorohydrin, polyglycidyl ether of polyoxyalkylene polyol, glycerin di- or triglycidyl ether, tetraglycidyl xylene diamine, etc., They can be used in combination.
상기 이소시아네이트계 가교제는 고형분 함량을 기준으로 상기 아크릴계 공중합체 100중량부에 대하여 0.1 내지 1.0중량부로 포함되는 것이 바람직하다. 함량이 0.1중량부 미만인 경우 부족한 가교도로 인해 응집력이 작아지게 되어 들뜸과 같은 내구성 저하가 유발되고 절단성을 해칠 수 있으며, 1.0중량부 초과인 경우 과다 가교반응에 의해 잔류응력 완화에 문제가 발생할 수 있다.
The isocyanate crosslinking agent is preferably contained in an amount of 0.1 to 1.0 part by weight based on 100 parts by weight of the acrylic copolymer based on the solid content. If the content is less than 0.1 part by weight, the cohesive force becomes small due to insufficient crosslinking, resulting in deterioration of durability such as lifting and deterioration of cutability. If the content is more than 1.0 part by weight, excessive crosslinking reaction may cause a problem of relaxation of residual stress have.
본 발명의 일 실시형태에서, 상기 에틸렌옥사이드기를 함유하는 (메타)아크릴레이트는 친수성으로 상온에서 접합되는 기재의 표면으로 이동하여 점착력을 조절함으로써 리워크성을 개선시킬 수 있는 성분으로서, 하기 화학식 6의 화합물을 포함할 수 있다.In one embodiment of the present invention, the (meth) acrylate containing the ethylene oxide group is a component capable of improving the reworkability by moving to a surface of a substrate which is hydrophilic and bonded at room temperature to control the adhesive force, ≪ / RTI >
[화학식 6][Chemical Formula 6]
상기 식에서,In this formula,
X는 수소 또는 메틸이고,X is hydrogen or methyl,
n은 5 내지 25의 정수이다.
n is an integer of 5 to 25;
상기 에틸렌옥사이드기를 함유하는 (메타)아크릴레이트는 고형분 함량을 기준으로 아크릴계 공중합체 100중량부에 대하여 0.1 내지 5.0중량부로 포함되는 것이 바람직하다. 함량이 0.1중량부 미만인 경우 리워크성 개선 효과가 미미하고, 5.0중량부 초과인 경우 내구성이 낮아질 수 있다.
The (meth) acrylate containing the ethylene oxide group is preferably contained in an amount of 0.1 to 5.0 parts by weight based on 100 parts by weight of the acrylic copolymer based on the solid content. When the content is less than 0.1 parts by weight, the effect of improving the workability is insignificant. When the content is more than 5.0 parts by weight, the durability may be lowered.
본 발명의 일 실시형태에 따른 점착제 조성물은 상기와 같은 성분 이외에, 용도에 따라 요구되는 점착력, 응집력, 점성, 탄성률, 유리전이온도, 대전방지성 등을 조절하기 위하여, 점착성 부여 수지, 산화방지제, 부식방지제, 레벨링제, 표면윤활제, 염료, 안료, 소포제, 충전제, 광안정제, 대전방지제 등의 첨가제를 더 포함할 수 있다.
The pressure-sensitive adhesive composition according to one embodiment of the present invention may further contain additives such as a tackifier resin, antioxidant, antistatic agent, antistatic agent, antioxidant, antistatic agent, An antioxidant, a corrosion inhibitor, a leveling agent, a surface lubricant, a dye, a pigment, a defoaming agent, a filler, a light stabilizer, an antistatic agent and the like.
본 발명의 점착제 조성물은 액정셀과의 접합을 위한 편광판용 점착제뿐만 아니라 표면보호필름용 점착제로서도 사용할 수 있다. 또한, 보호필름, 반사시트, 구조용 점착시트, 사진용 점착시트, 차선표시용 점착시트, 광학용 점착제품, 전자부품용 점착제뿐만 아니라 일반 상업용 점착시트제품, 의료용 패치로도 사용 가능하다.
The pressure-sensitive adhesive composition of the present invention can be used not only as a pressure-sensitive adhesive for a polarizing plate for bonding with a liquid crystal cell but also as a pressure-sensitive adhesive for a surface protective film. In addition, it can be used not only 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 electronic component adhesive, but also a general commercial adhesive sheet product or a medical patch.
본 발명의 일 실시형태는 상기 점착제 조성물로 이루어진 점착제층이 적층된 편광판에 관한 것이다. One embodiment of the present invention relates to a polarizing plate in which a pressure-sensitive adhesive layer composed of the pressure-sensitive adhesive composition is laminated.
상기 점착제층의 두께는 그 점착력에 따라 조절될 수 있으며, 통상 3 내지 100㎛인 것이 바람직하며, 10 내지 100㎛인 것이 보다 바람직하다.
The thickness of the pressure-sensitive adhesive layer can be adjusted according to the adhesive force, and is preferably 3 to 100 탆, more preferably 10 to 100 탆.
이러한 편광판은 통상의 액정표시장치에 모두 적용 가능하며, 구체적으로 상기 점착제층이 적층된 편광판을 액정셀의 적어도 한 면에 접합한 액정패널을 포함하는 액정표시장치를 구성할 수 있다.Such a polarizing plate can be applied to all ordinary liquid crystal display devices, and concretely, a liquid crystal display device including a liquid crystal panel in which a polarizing plate in which the pressure-sensitive adhesive layer is laminated is bonded to at least one surface of a liquid crystal cell can be constituted.
따라서, 본 발명의 일 실시형태는 액정셀의 적어도 한 면에 상기 편광판이 구비된 액정표시장치에 관한 것이다.
Therefore, one embodiment of the present invention relates to a liquid crystal display device provided with the polarizing plate on at least one surface of a liquid crystal cell.
이하, 실시예, 비교예 및 실험예에 의해 본 발명을 보다 구체적으로 설명하고자 한다. 이들 실시예, 비교예 및 실험예는 오직 본 발명을 설명하기 위한 것으로, 본 발명의 범위가 이들에 국한되지 않는다는 것은 당업자에게 있어서 자명하다.
Hereinafter, the present invention will be described more specifically with reference to Examples, Comparative Examples and Experimental Examples. It should be apparent to those skilled in the art that these examples, comparative examples and experimental examples are only for illustrating the present invention, and the scope of the present invention is not limited thereto.
제조예 1: 아크릴계 공중합체의 제조Production Example 1: Preparation of acrylic copolymer
질소가스가 환류되고 온도조절이 용이하도록 냉각장치를 설치한 1L의 반응기에 n-부틸아크릴레이트(BA) 86중량부, 에틸헥실아크릴레이트(EHA) 10중량부, 2-히드록시에틸아크릴레이트(2-HEA) 3중량부, 3-(트리메톡시실릴)프로필아크릴레이트(KBM-5130) 1중량부로 이루어진 단량체 혼합물을 투입한 후, 용제로 에틸아세테이트(EAc) 100중량부를 투입하였다. 그 다음 산소를 제거하기 위하여 질소가스를 1시간 동안 퍼징한 후, 80℃로 유지하였다. 상기 혼합물을 균일하게 혼합한 후, 반응개시제로 아조비스이소부티로니트릴(AIBN) 0.07중량부를 투입하고, 8시간 동안 반응시켜 아크릴계 공중합체(중량평균분자량 약 130만)를 제조하였다.
(BA), 10 parts by weight of ethylhexyl acrylate (EHA), and 2 parts by weight of 2-hydroxyethyl acrylate (manufactured by Nippon Aerosil Co., Ltd.) were added to a 1 L reactor equipped with a cooling device, , And 3 parts by weight of 3- (trimethoxysilyl) propyl acrylate (KBM-5130), and 100 parts by weight of ethyl acetate (EAc) was added as a solvent. Nitrogen gas was then purged for 1 hour to remove oxygen and then maintained at 80 ° C. After the mixture was homogeneously mixed, 0.07 part by weight of azobisisobutyronitrile (AIBN) was added as a reaction initiator and reacted for 8 hours to prepare an acrylic copolymer (weight average molecular weight: about 1.3 million).
제조예 2 내지 9: 아크릴계 공중합체의 제조Production Examples 2 to 9: Preparation of acrylic copolymer
상기 제조예 1과 동일하게 실시하되, 하기 표 1의 조성으로 아크릴계 공중합체를 제조하였다(단위: 중량부).An acrylic copolymer was prepared in the same manner as in Preparation Example 1 except that the composition of the following Table 1 was used (unit: parts by weight).
갖는 단량체Crosslinkable functional group
The monomer
(mgKOH/g)Acid value
(mgKOH / g)
5130KBM-
5130
502KBM-
502
503KBE-
503
6480SIM-
6480
BA: 부틸아크릴레이트BA: butyl acrylate
EHA: 에틸헥실아크릴레이트EHA: Ethylhexyl acrylate
DA: 도데실아크릴레이트DA: Dodecyl acrylate
MA: 메틸아크릴레이트MA: methyl acrylate
2-HEA: 2-히드록시에틸아크릴레이트2-HEA: 2-hydroxyethyl acrylate
4-HBA: 4-히드록시부틸아크릴레이트4-HBA: 4-hydroxybutyl acrylate
AA: 아크릴산AA: Acrylic acid
KBM-5130: 화학식 2의 화합물KBM-5130: Compound of formula 2
KBM-502: 화학식 3의 화합물KBM-502: Compound of formula 3
KBE-503: 화학식 4의 화합물KBE-503: Compound of Formula 4
SIM-6480: 화학식 5의 화합물
SIM-6480: Compound of Formula 5
실시예 1 내지 15 및 비교예 1 내지 2: 점착제 부착 편광판의 제조Examples 1 to 15 and Comparative Examples 1 to 2: Production of polarizer with adhesive
(1) 점착제 조성물의 제조(1) Production of pressure-sensitive adhesive composition
상기 제조예에서 수득한 아크릴계 공중합체, 가교제 및 에틸렌옥사이드기를 함유하는 (메타)아크릴레이트를 하기 표 2의 조성으로 혼합한 후(단위: 중량부), 28중량%의 농도로 희석하여 점착제 조성물을 제조하였다.(Meth) acrylate containing the acrylic copolymer, crosslinking agent and ethylene oxide group obtained in the above Production Example were mixed in the composition shown in the following Table 2 (unit: part by weight) and diluted to a concentration of 28% by weight to prepare a pressure- .
공중합체
(100중량부)Acrylic
Copolymer
(100 parts by weight)
(메타)아크릴레이트 Containing an ethylene oxide group
(Meth) acrylate
A-1: 코로네이트-L (TDI의 TMP 어덕트, 일본우레탄사)A-1: Coronate-L (TMP adduct of TDI, Urethane Co., Japan)
A-2: VESTANAT T 1890 (IPDI의 삼량체, 에보닉사)A-2: VESTANAT T 1890 (trimer of IPDI, Evonix)
A-3: D110N (XDI의 어덕트, 미쯔이화학사)A-3: D110N (an adduct of XDI, Mitsui Chemical)
A-4: 코로네이트-HXR (HDI의 이소아누레이트, 일본우레탄사)A-4: Coronate-HXR (isocyanurate of HDI, Urethane Company of Japan)
AM90G: 메톡시폴리에틸렌글리콜아크릴레이트(EO 9.0mol) (신나까무라화학사)AM90G: methoxypolyethylene glycol acrylate (EO 9.0mol) (Shin Nakamura Chemical Co., Ltd.)
M130G: 메톡시폴리에틸렌글리콜메타아크릴레이트(EO 13mol), (신나까무라화학사)M130G: methoxypolyethylene glycol methacrylate (EO 13 mol), (Shin Nakamura Chemical)
M230G: 메톡시폴리에틸렌글리콜메타아크릴레이트(EO 23mol), (신나까무라화학사)
M230G: methoxypolyethylene glycol methacrylate (EO 23 mol), (Shin Nakamura Chemical Co.)
(2) 점착제 부착 편광판의 제조 (2) Production of Polarizer with Adhesive
제조된 점착제 조성물을 실리콘 이형제가 코팅된 이형필름 상에 두께가 20㎛가 되도록 도포하고 100℃에서 1분 동안 건조시켜 점착제층을 형성하였다. 두께 185㎛의 요오드계 편광판에 상기 제조된 점착제층을 점착 가공으로 적층하여 점착제 부착 편광판을 제조하였다. 제조된 편광판을 23℃, 60%RH의 조건 하에서 양생 기간 동안 보관하였다.
The pressure-sensitive adhesive composition thus prepared was coated on a release film coated with a silicone release agent to a thickness of 20 탆 and dried at 100 캜 for 1 minute to form a pressure-sensitive adhesive layer. The pressure-sensitive adhesive layer prepared above was laminated to an iodine-based polarizing plate having a thickness of 185 μm by a pressure-sensitive adhesive process to produce a polarizer with a pressure-sensitive adhesive. The prepared polarizing plate was stored for a curing period under the conditions of 23 캜 and 60% RH.
실험예 1: 점착력, 내구성, 리워크성 및 ITO 부식성 평가Experimental Example 1: Evaluation of adhesion, durability, reworkability and ITO corrosion resistance
상기 실시예 및 비교예에서 제조된 점착제 부착 편광판의 물성을 하기의 방법으로 측정하고, 그 결과를 하기 표 3에 나타내었다.
The physical properties of the polarizer with a pressure-sensitive adhesive prepared in the above Examples and Comparative Examples were measured by the following methods, and the results are shown in Table 3 below.
(1) 점착력(N/25㎜)(1) Adhesive force (N / 25 mm)
점착제 부착 편광판을 25㎜×100㎜의 크기로 절단하고 이형필름을 박리한 후, 유리기판(#1737, 코닝사)에 0.25MPa의 압력으로 라미네이션하고 오토클레이브 처리하여 시편을 제작하였다. The polarizing plate with a pressure-sensitive adhesive was cut to a size of 25 mm x 100 mm, the release film was peeled off, and the glass substrate (# 1737, Corning) was laminated at a pressure of 0.25 MPa and autoclaved to prepare a specimen.
초기 점착력은 23℃, 50%RH의 조건 하에서 24시간 방치한 후의 시편, 가온 점착력은 시편을 50℃, 50%RH의 조건 하에서 48시간 방치한 후의 시편을 각각 만능인장시험기(UTM, Instron)를 사용하여 박리 속도 300mm/분, 박리각도 180°로 점착제층을 박리하여 측정하였다. 이때, 측정은 23℃, 50%RH의 조건 하에서 실시하였다.
The initial adhesive strength of the specimens after being left for 24 hours under conditions of 23 ° C and 50% RH, and the temperature bonding strength of the specimens after 48 hours of storage at 50 ° C and 50% RH were measured using a universal tensile tester (UTM, Instron) Sensitive adhesive layer was peeled off at a peeling speed of 300 mm / min and a peeling angle of 180 deg. At this time, measurement was carried out under conditions of 23 캜 and 50% RH.
(2) 내구성(내열, 내습열)(2) Durability (heat, moisture and heat)
점착제 부착 편광판을 90㎜×170㎜의 크기로 절단하고 이형필름을 박리한 후, 유리기판(110㎜×190㎜×0.7㎜)의 양면에 광학 흡수축이 직교하도록 부착하여 시편을 제작하였다. 이때, 가해진 압력은 5kg/cm2이며, 기포나 이물이 생기지 않도록 크린룸 작업을 하였다. The polarizing plate with a pressure-sensitive adhesive was cut into a size of 90 mm x 170 mm, the release film was peeled off, and the optical absorption axis was perpendicularly attached to both surfaces of a glass substrate (110 mm x 190 mm x 0.7 mm). At this time, the applied pressure was 5 kg / cm 2 , and a clean room operation was performed so that bubbles or foreign matter would not be generated.
제작된 시편의 내열 특성은 90℃의 온도에서 1000시간 동안 방치한 후에 기포나 박리의 발생 여부를 관찰하였고, 내습열 특성은 70℃의 온도 및 90%RH의 조건 하에서 1000시간 방치한 후에 기포나 박리의 발생 여부를 관찰하였다. 이때, 시편의 상태를 평가하기 직전에 상온에서 24시간 방치한 후 관찰하였다. The heat resistance of the fabricated specimens was measured for the presence of bubbles or exfoliation after being left at a temperature of 90 ° C. for 1000 hours. The moisture resistance of the specimens was measured at a temperature of 70 ° C. and a relative humidity of 90% The occurrence of peeling was observed. At this time, the sample was allowed to stand at room temperature for 24 hours immediately before evaluating the state of the specimen.
<평가기준><Evaluation Criteria>
ⓞ: 기포나 박리 없음Ⓞ: No bubble or peeling
○: 기포나 박리 < 5개○: Bubbles or peeling <5
△: 5개 ≤ 기포나 박리 < 10개?: 5 pieces? Bubbles or peeling <10 pieces
×: 10개 ≤ 기포나 박리
X: 10 pieces < bubble &
(3) 리워크성 (3) Re-workability
점착제 부착 편광판을 폭 25㎜, 길이 100㎜의 크기로 잘라내고 이형필름을 박리한 후, 유리기판(#1737, 코닝사)에 0.25MPa의 압력으로 라미네이션하고 5기압, 50℃의 조건으로 20분 동안 오토클레이브 처리하여 시편을 제작하였다. 내열 조건인 80℃ 오븐에 넣은 후 10시간 뒤에 꺼내어 120시간 동안 상온에서 방치한 후 1.3㎝/s의 속도로 박리하였다. The polarizing plate with a pressure-sensitive adhesive was cut to a size of 25 mm in width and 100 mm in length, and the release film was peeled off. The glass plate (# 1737, Corning) was laminated at a pressure of 0.25 MPa under conditions of 5 atm and 50 캜 for 20 minutes The sample was autoclaved. After putting it in an oven at 80 ° C, which was a heat-resistant condition, it was taken out after 10 hours, left at room temperature for 120 hours, and peeled at a rate of 1.3 cm / s.
<평가기준><Evaluation Criteria>
○: 유리기판에 점착제의 남음이 없고 편광판의 찢어짐 없이 깨끗이 박리됨○: There is no adhesive residue on the glass substrate and the glass substrate is cleanly peeled off without tearing the polarizer
×: 유리기판에 점착제가 남아있거나 박리과정에서 편광판이 찢어짐
X: The pressure-sensitive adhesive was left on the glass substrate or the polarizer was torn in the peeling process
(4) ITO 부식성(4) ITO corrosion
점착제 부착 편광판을 40㎜×40㎜의 크기로 절단하고 이형필름을 박리한 후 ITO 필름에 접합한 다음, 60℃·95%RH의 조건 하에 1000시간 방치하였다. 그리고, ITO막 대각선상 2점의 모서리 사이의 전기 저항 값을 「SK-300」(카이세)을 이용하여 측정하였다. ITO 막의 초기 전기 저항 값은 800Ω 이상 1,000Ω 미만이었다.The polarizing plate with a pressure-sensitive adhesive was cut into a size of 40 mm x 40 mm, and the release film was peeled off and bonded to the ITO film, and then left for 1000 hours under conditions of 60 ° C and 95% RH. Then, the electric resistance value between the corners of the two points on the diagonal line of the ITO film was measured using " SK-300 " (Kaiser). The initial electrical resistance value of the ITO film was 800? And less than 1,000 ?.
<평가기준><Evaluation Criteria>
○: ITO 전기 저항 값이 800Ω 이상 1,500Ω 미만 ○: ITO electric resistance value is 800Ω or more and less than 1,500Ω
△: ITO 전기 저항 값이 1,500Ω 이상 2,000Ω 미만△: ITO electric resistance value is 1,500 Ω or more and less than 2,000 Ω
×: ITO 전기 저항 값이 2,000Ω 이상
×: ITO electric resistance value of 2,000Ω or more
부식성ITO
causticity
(90℃)Heat resistance
(90 DEG C)
(70℃, 90%RH)Wet heat
(70 < 0 > C, 90% RH)
상기 표 3에서 보듯이, 본 발명에 따른 실시예 1 내지 15의 점착제 조성물로 이루어진 점착제층이 적층된 편광판은 실란기를 갖는 단량체를 포함하지 않은 비교예 1의 점착제 조성물로 이루어진 점착제층이 적층된 편광판에 비해 점착력과 내열 및 내습열 내구성이 우수하고, 산가가 1.5㎎KOH/g인 아크릴계 공중합체를 포함하는 비교예 2의 점착제 조성물로 이루어진 점착제층이 적층된 편광판에 비해 금속 산화물 부식성이 낮으며, 에틸렌옥사이드기를 함유하는 (메타)아크릴레이트를 포함하지 않은 비교예 3의 점착제 조성물로 이루어진 점착제층이 적층된 편광판에 비해 리워크성이 우수하였다.
As shown in Table 3, the polarizer plate in which the pressure-sensitive adhesive composition layers of the pressure-sensitive adhesive compositions of Examples 1 to 15 according to the present invention were laminated was composed of the polarizer plate in which the pressure-sensitive adhesive layer composition of Comparative Example 1 containing no silane- , The metal oxide corrosion resistance is lower than that of the polarizing plate in which the pressure-sensitive adhesive layer composed of the pressure-sensitive adhesive composition of Comparative Example 2 including an acrylic copolymer having an excellent adhesive strength, heat resistance and anti-wet heat durability and an acrylic copolymer having an acid value of 1.5 mgKOH / Sensitive adhesive layer of Comparative Example 3 containing no (meth) acrylate containing an ethylene oxide group was superior to the polarizing plate in which the pressure-sensitive adhesive layer was laminated.
이상으로 본 발명의 특정한 부분을 상세히 기술하였는 바, 본 발명이 속한 기술분야에서 통상의 지식을 가진 자에게 있어서 이러한 구체적인 기술은 단지 바람직한 구현예일 뿐이며, 이에 본 발명의 범위가 제한되는 것이 아님은 명백하다. 본 발명이 속한 기술분야에서 통상의 지식을 가진 자라면 상기 내용을 바탕으로 본 발명의 범주 내에서 다양한 응용 및 변형을 행하는 것이 가능할 것이다.It will be apparent to those skilled in the art that various modifications and variations can be made in the present invention without departing from the spirit or scope of the invention. Do. It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims.
따라서, 본 발명의 실질적인 범위는 첨부된 특허청구범위와 그의 등가물에 의하여 정의된다고 할 것이다.Accordingly, the actual scope of the invention is defined by the appended claims and their equivalents.
Claims (10)
[화학식 1]
상기 식에서,
A는 C1-C10의 알킬렌기 또는 -(CH2)p-L-(CH2)q-이고,
L은 -NHCOO-, NH 또는 O이며,
R1은 수소 또는 메틸이고,
R2는 C1-C6의 알킬기 또는 C1-C6의 알콕시기이며,
p 및 q는 각각 독립적으로 1 내지 5의 정수이다.The pressure-sensitive adhesive composition according to claim 2, wherein the monomer having a silane group comprises a compound represented by the following formula (1):
[Chemical Formula 1]
In this formula,
A is a C 1 -C 10 alkylene group or - (CH 2 ) p -L- (CH 2 ) q -
L is -NHCOO-, NH or O,
R < 1 > is hydrogen or methyl,
R 2 is a C 1 -C 6 alkyl group or a C 1 -C 6 alkoxy group,
p and q are each independently an integer of 1 to 5;
A는 C1-C10의 알킬렌기 또는 -(CH2)p-L-(CH2)q-이고,
L은 -NHCOO-이며,
R1은 수소 또는 메틸이고,
R2는 메틸, 메톡시 또는 에톡시이며,
p 및 q는 각각 독립적으로 1 내지 5의 정수인 점착제 조성물.The method of claim 3,
A is a C 1 -C 10 alkylene group or - (CH 2 ) p -L- (CH 2 ) q -
L is -NHCOO-,
R < 1 > is hydrogen or methyl,
R < 2 > is methyl, methoxy or ethoxy,
p and q are each independently an integer of 1 to 5;
[화학식 2]
[화학식 3]
[화학식 4]
[화학식 5]
(2)
(3)
[Chemical Formula 4]
[Chemical Formula 5]
[화학식 6]
상기 식에서,
X는 수소 또는 메틸이고,
n은 5 내지 25의 정수이다.The pressure-sensitive adhesive composition according to claim 1, wherein the (meth) acrylate containing an ethylene oxide group comprises a compound of the following formula (6):
[Chemical Formula 6]
In this formula,
X is hydrogen or methyl,
n is an integer of 5 to 25;
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018052178A1 (en) * | 2016-09-13 | 2018-03-22 | 동우 화인켐 주식회사 | Optically clear adhesive composition, optically clear adhesive film comprising same, and flat display device |
| KR20230081394A (en) * | 2021-11-30 | 2023-06-07 | 한국생산기술연구원 | Adhesive materials and their use |
| KR20230081423A (en) * | 2021-11-30 | 2023-06-07 | 한국생산기술연구원 | Adhesive materials and their use |
| US11760866B2 (en) | 2017-08-16 | 2023-09-19 | Lg Chem, Ltd. | White pigment comprising ZIF-based powder, polymer resin film and method for changing color of medium using white pigment |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08104855A (en) | 1994-10-03 | 1996-04-23 | Soken Chem & Eng Co Ltd | Liquid crystal element and pressure-sensitive adhesive composition therefor |
-
2015
- 2015-02-06 KR KR1020150018694A patent/KR20160096958A/en not_active Application Discontinuation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08104855A (en) | 1994-10-03 | 1996-04-23 | Soken Chem & Eng Co Ltd | Liquid crystal element and pressure-sensitive adhesive composition therefor |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018052178A1 (en) * | 2016-09-13 | 2018-03-22 | 동우 화인켐 주식회사 | Optically clear adhesive composition, optically clear adhesive film comprising same, and flat display device |
| US11760866B2 (en) | 2017-08-16 | 2023-09-19 | Lg Chem, Ltd. | White pigment comprising ZIF-based powder, polymer resin film and method for changing color of medium using white pigment |
| KR20230081394A (en) * | 2021-11-30 | 2023-06-07 | 한국생산기술연구원 | Adhesive materials and their use |
| KR20230081423A (en) * | 2021-11-30 | 2023-06-07 | 한국생산기술연구원 | Adhesive materials and their use |
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