KR20230145987A - Coating composition and film manufactured therefrom - Google Patents
Coating composition and film manufactured therefrom Download PDFInfo
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- KR20230145987A KR20230145987A KR1020230134116A KR20230134116A KR20230145987A KR 20230145987 A KR20230145987 A KR 20230145987A KR 1020230134116 A KR1020230134116 A KR 1020230134116A KR 20230134116 A KR20230134116 A KR 20230134116A KR 20230145987 A KR20230145987 A KR 20230145987A
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- KR
- South Korea
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- weight
- parts
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- silsesquioxane
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- 239000008199 coating composition Substances 0.000 title claims abstract description 34
- 230000035699 permeability Effects 0.000 claims abstract description 40
- 229920002284 Cellulose triacetate Polymers 0.000 claims abstract description 35
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 claims abstract description 35
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 15
- 239000003999 initiator Substances 0.000 claims description 10
- 239000011347 resin Substances 0.000 claims description 10
- 229920005989 resin Polymers 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000003700 epoxy group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 239000006096 absorbing agent Substances 0.000 claims description 3
- 125000002091 cationic group Chemical group 0.000 claims description 3
- 125000005647 linker group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 2
- 125000002560 nitrile group Chemical group 0.000 claims description 2
- 125000002704 decyl 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])* 0.000 claims 1
- 230000000475 sunscreen effect Effects 0.000 claims 1
- 239000000516 sunscreening agent Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract description 24
- 230000003287 optical effect Effects 0.000 abstract description 7
- 239000010408 film Substances 0.000 description 67
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
- 239000003054 catalyst Substances 0.000 description 32
- 239000000654 additive Substances 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 27
- 230000000996 additive effect Effects 0.000 description 26
- 230000015572 biosynthetic process Effects 0.000 description 26
- 238000003786 synthesis reaction Methods 0.000 description 26
- 239000000203 mixture Substances 0.000 description 23
- 230000000052 comparative effect Effects 0.000 description 21
- 239000011342 resin composition Substances 0.000 description 20
- 239000011248 coating agent Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000001816 cooling Methods 0.000 description 15
- 239000012153 distilled water Substances 0.000 description 15
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 15
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 15
- 239000010931 gold Substances 0.000 description 15
- 229910052737 gold Inorganic materials 0.000 description 15
- 239000012535 impurity Substances 0.000 description 15
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 15
- 229920001296 polysiloxane Polymers 0.000 description 14
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 11
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 11
- 238000001035 drying Methods 0.000 description 11
- IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 10
- 230000001678 irradiating effect Effects 0.000 description 9
- 239000010410 layer Substances 0.000 description 8
- 239000004372 Polyvinyl alcohol Substances 0.000 description 5
- 239000011247 coating layer Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229920002451 polyvinyl alcohol Polymers 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012788 optical film Substances 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 239000004695 Polyether sulfone Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000002390 adhesive tape Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000012994 photoredox catalyst Substances 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000004823 Reactive adhesive Substances 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- -1 acronitrile Chemical compound 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/043—Improving the adhesiveness of the coatings per se, e.g. forming primers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/046—Forming abrasion-resistant coatings; Forming surface-hardening coatings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
- C08L1/08—Cellulose derivatives
- C08L1/10—Esters of organic acids, i.e. acylates
- C08L1/12—Cellulose acetate
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Paints Or Removers (AREA)
- Laminated Bodies (AREA)
- Polarising Elements (AREA)
- Silicon Polymers (AREA)
Abstract
본 발명은 코팅 조성물에 관한 것으로서, 특히 간단한 코팅 공정만으로 트리아세틸 셀룰로오스 필름의 광학적 물성을 해치지 않으면서, 내투습성 및 표면경도를 현저히 개선할 수 있는 코팅 조성물에 관한 것이다.The present invention relates to a coating composition, and in particular, to a coating composition that can significantly improve the moisture permeability resistance and surface hardness of a triacetyl cellulose film without damaging the optical properties of the triacetyl cellulose film through a simple coating process.
Description
본 발명은 코팅 조성물에 관한 것으로서, 특히 트리아세틸 셀룰로오스 필름 위에 코팅 조성물을 이용하여 간단한 코팅 공정만으로 트리아세틸 셀룰로오스 필름의 광학적 물성을 해치지 않으면서, 내투습성 및 표면경도를 개선할 수 있는 코팅 조성물에 관한 것이다.The present invention relates to a coating composition, and in particular, to a coating composition that can improve moisture permeability resistance and surface hardness without damaging the optical properties of the triacetyl cellulose film through a simple coating process using the coating composition on a triacetyl cellulose film. will be.
이하에 기술되는 내용은 단순히 본 발명과 관련되는 배경 정보만을 제공할 뿐 종래기술을 구성하는 것이 아니다.The content described below simply provides background information related to the present invention and does not constitute prior art.
트리아세틸 셀룰로오스 필름은 사진 필름으로 반세기 이상 사용되어 온 천연소재 플라스틱 필름이며, 독특한 비정질 구조를 갖고 있어서 그로 인해 독특한 기계적, 광학적 물성을 발현한다. 특히 복굴절이 매우 낮은 수준으로 광학적 등방성이 뛰어난 특성을 갖는다. 이러한 특성을 바탕으로 트리아세틸 셀룰로오스 필름은 편광판용 보호필름, 시야각 확대 필름의 지지체 등의 광학필름 용으로 널리 사용되고 있다. 특히 편광판용 보호필름으로 사용되는 트리아세틸 셀룰로오스 필름은 순도가 높고 투명성과 광학적 등방성이 양호하여 위상차가 없어 폴리비닐알콜 필름의 양면에 접착하여 강도를 향상하고 폴리비닐알콜 기재를 열이나 습도로부터 보호하는 역할을 한다. 또한, 폴리비닐알콜 기재와 트리아세틸 셀룰로오스 필름을 접착시킬 때 수용성 접착제를 이용하므로, 이에 이용되는 트리아세틸 세룰로오스 필름은 접착 이후 수분이 빠져나갈 수 있도록 적절한 투습 특성이 필수적으로 요구되었다. 그러나 최근의 편광판 제작 동향을 살펴보면, 기존의 수계 접착제를 이용하던 것이, 반응성 접착제로 급격히 변화되고 있어 더 이상 트리아세틸 셀룰로오스 필름의 투습 특성이 필요치 않도록 공정과정 또한 함께 변화되고 있다.Triacetyl cellulose film is a natural plastic film that has been used as a photographic film for more than half a century. It has a unique amorphous structure, resulting in unique mechanical and optical properties. In particular, it has excellent optical isotropy with very low birefringence. Based on these characteristics, triacetyl cellulose film is widely used for optical films such as protective films for polarizers and supports for viewing angle expansion films. In particular, the triacetyl cellulose film used as a protective film for polarizers has high purity and good transparency and optical isotropy, so there is no phase difference, so it is bonded to both sides of the polyvinyl alcohol film to improve strength and protect the polyvinyl alcohol substrate from heat and humidity. It plays a role. In addition, since a water-soluble adhesive is used when bonding a polyvinyl alcohol substrate and a triacetyl cellulose film, the triacetyl cellulose film used for this was essentially required to have appropriate moisture permeability characteristics to allow moisture to escape after bonding. However, looking at recent trends in polarizer production, the use of existing water-based adhesives is rapidly changing to reactive adhesives, and the process is also changing so that the moisture permeability characteristics of the triacetyl cellulose film are no longer required.
또한, 트리아세틸 셀룰오로스 필름은 수분투과도가 타 필름 류에 비해 높은 편으로 고온, 다습한 환경에서는 내구성이 저하되기 쉬워 편광자의 불량을 야기시키며, 스크래치에 취약한 표면의 경도는 해결되어야 하는 궁극의 과제로 지적되고 있다.In addition, triacetyl cellulose film has a higher moisture permeability than other films, and its durability is easily reduced in high temperature and high humidity environments, causing defects in the polarizer, and the hardness of the surface, which is vulnerable to scratches, is the ultimate problem that must be solved. It is pointed out as a challenge.
위와 같은 문제점을 극복하고자 산업계에서는 많은 시도들이 이어져 왔다. 예를 들어 한국공개특허 10-2016-0080656호에서는 트리아세틸 셀룰로오스 필름 위에 실록산올리고머를 포함한 코팅층을 형성하여 트리아세틸 셀룰로오스 필름의 투습도 및 표면경도를 극복하려고 하였다. 그러나, 상기 기술들에는 표면경도가 3H의 한계를 보이며, 높은 투습율을 나타내어 내구성이 떨어지는 문제점이 여전히 존재하였다.Many attempts have been made in the industry to overcome the above problems. For example, in Korean Patent Publication No. 10-2016-0080656, an attempt was made to overcome the moisture permeability and surface hardness of the triacetyl cellulose film by forming a coating layer containing a siloxane oligomer on the triacetyl cellulose film. However, the above technologies still had the problem of limited surface hardness of 3H and low durability due to high moisture permeability.
상기와 같은 종래기술의 문제점을 해결하고자, 본 발명은 간단한 코팅 공정만으로 필름의 광학적 물성을 해치지 않으면서, 내투습성 및 표면경도를 현저히 개선할 수 있는 코팅 조성물을 제공하는 것을 목적으로 한다.In order to solve the problems of the prior art as described above, the purpose of the present invention is to provide a coating composition that can significantly improve moisture permeability resistance and surface hardness without damaging the optical properties of the film through a simple coating process.
또한 본 발명은 상기 코팅 조성물을 이용하여 투습성 및 표면경도가 향상된 필름 및 이를 포함하는 광학필름을 제공하는 것을 목적으로 한다.Another object of the present invention is to provide a film with improved moisture permeability and surface hardness using the coating composition and an optical film containing the same.
상기 목적을 달성하기 위하여 본 발명은 In order to achieve the above object, the present invention
케이지형실세스퀴옥산 수지와 레더형실세스퀴옥산 수지의 중량비가 10 중량% : 90 중량% 내지 80 중량% : 20 중량%인 실세스퀴옥산올리고머를 포함하는 코팅 조성물을 제공한다.Provided is a coating composition comprising a silsesquioxane oligomer in which the weight ratio of the cage-type silsesquioxane resin and the leather-type silsesquioxane resin is 10% by weight: 90% by weight to 80% by weight: 20% by weight.
또한 본 발명은 코팅 조성물이 기재 상에 코팅되어 경화된 필름을 제공한다.The present invention also provides a film in which the coating composition is coated on a substrate and cured.
본 발명에 따른 코팅 조성물은 간단한 코팅 공정만으로 필름의 우수한 광학적 물성을 해치지 않으면서, 내투습성 및 표면경도를 개선할 수 있다. The coating composition according to the present invention can improve moisture permeability resistance and surface hardness without damaging the excellent optical properties of the film through a simple coating process.
도 1은 본 발명의 일 실시예에 따른 코팅된 필름을 나타낸 도면이며, 코팅층은 실제보다 두껍게 표시되어 있다.
도 2는 본 발명의 일 실시예에 따른 하드코팅된 트리아세틸 셀룰로오스 필름의 결합구조를 나타낸 도면이다.
도 3은 본 발명의 실시예 1에 따른 코팅된 트리아세틸 셀룰로오스 필름의 코팅단면 SEM 사진이다.Figure 1 is a diagram showing a coated film according to an embodiment of the present invention, and the coating layer is shown to be thicker than it actually is.
Figure 2 is a diagram showing the bonding structure of a hard-coated triacetyl cellulose film according to an embodiment of the present invention.
Figure 3 is a cross-sectional SEM photograph of the coated triacetyl cellulose film according to Example 1 of the present invention.
아래에서는 첨부한 도면을 참고로 하여 본 발명의 실시예에 대하여 본 발명이 속하는 기술 분야에서 통상의 지식을 가진 자가 용이하게 실시할 수 있도록 상세히 설명한다. 그러나 본 발명은 여러 가지 상이한 형태로 구현될 수 있으며 여기에서 설명하는 실시예에 한정되지 않는다. Below, with reference to the attached drawings, embodiments of the present invention will be described in detail so that those skilled in the art can easily implement the present invention. However, the present invention may be implemented in many different forms and is not limited to the embodiments described herein.
명세서 전체에서, 어떤 부분이 어떤 구성요소를 "포함"한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성요소를 더 포함할 수 있는 것을 의미한다.Throughout the specification, when a part is said to “include” a certain element, this means that it may further include other elements rather than excluding other elements, unless specifically stated to the contrary.
본 발명의 코팅조성물은 케이지형실세스퀴옥산 수지와 레더형실세스퀴옥산 수지의 중량비가 10 중량% : 90 중량% 내지 80 중량% : 20 중량%인 실세스퀴옥산올리고머를 포함한다.The coating composition of the present invention includes a silsesquioxane oligomer in which the weight ratio of the cage-type silsesquioxane resin and the leather-type silsesquioxane resin is 10% by weight: 90% by weight to 80% by weight: 20% by weight.
구체적으로 본 발명의 코팅 조성물은 상기 실세스퀴옥산올리고머; 개시제; 및 용매를 포함할 수 있다.Specifically, the coating composition of the present invention includes the silsesquioxane oligomer; initiator; and a solvent.
상기 실세스퀴옥산올리고머는 케이지 구조와 레더 구조를 함께 가질 수 있으며, 구체적으로 화학식 1로 표시되는 레더형실세스퀴옥산 수지에 화학식 2로 표시되는 케이지형실세스퀴옥산 수지가 결합된 것일 수 있다.The silsesquioxane oligomer may have both a cage structure and a leather structure, and specifically, it may be a leather-type silsesquioxane resin represented by Formula 1 combined with a cage-type silsesquioxane resin represented by Formula 2. .
상기 화학식 1에서,In Formula 1,
R1, R2, R3, R4는 각각 독립적으로 치환기로 치환되거나 치환되지 않은 메틸기; 페닐기; 아미노기; (메타)아크릴기; 비닐기; 에폭시기; 사이올기; 또는 자외선흡수체이며, n은 1 내지 100의 정수이고,R 1 , R 2 , R 3 , and R 4 are each independently a methyl group substituted or unsubstituted with a substituent; phenyl group; amino group; (meth)acrylic group; vinyl group; epoxy group; Cyol group; or an ultraviolet ray absorber, n is an integer from 1 to 100,
R5, R6, R7, R8은 각각 독립적으로, 수소; 치환기로 치환되거나 치환되지 않은 C1~C10의 알킬기; 또는 하기 화학식 2로 표시되는 연결기이며, R5, R6, R7, R8 중 적어도 하나는 하기 화학식 2와 연결되며,R 5 , R 6 , R 7 , and R 8 are each independently hydrogen; C 1 to C 10 alkyl group substituted or unsubstituted with a substituent; Or it is a linking group represented by the following formula (2), and at least one of R 5 , R 6 , R 7 , and R 8 is connected to the following formula (2),
상기 화학식 2에서,In Formula 2,
R은 각각 독립적으로 치환기로 치환되거나 치환되지 않은 메틸기, 페닐기, 아미노기, (메타)아크릴기, 비닐기, 에폭시기, 사이올기 또는 자외선흡수제이며, R0은 각각 독립적으로 수소 또는 치환기로 치환되거나 치환되지 않은 C1~C10의 알킬기이며,R is each independently a methyl group, phenyl group, amino group, (meth)acrylic group, vinyl group, epoxy group, thiol group, or ultraviolet absorber, which is independently substituted or unsubstituted with a substituent, and R 0 is each independently hydrogen or unsubstituted with a substituent. It is an alkyl group of C 1 to C 10 ,
n은 3 내지 6의 정수이며,n is an integer from 3 to 6,
상기 화학식 1 또는 2에서 치환기는 각각 독립적으로 중수소, 할로겐, 아민기, 에폭시기, (메타)아크릴기, 사이올기, 이소시아네이트기, 니트릴기, 니트로기 또는 페닐기이다.In Formula 1 or 2, the substituents are each independently deuterium, halogen, amine group, epoxy group, (meth)acrylic group, thiol group, isocyanate group, nitrile group, nitro group, or phenyl group.
상기 자외선 흡수체는 200 ㎚ 내지 400 ㎚의 파장 범위를 갖는 자외선을 흡수하는 구조체이며, 범용적으로 사용되어지고 있는 자외선흡수체로는 benzophenone계(자외선 흡수범위 300~380nm), benzotriazole계(흡수범위 300 ~385nm), salicylic acid계(흡수범위 260~340nm), acrylonitrile계(흡수범위 290~400nm) 등이 있다.The ultraviolet absorber is a structure that absorbs ultraviolet rays with a wavelength range of 200 nm to 400 nm. Commonly used ultraviolet absorbers include benzophenone series (ultraviolet absorption range 300~380 nm) and benzotriazole series (absorption range 300 ~ 380 nm). 385nm), salicylic acid type (absorption range 260~340nm), and acrylonitrile type (absorption range 290~400nm).
본 발명에 사용되는 상기 실세스퀴옥산올리고머는 올리고머 내의 케이지 구조의 비율이 10 내지 80 중량%를 가짐으로써 TAC 필름의 수분투과도는 100 g/m2.day이하인 우수한 내투습성을 만족시킬 수 있으며, 구체적으로 실세스퀴옥산올리고머는 올리고머 내의 케이지 구조의 비율이 20 내지 50 중량%를 가짐으로써 TAC 필름의 수분투과도는 85 g/m2.day이하인 우수한 내투습성 및 동시에 만족시킬 수 있으며, 더욱 구체적으로 실세스퀴옥산올리고머는 올리고머 내의 케이지 구조의 비율이 25 내지 35 중량%를 가짐으로써 TAC 필름의 수분투과도는 70 g/m2.day이하인 우수한 내투습성 만족시킬 수 있다.The silsesquioxane oligomer used in the present invention has a cage structure ratio of 10 to 80% by weight in the oligomer, so that the moisture permeability of the TAC film can satisfy excellent moisture permeability resistance of 100 g/m 2.day or less, Specifically, the silsesquioxane oligomer has a cage structure ratio of 20 to 50% by weight in the oligomer, so that the moisture permeability of the TAC film can be satisfied at the same time as excellent moisture permeability resistance of 85 g/m 2.day or less. The silsesquioxane oligomer has a cage structure ratio of 25 to 35% by weight in the oligomer, so that the moisture permeability of the TAC film can satisfy excellent moisture permeability resistance of 70 g/m 2 .day or less.
또한 구체적으로 화학식 2로 표시되는 연결기는 n이 4인 경우 하기 화학식 3과 같은 구조일 수 있다.Additionally, specifically, the linking group represented by Formula 2 may have a structure as shown in Formula 3 below when n is 4.
상기 화학식 3에서 *는 연결부위이며, R 및 R0는 화학식 2에서 정의한 바와 같다.In Formula 3, * is a connection site, and R and R 0 are as defined in Formula 2.
본 발명의 코팅 조성물에서 상기 실세스퀴옥산올리고머의 함량은 20 내지 60 중량%인 것이 좋다. 상기 범위 내인 경우 TAC 필름의 우수한 내투습성 및 우수한 표면경도를 동시에 만족시킬 수 있다.In the coating composition of the present invention, the content of the silsesquioxane oligomer is preferably 20 to 60% by weight. If it is within the above range, the excellent moisture permeability resistance and excellent surface hardness of the TAC film can be simultaneously satisfied.
트리아세틸 셀룰로오스 필름은 높은 수분투과도로 인하여 다습한 환경에서는 내구성이 저하되기 쉬우며, 특히 이를 이용한 편광판의 편광자의 불량을 야기시키는 원인이 된다. 이에 본 발명에서는 트리아세틸 셀룰로오스 필름 위에 실세스퀴옥산을 포함한 조성물을 코팅함으로써 트리아세틸 셀룰로오스 필름의 수분투과도를 현저하게 낮추면서 표면경도 또한 월등히 향상시켜 내구성이 향상된 트리아세틸 셀룰로오스 필름을 제공하는 것이다. Due to the high moisture permeability of the triacetyl cellulose film, the durability is easily reduced in a humid environment, and in particular, it causes defects in the polarizer of the polarizing plate using it. Accordingly, the present invention provides a triacetyl cellulose film with improved durability by coating a composition containing silsesquioxane on a triacetyl cellulose film, thereby significantly lowering the moisture permeability of the triacetyl cellulose film and significantly improving surface hardness.
레더형 단독의 실세스퀴옥산은 취성이 높아, 코팅 시에 코팅막이 갈라지며 부서지기 쉬워 코팅막으로는 용이하지 못하다. 또한 케이지형 단독의 실세스퀴옥산은 코팅 후 시간이 지남에 따라서 재배열을 일으켜 초기의 성능을 유지하지 못하며, 케이지 구조자체가 갖는 공극으로 인하여 투습율을 저하시키는 것에 한계가 있다.Leather-type silsesquioxane alone is highly brittle, and the coating film cracks and breaks easily during coating, making it difficult to use as a coating film. In addition, cage-type silsesquioxane does not maintain initial performance due to rearrangement over time after coating, and has limitations in reducing moisture permeability due to the pores of the cage structure itself.
이에, 본 발명자들은 한 분자내 케이지형 구조와 레더형 구조를 동시에 갖는 실세스퀴옥산을 제조하였다. 또한 케이지형 구조와 레더형 구조의 비율을 조절함으로써 투습율 및 표면경도를 향상시켰다. 특히 케이지형 구조와 레더형 구조의 비율이 10 중량% : 90 중량% 내지 80 중량% : 20 중량%을 갖는 코팅 조성물을 코팅 시에 형성 된 네트워크 구조사이의 공극의 크기를 줄여 투습율을 현저하게 저하시켰으며, 표면경도 또한 월등히 향상시켰다.Accordingly, the present inventors prepared silsesquioxane, which has both a cage-like structure and a leather-like structure within one molecule. In addition, moisture permeability and surface hardness were improved by adjusting the ratio of the cage-type structure and the leather-type structure. In particular, the moisture permeability rate is significantly reduced by reducing the size of the voids between the network structures formed when coating a coating composition having a ratio of cage-type structure and leather-type structure of 10% by weight: 90% by weight to 80% by weight: 20% by weight. decreased, and surface hardness was also significantly improved.
또한 본 발명의 코팅 조성물에 포함되는 개시제는 특별히 한정되지 않으며, 구체적으로 광 라디칼개시제, 광 양이온 개시제, 열 라디칼개시제 또는 열 양이온 개시제 등을 사용할 수 있다. 본 발명의 코팅 조성물에서 상기 개시제의 함량은 0.1 내지 10 중량%인 것이 좋다. 상기 범위 내인 경우 TAC 필름의 우수한 내투습성 및 우수한 표면경도를 동시에 만족시킬 수 있다.Additionally, the initiator included in the coating composition of the present invention is not particularly limited, and specifically, a photo radical initiator, a photo cationic initiator, a thermal radical initiator, or a thermal cationic initiator may be used. The content of the initiator in the coating composition of the present invention is preferably 0.1 to 10% by weight. If it is within the above range, the excellent moisture permeability resistance and excellent surface hardness of the TAC film can be simultaneously satisfied.
또한 본 발명에서 사용 가능한 용매는 용해성이 있으며 반응에 영향을 미치지 않는 용매라면 특별히 한정되지 않으며, 구체적으로는 상기 유기용매로는 알코올류, 케톤류, 글리콜류, 퓨란계, 디메틸포름아미드, 디메틸아세트아미드, N-메틸-2-피롤리돈 등의 극성용매 뿐 아니라, 헥산, 사이클로헥산, 사이클로헥사논, 톨루엔, 자일렌, 크레졸, 클로로포름, 디클로로벤젠, 디메틸벤젠, 트리메틸벤젠, 피리딘, 메틸나프탈렌, 니트로메탄, 아크로니트릴, 메틸렌클로라이드, 옥타데실아민, 아닐린, 디메틸설폭사이드, 벤질알콜 등 다양한 용매를 이용할 수 있으나, 이에 제한되지는 않는다. 본 발명에서 상기 용매는 실세스퀴옥산올리고머, 개시제 및 선택적으로 추가되는 첨가제를 제외한 잔량으로 포함될 수 있다.In addition, the solvent usable in the present invention is not particularly limited as long as it is soluble and does not affect the reaction. Specifically, the organic solvents include alcohols, ketones, glycols, furans, dimethylformamide, and dimethylacetamide. , N-methyl-2-pyrrolidone, as well as polar solvents such as hexane, cyclohexane, cyclohexanone, toluene, xylene, cresol, chloroform, dichlorobenzene, dimethylbenzene, trimethylbenzene, pyridine, methylnaphthalene, nitro Various solvents such as methane, acronitrile, methylene chloride, octadecylamine, aniline, dimethyl sulfoxide, and benzyl alcohol can be used, but are not limited thereto. In the present invention, the solvent may be included in the remaining amount excluding the silsesquioxane oligomer, initiator, and optionally added additives.
본 발명의 코팅 조성물은 필요에 따라 실리콘계 첨가제 또는 아크릴계 첨가제를 더욱 포함할 수 있다.The coating composition of the present invention may further include a silicone-based additive or an acrylic-based additive, if necessary.
상기 코팅 조성물의 실리콘계 첨가제는 BYK-300, BYK-301, BYK-302, BYK-331, BYK-335, BYK-306, BYK-330, BYK-341, BYK-344, BYK-307, BYK-333, BYK-310가 있으며, 아크릴계 첨가제는 BYK-340, BYK-350, BYK-352, BYK-354, BYK-355, BYK-356, BYK-358N, BYK-359, BYK-361N, BYK-380N, BYK-381, BYK-388, BYK-390, BYK-392, BYK-394가 있다. 상기 첨가제는 각각 독립적으로 0.01 내지 5 중량%의 함량으로 첨가될 수 있다. 상기 실리콘계 첨가제를 포함할 경우 하드코팅층의 표면슬립성과 코팅의 평탄성을 더욱 향상시킬 수 있으며, 내투습성을 더욱 향상시킬 수 있다. 또한 아크릴계 첨가제를 사용할 경우 하드코팅층의 레벨링성 및 내투습성을 더욱 향상시킬 수 있다. 또한 본 발명의 하드코팅 조성물은 필요에 따라 산화방지제, 레벨링제 등 하드코팅 조성물에 첨가될 수 있는 공지의 첨가제를 더욱 포함할 수 있다.The silicone-based additive of the coating composition is BYK-300, BYK-301, BYK-302, BYK-331, BYK-335, BYK-306, BYK-330, BYK-341, BYK-344, BYK-307, BYK-333. , BYK-310, and acrylic additives include BYK-340, BYK-350, BYK-352, BYK-354, BYK-355, BYK-356, BYK-358N, BYK-359, BYK-361N, BYK-380N, There are BYK-381, BYK-388, BYK-390, BYK-392, and BYK-394. The above additives may each independently be added in an amount of 0.01 to 5% by weight. When the silicone-based additive is included, the surface slippage of the hard coating layer and the flatness of the coating can be further improved, and moisture permeability resistance can be further improved. Additionally, when an acrylic additive is used, the leveling properties and moisture permeability resistance of the hard coating layer can be further improved. In addition, the hard coating composition of the present invention may further include known additives that can be added to the hard coating composition, such as antioxidants and leveling agents, if necessary.
또한 본 발명은 상기 코팅 조성물이 기재 상에 코팅되어 경화된 필름을 제공한다.Additionally, the present invention provides a film in which the coating composition is coated on a substrate and cured.
본 발명에 따른 코팅 조성물은 4 g/m2.day이상의 수분투과도를 갖는 필름에서 내투습성을 향상시키는 효과를 가져온다. 자세하게, 상기 코팅 조성물은 PMMA, PET, PC, PES, PVA, PI, COC 등의 필름에 코팅 가능하며, 특히, 트리아세틸 셀룰로오스 필름에 코팅하였을 경우, 투습력 향상의 효과가 가장 효과적으로 일어난다.The coating composition according to the present invention has the effect of improving moisture permeability resistance in films having a moisture permeability of 4 g/m 2 .day or more. In detail, the coating composition can be coated on films such as PMMA, PET, PC, PES, PVA, PI, COC, etc. In particular, when coated on a triacetyl cellulose film, the effect of improving moisture permeability occurs most effectively.
도 1은 본 발명의 일 실시예에 따른 코팅된 필름(100)을 나타낸 것이다.Figure 1 shows a
본 발명의 코팅된 필름(100)은 필름층(101) 위에 상기 코팅 조성물의 경화층(102)이 결합된 구조를 가진다. 구체적으로 상기 코팅 조성물의 경화층(102)의 두께는 10 내지 60 um일 수 있다. 상기 필름은 PMMA, PET, PC, PES, PVA, PI, COC 등의 필름일 수 있으며, 특히, 트리아세틸 셀룰로오스 필름일 수 있다. 상기 범위 내인 경우 코팅된 필름(100)의 내투습성과 표면경도를 더욱 향상시킬 수 있다. The
상기 코팅 조성물의 경화층(102)를 형성하는 방법은 상기 코팅 조성물을 필름층(101) 표면 위에 코팅한 후 건조 또는 경화시켜 형성할 수 있으며, 코팅방법은 스핀코팅, 바코팅, 슬릿코팅, 딥 코팅, 내츄럴 코팅, 리버스 코팅, 롤 코팅, 스핀코팅, 커텐코팅, 스프레이 코팅, 침지법, 함침법, 그라비어 코팅 등 공지된 방법 중에서 당업자가 임의로 선택하여 적용할 수 있다.The method of forming the cured
구체적으로 상기 코팅 조성물의 경화층(102)은 실리콘계 첨가제 및 아크릴계 첨가제를 더욱 포함할 수 있으며, 이 경우 코팅된 필름(100)의 내투습성과 표면경도를 더욱 향상시킬 수 있다.Specifically, the cured
도 2는 본 발명의 코팅된 트리아세틸 셀룰로오스 필름(100)의 코팅단면의 결합구조를 나타낸 것이다. 도 2에 나타나는 바와 같이 필름층(101)과 코팅 조성물의 경화층(102)이 수소결합 및/또는 반데르발스 결합을 통하여 강하게 결합됨으로써 전체 코팅된 트리아세틸 셀룰로오스 필름(100)이 내투습성과 표면경도에 내구성이 뛰어난 장점이 있다.Figure 2 shows the bonding structure of the coated cross section of the coated
본 발명에 따른 코팅된 필름(100)은 종래 필름의 고질적 문제인 내투습성 및 표면경도를 현저히 개선하여 편광판용 보호필름, 시야각확대 필름의 지지체 등 광학필름에 유용하게 적용할 수 있다. The
이하, 본 발명의 이해를 돕기 위하여 구체적인 실시예를 제시하나, 하기 실시예는 본 발명을 예시하는 것일 뿐 본 발명의 범위가 하기 실시예에 한정되는 것은 아니다.Hereinafter, specific examples will be presented to aid understanding of the present invention. However, the following examples are merely illustrative of the present invention and the scope of the present invention is not limited to the following examples.
[촉매 제조][Catalyst manufacturing]
염기도 조절을 위하여, 테트라메틸암모늄하이드록사이드 25 중량% 수용액에 10% 포타슘하이드록사이드 수용액을 혼합하여 촉매를 제조하였다.To control basicity, a catalyst was prepared by mixing a 25% by weight aqueous solution of tetramethylammonium hydroxide with a 10% aqueous potassium hydroxide solution.
[합성예 1][Synthesis Example 1]
냉각관과 교반기를 구비한 건조된 플라스크에, 증류수 10 중량부, 아세토니트릴(대정화금) 20중량부, 제조된 촉매 2 중량부를 적가하고, 1시간 동안 상온에서 교반한 후, 2-(3,4 에폭시사이클로헥실) 에틸트리메톡시실란(신에츠, 상품명 KBM-303) 20 중량부를 적가하여 6시간을 추가 교반하였다. 반응 완료 후 두 차례 세정하여 촉매와 불순물을 추출하였으며, 최종적으로 케이지형실세스퀴옥산 및 레더형실세스퀴옥산이 10 : 90의 비율을 갖는 실세스퀴옥산올리고머를 얻었다. To a dried flask equipped with a cooling tube and a stirrer, 10 parts by weight of distilled water, 20 parts by weight of acetonitrile (Daejeong Gold), and 2 parts by weight of the prepared catalyst were added dropwise, stirred at room temperature for 1 hour, and then 2-(3 ,4 Epoxycyclohexyl) 20 parts by weight of ethyltrimethoxysilane (Shin-Etsu, product name KBM-303) was added dropwise and stirred for an additional 6 hours. After completion of the reaction, the reaction was washed twice to extract the catalyst and impurities, and finally, a silsesquioxane oligomer having a ratio of cage-type silsesquioxane and leather-type silsesquioxane of 10:90 was obtained.
[합성예 2][Synthesis Example 2]
냉각관과 교반기를 구비한 건조된 플라스크에, 증류수 10 중량부, 아세토니트릴(대정화금) 50 중량부, 제조된 촉매 2 중량부를 적가하고, 1시간 동안 상온에서 교반한 후, 2-(3,4 에폭시사이클로헥실) 에틸트리메톡시실란(신에츠, 상품명 KBM-303) 20 중량부를 적가하여 6시간을 추가 교반하였다. 반응 완료 후 두 차례 세정하여 촉매와 불순물을 추출하였으며, 최종적으로 케이지형실세스퀴옥산 및 레더형실세스퀴옥산이 30 : 70의 비율을 갖는 실세스퀴옥산올리고머를 얻었다. To a dried flask equipped with a cooling pipe and a stirrer, 10 parts by weight of distilled water, 50 parts by weight of acetonitrile (Daejeong Gold), and 2 parts by weight of the prepared catalyst were added dropwise, stirred at room temperature for 1 hour, and then 2-(3 ,4 Epoxycyclohexyl) 20 parts by weight of ethyltrimethoxysilane (Shin-Etsu, product name KBM-303) was added dropwise and stirred for an additional 6 hours. After completion of the reaction, the reaction was washed twice to extract the catalyst and impurities, and finally, a silsesquioxane oligomer having a ratio of cage-type silsesquioxane and leather-type silsesquioxane of 30:70 was obtained.
[합성예 3][Synthesis Example 3]
냉각관과 교반기를 구비한 건조된 플라스크에, 증류수 10 중량부, 아세토니트릴(대정화금) 90 중량부, 제조된 촉매 2 중량부를 적가하고, 1시간 동안 상온에서 교반한 후, 2-(3,4 에폭시사이클로헥실) 에틸트리메톡시실란(신에츠, 상품명 KBM-303) 20 중량부를 적가하여 6시간을 추가 교반하였다. 반응 완료 후 두 차례 세정하여 촉매와 불순물을 추출하였으며, 최종적으로 케이지형실세스퀴옥산 및 레더형실세스퀴옥산이 50 : 50의 비율을 갖는 실세스퀴옥산올리고머를 얻었다.To a dried flask equipped with a cooling pipe and a stirrer, 10 parts by weight of distilled water, 90 parts by weight of acetonitrile (Daejeong Gold), and 2 parts by weight of the prepared catalyst were added dropwise, stirred at room temperature for 1 hour, and then 2-(3 ,4 Epoxycyclohexyl) 20 parts by weight of ethyltrimethoxysilane (Shin-Etsu, product name KBM-303) was added dropwise and stirred for an additional 6 hours. After completion of the reaction, the reaction was washed twice to extract the catalyst and impurities, and finally, a silsesquioxane oligomer having a ratio of cage-type silsesquioxane and leather-type silsesquioxane of 50:50 was obtained.
[합성예 4][Synthesis Example 4]
냉각관과 교반기를 구비한 건조된 플라스크에, 증류수 10 중량부, 아세토니트릴(대정화금) 220 중량부, 제조된 촉매 2 중량부를 적가하고, 1시간 동안 상온에서 교반한 후, 2-(3,4 에폭시사이클로헥실) 에틸트리메톡시실란(신에츠, 상품명 KBM-303) 20 중량부를 적가하여 6시간을 추가 교반하였다. 반응 완료 후 두 차례 세정하여 촉매와 불순물을 추출하였으며, 최종적으로 케이지형실세스퀴옥산 및 레더형실세스퀴옥산이 80 : 20의 비율을 갖는 실세스퀴옥산올리고머를 얻었다.To a dried flask equipped with a cooling pipe and a stirrer, 10 parts by weight of distilled water, 220 parts by weight of acetonitrile (Daejeong Gold), and 2 parts by weight of the prepared catalyst were added dropwise, stirred at room temperature for 1 hour, and then 2-(3 ,4 Epoxycyclohexyl) 20 parts by weight of ethyltrimethoxysilane (Shin-Etsu, product name KBM-303) was added dropwise and stirred for an additional 6 hours. After completion of the reaction, the reaction was washed twice to extract the catalyst and impurities, and finally, a silsesquioxane oligomer having a ratio of cage-type silsesquioxane and leather-type silsesquioxane of 80:20 was obtained.
[합성예 5][Synthesis Example 5]
냉각관과 교반기를 구비한 건조된 플라스크에, 증류수 10 중량부, 아세토니트릴(대정화금) 7 중량부, 제조된 촉매 2 중량부를 적가하고, 1시간 동안 상온에서 교반한 후, 2-(3,4 에폭시사이클로헥실) 에틸트리메톡시실란(신에츠, 상품명 KBM-303) 20 중량부를 적가하여 6시간을 추가 교반하였다. 반응 완료 후 두 차례 세정하여 촉매와 불순물을 추출하였으며, 최종적으로 케이지형실세스퀴옥산 및 레더형실세스퀴옥산이 3 : 97의 비율을 갖는 실세스퀴옥산올리고머를 얻었다.To a dried flask equipped with a cooling pipe and a stirrer, 10 parts by weight of distilled water, 7 parts by weight of acetonitrile (Daejeong Chemical Gold), and 2 parts by weight of the prepared catalyst were added dropwise, stirred at room temperature for 1 hour, and then 2-(3 ,4 Epoxycyclohexyl) 20 parts by weight of ethyltrimethoxysilane (Shin-Etsu, product name KBM-303) was added dropwise and stirred for an additional 6 hours. After completion of the reaction, the reaction was washed twice to extract the catalyst and impurities, and finally, a silsesquioxane oligomer having a ratio of cage-type silsesquioxane and leather-type silsesquioxane of 3:97 was obtained.
[합성예 6][Synthesis Example 6]
냉각관과 교반기를 구비한 건조된 플라스크에, 증류수 10 중량부, 아세토니트릴(대정화금) 10 중량부, 제조된 촉매 2 중량부를 적가하고, 1시간 동안 상온에서 교반한 후, 2-(3,4 에폭시사이클로헥실) 에틸트리메톡시실란(신에츠, 상품명 KBM-303) 20 중량부를 적가하여 6시간을 추가 교반하였다. 반응 완료 후 두 차례 세정하여 촉매와 불순물을 추출하였으며, 최종적으로 케이지형실세스퀴옥산 및 레더형실세스퀴옥산이 5 : 95의 비율을 갖는 실세스퀴옥산올리고머를 얻었다.To a dried flask equipped with a cooling pipe and a stirrer, 10 parts by weight of distilled water, 10 parts by weight of acetonitrile (Daejeong Gold), and 2 parts by weight of the prepared catalyst were added dropwise, stirred at room temperature for 1 hour, and then 2-(3 ,4 Epoxycyclohexyl) 20 parts by weight of ethyltrimethoxysilane (Shin-Etsu, product name KBM-303) was added dropwise and stirred for an additional 6 hours. After completion of the reaction, the reaction was washed twice to extract the catalyst and impurities, and finally, a silsesquioxane oligomer having a ratio of cage-type silsesquioxane and leather-type silsesquioxane of 5:95 was obtained.
[합성예 7][Synthesis Example 7]
냉각관과 교반기를 구비한 건조된 플라스크에, 증류수 10 중량부, 아세토니트릴(대정화금) 260 중량부, 제조된 촉매 2 중량부를 적가하고, 1시간 동안 상온에서 교반한 후, 2-(3,4 에폭시사이클로헥실) 에틸트리메톡시실란(신에츠, 상품명 KBM-303) 20 중량부를 적가하여 6시간을 추가 교반하였다. 반응 완료 후 두 차례 세정하여 촉매와 불순물을 추출하였으며, 최종적으로 케이지형실세스퀴옥산 및 레더형실세스퀴옥산이 85 : 15의 비율을 갖는 실세스퀴옥산올리고머를 얻었다.To a dried flask equipped with a cooling pipe and a stirrer, 10 parts by weight of distilled water, 260 parts by weight of acetonitrile (Daejeong Gold), and 2 parts by weight of the prepared catalyst were added dropwise, stirred at room temperature for 1 hour, and then 2-(3 ,4 Epoxycyclohexyl) 20 parts by weight of ethyltrimethoxysilane (Shin-Etsu, product name KBM-303) was added dropwise and stirred for an additional 6 hours. After completion of the reaction, the catalyst and impurities were extracted by washing twice, and finally, a silsesquioxane oligomer having a ratio of cage-type silsesquioxane and leather-type silsesquioxane of 85:15 was obtained.
[합성예 8][Synthesis Example 8]
냉각관과 교반기를 구비한 건조된 플라스크에, 증류수 10 중량부, 아세토니트릴(대정화금) 280 중량부, 제조된 촉매 2 중량부를 적가하고, 1시간 동안 상온에서 교반한 후, 2-(3,4 에폭시사이클로헥실) 에틸트리메톡시실란(신에츠, 상품명 KBM-303) 20 중량부를 적가하여 6시간을 추가 교반하였다. 반응 완료 후 두 차례 세정하여 촉매와 불순물을 추출하였으며, 최종적으로 케이지형실세스퀴옥산 및 레더형실세스퀴옥산이 90 : 10의 비율을 갖는 실세스퀴옥산올리고머를 얻었다.To a dried flask equipped with a cooling tube and a stirrer, 10 parts by weight of distilled water, 280 parts by weight of acetonitrile (Daejeong Gold), and 2 parts by weight of the prepared catalyst were added dropwise, stirred at room temperature for 1 hour, and then 2-(3 ,4 Epoxycyclohexyl) 20 parts by weight of ethyltrimethoxysilane (Shin-Etsu, product name KBM-303) was added dropwise and stirred for an additional 6 hours. After completion of the reaction, the catalyst and impurities were extracted by washing twice, and finally, a silsesquioxane oligomer having a ratio of cage-type silsesquioxane and leather-type silsesquioxane of 90:10 was obtained.
[실시예 1][Example 1]
상기 합성예 1에서 얻어진 실세스퀴옥산올리고머를 50 g을 메틸아이소부틸케톤에 50 중량%로 녹여 100 g의 조성물을 제조하였다. 이후, 준비된 조성물 100 중량부에 클로로아세토페논 5 중량부, 실리콘계 첨가제 BYK-302 1 중량부 및 아크릴계 첨가제 BYK-359 1 중량부를 첨가하고 10분간 교반하여 케이지형 구조와 레더형 구조의 비율이 10 중량% : 90 중량% 인 광경화형 수지 조성물을 제조하였다. 제조된 광경화형 수지 조성물을 80 ㎛ 트리아세틸 셀룰로오스 필름(FUJIFILM) 위에 도포하고 85의 건조오븐에서 용매를 증발시킨 후 UV 장비를 이용하여 1 J/cm2의 UV를 조사하여 결과물을 수득하였다.50 g of the silsesquioxane oligomer obtained in Synthesis Example 1 was dissolved at 50% by weight in methyl isobutyl ketone to prepare a 100 g composition. Afterwards, 5 parts by weight of chloroacetophenone, 1 part by weight of silicone-based additive BYK-302, and 1 part by weight of acrylic additive BYK-359 were added to 100 parts by weight of the prepared composition and stirred for 10 minutes so that the ratio of the cage-type structure and the leather-type structure was 10 parts by weight. %: 90% by weight photocurable resin composition was prepared. The prepared photocurable resin composition was applied on an 80 ㎛ triacetyl cellulose film (FUJIFILM), the solvent was evaporated in a drying oven at 85°C, and the result was obtained by irradiating 1 J/cm 2 of UV using a UV device.
[실시예 2][Example 2]
상기 합성예 2에서 얻어진 실세스퀴옥산올리고머를 50 g을 메틸아이소부틸케톤에 50 중량%로 녹여 100 g의 조성물을 제조하였다. 이후, 준비된 조성물 100 중량부에 클로로아세토페논 5 중량부, 실리콘계 첨가제 BYK-302 1 중량부 및 아크릴계 첨가옥산 및 레더형실세스퀴옥산이 10 : 90의 비율을 갖는 실세스퀴옥산올리고머를 얻었다. 50 g of the silsesquioxane oligomer obtained in Synthesis Example 2 was dissolved at 50% by weight in methyl isobutyl ketone to prepare a 100 g composition. Afterwards, a silsesquioxane oligomer having a ratio of 10:90 of 5 parts by weight of chloroacetophenone, 1 part by weight of silicone-based additive BYK-302, and acrylic-based added oxane and leather-type silsesquioxane was obtained based on 100 parts by weight of the prepared composition.
[합성예 2][Synthesis Example 2]
냉각관과 교반기를 구비한 건조된 플라스크에, 증류수 10 중량부, 아세토니트릴(대정화금) 50 중량부, 제조된 촉매 2 중량부를 적가하고, 1시간 동안 상온에서 교반한 후, 2-(3,4 에폭시사이클로헥실) 에틸트리메톡시실란(신에츠, 상품명 KBM-303) 20 중량부를 적가하여 6시간을 추가 교반하였다. 반응 완료 후 두 차례 세정하여 촉매와 불순물을 추출하였으며, 최종적으로 케이지형실세스퀴옥산 및 레더형실세스퀴옥산이 30 : 70의 비율을 갖는 실세스퀴옥산올리고머를 얻었다. To a dried flask equipped with a cooling pipe and a stirrer, 10 parts by weight of distilled water, 50 parts by weight of acetonitrile (Daejeong Gold), and 2 parts by weight of the prepared catalyst were added dropwise, stirred at room temperature for 1 hour, and then 2-(3 ,4 Epoxycyclohexyl) 20 parts by weight of ethyltrimethoxysilane (Shin-Etsu, product name KBM-303) was added dropwise and stirred for an additional 6 hours. After completion of the reaction, the reaction was washed twice to extract the catalyst and impurities, and finally, a silsesquioxane oligomer having a ratio of cage-type silsesquioxane and leather-type silsesquioxane of 30:70 was obtained.
[합성예 3][Synthesis Example 3]
냉각관과 교반기를 구비한 건조된 플라스크에, 증류수 10 중량부, 아세토니트릴(대정화금) 90 중량부, 제조된 촉매 2 중량부를 적가하고, 1시간 동안 상온에서 교반한 후, 2-(3,4 에폭시사이클로헥실) 에틸트리메톡시실란(신에츠, 상품명 KBM-303) 20 중량부를 적가하여 6시간을 추가 교반하였다. 반응 완료 후 두 차례 세정하여 촉매와 불순물을 추출하였으며, 최종적으로 케이지형실세스퀴옥산 및 레더형실세스퀴옥산이 50 : 50의 비율을 갖는 실세스퀴옥산올리고머를 얻었다.To a dried flask equipped with a cooling pipe and a stirrer, 10 parts by weight of distilled water, 90 parts by weight of acetonitrile (Daejeong Gold), and 2 parts by weight of the prepared catalyst were added dropwise, stirred at room temperature for 1 hour, and then 2-(3 ,4 Epoxycyclohexyl) 20 parts by weight of ethyltrimethoxysilane (Shin-Etsu, product name KBM-303) was added dropwise and stirred for an additional 6 hours. After completion of the reaction, the reaction was washed twice to extract the catalyst and impurities, and finally, a silsesquioxane oligomer having a ratio of cage-type silsesquioxane and leather-type silsesquioxane of 50:50 was obtained.
[합성예 4][Synthesis Example 4]
냉각관과 교반기를 구비한 건조된 플라스크에, 증류수 10 중량부, 아세토니트릴(대정화금) 220 중량부, 제조된 촉매 2 중량부를 적가하고, 1시간 동안 상온에서 교반한 후, 2-(3,4 에폭시사이클로헥실) 에틸트리메톡시실란(신에츠, 상품명 KBM-303) 20 중량부를 적가하여 6시간을 추가 교반하였다. 반응 완료 후 두 차례 세정하여 촉매와 불순물을 추출하였으며, 최종적으로 케이지형실세스퀴옥산 및 레더형실세스퀴옥산이 80 : 20의 비율을 갖는 실세스퀴옥산올리고머를 얻었다.To a dried flask equipped with a cooling pipe and a stirrer, 10 parts by weight of distilled water, 220 parts by weight of acetonitrile (Daejeong Gold), and 2 parts by weight of the prepared catalyst were added dropwise, stirred at room temperature for 1 hour, and then 2-(3 ,4 Epoxycyclohexyl) 20 parts by weight of ethyltrimethoxysilane (Shin-Etsu, product name KBM-303) was added dropwise and stirred for an additional 6 hours. After completion of the reaction, the reaction was washed twice to extract the catalyst and impurities, and finally, a silsesquioxane oligomer having a ratio of cage-type silsesquioxane and leather-type silsesquioxane of 80:20 was obtained.
[합성예 5][Synthesis Example 5]
냉각관과 교반기를 구비한 건조된 플라스크에, 증류수 10 중량부, 아세토니트릴(대정화금) 7 중량부, 제조된 촉매 2 중량부를 적가하고, 1시간 동안 상온에서 교반한 후, 2-(3,4 에폭시사이클로헥실) 에틸트리메톡시실란(신에츠, 상품명 KBM-303) 20 중량부를 적가하여 6시간을 추가 교반하였다. 반응 완료 후 두 차례 세정하여 촉매와 불순물을 추출하였으며, 최종적으로 케이지형실세스퀴옥산 및 레더형실세스퀴옥산이 3 : 97의 비율을 갖는 실세스퀴옥산올리고머를 얻었다.To a dried flask equipped with a cooling pipe and a stirrer, 10 parts by weight of distilled water, 7 parts by weight of acetonitrile (Daejeong Chemical Gold), and 2 parts by weight of the prepared catalyst were added dropwise, stirred at room temperature for 1 hour, and then 2-(3 ,4 Epoxycyclohexyl) 20 parts by weight of ethyltrimethoxysilane (Shin-Etsu, product name KBM-303) was added dropwise and stirred for an additional 6 hours. After completion of the reaction, the reaction was washed twice to extract the catalyst and impurities, and finally, a silsesquioxane oligomer having a ratio of cage-type silsesquioxane and leather-type silsesquioxane of 3:97 was obtained.
[합성예 6][Synthesis Example 6]
냉각관과 교반기를 구비한 건조된 플라스크에, 증류수 10 중량부, 아세토니트릴(대정화금) 10 중량부, 제조된 촉매 2 중량부를 적가하고, 1시간 동안 상온에서 교반한 후, 2-(3,4 에폭시사이클로헥실) 에틸트리메톡시실란(신에츠, 상품명 KBM-303) 20 중량부를 적가하여 6시간을 추가 교반하였다. 반응 완료 후 두 차례 세정하여 촉매와 불순물을 추출하였으며, 최종적으로 케이지형실세스퀴옥산 및 레더형실세스퀴옥산이 5 : 95의 비율을 갖는 실세스퀴옥산올리고머를 얻었다.To a dried flask equipped with a cooling pipe and a stirrer, 10 parts by weight of distilled water, 10 parts by weight of acetonitrile (Daejeong Gold), and 2 parts by weight of the prepared catalyst were added dropwise, stirred at room temperature for 1 hour, and then 2-(3 ,4 Epoxycyclohexyl) 20 parts by weight of ethyltrimethoxysilane (Shin-Etsu, product name KBM-303) was added dropwise and stirred for an additional 6 hours. After completion of the reaction, the reaction was washed twice to extract the catalyst and impurities, and finally, a silsesquioxane oligomer having a ratio of cage-type silsesquioxane and leather-type silsesquioxane of 5:95 was obtained.
[합성예 7][Synthesis Example 7]
냉각관과 교반기를 구비한 건조된 플라스크에, 증류수 10 중량부, 아세토니트릴(대정화금) 260 중량부, 제조된 촉매 2 중량부를 적가하고, 1시간 동안 상온에서 교반한 후, 2-(3,4 에폭시사이클로헥실) 에틸트리메톡시실란(신에츠, 상품명 KBM-303) 20 중량부를 적가하여 6시간을 추가 교반하였다. 반응 완료 후 두 차례 세정하여 촉매와 불순물을 추출하였으며, 최종적으로 케이지형실세스퀴옥산 및 레더형실세스퀴옥산이 85 : 15의 비율을 갖는 실세스퀴옥산올리고머를 얻었다.To a dried flask equipped with a cooling pipe and a stirrer, 10 parts by weight of distilled water, 260 parts by weight of acetonitrile (Daejeong Gold), and 2 parts by weight of the prepared catalyst were added dropwise, stirred at room temperature for 1 hour, and then 2-(3 ,4 Epoxycyclohexyl) 20 parts by weight of ethyltrimethoxysilane (Shin-Etsu, product name KBM-303) was added dropwise and stirred for an additional 6 hours. After completion of the reaction, the catalyst and impurities were extracted by washing twice, and finally, a silsesquioxane oligomer having a ratio of cage-type silsesquioxane and leather-type silsesquioxane of 85:15 was obtained.
[합성예 8][Synthesis Example 8]
냉각관과 교반기를 구비한 건조된 플라스크에, 증류수 10 중량부, 아세토니트릴(대정화금) 280 중량부, 제조된 촉매 2 중량부를 적가하고, 1시간 동안 상온에서 교반한 후, 2-(3,4 에폭시사이클로헥실) 에틸트리메톡시실란(신에츠, 상품명 KBM-303) 20 중량부를 적가하여 6시간을 추가 교반하였다. 반응 완료 후 두 차례 세정하여 촉매와 불순물을 추출하였으며, 최종적으로 케이지형실세스퀴옥산 및 레더형실세스퀴옥산이 90 : 10의 비율을 갖는 실세스퀴옥산올리고머를 얻었다.To a dried flask equipped with a cooling tube and a stirrer, 10 parts by weight of distilled water, 280 parts by weight of acetonitrile (Daejeong Gold), and 2 parts by weight of the prepared catalyst were added dropwise, stirred at room temperature for 1 hour, and then 2-(3 ,4 Epoxycyclohexyl) 20 parts by weight of ethyltrimethoxysilane (Shin-Etsu, product name KBM-303) was added dropwise and stirred for an additional 6 hours. After completion of the reaction, the catalyst and impurities were extracted by washing twice, and finally, a silsesquioxane oligomer having a ratio of cage-type silsesquioxane and leather-type silsesquioxane of 90:10 was obtained.
[실시예 1][Example 1]
상기 합성예 1에서 얻어진 실세스퀴옥산올리고머를 50 g을 메틸아이소부틸케톤에 50 중량%로 녹여 100 g의 조성물을 제조하였다. 이후, 준비된 조성물 100 중량부에 클로로아세토페논 5 중량부, 실리콘계 첨가제 BYK-302 1 중량부 및 아크릴계 첨가제 BYK-359 1 중량부를 첨가하고 10분간 교반하여 케이지형 구조와 레더형 구조의 비율이 10 중량% : 90 중량% 인 광경화형 수지 조성물을 제조하였다. 제조된 광경화형 수지 조성물을 80 ㎛ 트리아세틸 셀룰로오스 필름(FUJIFILM) 위에 도포하고 85의 건조오븐에서 용매를 증발시킨 후 UV 장비를 이용하여 1 J/cm2의 UV를 조사하여 결과물을 수득하였다.50 g of the silsesquioxane oligomer obtained in Synthesis Example 1 was dissolved at 50% by weight in methyl isobutyl ketone to prepare a 100 g composition. Afterwards, 5 parts by weight of chloroacetophenone, 1 part by weight of silicone-based additive BYK-302, and 1 part by weight of acrylic additive BYK-359 were added to 100 parts by weight of the prepared composition and stirred for 10 minutes so that the ratio of the cage-type structure and the leather-type structure was 10 parts by weight. %: 90% by weight photocurable resin composition was prepared. The prepared photocurable resin composition was applied on an 80 ㎛ triacetyl cellulose film (FUJIFILM), the solvent was evaporated in a drying oven at 85°C, and the result was obtained by irradiating 1 J/cm 2 of UV using a UV device.
[실시예 2][Example 2]
상기 합성예 2에서 얻어진 실세스퀴옥산올리고머를 50 g을 메틸아이소부틸케톤에 50 중량%로 녹여 100 g의 조성물을 제조하였다. 이후, 준비된 조성물 100 중량부에 클 BYK-359 1 중량부를 첨가하고 10분간 교반하여 케이지형 구조와 레더형 구조의 비율이 30 중량% : 70 중량% 인 광경화형 수지 조성물을 제조하였다. 제조된 광경화형 수지 조성물을 80 ㎛ 트리아세틸 셀룰로오스 필름(FUJIFILM) 위에 도포하고 85 의 건조오븐에서 용매를 증발시킨 후 UV 장비를 이용하여 1 J/cm2의 UV를 조사하여 결과물을 수득하였다.50 g of the silsesquioxane oligomer obtained in Synthesis Example 2 was dissolved at 50% by weight in methyl isobutyl ketone to prepare a 100 g composition. Afterwards, 1 part by weight of BYK-359 was added to 100 parts by weight of the prepared composition and stirred for 10 minutes to prepare a photocurable resin composition having a cage-type structure and a leather-type structure ratio of 30% by weight: 70% by weight. The prepared photocurable resin composition was applied on an 80 ㎛ triacetyl cellulose film (FUJIFILM), the solvent was evaporated in a drying oven at 85°C, and the result was obtained by irradiating UV at 1 J/cm 2 using a UV equipment.
[실시예 3][Example 3]
상기 합성예 3에서 얻어진 실세스퀴옥산올리고머를 50 g을 메틸아이소부틸케톤에 50 중량%로 녹여 100 g의 조성물을 제조하였다. 이후, 준비된 조성물 100 중량부에클로로아세토페논 5 중량부, 실리콘계 첨가제 BYK-302 1 중량부 및 아크릴계 첨가제 BYK-359 1 중량부를 첨가하고 10분간 교반하여 케이지형 구조와 레더형 구조의 비율이 50 중량% : 50 중량% 인 광경화형 수지 조성물을 제조하였다. 제조된 광경화형 수지 조성물을 80 ㎛ 트리아세틸 셀룰로오스 필름(FUJIFILM) 위에 도포하고 85의 건조오븐에서 용매를 증발시킨 후 UV 장비를 이용하여 1 J/cm2의 UV를 조사하여 결과물을 수득하였다.50 g of the silsesquioxane oligomer obtained in Synthesis Example 3 was dissolved at 50% by weight in methyl isobutyl ketone to prepare a 100 g composition. Afterwards, 5 parts by weight of chloroacetophenone, 1 part by weight of silicone-based additive BYK-302, and 1 part by weight of acrylic additive BYK-359 were added to 100 parts by weight of the prepared composition and stirred for 10 minutes so that the ratio of the cage-type structure and the leather-type structure was 50 parts by weight. %: 50% by weight photocurable resin composition was prepared. The prepared photocurable resin composition was applied on an 80 ㎛ triacetyl cellulose film (FUJIFILM), the solvent was evaporated in a drying oven at 85°C, and the result was obtained by irradiating 1 J/cm 2 of UV using a UV device.
[실시예 4][Example 4]
상기 합성예 4에서 얻어진 실세스퀴옥산올리고머를 50 g을 메틸아이소부틸케톤에 50 중량%로 녹여 100 g의 조성물을 제조하였다. 이후, 준비된 조성물 100 중량부에 클로로아세토페논 5 중량부, 실리콘계 첨가제 BYK-302 1 중량부 및 아크릴계 첨가제 BYK-359 1 중량부를 첨가하고 10분간 교반하여 케이지형 구조와 레더형 구조의 비율이 80 중량% : 20 중량% 인 광경화형 수지 조성물을 제조하였다. 제조된 광경화형 수지 조성물을 80 ㎛ 트리아세틸 셀룰로오스 필름(FUJIFILM) 위에 도포하고 85의 건조오븐에서 용매를 증발시킨 후 UV 장비를 이용하여 1 J/cm2의 UV를 조사하여 결과물을 수득하였다.50 g of the silsesquioxane oligomer obtained in Synthesis Example 4 was dissolved at 50% by weight in methyl isobutyl ketone to prepare a 100 g composition. Afterwards, 5 parts by weight of chloroacetophenone, 1 part by weight of silicone-based additive BYK-302, and 1 part by weight of acrylic additive BYK-359 were added to 100 parts by weight of the prepared composition and stirred for 10 minutes so that the ratio of the cage-type structure and the leather-type structure was 80 parts by weight. %: 20% by weight photocurable resin composition was prepared. The prepared photocurable resin composition was applied on an 80 ㎛ triacetyl cellulose film (FUJIFILM), the solvent was evaporated in a drying oven at 85°C, and the result was obtained by irradiating 1 J/cm 2 of UV using a UV device.
[실시예 5][Example 5]
상기 합성예 2에서 얻어진 실세스퀴옥산올리고머를 50 g을 메틸아이소부틸케톤에 50 중량%로 녹여 100 g의 조성물을 제조하였다. 이후, 준비된 조성물 100 중량부에 클로로아세토페논 5 중량부, 실리콘계 첨가제 BYK-302 1 중량부 및 아크릴계 첨가제 BYK-359 1 중량부를 첨가하고 10분간 교반하여 케이지형 구조와 레더형 구조의 비율이 30 중량% : 70 중량% 인 광경화형 수지 조성물을 제조하였다. 제조된 광경화형 수지 조성물을 80 ㎛ 트리아세틸 셀룰로오스 필름(FUJIFILM) 위에 도포하고 85의 건조오븐에서 용매를 증발시킨 후 UV 장비를 이용하여 1 J/cm2의 UV를 조사하였으며, 반대면에도 똑같은 공정을 통해 양면 코팅하여 결과물을 수득하였다.50 g of the silsesquioxane oligomer obtained in Synthesis Example 2 was dissolved at 50% by weight in methyl isobutyl ketone to prepare a 100 g composition. Afterwards, 5 parts by weight of chloroacetophenone, 1 part by weight of silicone additive BYK-302, and 1 part by weight of acrylic additive BYK-359 were added to 100 parts by weight of the prepared composition and stirred for 10 minutes so that the ratio of the cage-type structure and the leather-type structure was 30 parts by weight. %: A photocurable resin composition of 70% by weight was prepared. The prepared photocurable resin composition was applied on an 80 ㎛ triacetyl cellulose film (FUJIFILM), the solvent was evaporated in a drying oven at 85°C, and then 1 J/cm 2 UV was irradiated using a UV equipment. The same process was performed on the other side. The result was obtained by coating both sides.
[비교예 1][Comparative Example 1]
실시예 및 비교예의 코팅기재로 사용한 80 ㎛ 트리아세틸 셀룰로오스 필름(FUJIFILM) 단독으로 하기 실험을 진행하였다.The following experiment was conducted solely on the 80 ㎛ triacetyl cellulose film (FUJIFILM) used as the coating substrate in Examples and Comparative Examples.
[비교예 2][Comparative Example 2]
상기 합성예 5에서 얻어진 실세스퀴옥산올리고머를 50 g을 메틸아이소부틸케톤에 50 중량%로 녹여 100 g의 조성물을 제조하였다. 이후, 준비된 조성물 100 중량부에 클로로아세토페논 5 중량부, 실리콘계 첨가제 BYK-302 1 중량부 및 아크릴계 첨가제 BYK-359 1 중량부를 첨가하고 10분간 교반하여 케이지형 구조와 레더형 구조의 비율이 3 중량% : 97 중량% 인 광경화형 수지 조성물을 제조하였다.제조된 광경화형 수지 조성물을 80 ㎛ 트리아세틸 셀룰로오스 필름(FUJIFILM) 위에 도포하고 85 의 건조오븐에서 용매를 증발시킨 후 UV 장비를 이용하여 1 J/cm2의 UV를 조사하여 결과물을 수득하였다.50 g of the silsesquioxane oligomer obtained in Synthesis Example 5 was dissolved at 50% by weight in methyl isobutyl ketone to prepare a 100 g composition. Afterwards, 5 parts by weight of chloroacetophenone, 1 part by weight of silicone additive BYK-302, and 1 part by weight of acrylic additive BYK-359 were added to 100 parts by weight of the prepared composition and stirred for 10 minutes so that the ratio of the cage-type structure and the leather-type structure was 3 weight. A photocurable resin composition of %: 97% by weight was prepared. The prepared photocurable resin composition was applied on an 80 ㎛ triacetyl cellulose film (FUJIFILM), the solvent was evaporated in a drying oven at 85°C, and then dried at 1 J using a UV equipment. The result was obtained by irradiating UV at /cm 2 .
[비교예 3][Comparative Example 3]
상기 합성예 6에서 얻어진 실세스퀴옥산올리고머를 50 g을 메틸아이소부틸케톤에 50 중량%로 녹여 100 g의 조성물을 제조하였다. 이후, 준비된 조성물 100 중량부에 클로로아세토페논 5 중량부, 실리콘계 첨가제 BYK-302 1 중량부 및 아크릴계 첨가제 BYK-359 1 중량부를 첨가하고 10분간 교반하여 케이지형 구조와 레더형 구조의 비율이 5 중량% : 95 중량% 인 광경화형 수지 조성물을 제조하였다. 50 g of the silsesquioxane oligomer obtained in Synthesis Example 6 was dissolved at 50% by weight in methyl isobutyl ketone to prepare a 100 g composition. Afterwards, 5 parts by weight of chloroacetophenone, 1 part by weight of silicone additive BYK-302, and 1 part by weight of acrylic additive BYK-359 were added to 100 parts by weight of the prepared composition and stirred for 10 minutes so that the ratio of the cage-type structure and the leather-type structure was 5 weight. %: A photocurable resin composition of 95% by weight was prepared.
제조된 광경화형 수지 조성물을 80 ㎛ 트리아세틸 셀룰로오스 필름(FUJIFILM) 위에 도포하고 85 의 건조오븐에서 용매를 증발시킨 후 UV 장비를 이용하여 1 J/cm2의 UV를 조사하여 결과물을 수득하였다.The prepared photocurable resin composition was applied on an 80 ㎛ triacetyl cellulose film (FUJIFILM), the solvent was evaporated in a drying oven at 85°C, and the result was obtained by irradiating UV at 1 J/cm 2 using a UV device.
[비교예 4][Comparative Example 4]
상기 합성예 7에서 얻어진 실세스퀴옥산올리고머를 50 g을 메틸아이소부틸케톤에 50 중량%로 녹여 100 g의 조성물을 제조하였다. 이후, 준비된 조성물 100 중량부에 클로로아세토페논 5 중량부, 실리콘계 첨가제 BYK-302 1 중량부 및 아크릴계 첨가제 BYK-359 1 중량부를 첨가하고 10분간 교반하여 케이지형 구조와 레더형 구조의 비율이 85 중량% : 15 중량% 인 광경화형 수지 조성물을 제조하였다. 50 g of the silsesquioxane oligomer obtained in Synthesis Example 7 was dissolved at 50% by weight in methyl isobutyl ketone to prepare a 100 g composition. Afterwards, 5 parts by weight of chloroacetophenone, 1 part by weight of silicone-based additive BYK-302, and 1 part by weight of acrylic additive BYK-359 were added to 100 parts by weight of the prepared composition and stirred for 10 minutes so that the ratio of the cage-type structure and the leather-type structure was 85 parts by weight. %: 15% by weight photocurable resin composition was prepared.
제조된 광경화형 수지 조성물을 80 ㎛ 트리아세틸 셀룰로오스 필름(FUJIFILM) 위에 도포하고 85 의 건조오븐에서 용매를 증발시킨 후 UV 장비를 이용하여 1 J/cm2의 UV를 조사하여 결과물을 수득하였다.The prepared photocurable resin composition was applied on an 80 ㎛ triacetyl cellulose film (FUJIFILM), the solvent was evaporated in a drying oven at 85°C, and the result was obtained by irradiating UV at 1 J/cm 2 using a UV device.
[비교예 5][Comparative Example 5]
상기 합성예 8에서 얻어진 실세스퀴옥산올리고머를 50 g을 메틸아이소부틸케톤에 50 중량%로 녹여 100 g의 조성물을 제조하였다. 이후, 준비된 조성물 100 중량부에 클로로아세토페논 5 중량부, 실리콘계 첨가제 BYK-302 1 중량부 및 아크릴계 첨가제 BYK-359 1 중량부를 첨가하고 10분간 교반하여 케이지형 구조와 레더형 구조의 비율이 90 중량% : 10 중량% 인 광경화형 수지 조성물을 제조하였다. 50 g of the silsesquioxane oligomer obtained in Synthesis Example 8 was dissolved at 50% by weight in methyl isobutyl ketone to prepare a 100 g composition. Afterwards, 5 parts by weight of chloroacetophenone, 1 part by weight of silicone-based additive BYK-302, and 1 part by weight of acrylic additive BYK-359 were added to 100 parts by weight of the prepared composition and stirred for 10 minutes so that the ratio of the cage-type structure and the leather-type structure was 90 parts by weight. %: 10% by weight photocurable resin composition was prepared.
제조된 광경화형 수지 조성물을 80 ㎛ 트리아세틸 셀룰로오스 필름(FUJIFILM) 위에 도포하고 85 의 건조오븐에서 용매를 증발시킨 후 UV 장비를 이용하여 1 J/cm2의 UV를 조사하여 결과물을 수득하였다.The prepared photocurable resin composition was applied on an 80 ㎛ triacetyl cellulose film (FUJIFILM), the solvent was evaporated in a drying oven at 85°C, and the result was obtained by irradiating UV at 1 J/cm 2 using a UV equipment.
[실험][Experiment]
상기 실시예 1, 실시예 2, 실시예 3, 실시예 4, 실시예5, 비교예 1, 비교예 2, 비교예 3, 비교예 4 및 비교예 5에서 수득한 결과물을 대상으로 코팅 전후에 대하여 연필경도, 접착력, 투과도, 헤이즈, 수분투과도를 측정하여 하기 표 1에 나타내었다.Before and after coating the results obtained in Example 1, Example 2, Example 3, Example 4, Example 5, Comparative Example 1, Comparative Example 2, Comparative Example 3, Comparative Example 4, and Comparative Example 5. Pencil hardness, adhesion, permeability, haze, and moisture permeability were measured and shown in Table 1 below.
- 연필경도: JIS 5600-5-4에 의거하여 500 g 하중으로 평가하였다. 연필은 미쯔비시 제품을 사용하고 한 연필 경도당 5회 실시하여 2개 이상 스크래치가 발생하면 불량으로 판정하였다. 측정경도와 스크래치 미발생 횟수/실시 횟수로 표기하였다. - Pencil hardness: evaluated with a load of 500 g according to JIS 5600-5-4. The pencil was a Mitsubishi product, and the test was conducted 5 times per pencil hardness, and if 2 or more scratches occurred, it was judged as defective. Measured hardness was expressed as number of non-scratches/number of executions.
- 접착력 평가: JIS K5600-5-6에 의거하여 1mm 간격으로 컷터날로 긁어서 격자무늬로 100개의 흠집을 내고, 점착테이프를 그 위에 저 붙였다가 900 방향으로 떼어내어 코팅층 표면이 점착테이프에 붙어서 떨어지는지를 육안으로 확인하였다. 표기는 100개중 떨어지지 않은 개수로 표기하였다.- Adhesion evaluation: Based on JIS K5600-5-6, scratch with a cutter blade at 1mm intervals to make 100 scratches in a grid pattern, attach adhesive tape on top of them, then peel off in the 900 direction to see if the surface of the coating layer sticks to the adhesive tape and falls off. was confirmed visually. It is written as the number that did not fall out of 100.
(예: 떨어지지 않은 개수/100으로 표기, 100개가 떨어지지 않으면 100/100으로 표기 함.)(Example: The number that did not fall is indicated as /100. If 100 pieces do not fall, it is indicated as 100/100.)
- 투과도 및 헤이즈: ISO 14782에 의거하여, COH-400 (Nippon Denshoku)를 이용해 측정하였다. 샘플 당 5회씩 측정하여 평균값을 기재하였다.- Transmittance and haze: Measured using COH-400 (Nippon Denshoku) according to ISO 14782. Each sample was measured 5 times and the average value was reported.
- 수분투과도: MOCON 장비를 이용하여 37.8°C, 100% RH(Relative Humidity) 항온 항습 조건에서 측정하였다.- Moisture permeability: Measured under constant temperature and humidity conditions at 37.8°C and 100% RH (Relative Humidity) using MOCON equipment.
(500gf)pencil hardness
(500g f )
상기 표 1에 나타나는 바와 같이 본 발명의 실시예 2, 실시예 3, 실시예 5는 실시예 1, 실시예 4, 비교예 1, 비교예 2, 비교예 3, 비교예 4 및 비교예 5와 비교하여 현저히 우수한 물성을 나타내었다. 특히 실시예 2와 이의 양면코팅인 실시예 5의 경우 더욱 우수한 TAC 필름의 수분투과도와 연필경도를 가짐을 확인 할 수 있다.As shown in Table 1, Examples 2, 3, and 5 of the present invention are similar to Examples 1, 4, Comparative Example 1, Comparative Example 2, Comparative Example 3, Comparative Example 4, and Comparative Example 5. In comparison, it showed significantly superior physical properties. In particular, it can be confirmed that Example 2 and its double-sided coating, Example 5, have superior TAC film moisture permeability and pencil hardness.
Claims (6)
4 g/m2.day이상의 수분투과도를 갖는 필름에서 내투습성을 향상시키기 위한 코팅 조성물.Containing a silsesquioxane oligomer having a weight ratio of cage-type silsesquioxane resin and leather-type silsesquioxane resin of 30:70 to 50:50,
A coating composition for improving moisture permeability resistance in films having a moisture permeability of 4 g/m 2 .day or more.
상기 실세스퀴옥산올리고머는 화학식 1로 표시되는 레더형실세스퀴옥산 수지에 화학식 2로 표시되는 케이지형실세스퀴옥산 수지가 결합된 것인 코팅 조성물.
[화학식 1]
상기 화학식 1에서,
R1,R2,R3,R4는 각각 독립적으로 치환기로 치환되거나 치환되지 않은 메틸기; 페닐기; 아미노기; (메타)아크릴기; 비닐기; 에폭시기; 사이올기; 또는 자외선흡수체이며, n은 1 내지 100의 정수이고,
R5,R6,R7,R8은 각각 독립적으로, 수소; 치환기로 치환되거나 치환되지 않은 C1~C10의 알킬기; 또는 하기 화학식 2로 표시되는 연결기이며, R5,R6,R7,R8중 적어도 하나는 하기 화학식 2와 연결되며,
[화학식 2]
상기 화학식 2에서,
R은 각각 독립적으로 치환기로 치환되거나 치환되지 않은 메틸기, 페닐기, 아미노기, (메타)아크릴기, 비닐기, 에폭시기, 사이올기 또는 자외선차단제이며,
R0는 각각 독립적으로 수소 또는 치환되거나 치환되지 않은 C1~C10의 알킬기이며,
n은 3 내지 6의 정수이며
상기 화학식 1 또는 2에서 치환기는 각각 독립적으로 중수소, 할로겐, 아민기, 에폭시기, (메타)아크릴기, 사이올기, 이소시아네이트기, 니트릴기, 니트로기 또는 페닐기이다.According to clause 1,
The silsesquioxane oligomer is a coating composition in which a cage-type silsesquioxane resin represented by Formula 2 is combined with a leather-type silsesquioxane resin represented by Formula 1.
[Formula 1]
In Formula 1,
R 1 , R 2 , R 3 , and R 4 are each independently a methyl group substituted or unsubstituted with a substituent; phenyl group; amino group; (meth)acrylic group; vinyl group; epoxy group; Cyol group; or an ultraviolet ray absorber, n is an integer from 1 to 100,
R 5 , R 6 , R 7 , and R 8 are each independently hydrogen; C1~C10 alkyl group substituted or unsubstituted with a substituent; Or it is a linking group represented by the following formula (2), and at least one of R 5 , R 6 , R 7 , and R 8 is connected to the formula (2) below,
[Formula 2]
In Formula 2,
R is each independently a methyl group, phenyl group, amino group, (meth)acrylic group, vinyl group, epoxy group, thiol group or sunscreen, which may or may not be substituted with a substituent,
R 0 is each independently hydrogen or a substituted or unsubstituted alkyl group of C 1 to C 10 ,
n is an integer from 3 to 6
In Formula 1 or 2, the substituents are each independently deuterium, halogen, amine group, epoxy group, (meth)acrylic group, thiol group, isocyanate group, nitrile group, nitro group, or phenyl group.
상기 실세스퀴옥산올리고머의 올리고머 내 케이지 구조의 비율이 25 내지 35 중량%이고,
상기 코팅 조성물은 광 또는 열로 개시되는 양이온 개시제, 라디칼개시제 또는 용매 중 하나 이상을 더 포함하는 코팅 조성물.According to clause 1,
The ratio of the cage structure in the oligomer of the silsesquioxane oligomer is 25 to 35% by weight,
The coating composition further includes one or more of a cationic initiator, a radical initiator, or a solvent that is initiated with light or heat.
상기 기재는 트리아세틸 셀룰로오스인 필름.According to clause 4,
A film wherein the substrate is triacetyl cellulose.
상기 필름은 100 g/m2.day 이하의 수분투과도를 갖는 필름.According to clause 5,
The film has a moisture permeability of 100 g/m 2 .day or less.
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