WO2019189235A1 - Composition de résine pour couche intermédiaire de verre feuilleté, couche intermédiaire de verre feuilleté, matériau de film pour couche intermédiaire de verre feuilleté, verre feuilleté et procédé de fabrication de verre feuilleté - Google Patents

Composition de résine pour couche intermédiaire de verre feuilleté, couche intermédiaire de verre feuilleté, matériau de film pour couche intermédiaire de verre feuilleté, verre feuilleté et procédé de fabrication de verre feuilleté Download PDF

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Publication number
WO2019189235A1
WO2019189235A1 PCT/JP2019/012960 JP2019012960W WO2019189235A1 WO 2019189235 A1 WO2019189235 A1 WO 2019189235A1 JP 2019012960 W JP2019012960 W JP 2019012960W WO 2019189235 A1 WO2019189235 A1 WO 2019189235A1
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WO
WIPO (PCT)
Prior art keywords
laminated glass
film
interlayer
resin
meth
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PCT/JP2019/012960
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English (en)
Japanese (ja)
Inventor
広喜 葛岡
吉田　明弘
石川　栄作
直己 高原
遼 ▲高▼橋
圭一郎 西村
裕紀子 井上
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日立化成株式会社
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Publication of WO2019189235A1 publication Critical patent/WO2019189235A1/fr

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    • 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
    • B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/32—Epoxy compounds containing three or more epoxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/44—Amides
    • C08G59/46—Amides together with other curing agents
    • C08G59/48—Amides together with other curing agents with polycarboxylic acids, or with anhydrides, halides or low-molecular-weight esters thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50—Amines
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B60—VEHICLES IN GENERAL
    • B60J—WINDOWS, WINDSCREENS, NON-FIXED ROOFS, DOORS, OR SIMILAR DEVICES FOR VEHICLES; REMOVABLE EXTERNAL PROTECTIVE COVERINGS SPECIALLY ADAPTED FOR VEHICLES
    • B60J1/00—Windows; Windscreens; Accessories therefor
    • 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
    • C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
    • C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate

Definitions

  • the present invention relates to a resin composition for an interlayer film of laminated glass, an interlayer film for laminated glass, a film material for an interlayer film of laminated glass, a laminated glass, and a method for producing the laminated glass.
  • Laminated glass generally has an intermediate film sandwiched between two glass plates.
  • the interlayer film for laminated glass for example, a resin layer containing polyvinyl acetal resin, ionomer resin, acrylic resin, or the like is used (for example, Patent Documents 1 to 5).
  • optically transparent laminated glass is used in transportation equipment such as vehicles and airplanes.
  • chipping resistance of the laminated glass can be improved by increasing the glass used, but the weight of the laminated glass increases.
  • the chipping resistance of laminated glass can also be improved by using high-strength glass such as tempered glass, but tempered glass spreads small pieces of scratches on the entire glass surface when broken, The driver's visibility is reduced.
  • An object of one aspect of the present invention is to provide a resin composition for an interlayer film of laminated glass, which can provide a laminated glass having high chipping resistance.
  • One aspect of the present invention is a resin composition used for forming an interlayer film for laminated glass provided between two opposing glass plates, wherein the resin composition has (A) an epoxy group ( A resin composition for an interlayer film of laminated glass comprising a (meth) acrylic copolymer and (B) a curing agent is provided.
  • a resin composition for an interlayer film of laminated glass which can provide a laminated glass having high chipping resistance.
  • laminated glass excellent in optical transparency can be provided.
  • an interlayer film for laminated glass having excellent processability and bonding properties can be provided.
  • a hard resin such as polycarbonate or polymethylmethacrylate
  • Utilization as an interlayer film for laminated glass is difficult due to the low conformability and the high heat distortion temperature, and thus the laminated property of laminated glass is low. That is, in the materials used for the conventional glass material and the laminated glass material, it can be said that the followability to the curved glass, the bonding property, and the chipping resistance are in a trade-off relationship.
  • laminated glass for automobiles has been increased in area and curved surface, and is required to have good bonding properties in an interlayer film and easy handling in production.
  • (meth) acrylate means “acrylate” or “methacrylate” corresponding thereto.
  • (meth) acryl means “acryl” or “methacryl” corresponding thereto, and “(meth) acryloyl” means “acryloyl” or “methacryloyl” corresponding thereto.
  • the content of each component in the composition means the total amount of the plurality of substances present in the composition unless there is a specific notice when there are a plurality of substances corresponding to each component in the composition.
  • the “resin composition for forming an interlayer film of a laminated glass” may be referred to as “resin composition for forming an interlayer film”, and the “interlayer film for laminated glass” may be referred to as an “interlayer film”.
  • FIG. 1 is a cross-sectional view showing an embodiment of a laminated glass.
  • a laminated glass 1 shown in FIG. 1 includes two opposing glass plates 21 and 22 and an intermediate film 3 disposed between the glass plates 21 and 22.
  • the glass plates 21 and 22 may be inorganic glass, and examples of the inorganic glass include float glass, air-cooled tempered glass, chemically tempered glass, and multilayer glass.
  • the intermediate film 3 includes (A) a (meth) acrylic copolymer having an epoxy group (hereinafter sometimes referred to as (A) component) and (B) a curing agent (hereinafter sometimes referred to as (B) component). And a resin composition for an interlayer film of laminated glass.
  • the laminated glass and the interlayer film for laminated glass are not limited to the embodiment shown in FIG. 1 and can be changed without departing from the gist of the present invention.
  • the resin layer formed from the resin composition for interlayer film of laminated glass containing the component (A) and the component (B) may be used as a single layer, or two or more layers may be laminated and used. May be. That is, the interlayer film for laminated glass may have one resin layer containing the above-described resin composition for interlayer films or a cured product thereof, and may have two or more resin layers, and these resin layers It may be laminated. A resin layer formed from other resin species such as polyvinyl acetal resin and ionomer resin may be further laminated. From the viewpoint of superior chipping resistance, the interlayer film for laminated glass is preferably a resin layer formed from the above-described resin composition for interlayer films.
  • FIG. 3 is a cross-sectional view showing another embodiment of a laminated glass.
  • a laminated glass 100 shown in FIG. 3 includes two glass plates 210 and 220 facing each other and an intermediate film 300 disposed between the glass plates 210 and 220.
  • the intermediate film 300 is a resin laminate including a first resin layer 310 and a second resin layer 320.
  • the first resin layer 310 is a resin layer containing the above-described resin composition for an intermediate film or a cured product thereof
  • the second resin layer 320 is a resin layer containing a polyvinyl acetal resin.
  • the laminated glass 100 tends to be excellent in chipping resistance and penetration resistance by including the intermediate film 300 containing the first resin layer 310 and the second resin layer 320.
  • the laminated glass 100 may be a vehicle window member.
  • the laminated glass 100 is a vehicle window member, and one of the two glass plates 210 and 220 is an outer glass plate directed to the outside of the vehicle when the laminated glass 100 is mounted on the vehicle, From the viewpoint of better chipping resistance and penetration resistance, the first resin layer 310 of the intermediate film 300 is preferably adjacent to the outer glass plate. That is, when the laminated glass 100 is a vehicle window member, laminated glass laminated in the order of the first resin layer and the second resin layer from the outer glass plate side is preferable.
  • the intermediate film 300 may contain two or more first resin layers or may contain two or more second resin layers. When the intermediate film 300 contains two or more first resin layers or two or more second resin layers, the first resin layers and the second resin layers may be alternately laminated.
  • the thickness of the first resin layer is not particularly limited, but may be 10 to 300 ⁇ m, 50 to 250 ⁇ m, or 100 to 200 ⁇ m.
  • the thickness of the second resin layer is not particularly limited, but may be 300 to 800 ⁇ m, 350 to 750 ⁇ m, or 400 to 600 ⁇ m.
  • the polyvinyl acetal resin contained in the second resin layer is not particularly limited, and a polyvinyl acetal resin usually used in the technical field can be used.
  • examples of the polyvinyl acetal resin include polyvinyl butyral and polyvinyl formal.
  • the degree of acetalization of the polyvinyl acetal resin may be 5 to 90 mol%, 25 to 80 mol%, or 50 to 70 mol%.
  • the second resin layer may further contain a plasticizer.
  • a plasticizer is not specifically limited, The plasticizer normally used in the said technical field can be used. From the viewpoint of better penetration resistance, the plasticizer is selected from the group consisting of triethylene glycol di-2-ethylbutyrate, triethylene glycol di-2-ethylhexanoate, and triethylene glycol di-n-heptanoate. It is preferable to include at least one, and it is more preferable to include triethylene glycol di-2-ethylhexanoate.
  • the content of the plasticizer is 10 to 70 parts by weight, 20 to 60 parts by weight, 30 to 50 parts by weight, or 35 to 35 parts by weight with respect to 100 parts by weight of the polyvinyl acetal resin in the second resin layer, from the viewpoint of superior penetration resistance. It may be 45 parts by mass.
  • the resin composition for an interlayer film of laminated glass according to this embodiment is used as an organic electroluminescence (organic EL), an image display member used in an image display device such as a liquid crystal display, and a protective material for the image display member. Is possible.
  • a component should just contain the monomer unit derived from the (meth) acryl monomer which has an epoxy group. 70 mass% or more, 75 mass% or more, or 80 mass% or more may be sufficient as content of (A) component on the basis of the total mass of the resin composition for interlayer films.
  • component (A) for example, a monomer unit derived from a (meth) acrylic monomer having an epoxy group, a monomer unit derived from a (meth) acrylic monomer having no epoxy group, and as necessary And a copolymer containing a monomer unit derived from a compound having an ethylenically unsaturated group other than (meth) acrylic monomer.
  • Examples of the (meth) acrylic monomer having an epoxy group include glycidyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate glycidyl ether, 3,4-epoxycyclohexylmethyl (meth) acrylate, and the like.
  • glycidyl (meth) acrylate from the viewpoint of heat resistance and chipping resistance.
  • the monomer unit derived from the (meth) acrylic monomer having an epoxy group includes a monomer unit derived from glycidyl (meth) acrylate.
  • Content of monomer unit derived from (meth) acrylic monomer having epoxy group in component (A) ((meth) acrylic monomer having epoxy group based on the total amount of copolymerization component for synthesizing component (A)) Is preferably 5 to 50% by mass, more preferably 10 to 40% by mass, and still more preferably 15 to 35% by mass based on the mass of the component (A). If the content of the monomer unit derived from the (meth) acrylic monomer having an epoxy group is 5% by mass or more, the chipping resistance of the laminated glass can be improved, and if it is 50% by mass or less. In addition, since the reaction between epoxy groups can be suppressed during storage of the resin composition for an interlayer film, there is a tendency that sufficient storage stability can be obtained.
  • (meth) acrylic monomers having no epoxy group examples include methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, lauryl (meth) acrylate, stearyl ( Aliphatic (meth) acrylates such as meth) acrylate, behenyl (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, methoxypolypropylene glycol (meth) acrylate; cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) Cycloaliphatic (meth) acrylates such as acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate; benzyl (meth) acrylate, phenoxy Ethyl (meth) aromatic
  • acrylate isobornyl (meth) acrylate, adamantyl (meth) acrylate, dicyclopentanyl (meth) acrylate, benzyl (meth) acrylate, or 2-tetrahydrofurfuryl (meth) acrylate.
  • the blending amount of (meth) acrylic monomer is preferably 50 to 95% by mass, more preferably 60 to 90% by mass, and still more preferably 65 to 85% by mass based on the mass of component (A).
  • the content of the monomer unit derived from the aliphatic (meth) acrylate in the component (A) is preferably 10 to 50% by mass, more preferably 15 to 45% by mass based on the mass of the component (A). More preferably, it is 20 to 40% by mass.
  • the content of monomer units derived from the alicyclic (meth) acrylate in the component (A) is preferably 30 to 80% by mass, and 35 to 70% by mass based on the mass of the component (A) More preferred is 40 to 65% by mass.
  • Examples of compounds having an ethylenically unsaturated group other than (meth) acrylic monomers include styrene, (meth) acrylonitrile, N-cyclohexylmaleimide, N-phenylmaleimide, vinylcyclohexyl ether, vinylphenyl ether, vinyl acetate, N- Examples thereof include vinyl pyrrolidone, vinyl pyridine, vinyl chloride, and vinylidene chloride.
  • (meth) acrylonitrile, N-cyclohexylmaleimide, or N-phenylmaleimide are examples of these compounds can be used alone or in combination of two or more.
  • the blending amount of the compound having an ethylenically unsaturated group other than the acrylic monomer is preferably 0 to 40% by mass, more preferably 5 to 35% by mass, and more preferably 10 to 30% by mass based on the mass of the component (A). Further preferred.
  • the glass transition temperature of the component (A) is not particularly limited, but is preferably ⁇ 30 ° C. to 150 ° C., more preferably 0 ° C. to 100 ° C., and further preferably 10 to 50 ° C., A temperature of 30 ° C. to 50 ° C. is particularly preferable.
  • the glass transition temperature of the component (A) is ⁇ 30 ° C. or higher, a laminated glass excellent in chipping resistance tends to be obtained.
  • the glass transition temperature of the component (A) is 150 ° C. or lower, the toughness of the interlayer film for laminated glass tends to be high, so that an interlayer film for laminated glass having excellent workability tends to be obtained.
  • the glass transition temperature is 10 ° C. or higher, there is a tendency that the adhesion of the polymer to the blade can be suppressed at the time of cutting the interlayer film for laminated glass. There is a tendency to be able to suppress cracking.
  • the glass transition temperature of the component (A) is a midpoint glass transition temperature measured using differential scanning calorimetry (DSC). Specifically, it is the midpoint glass transition temperature calculated by a method according to JIS K 7121: 1987, by measuring the change in calorie under the condition of a heating rate of 10 ° C./min.
  • the measurement temperature may be in a range including the glass transition temperature, and may be, for example, ⁇ 50 to 100 ° C. or ⁇ 80 to 80 ° C.
  • the glass transition temperature of the component (A) is a copolymer component for synthesizing the component (A), for example, the above-mentioned (meth) acrylic monomer having an epoxy group, (meth) acrylic monomer having no epoxy group, and (meth) It can adjust with the compounding ratio of the compound which has ethylenically unsaturated groups other than an acrylic monomer.
  • the epoxy equivalent of component (A) is preferably 200 to 2,000 g / eq.
  • the epoxy equivalent of the component (A) is 200 g / eq or more, the reaction between epoxy groups can be suppressed during storage of the resin composition for an interlayer film, so that the storage stability tends to be good.
  • the epoxy equivalent of (A) component is 2,000 g / eq or less, there exists a tendency for the chipping resistance of a laminated glass provided with the intermediate film formed from the resin composition for intermediate films to become favorable.
  • the epoxy equivalent is a value measured by a method based on JIS K 7236: 2001.
  • the weight average molecular weight of the component (A) is preferably 100,000 to 3,000,000.
  • the weight average molecular weight of the component (A) is 100,000 or more, the toughness of the interlayer film for laminated glass obtained tends to be improved.
  • the weight average molecular weight of the component (A) is 3,000,000 or less, the appearance tends to be good because bubbles are easily removed during the production of laminated glass.
  • the weight average molecular weight of the component (A) can be adjusted by a conventional method such as polymerization temperature, polymerization time, solvent used for polymerization, addition of a chain transfer agent, and the like.
  • the weight average molecular weight is a polystyrene equivalent value measured by gel permeation chromatography (GPC) and converted using a standard polystyrene calibration curve.
  • (A) There is no restriction
  • the polymerization method is not particularly limited, and examples thereof include a bulk polymerization method, a suspension polymerization method, an emulsion polymerization method, and a solution polymerization method. Polymerization can also be performed using an appropriate chain transfer agent or the like as required.
  • the curing agent used in this embodiment is a component that reacts with the epoxy group of component (A) to form a crosslinked structure.
  • the curing agent may be any one having a functional group capable of reacting with the epoxy group of component (A). Compound etc. are mentioned. Among these, it is preferable that a hardening
  • curing agent contains an acid anhydride compound from a viewpoint of latent curability and optical transparency. From the viewpoint of shortening the curing time, the curing agent preferably contains an imidazole compound. These compounds can be used alone or in combination of two or more.
  • the content of component (B) is preferably 0.01 to 50 parts by mass with respect to 100 parts by mass of component (A). If content of (B) component is 0.01 mass part or more, since the sclerosis
  • the acid anhydride compound examples include phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, benzophenone tetracarboxylic anhydride, ethylene glycol bisanhydro trimellitate, glycerol tris anhydro trimellitate, maleic anhydride, Tetrahydrophthalic anhydride, endomethylenetetrahydrophthalic anhydride, methylhymic anhydride, methylbutenyltetrahydrophthalic anhydride, dodecenyl succinic anhydride, hexahydrophthalic anhydride, succinic anhydride, methylcyclohexenedicarboxylic anhydride, methyltetrahydroanhydride And hexahydrophthalic anhydride substituted with an alkyl group such as phthalic acid, methylendomethylenetetrahydrophthalic anhydride, and methylhexahydrophthalic anhydride.
  • the hexahydrophthalic anhydride substituted with an alkyl group may be, for example, hexahydrophthalic anhydride substituted with an alkyl group having 1 to 9 carbon atoms.
  • the curing agent is tetrahydrophthalic anhydride, endomethylenetetrahydrophthalic anhydride, methylbutenyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylendomethylene.
  • It preferably contains at least one selected from the group consisting of tetrahydrophthalic anhydride and hexahydrophthalic anhydride substituted with an alkyl group, and at least one selected from the group consisting of hexahydrophthalic anhydride and methylhexahydrophthalic anhydride. More preferably, it includes seeds, and more preferably includes methylhexahydrophthalic anhydride.
  • the content of the acid anhydride compound is preferably 0.5 to 30 parts by mass, more preferably 1 to 25 parts by mass with respect to 100 parts by mass of the component (A). More preferred is 10 to 20 parts by mass. If the content of the acid anhydride compound is 0.5 parts by mass or more, the curability of the interlayer film for laminated glass formed from the resin composition for interlayer film can be improved. It can be expected that a laminated glass with high transparency can be obtained more easily, process time can be shortened and workability can be improved, and if it is 30 parts by mass or less, the storage stability of the resin composition for an interlayer film is improved Tend to be able to.
  • the content of the acid anhydride compound is preferably 40 to 70 parts by mass with respect to 100 parts by mass of the monomer unit derived from the (meth) acrylic monomer having an epoxy group in the component (A).
  • the amount is more preferably 45 to 65 parts by mass, further preferably 50 to 60 parts by mass, and more preferably 50 to 55 parts by mass.
  • imidazole compound examples include 2-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, and 2-phenyl-4.
  • 1-cyanoethyl-2-undecylimidazole 1-cyanoethyl-2-phenylimidazole, 2,4-diamino-6- [2′-methyl] are used from the viewpoint of the storage stability of the resin composition for an interlayer film.
  • the content is not particularly limited, but is 1.0 part by mass or less, 0.5 part by mass or less, 0.3 part by mass or less, and 0.1 part by mass with respect to 100 parts by mass of the component (A). It may be 2 parts by mass or less, or 0.03 parts by mass or less.
  • the content of the imidazole compound is within the above range, the curing temperature can be lowered and the curing time can be shortened, and the resin composition after curing tends to be prevented from yellowing. is there.
  • the intermediate film resin composition may further contain a curing accelerator as necessary.
  • a curing accelerator an organic phosphorus hardening accelerator is mentioned, for example.
  • Imidazole compounds can also function as curing accelerators, but are classified as curing agents in this specification.
  • organic phosphorus curing accelerators include triphenylphosphine, triparatolylphosphine, diphenylcyclohexylphosphine, tricyclohexylphosphine, ethyltriphenylphosphonium bromide, benzyltriphenylphosphonium chloride, 1,4-bisdiphenylphosphinobutane, 2 -Ethyl-4-methylimidazolium tetraphenylborate, 1,5-diazabicyclo [4.3.0] nonene-5-tetraphenylborate, tetraphenylphosphonium tetra-p-tolylborate, tetraphenylphosphonium tetraphenylborate, tri Phenylphosphine triphenylborane, tetraphenylphosphonium thiocyanate, tetraphenylphosphonium dicyanamide, n-butyltriphenyl
  • the content of the curing accelerator is not particularly limited, but is preferably 0.01 to 50 parts by mass with respect to 100 parts by mass of component (A).
  • the content of the curing accelerator is 0.01 parts by mass or more, the curability of the interlayer film for laminated glass formed from the resin composition for interlayer film of laminated glass can be improved, and therefore chipping resistance It is easier to obtain a laminated glass having a high thickness, shortening the process time and improving workability. If it is 50 parts by mass or less, the storage stability of the interlayer film resin composition of laminated glass should be improved. There is a tendency to be able to.
  • an additive may be further used as necessary.
  • an additive for example, a polymerization inhibitor, a silane coupling agent, surfactant, an inorganic filler, a flame retardant, a plasticizer, and another polymer are mentioned.
  • An example of a polymerization inhibitor is paramethoxyphenol.
  • silane coupling agents include methyltrimethoxysilane, methyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, ⁇ -aminopropyltrimethoxysilane, ⁇ -aminopropyltriethoxysilane, ⁇ -glycidoxy
  • examples include propyltrimethoxysilane, ⁇ -glycidoxypropylmethyldiethoxysilane, and ⁇ -glycidoxypropylmethyldiisopropenoxysilane.
  • the surfactant include polydimethylsiloxane compounds and fluorine compounds.
  • Examples of the inorganic filler include crushed silica, fused silica, mica, clay mineral, short glass fiber or fine powder, hollow glass, calcium carbonate, quartz powder, and metal hydrate.
  • the content of the inorganic filler may be 0.01 to 100 parts by mass, 0.05 to 50 parts by mass, or 0.1 to 30 parts by mass with respect to 100 parts by mass of the resin composition for an interlayer film.
  • effects such as low shrinkage, improved mechanical strength, and low thermal expansion coefficient tend to be obtained with respect to the resin composition for an interlayer film.
  • the inorganic filler may be treated with a commercially available surface treatment agent such as a coupling agent.
  • Examples of other polymers include epoxy resins, phenol resins, polyvinyl acetal resins, and ionomer resins.
  • epoxy resins phenol resins
  • polyvinyl acetal resins polyvinyl acetal resins
  • ionomer resins examples include epoxy resins, phenol resins, polyvinyl acetal resins, and ionomer resins.
  • an epoxy resin or a phenol resin When an epoxy resin or a phenol resin is used, the strength of the interlayer film for laminated glass tends to increase.
  • a polyvinyl acetal resin or an ionomer resin the adhesive force between the intermediate film and the glass plate tends to increase.
  • the intermediate film resin composition may be further diluted with an organic solvent as necessary.
  • the organic solvent is not particularly limited as long as it can dissolve the resin composition.
  • ketone organic solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone; ethyl acetate, butyl acetate, methyl lactate, lactic acid Ester organic solvents such as ethyl and ⁇ -butyrolactone; ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol monomethyl ether, propylene glycol dimethyl ether, diethylene glycol monomethyl ether, diethylene glycol monobutyl ether, diethylene glycol Polyhydric alcohol alkyl ether organic solvents such as dimethyl ether; ethylene glycol Polymethyl alcohol alkyl ether acetates such as nomethyl ether
  • the loss tangent tan ⁇ at a temperature of 0 ° C. and a frequency of 0.5 Hz is preferably 0.5 or less, more preferably 0.3 or less, and 0.2 or less. Is more preferable.
  • tan ⁇ is 0.5 or less, deformation of the interlayer film for laminated glass due to impact from the outside is suppressed, so that a laminated glass excellent in chipping resistance tends to be more easily obtained.
  • tan ⁇ is a numerical value measured by a dynamic viscoelasticity test in a tensile mode.
  • a film material prepared by adjusting an interlayer film for laminated glass to a thickness of 0.1 mm was heated at 150 ° C. for 2 hours, and then a dynamic viscoelasticity test apparatus (manufactured by TA Instrument Japan Co., Ltd., RSA- G2) can be used under the conditions of a sample width of 5 mm, a sample length of 5 mm, a strain amount of 0.05%, a temperature of 0 ° C., and a frequency of 0.5 Hz.
  • a dynamic viscoelasticity test apparatus manufactured by TA Instrument Japan Co., Ltd., RSA- G2
  • the temperature and time conditions for heating the film material vary depending on the types and amounts of the component (A) and the component (B) contained in the resin composition, but the resin composition can be sufficiently crosslinked without being decomposed and volatilized. If it is conditions, it will not restrict
  • the interlayer film for laminated glass according to the present embodiment is obtained by forming the above-mentioned resin composition for interlayer film of laminated glass into a film or a layer.
  • the interlayer film for laminated glass it may be obtained by curing or crosslinking the resin composition for interlayer film of laminated glass.
  • the interlayer film for laminated glass can be easily produced, for example, by applying a resin composition for interlayer film of laminated glass to a support film.
  • the resin composition for interlayer films of a laminated glass is diluted with an organic solvent, it can be produced by applying the resin composition to a support film and removing the organic solvent by heating and drying.
  • a film material for an interlayer film of laminated glass having a two-layer structure composed of a support film and an interlayer film for laminated glass can be obtained.
  • Protective film can be further affixed to the interlayer film for laminated glass provided on the support film, if necessary.
  • a film material for an interlayer film of laminated glass having a three-layer structure comprising a support film, an interlayer film for laminated glass, and a protective film can be obtained.
  • the film material for interlayer film of laminated glass obtained in this way can be easily stored, for example, by winding it into a roll.
  • a roll-shaped film material can be cut into a suitable size and stored as a sheet.
  • the support film is not particularly limited, and examples thereof include polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polyethylene, polypropylene, polyamide, and polyimide.
  • the support film is preferably polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polypropylene, polyamide, or polyimide.
  • it is preferable to use as the support film a film that has been subjected to a release treatment with a silicone compound, a fluorine compound, or the like.
  • the thickness of the support film may be appropriately changed depending on the intended flexibility, but is preferably 3 to 250 ⁇ m. If it is 3 ⁇ m or more, the film strength tends to be sufficient, and if it is 250 ⁇ m or less, sufficient flexibility tends to be obtained. From such a viewpoint, the thickness of the support film is more preferably 5 to 200 ⁇ m, and further preferably 7 to 150 ⁇ m.
  • the protective film is not particularly limited, and examples thereof include polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polyethylene, and polypropylene. Among these, from the viewpoint of flexibility and toughness, the protective film is preferably polyethylene terephthalate, polyethylene, or polypropylene. From the viewpoint of improving the peelability from the interlayer film for laminated glass, it is preferable to use as the protective film a film that has been subjected to a release treatment with a silicone compound, a fluorine compound, or the like.
  • the thickness of the protective film can be appropriately set depending on the intended flexibility, but is preferably 10 to 250 ⁇ m. If it is 10 ⁇ m or more, the film strength tends to be sufficient, and if it is 250 ⁇ m or less, sufficient flexibility tends to be obtained. From such a viewpoint, the thickness of the protective film is more preferably 15 to 200 ⁇ m, and further preferably 20 to 150 ⁇ m.
  • the thickness of the interlayer film for laminated glass is not particularly limited, but is preferably 10 to 10,000 ⁇ m. If the thickness is 10 ⁇ m or more, the thickness of the interlayer film for laminated glass or a cured product thereof tends to be sufficient because the thickness is sufficient. If the thickness is 10,000 ⁇ m or less, processing of the obtained interlayer film for laminated glass is performed. It tends to be easy. From such a viewpoint, the thickness of the interlayer film for laminated glass is more preferably 50 ⁇ m to 5,000 ⁇ m, and further preferably 100 to 1,000 ⁇ m.
  • the interlayer film for laminated glass is formed of a resin composition containing a combination of the component (A) and the component (B), chipping resistance and optical transparency can be achieved even if the thickness of the interlayer film is increased. Can be formed. From such a viewpoint, the thickness of the interlayer film for laminated glass may be 150 ⁇ m or more, 200 ⁇ m or more, 250 ⁇ m or more, 300 ⁇ m or more, 350 ⁇ m or more, or 400 ⁇ m or more.
  • the interlayer film for laminated glass can also be formed by film formation by melt molding such as extrusion molding.
  • the interlayer film for laminated glass is used for laminating in combination with functional layers having functionality such as antireflection layer, antifouling layer, dye layer, hard coat layer, and penetration-resistant layer of laminated glass, transparent protective plate, etc. May be.
  • the antireflection layer may be a layer having antireflection properties such that the visible light reflectance is 5% or less.
  • the antireflection layer may be a layer processed on a transparent substrate such as a transparent plastic film by a known antireflection method.
  • the antifouling layer is intended to make it difficult for the surface to get dirty.
  • the dye layer is a layer for increasing color purity.
  • the dye layer is used to reduce unnecessary wavelength light transmitted through the laminated glass.
  • the hard coat layer is provided to increase the surface hardness.
  • the hard coat layer may be, for example, an acrylic resin such as urethane acrylate or epoxy acrylate, or a film such as epoxy resin.
  • the hard coat layer may be a transparent protective plate such as a glass plate, an acrylic resin layer, or a polycarbonate resin layer and a hard coat layer laminated on the transparent protective plate.
  • the penetration-resistant layer is provided to prevent flying objects from penetrating the surface of the laminated glass.
  • the penetration-resistant layer can be formed of, for example, a polyvinyl acetal resin such as polyvinyl butyral or polyvinyl formal, an ethylene / vinyl acetate copolymer resin, or an ionomer resin.
  • the interlayer film for laminated glass is preferably arranged at a position adjacent to the glass on the side on which the flying object such as stepping stone collides.
  • the laminated glass according to the present embodiment forms, for example, a step of forming a laminated body having two glass plates and an intermediate film disposed therebetween, and forms a laminated glass by heating and pressing the laminated body. It can manufacture by the method including a process.
  • the interlayer film for laminated glass may be cured or cross-linked in the course of one or more steps of the laminate forming step and the laminate heating and pressing step.
  • a laminate having two glass plates and an intermediate film disposed between them is formed, for example, by preparing the above-mentioned film material having an intermediate film and sandwiching the intermediate film between two glass plates. be able to.
  • it can also form by apply
  • the step of curing or cross-linking the intermediate film is not particularly limited, but from the viewpoint of shortening the working time and reducing the appearance defects such as bubbles, the intermediate film disposed between the two glass plates. It is preferable to cure or crosslink in the step of forming a laminate having the above. From the viewpoint of reducing appearance defects such as bubbles, the laminate is heated or pressurized to form a laminated glass by curing and crosslinking. It is preferable to make it.
  • the method of curing or crosslinking the interlayer film is not particularly limited as long as the resin composition in the interlayer film can be cured or crosslinked, but is cured or crosslinked by heating at a temperature range of 80 to 300 ° C. for 10 minutes to 5 hours. It is preferable to make it.
  • the heating temperature is more preferably from 100 to 250 ° C., and even more preferably from 120 to 200 ° C., from the viewpoint of sufficiently proceeding with curing or crosslinking and reducing the energy cost.
  • the appropriate heating time varies depending on the heating temperature, but from the same viewpoint as the heating temperature, 20 minutes to 4 hours is more preferable, and 30 minutes to 2 hours is more preferable.
  • the resin composition for interlayer film of laminated glass and the interlayer film for laminated glass according to this embodiment have excellent flexibility and thermal fluidity before curing or crosslinking, followability to curved glass and pasting properties. Moreover, since the outstanding mechanical strength is expressed by making it postcure or bridge
  • resins A to I 300.0 g of butyl acrylate (BA), 550.0 g of dicyclopentanyl acrylate (FA-513AS, manufactured by Hitachi Chemical Co., Ltd.), and glycidyl methacrylate (GMA) 150 as a (meth) acrylic monomer having an epoxy group 0.0 g was mixed to obtain a monomer mixture.
  • a monomer mixture 5.0 g of lauroyl peroxide as a polymerization initiator and 1.0 g of n-octyl mercaptan as a chain transfer agent were dissolved to obtain a mixture containing the monomer.
  • Resin F (Meth) acrylic copolymer having an epoxy group as in the case of Resin A, except that the monomer mixture was a monomer mixture of 400.0 g BA, 450.0 g FA-513AS, and 150.0 g GMA. Resin F particles containing coalescence were obtained.
  • Resin G Resin G particles containing an acrylic copolymer containing no epoxy group are the same as Resin A except that the monomer mixture is a monomer mixture of 550.0 g BA and 450.0 g FA-513AS. Obtained.
  • Resin H Polyvinyl butyral (PVB) resin having a half-value width of a peak corresponding to a hydroxyl group obtained by measuring an infrared absorption spectrum of 245 cm ⁇ 1 (degree of acetalization 68.0 mol%, ratio of vinyl acetate component 0.6 mol %) 100 parts by mass and 38 parts by mass of triethylene glycol di-2-ethylhexanoate (3GO) as a plasticizer were mixed. The mixture was sufficiently melt-kneaded with a mixing roll to obtain Resin H.
  • PVB Polyvinyl butyral
  • Resin I An ionomer resin (an ionomer resin formed from an ethylene-methacrylic acid copolymer and zinc ions, made by Mitsui DuPont Polychemical Co., Ltd., Himiran 1705) was used as the resin I.
  • the obtained resin varnish was dropped on the surface of the polyethylene terephthalate film as the support film (heavy release separator) that had been subjected to the release treatment, a coating film was formed using a bar coater, and the coating film was heated at 80 ° C. for 30 minutes. By drying by heating, a resin layer (interlayer film for laminated glass) having a thickness of 100 ⁇ m (0.1 mm) formed from the resin composition for interlayer film was obtained.
  • Example 2 to 14 and Comparative Example 1 Using the resin compositions for laminated glass interlayer films shown in Tables 2 to 4 below, an interlayer film for laminated glass, a film material for interlayer films of laminated glass, and laminated glass were produced in the same manner as in Example 1.
  • Example 8 1-cyanoethyl-2-phenylimidazole (2PZCN, manufactured by Shikoku Kasei Kogyo Co., Ltd.) was used as a curing agent.
  • the PVB resin layer was cut into a size of 110 mm in length and 110 mm in width, it was attached to a float glass having a length of 110 mm, a width of 110 mm, and a thickness of 1.6 mm so that the four sides overlapped, and the whole was pressed with a roller from above.
  • a float glass having a length of 110 mm, a width of 110 mm, and a thickness of 2.7 mm was pasted on the exposed resin layer side so that the four sides overlapped, and the whole was pressed with a roller from above. Thereby, the laminated body of float glass / PVB resin layer / float glass was obtained.
  • the obtained laminate was heated for 25 minutes using a vacuum laminator set to 125 ° C., and then heated and pressurized using an autoclave set to 150 ° C. under a pressure of 115 N / cm 2 for 120 minutes.
  • a laminated glass having a structure of float glass (2.7 mm) / PVB resin layer / float glass (1.6 mm) was obtained. Five laminated glasses were produced by the same operation.
  • the ionomer resin layer was cut into a size of 110 mm in length and 110 mm in width, it was attached to a float glass having a length of 110 mm, a width of 110 mm, and a thickness of 1.6 mm so that the four sides overlapped, and the whole was pressed with a roller from above.
  • a float glass having a length of 110 mm, a width of 110 mm, and a thickness of 2.7 mm was pasted on the exposed resin layer side so that the four sides overlapped, and the whole was pressed with a roller from above.
  • a laminate of float glass / ionomer resin layer / float glass was obtained.
  • the obtained laminate was heated for 25 minutes using a vacuum laminator set to 125 ° C., and then heated and pressurized using an autoclave set to 150 ° C. under a pressure of 115 N / cm 2 for 120 minutes.
  • a laminated glass having a structure of float glass (2.7 mm) / ionomer resin layer / float glass (1.6 mm) was obtained. Five laminated glasses were produced by the same operation.
  • Example 2-1 ⁇ Production of laminated glass>
  • 0.3 g of 2-ethyl-4-methylimidazole (2E4MZ, Shikoku Kasei Kogyo Co., Ltd.) was uniformly dissolved in 100.0 g of methyl ethyl ketone to obtain a resin varnish.
  • the obtained resin varnish was dropped on the surface of the polyethylene terephthalate film as the support film (heavy release separator) that had been subjected to the release treatment, a coating film was formed using a bar coater, and the coating film was heated at 80 ° C. for 30 minutes. Drying by heating gave an acrylic resin layer A having a thickness of 100 ⁇ m (0.1 mm).
  • the acrylic resin layer A is covered with a release surface of a polyethylene terephthalate film as a protective film (lightly peeled separator), and is attached by pressing it with a 1.0 kgf hand roller.
  • Support film / acrylic resin A film material for an acrylic resin layer having a configuration of layer A (first resin layer) / protective film was obtained.
  • a PVB resin layer (second resin layer) having a thickness of 0.4 mm was obtained in the same manner as in Reference Example 1.
  • the acrylic resin layer film material was cut into a size of 110 mm in length and 110 mm in width.
  • the light release separator of this acrylic resin layer film material was peeled off to expose the resin layer.
  • a float glass having a length of 110 mm, a width of 110 mm, and a thickness of 1.6 mm was pasted on the exposed resin layer so that the four sides overlapped, and the whole was pressed with a roller from above.
  • the heavy release separator on the other side was peeled off to expose the resin layer.
  • a PVB resin layer cut to a size of 110 mm in length and 110 mm in width was stuck on the exposed resin layer so that the four sides overlapped, and the whole was pressed with a roller from above.
  • float glass having a length of 110 mm, a width of 110 mm, and a thickness of 2.7 mm was stuck on the exposed PVB resin layer so that the four sides overlapped, and the whole was pressed with a roller from above.
  • a laminate of float glass (1.6 mm) / acrylic resin layer A (0.1 mm) / PVB resin layer (0.4 mm) / float glass (2.7 mm) was obtained.
  • the obtained laminate was heated for 25 minutes using a vacuum laminator set to 125 ° C., and then heated and pressurized using an autoclave set to 150 ° C. under a pressure of 115 N / cm 2 for 120 minutes.
  • a laminated glass was obtained. Five laminated glasses were produced by the same operation.
  • Example 2-2 The support film / acrylic was the same as in Example 2-1, except that the resin A particles were used as component (A) and the amount of HN-5500 used as component (B) was changed to 8.0 g.
  • Example 2-3 In the same manner as in Example 2-1, an acrylic resin layer film material having a configuration of support film / acrylic resin layer A (first resin layer) / protective film was obtained.
  • the obtained film material for an acrylic resin layer was cut into a size of 110 mm in length and 110 mm in width.
  • the light release separator of this acrylic resin layer film material was peeled off to expose the resin layer.
  • a float glass having a length of 110 mm, a width of 110 mm, and a thickness of 1.6 mm was stuck on the exposed oil layer so that the four sides overlapped, and the whole was pressed with a roller from above.
  • the heavy release separator on the other side was peeled off to expose the resin layer.
  • a float glass having a length of 110 mm, a width of 110 mm, and a thickness of 2.7 mm was stuck on the exposed resin layer so that the four sides overlapped, and the whole was pressed with a roller from above.
  • a laminate of float glass (1.6 mm) / acrylic resin layer (0.1 mm) / float glass (2.7 mm) was obtained.
  • the obtained laminate was heated for 25 minutes using a vacuum laminator set to 125 ° C., and then heated and pressurized using an autoclave set to 150 ° C. under a pressure of 115 N / cm 2 for 120 minutes.
  • a laminated glass was obtained. Five laminated glasses were produced by the same operation.
  • the chipping resistance of the laminated glass indicates that A is the best and D is the worst.
  • T.T 90.0% or more B: 80.0% or more, less than 90.0% C: 70.0% or more, less than 80.0% D: Less than 70.0%
  • Haze A: Less than 0.5 B: 0.5 or more, less than 2.0 C: 2.0 or more, less than 3.0 D: 3.0 or more
  • YI value A: Less than 0.5 B: 0.5 or more, less than 1.0 C: 1.0 or more, less than 2.0 D: 2.0 or more
  • the penetration resistance of laminated glass was evaluated by a test according to JIS R 3212: 2015 automotive safety glass test method.
  • the laminated glass for penetration resistance test was left in a room at a temperature of 23 ° C. for 4 hours.
  • the laminated glass was placed on the horizontally supported support frame so that the surface (the surface on the float glass side having a thickness of 2.7 mm) which becomes the inside of the vehicle was on top.
  • a steel ball having a mass of 2.26 kg and a diameter of 82 mm was dropped from a height of 4 m without applying force toward the center of the laminated glass (within 25 mm from the center point).
  • the penetration resistance of the laminated glass was evaluated with “B” when the steel ball penetrated within 5 seconds after the impact, and “A” when the steel ball did not penetrate after 5 seconds. The results are shown in Table 5 below.
  • the laminated glasses of Examples 1 to 14 were superior in chipping resistance compared to the laminated glasses of Comparative Example 1 and Reference Examples 1 and 2. From this evaluation result, it was confirmed that the laminated glass resin composition for laminated glass and the laminated glass interlayer film of the present invention can form laminated glass having high chipping resistance. In addition, it was confirmed that the laminated glasses of Examples 1 and 7 to 14 had excellent chipping resistance and equivalent optical characteristics as compared with the laminated glasses of Comparative Example 1 and Reference Examples 1 and 2. Further, it was confirmed that the laminated glass of Examples 2-1 and 2-2 was excellent in penetration resistance in addition to chipping resistance as compared with the laminated glass of Example 2-3 and Reference Example 1. .

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Joining Of Glass To Other Materials (AREA)
  • Laminated Bodies (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Devices For Indicating Variable Information By Combining Individual Elements (AREA)

Abstract

Le but de la présente invention est de fournir une composition de résine pour une couche intermédiaire de verre feuilleté, la composition de résine permettant de produire un verre feuilleté ayant d'excellentes propriétés anti-éclat. L'invention concerne une composition de résine pour une couche intermédiaire de verre feuilleté, la composition de résine : étant utilisée pour former une couche intermédiaire disposée entre deux panneaux de verre disposés l'un en face de l'autre ; et comprenant (A) un copolymère (méth)acrylique ayant un groupe époxy et (B) un agent de durcissement.
PCT/JP2019/012960 2018-03-29 2019-03-26 Composition de résine pour couche intermédiaire de verre feuilleté, couche intermédiaire de verre feuilleté, matériau de film pour couche intermédiaire de verre feuilleté, verre feuilleté et procédé de fabrication de verre feuilleté WO2019189235A1 (fr)

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Publication number Priority date Publication date Assignee Title
JP2022006687A (ja) * 2020-06-24 2022-01-13 日東電工株式会社 光学積層体および画像表示装置
CN118159506A (zh) * 2021-10-27 2024-06-07 Ａｇｃ株式会社 玻璃板、车辆用窗玻璃和夹层玻璃

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4867342A (fr) * 1971-12-17 1973-09-14
JPS5034032A (fr) * 1973-07-25 1975-04-02
JPS5051541A (fr) * 1973-09-06 1975-05-08
US4956227A (en) * 1988-11-16 1990-09-11 Nippon Sheet Glass Co., Ltd. Laminated structure
JPH03257044A (ja) * 1990-03-08 1991-11-15 Asahi Glass Co Ltd ホログラム封入合せガラスの製造方法
JPH07165445A (ja) * 1993-01-28 1995-06-27 Mitsubishi Rayon Co Ltd 合わせガラスの製造方法
WO2010090212A1 (fr) * 2009-02-03 2010-08-12 積水化学工業株式会社 Film intermédiaire pour verre feuilleté, procédé de production d'un film intermédiaire pour verre feuilleté et verre feuilleté
WO2015125595A1 (fr) * 2014-02-19 2015-08-27 シーアイ化成株式会社 Film de résine

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4867342A (fr) * 1971-12-17 1973-09-14
JPS5034032A (fr) * 1973-07-25 1975-04-02
JPS5051541A (fr) * 1973-09-06 1975-05-08
US4956227A (en) * 1988-11-16 1990-09-11 Nippon Sheet Glass Co., Ltd. Laminated structure
JPH03257044A (ja) * 1990-03-08 1991-11-15 Asahi Glass Co Ltd ホログラム封入合せガラスの製造方法
JPH07165445A (ja) * 1993-01-28 1995-06-27 Mitsubishi Rayon Co Ltd 合わせガラスの製造方法
WO2010090212A1 (fr) * 2009-02-03 2010-08-12 積水化学工業株式会社 Film intermédiaire pour verre feuilleté, procédé de production d'un film intermédiaire pour verre feuilleté et verre feuilleté
WO2015125595A1 (fr) * 2014-02-19 2015-08-27 シーアイ化成株式会社 Film de résine

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