WO2021106221A1 - 遮光用紫外線硬化性組成物、遮光膜、及び、遮光膜を有する物品を製造する方法 - Google Patents
遮光用紫外線硬化性組成物、遮光膜、及び、遮光膜を有する物品を製造する方法 Download PDFInfo
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- WO2021106221A1 WO2021106221A1 PCT/JP2019/046902 JP2019046902W WO2021106221A1 WO 2021106221 A1 WO2021106221 A1 WO 2021106221A1 JP 2019046902 W JP2019046902 W JP 2019046902W WO 2021106221 A1 WO2021106221 A1 WO 2021106221A1
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Classifications
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- C—CHEMISTRY; METALLURGY
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- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/61—Additives non-macromolecular inorganic
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/06—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation
- B05D3/061—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation using U.V.
- B05D3/065—After-treatment
- B05D3/067—Curing or cross-linking the coating
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- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
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- 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
-
- 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
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/66—Additives characterised by particle size
- C09D7/69—Particle size larger than 1000 nm
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
Definitions
- the present invention relates to a light-shielding UV-curable composition, a light-shielding film, and a method for producing an article having a light-shielding film.
- the light-shielding film provided in various display devices such as a liquid crystal display device may be formed by using a thermosetting type or ultraviolet curable type ink containing a black pigment such as carbon black (for example, Patent Document 1).
- the ultraviolet curable ink is more advantageous than the thermosetting ink in terms of suppressing damage to the peripheral member of the light-shielding film or the printing apparatus, printing accuracy, and the like.
- the light-shielding film containing carbon black has high light-shielding properties, it is difficult for the ultraviolet-curable composition (or ink) containing carbon black to have sufficient ultraviolet curability because carbon black substantially does not transmit ultraviolet rays. ..
- the ultraviolet-curable composition (or ink) containing carbon black By using an organic black pigment that transmits ultraviolet rays to some extent, improvement in ultraviolet curability is expected, but in that case, the light-shielding property of the light-shielding film tends to be insufficient.
- one aspect of the present invention provides a light-shielding UV-curable composition capable of forming a light-shielding film having sufficient UV curability and high light-shielding property.
- One aspect of the present invention provides an ultraviolet curable composition for shading, which comprises a photopolymerizable monoma, an organic black pigment, and a particulate light scattering material.
- Another aspect of the present invention provides a light-shielding film containing a cured product of the above-mentioned UV-curable composition for light-shielding.
- Yet another aspect of the present invention is to form a resin film containing the light-shielding ultraviolet-curable composition on a substrate, and to irradiate the resin film with ultraviolet rays to obtain the light-shielding ultraviolet-curable composition.
- a light-shielding film containing a cured product of an object and to produce an article having the light-shielding film, including.
- a light-shielding UV-curable composition capable of forming a light-shielding film having sufficient UV curability and high light-shielding property.
- (meth) acryloyl means methacryloyl or acryloyl. This also applies to other similar expressions.
- the UV curable composition for shading contains a photopolymerizable monoma, an organic black pigment, and a particulate light scattering material.
- This UV curable composition can be used to form a light-shielding film.
- the ultraviolet curable composition according to the present embodiment can be an ink (for example, an inkjet ink) for forming a light-shielding film by a printing method.
- the photopolymerizable monoma is composed of one or more compounds having one or more photopolymerizable functional groups.
- the photopolymerizable functional group may be an ethylenically unsaturated group.
- the photopolymerizable monoma may be a compound having one or more (meth) acryloyl groups.
- Compounds having a (meth) acryloyl group used as a polymerizable monoma are (meth) acrylic acid alkyl ester, (meth) acrylic acid, (meth) acrylamide, N-alkyl (meth) acrylamide, N, N-dialkyl (meth).
- Acrylamide or a combination of two or more selected from these, may be used, and the alkyl group contained in (meth) acrylic acid alkyl ester, N-alkyl (meth) acrylamide, and N, N-dialkyl (meth) acrylamide may be used.
- the photopolymerizable monoma may be liquid at room temperature (25 ° C.).
- the ultraviolet curable composition containing a liquid photopolymerizable monoma tends to have fluidity suitable for printing even in the absence of a solvent.
- the photopolymerizable monoma may be a monofunctional acrylic monoma having one (meth) acryloyl group, a polyfunctional acrylic monoma having two or more (meth) acryloyl groups, or a combination thereof.
- the monofunctional acrylic monoma is not particularly limited, and specific examples thereof include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, and tert-butyl (meth) acrylate. , N-Pentyl (meth) acrylate, n-hexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, dodecyl (meth) acrylate, and stearyl (meth).
- (Meta) acrylate having an alkyl group having 1 to 18 carbon atoms such as acrylate; 2-hydroxyethyl (meth) acrylate, 1-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl ( Meta) acrylate, 1-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 3-hydroxybutyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 1-hydroxybutyl (meth) acrylate, etc.
- (Meta) acrylate having a hydroxyl group glycidyl (meth) acrylate, ⁇ -ethylglycidyl (meth) acrylate, ⁇ -propyl glycidyl (meth) acrylate, ⁇ -butyl glycidyl (meth) acrylate, 2-methylglycidyl (meth) acrylate , 2-Ethylglycidyl (meth) acrylate, 2-propylglycidyl (meth) acrylate, 3,4-epoxybutyl (meth) acrylate, 3,4-epoxyheptyl (meth) acrylate, ⁇ -ethyl-6,7-epoxy (Meta) acrylates having a glycidyl group such as heptyl (meth) acrylate and 3,4-epoxycyclohexylmethyl (meth) acrylate; and cyclopentyl (meth) acryl
- the curable composition may contain a liquid photopolymerizable monoma and a polymer and / or oligoma.
- the polymer and oligoma may have a photopolymerizable group.
- polymers and oligomas having a photopolymerizable group are regarded as photopolymerizable monomas.
- the content of the photopolymerizable monoma may be 10% by mass or more, 20% by mass or more, 30% by mass or more, or 95% by mass or less, based on the mass of the ultraviolet curable composition.
- the content here means the total content of two or more compounds when they are used as photopolymerizable monomas.
- the UV curable composition for shading may further contain a photopolymerization initiator.
- the photopolymerization initiator is a compound that initiates the polymerization reaction of a photopolymerizable monoma by absorbing ultraviolet rays.
- the photopolymerization initiator can be, for example, a photoradical polymerization initiator or a photocationic polymerization initiator, and in particular, a photoradical polymerization initiator.
- the photopolymerization initiator may contain a compound showing a maximum value in the range of 300 to 400 nm in the absorption spectrum.
- a composition containing a photopolymerizable monoma, an organic black pigment, and a particulate light scattering material may be mixed with a photopolymerization initiator to produce a light-shielding ultraviolet curable composition.
- the photoradical polymerization initiator is not particularly limited, but may be, for example, an ⁇ -cleaving type compound or a hydrogen abstraction type compound, or a bimolecular radical polymerization initiator.
- photopolymerization initiators are benzophenone, 4-methylbenzophenone, N, N, N', N'-tetramethyl-4,4'-diaminobenzophenone (Michler ketone), N, N-tetraethyl-4,4'.
- the content of the photopolymerization initiator may be, for example, 0.1 to 10% by mass based on the mass of the ultraviolet curable composition.
- the content here means the total content of two or more compounds when they are used as photopolymerization initiators.
- the organic black pigment is a black particle containing an organic pigment, and can be selected from those usually used as a black pigment.
- the organic black pigment may be, for example, at least one selected from the group consisting of perylene-based pigments (perylene black), lactam-based pigments (lactam black), aniline black, cyanine black, lignin black, and RGB black.
- the average particle size (dispersed particle size) of the organic black pigment dispersed in the ultraviolet curable composition is not particularly limited, but may be, for example, 0.01 to 1.0 ⁇ m.
- the content of the organic black pigment may be 0.5% by mass or more, or 1.0% by mass or more, based on the mass of the ultraviolet curable composition, from the viewpoint of appropriate light-shielding properties of the light-shielding film. It may be 50% by mass or less.
- the content here means the total content of two or more kinds of organic black pigments when they are used.
- the light scattering material is composed of a plurality of particles. Usually, these plurality of particles are dispersed in the UV curable composition.
- the average particle size of the light scattering material may be 0.05 ⁇ m or more, 5.0 ⁇ m or less, 4.0 ⁇ m or less, 3.0 ⁇ m or less, 2.0 ⁇ m or less, or 1.0 ⁇ m or less. From the viewpoint of appropriate light-shielding properties of the light-shielding film, the average particle size of the light scattering material may be 0.1 to 1.0 ⁇ m.
- the average particle size of the light scattering material may be a value obtained from a volume-based particle size distribution obtained by a laser diffraction / scattering method.
- the light scattering material may contain, for example, silicone particles, silica particles, or a combination thereof.
- the light scattering material may include silicone particles and other particles selected from silica particles, alumina particles, and titanium oxide particles. Part or all of the light scattering material may be hollow particles.
- the silicone particles are particles containing silicone having a polysiloxane chain, and the silicone may have a structure in which the polysiloxane chains are crosslinked, or may be polyorganosylsesquioxane.
- the silicone particles may be composite particles having a silicone-containing nuclear particle having a polysiloxane chain and a film containing a polyorganosylsesquioxane formed on the surface of the nuclear particle.
- the content of the light scattering material may be 0.5% by mass or more or 1.0% by mass or more based on the mass of the ultraviolet curable composition, 10% by mass or less, 9.0% by mass or less, 8 It may be 0.0% by mass or less, 7.0% by mass or less, 6.0% by mass or less, 5.0% by mass or less, or 4.0% by mass or less.
- the content here means the total content of two or more kinds of light scattering materials when they are used.
- the UV curable composition may be a solvent-free composition that does not substantially contain a solvent. More specifically, the content of the solvent may be 1.0% by mass or less, or 0% by mass, based on the mass of the ultraviolet curable composition.
- a composition (ink) substantially free of a solvent is advantageous in, for example, preventing damage to members around the light-shielding film, preventing damage to the printing apparatus, and forming a highly accurate light-shielding film.
- the cured film formed by curing the film of the ultraviolet curable composition has high light-shielding properties.
- the OD value (optical density) of the formed cured film may be 1.5 or more, 2.0 or more, or 2.5 or more.
- the OD value here is a value calculated from the average transmittance of a cured film having a thickness of 130 ⁇ m ⁇ 5 ⁇ m with respect to light having a wavelength of 400 to 700 nm.
- Various articles having a light-shielding film can be produced by using the ultraviolet curable composition according to the above-exemplified embodiment.
- One embodiment of the method for producing an article having a light-shielding film is to form a resin film containing an ultraviolet curable composition on a substrate and to irradiate the resin film with ultraviolet rays to form an ultraviolet curable composition. It includes forming a light-shielding film which is a cured product.
- the resin film may be formed by printing using the ultraviolet curable composition as an ink (for example, inkjet printing).
- the wavelength of ultraviolet rays for curing the ultraviolet curable composition forming the resin film may be 300 to 400 nm.
- the thickness of the resin film (light-shielding film) may be, for example, 20 to 1000 ⁇ m.
- Examples of articles having a light-shielding film include an image display device, an optical sensor, and a lens.
- Photopolymerizable monoma 4-hydroxybutyl acrylate (4-HBA) 1-4.
- Photoradical polymerization initiator 1-hydroxycyclohexylphenyl ketone (manufactured by BASF, product name: Irgacure-184) 4-Methylbenzophenone (manufactured by Sort Co., Ltd., product name: SB-PI712)
- UV curable composition (ink)
- Example 1 3.0 parts by mass of the lactam pigment was dispersed in 91.7 parts by mass of 4-hydroxybutyl acrylate to obtain a dispersion having a dispersion particle size of the lactam pigment of 0.17 ⁇ m.
- To this dispersion 2.0 parts by mass of silicone particles (X-52-854), 3.0 parts by mass of 1-hydroxycyclohexylphenyl ketone (Irgacure-184), and 0.3 of 4-methylbenzophenone (SB-PI712).
- a mass portion was added, and the mixed solution was stirred with a self-revolving mixer (Shinky Co., Ltd., product name: ARE-250) at a rotation speed of 2,000 rpm for 5 minutes to obtain an ultraviolet curable composition.
- a self-revolving mixer (Shinky Co., Ltd., product name: ARE-250) at a rotation speed of 2,000 rpm for 5 minutes to obtain an ultraviolet curable composition.
- Examples 2 to 8 and Comparative Examples 1 to 3 An ultraviolet curable composition was prepared in the same manner as in Example 1 except that each material and blending amount were changed as shown in Table 1.
- the resin film is cured by irradiating ultraviolet rays (3,000 mJ / cm 2 ) from the protective film side using an ultraviolet irradiation device (Metal halide lamp manufactured by Eye Graphics Co., Ltd.) to cure the ultraviolet curable resin composition.
- An ultraviolet irradiation device Metal halide lamp manufactured by Eye Graphics Co., Ltd.
- a laminated film having a light-shielding film (thickness of about 130 ⁇ m) was obtained.
- Evaluation 4-1 Reaction rate (ultraviolet curability) About 1 g of each ultraviolet curable composition of Examples and Comparative Examples was dropped onto a glass plate to form a resin film as a measurement sample before UV irradiation. The infrared absorption spectrum of the formed resin film was measured using a Fourier transform infrared spectrophotometer (manufactured by Shimadzu Corporation, product name: IR Spirit (QATR-S unit)) in an environment at room temperature (25 ° C) with a resolution of 2 cm. -1 , integration: Measured by the ATR method under the condition of 64 times.
- a measurement sample having a size of 10 mm ⁇ 10 mm was cut out from the laminated film having a light-shielding film, and the protective film was peeled off from the measurement sample.
- the exposed light-shielding film was attached to a glass plate, and then the support film was peeled off from the light-shielding film.
- the infrared absorption spectrum of the exposed light-shielding film was measured by the same method as described above.
- acryloyl is obtained by the following formula.
- OD value light shielding property
- a haze meter manufactured by Nippon Denshoku Kogyo Co., Ltd., product name: SH7000
- the transmittance of a light-shielding film having a size of 40 mm ⁇ 50 mm is measured at each wavelength of 5 nm from 400 nm to 700 nm. It was measured.
- the OD value was calculated from the average value C of the transmittance at each wavelength by the following formula.
- a large OD value means that the light-shielding film has a high shielding property (light-shielding property) with respect to visible light.
- OD value -Log 10 (C / 100)
- the ultraviolet curable composition of each example was cured by ultraviolet irradiation with good curability and formed a light-shielding film having sufficiently high light-shielding property.
- the light-shielding film formed from the ultraviolet-curable composition of Comparative Example 1 containing an organic black pigment and not a light-scattering material had low light-shielding properties.
- the ultraviolet curable composition of Comparative Example 2 containing carbon black formed a light-shielding film having a high light-shielding property, but was insufficient in terms of curability.
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Priority Applications (5)
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KR1020227020515A KR20220106151A (ko) | 2019-11-29 | 2019-11-29 | 차광용 자외선 경화성 조성물, 차광막, 및, 차광막을 갖는 물품을 제조하는 방법 |
PCT/JP2019/046902 WO2021106221A1 (ja) | 2019-11-29 | 2019-11-29 | 遮光用紫外線硬化性組成物、遮光膜、及び、遮光膜を有する物品を製造する方法 |
CN201980102453.6A CN114730027A (zh) | 2019-11-29 | 2019-11-29 | 遮光用紫外线固化性组合物、遮光膜及制造具有遮光膜的物品的方法 |
JP2021561132A JP7414076B2 (ja) | 2019-11-29 | 2019-11-29 | 遮光用紫外線硬化性組成物、遮光膜、及び、遮光膜を有する物品を製造する方法 |
TW109141489A TW202124460A (zh) | 2019-11-29 | 2020-11-26 | 遮光用紫外線固化性組成物、遮光膜及製造具有遮光膜之物品之方法 |
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KR20130021128A (ko) * | 2011-08-22 | 2013-03-05 | 성균관대학교산학협력단 | 흑색 감광성 수지 조성물 및 이를 구비한 화상표시장치 |
WO2015159370A1 (ja) * | 2014-04-15 | 2015-10-22 | 三菱化学株式会社 | 遮光材付き基板、カラーフィルタ及び液晶表示装置並びにこの遮光材を形成するための着色樹脂組成物 |
WO2017110939A1 (ja) * | 2015-12-25 | 2017-06-29 | 旭硝子株式会社 | 光学フィルタおよび光学装置 |
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JP7396786B2 (ja) | 2017-02-24 | 2023-12-12 | 日鉄ケミカル&マテリアル株式会社 | 遮光膜用の感光性樹脂組成物、遮光膜、液晶表示装置、スペーサー機能を有する遮光膜の製造方法、および液晶表示装置の製造方法 |
JP2018155878A (ja) | 2017-03-16 | 2018-10-04 | 三菱ケミカル株式会社 | 着色感光性樹脂組成物、硬化物、有機電界発光素子、画像表示装置及び照明 |
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- 2019-11-29 CN CN201980102453.6A patent/CN114730027A/zh active Pending
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KR20130021128A (ko) * | 2011-08-22 | 2013-03-05 | 성균관대학교산학협력단 | 흑색 감광성 수지 조성물 및 이를 구비한 화상표시장치 |
WO2015159370A1 (ja) * | 2014-04-15 | 2015-10-22 | 三菱化学株式会社 | 遮光材付き基板、カラーフィルタ及び液晶表示装置並びにこの遮光材を形成するための着色樹脂組成物 |
WO2017110939A1 (ja) * | 2015-12-25 | 2017-06-29 | 旭硝子株式会社 | 光学フィルタおよび光学装置 |
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CN114730027A (zh) | 2022-07-08 |
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