KR101260095B1 - Pressure-sensitive adhesive composition, pressure-sensitive adhesive film, polarizer and liquid crystal display - Google Patents
Pressure-sensitive adhesive composition, pressure-sensitive adhesive film, polarizer and liquid crystal display Download PDFInfo
- Publication number
- KR101260095B1 KR101260095B1 KR1020090013426A KR20090013426A KR101260095B1 KR 101260095 B1 KR101260095 B1 KR 101260095B1 KR 1020090013426 A KR1020090013426 A KR 1020090013426A KR 20090013426 A KR20090013426 A KR 20090013426A KR 101260095 B1 KR101260095 B1 KR 101260095B1
- Authority
- KR
- South Korea
- Prior art keywords
- sensitive adhesive
- pressure
- compound
- adhesive composition
- film
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000004820 Pressure-sensitive adhesive Substances 0.000 title claims abstract description 58
- 239000000203 mixture Substances 0.000 title claims abstract description 47
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- 230000005855 radiation Effects 0.000 claims abstract description 51
- 229920005989 resin Polymers 0.000 claims abstract description 23
- 239000011347 resin Substances 0.000 claims abstract description 23
- 239000002313 adhesive film Substances 0.000 claims abstract description 20
- 230000001070 adhesive effect Effects 0.000 claims abstract description 19
- 239000000853 adhesive Substances 0.000 claims abstract description 16
- -1 2-isocyanatoethyl Chemical group 0.000 claims description 72
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 62
- 239000002585 base Substances 0.000 claims description 31
- 125000000524 functional group Chemical group 0.000 claims description 26
- 239000000178 monomer Substances 0.000 claims description 25
- 125000004429 atom Chemical group 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000002184 metal Substances 0.000 claims description 13
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 12
- 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 claims description 12
- 239000010410 layer Substances 0.000 claims description 12
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 8
- 150000002009 diols Chemical class 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 7
- 229920001577 copolymer Polymers 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 6
- 239000004698 Polyethylene Substances 0.000 claims description 5
- 125000003700 epoxy group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 229920000573 polyethylene Polymers 0.000 claims description 5
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical group C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- QASBHTCRFDZQAM-UHFFFAOYSA-N (2-isocyanato-2-methyl-3-prop-2-enoyloxypropyl) prop-2-enoate Chemical compound C=CC(=O)OCC(C)(COC(=O)C=C)N=C=O QASBHTCRFDZQAM-UHFFFAOYSA-N 0.000 claims description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 claims description 3
- DPNXHTDWGGVXID-UHFFFAOYSA-N 2-isocyanatoethyl prop-2-enoate Chemical compound C=CC(=O)OCCN=C=O DPNXHTDWGGVXID-UHFFFAOYSA-N 0.000 claims description 3
- JEHFRMABGJJCPF-UHFFFAOYSA-N 2-methylprop-2-enoyl isocyanate Chemical compound CC(=C)C(=O)N=C=O JEHFRMABGJJCPF-UHFFFAOYSA-N 0.000 claims description 3
- 239000004743 Polypropylene Substances 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical compound C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 claims description 3
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 claims description 3
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229920006267 polyester film Polymers 0.000 claims description 3
- 229920001155 polypropylene Polymers 0.000 claims description 3
- RLUFBDIRFJGKLY-UHFFFAOYSA-N (2,3-dichlorophenyl)-phenylmethanone Chemical compound ClC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1Cl RLUFBDIRFJGKLY-UHFFFAOYSA-N 0.000 claims description 2
- XKSUVRWJZCEYQQ-UHFFFAOYSA-N 1,1-dimethoxyethylbenzene Chemical compound COC(C)(OC)C1=CC=CC=C1 XKSUVRWJZCEYQQ-UHFFFAOYSA-N 0.000 claims description 2
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 claims description 2
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 claims description 2
- GIMQKKFOOYOQGB-UHFFFAOYSA-N 2,2-diethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)(OCC)C(=O)C1=CC=CC=C1 GIMQKKFOOYOQGB-UHFFFAOYSA-N 0.000 claims description 2
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 claims description 2
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 claims description 2
- LCHAFMWSFCONOO-UHFFFAOYSA-N 2,4-dimethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC(C)=C3SC2=C1 LCHAFMWSFCONOO-UHFFFAOYSA-N 0.000 claims description 2
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 claims description 2
- DZZAHLOABNWIFA-UHFFFAOYSA-N 2-butoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCCCC)C(=O)C1=CC=CC=C1 DZZAHLOABNWIFA-UHFFFAOYSA-N 0.000 claims description 2
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 claims description 2
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 claims description 2
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 claims description 2
- YJQMXVDKXSQCDI-UHFFFAOYSA-N 2-ethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3SC2=C1 YJQMXVDKXSQCDI-UHFFFAOYSA-N 0.000 claims description 2
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 claims description 2
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 claims description 2
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 claims description 2
- MYISVPVWAQRUTL-UHFFFAOYSA-N 2-methylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3SC2=C1 MYISVPVWAQRUTL-UHFFFAOYSA-N 0.000 claims description 2
- YTPSFXZMJKMUJE-UHFFFAOYSA-N 2-tert-butylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(C(C)(C)C)=CC=C3C(=O)C2=C1 YTPSFXZMJKMUJE-UHFFFAOYSA-N 0.000 claims description 2
- 239000005062 Polybutadiene Substances 0.000 claims description 2
- 244000028419 Styrax benzoin Species 0.000 claims description 2
- 235000000126 Styrax benzoin Nutrition 0.000 claims description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 claims description 2
- 229960002130 benzoin Drugs 0.000 claims description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- 239000012965 benzophenone Substances 0.000 claims description 2
- QDVNNDYBCWZVTI-UHFFFAOYSA-N bis[4-(ethylamino)phenyl]methanone Chemical compound C1=CC(NCC)=CC=C1C(=O)C1=CC=C(NCC)C=C1 QDVNNDYBCWZVTI-UHFFFAOYSA-N 0.000 claims description 2
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 claims description 2
- 235000019382 gum benzoic Nutrition 0.000 claims description 2
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 claims description 2
- 229920002857 polybutadiene Polymers 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- 229920001721 polyimide Polymers 0.000 claims description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 2
- 239000005046 Chlorosilane Substances 0.000 claims 2
- 230000005494 condensation Effects 0.000 claims 2
- 238000009833 condensation Methods 0.000 claims 2
- YDIYEOMDOWUDTJ-UHFFFAOYSA-N 4-(dimethylamino)benzoic acid Chemical class CN(C)C1=CC=C(C(O)=O)C=C1 YDIYEOMDOWUDTJ-UHFFFAOYSA-N 0.000 claims 1
- 229920001083 polybutene Polymers 0.000 claims 1
- 230000001681 protective effect Effects 0.000 abstract description 19
- 238000000034 method Methods 0.000 abstract description 16
- 230000006866 deterioration Effects 0.000 abstract description 3
- 239000000654 additive Substances 0.000 abstract description 2
- 230000000996 additive effect Effects 0.000 abstract 1
- 230000007704 transition Effects 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
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- 229920006243 acrylic copolymer Polymers 0.000 description 13
- 230000003287 optical effect Effects 0.000 description 12
- 230000000704 physical effect Effects 0.000 description 11
- 238000001723 curing Methods 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 239000012790 adhesive layer Substances 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 239000002216 antistatic agent Substances 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 229940117969 neopentyl glycol Drugs 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
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- 239000004094 surface-active agent Substances 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 230000005611 electricity Effects 0.000 description 4
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 230000003068 static effect Effects 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
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- 239000002253 acid Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
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- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
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- 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 2
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Classifications
-
- E—FIXED CONSTRUCTIONS
- E03—WATER SUPPLY; SEWERAGE
- E03F—SEWERS; CESSPOOLS
- E03F5/00—Sewerage structures
- E03F5/04—Gullies inlets, road sinks, floor drains with or without odour seals or sediment traps
- E03F5/0401—Gullies for use in roads or pavements
- E03F5/0405—Gullies for use in roads or pavements with an odour seal
-
- E—FIXED CONSTRUCTIONS
- E03—WATER SUPPLY; SEWERAGE
- E03F—SEWERS; CESSPOOLS
- E03F5/00—Sewerage structures
- E03F5/04—Gullies inlets, road sinks, floor drains with or without odour seals or sediment traps
- E03F5/041—Accessories therefor
-
- E—FIXED CONSTRUCTIONS
- E03—WATER SUPPLY; SEWERAGE
- E03F—SEWERS; CESSPOOLS
- E03F5/00—Sewerage structures
- E03F5/04—Gullies inlets, road sinks, floor drains with or without odour seals or sediment traps
- E03F2005/0416—Gullies inlets, road sinks, floor drains with or without odour seals or sediment traps with an odour seal
- E03F2005/0417—Gullies inlets, road sinks, floor drains with or without odour seals or sediment traps with an odour seal in the form of a valve
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Hydrology & Water Resources (AREA)
- Public Health (AREA)
- Water Supply & Treatment (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
본 발명은, 방사선 중합성기를 함유하는 베이스 수지 및 방사선 중합성기를 함유하는 대전방지성 화합물을 포함하는 점착제 조성물, 상기를 포함하는 점착 필름, 편광판 및 액정표시장치에 관한 것이다. 본 발명에서는 대전방지성 화합물을 소량 사용하면서도 우수한 대전방지 성능의 구현이 가능하고, 또한 첨가제의 이행 현상에 의한 경시적인 점착 물성의 저하를 억제할 수 있는 점착제 조성물이 제공된다. 이에 따라 본 발명의 점착제 조성물은, 예를 들면 편광판용 표면보호필름에 적용되어, 액정표시장치의 대형화 및 공정의 고속화 요구에 효과적으로 부응할 수 있다. This invention relates to the adhesive composition containing the base resin containing a radiation polymerizable group, and the antistatic compound containing a radiation polymerizable group, the adhesive film containing the above, a polarizing plate, and a liquid crystal display device. The present invention provides a pressure-sensitive adhesive composition capable of realizing excellent antistatic performance while using a small amount of the antistatic compound, and also capable of suppressing the deterioration of the adhesive properties over time due to the transition phenomenon of the additive. Accordingly, the pressure-sensitive adhesive composition of the present invention can be applied to, for example, a surface protective film for a polarizing plate, which can effectively meet the demands of increasing the size of the liquid crystal display device and speeding up the process.
점착제 조성물, 보호필름, 편광판, 액정표시장치, 방사선 중합성기, 대전방지성 화합물 Adhesive composition, protective film, polarizing plate, liquid crystal display device, radiation polymerizable group, antistatic compound
Description
본 발명은 점착제 조성물, 상기의 경화물을 포함하는 점착 필름, 편광판 및 액정표시장치에 관한 것이다.The present invention relates to an adhesive composition, an adhesive film containing the cured product, a polarizing plate, and a liquid crystal display device.
광학 부품이나 전자 부품의 수송이나 프린트 기판으로의 실장에 있어서는, 개개의 부품을 소정의 필름으로 포장한 상태나 점착 테이프를 부착한 상태로 이송하는 경우가 많이 있다. 그 중, 표면보호필름은 광학, 전자 부품 분야에서 특히 널리 사용되고 있다.In transporting an optical component, an electronic component, or mounting to a printed board, there are many cases where individual components are packaged in a predetermined film or in a state in which an adhesive tape is attached. Among them, surface protection films are particularly widely used in the field of optical and electronic components.
표면보호필름은 일반적으로 보호 필름측에 도포된 점착제층을 통해 피보호체에 접합하여, 피보호체의 가공, 반송 시에 생기는 상처나 오염을 방지할 목적으로 사용된다. 예를 들면, 액정표시장치에 사용되는 편광판이나 파장판 등의 광학부재는 표면보호필름이 광학부재에 점착제층을 통해 접합되어 있다. 이 표면보호필름 은 불필요하게 된 단계에서 박리되어 제거된다.A surface protective film is generally used for the purpose of bonding to a to-be-protected body through the adhesive layer apply | coated on the protective film side, and preventing the wound and the contamination which arises at the time of processing and conveyance of a to-be-protected body. For example, in an optical member such as a polarizing plate or a wavelength plate used in a liquid crystal display device, a surface protective film is bonded to the optical member through an adhesive layer. This surface protective film is peeled off and removed in an unnecessary step.
일반적으로 표면보호필름이나 광학부재는 플라스틱 재료로 되어 있기 때문에, 전기 절연성이 높아 마찰이나 박리 시에 정전기를 발생한다. 따라서, 보호 필름을 편광판 등의 광학부재로부터 박리할 때에도 정전기가 발생하게 되는데, 이 때 정전기가 잔존하는 채로 액정에 전압을 인가하면, 액정 분자의 배향이 손실되고, 또한 패널 결손 등이 생기는 문제점이 있다.In general, since the surface protection film and the optical member are made of a plastic material, the electrical insulating property is high, and static electricity is generated during friction and peeling. Accordingly, static electricity is generated even when the protective film is peeled off from an optical member such as a polarizing plate. If voltage is applied to the liquid crystal while the static electricity remains, the alignment of liquid crystal molecules is lost, and a panel defect is generated. have.
또한, 정전기는 먼지나 오물을 흡인하는 문제나 작업성 저하의 문제 등을 야기할 가능성을 가지고 있다. 그래서, 상기 문제점을 해소하기 위해 표면보호필름에 각종 대전방지 처리가 실시되고 있다.In addition, static electricity has a possibility of causing a problem of sucking dust and dirt, a problem of deterioration in workability, and the like. Thus, in order to solve the above problems, various antistatic treatments have been carried out on the surface protective film.
일본특허공개공보 제1997-165460호는 점착제에 저분자량 계면활성제를 첨가하고, 점착제로부터 계면활성제를 피보호체에 전사시켜 대전을 방지하는 방법을 개시하고 있다. 그러나, 이 방법에서는 첨가한 저분자량의 계면활성제가 점착제 표면으로 흘러나오기 쉬워, 표면보호필름에 적용한 경우 피보호체에 대한 오염의 우려가 있다. 따라서, 저분자 계면활성제를 첨가한 점착제를 광학부재용 보호필름에 적용한 경우에는 특히 광학부재의 광학 특성을 손상시키는 문제점이 있다.Japanese Patent Laid-Open No. 1997-165460 discloses a method for preventing charging by adding a low molecular weight surfactant to an adhesive and transferring the surfactant from the adhesive to the protected object. However, in this method, the added low molecular weight surfactant easily flows out onto the pressure-sensitive adhesive surface, and there is a fear of contamination to the to-be-protected body when applied to the surface protective film. Therefore, in the case where the pressure-sensitive adhesive to which the low molecular weight surfactant is added is applied to the protective film for the optical member, there is a problem in particular that impairs the optical properties of the optical member.
또한, 일본특허공개공보 제1994-128539호는 대전방지제를 점착제층에 함유시킨 점착 시트를 개시하고 있다. 상기 기술에서는 점착제 표면으로 대전방지제가 흘러나오는 것을 억제하기 위해, 폴리에테르 폴리올 화합물과 알칼리 금속염으로 이루어진 대전방지제를 점착제에 첨가하고 있다. 그러나, 이러한 점착 시트류를 사용하여도 대전방지제 등이 흘러나오는 현상은 억제될 수 없고, 그 결과 실제 표 면보호필름에 적용한 경우, 경시 또는 고온 조건 하에서 처리하게 되면, 표면보호필름의 부분적 들뜸 현상이 발생하게 되는 문제점이 있다.In addition, Japanese Patent Laid-Open Publication No. 1994-128539 discloses an adhesive sheet containing an antistatic agent in an adhesive layer. In the above technique, an antistatic agent made of a polyether polyol compound and an alkali metal salt is added to the pressure sensitive adhesive to prevent the antistatic agent from flowing out onto the pressure sensitive adhesive surface. However, even when such adhesive sheets are used, the phenomenon that the antistatic agent flows out cannot be suppressed. As a result, when applied to the actual surface protective film, the surface protective film is partially lifted if treated under time or high temperature conditions. There is a problem that occurs.
본 발명은 전술한 종래 기술의 문제점을 고려하여 된 것으로, 우수한 점착 물성, 재박리성, 비오염성 및 작업성을 가지면서도, 탁월한 대전방지성능을 구현할 수 있고, 또한 경시적인 물성의 저하가 방지되는 점착제 조성물, 그를 포함하는 점착 필름, 편광판 및 액정표시장치를 제공하는 것을 목적으로 한다.The present invention has been made in consideration of the problems of the prior art described above, while having excellent adhesive properties, re-peelability, non-pollution property and workability, it is possible to implement excellent antistatic performance, and also to prevent the deterioration of physical properties over time An object of the present invention is to provide an adhesive composition, an adhesive film, a polarizing plate, and a liquid crystal display device including the same.
본 발명은 상기 과제를 해결하기 위한 수단으로서, 방사선 중합성기를 함유하는 베이스 수지; 및The present invention provides a means for solving the above problems, a base resin containing a radiation polymerizable group; And
방사선 중합성기를 함유하는 대전방지성 화합물을 포함하는 점착제 조성물을 제공한다.Provided is an adhesive composition comprising an antistatic compound containing a radiation polymerizable group.
본 발명은 상기 과제를 해결하기 위한 다른 수단으로서, 기재 필름; 및 상기 기재 필름의 일면 또는 양면에 형성되고, 본 발명에 따른 점착제 조성물의 경화물을 함유하는 점착층을 포함하는 점착 필름을 제공한다.The present invention is another means for solving the above problems, a base film; And a pressure-sensitive adhesive layer formed on one or both surfaces of the base film and containing a cured product of the pressure-sensitive adhesive composition according to the present invention.
본 발명은 상기 과제를 해결하기 위한 또 다른 수단으로서, 본 발명에 따른 점착 필름이 일면 또는 양면에 부착된 편광판을 제공한다.As another means for solving the above problems, the present invention provides a polarizing plate attached to one or both sides of the adhesive film according to the present invention.
본 발명은 또한 상기 과제를 해결하기 위한 또 다른 수단으로서, 본 발명의 점착 필름이 부착된 편광판이 액정 패널의 일면 또는 양면에 부착된 액정표시장치를 제공한다.The present invention also provides a liquid crystal display device in which a polarizing plate with an adhesive film of the present invention is attached to one side or both sides of a liquid crystal panel as another means for solving the above problems.
본 발명에서는 점착제 조성물에 포함되는 대전방지성 화합물에 방사선 중합성기가 도입되어, 상기 화합물이 방사선의 조사에 의한 경화 반응 시에 주사슬 또는 다관능성 화합물과 결합될 수 있다. 이에 따라, 본 발명에서는 탁월한 점착 물성, 재박리성, 비오염성 및 작업성을 가지고, 소량의 대전방지성분을 사용하면서도 탁월한 대전방지성능을 구현할 수 있으며, 또한 경시적인 물성(ex. 대전방지성)의 저하가 방지되는 점착제 조성물을 제공할 수 있다. 이에 따라 본 발명의 점착제 조성물은, 예를 들면, 편광판용 표면보호필름 등으로 효과적으로 사용될 수 있다.In the present invention, a radiation polymerizable group is introduced into the antistatic compound included in the pressure-sensitive adhesive composition, and the compound may be combined with a main chain or a polyfunctional compound during a curing reaction by irradiation of radiation. Accordingly, the present invention has excellent adhesion properties, re-peelability, non-pollution and workability, and can implement excellent antistatic performance while using a small amount of antistatic components, and also over time (ex. Antistatic properties) It is possible to provide the pressure-sensitive adhesive composition in which the fall of the resin is prevented. Accordingly, the pressure-sensitive adhesive composition of the present invention can be effectively used, for example, as a surface protective film for a polarizing plate.
본 발명은, 방사선 중합성기를 함유하는 베이스 수지; 및 The present invention is a base resin containing a radiation polymerizable group; And
방사선 중합성기를 함유하는 대전방지성 화합물을 포함하는 점착제 조성물에 관한 것이다.The present invention relates to an adhesive composition containing an antistatic compound containing a radiation polymerizable group.
이하, 본 발명에 따른 점착제 조성물을 상세히 설명한다.Hereinafter, the pressure-sensitive adhesive composition according to the present invention will be described in detail.
본 발명의 점착제 조성물에서 사용되는 베이스 수지의 종류는, 방사선에 의 해 중합 반응을 진행할 수 있는 관능기를 포함하는 점착성 수지라면 특별히 한정되지 않는다. 본 발명에서 사용하는 용어 「방사선」은 점착제 조성물에 포함된 중합성기 또는 개시제 등에 영향을 주어 경화 반응을 진행시킬 수 있는 에너지선으로서, 전자선 및 자외선 등을 포함하는 개념이다.The kind of base resin used by the adhesive composition of this invention will not be specifically limited if it is adhesive resin containing the functional group which can advance a polymerization reaction by radiation. The term "radiation" used in the present invention is an energy ray capable of affecting the polymerizable group or the initiator contained in the pressure-sensitive adhesive composition or the like to advance the curing reaction, and is a concept including an electron beam and ultraviolet rays.
본 발명에서는, 예를 들면, 베이스 수지로서, (메타)아크릴산 에스테르계 단량체 및 관능기 함유 단량체를 함유하는 주사슬; 및 In the present invention, for example, a main chain containing a (meth) acrylic acid ester monomer and a functional group-containing monomer as a base resin; And
상기 주사슬의 측쇄에 결합된 방사선 중합성기 함유 화합물을 포함하는 공중합체를 사용할 수 있다.The copolymer containing the radiation polymerizable group containing compound couple | bonded with the side chain of the said main chain can be used.
상기에서 주사슬에 포함되는 (메타)아크릴산 에스테르계 단량체의 종류는 특별히 한정되지 않으며, 예를 들면, 알킬 (메타)아크릴레이트를 사용할 수 있다. 이 경우, 단량체에 포함되는 알킬기가 지나치게 장쇄가 되면, 점착제의 응집력이 저하되고, 유리전이온도 및 점착성의 조절이 어려워질 우려가 있으므로, 탄소수가 1 내지 14인 알킬기를 갖는 (메타)아크릴산 에스테르계 단량체를 사용하는 것이 바람직하다. 이와 같은 단량체의 예로는 메틸 (메타)아크릴레이트, 에틸 (메타)아크릴레이트, n-프로필 (메타)아크릴레이트, 이소프로필 (메타)아크릴레이트, n-부틸 (메타)아크릴레이트, t-부틸 (메타)아크릴레이트, sec-부틸 (메타)아크릴레이트, 펜틸 (메타)아크릴레이트, 2-에틸부틸 (메타)아크릴레이트, 2-에틸헥실 (메타)아크릴레이트, n-옥틸 (메타)아크릴레이트, 이소옥틸 (메타)아크릴레이트, 이소노닐 (메타)아크릴레이트, 라우릴 (메타)아크릴레이트 및 테트라데실 (메타)아크릴레이트 등의 일종 또는 이종 이상의 혼합을 들 수 있다.The kind of the (meth) acrylic acid ester monomer contained in the main chain is not particularly limited, and alkyl (meth) acrylate can be used, for example. In this case, when the alkyl group contained in the monomer is too long, the cohesive force of the pressure-sensitive adhesive may be lowered, and the glass transition temperature and the adhesiveness may become difficult to control. Therefore, the (meth) acrylic acid ester system having an alkyl group having 1 to 14 carbon atoms Preference is given to using monomers. Examples of such monomers include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, t-butyl ( Meth) acrylate, sec-butyl (meth) acrylate, pentyl (meth) acrylate, 2-ethylbutyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, And a mixture of one or more kinds of isooctyl (meth) acrylate, isononyl (meth) acrylate, lauryl (meth) acrylate and tetradecyl (meth) acrylate.
상기와 같은 (메타)아크릴산 에스테르계 단량체는 주사슬의 전체 100 중량부 대비 80 중량부 내지 99.8 중량부, 바람직하게는, 90 중량부 내지 99 중량부의 양으로 포함될 수 있다. 상기 함량이 80 중량부 미만이면, 점착제의 초기 접착력이 저하될 우려가 있고, 99.8 중량부를 초과하면, 응집력 저하로 인해 내구성에 문제가 발생할 우려가 있다.Such a (meth) acrylic acid ester monomer may be included in an amount of 80 parts by weight to 99.8 parts by weight, preferably 90 parts by weight to 99 parts by weight, based on 100 parts by weight of the main chain. If the content is less than 80 parts by weight, there is a fear that the initial adhesive strength of the pressure-sensitive adhesive is lowered, if it exceeds 99.8 parts by weight, there is a fear that durability problems occur due to the decrease in cohesive force.
주사슬은 상기 (메타)아크릴산 에스테르계 단량체와 함께 관능기 함유 단량체를 포함할 수 있고, 상기는 주사슬에 방사선 중합성기 함유 화합물과 반응할 수 있는 관능기를 부여하는 역할을 한다. 이와 같은 관능기의 예로는 히드록시기, 카복실기, 이소시아네이트기, 아미노기 또는 에폭시기 등을 들 수 있고, 본 발명에서는 히드록시기 또는 카복실기를 사용하는 것이 바람직하지만, 이에 제한되는 것은 아니다. The main chain may include a functional group-containing monomer together with the (meth) acrylic acid ester monomer, and serves to impart a functional group capable of reacting with the radiation polymerizable group-containing compound to the main chain. Examples of such functional groups include a hydroxy group, a carboxyl group, an isocyanate group, an amino group or an epoxy group, and in the present invention, it is preferable to use a hydroxy group or a carboxyl group, but is not limited thereto.
본 발명에서 관능기 함유 단량체의 구체적인 종류는, 분자 내에 전술한 관능기 및 불포화 이중 결합을 가지는 것이라면, 특별히 제한되지 않는다. 예를 들면, 본 발명에서는 상기 관능기 함유 단량체로서, 2-히드록시에틸 (메타)아크릴레이트, 2-히드록시프로필 (메타)아크릴레이트, 4-히드록시부틸 (메타)아크릴레이트, 6-히드록시헥실 (메타)아크릴레이트, 8-히드록시옥틸 (메타)아크릴레이트, 2-히드록시에틸렌 글리콜 (메타)아크릴레이트, 2-히드록시프로필렌 글리콜 (메타)아크릴레이트, (메타)아크릴산, 2-(메타)아크릴로일옥시 아세트산, 3-(메타)아크릴로일옥시 프로필산, 4-(메타)아크릴로일옥시 부틸산, 아크릴산 이중체, 이타콘산, 말레산 또는 말레산 무수물의 일종 또는 이종 이상의 혼합을 사용할 수 있으나, 이에 제한되 는 것은 아니다. The specific kind of the functional group-containing monomer in the present invention is not particularly limited as long as it has the aforementioned functional group and unsaturated double bond in the molecule. For example, in the present invention, as the functional group-containing monomer, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxy Hexyl (meth) acrylate, 8-hydroxyoctyl (meth) acrylate, 2-hydroxyethylene glycol (meth) acrylate, 2-hydroxypropylene glycol (meth) acrylate, (meth) acrylic acid, 2- ( One or more kinds of meta) acryloyloxy acetic acid, 3- (meth) acryloyloxy propyl acid, 4- (meth) acryloyloxy butyl acid, acrylic acid duplex, itaconic acid, maleic acid or maleic anhydride Mixing may be used, but is not limited thereto.
본 발명에서 상기 관능기 함유 단량체의 함량은 최종 점착제의 물성 및 주사슬에 도입하고자 하는 방사선 중합성기의 함량에 따라서 결정되는 것으로 특별히 한정되지 않는다. 본 발명에서는, 예를 들면, 주사슬 전체 중량 100 중량부에 대하여 0.01 중량부 내지 20 중량부, 바람직하게는 1 중량부 내지 10 중량부의 양으로 포함될 수 있다.In the present invention, the content of the functional group-containing monomer is not particularly limited as determined according to the physical properties of the final pressure-sensitive adhesive and the content of the radiation polymerizable group to be introduced into the main chain. In the present invention, for example, it may be included in an amount of 0.01 to 20 parts by weight, preferably 1 to 10 parts by weight based on 100 parts by weight of the main chain.
본 발명의 베이스 수지는 전술한 주사슬과 함께, 상기 주사슬의 측쇄에 결합되어 방사선 중합성기를 부여하는 화합물을 추가로 포함할 수 있다. The base resin of the present invention may further include a compound which is bonded to the side chain of the main chain and gives a radiation polymerizable group together with the main chain described above.
이와 같은 화합물의 구체적인 종류는, 방사선 중합성기(ex. 방사선 중합성 탄소-탄소 이중 결합)를 한 분자당 1 내지 5개, 바람직하게는 1 내지 2개 포함하고, 또한 주사슬에 포함되는 관능기와 반응할 수 있는 관능기를 가지는 한, 특별히 제한되지 않는다. 상기에서 주사슬의 관능기와 반응할 수 있는 관능기의 예로는, 이소시아네이트기, 에폭시기, 실란기 또는 카복실기 등을 들 수 있으나, 이에 제한되는 것은 아니다. 예를 들어, 주사슬에 히드록시기 또는 카복실기가 도입된 경우에는, 상기 화합물에 포함되는 관능기는 이소시아네이트기, 에폭시기 또는 클로로실란기 등일 수 있고, 주사슬에 아미노기 또는 치환 아미노기가 도입되는 경우에는, 이소시아네이트기 등이 상기 화합물에 포함되는 것이 바람직하며, 주사슬에 에폭시기가 포함되는 경우, 상기 관능기는 카복실기를 사용할 수 있다. A specific kind of such a compound includes a functional group containing 1 to 5, preferably 1 to 2, molecules of a radiation polymerizable group (e.g., a radiation polymerizable carbon-carbon double bond) in a main chain. It does not restrict | limit especially as long as it has a functional group which can react. Examples of the functional group capable of reacting with the functional group of the main chain include an isocyanate group, an epoxy group, a silane group or a carboxyl group, but are not limited thereto. For example, when a hydroxyl group or a carboxyl group is introduced into the main chain, the functional group included in the compound may be an isocyanate group, an epoxy group or a chlorosilane group, or the like, and when an amino group or a substituted amino group is introduced into the main chain, an isocyanate group It is preferable that etc. are contained in the said compound, and when an epoxy group is contained in a principal chain, the said functional group can use a carboxyl group.
본 발명에서 사용할 수 있는 방사선 중합성기 함유 화합물의 구체적인 예로 는, 2-이소시아네이토에틸 (메타)아크릴레이트, 1,1-비스(아크릴로일옥시메틸)에틸 이소시아네이트, (메타)아크릴로일옥시 에틸 이소시아네이트, 메타-이소프로페닐-α,α-디메틸벤질이소시아네이트, 메타크릴로일이소시아네이트 또는 알릴 이소시아네이트; 디이소시아네이트 화합물 또는 폴리이소시아네이트 화합물을 (메타)아크릴산 2-히드록시에틸과 반응시켜 얻어지는 아크릴로일 모노이소시아네이트 화합물; 디이소시아네이트 화합물 또는 폴리이소시아네이트 화합물, 폴리올화합물 및 (메타)아크릴산 2-히드록시에틸을 반응시켜 얻어지는 아크릴로일 모노이소시아네이트 화합물; (메타)아크릴산 글리시딜; (메타)아크릴산; 또는 3-메타크릴록시프로필디메틸클로로실란 등의 일종 또는 이종 이상을 들 수 있으나, 이에 제한되는 것은 아니다.Specific examples of the radiation polymerizable group-containing compound which can be used in the present invention include 2-isocyanatoethyl (meth) acrylate, 1,1-bis (acryloyloxymethyl) ethyl isocyanate, and (meth) acryloyl jade. Ethyl ethyl isocyanate, meta-isopropenyl-α, α-dimethylbenzyl isocyanate, methacryloyl isocyanate or allyl isocyanate; An acryloyl monoisocyanate compound obtained by reacting a diisocyanate compound or a polyisocyanate compound with 2-hydroxyethyl (meth) acrylate; An acryloyl monoisocyanate compound obtained by reacting a diisocyanate compound or polyisocyanate compound, a polyol compound and 2-hydroxyethyl (meth) acrylate; Glycidyl (meth) acrylate; (Meth) acrylic acid; Or 3-methacryloxypropyldimethylchlorosilane, or the like, or a heterogeneous compound, but is not limited thereto.
상기와 같은 방사선 중합성기 함유 화합물의 함량은 목적하는 용도에 따라 선택되는 것으로 특별히 한정되는 것은 아니며, 예를 들면, 주사슬에 포함되는 관능기 함유 단량체 100 당량 당 5 당량 내지 100 당량의 비율로 포함될 수 있다.The content of the radiation polymerizable group-containing compound as described above is not particularly limited to be selected according to the intended use, and may be included in a ratio of 5 to 100 equivalents per 100 equivalents of the functional group-containing monomer included in the main chain, for example. have.
본 발명에서, 상기와 같은 베이스 수지를 제조하는 방법은 특별히 한정되지 않으며, 예를 들면, 주사슬을 이루는 공중합체 및 방사선 중합성기 함유 화합물을 실온 내지 40℃의 온도의 상압에서 4 시간 내지 48 시간 동안 반응시켜 제조할 수 있다. 이 때 상기 반응은 아세트산 에틸 등의 용매 내에서 유기 주석 등의 촉매를 사용하여 수행할 수 있다.In the present invention, the method for producing the base resin as described above is not particularly limited. For example, the copolymer and the radiation polymerizable group-containing compound forming the main chain are 4 hours to 48 hours at normal pressure at a temperature of room temperature to 40 ° C. Can be prepared by reaction. At this time, the reaction may be carried out using a catalyst such as organic tin in a solvent such as ethyl acetate.
또한, 본 발명에서 주사슬을 이루는 공중합체를 제조하는 방법 역시 특별히 한정되지 않으며, 예를 들면 용액 중합, 광중합, 벌크 중합, 서스펜션 중합 또는 에멀션 중합과 같은 일반적인 중합법을 통하여 제조할 수 있다. 본 발명에서는 특히 용액 중합법을 사용하는 것이 바람직한데, 용액 중합은 각각의 단량체가 균일하게 혼합된 상태에서 개시제를 혼합하여, 50℃ 내지 140℃의 중합 온도로 수행하는 것이 바람직하다. 이 때 사용될 수 있는 개시제로는 아조비스 이소부티로니트릴 또는 아조비스시클로헥산 카르보니트릴과 같은 아조계 중합 개시제; 및/또는 과산화 벤조일 또는 과산화 아세틸과 같은 과산화물 등의 통상의 개시제를 들 수 있다.In addition, the method for preparing the main chain copolymer in the present invention is also not particularly limited, and for example, may be prepared through a general polymerization method such as solution polymerization, photopolymerization, bulk polymerization, suspension polymerization or emulsion polymerization. In the present invention, it is particularly preferable to use a solution polymerization method, and solution polymerization is preferably performed at a polymerization temperature of 50 ° C to 140 ° C by mixing an initiator in a state where each monomer is uniformly mixed. Initiators which can be used at this time include azo polymerization initiators such as azobis isobutyronitrile or azobiscyclohexane carbonitrile; And / or conventional initiators such as peroxides such as benzoyl peroxide or acetyl peroxide.
본 발명의 점착제 조성물은 전술한 베이스 수지와 함께 방사선 중합성기를 함유하는 대전방지성 화합물을 추가로 포함한다. The pressure-sensitive adhesive composition of the present invention further includes an antistatic compound containing a radiation polymerizable group together with the base resin described above.
본 발명에서 사용할 수 있는 상기 대전방지성 화합물의 종류는, 분자 내에 방사선 중합성기를 함유하고, 점착제의 물성을 해치지 않으면서 대전방지성능을 구현할 수 있는 것이라면, 특별히 한정되지 않는다.The type of the antistatic compound that can be used in the present invention is not particularly limited as long as it contains a radiation polymerizable group in a molecule and can realize antistatic performance without harming the physical properties of the pressure-sensitive adhesive.
본 발명에서는, 예를 들면, 상기 대전방지성 화합물로서, 금속 원자가 부가된 디올계 화합물 및 방사선 중합성기 함유 화합물의 반응물을 포함하는 화합물을 사용할 수 있다.In the present invention, for example, a compound containing a reactant of a diol-based compound to which a metal atom is added and a radiation polymerizable group-containing compound can be used as the antistatic compound.
본 발명에서 사용할 수 있는 디올 화합물의 종류는 특별히 한정되지 않으며, 예를 들면, 에틸렌 글리콜, 프로필렌 글리콜, 테트라메틸렌 글리콜, 1,3-부탄디올, 1,4-부탄디올, 네오펜틸글리콜, 1,6-헥산디올 또는 1,9-노난 디올 등과 같은 탄소수 2 내지 100의 직쇄 또는 분지쇄 알킬렌 글리콜; 비스페놀 A; 디에틸렌 글리콜, 폴리에틸렌 글리콜, 폴리프로필렌 글리콜, 폴리테트라메틸렌 글리콜, 폴리에틸렌 글리콜-폴리프로필렌 글리콜 공중합체, 비스페놀 A의 에틸렌옥시드 개환 부가물 또는 비스페놀 A의 프로필렌옥시드 개환 부가물 등과 같은 알킬렌 글리콜 및/또는 비스페놀 A의 축합물; 또는 폴리아디페이트 디올, 폴리카보네이트 디올 또는 폴리카프로락톤 디올 등과 같은 폴리에스테르 디올을 들 수 있고, 본 발명에서는 상기 중 일종 또는 이종 이상의 혼합을 사용할 수 있으나, 이에 제한되는 것은 아니다. The kind of diol compound which can be used by this invention is not specifically limited, For example, ethylene glycol, propylene glycol, tetramethylene glycol, 1, 3- butanediol, 1, 4- butanediol, neopentyl glycol, 1, 6- Straight or branched chain alkylene glycols having 2 to 100 carbon atoms such as hexanediol or 1,9-nonane diol; Bisphenol A; Alkylene glycols such as diethylene glycol, polyethylene glycol, polypropylene glycol, polytetramethylene glycol, polyethylene glycol-polypropylene glycol copolymers, ethylene oxide ring opening adducts of bisphenol A, or propylene oxide ring opening adducts of bisphenol A; Condensates of bisphenol A; Or a polyester diol such as polyadipate diol, polycarbonate diol or polycaprolactone diol, and the like, but the present invention may use one kind or a mixture of two or more of them, but is not limited thereto.
본 발명에서 바람직하게는 탄소수 2 내지 100의 직쇄 또는 분지쇄 알킬렌 글리콜의 축합물을 사용할 수 있고, 특히 바람직하게는 폴리에틸렌 글리콜, 폴리프로필렌 글리콜 또는 폴리에틸렌 글리콜-폴리프로필렌 글리콜 공중합체의 일종 또는 이종 이상의 혼합을 사용할 수 있다. In the present invention, condensates of linear or branched alkylene glycols having 2 to 100 carbon atoms are preferably used, and particularly preferably, one or more kinds of polyethylene glycol, polypropylene glycol, or polyethylene glycol-polypropylene glycol copolymers. Mixing can be used.
본 발명에서 상기와 같은 디올 화합물은 분자량 또는 중량평균분자량이 50 내지 10,000, 바람직하게는 100 내지 5,000, 보다 바람직하게는 500 내지 2,000일 수 있다.In the present invention, such a diol compound may have a molecular weight or a weight average molecular weight of 50 to 10,000, preferably 100 to 5,000, more preferably 500 to 2,000.
본 발명에서, 상기와 같은 디올 화합물에 부가될 수 있는 금속 원자의 종류는 특별히 한정되지 않으며, 예를 들면 리튬, 나트륨, 칼륨, 루비듐, 세슘 또는 프랑슘 등과 같은 알칼리 금속을 사용할 수 있고, 바람직하게는 리튬, 나트륨 또는 칼륨, 보다 바람직하게는 리튬을 사용할 수 있으나, 이에 제한되는 것은 아니다.In the present invention, the kind of metal atoms which can be added to the diol compound as described above is not particularly limited, and for example, alkali metals such as lithium, sodium, potassium, rubidium, cesium or francium can be used, and preferably Lithium, sodium or potassium, more preferably lithium may be used, but is not limited thereto.
본 발명에서 상기와 같은 금속 원자는 대전방지성 화합물 전체 100 중량부에 대하여 0.01 중량부 내지 20 중량부의 양으로 포함되는 것이 바람직하다. 상기 함량이 0.01 중량부 미만이면, 충분한 대전방지 성능이 확보되지 않을 우려가 있고, 20 중량부를 초과하면, 금속 원자를 디올 화합물에 부가할 때에 발열이 과도하게 일어나거나 또는 반응 제어가 어려워질 우려가 있다. In the present invention, such metal atoms are preferably included in an amount of 0.01 to 20 parts by weight based on 100 parts by weight of the total antistatic compound. If the content is less than 0.01 part by weight, there is a fear that sufficient antistatic performance is not secured, and if it exceeds 20 parts by weight, excessive heat generation or difficulty in controlling the reaction may occur when adding a metal atom to the diol compound. have.
본 발명의 대전방지성 화합물에 포함되는 방사선 중합성기 함유 화합물의 종류는, 분자 중에 방사선 중합성기(ex. 탄소-탄소 이중결합) 및 상기 디올 화합물과 반응할 수 있는 관능기(ex. 이소시아네이트기)를 동시에 포함하는 것이라면, 특별히 한정되지 않는다. 본 발명에서는, 예를 들면, 전술한 베이스 수지에 포함되는 방사선 중합성기 함유 화합물 중 적절한 종류를 선택하여 사용할 수 있다.The kind of the radiation polymerizable group-containing compound included in the antistatic compound of the present invention includes a radiopolymerizable group (ex. Carbon-carbon double bond) and a functional group (ex. Isocyanate group) capable of reacting with the diol compound in the molecule. If it contains simultaneously, it will not specifically limit. In this invention, an appropriate kind can be selected and used, for example among the radiation polymerizable group containing compounds contained in the base resin mentioned above.
본 발명의 대전방지성 화합물에서 상기 방사선 중합성기 함유 화합물은, 예를 들면, 디올 화합물에 포함되는 관능기 100 당량 당 5 당량 내지 100 당량의 비율로 포함될 수 있다.In the antistatic compound of the present invention, the radiation polymerizable group-containing compound may be included, for example, in a ratio of 5 equivalents to 100 equivalents per 100 equivalents of the functional group included in the diol compound.
본 발명에서 상기와 같은 대전방지성 화합물을 제조하는 방법은 특별히 한정되지 않는다. 예를 들면, 상기 화합물은 적정한 조건에서 디올 화합물에 금속 원자를 부가한 후, 다시 방사선 중합성기 함유 화합물을 결합시킴으로써 제조할 수 있다.In the present invention, the method for producing such an antistatic compound is not particularly limited. For example, the compound can be prepared by adding a metal atom to the diol compound under appropriate conditions, and then again combining the radiation polymerizable group-containing compound.
상기에서 금속 원자의 부가 반응은, 예를 들면, 디올 화합물에 MClO4(상기에서 M은 금속 원자)로 표시되는 과염소산염을, 톨루엔, 벤젠, 초산 에스테르, 메틸에틸케톤 또는 아세톤 등의 용매 중 또는 무용매 하에서, 상온 또는 가열 하에 반응시킴으로써 수행할 수 있다. 상기에서 과염소산염의 사용량은 도입하고자 하는 금속 원자의 양에 따라 정해지며, 또한 가열 시의 온도는 30℃ 내지 100℃일 수 있 다. 또한, 상기 반응은 통상 1 시간 내지 20 시간 동안 수행될 수 있으나, 이에 제한되는 것은 아니다.The addition reaction of the metal atoms in the above, for example, to the diol compound perchlorate represented by MClO 4 (M is a metal atom), in a solvent such as toluene, benzene, acetate ester, methyl ethyl ketone or acetone or It can be carried out by reacting at room temperature or under heating without solvent. The amount of perchlorate used is determined according to the amount of metal atoms to be introduced, and the temperature at the time of heating may be 30 ° C to 100 ° C. In addition, the reaction may be generally performed for 1 to 20 hours, but is not limited thereto.
본 발명에서, 상기와 같이 디올 화합물에 금속 원자를 부가한 후에, 방사선 중합성기 함유 화합물과 반응시키는 방법은 특별히 한정되지 않는다. 예를 들면, 디올계 화합물 및 방사선 중합성기 함유 화합물을 실온 내지 40℃의 온도의 상압에서 4 시간 내지 48 시간 동안 반응시켜 제조할 수 있다. 이 때 상기 반응은 아세트산 에틸 등의 용매 내에서 유기 주석 등의 촉매를 사용하여 수행할 수 있다.In this invention, the method of reacting with a radiation polymerizable group containing compound after adding a metal atom to a diol compound as mentioned above is not specifically limited. For example, the diol-based compound and the radiation polymerizable group-containing compound may be prepared by reacting for 4 hours to 48 hours at a normal pressure of room temperature to 40 ℃. At this time, the reaction may be carried out using a catalyst such as organic tin in a solvent such as ethyl acetate.
상기와 같은 대전방지성 화합물은 상기 베이스 수지 100 중량부에 대하여 0.1 중량부 내지 30 중량부, 바람직하게는 1 중량부 내지 10 중량부의 양으로 점착제 조성물에 포함될 수 있다. 상기 함량이 0.1 중량부 미만이면, 목적하는 대전방지성능이 얻어지지 않을 우려가 있고, 30 중량부를 초과하면, 점착 성능이 저하될 우려가 있다.The antistatic compound as described above may be included in the pressure-sensitive adhesive composition in an amount of 0.1 to 30 parts by weight, preferably 1 to 10 parts by weight, based on 100 parts by weight of the base resin. If the content is less than 0.1 part by weight, the desired antistatic performance may not be obtained. If it exceeds 30 parts by weight, the adhesion performance may be lowered.
본 발명의 점착제 조성물은 전술한 성분과 함께 다관능성 화합물을 추가로 포함할 수 있다. 상기 다관능성 화합물은 점착제 조성물의 경화 반응에 참여하여, 점착제에 우수한 가교 구조를 구현하는 역할을 한다.The pressure-sensitive adhesive composition of the present invention may further include a multifunctional compound together with the above-described components. The multifunctional compound participates in the curing reaction of the pressure-sensitive adhesive composition, and serves to implement an excellent crosslinked structure in the pressure-sensitive adhesive.
본 발명에서 사용할 수 있는 다관능성 화합물의 종류는 특별히 한정되지 않으며, 예를 들면, 다관능성 아크릴레이트를 사용할 수 있다. 본 발명에서는 이와 같은 다관능성 아크릴레이트로서 분자량이 1,000 미만인 것으로, 2개 이상의 관능기를 함유하는 것을 사용할 수 있으며, 3개 이상의 관능기를 함유하는 다관능 아크릴레이트를 사용하는 것이 보다 바람직하지만, 이에 제한되는 것은 아니다. 상기 다관능성 아크릴레이트의 구체적인 예로는, 1,4-부탄디올 디(메타)아크릴레이트, 1,6-헥산디올 디(메타)아크릴레이트, 네오펜틸글리콜 디(메타)아크릴레이트, 폴리에틸렌글리콜 디(메타)아크릴레이트, 네오펜틸글리콜아디페이트(neopentylglycol adipate) 디(메타)아크릴레이트, 히드록시피발산(hydroxyl puivalic acid) 네오펜틸글리콜 디(메타)아크릴레이트, 디시클로펜타닐(dicyclopentanyl) 디(메타)아크릴레이트, 카프로락톤 변성 디시클로펜테닐 디(메타)아크릴레이트, 에틸렌옥시드 변성 디(메타)아크릴레이트, 디(메타)아크릴록시 에틸 이소시아누레이트, 알릴(allyl)화 시클로헥실 디(메타)아크릴레이트, 트리시클로데칸디메탄올(메타)아크릴레이트, 디메틸롤 디시클로펜탄 디(메타)아크릴레이트, 에틸렌옥시드 변성 헥사히드로프탈산 디(메타)아크릴레이트, 트리시클로데칸 디메탄올(메타)아크릴레이트, 네오펜틸글리콜 변성 트리메틸프로판 디(메타)아크릴레이트, 아다만탄(adamantane) 디(메타)아크릴레이트 또는 9,9-비스[4-(2-아크릴로일옥시에톡시)페닐]플루오렌(fluorine) 등의 2관능형; 트리메틸롤프로판 트리(메타)아크릴레이트, 디펜타에리쓰리톨 트리(메타)아크릴레이트, 프로피온산 변성 디펜타에리쓰리톨 트리(메타)아크릴레이트, 펜타에리쓰리톨 트리(메타)아크릴레이트, 프로필렌옥시드 변성 트리메틸롤프로판 트리(메타)아크릴레이트, 3관능형 우레탄 (메타)아크릴레이트 또는 트리스(메타)아크릴록시에틸이소시아누레이트 등의 3관능형; 디글리세린 테트라(메타)아크릴레이트 또는 펜타에리쓰리톨 테트라(메타)아크릴레이트 등의 4관능형; 프로피온산 변성 디펜타에리쓰리톨 펜타(메타)아크릴레이트 등의 5관능형; 및 디펜타에리쓰리톨 헥사(메타)아크릴레이트, 카프로락톤 변성 디펜타에리쓰리톨 헥사(메 타)아크릴레이트 또는 우레탄 (메타)아크릴레이트(ex. 이소시아네이트 단량체 및 트리메틸롤프로판 트리(메타)아크릴레이트의 반응물 등)(ex. Kyoeisha(사)의 UA-306I 또는 UA-306T) 등의 6관능형 등을 들 수 있으나, 이에 제한되는 것은 아니다.The kind of polyfunctional compound which can be used by this invention is not specifically limited, For example, polyfunctional acrylate can be used. In the present invention, as the multifunctional acrylate having a molecular weight of less than 1,000, those containing two or more functional groups can be used, and it is more preferable to use a multifunctional acrylate containing three or more functional groups, but the present invention is limited thereto. It is not. Specific examples of the multifunctional acrylate include 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, and polyethylene glycol di (meth). ) Acrylate, neopentylglycol adipate di (meth) acrylate, hydroxyl puivalic acid neopentylglycol di (meth) acrylate, dicyclopentanyl di (meth) acrylic Latex, caprolactone modified dicyclopentenyl di (meth) acrylate, ethylene oxide modified di (meth) acrylate, di (meth) acryloxy ethyl isocyanurate, allylated cyclohexyl di (meth) Acrylate, tricyclodecane dimethanol (meth) acrylate, dimethylol dicyclopentane di (meth) acrylate, ethylene oxide modified hexahydrophthalic acid di (meth) acrylate, Ricyclodecane dimethanol (meth) acrylate, neopentylglycol modified trimethylpropane di (meth) acrylate, adamantane di (meth) acrylate or 9,9-bis [4- (2-acrylo) Bifunctional types such as yloxyethoxy) phenyl] fluorine; Trimethylolpropane tri (meth) acrylate, dipentaerythritol tri (meth) acrylate, propionic acid modified dipentaerythritol tri (meth) acrylate, pentaerythritol tri (meth) acrylate, propylene oxide Trifunctional types such as modified trimethylolpropane tri (meth) acrylate, trifunctional urethane (meth) acrylate or tris (meth) acryloxyethyl isocyanurate; Tetrafunctional types such as diglycerin tetra (meth) acrylate or pentaerythritol tetra (meth) acrylate; 5-functional types, such as propionic acid modified dipentaerythritol penta (meth) acrylate; And dipentaerythritol hexa (meth) acrylate, caprolactone modified dipentaerythritol hexa (meth) acrylate or urethane (meth) acrylate (ex. Isocyanate monomer and trimethylolpropane tri (meth) acrylate And a six-functional type such as UA-306I or UA-306T of Kyoeisha Co., Ltd., etc., but is not limited thereto.
상기 다관능성 화합물은, 베이스 수지 100 중량부에 대하여, 30 중량부 이하, 바람직하게는 0.05 중량부 내지 30 중량부, 보다 바람직하게는 0.05 중량부 내지 20 중량부의 양으로 점착제 조성물에 포함될 수 있다. 상기 함량이 30 중량부를 초과하면, 점착제의 박리력이 지나치게 저하하거나, 고온 및/또는 고습 조건 하에서의 내구신뢰성이 저하될 우려가 있다.The polyfunctional compound may be included in the pressure-sensitive adhesive composition in an amount of 30 parts by weight or less, preferably 0.05 part by weight to 30 parts by weight, more preferably 0.05 part by weight to 20 parts by weight, based on 100 parts by weight of the base resin. When the content exceeds 30 parts by weight, the peeling force of the pressure-sensitive adhesive may be excessively lowered, or the durability and reliability under high temperature and / or high humidity conditions may be lowered.
본 발명의 점착제 조성물은 또한 베이스 수지 100 중량부에 대하여, 0.1 중량부 내지 10 중량부, 바람직하게는 0.5 중량부 내지 5 중량부의 광개시제를 추가로 포함할 수 있다. 상기 광개시제는 방사선 등의 조사에 의해 라디칼을 발생시켜, 중합 반응을 개시시키는 역할을 할 수 있다. 본 발명에서 사용될 수 있는 광개시제의 종류는 특별히 한정되지 않으며, 예를 들면, 벤조인, 벤조인 메틸에테르, 벤조인 에틸에테르, 벤조인 이소프로필에테르, 벤조인 n-부틸에테르, 벤조인 이소부틸에테르, 아세토페논, 디메틸아니노 아세토페논, 2,2-디메톡시-2-페닐아세토페논, 2,2-디에톡시-2-페닐아세토페논, 2-히드록시-2-메틸-1-페닐프로판-1온, 1-히드록시시클로헥실페닐케톤, 2-메틸-1-[4-(메틸티오)페닐]-2-몰포리노-프로판-1-온, 4-(2-히드록시에톡시)페닐-2-(히드록시-2-프로필)케톤, 벤조페논, p-페닐벤조페논, 4,4'-디에틸아미노벤조페논, 디클로로벤조페논, 2-메틸안트라퀴논, 2-에틸안트라퀴 논, 2-t-부틸안트라퀴논, 2-아미노안트라퀴논, 2-메틸티오잔톤(thioxanthone), 2-에틸티오잔톤, 2-클로로티오잔톤, 2,4-디메틸티오잔톤, 2,4-디에틸티오잔톤, 벤질디메틸케탈, 아세토페논 디메틸케탈, p-디메틸아미노 안식향산 에스테르, 올리고[2-히드록시-2-메틸-1-[4-(1-메틸비닐)페닐]프로판논] 및 2,4,6-트리메틸벤조일-디페닐-포스핀옥시드 등을 들 수 있다. 본 발명에서는 상기 중 일종 또는 이종 이상을 사용할 수 있다.The pressure-sensitive adhesive composition of the present invention may further include 0.1 to 10 parts by weight, preferably 0.5 to 5 parts by weight of photoinitiator, based on 100 parts by weight of the base resin. The photoinitiator may play a role of generating a radical by irradiation of radiation or the like to initiate a polymerization reaction. The kind of photoinitiator that can be used in the present invention is not particularly limited, and for example, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin n-butyl ether, benzoin isobutyl ether , Acetophenone, dimethylanino acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone, 2-hydroxy-2-methyl-1-phenylpropane- 1-one, 1-hydroxycyclohexylphenyl ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholino-propane-1-one, 4- (2-hydroxyethoxy) phenyl -2- (hydroxy-2-propyl) ketone, benzophenone, p-phenylbenzophenone, 4,4'-diethylaminobenzophenone, dichlorobenzophenone, 2-methylanthraquinone, 2-ethylanthraquinone, 2-t-butylanthraquinone, 2-aminoanthraquinone, 2-methylthioxanthone, 2-ethylthioxanthone, 2-chlorothioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthio Xanthone, Benzyldimethyl Dea, acetophenone dimethyl ketal, p-dimethylamino benzoic acid ester, oligo [2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl] propanone] and 2,4,6-trimethylbenzoyl -Diphenyl-phosphine oxide, etc. are mentioned. In the present invention, one or more of the above can be used.
상기와 같은 광개시제는 베이스 수지 100 중량부에 대하여 0.1 중량부 내지 10 중량부의 양으로 포함되는 것이 바람직하고, 보다 바람직하게는 0.5 중량부 내지 5 중량부의 양으로 포함될 수 있다. 광개시제의 함량이 상기 범위를 초과하면, 중합 반응이 원활히 이루어지지 않거나, 반응 후 잔존 성분으로 인해 점착제 물성이 악화될 우려가 있다.The photoinitiator is preferably included in an amount of 0.1 parts by weight to 10 parts by weight, and more preferably 0.5 parts by weight to 5 parts by weight, based on 100 parts by weight of the base resin. When the content of the photoinitiator exceeds the above range, the polymerization reaction may not be performed smoothly, or the adhesive properties may deteriorate due to the remaining components after the reaction.
본 발명의 점착제 조성물은 또한, 발명의 효과에 영향을 미치지 않는 범위에서, 전술한 성분과 함께, 실란계 커플링제, 점착성 부여 수지, 에폭시 수지, 가교제, 자외선 안정제, 산화 방지제, 조색제, 보강제, 충진제, 소포제, 계면 활성제 및 가소제로 이루어진 군으로부터 선택된 하나 이상의 첨가제를 추가로 포함할 수 있다.The pressure-sensitive adhesive composition of the present invention, in addition to the above-described components, in the range that does not affect the effect of the invention, silane coupling agent, tackifying resin, epoxy resin, crosslinking agent, UV stabilizer, antioxidant, colorant, reinforcing agent, filler It may further comprise one or more additives selected from the group consisting of antifoaming agents, surfactants and plasticizers.
본 발명은 또한, 기재 필름; 및The present invention also provides a base film; And
상기 기재 필름의 일면 또는 양면에 형성되고, 전술한 본 발명에 따른 점착제 조성물의 경화물을 함유하는 점착층을 포함하는 점착 필름에 관한 것이다.It relates to an adhesive film formed on one side or both sides of the base film, and comprising an adhesive layer containing a cured product of the above-described pressure-sensitive adhesive composition.
본 발명의 점착 필름은, 우수한 대전방지성 및 점착 물성을 가져, 각종 전자 제품 또는 가정용 내/외장재에 사용되는 보호필름; 클리닝 시트; 반사 시트; 구조용 점착 필름; 사진용 점착 필름; 차선 표시용 점착 필름; 광학용 점착 제품; 다층 구조의 라미네이트 제품; 의료용 패치; 가열 활성용 점착제품(heat-activated pressure sensitive adhesive article); 또는 전자제품용 점착 필름 등의 각종 산업용 시트 또는 상업용 점착 제품 등에 효과적으로 응용될 수 있다. The pressure-sensitive adhesive film of the present invention has excellent antistatic properties and adhesive physical properties, and a protective film used in various electronic products or home interior / exterior materials; Cleaning sheets; Reflective sheet; Structural adhesive films; Photographic pressure-sensitive adhesive film; Adhesive film for lane marking; Optical adhesive products; Laminate products of multilayer structure; Medical patches; Heat-activated pressure sensitive adhesive articles; Alternatively, the present invention can be effectively applied to various industrial sheets such as adhesive films for electronic products or commercial adhesive products.
특히 본 발명의 점착 필름은 액정표시장치 등에 사용되는 편광판, 파장판, 위상차판, 광학보상필름, 반사시트 및 휘도향상필름 등의 광학 부재 표면을 보호할 목적으로 사용되는 표면보호필름에 효과적으로 사용할 수 있다.In particular, the adhesive film of the present invention can be effectively used in the surface protection film used for the purpose of protecting the surface of the optical member such as polarizing plate, wave plate, retardation plate, optical compensation film, reflecting sheet and brightness enhancement film used in liquid crystal display devices. have.
본 발명에서 사용되는 기재 필름으로는 이 분야의 일반적인 필름을 제한 없이 사용할 수 있으며, 그 예로는 폴리에스테르 필름(ex. 폴리에틸렌테레프탈레이트 필름), 폴리테트라플루오르에틸렌 필름, 폴리에틸렌 필름, 폴리프로필렌 필름, 폴리부텐 필름, 폴리부타디엔 필름, 염화 비닐 공중합체 필름 또는 폴리이미드 필름과 같은 플라스틱 필름을 들 수 있다. 이러한 기재 필름은 단층으로 구성되거나, 2층 이상이 적층되어 있을 수도 있으며, 경우에 따라서는 방오층 또는 대전방지층 등의 기능성층을 추가로 포함할 수도 있다. 본 발명에서는 또한 용도에 따라서 상기 기재 필름으로서 투명성 필름을 사용할 수도 있으며, 기재 밀착성 향상의 관점에서 일면 또는 양면에 프라이머 처리와 같은 표면 처리를 수행할 수도 있다. As the base film used in the present invention, a general film in this field can be used without limitation, and examples thereof include polyester film (ex. Polyethylene terephthalate film), polytetrafluoroethylene film, polyethylene film, polypropylene film, poly And plastic films such as butene films, polybutadiene films, vinyl chloride copolymer films or polyimide films. Such a base film may consist of a single layer, or two or more layers may be laminated | stacked, and may further contain functional layers, such as an antifouling layer or an antistatic layer, in some cases. In the present invention, a transparent film may also be used as the base film according to the use, and surface treatment such as primer treatment may be performed on one or both sides from the viewpoint of improving the substrate adhesion.
본 발명에서, 이러한 기재 필름의 두께는 용도에 따라 적절히 선택되는 것으 로 특별히 한정되지 않으며, 통상적으로 5 ㎛ 내지 500 ㎛, 바람직하게는 10 ㎛ 내지 100 ㎛의 두께로 형성된다. In the present invention, the thickness of the base film is not particularly limited as appropriately selected depending on the application, and is usually formed in a thickness of 5 μm to 500 μm, preferably 10 μm to 100 μm.
또한, 본 발명의 점착 필름에 포함되는 점착층의 두께는 특별히 한정되지 않으며, 예를 들면, 0.5 ㎛ 내지 50 ㎛, 바람직하게는 1 ㎛ 내지 30 ㎛일 수 있다. 점착층의 두께가 전술한 범위를 벗어나면, 균일한 점착층의 형성이 어려워져서 점착 필름의 물성이 불균일해질 우려가 있다.In addition, the thickness of the pressure-sensitive adhesive layer included in the pressure-sensitive adhesive film of the present invention is not particularly limited, and may be, for example, 0.5 μm to 50 μm, preferably 1 μm to 30 μm. When the thickness of the adhesion layer is out of the above-mentioned range, formation of a uniform adhesion layer becomes difficult and there exists a possibility that the physical property of an adhesion film may become nonuniform.
본 발명에서 기재 필름 상에 점착층을 형성하는 방법은 특별히 제한되지 않으며, 예를 들면 상기 필름에 바코터 등의 통상의 수단으로 점착제 조성물을 도포하고 경화시키는 방법, 또는 점착제 조성물을 일단 박리성 기재의 표면에 도포하고 경화시켜, 점착층을 제조한 후에, 상기 박리성 기재를 사용하여 점착층을 기재 필름에 전사하는 방법 등을 사용할 수 있다.The method for forming the adhesive layer on the base film in the present invention is not particularly limited, and for example, a method of applying and curing the pressure-sensitive adhesive composition on the film by conventional means such as a bar coater, or the pressure-sensitive adhesive composition once the peelable substrate After apply | coating and hardening | curing on the surface of and preparing an adhesive layer, the method etc. which transfer an adhesive layer to a base film using the said peelable base material can be used.
점착 편광판의 제조 시에 본 발명의 점착제 조성물을 경화시키는 방법 역시 특별히 한정되지 않고, 이 분야의 일반적인 방법을 적용할 수 있으나, 자외선 또는 전자선과 같은 방사선 조사를 통한 경화 방식이 바람직하고, 이중 자외선 조사를 통한 경화 방식이 보다 바람직하다. The method of curing the pressure-sensitive adhesive composition of the present invention at the time of manufacture of the pressure-sensitive adhesive polarizing plate is also not particularly limited, but a general method in this field may be applied, but a curing method through irradiation with ultraviolet rays or electron beams is preferable, and double ultraviolet irradiation The hardening method through is more preferable.
이와 같은 자외선 조사는, 예를 들면, 고압수은 램프, 무전극 램프 또는 크세논 램프(xenon lamp) 등의 수단을 사용하여 수행할 수 있다.Such ultraviolet irradiation can be performed using means, such as a high pressure mercury lamp, an electrodeless lamp, or a xenon lamp, for example.
자외선 경화 방식에서 조사량은, 점착제층의 제반 물성을 훼손하지 않으면서 충분한 경화가 이루어질 정도로 제어된다면 특별히 제한되지 않으며, 예를 들면, 조도가 50 mW/cm2 내지 1,000 mW/cm2이고, 광량 50 mJ/cm2 내지 1,000 mJ/cm2일 수 있다.In the ultraviolet curing method, the irradiation amount is not particularly limited as long as it is controlled to such a degree that sufficient curing is achieved without impairing the overall physical properties of the pressure-sensitive adhesive layer, for example, the illuminance is 50 mW / cm 2 to 1,000 mW / cm 2 , and the light amount 50 mJ / cm 2 to 1,000 mJ / cm 2 .
본 발명은 또한, 전술한 본 발명에 따른 점착 필름이 일면 또는 양면에 부착된 편광판에 관한 것이다.The present invention also relates to a polarizing plate having the adhesive film according to the present invention described above attached to one side or both sides.
본 발명의 점착 필름이 보호 필름으로서 부착될 수 있는 편광판은, 예를 들면, 편광 필름 또는 편광 소자; 및 상기 편광 필름 또는 편광 소자의 일면 또는 양면에 형성된 보호 필름을 포함하는 구조를 가질 수 있다. 또한, 본 발명의 편광판은, 경우에 따라서는, 보호층, 반사층, 방현층, 위상차판, 광시야각 보상 필름 및 휘도 향상 필름으로 이루어진 군으로부터 선택된 하나 이상의 기능성층을 추가로 포함할 수 있다.The polarizing plate to which the adhesive film of this invention can be attached as a protective film is, for example, a polarizing film or a polarizing element; And a protective film formed on one or both surfaces of the polarizing film or the polarizing element. In addition, the polarizing plate of the present invention may further include one or more functional layers selected from the group consisting of a protective layer, a reflective layer, an antiglare layer, a retardation plate, a wide viewing angle compensation film, and a brightness enhancing film, as the case may be.
본 발명에서 편광판을 구성하는 편광 필름 또는 편광 소자의 종류는 특별히 제한되지 않는다. 예를 들면, 본 발명에서는 편광 필름 또는 편광 소자로서, 폴리비닐알코올계 수지로 되는 필름에 요오드 또는 이색성 염료 등의 편광 성분을 함유시키고, 연신하여 제조되는 필름을 사용할 수 있다. 상기에서 폴리비닐알코올계 수지로는 폴리비닐알코올, 폴리비닐포르말, 폴리비닐아세탈 또는 에틸렌 초산 비닐 공중합체의 검화물 등을 사용할 수 있다. 또한, 상기 편광 필름의 두께 역시 특별히 제한되지 않으며, 통상적인 두께로 형성하면 된다.The kind of polarizing film or polarizing element constituting the polarizing plate in the present invention is not particularly limited. For example, in this invention, the film manufactured by extending | stretching and manufacturing polarizing components, such as iodine or a dichroic dye, can be used for the film which consists of polyvinyl alcohol-type resin as a polarizing film or a polarizing element. As the polyvinyl alcohol-based resin, polyvinyl alcohol, polyvinyl formal, polyvinyl acetal or saponified product of ethylene vinyl acetate copolymer may be used. In addition, the thickness of the polarizing film is also not particularly limited, and may be formed in a conventional thickness.
본 발명의 편광판에서는 편광 소자 또는 편광 필름의 일면 또는 양면에 형성될 수 있는 보호 필름은, 전술한 본 발명의 점착 필름과는 구별되는 개념으로, 그 구체적인 종류로는 트리아세틸 셀룰로오스와 같은 셀룰로오스계 필름; 폴리카보네이트 필름 또는 폴리에틸렌테레프탈레이트 필름과 같은 폴리에스테르계 필름; 폴리에테르설폰계 필름; 및/또는 폴리에틸렌 필름, 폴리프로필렌 필름 또는 시클로계나 노르보르넨 구조를 갖는 폴리올레핀 필름 또는 에틸렌-프로필렌 공중합체와 같은 폴리올레핀계 필름 등을 들 수 있다. 이 때 상기 보호 필름의 두께 역시 특별히 제한되지 않으며, 통상적인 두께로 형성하면 된다.In the polarizing plate of the present invention, a protective film that may be formed on one side or both sides of a polarizing element or a polarizing film is a concept that is distinguished from the above-described adhesive film of the present invention, and a specific kind thereof includes a cellulose-based film such as triacetyl cellulose. ; Polyester film such as polycarbonate film or polyethylene terephthalate film; Polyethersulfone-based films; And / or polyolefin films such as polyethylene films, polypropylene films or polyolefin films having a cyclo or norbornene structure or ethylene-propylene copolymers. At this time, the thickness of the protective film is also not particularly limited, and may be formed in a conventional thickness.
본 발명은 또한 상기 본 발명에 따른 편광판이 액정 패널의 일면 또는 양면에 부착되어 있는 액정표시장치에 관한 것이다.The present invention also relates to a liquid crystal display device in which the polarizing plate according to the present invention is attached to one side or both sides of the liquid crystal panel.
상기와 같은 본 발명의 액정표시장치를 구성하는 액정셀의 종류는 특별히 한정되지 않으며, TN(Twisted Neumatic), STN(Super Twisted Neumatic), IPS(In Plane Switching) 또는 VA(Vertical Alignment) 방식과 같은 일반적인 액정셀을 모두 포함한다. 또한, 본 발명의 액정표시장치에 포함되는 그 외의 기타 구성의 종류 및 그 제조 방법도 특별히 한정되지 않으며, 이 분야의 일반적인 구성을 제한 없이 채용하여 사용할 수 있다.The type of liquid crystal cell constituting the liquid crystal display device of the present invention as described above is not particularly limited, such as TN (Twisted Neumatic), STN (Super Twisted Neumatic), IPS (In Plane Switching) or VA (Vertical Alignment) method It includes all common liquid crystal cells. In addition, the kind and other manufacturing method of the other structure contained in the liquid crystal display device of this invention are not specifically limited, either, The general structure of this field can be employ | adopted and used without a restriction | limiting.
이하, 본 발명에 따르는 실시예 및 본 발명에 따르지 않는 비교예를 통하여 본 발명을 보다 상세히 설명하나, 본 발명의 범위가 하기 제시된 실시예에 의해 제한되는 것은 아니다.Hereinafter, the present invention will be described in more detail through examples according to the present invention and comparative examples not according to the present invention, but the scope of the present invention is not limited to the examples given below.
제조예 1. 관능기 함유 아크릴계 공중합체(a1)의 제조Preparation Example 1. Preparation of functional group-containing acrylic copolymer (a1)
질소 가스가 환류되고, 온도 조절이 용이하도록 냉각장치를 설치한 1L의 반응기에 2-에틸헥실 아크릴레이트(2-EHA) 97 중량부 및 2-히드록시부틸 아크릴레이트(2-HBA) 3 중량부를 포함하는 단량체 혼합물을 투입하고, 용제로서 에틸아세테이트(EAc) 100 중량부를 투입하였다. 이어서, 산소 제거를 위해 질소 가스를 60분 동안 퍼징(purging)한 후, 온도를 70℃로 유지하였다. 반응기 내의 혼합물을 균일하게 한 후, 반응 개시제로서 2,2'-아조비스(2-메틸부티로니트릴)(Wako, V-59) 0.1 중량부를 투입하여 반응을 개시시켰다. 반응을 6시간 동안 진행한 다음, 에틸아세테이트로 희석하여 고형분 함량이 44%이고, 중량평균분자량이 50만이며, 분자량 분포가 7.0인 아크릴계 공중합체(a1)를 제조하였다.97 parts by weight of 2-ethylhexyl acrylate (2-EHA) and 3 parts by weight of 2-hydroxybutyl acrylate (2-HBA) in a 1-liter reactor equipped with a refrigeration system for nitrogen gas reflux and easy temperature control. The monomer mixture included was added, and 100 parts by weight of ethyl acetate (EAc) was added as a solvent. Subsequently, after purging with nitrogen gas for 60 minutes for oxygen removal, the temperature was maintained at 70 ° C. After the mixture in the reactor was uniform, 0.1 parts by weight of 2,2'-azobis (2-methylbutyronitrile) (Wako, V-59) was added as a reaction initiator to initiate the reaction. The reaction was carried out for 6 hours, and then diluted with ethyl acetate to prepare an acrylic copolymer (a1) having a solid content of 44%, a weight average molecular weight of 500,000, and a molecular weight distribution of 7.0.
제조예 2. 관능기 함유 아크릴계 공중합체(a2)의 제조 Preparation Example 2 Preparation of Functional Group-containing Acrylic Copolymer (a2)
2-히드록시부틸 아크릴레이트(2-HBA) 3 중량부 대신에 히드록시에틸 아크릴레이트(HEA) 3 중량부를 사용한 것을 제외하고는 제조예 1과 동일한 방식으로 아크릴계 공중합체(a2)를 제조하였다. An acrylic copolymer (a2) was prepared in the same manner as in Preparation Example 1, except that 3 parts by weight of hydroxyethyl acrylate (HEA) was used instead of 3 parts by weight of 2-hydroxybutyl acrylate (2-HBA).
제조예 3. 방사선 중합성기를 함유하는 베이스 수지(A1)의 제조 Preparation Example 3 Preparation of Base Resin (A1) Containing a Radiation Polymerizable Group
제조예 1에서 제조된 아크릴계 공중합체(a1) 100 중량부에 대하여, 방사선 중합성기 함유 화합물로서 메타크릴로일옥시 에틸 이소시아네이트 2 중량부 및 촉매로서 DBTDL(dibutyl tin Laurate) 0.015 중량부를 투입하고, 40℃에서 10 시간 동안 반응시켜, 측쇄에 방사선 중합성기가 도입된 아크릴계 공중합체(A1)를 제조하였다.To 100 parts by weight of the acrylic copolymer (a1) prepared in Preparation Example 1, 2 parts by weight of methacryloyloxy ethyl isocyanate as a radiation polymerizable group-containing compound and 0.015 part by weight of dibutyl tin Laurate (DBTDL) as a catalyst were added thereto. The reaction was carried out at 10 ° C. for 10 hours to prepare an acrylic copolymer (A1) having a radiation polymerizable group introduced into the side chain.
제조예 4. 방사선 중합성기를 함유하는 베이스 수지(A2)의 제조 Preparation Example 4 Preparation of Base Resin (A2) Containing a Radiation Polymerizable Group
제조예 2에서 제조된 아크릴계 공중합체(a2) 100 중량부에 대하여, 방사선 중합성기 함유 화합물로서 메타크릴로일옥시 에틸 이소시아네이트 2 중량부를 혼합하고, 40℃에서 10 시간 동안 반응시켜, 측쇄에 방사선 중합성기가 도입된 아크릴계 공중합체(A2)를 제조하였다.To 100 parts by weight of the acrylic copolymer (a2) prepared in Production Example 2, 2 parts by weight of methacryloyloxy ethyl isocyanate was mixed as a radiation polymerizable group-containing compound, reacted at 40 ° C. for 10 hours, and radiation polymerized to the side chain. An acryl-based copolymer (A2) into which a sexual group was introduced was prepared.
제조예 5. 방사선 중합성기를 함유하는 베이스 수지(A3)의 제조 Preparation Example 5 Preparation of Base Resin (A3) Containing a Radiation Polymerizable Group
메타크릴로일옥시 에틸 이소시아네이트 2 중량부 대신에 아크릴로일옥시 에틸 이소시아네이트 2 중량부를 사용한 것을 제외하고는 제조예 3과 동일한 방법으로 측쇄에 방사선 중합성기가 도입된 아크릴계 공중합체(A3)를 제조하였다An acrylic copolymer (A3) having a radiation polymerizable group introduced into the side chain was prepared in the same manner as in Preparation Example 3, except that 2 parts by weight of acryloyloxy ethyl isocyanate was used instead of 2 parts by weight of methacryloyloxy ethyl isocyanate.
제조예 6. 대전방지성 화합물의 제조Preparation Example 6 Preparation of Antistatic Compound
반응기 내에 중량평균분자량이 1,000인 폴리에틸렌글리콜 100 중량부를 투입 하고, 이어서 과염소산 리튬(LiClO4) 10 중량부 및 메틸 에틸케톤 500 ml를 혼합한 다음, 60℃ 내지 80℃의 반응 온도 범위 내에서 18 내지 20 시간 동안 반응을 진행시켜, 알칼리 금속 원자(Li)가 부가된 디올 화합물(b1)을 제조하였다.100 parts by weight of polyethylene glycol having a weight average molecular weight of 1,000 was added to the reactor, followed by mixing 10 parts by weight of lithium perchlorate (LiClO 4 ) and 500 ml of methyl ethyl ketone, and then 18 to 18 within a reaction temperature range of 60 ° C. to 80 ° C. The reaction was carried out for 20 hours to prepare a diol compound (b1) to which an alkali metal atom (Li) was added.
제조예 7. 방사선 중합성기 함유 대전방지성 화합물의 제조Preparation Example 7 Preparation of Antipolymerizable Compound Containing Radiation Polymeric Group
제조예 6에서 제조된 디올 화합물(b1) 100 중량부에 대하여, 방사선 중합성기 함유 화합물로서, 메타크릴로일옥시 에틸 이소시아네이트 2 중량부를 혼합하고, 40℃에서 10 시간 동안 반응시켜, 방사선 중합성기가 도입된 대전방지성 화합물(B1)을 제조하였다. To 100 parts by weight of the diol compound (b1) prepared in Production Example 6, as a compound containing a radiation polymerizable group, 2 parts by weight of methacryloyloxy ethyl isocyanate was mixed and reacted at 40 ° C. for 10 hours, whereby the radiation polymerizable group was added. The introduced antistatic compound (B1) was prepared.
실시예 1Example 1
제조예 3에서 제조된 아크릴계 공중합체(A1) 100 중량부에 대하여, 제조예 7에서 제조된 방사선 중합기 함유 대전 방지제(B1) 4 중량부, 다관능성 화합물로서, 디펜타에리쓰리톨 헥사아크릴레이트 10 중량부 및 광개시제로서 1-히드록시 시클로헥실페닐 케톤 2 중량부를 충분히 혼합하였다. 이어서, 배합액을 PET 필름에 코팅하고, 고압 수은 램프를 UV 광원으로 하여, 150 mJ/cm2의 광량, 600 mW/cm2의 조도로 방사선을 조사하여, 두께가 20 ㎛인 점착층을 포함하는 점착 필름을 제조하였다. To 100 parts by weight of the acrylic copolymer (A1) prepared in Production Example 3, 4 parts by weight of the radiation polymerizer-containing antistatic agent (B1) prepared in Production Example 7, as a polyfunctional compound, dipentaerythritol hexaacrylate 10 parts by weight and 2 parts by weight of 1-hydroxy cyclohexylphenyl ketone as a photoinitiator were sufficiently mixed. Subsequently, the compounding solution was coated on a PET film, and a high pressure mercury lamp was used as a UV light source to irradiate radiation with a light amount of 150 mJ / cm 2 and an illuminance of 600 mW / cm 2 to include an adhesive layer having a thickness of 20 μm. An adhesive film was prepared.
실시예 2. Example 2.
제조예 3의 아크릴계 공중합체(A1) 대신, 제조예 4의 아크릴계 공중합체(A2) 100 중량부를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 점착 필름을 제조하였다.An adhesive film was prepared in the same manner as in Example 1, except that 100 parts by weight of the acrylic copolymer (A2) of Preparation Example 4 were used instead of the acrylic copolymer (A1) of Preparation Example 3.
실시예 3. Example 3.
제조예 3의 아크릴계 공중합체(A1) 대신, 제조예 5의 아크릴계 공중합체(A3) 100 중량부를 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 점착 필름을 제조하였다.An adhesive film was prepared in the same manner as in Example 1, except that 100 parts by weight of the acrylic copolymer (A3) of Preparation Example 5 were used instead of the acrylic copolymer (A1) of Preparation Example 3.
비교예 1.Comparative Example 1
제조예 7의 대전방지성 화합물(B1) 대신에 제조예 6에서 제조된 금속원자가 부가된 디올 화합물(b1)을 사용한 것을 제외하고는, 실시예 1과 동일한 방법으로 점착 필름을 제조하였다.An adhesive film was prepared in the same manner as in Example 1 except for using the diol compound (b1) to which the metal atom prepared in Preparation Example 6 was added instead of the antistatic compound (B1) of Preparation Example 7.
상기 제조된 실시예 및 비교예의 점착 필름에 대하여, 하기 제시된 방법으로 물성을 평가하였다.The physical properties of the adhesive films of Examples and Comparative Examples prepared above were evaluated by the methods given below.
1. 저속 및 고속 박리력의 평가1. Evaluation of low speed and high speed peeling force
실시예 및 비교예에서 제조된 점착 필름을 편광판의 보호 필름(TAC, 일본 후 지필름(제)) 및 반사방지층(AG, 일본 DNP(제))의 면에 각각 2 Kg의 롤러를 사용하여 부착하였다. 이어서, 제조된 샘플을 23℃의 온도 및 50%의 상대습도 조건 하에서 24 시간 동안 보관한 다음, 인장 시험기를 사용하여, 180도의 각도에서 0.3 m/min(저속 박리력) 및 30 m/min(고속 박리력)의 박리 속도로 박리력을 측정하였다.The pressure-sensitive adhesive films prepared in Examples and Comparative Examples were attached to the surfaces of the protective film (TAC, Japan Fujifilm (manufactured)) and the antireflection layer (AG, Japan DNP (manufactured)) of the polarizing plate using 2 kg rollers, respectively. It was. The prepared sample was then stored for 24 hours under a temperature of 23 ° C. and 50% relative humidity conditions, then using a tensile tester, 0.3 m / min (low speed peel force) and 30 m / min (at 180 degrees) Peeling force was measured at the peeling speed of (high speed peeling force).
또한, 경시적인 물성 변화를 측정하기 위하여, 상기와 같은 저속 및 고속 박리력은, 제조된 샘플을 50℃의 온도에서 5일 동안 보관한 후에 동일하게 측정하였다.In addition, in order to measure the change in physical properties over time, the low-speed and high-speed peeling force as described above, the same was measured after storing the prepared sample at a temperature of 50 ℃ for 5 days.
2. 정전압 평가 2. Constant voltage evaluation
실시예 및 비교예에서 제조된 점착 필름을 부착한 편광판을 25 cm×22 cm의 크기로 재단하여 시료를 제작하였다. 제작된 시료를 23℃의 온도 및 50%의 상대 습도 조건 하에서 24 시간 동안 보관한 다음, 시료에서 점착 필름을 40 m/min의 속도로 박리하는 과정에서 발생하는 정전압을 편광판 표면으로부터 1 cm의 높이에서 정전압 측정기(STATRION-M2)를 이용하여 측정하였다. Samples were prepared by cutting a polarizing plate with a pressure-sensitive adhesive film prepared in Examples and Comparative Examples to a size of 25 cm x 22 cm. The fabricated sample was stored at 23 ° C. and 50% relative humidity for 24 hours, and then the constant voltage generated in the process of peeling off the adhesive film at a rate of 40 m / min from the sample was 1 cm high from the surface of the polarizing plate. Was measured using a constant voltage meter (STATRION-M2).
또한, 경시적인 물성 변화를 측정하기 위하여, 상기와 같은 정전압을 제조된 시료를 50℃의 온도에서 5일 동안 보관한 후에 동일하게 측정하였다.In addition, in order to measure the change in physical properties over time, the same constant voltage was measured after storing the prepared sample for 5 days at a temperature of 50 ℃.
상기 각각의 정전압 측정은 2회 반복하여 수행하여 그 결과값을 각각 기재하였다. Each of the constant voltage measurements was performed twice, and the results were described, respectively.
상기와 같이 측정한 결과를 하기 표 1에 정리하여 기재하였다.The results measured as described above are summarized in Table 1 below.
[표 1][Table 1]
(gf)Peeling force
(gf)
(gf)High speed peeling force
(gf)
(gf)Peeling force
(gf)
(gf)High speed peeling force
(gf)
상기 표 1로부터 알 수 있는 바와 같이, 본 발명에 따른 실시예 1 내지 3의 경우, 우수한 박리 특성 및 대전 방지 특성을 나타내는 동시에, 대전 방지 성분이 주사슬 내에 직접 결합되어 존재하는 등의 이유로 경시적으로도 상기 물성이 안정적으로 유지됨을 확인할 수 있었다. 반면, 비교예 1의 경우, 열악한 박리 특성 및 대전방지특성을 나타낼 뿐만 아니라, 경시적으로 그 물성이 더욱 악화되는 것을 확인할 수 있었다.As can be seen from Table 1, Examples 1 to 3 according to the present invention show excellent peeling properties and antistatic properties, and at the same time, due to the presence of antistatic components directly bonded to the main chain. Also it could be confirmed that the physical properties are maintained stably. On the other hand, in the case of Comparative Example 1, not only showed poor peeling properties and antistatic properties, it was confirmed that the physical properties deteriorated over time.
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