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WO2014092388A1 - Film de revêtement dur hybride organique-inorganique, et plaque de polarisation le comprenant - Google Patents

Film de revêtement dur hybride organique-inorganique, et plaque de polarisation le comprenant Download PDF

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Publication number
WO2014092388A1
WO2014092388A1 PCT/KR2013/011258 KR2013011258W WO2014092388A1 WO 2014092388 A1 WO2014092388 A1 WO 2014092388A1 KR 2013011258 W KR2013011258 W KR 2013011258W WO 2014092388 A1 WO2014092388 A1 WO 2014092388A1
Authority
WO
WIPO (PCT)
Prior art keywords
acrylate
hard coating
organic
coating film
inorganic hybrid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/KR2013/011258
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English (en)
Korean (ko)
Inventor
임거산
김희봉
안명용
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dongwoo Fine Chem Co Ltd
Original Assignee
Dongwoo Fine Chem Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dongwoo Fine Chem Co Ltd filed Critical Dongwoo Fine Chem Co Ltd
Publication of WO2014092388A1 publication Critical patent/WO2014092388A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/14—Layered products comprising a layer of synthetic resin next to a particulate layer
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
    • B32B27/308—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers comprising acrylic (co)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
    • C08J7/0427—Coating with only one layer of a composition containing a polymer binder
    • 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
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/04—Homopolymers or copolymers of esters
    • C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09D133/08—Homopolymers or copolymers of acrylic acid esters
    • 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
    • G02B1/14—Protective coatings, e.g. hard coatings
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • 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
    • C08J2433/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
    • C08J2433/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
    • C08J2433/06—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C08J2433/08—Homopolymers or copolymers of acrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K2201/00—Specific properties of additives
    • C08K2201/002—Physical properties
    • C08K2201/005—Additives being defined by their particle size in general

Definitions

  • the present invention relates to an organic-inorganic hybrid hard coating film and a polarizing plate including the same.
  • Hard coating films are widely used to protect panel surfaces of various flat panel displays such as liquid crystal displays (TFT-LCDs), plasma displays (PDPs), organic electroluminescent displays (OLEDs), and CRTs.
  • TFT-LCDs liquid crystal displays
  • PDPs plasma displays
  • OLEDs organic electroluminescent displays
  • CRTs CRTs
  • the display panel employing a glass substrate has a weak impact resistance and has a problem in weight reduction, so that a film having a hard coating layer having a high hardness on the surface of a plastic transparent substrate is widely used to replace or supplement the disadvantage.
  • Korean Patent Publication No. 2009-0044089 discloses a composition for forming an organic-inorganic hybrid hard coating layer including a urethane acrylate oligomer, a polyfunctional acrylate monomer, and a silica having a molecular weight of 500 to 10,000.
  • the hard coating film has a pencil hardness of only 2H to 3H level, the hard coating film does not have sufficient surface protection characteristics that the hard coating film should have. Therefore, the organic-inorganic hybrid hard coating film having excellent optical properties and excellent surface hardness and wear resistance is It is required.
  • An object of the present invention is to provide an organic-inorganic hybrid hard coating film having a high surface hardness and excellent scratch resistance and scratch resistance and a polarizing plate including the same.
  • the hard coating layer formed by applying a composition for forming a hard coating layer containing an acrylate-based resin having an average functional group of 5 to 15, inorganic particles having a UV reactive group and a photoinitiator on one surface of the transparent substrate film
  • the acrylate-based resin comprises at least 10% by weight of the tri-functional acrylate-based resin
  • the inorganic particles are characterized in that it comprises 80 to 120 parts by weight based on 100 parts by weight of acrylate-based resin It provides an organic-inorganic hybrid hard coating film.
  • the acrylate-based resin may have an average number of functional groups 6 to 14 functional.
  • the inorganic particles may have an average particle diameter of 1 to 100 nm.
  • the hard coating layer may have a thickness of 17 ⁇ 30 ⁇ m.
  • the hard coat film may have a surface hardness of 7H or more.
  • a polarizing plate including the organic-inorganic hybrid hard coating film.
  • the organic-inorganic hybrid hard coat film according to the present invention has a low haze and a high reflection sharpness, which is excellent in optical properties and has an excellent surface hardness, scratch resistance and scratch resistance.
  • the organic-inorganic hybrid hard coating film of the present invention is formed by applying a composition for forming a hard coating layer containing an acrylate-based resin having an average functional group of 5 to 15, inorganic particles having a UV reactive group, and a photoinitiator to one surface of a transparent substrate film. It comprises a hard coating layer, wherein the acrylate-based resin comprises at least 10% by weight of the tri- or less functional acrylate-based resin, the inorganic particles containing 80 to 120 parts by weight based on 100 parts by weight of the acrylate-based resin will be.
  • the composition for forming a hard coat layer includes an acrylate resin having an average functional group number of 5 to 15, an inorganic particle having a UV reactive group, and a photoinitiator.
  • the acrylate-based resin having an average functional number of 5 to 15 is a photocurable resin, and may include a photocurable (meth) acrylate oligomer and a monomer.
  • Urethane (meth) acrylate can manufacture the polyfunctional (meth) acrylate which has a hydroxyl group in a molecule, and the compound which has an isocyanate group in presence of a catalyst.
  • the (meth) acrylate having a hydroxy group in the molecule examples include 2-hydroxyethyl (meth) acrylate, 2-hydroxyisopropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, and capro It may be selected from one or more selected from the group consisting of lactone ring-opened hydroxyacrylate, pentaerythritol tri / tetra (meth) acrylate mixture, and dipentaerythritol penta / hexa (meth) acrylate mixture.
  • the compound having an isocyanate group include 1,4-diisocyanatobutane, 1,6-diisocyanatohexane, 1,8-diisocyanatooctane, 1,12-diisocyanatododecane, 1, 5-diisocyanato-2-methylpentane, trimethyl-1,6-diisocyanatohexane, 1,3-bis (isocyanatomethyl) cyclohexane, trans-1,4-cyclohexene diisocyanate, 4,4 '-Methylenebis (cyclohexyl isocyanate), isophorone diisocyanate, toluene-2,4-diisocyanate, toluene-2,6-diisocyanate, xylene-1,4-diisocyanate, tetramethylxylene-1, 3-diisocyanate, 1-chloromethyl-2,4-diisocyanate,
  • the monomer is usually used, and has a unsaturated group such as a (meth) acryloyl group, a vinyl group, a styryl group, an allyl group, etc. in a photocurable functional group, and a (meth) acryloyl group is more preferable especially.
  • the monomer having a (meth) acryloyl group examples include neopentyl glycol acrylate, 1,6-hexanediol (meth) acrylate, propylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, Dipropylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, trimethylol ethane tri (meth) acrylate, 1 , 2,4-cyclohexane tetra (meth) acrylate, pentaglycerol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol tri (meth) acrylate , Dipentaeryth
  • Illustrative acrylate resin is a photocurable (meth) acrylate oligomer, and monomers can be used individually or in combination of 2 or more, respectively.
  • the acrylate resin of this invention is 5-15 average functional groups. If the average number of functional groups is less than 5, there is a problem that it is difficult to exhibit sufficient hardness due to low curing density, and when the average number of functional groups is greater than 15, cracking occurs due to large curing shrinkage due to poor reactivity due to poor reactivity or hardening. there is a problem.
  • the acrylate resin of this invention contains 10% or more of trifunctional or less acrylate resins.
  • the trifunctional or less acrylate-based resin is included in less than 10% of the entire acrylate-based resin, there is a problem that the curing reactivity is low and it is difficult to exhibit sufficient hardness.
  • trifunctional acrylate resins examples include caprolactone acrylate, octyl acrylate, isooctyl acrylate, lauryl acrylate, ethoxyethoxyethyl acrylate stearyl acrylate and hexanediol diacrylate.
  • Dipropylene glycol diacrylate, tripropylene glycol diacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate, polyethylene glycol diacrylate, trimethylolpropane triacrylate and pentaerythritol triacrylate can be used. have.
  • Inorganic particles having a UV reactive group include metal oxides or sulfides, and specifically, titanium dioxide (rutile, rutile / anatase mixed crystal, anatase amorphous structure), silicon oxide, indium oxide, tin oxide, zirconium oxide, zinc oxide, sulfide It may be zinc.
  • Colloidal inorganic oxides may also be used, including colloidal titanium dioxide, colloidal alumina, colloidal zirconia, colloidal vanadia, colloidal chromia, colloidal iron oxide, colloidal tin oxide, or mixtures thereof, preferably Silica can be used.
  • the average particle diameter of an inorganic particle is 1-100 nm.
  • the average particle diameter of the particles is less than 1 nm, the hardness may be lowered, and when the average particle diameter is greater than 100 nm, transparency may be reduced.
  • 80-120 weight part of inorganic particles are contained with respect to 100 weight part of acrylate resins. If the inorganic material is less than 80 parts by weight based on the above, the hardness may be lowered. If it is more than 120 parts by weight, the reaction rate may decrease, and transparency may be reduced.
  • Photoinitiators can be used without limitation, those used in the art. Specifically 2-methyl-1- [4- (methylthio) phenyl] 2-morpholinepropanone-1, diphenyl ketone benzyldimethyl ketal, 2-hydroxy-2-methyl-1-phenyl-1-one, 4-hydroxycyclophenylketone, dimethoxy-2-phenylatetophenone, anthraquinone, fluorene, triphenylamine, carbazole, 3-methylacetophenone, 4-knoloacetophenone, 4,4-dimethoxy At least one selected from the group consisting of acetophenone, 4,4-diaminobenzophenone, 1-hydroxycyclohexylphenylketone, and benzophenone can be used.
  • the photoinitiator may be used in an amount of 0.1 to 10 parts by weight based on 100 parts by weight of the total composition for forming a hard coat layer. If the content of the photoinitiator is less than 0.1 parts by weight, the curing rate is slow, and if it exceeds 10 parts by weight, cracks may occur in the anti-glare hard coating layer due to over curing.
  • the composition for forming the hard coat layer may include a solvent.
  • the solvent can be used without limitation so long as it is known as a solvent of the composition for forming a coating layer in the art.
  • alcohols methanol, ethanol, isopropanol, butanol, methylcellulose, ethyl solusorb, etc.
  • ketones methyl ethyl ketone, methyl butyl ketone, methyl isobutyl ketone, diethyl ketone, dipropyl ketone, cyclohexa
  • At least one selected from the group consisting of rice paddy, etc. hexane-based (hexane, heptane, octane, and the like), and benzene-based (benzene, toluene, xylene, and the like).
  • the solvent may be included in an amount of 10 to 95 parts by weight based on 100 parts by weight of the total composition for forming the hard coat layer.
  • the viscosity may be high and workability may be reduced. have.
  • the present invention provides a hard coating film including a hard coating layer formed using the above-described composition for forming a hard coating layer. That is, the anti-glare film of the present invention includes a hard coating layer formed by applying a hard coating layer-forming composition to at least one surface of a transparent substrate and then curing the composition.
  • the transparent substrate is not particularly limited as long as it is a film having transparency.
  • the transparent substrate may be cycloolefin derivatives having a unit of a monomer including a cycloolefin such as norbornene or a polycyclic norbornene monomer, cellulose (diacetyl cellulose, triacetyl cellulose, acetyl cellulose butyrate, iso Butyl ester cellulose, propionyl cellulose, butyryl cellulose, acetyl propionyl cellulose), ethylene-vinyl acetate copolymer, polyester, polystyrene, polyamide, polyetherimide, polyacryl, polyimide, polyethersulfone, polysulfone, Polyethylene, polypropylene, polymethylpentene, polyvinyl chloride, polyvinylidene chloride, polyvinyl alcohol, polyvinyl acetal, polyether ketone, polyether ether ketone, polyether sulfone
  • the transparent substrate may have a thickness of about 8 ⁇ m to about 1000 ⁇ m, and preferably about 40 ⁇ m to about 100 ⁇ m.
  • the method of coating the antiglare layer forming composition on the transparent substrate is not particularly limited, and a method such as a die coater, an air knife, a reverse roll, a spray, a blade, a casting, a gravure, or a spin coating may be used.
  • the thickness after curing of the hard coat layer formed by the antiglare layer forming composition applied on the transparent substrate may be 17 to 30 ⁇ m preferably.
  • the curing step of the composition for forming a hard coating layer may be photocuring, wherein the irradiation amount of UV light may be about 0.01 ⁇ 10J / cm 2 , preferably 0.1 ⁇ 2J / cm 2 .
  • the hard coating layer manufactured through the above process may have a high hardness of 7H or more, and the organic-inorganic hybrid hard coating film including the hard coating layer may be included in a polarizing plate or a display device.
  • the present invention provides a polarizing plate equipped with an organic-inorganic hybrid hard coating film according to the present invention described above. That is, the polarizing plate of the present invention may be formed by laminating the anti-glare film according to the present invention described above on one side or both sides of a normal polarizer.
  • the polarizer may be provided with a protective film on at least one surface.
  • the hard coating layer-forming composition blended to have the composition and content (parts by weight) of Table 1 was filtered using a PP filter, and then cured on the upper surface of a triacetyl cellulose film (base film) having a thickness of 80 ⁇ m. It applied so that thickness might be 20 micrometers.
  • the content of the rake-based resin is calculated and shown in Table 2 below.
  • the hard coating layer-forming composition was applied onto an 80 ⁇ m triacetylcellulose (TAC) film, and then the solvent was dried for 2 minutes, and UV-cured at an accumulated light amount of 500 mJ / cm 2 to form a hard coating layer.
  • TAC triacetylcellulose
  • the thickness of the hard coating layer-forming composition and the hard coating layer after curing are used in Table 3 below.
  • JIS K5600 it measured using the Pencil Hardness Tester (pencil hardness tester, masonry science). After fixing the pencil at a load of 500g and an angle of 45, it was determined whether the surface was scratched visually by the pencil hardness.
  • Haze was measured using Suga's HZ-1 Haze Meter.
  • the transmission sharpness was determined by the sum of the transmission sharpness values of the slit intervals of 0.01 mm, 0.5 mm, 1.0 mm, and 2.0 mm.
  • the organic-inorganic hybrid hard coating film according to Examples 1 to 10 according to the present invention has excellent transparency and low haze, as well as excellent pencil hardness and scratch resistance.
  • Table 4 it is confirmed that the organic-inorganic hybrid hard coating film according to Examples 1 to 10 according to the present invention has excellent transparency and low haze, as well as excellent pencil hardness and scratch resistance.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Organic Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Laminated Bodies (AREA)
  • Paints Or Removers (AREA)
  • Surface Treatment Of Optical Elements (AREA)
  • Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)

Abstract

La présente invention concerne un film de revêtement dur hybride organique-inorganique, et plus particulièrement, un film de revêtement dur hybride organique-inorganique comprenant une couche de revêtement dur formée par revêtement d'une composition pour former une couche de revêtement dur comprenant une résine à base d'acrylate ayant un groupe fonctionnel moyen de 5 à 15, des particules inorganiques ayant un groupe fonctionnel réactif aux UV et un photoinitiateur sur un côté d'un film substrat transparent, la résine à base d'acrylate comprenant au moins 10 % en poids d'une résine à base d'acrylate ayant au moins 3 groupes fonctionnels, et des particules inorganiques étant comprises à 80 à 120 parties en poids sur la base de 100 parties en poids de la résine à base d'acrylate.
PCT/KR2013/011258 2012-12-13 2013-12-06 Film de revêtement dur hybride organique-inorganique, et plaque de polarisation le comprenant Ceased WO2014092388A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2012-0145210 2012-12-13
KR1020120145210A KR101959474B1 (ko) 2012-12-13 2012-12-13 유기-무기 하이브리드 하드코팅 필름 및 이를 포함하는 편광판

Publications (1)

Publication Number Publication Date
WO2014092388A1 true WO2014092388A1 (fr) 2014-06-19

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PCT/KR2013/011258 Ceased WO2014092388A1 (fr) 2012-12-13 2013-12-06 Film de revêtement dur hybride organique-inorganique, et plaque de polarisation le comprenant

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KR (1) KR101959474B1 (fr)
TW (1) TWI643910B (fr)
WO (1) WO2014092388A1 (fr)

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KR101650450B1 (ko) * 2014-07-21 2016-08-23 자동차부품연구원 하드코팅 조성물
KR102346783B1 (ko) * 2015-09-03 2022-01-03 동우 화인켐 주식회사 커버 윈도우 기판 및 이를 구비하는 화상표시장치
KR102346796B1 (ko) * 2015-09-03 2022-01-03 동우 화인켐 주식회사 커버 윈도우 기판 및 이의 제조 방법
US10391750B2 (en) 2015-09-03 2019-08-27 Dongwoo Fine-Chem Co., Ltd. Cover window plate and image display device including the same
KR102018561B1 (ko) * 2015-10-02 2019-09-06 동우 화인켐 주식회사 하드코팅 조성물 및 이를 이용한 하드코팅 필름
KR102502398B1 (ko) * 2015-12-14 2023-02-21 동우 화인켐 주식회사 하드코팅 형성용 조성물 및 이를 이용한 하드코팅 필름
KR102609848B1 (ko) * 2015-12-23 2023-12-05 동우 화인켐 주식회사 하드코팅 필름 및 이를 구비한 플렉시블 디스플레이

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KR101959474B1 (ko) 2019-03-18
TW201422730A (zh) 2014-06-16
TWI643910B (zh) 2018-12-11
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