WO2013183532A1 - Composition de résine pour le revêtement de matériaux - Google Patents

Composition de résine pour le revêtement de matériaux Download PDF

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WO2013183532A1
WO2013183532A1 PCT/JP2013/065007 JP2013065007W WO2013183532A1 WO 2013183532 A1 WO2013183532 A1 WO 2013183532A1 JP 2013065007 W JP2013065007 W JP 2013065007W WO 2013183532 A1 WO2013183532 A1 WO 2013183532A1
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group
resin composition
meth
component
atom
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PCT/JP2013/065007
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English (en)
Japanese (ja)
Inventor
慶次 後藤
貴子 星野
公彦 依田
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電気化学工業株式会社
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Priority to JP2014519956A priority Critical patent/JP6105574B2/ja
Priority to KR1020147033269A priority patent/KR102135467B1/ko
Priority to CN201380029992.4A priority patent/CN104350111B/zh
Publication of WO2013183532A1 publication Critical patent/WO2013183532A1/fr

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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
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • 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
    • C08F20/00—Homopolymers and 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
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/38—Esters containing sulfur
    • 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
    • C08F220/1807—C7-(meth)acrylate, e.g. heptyl (meth)acrylate or benzyl (meth)acrylate
    • 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
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
    • C08F220/301—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and one oxygen in the alcohol moiety
    • 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
    • C08F220/38—Esters containing sulfur
    • 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
    • C08F228/00—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 a bond to sulfur or by a heterocyclic ring containing sulfur
    • C08F228/06—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 a bond to sulfur or by a heterocyclic ring containing sulfur by a heterocyclic ring containing sulfur
    • 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
    • C08F28/00—Homopolymers and 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 a bond to sulfur or by a heterocyclic ring containing sulfur
    • C08F28/06—Homopolymers and 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 a bond to sulfur or by a heterocyclic ring containing sulfur by a heterocyclic ring containing sulfur

Definitions

  • the present invention relates to a resin composition for a coating material used for various sensor elements, display elements and the like, and further to a high refractive index resin composition used for a high refractive index layer of an antireflection film or an optical waveguide film.
  • a coating layer made of an inorganic substance or an organic substance is provided for the purpose of protecting the surface. Furthermore, in recent years, a covering layer in which high refractive index layers and low refractive index layers are alternately stacked is used for the purpose of imparting functions such as antireflection and optical waveguide to the surface protective layer.
  • This high refractive index layer contains a high refractive index inorganic film formed by vapor deposition of ceramics such as titania, zirconia and alumina, and radical polymerizable monomers such as bisphenol A type epoxy (meth) acrylate and urethane (meth) acrylate.
  • the high-refractive-index organic film that is cured by irradiating energy rays such as ultraviolet rays after coating is used according to the purpose, but the former inorganic film is in close contact when the substrate is a film or sheet.
  • photocurable high-refractive-index organic films blended with radically polymerizable monomers have been widely used. It is like that.
  • Patent Documents 1 to 3 disclose a resin composition using sulfur-containing (meth) acrylate. Also known are photocurable resin compositions. Further, for example, Patent Document 4 discloses an active energy ray-curable composition using urethane (meth) acrylate having a diphenyl sulfone structure.
  • 4,4′-dimercaptodiphenyl sulfide dimethacrylate is a bisphenol A type. Although it has a higher refractive index than a compound having an aromatic ring such as epoxy (meth) acrylate, these compounds generally absorb light with a wavelength of 450 nm or less, so they are colored yellow and the transparency tends to decrease. There was a problem that it was difficult to adhere to.
  • Patent Document 5 discloses a compound and a polymer having a dinaphthothiophene skeleton.
  • a photocured film prepared by diluting a photopolymerizable composition using dinaphthothiophene having an ethylenically unsaturated double bond with a solvent such as ethyl acetate is disclosed. (Paragraph number [0143]).
  • the residual solvent due to the influence of the residual solvent, it may cause a decrease in strength and outgassing, and good reliability cannot be obtained, or crystalline components tend to precipitate in the composition when stored for a long time. , The refractive index fluctuates and the coating cannot be performed.
  • the present invention has been made in view of such circumstances, and provides a resin composition for a coating material that has a high refractive index and high transparency and does not require the use of a solvent.
  • a dinaphthothiophene compound having one or more polymerizable functional groups having an ethylenically unsaturated double bond represented by the following general formula (1):
  • each X is independently a single bond, a divalent organic group or a divalent atom
  • each R 1 is independently a hydrogen atom or a methyl group
  • c + d is C is an integer of 0 to 4
  • d is an integer of 0 to 4.
  • X is a divalent organic group, X is an oxygen atom;
  • the dinaphthothiophene compound as shown in the general formula (1) does not use a solvent.
  • a precipitate that does not easily dissolve is generated after standing for a while, as a resin composition for a coating material. It was found that it was difficult to use (Comparative Example 2). Accordingly, further investigations have been made to solve such problems.
  • a monofunctional (meth) acrylate containing one or more aromatic rings is used in place of the polyfunctional epoxy acrylate, this is the case.
  • the component (B) is a monofunctional (meth) acrylate containing one aromatic ring.
  • the component (B) includes one or more selected from benzyl (meth) acrylate and phenoxyethyl (meth) acrylate.
  • the polymerizable functional group is a (meth) acryloyl group or an allyl ether group.
  • the component (A) is 6- (meth) acryloylmethyldinaphthothiophene, 6- (meth) acryloylethyldinaphthothiophene, 2,12-diallyl ether dinaphthothiophene, and 3,11-diallyl ether diene. Including one or more selected from naphthothiophene.
  • the content ratio of the component (C) is 0.2 to 10 parts by mass with respect to the total amount of the composition.
  • a covering material comprising the above-described resin composition for a covering material, and a base material (eg, glass, film or sheet) on which the covering material is formed.
  • a base material eg, glass, film or sheet
  • a layer having a refractive index lower than that of the above-mentioned resin composition for a coating material is formed after a layer made of the above-described resin composition for a coating material is formed on a substrate.
  • the resin composition of the present invention comprises a resin composition for a coating material containing a dinaphthothiophene compound having a polymerizable functional group, a monofunctional (meth) acrylate having an aromatic ring, and a radical polymerization initiator in a specific ratio. Therefore, it has characteristics such as high refractive index and transparency required for surface protection of sensor elements, display elements, antireflection films, optical waveguide films, and the like, and excellent adhesion. Moreover, since the resin composition for coating
  • a coating material is a coating on a substrate such as a glass substrate, a plastic film, or a plastic sheet for the purpose of imparting surface protection, designability, and functionality such as antireflection or optical waveguide. Means the material to be.
  • the energy beam curable resin composition according to the present embodiment has a difunctional dimer having one or more polymerizable functional groups having an ethylenically unsaturated double bond represented by the following general formula (1) as the component (A). It has a naphthothiophene compound.
  • each X is independently a single bond, a divalent organic group or a divalent atom
  • each R 1 is independently a hydrogen atom or a methyl group
  • c + d is C is an integer of 0 to 4
  • d is an integer of 0 to 4.
  • X is a divalent organic group, X is an oxygen atom;
  • a tin atom that may have a bond with other atoms A phosphorus atom that may have a bond, wherein X may be bonded to any of the substitutable carbon atoms in the naphthalene ring to which they are bonded, wherein (R) a or (R) b is means a or b identical or different substituents, which may be attached to any of the substitutable carbon atoms in the naphthalene ring to which they are attached, and each R is independently an organic A group, a hydroxyl group, an amino group, a nitro group, a thiol group, a sulfo group, a halogen atom, or an optionally substituted silyl group, a is an integer of 0 to 5, and b is an integer of 0 to 5 (It is an integer.)
  • Examples of the polymerizable functional group include a vinyl group, a styryl group, a vinyl ether group, an allyl group, an allyl ether group, a (meth) acryloyl group, a (meth) acrylonitrile group, etc., but transparency and adhesion to a substrate.
  • a (meth) acryloyl group or an allyl ether group is preferable, and a (meth) acryloyl group is particularly preferable.
  • dinaphthothiophene compound examples include 6-vinyldinaphthothiophene, 6- (meth) acryloyloxymethyldinaphthothiophene, 6- (meth) acryloyloxyethyl dinaphthothiophene, 6-vinyl ether dinaphthothiophene, 6-allyldinaphthothiophene, 6-allyloxydinaphthothiophene, 2,12-divinyldinaphthothiophene, 3,11-divinyldinaphthothiophene, 5,9-divinyldinaphthothiophene, 2,12-di (meth) Acryloyloxymethyldinaphthothiophene, 3,11-di (meth) acryloyloxymethyldinaphthothiophene, 2,12-diallyloxymethyldinaphthothiophene, 3,11
  • 6- (meth) acryloyloxymethyldinaphthothiophene 6- (meth) acryloyloxyethyl dinaphthothiophene, 2,12 -Diallyloxydinaphthothiophene and 3,11-diallyloxydinaphthothiophene are preferred, and 6- (meth) acryloyloxymethyldinaphthothiophene is particularly preferred.
  • the content ratio of the component (A) is preferably 15 to 60 parts by mass with respect to the total amount of the resin composition.
  • 15 to 50 parts by mass is more preferable, 17 to 50 parts by mass is further preferable, and 20 to 40 parts by mass is most preferable.
  • the total amount of the resin composition is preferably 100 parts by mass in total of the component (A) and the component (B).
  • the dinaphthothiophene-based compound can be produced by a production method exemplified in Japanese Patent Application Laid-Open No. 2011-178985 (Patent Document 5) and Japanese Patent Application Laid-Open No. 2012-136576 (Patent Document 6).
  • a product manufactured by any manufacturing method is not limited.
  • the resin composition of the present invention contains a monofunctional (meth) acrylate having one or more aromatic rings as the component (B).
  • the number of aromatic rings is, for example, 1, 2, 3, and preferably one.
  • the monofunctional (meth) acrylate examples include benzyl (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, phenoxytetraethylene glycol (meth) acrylate, and phenoxyhexaethylene glycol (meth) acrylate.
  • Nonylphenyl (meth) acrylate, ethylene oxide modified nonylphenyl (meth) acrylate, phthalic acid modified (meth) acrylate, naphthyl (meth) acrylate, bisphenylfluorene (meth) acrylate, 2- (o-phenylphenoxy) ethyl ( (Meth) acrylate and the like can be exemplified, but from the viewpoint of compatibility with the component (A), refractive index, and transparency, benzyl (meth) acrylate and / or phenoxyethyl (meth) ) Acrylate is particularly preferred.
  • the content ratio of the component (B) is preferably 40 to 85 parts by mass with respect to the total amount of the resin composition, particularly the refractive index, transparency, adhesion to the substrate, and compatibility with the component (A).
  • 50 to 85 parts by mass is more preferable, 50 to 83 parts by mass is further preferable, and 60 to 80 parts by mass is most preferable.
  • the resin composition of the present invention may contain a monofunctional (meth) acrylate compound having no aromatic ring or a polyfunctional (meth) acrylate as long as the effects of the invention are not impaired.
  • the resin composition of the present embodiment contains (C) a radical photopolymerization initiator.
  • the radical photopolymerization initiator is not particularly limited as long as it is a compound that generates radicals when irradiated with energy rays.
  • photo radical polymerization initiator examples include benzyl derivatives such as benzyl, benzoin, benzoin benzoic acid, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether, benzophenone derivatives such as benzophenone and 4-phenylbenzophenone, and 2,2-diethoxy Alkyl acetophenone derivatives such as acetophenone, benzyldimethyl ketal, 1-hydroxycyclohexyl phenyl ketone, 1- (4-isopropylphenyl) 2-hydroxy-2-methylpropan-1-one, 1- (4- (2-hydroxyethoxy) -Phenyl) -2-hydroxy-2-methyl-1-propan-1-one, ⁇ -hydroxyacetophenone derivatives such as 2-hydroxy-2-methyl-1-phenylpropan-1-one Bisdiethylaminobenzophenone, 2-methyl-1- (4- (methylthio) phenyl) -2
  • the content of component (C) is preferably 0.1 to 10 parts by weight, more preferably 0.5 to 5 parts by weight, based on the total amount of the resin composition. If it is in the range of 0.1 to 10 parts by mass, the curability will not be deteriorated and the transparency will not be lowered.
  • an antioxidant such as an acrylic rubber and a urethane rubber, a photosensitizer, a light stabilizer, a solvent, an extender, a filler, a reinforcing material
  • additives such as a plasticizer, a thickener, a dye, a pigment, a flame retardant, and surfactant.
  • the method for producing the resin composition according to this embodiment is not particularly limited as long as the above materials can be sufficiently mixed.
  • the mixing method of the material is not particularly limited, and examples thereof include a stirring method using a stirring force accompanying rotation of a propeller, a method using a normal disperser such as a planetary stirrer by rotation and revolution, and the like. These mixing methods are preferable because stable mixing can be performed at low cost.
  • the resin composition can be cured by irradiation with energy rays using the following light source.
  • the light source used for curing the resin composition is not particularly limited, but is a halogen lamp, a metal halide lamp, a high-power metal halide lamp (containing indium or the like), a low-pressure mercury lamp, a high-pressure mercury lamp, or an ultra-high pressure.
  • LED light emitting diode
  • the above light sources have different emission wavelengths and energy distributions. Therefore, the light source is appropriately selected depending on the reaction wavelength of the photopolymerization initiator. Natural light (sunlight) can also be a reaction initiation light source.
  • the light source may perform direct irradiation, focused irradiation with a reflecting mirror or the like, or focused irradiation with a fiber or the like.
  • a low wavelength cut filter, a heat ray cut filter, a cold mirror, or the like can also be used.
  • the resin composition having the above-mentioned structure is quickly cured by irradiation with energy rays, a cured product excellent in optical properties such as high transparency and high refractive index can be provided.
  • the resin composition having the above structure is excellent in optical properties such as high transparency and high refractive index, and has excellent adhesion to substrates such as glass, plastic film, and plastic sheet. Can be offered as.
  • the resin composition having the above structure is excellent in optical properties such as high transparency and high refractive index, it can be used as a high refractive index layer of an antireflection film or an optical waveguide film.
  • An optical waveguide film can be provided.
  • the antireflection film and optical waveguide film are coated with a layer made of the resin composition of the present invention (hereinafter referred to as a high refractive index layer) on various substrates such as glass, plastic film, plastic sheet, etc., and irradiated with energy rays. Then, a layer having a lower refractive index than the high refractive index layer (hereinafter referred to as a low refractive index layer) is formed on the high refractive index layer.
  • a layer made of the resin composition of the present invention hereinafter referred to as a high refractive index layer
  • a low refractive index layer a layer having a lower refractive index than the high refractive index layer
  • Base materials include glass base materials such as alkali-free glass, alkali glass, borosilicate glass, and quartz, ceramic base materials such as silica, alumina, and silicon nitride, and metals such as silicone, aluminum, stainless steel, iron, copper, and silver. From resins such as base materials, acrylic resins, styrene resins, carbonate resins, olefin resins, polyester resins, polyimide resins, polyamide resins, epoxy resins, silicone resins, fluorine resins, and cellulose resins A film base material, a sheet base material, and the like can be used.
  • the low refractive index layer examples include inorganic films such as alkali metal fluorides such as magnesium fluoride and potassium fluoride, silica, and the like, and organic films such as fluoropolymers such as polyperfluoroethylene and perfluorocycloolefin.
  • organic films such as fluoropolymers such as polyperfluoroethylene and perfluorocycloolefin.
  • Polyether resins such as polyethylene glycol, silicone resins, acrylic resins, epoxy resins, urethane resins and their fluorine-modified resins can be used.
  • the resin composition having the above structure is excellent in optical properties such as high transparency and high refractive index, and therefore has a high liquid crystal panel, an organic electroluminescence panel, a touch panel, a projector, a smartphone, a mobile phone, a digital camera, a digital movie display element, It can be used as a coating material used for various sensor parts such as CCD, CMOS, and biochip, semiconductor elements such as flash memory, DRAM, and semiconductor laser, and also as a high refractive index layer of an antireflection film or an optical waveguide film.
  • DNTMA 6-Methacryloyloxymethyldinaphthothiophene
  • VDNT 6-vinyldinaphthothiophene
  • EDNTMA 6-methacryloyloxyethyldinaphthothioph
  • B Monofunctional (meth) acrylate having an aromatic ring (B-1) benzyl methacrylate (“Light Ester BZ” manufactured by Kyoeisha Chemical Co., Ltd.) (B-2) Benzyl acrylate (Osaka Organic Chemical Co., Ltd. “Biscoat # 160”) (B-3) Phenoxyethyl methacrylate (Kyoeisha Chemical Co., Ltd.
  • Light Ester PO Phenoxyethyl acrylate (“Light acrylate PO-A” manufactured by Kyoeisha Chemical Co., Ltd.) (B-5) 2- (o-phenylphenoxy) ethyl acrylate (“NK Ester A-LEN-10” manufactured by Shin-Nakamura Chemical Co., Ltd.)
  • C Photoradical polymerization initiator (C-1) Benzyldimethyl ketal (“IRGACURE 651” manufactured by BASF) (C-2) 1-hydroxy-cyclohexyl phenyl ketone (“Irgacure 184” manufactured by BASF) (C-3) Bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide (“Irgacure 819” manufactured by BASF)
  • Examples 1 to 18, Comparative Examples 1 to 6 The raw materials of the types shown in Tables 1 to 3 were mixed in the composition ratios (units are parts by mass) shown in Tables 1 to 3, to prepare resin compositions for coating materials, and the evaluation described below was performed. No solvent was used. Various evaluation results are shown in Tables 1 to 3. Unless otherwise specified, the test was carried out in an environment of 23 ° C. and 50% humidity.
  • a cured product test piece cured under conditions of an irradiation intensity of a wavelength of 30 mW / cm 2 and an integrated light amount of 30,000 mJ / cm 2 was prepared, and a refractive index was evaluated.
  • the refractive index was evaluated by measuring the refractive index at a wavelength of 633 nm using a spectroscopic prism coupler refractive index measuring device ("MODEL 2010 PRISM COUPLER" manufactured by Metricon).
  • the resin composition was applied on a heat-resistant glass (trade name “heat-resistant Pyrex (registered trademark) glass”, 25 mm ⁇ 25 mm ⁇ 2.0 mm) with a film thickness of 30 ⁇ m, and then an ultra-high pressure mercury lamp mounting device (“UL-” manufactured by HOYA). 750 "), a test piece cured under the conditions of an irradiation intensity of a wavelength of 365 nm of 50 mW / cm 2 and an integrated light quantity of 30,000 mJ / cm 2 was prepared, and an ultraviolet-visible spectrophotometer (Shimadzu Corporation" UV “ -2550 "), and the transmittance was measured at 450 nm using a heat resistant glass as a reference.
  • a heat-resistant glass trade name “heat-resistant Pyrex (registered trademark) glass”, 25 mm ⁇ 25 mm ⁇ 2.0 mm
  • UL- ultra-high pressure mercury lamp mounting device
  • a cut line was placed in the cured film so as to be 2 mm long ⁇ 2 mm wide ⁇ 25 squares in an environment of a temperature of 23 ° C. and a relative humidity of 50%, and then cellophane.
  • a tape (model CT-405AP manufactured by Nichiban Co., Ltd .: width 24 mm, adhesive strength 23 N / 10 mm) was applied and 180 ° peeling was performed. The number of cells remaining after 180 ° peeling was counted and evaluated according to the following criteria. Other conditions that were not specified were in accordance with JIS K 5600-5-6. ⁇ : All 25 sheets remained ⁇ : 15 or more and 24 or less remained x: Less than 14 sheets
  • Example 1 In Examples 1 to 18, excellent results were obtained in terms of liquid stability, refractive index, spectral transmittance, and adhesion. However, in Example 1, since the blending ratio of the dinaphthothiophene compound was small, the refractive index was slightly low. In Example 6, since the compounding ratio of the dinaphthothiophene compound was large, the liquid stability and adhesion were slightly deteriorated. In Example 10 using a dinaphthothiophene compound having a vinyl group, Examples 1 to 9 and Examples 11 to 14 using a dinaphthothiophene compound having a (meth) acryloyl group or an allyl ether group were used.
  • Example 3 In comparison, liquid stability, spectral transmittance and adhesion were not preferred. This result shows the advantage of using a dinaphthothiophene compound having a (meth) acryloyl group or an allyl ether group. Further, comparing Example 3 with Examples 11 to 13, it was found that when DNTMA was used as in Example 3, the refractive index and spectral transmittance were particularly high. Furthermore, as in Example 14, when an acrylate having two aromatic rings was used as the component (B), the liquid stability, spectral transmittance, and adhesion were deteriorated.
  • Comparative Example 1 since the dinaphthothiophene compound was not used, the refractive index was not sufficient. In Comparative Example 2, since polyfunctional acrylate (bisphenol A type epoxy acrylate) was used, the liquid stability was very poor, and a test piece for evaluation of refractive index and spectral transmittance could not be prepared. In Comparative Example 3, since a compound (styrene) having an aromatic ring but not (meth) acrylate was used instead of the component (B), curing did not occur sufficiently even when light irradiation was performed.
  • Comparative Example 4 since monofunctional (meth) acrylate (methyl methacrylate) having no aromatic ring was used instead of component (B), the liquid stability was poor and precipitates that did not dissolve easily were generated. It was. In Comparative Example 5, since a dinaphthothiophene compound (dinaphthothiophene) having no functional group was used, the liquid stability was poor and precipitates that were not easily dissolved were generated. In Comparative Example 6, since there was too little (B) component, the liquid stability was bad and the precipitate which does not melt
  • the resin composition of the present invention is excellent in optical properties such as high transparency and high refractive index, a high liquid crystal panel, organic electroluminescence panel, touch panel, projector, smartphone, mobile phone, digital camera, digital movie display element, Suitable for use as sensor elements for various sensor components such as CCD, CMOS, biochip, coating materials used for semiconductor elements such as flash memory, DRAM, and semiconductor laser, and as a high refractive index layer for antireflection films and optical waveguide films. Can be very useful in industry.

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  • Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)

Abstract

La présente invention concerne une composition de résine pour le revêtement de matériaux, laquelle possède un indice de réfraction et une transparence élevés sans qu'il soit nécessaire d'utiliser un solvant. La présente invention concerne (1) une composition de résine pour le revêtement de matériaux, laquelle est caractérisée en ce qu'elle contient un composé dinaphtothiophène spécifique qui comporte un ou plusieurs groupes fonctionnels polymérisables possédant une double liaison éthyléniquement insaturée (constituant (A)), un (méth)acrylate monofonctionnel qui contient un ou plusieurs cycles aromatiques (constituant (B)), et un initiateur de photopolymérisation radicalaire (constituant (C)), et qui est aussi caractérisé en ce que le rapport de teneur du constituant (A) est dans la plage allant de 15 à 60 parties en masse et le rapport de teneur du constituant (B) est dans la plage allant de 40 à 85 parties en masse.
PCT/JP2013/065007 2012-06-06 2013-05-30 Composition de résine pour le revêtement de matériaux WO2013183532A1 (fr)

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JP2014519956A JP6105574B2 (ja) 2012-06-06 2013-05-30 被覆材用樹脂組成物
KR1020147033269A KR102135467B1 (ko) 2012-06-06 2013-05-30 피복재용 수지 조성물
CN201380029992.4A CN104350111B (zh) 2012-06-06 2013-05-30 被覆材料用树脂组合物

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WO2015029996A1 (fr) * 2013-08-30 2015-03-05 電気化学工業株式会社 Composition de résine de matière de revêtement
JP2015048368A (ja) * 2013-08-30 2015-03-16 電気化学工業株式会社 光学部品用高屈折率接着剤組成物
JP2017177681A (ja) * 2016-03-31 2017-10-05 三菱ケミカル株式会社 積層フィルム
JP2018083774A (ja) * 2016-11-22 2018-05-31 スガイ化学工業株式会社 ジナフトチオフェン誘導体及びその製造方法
WO2019167947A1 (fr) * 2018-02-27 2019-09-06 ソニー株式会社 Composé, polymère et matériau organique
WO2023068239A1 (fr) * 2021-10-19 2023-04-27 積水化学工業株式会社 Composition de résine pour utilisation d'étanchéité

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WO2015029996A1 (fr) * 2013-08-30 2015-03-05 電気化学工業株式会社 Composition de résine de matière de revêtement
JP2015048368A (ja) * 2013-08-30 2015-03-16 電気化学工業株式会社 光学部品用高屈折率接着剤組成物
JP2017177681A (ja) * 2016-03-31 2017-10-05 三菱ケミカル株式会社 積層フィルム
JP2018083774A (ja) * 2016-11-22 2018-05-31 スガイ化学工業株式会社 ジナフトチオフェン誘導体及びその製造方法
WO2019167947A1 (fr) * 2018-02-27 2019-09-06 ソニー株式会社 Composé, polymère et matériau organique
JPWO2019167947A1 (ja) * 2018-02-27 2021-03-04 ソニー株式会社 化合物、ポリマー及び有機材料
WO2023068239A1 (fr) * 2021-10-19 2023-04-27 積水化学工業株式会社 Composition de résine pour utilisation d'étanchéité

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TW201404787A (zh) 2014-02-01
CN104350111A (zh) 2015-02-11
JPWO2013183532A1 (ja) 2016-01-28
KR102135467B1 (ko) 2020-07-17
JP6105574B2 (ja) 2017-03-29
KR20150024319A (ko) 2015-03-06
CN104350111B (zh) 2017-10-10
TWI574978B (zh) 2017-03-21

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