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WO2023121162A1 - Composition hybride organique/inorganique et film adhésif la comprenant - Google Patents

Composition hybride organique/inorganique et film adhésif la comprenant Download PDF

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Publication number
WO2023121162A1
WO2023121162A1 PCT/KR2022/020668 KR2022020668W WO2023121162A1 WO 2023121162 A1 WO2023121162 A1 WO 2023121162A1 KR 2022020668 W KR2022020668 W KR 2022020668W WO 2023121162 A1 WO2023121162 A1 WO 2023121162A1
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WO
WIPO (PCT)
Prior art keywords
group
silane
composition
organic
weight
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/KR2022/020668
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English (en)
Korean (ko)
Inventor
염진석
김석조
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.)
KCTech Co Ltd
Original Assignee
KCTech 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 KCTech Co Ltd filed Critical KCTech Co Ltd
Priority to CN202280072039.7A priority Critical patent/CN118159575A/zh
Priority to JP2024529663A priority patent/JP7763343B2/ja
Publication of WO2023121162A1 publication Critical patent/WO2023121162A1/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
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • 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
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • 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
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • 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
    • C08K9/00—Use of pretreated ingredients
    • C08K9/04—Ingredients treated with organic substances
    • C08K9/06—Ingredients treated with organic substances with silicon-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/10—Adhesives in the form of films or foils without carriers
    • 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
    • C08K2201/006—Additives being defined by their surface area

Definitions

  • the present invention relates to an organic-inorganic hybrid composition and an adhesive film containing the same.
  • OCA film is a transparent adhesive film used for bonding optical members.
  • OCA optically clear adhesive
  • a display device having a touch panel typically includes a display panel such as a liquid crystal panel, a touch panel body having a transparent conductive film made of indium tin oxide (ITO) on a surface layer, and an optical member such as a cover panel that protects the transparent conductive film.
  • ITO indium tin oxide
  • an optical member such as a cover panel that protects the transparent conductive film.
  • optically transparent adhesives include those made of organic materials such as silicone-based resins, polyurethane-based resins, and olefin-based resins. Differences can cause problems affecting optical properties.
  • the present invention is to provide a surface treatment agent for organic-inorganic hybrid composition.
  • an organic-inorganic hybrid composition According to one embodiment of the present invention, it is intended to provide an organic-inorganic hybrid composition.
  • An organic-inorganic hybrid composition according to an embodiment of the present invention includes inorganic particles surface-modified by a surface treatment agent and an acrylic monomer, and the surface-modified inorganic particles and acrylic monomer have a weight ratio of 1:1 to 2:1. may have
  • the inorganic particles are ZrO 2 , SiO 2 , Al 2 O 3 , CeO 2 , ZnO, V 2 O 5 TiO 2 , BaTiO 3 , SrTiO 3 , BaTiO 3 , PbTiO 3 , PbZrO 3 , Pb ( Zr,Ti)O 3 (PZT), Pb 1-x La x Zr 1-y Ti y O 3 (PLZT), (1-x)Pb(Mg 1/3 Nb 2/3 )O 3 -xPbTiO 3 ( PMN-PT), HfO 2 and may include at least one selected from the group consisting of BN.
  • the diameter of the inorganic particles may be 10 nm to 200 nm, and the specific surface area of the inorganic particles may be 1 m 2 /g to 250 m 2 /g.
  • the surface-modified inorganic particles may be 40% to 50% by weight of the composition.
  • the acrylic monomer is butyl acrylate, 2-ethylhexyl acrylate, isobornyl acrylate and 4-acryloyl morpholine (4-ethylhexyl acrylate).
  • acryloyl morpholine may include at least one selected from the group consisting of.
  • the acrylic monomer may be 50% to 60% by weight of the composition.
  • the surface treatment agent may be a copolymer of a silane-based monomer and a methacrylate-based monomer.
  • the silane-based monomer is silane, C 1 -C 20 Alkyl silane, alkoxy silane, isocyanate silane, amino silane, epoxy silane, acryl silane, mercapto silane, fluorine silane, methacryloxy group silane, It includes at least one selected from the group consisting of vinyl silane, phenyl silane, chloro silane, and silazane, and the methacrylate-based monomer is 2-hydroxyethyl methacrylate (2-HEMA), At least one selected from the group consisting of 2-hydroxypropyl methacrylate (2-HPMA) and 2-hydroxy-1-methylethyl methacrylate may include
  • the surface treatment agent may include a compound represented by any one of Formulas 1 to 3 below.
  • R 1 to R 3 are, respectively, H, a saturated or unsaturated straight-chain or branched-chain C 1 -C 20 alkyl group, a hydroxyl group, a silane group, and at least one of an alkoxysilane group, wherein R 4 is , H or containing a hydroxyl group.
  • the surface treatment agent may be included in an amount of 10 parts by weight to 30 parts by weight based on 100 parts by weight of the inorganic particles.
  • the composition may further include a dispersant including at least one functional group selected from the group consisting of a carboxyl group, a phosphoric acid group, a phosphonic acid group, a sulfonic acid group, and a phenolic hydroxyl group.
  • a dispersant including at least one functional group selected from the group consisting of a carboxyl group, a phosphoric acid group, a phosphonic acid group, a sulfonic acid group, and a phenolic hydroxyl group.
  • the dispersant may be included in 1 part by weight to 10 parts by weight based on 100 parts by weight of the composition.
  • the composition further comprises a dispersing solvent
  • the dispersing solvent is methyl ethyl ketone (MEK), ethanol, methanol, acetonitrile (acetonitrile), toluene (Toluene), tetrahydrofuran (tetrahydrofuran) , THF), propylene glycol monoethyl ether acetate (PGMEA), and may include at least one selected from the group consisting of ethyl acetate.
  • the weight ratio of the surface-modified inorganic particles and the dispersion solvent may be 1:1 to 1:2.
  • the dispersion solvent may be 30% to 60% by weight of the composition.
  • the composition may have a refractive index of 1.50 to 1.80, a viscosity of 180 cPs to 250 cPs, and a haze of 15% or less.
  • An adhesive film according to another embodiment of the present invention is an adhesive film prepared using a composition, wherein the composition includes inorganic particles and acrylic monomers surface-modified by a surface treatment agent, and the surface-modified inorganic particles and acrylic monomers are , 1: 1 to 2: may have a weight ratio of 1.
  • the present invention may provide a surface treatment agent for an organic-inorganic hybrid composition.
  • an organic-inorganic hybrid composition may be provided.
  • first, second, A, B, (a), (b) may be used. These terms are only used to distinguish the component from other components, and the nature, sequence, or order of the corresponding component is not limited by the term.
  • the organic-inorganic hybrid composition according to an embodiment of the present invention may include inorganic particles surface-modified by a surface treatment agent and an acrylic monomer.
  • an adhesive film may be formed by curing the organic-inorganic hybrid composition, and according to the present invention, the organic-inorganic hybrid composition may provide an optically transparent or substantially optically transparent inorganic particle dispersion composition. .
  • the surface of the inorganic particles may be modified using a surface treatment agent to improve the dispersibility of the inorganic particles, and as they are evenly dispersed in the composition, an optically transparent inorganic particle dispersion composition may be provided.
  • the surface-modified inorganic particles and the acrylic monomer may have a weight ratio of 1:1 to 2:1. According to one embodiment, it may be preferable that the weight of the acrylic monomer is equal to or greater than the weight of the surface-modified inorganic particles.
  • the inorganic particle may be a metal oxide.
  • the inorganic particles are metal oxides and may be included in a transparent polymer resin to increase refractive index.
  • the inorganic particles are ZrO 2 , SiO 2 , Al 2 O 3 , CeO 2 , ZnO, V 2 O 5 TiO 2 , BaTiO 3 , SrTiO 3 , BaTiO 3 , PbTiO 3 , PbZrO 3 , Pb(Zr ,Ti)O 3 (PZT), Pb 1-x La x Zr 1-y Ti y O 3 (PLZT), (1-x)Pb(Mg 1/3 Nb 2/3 )O 3 -xPbTiO 3 (PMN -PT), HfO 2 It may include at least one selected from the group consisting of and BN.
  • the inorganic particles may preferably include zirconia (ZrO 2 ).
  • Zirconia may be suitable for the composition according to an embodiment of the present invention because it is transparent, has a high Abbe number, and has excellent mechanical strength and thermal stability.
  • the inorganic particles may correspond to nano-inorganic particles.
  • the diameter of the inorganic particles may be 10 nm to 200 nm.
  • the diameter of the inorganic particles may mean an average of the diameters of the inorganic particles.
  • the diameter of the inorganic particle may mean the diameter of the inorganic particle whose surface is not modified with a surface treatment agent.
  • the diameter of the inorganic particles is 10 nm or more, 20 nm or more, 30 nm or more, 40 nm or more, 50 nm or more, 60 nm or more, 70 nm or more, 80 nm or more, 90 nm or more, 100 nm or more.
  • the diameter of the inorganic particles when the diameter of the inorganic particles is less than 10 nm, dispersion may be difficult due to the increase in the surface energy of the inorganic particles, and when the diameter is greater than 200 nm, a scattering effect is developed, resulting in deterioration in the visibility of the adhesive film. Thickness may increase.
  • the specific surface area of the inorganic particles may be 1 m 2 /g to 250 m 2 /g.
  • the specific surface area of the inorganic particles may mean the average of the specific surface areas of the inorganic particles.
  • the specific surface area of the inorganic particles may be a measurement of the specific surface area of inorganic particles that are not surface-modified with a surface treatment agent.
  • the specific surface area of the inorganic particles is 1 m 2 /g or more, 10 m 2 /g or more, 30 m 2 /g or more, 50 m 2 /g or more, 70 m 2 /g or more, or 90 m 2 /g or more.
  • transmittance when the specific surface area of the inorganic particles is out of the above range, transmittance may be lowered or quality may be deteriorated due to scattering, and agglomerates may be formed.
  • the surface-modified inorganic particles may be 40% to 50% by weight of the composition. According to one embodiment, the amount of the surface-modified inorganic particles may be 40% to 45% by weight, or 45% to 50% by weight.
  • the relative ratio of the inorganic particles in the composition is lowered, thereby reducing the refractive index and luminance of the composition. Cloudiness may occur during manufacturing.
  • the acrylic monomer is butyl acrylate, 2-ethylhexyl acrylate, isobonyl acrylate and 4-acryloyl morpholine (4-ethylhexyl acrylate).
  • acryloyl morpholine may include at least one selected from the group consisting of.
  • An adhesive film may be prepared by curing the composition according to an embodiment of the present invention, and a flexible and optically excellent adhesive film may be prepared by applying an acrylic monomer.
  • the acrylic monomer may be 50% to 60% by weight of the composition. According to one embodiment, the acrylic monomer may be 50% to 55% by weight, or 55% to 60% by weight.
  • the ratio of inorganic particles increases and the viscosity may increase. , cloudiness may occur.
  • the surface treatment agent may be a copolymer of a silane-based monomer and a methacrylate-based monomer.
  • the surface treatment agent may be a random copolymer of a silane-based monomer and a methacrylate-based monomer.
  • the silane-based monomer is silane, C 1 -C 20 Alkyl silane, alkoxy silane, isocyanate silane, amino silane, epoxy silane, acryl silane, mercapto silane, fluorine silane, methacryloxy group silane, It may include at least one selected from the group consisting of vinyl silane, phenyl silane, chloro silane, and silazane.
  • the silane-based monomer is, specifically, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane (vinyltris (2-methoxyethoxy)) silane) containing at least one vinyl group-containing silane-based monomer selected from the group consisting of 3-methacryloxypropyltrimethoxysilane (MPTMS), 3-methacryloxypropyltriethoxysilane (3 -Methacryloxypropyltriethoxysilane (MPTES), 3-methacryloxypropylmethyldimethoxysilane, and 3-methacryloxypropylmethyldiethoxysilane (methacryloxypropylmethyldiethoxysilane).
  • MPTMS 3-methacryloxypropyltrimethoxysilane
  • MPTES 3-methacryloxypropyltriethoxysilane
  • 3-methacryloxypropylmethyldimethoxysilane 3-methacryloxypropyl
  • Silane-based monomers containing an oxy group silane-based monomers containing an acetoxy group including vinyltriacetoxysilane, 3-acryloxypropyltrimethoxysilane (APTMS), 3-acryloxypropyltriene Toxysilane (3-acryloxypropyltriethoxysilane) or an acryloxy group-containing silane-based monomer including the two, 3-glycidoxypropyltrimethoxysilane (GPTMS), 3-glycidoxypropyltriethoxysilane ( 3-glycidoxypropyltriethoxysilane (GPTES), 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2-(3,4-epoxycyclohexyl)
  • the methacrylate-based monomer is 2-hydroxyethyl methacrylate (2-HEMA), 2-hydroxypropyl methacrylate (2-hydroxypropyl methacrylate, 2-HPMA) , 2-hydroxy-1-methylethyl methacrylate (2-hydroxy-1-methylethyl methacrylate) may include at least one selected from the group consisting of.
  • the surface treatment agent may include a compound represented by any one of Formulas 1 to 3 below.
  • the R 1 to R 3 are, respectively, H, a saturated or unsaturated straight or branched chain C 1 -C 20 alkyl group, a hydroxyl group, a silane group and an alkoxysilane group including at least one of, wherein the R 4 may contain H or a hydroxyl group.
  • R 1 to R 3 are, respectively, a C 2 -C 12 alkyltrimethoxysilane group, a C 2 -C 12 alkyltriethoxysilane group and a C 2 -C 12 It may include at least one selected from the group consisting of an alkyldimethoxyethoxysilane group.
  • R1 to R3 are ethyltrimethoxysilane, propyltrimethoxysilane, butyltrimethoxysilane, pentyltrimethoxysilane, hexyltrimethoxysilane, heptyltrimethoxy, respectively.
  • Silane group octyltrimethoxysilane group, nonyltrimethoxysilane group, decyltrimethoxysilane group, undecyltrimethoxysilane group, dodecyltrimethoxysilane group, ethyltriethoxysilane group, propyl trie Toxysilane group, butyltriethoxysilane group, pentyltriethoxysilane group, hexyltriethoxysilane group, heptyltriethoxysilane group, octyltriethoxysilane group, nonyltriethoxysilane group, decyltriethoxy Silane group, undecyltriethoxysilane group, dodecyltriethoxysilane group, ethyldimethoxyethoxysilane group, propyldimethoxyethoxysilane group, butyldimethoxy
  • R 4 may be one in which an H atom or a hydroxyl group is formed at the opposite end of the portion connected to the methacrylic group.
  • R 4 may include at least one selected from the group consisting of H, a 2-hydroxyethyl group, a 3-hydroxypropyl group, and a 2-hydroxybutyl group.
  • the surface treatment agent may be a copolymer of two different methacrylate-based monomers, a copolymer of an acrylate-based monomer and a methacrylate-based monomer, or a copolymer of an epoxy-based monomer and a methacrylate-based monomer.
  • the surface treatment agent for a composition including a compound represented by any one of Formulas 1 to 3 may have characteristics of the surface treatment agent determined according to the ratio of m and n.
  • m and n may have an integer ratio between 1:2 and 2:1.
  • m and n may have an integer ratio such as 1:1, 3:2, 2:3, 4:3, 5:3, 3:4, 5:4, or 7:4.
  • the surface treatment agent may be included in an amount of 10 parts by weight to 30 parts by weight based on 100 parts by weight of the inorganic particles. According to one embodiment, when the amount of the surface treatment agent is less than 10 parts by weight based on 100 parts by weight of the inorganic particles, dispersibility may be lowered, and when it is greater than 30 parts by weight, curing may not be smooth during film manufacture.
  • the surface treatment agent may further include at least one polymerization initiator selected from the group consisting of benzoyl peroxide (BPO), azobisisobutyronitrile (AIBN), and AIBA (2,2'-azobis (2-methylpropionamidine)).
  • the polymerization initiator may include a peroxide-based compound, an azo compound, or both.
  • the polymerization initiator may be 0.1% to 1% by weight of the surface treatment agent. According to one embodiment, when the polymerization initiator is less than 0.1% by weight, copolymerization may proceed partially, and when the content of the polymerization initiator exceeds 1% by weight, the excess polymerization initiator in the surface treatment agent is distributed and functions as an impurity can do.
  • the light transmittance of the surface treatment agent may be 40% or more.
  • the light transmittance of the surface treatment agent may be 40% or more, 42% or more, 45% or more, or 50% or more.
  • the haze of the surface treatment agent may be 80% or less.
  • the haze of the surface treatment agent may be 80% or less, 70% or less, 60% or less, or 50% or less.
  • the composition may further include a dispersant including at least one functional group selected from the group consisting of a carboxyl group, a phosphoric acid group, a phosphonic acid group, a sulfonic acid group, and a phenolic hydroxyl group.
  • the dispersant may preferably include a carboxyl group.
  • the dispersant may be available from a commercial product.
  • the dispersant is a dispersant under the trade names DISPERBYK, DISPERBYK-101, DISPERBYK-102, DISPERBYK-103, DISPERBYK-106, DISPERBYK-107, DISPERBYK-108, DISPERBYK-109, DISPERBYK-110.
  • DISPERBYK-111 DISPERBYK-112, DISPERBYK-115, DISPERBYK-116, DISPERBYK-118, DISPERBYK-130, DISPERBYK-140, DISPERBYK-142, DISPERBYK-145, DISPERBYK-160, DISPERBYK-161, DISPERBYK-162, DISPERBYK -163, DISPERBYK-164, DISPERBYK-165, DISPERBYK-166, DISPERBYK-167, DISPERBYK-168, DISPERBYK-169, DISPERBYK-170, DISPERBYK-171, DISPERBYK-174, DISPERBYK-176, DISPERBYK-180, DISPERBYK-181 , DISPERBYK-182, DISPERBYK-183, DISPERBYK-184, DISPERBYK-
  • the dispersant in addition to the above trademark, Antiterra-U, P104, Disperbyk 110, Disperbyk 130, Disperbyk 160, Disperbyk 170 Family, EFKA 776, EFKA 4050, EFKA 4063, EFKA 4051, Solsperse 24000, It may include at least one selected from the group consisting of Solsperse 36600, Solsperse 32600, Solsperse 22000 and Solsperse 5000.
  • the dispersant may be included in an amount of 1 part by weight to 10 parts by weight based on 100 parts by weight of the composition. According to one embodiment, the dispersant may be included in 1 part by weight to 5 parts by weight, or 3 parts by weight to 7 parts by weight based on 100 parts by weight of the composition.
  • the composition further comprises a dispersing solvent
  • the dispersing solvent is methyl ethyl ketone (MEK), ethanol, methanol, acetonitrile (acetonitrile), toluene (Toluene), tetrahydrofuran (tetrahydrofuran) , THF), propylene glycol monomethyl ether acetate (PGMEA), and at least one selected from the group consisting of ethyl acetate.
  • the weight of the dispersion solvent may be equal to or greater than the weight of the surface-modified inorganic particles. According to one embodiment, the weight ratio of the surface-modified inorganic particles and the dispersion solvent may be 1:1 to 1:2.
  • the dispersion solvent may be 30% to 60% by weight of the composition. According to one embodiment, the dispersion solvent is 30% by weight or more, 40% by weight or more, or 50% by weight or more, 60% by weight or less, 50% by weight or less, 40% by weight or less, or selected from the above-mentioned values. It can be included in the range between the two values.
  • the refractive index of the composition may be 1.50 to 1.80.
  • the composition is a high refractive index dispersion composition, wherein the refractive index is 1.50 or more, 1.55 or more, 1.60 or more, 1.65 or more, 1.70 or more, or 1.75 or more, or 1.80 or less, 1.75 or less, 1.70 or less, 1.65 or less, 1.60 or less. or less, 1.55 or less, or may be included in a range between two values selected from the above-mentioned numerical values.
  • the composition may have a viscosity of 180 cPs to 20,000 cPs (at 25° C.).
  • the viscosity of the composition can be adjusted through a viscosity modifier such as MEK, toluene, or ethyl acetate.
  • the viscosity of the composition is preferably , 180 cPs to 10,000 cPs (based on 25 ° C.), and more preferably, 180 cPs to 1,000 cPs (based on 25 ° C.).
  • the haze of the composition may be 15% or less.
  • the haze of the composition may be 15% or less, preferably, 14% or less, and more preferably, 6% or less.
  • An adhesive film according to an embodiment of the present invention may be manufactured using a composition according to an embodiment.
  • An adhesive film according to an embodiment of the present invention is a composition according to an embodiment, and includes inorganic particles surface-modified by a surface treatment agent, and an acrylic monomer, wherein the inorganic particles and the acrylic monomer have a ratio of 1:1 to 2. : It may be prepared using a composition having a weight ratio of 1.
  • the adhesive film may be, for example, an OCA film or a pressure sensitive adhesive (PSA) film, and may provide a flexible and optically transparent adhesive film.
  • PSA pressure sensitive adhesive
  • 3-methacryloxypropyltrimethoxysilane (MPTMS) and 2-hydroxyethyl methacrylate (2-HEMA) were mixed at a weight ratio of 1:1 in methyl ethyl ketone (MEK) solvent.
  • AIBN methyl ethyl ketone
  • the solvent was mixed in the same amount as the total weight of the monomers. After growing at 60° C. for 3 hours under a nitrogen atmosphere, the mixture was stirred at room temperature for 12 hours to polymerize the monomers to obtain a polymer.
  • Example 1-1 except for using 2-hydroxyethyl acrylate (2-HEA) instead of 2-HEMA, the rest of the polymer was obtained in the same manner.
  • 2-HEA 2-hydroxyethyl acrylate
  • Example 1-1 except for using 2-hydroxybutyl acrylate (2-HBA) instead of 2-HEMA, the rest of the polymer was obtained in the same manner.
  • 2-HBA 2-hydroxybutyl acrylate
  • Example 2-1 an inorganic particle dispersion was prepared in the same manner as in Example 2-1, except that 30 parts by weight of the surface treatment agent was added based on 100 parts by weight of the zirconia powder.
  • Example 2-1 an inorganic particle dispersion was prepared in the same manner as in Example 2-1, except for adding 40 parts by weight of the surface treatment agent based on 100 parts by weight of the zirconia powder.
  • Example 2-1 an inorganic particle dispersion was prepared in the same manner as in Example 2-1, except for adding the polymer according to Comparative Example 1-1 as a surface treatment agent.
  • Comparative Example 2-1 an inorganic particle dispersion was prepared in the same manner as in Comparative Example 2-1, except that 30 parts by weight of the surface treatment agent was added based on 100 parts by weight of the zirconia powder.
  • Comparative Example 2-1 an inorganic particle dispersion was prepared in the same manner as in Comparative Example 2-1, except that 40 parts by weight of the surface treatment agent was added based on 100 parts by weight of the zirconia powder.
  • An inorganic particle dispersion was prepared in the same manner as in Example 2-1, except for adding the polymer according to Comparative Example 1-2 as a surface treatment agent.
  • Comparative Examples 2-4 an inorganic particle dispersion was prepared in the same manner as in Comparative Examples 2-4, except that 30 parts by weight of the surface treatment agent was added based on 100 parts by weight of the zirconia powder.
  • Comparative Examples 2-4 an inorganic particle dispersion was prepared in the same manner as in Comparative Examples 2-4, except that 40 parts by weight of the surface treatment agent was added based on 100 parts by weight of the zirconia powder.
  • Comparative Examples 2-7 an inorganic particle dispersion was prepared in the same manner as in Comparative Examples 2-7, except that 15 parts by weight of the surface treatment agent was added based on 100 parts by weight of the zirconia powder.
  • inorganic particle dispersions were prepared in the same manner as in Comparative Examples 2-7, except that 20 parts by weight of the surface treatment agent was added based on 100 parts by weight of the zirconia powder.
  • Example 2-1 40.77 48.25 97
  • Example 2-2 40.43 48.70 98 Example 2-3 58.41 23.45 97
  • Comparative Example 2-1 Solid (unrecoverable) Comparative Example 2-2 24.55 82.41 92 Comparative Example 2-3 23.42 85.74 96
  • Comparative Example 2-4 Solid (unrecoverable) Comparative Example 2-5 Solid (unrecoverable) Comparative Example 2-6 22.51 84.51 96
  • Comparative Example 2-7 Solid (unrecoverable) Comparative Example 2-8 17.38 92.79 97 Comparative Example 2-9 15.95 92.80 97
  • methyl ethyl ketone (MEK) as a dispersion solvent
  • zirconia powder having an average particle diameter of 10 nm 40% by weight of zirconia powder having an average particle diameter of 10 nm
  • 10% by weight of the polymer according to Example 1-1 was stirred for 30 minutes.
  • zirconia beads (average particle diameter: 0.05 mm) was added based on 100 parts by weight of the mixture so that the zirconia particles could be evenly dispersed, and then dispersed in a paint shaker for 3 hours to recover the dispersion did Based on 50 parts by weight of the prepared dispersion, 45 parts by weight of butyl acrylate as an acrylic monomer and 5 parts by weight of a dispersing agent were added, and the dispersion solvent was removed under reduced pressure to prepare a composition.
  • a composition was prepared in the same manner as in Example 3-1, except for adding 2-ethylhexyl acrylate as an acrylic monomer.
  • Example 3-1 the composition was prepared in the same manner as in Example 3-1, except that isobornyl acrylate was added as an acrylic monomer.
  • Example 3-1 the composition was prepared in the same manner as in Example 3-1, except for adding 4-acryloyl morpholine as an acrylic monomer.
  • Example 3-1 the composition was prepared in the same manner as in Example 3-1, except for adding methacryloxypropyltrimethoxysilane as a surface treatment agent.
  • Comparative Example 3-1 except for adding 2-ethylhexyl acrylate as an acrylic monomer, the rest of the composition was prepared in the same manner.
  • a composition was prepared in the same manner as in Comparative Example 3-1, except for adding isobornyl acrylate as an acrylic monomer.
  • a composition was prepared in the same manner as in Comparative Example 3-1, except for adding 4-acryloyl morpholine as an acrylic monomer.
  • Example 3-1 1.57 230 12.2
  • Example 3-2 1.57 180 11.8
  • Example 3-3 1.55 250 13.5
  • Example 3-4 1.56 195 12.5
  • Comparative Example 3-1 1.57 450 15.8 Comparative Example 3-2 1.57 480 16.2 Comparative Example 3-3 1.54 380 19.4 Comparative Example 3-4 1.55 320 16.5

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Manufacturing & Machinery (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Adhesive Tapes (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)

Abstract

La présente invention concerne une composition hybride organique/inorganique et un film adhésif la comprenant. Une composition selon un mode de réalisation de la présente invention comprend des particules inorganiques modifiées en surface avec un agent de traitement de surface, et un monomère acrylique, les particules inorganiques modifiées en surface et le monomère acrylique pouvant avoir un rapport en poids de 1:1 à 2:1.
PCT/KR2022/020668 2021-12-20 2022-12-19 Composition hybride organique/inorganique et film adhésif la comprenant Ceased WO2023121162A1 (fr)

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CN202280072039.7A CN118159575A (zh) 2021-12-20 2022-12-19 有机/无机复合组合物及包括其的胶粘薄膜
JP2024529663A JP7763343B2 (ja) 2021-12-20 2022-12-19 有機・無機ハイブリッド組成物及びこれを含む粘着フィルム

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KR1020210182913A KR20230093909A (ko) 2021-12-20 2021-12-20 유무기 하이브리드 조성물 및 이를 포함하는 점착 필름

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117402286A (zh) * 2023-12-14 2024-01-16 优美特（北京）环境材料科技股份公司 一种改性丙烯酸树脂及其制备方法、粉末涂料及应用

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20100013812A (ko) * 2008-08-01 2010-02-10 동우 화인켐 주식회사 광확산 점착제 조성물, 이를 이용한 편광판 및액정표시장치
KR20130058003A (ko) * 2010-04-20 2013-06-03 쓰리엠 이노베이티브 프로퍼티즈 컴파니 반응성 표면-개질된 나노입자를 함유하는 감압 접착제
KR101952463B1 (ko) * 2011-02-21 2019-02-26 아사히 가세이 케미칼즈 가부시키가이샤 유기 무기 복합체를 포함하는 코팅재, 유기 무기 복합막 및 반사 방지 부재
KR20210079845A (ko) * 2019-12-20 2021-06-30 주식회사 케이씨텍 유무기 하이브리드 점착제 조성물 및 점착 필름

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003119207A (ja) * 2001-10-11 2003-04-23 Jsr Corp 光硬化性組成物、その硬化物、及び積層体
JP2015078339A (ja) * 2013-09-10 2015-04-23 昭和電工株式会社 有機無機複合体の製造方法、硬化性組成物、硬化性組成物の製造方法、硬化性組成物の硬化物、ハードコート材、及びハードコート膜
EP3189107B1 (fr) * 2014-09-04 2018-11-28 3M Innovative Properties Company Revêtement dur et son procédé de réalisation
US11912860B2 (en) * 2018-03-29 2024-02-27 Corning Incorporated Highly loaded inorganic filled organic resin systems
JP7406485B2 (ja) * 2018-06-15 2023-12-27 ナガセケムテックス株式会社 無機酸化物微粒子分散液

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20100013812A (ko) * 2008-08-01 2010-02-10 동우 화인켐 주식회사 광확산 점착제 조성물, 이를 이용한 편광판 및액정표시장치
KR20130058003A (ko) * 2010-04-20 2013-06-03 쓰리엠 이노베이티브 프로퍼티즈 컴파니 반응성 표면-개질된 나노입자를 함유하는 감압 접착제
KR101952463B1 (ko) * 2011-02-21 2019-02-26 아사히 가세이 케미칼즈 가부시키가이샤 유기 무기 복합체를 포함하는 코팅재, 유기 무기 복합막 및 반사 방지 부재
KR20210079845A (ko) * 2019-12-20 2021-06-30 주식회사 케이씨텍 유무기 하이브리드 점착제 조성물 및 점착 필름

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
HABSUDA, J. SIMON, G.P. CHENG, Y.B. HEWITT, D.G. LEWIS, D.A. TOH, H.: "Organic-inorganic hybrids derived from 2-hydroxyethylmethacrylate and (3-methacryloyloxypropyl)trimethoxysilane", POLYMER, vol. 43, no. 15, 1 July 2002 (2002-07-01), AMSTERDAM, NL, pages 4123 - 4136, XP004354960, ISSN: 0032-3861 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117402286A (zh) * 2023-12-14 2024-01-16 优美特（北京）环境材料科技股份公司 一种改性丙烯酸树脂及其制备方法、粉末涂料及应用
CN117402286B (zh) * 2023-12-14 2024-03-12 优美特（北京）环境材料科技股份公司 一种改性丙烯酸树脂及其制备方法、粉末涂料及应用

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TWI848474B (zh) 2024-07-11
JP7763343B2 (ja) 2025-10-31

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