WO2018079720A1 - Verre feuilleté et son procédé de production, et composition de résine photodurcissable pour couche intermédiaire pour verre feuilleté - Google Patents

Verre feuilleté et son procédé de production, et composition de résine photodurcissable pour couche intermédiaire pour verre feuilleté Download PDF

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WO2018079720A1
WO2018079720A1 PCT/JP2017/038931 JP2017038931W WO2018079720A1 WO 2018079720 A1 WO2018079720 A1 WO 2018079720A1 JP 2017038931 W JP2017038931 W JP 2017038931W WO 2018079720 A1 WO2018079720 A1 WO 2018079720A1
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glass
glass plate
plate
laminated
resin layer
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PCT/JP2017/038931
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English (en)
Japanese (ja)
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直己 高原
吉田　明弘
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日立化成株式会社
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Priority to JP2018547789A priority Critical patent/JPWO2018079720A1/ja
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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

Definitions

  • the present invention relates to a laminated glass, a method for producing the same, and a photocurable resin composition for an interlayer film of laminated glass.
  • laminated glass is widely used as glass for vehicles such as automobiles, aircraft, buildings, etc., even if it is damaged by an external impact, it is safe because the glass fragments do not scatter. Yes.
  • Laminated glass is generally a laminate having at least one pair of glass plates and an intermediate film that is interposed between them and bonds the glass plates together.
  • An example of the interlayer film for laminated glass is a film formed from a polyvinyl acetal resin such as a polyvinyl butyral resin plasticized with a plasticizer (Patent Documents 1 to 3).
  • an object of the present invention is to achieve both sufficiently excellent optical properties and high splitting properties for laminated glass to which a transparent plastic plate is applied.
  • One aspect of the present invention provides a laminated glass including two opposing glass plates and an intermediate film sandwiched between the two glass plates.
  • One of the two glass plates is a transparent plastic plate, and the other is an inorganic glass plate.
  • the intermediate film is a cured product of a photocurable resin composition containing (A) an acrylic polymer, (B) an acrylic monomer, and (C) a photopolymerization initiator.
  • the impact strength measured by an impact resistance test in which a hard sphere is dropped toward the laminated glass may be 0.03 J / cm 2 or more.
  • the acrylic polymer may have a weight average molecular weight of 100,000 or more.
  • laminated glass including a combination of a transparent plastic plate and an inorganic glass plate
  • (meth) acrylate means at least one of “acrylate” or “methacrylate” 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.
  • FIG. 1 is a schematic cross-sectional view showing an embodiment of a laminated glass.
  • a laminated glass 1 shown in FIG. 1 has two glass plates 11 and 12 facing each other and an intermediate film 5 sandwiched between the two glass plates 11 and 12.
  • the glass plate 11 also referred to as “first glass plate”
  • the intermediate film 5 and the glass plate 12 (also referred to as “second glass plate”) are laminated in this order.
  • One of the two glass plates 11 and 12 can be a transparent plastic plate and the other can be an inorganic glass plate.
  • the inorganic glass plate can be selected from those usually used as a glass plate constituting the laminated glass. By providing the inorganic glass plate, the surface of the laminated glass can have good scratch resistance.
  • the inorganic glass plate may be, for example, a float glass, a tempered glass (air-cooled tempered glass, chemically tempered glass, etc.), or a multilayer glass plate.
  • transparent plastic plate a plastic plate having optical properties such as transparency suitable for laminated glass is used.
  • transparent plastic plates include polycarbonate resin plates (PC plates), polymethyl methacrylate resin plates (PMMA plates), cyclopolyolefin resin plates (COP plates), polyethylene terephthalate resin plates (PET plates), polyethylene plates (PE plates) , Polypropylene plate (PP plate), polystyrene plate (PS plate), and triacetyl cellulose plate (TAC plate).
  • PC plates polycarbonate resin plates
  • PMMA plates polymethyl methacrylate resin plates
  • COP plates cyclopolyolefin resin plates
  • PET plates polyethylene terephthalate resin plates
  • PE plates polyethylene plates
  • PE plates Polypropylene plate
  • PS plate polystyrene plate
  • TAC plate triacetyl cellulose plate
  • the intermediate film 5 is a cured product of a photocurable resin composition containing an acrylic polymer.
  • the intermediate film 5 is in direct contact with most of the main surfaces of the adjacent glass plates 11 and 12 on the side of the intermediate film 5 (for example, 90% by area or more of the main surfaces), so that the two glass plates 11 and 12 are in contact with each other. Bonding together. Details of the photocurable resin composition for forming the intermediate film 5 will be described later.
  • the thickness of the intermediate film 5 may be 10 to 5000 ⁇ m, or 25 to 1000 ⁇ m.
  • the light transmittance of each of the glass plates 11 and 12 and the intermediate film 5 in the visible light region may be 80% or more, 90% or more, or 95% or more.
  • the light transmittance of the entire laminated glass 1 with respect to light rays in the visible light region may be 80% or more, 90% or more, or 95% or more.
  • the upper limit of light transmittance is 100%.
  • the impact strength measured by an impact resistance test in which a hard sphere is dropped toward the laminated glass 1 may be 0.03 J / cm 2 or more.
  • the laminated glass exhibits an impact strength of 0.03 J / cm 2 or more in at least an impact resistance test in which a hard sphere is dropped toward the laminated glass from the inorganic glass plate side.
  • the laminated glass may exhibit an impact strength of 0.03 J / cm 2 or more in an impact resistance test in which a hard sphere is dropped from either side of the two glass plates toward the laminated glass.
  • Laminated glass exhibiting high impact strength can have sufficient splitting resistance.
  • the upper limit of impact strength is not particularly limited, but is usually 10 J / cm 2 or less. Details of the method of measuring the impact strength will be described in Examples described later.
  • the impact strength of the laminated glass can be set to a predetermined value or more by appropriately setting the thicknesses of the glass plate and the interlayer film.
  • the thickness of the transparent plastic plate may be 0.1 to 100 mm, 0.5 to 10 mm, or 0.5 to 5 mm.
  • the thickness of the inorganic glass plate may be 0.1 to 50 mm, 0.5 to 30 mm, 1 to 20 mm, or 2 to 10 mm.
  • the total thickness of the laminated glass 1 is usually 0.5 to 1000 mm or 1 to 15 mm in many cases.
  • the laminated glass of the present embodiment having such a thickness is easy to show high impact strength while being sufficiently light compared to the laminated glass composed only of the inorganic glass plate and the intermediate film.
  • the intermediate film 5 may have at least one layer that satisfies the following viscoelasticity requirements (a) and (b).
  • the viscoelasticity of the intermediate film 5 itself may satisfy these requirements.
  • (A) The storage elastic modulus at a reference temperature of 25 ° C. and a frequency of 1000 Hz is 1 ⁇ 10 5 to 1 ⁇ 10 8 Pa.
  • the frequency range of 100 to 100,000 Hz corresponds to the strain rate generated in the laminated glass when a hard sphere that has fallen freely from a height of about several centimeters to a few tens of centimeters collides with the laminated glass. Therefore, for example, when the maximum value of the loss coefficient is larger than 0.4 in the range of the reference temperature of 25 ° C. and the frequency of 100 to 100,000 Hz, higher splitting properties are more easily exhibited than the glass single plate.
  • the maximum value of the loss factor may be 0.5 or more, 1.1 or less, or 1.0 or less.
  • the storage elastic modulus at a reference temperature of 25 ° C. and a frequency of 1000 Hz is 1 ⁇ 10 5 or more, particularly excellent effects are obtained in terms of mechanical properties and reliability (heat resistance, weather resistance).
  • the storage elastic modulus at a reference temperature of 25 ° C. and a frequency of 1000 Hz is 1 ⁇ 10 8 Pa or less, particularly excellent effects are obtained in terms of impact resistance.
  • the storage elastic modulus at a reference temperature of 25 ° C. and a frequency of 1000 Hz may be 1.5 ⁇ 10 5 or more, or 5 ⁇ 10 6 Pa or less.
  • the values of the storage elastic modulus and the loss coefficient (tan ⁇ ) can be obtained from a composite curve (master curve) obtained from dynamic viscoelasticity measurement and a time-temperature conversion rule.
  • the dynamic viscoelasticity measurement is, for example, a tensile measurement according to a method in accordance with JIS K 0129: 2005 under conditions of a temperature of ⁇ 70 to 100 ° C., a frequency of 0.05 Hz, 0.5 Hz, 5 Hz or 50 Hz, and a strain amount of 1% Done in mode.
  • a master curve is created by setting the reference temperature to 25 ° C. using the WLF method or the Arrhenius law. The maximum value of tan ⁇ can be read.
  • the thickness of the glass plate and the intermediate film is within the above range while maintaining sufficient optical properties of the laminated glass.
  • the impact strength of the laminated glass can be easily increased.
  • the weight average molecular weight of the acrylic polymer being 100,000 or more can also contribute to the improvement of impact strength.
  • the peel strength between the intermediate film 5 and the glass plate 11 or the glass plate 12 may be 5 N / 10 mm or more, 8 N / 10 mm or more, 10 N / 10 mm or more, or 30 N / 10 mm or less.
  • the peel strength here is measured by a 180 degree peel test for 3 seconds at a peel rate of 300 mm / min at 25 ° C. using a tensile tester (trade name “Tensilon RTC-1210” manufactured by Orientec Co., Ltd.). Mean value.
  • the laminated glass is not limited to the embodiment shown in FIG. 1 and can be appropriately changed.
  • the laminated glass may further include an inorganic glass plate and / or a transparent plastic plate as an additional glass plate (such as a third glass plate).
  • an additional intermediate film is usually provided also between the additional glass plate and the adjacent glass plate.
  • the additional intermediate film may also be a cured product of the same photocurable resin composition as the intermediate film 5.
  • the laminated glass may further have various functional layers selected from an antireflection layer, an antifouling layer, a dye layer, a hard coat layer, and the like.
  • the antireflection layer is a layer having antireflection properties such that the visible light reflectance of the laminated glass is 5% or less.
  • the antireflection layer can be, for example, a transparent substrate such as a transparent plastic film treated by a known antireflection method.
  • the antifouling layer is provided in order to make the surface difficult to get dirty.
  • the dye layer is provided in order to reduce unnecessary wavelength light transmitted through the laminated glass.
  • the hard coat layer is provided to increase the surface hardness of the laminated glass.
  • the hard coat layer may be a laminated film having a base film such as a polyethylene film and a film made of an acrylic resin (urethane acrylate, epoxy acrylate, etc.) or an epoxy resin formed on the base film.
  • the photocurable resin composition for interlayer films of laminated glass may contain (A) an acrylic polymer, (B) an acrylic monomer, and (C) a photopolymerization initiator.
  • This photocurable resin composition can contribute to the high splitting property of the laminated glass.
  • the intermediate film formed from this photocurable resin composition hardly causes whitening of the laminated glass even in a high humidity environment, and is excellent in terms of reliability.
  • the glass plates can be bonded to each other at normal temperature and normal pressure, so that the glass plates having different thermal expansion coefficients Even if they are pasted together, defects are unlikely to occur. Therefore, a laminated glass having good optical properties can be easily obtained by forming an intermediate film using this photocurable resin composition.
  • An acrylic polymer (hereinafter sometimes referred to as “component (A)”) is a polymer mainly composed of a monomer having one (meth) acryloyl group in the molecule.
  • the acrylic polymer may be a homopolymer of one kind of monomer or a copolymer composed of two or more kinds of monomers.
  • the acrylic polymer may have a weight average molecular weight of 100,000 or more.
  • the weight average molecular weight of the acrylic polymer may be 110,000 or more, or 120,000 or more.
  • the upper limit of the weight average molecular weight of the acrylic polymer is not particularly limited, but may be 1,000,000 or less. If the weight average molecular weight of the acrylic polymer is 1,000,000 or less, a laminated glass showing a low haze and a high peel strength as well as an excellent impact strength is particularly easily obtained.
  • a weight average molecular weight means a standard polystyrene conversion value measured by gel permeation chromatography.
  • the glass transition temperature (Tg) of the acrylic polymer may be 0 ° C. or lower or ⁇ 10 ° C. or lower. If the Tg of the acrylic polymer is low, the impact strength of the laminated glass tends to be high. From the same viewpoint, the Tg of the acrylic polymer may be ⁇ 15 ° C. or lower.
  • the lower limit of Tg of the acrylic polymer is not particularly limited. Usually, it is ⁇ 40 ° C. or higher.
  • the monomer having a (meth) acryloyl group constituting the acrylic polymer is typically a (meth) acryloyloxy group (CH 2 ⁇ CHC ( ⁇ O) O— or CH 2 ⁇ C (CH 3 ) C ( ⁇ O ) A monofunctional monomer having one O-).
  • (meth) acrylic acid methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, n-pentyl ( (Meth) acrylate, n-hexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isodecyl (meth) acrylate, dodecyl (meth) acrylate (n-lauryl ( (Meth) acrylate), isomyristyl (meth) acrylate, stearyl (meth) acrylate and alkyl (meth) acrylate having an alkyl group such as isostearyl acrylate (the alkyl group
  • the acrylic polymer may be a copolymer containing alkyl (meth) acrylate and (meth) acrylate having a hydroxyl group as monomer units.
  • monomers constituting the acrylic polymer include (meth) acrylamide and derivatives thereof.
  • Acrylamide derivatives include (meth) acryloylmorpholine; N, N-dimethylaminopropyl (meth) acrylamide, N, N-dimethyl (meth) acrylamide, N-isopropyl (meth) acrylamide, N, N-diethyl (meth) acrylamide And N-hydroxyethyl (meth) acrylamide.
  • the acrylic polymer may contain as a monomer unit a copolymerizable monomer copolymerizable with a monomer having a (meth) acryloyl group. However, usually 80% by mass or more, or 90% by mass or more of the whole acrylic polymer is composed of monomer units derived from a monomer having a (meth) acryloyl group.
  • the copolymerization monomer include styrene, 4-methylstyrene, vinylpyridine, vinylpyrrolidone, vinyl acetate, cyclohexylmaleimide, phenylmaleimide, and maleic anhydride.
  • the acrylic polymer may have a (meth) acryloyl group having polymerization reactivity.
  • the acrylic polymer having a (meth) acryloyl group can further toughen the cured product of the photocurable resin composition.
  • the acrylic polymer having a (meth) acryloyl group is classified as one type of acrylic polymer, not the acrylic monomer as the component (B).
  • the acrylic polymer having a (meth) acryloyl group includes a main chain containing a monomer having one (meth) acryloyl group in the molecule as a monomer unit, a urethane bond bonded to the main chain, and the urethane bond. It may be a modified acrylic polymer having a (meth) acryloyloxy group bonded to the main chain.
  • This modified acrylic polymer can be a reaction product of an acrylic polymer having a hydroxyl group in the side chain and an isocyanate compound.
  • the acrylic polymer having a hydroxyl group in the side chain may contain, as a monomer unit, at least one monomer selected from, for example, 2-hydroxyethyl acrylate, 4-hydroxybutyl acrylate, and 6-hydroxyhexyl acrylate.
  • the modified acrylic polymer can further strengthen the intermediate film formed by making the entanglement of the molecular chains of the acrylic polymer more complicated.
  • the content of the acrylic polymer may be 1% by mass or more, 10% by mass or more, or 20% by mass or more based on the total amount of the photocurable resin composition.
  • the content of the acrylic polymer may be 80% by mass or less, 50% by mass or less, or 30% by mass or less based on the total amount of the photocurable resin composition.
  • the elongation percentage of the cured product of the photocurable resin composition tends to be further improved.
  • the photocurable resin composition tends to have good coatability.
  • An acrylic monomer (hereinafter also referred to as “component (B)”) is a compound having one or more (meth) acryloyl groups.
  • Specific examples of the acrylic monomer include (meth) acrylic acid; (meth) acrylic amide; (meth) acryloylmorpholine; methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) ) Acrylate, tert-butyl (meth) acrylate, n-pentyl (meth) acrylate, n-hexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isodecyl Alkyl (meth) acrylates (alkyl groups) of alkyl groups such as
  • Carbon number may be 1-18); alkanediol di (meth) acrylate such as ethylene glycol di (meth) acrylate, butanediol (meth) acrylate, nonanediol di (meth) acrylate (alkane having carbon number of 1 to 18); trimethylolpropane tri (meth) acrylate, tetramethylolmethane tri (meth) acrylate, tetramethylolmethanetetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa
  • a polyfunctional acrylate having three or more (meth) acryloyl groups such as (meth) acrylate and the like and an alkane polyol residue bonded thereto; glycidyl methacrylate; alkenyl such as 3-butenyl (meth) acrylate (meta Acrylate (the al
  • the (meth) acrylate having a siloxane skeleton may be collectively referred to as an aliphatic (meth) acrylate.
  • Alkoxy polyalkylene glycol (meth) acrylate, polyalkylene glycol mono (meth) acrylate, polyalkylene glycol di (meth) acrylate, and (meth) acrylate having an isocyanuric ring skeleton are collectively referred to as heteroatom (meth) acrylate.
  • heteroatom (meth) acrylate Alkoxy polyalkylene glycol (meth) acrylate, polyalkylene glycol mono (meth) acrylate, polyalkylene glycol di (meth) acrylate, and (meth) acrylate having an isocyanuric ring skeleton.
  • the photopolymerization initiator (hereinafter, also referred to as “component (C)”) is a compound that initiates or accelerates the curing reaction by irradiation with active energy rays.
  • the active energy rays can be, for example, ultraviolet rays, electron beams, ⁇ rays, ⁇ rays, or ⁇ rays.
  • the photopolymerization initiator is not particularly limited, and usual materials such as benzophenone, anthraquinone, benzoyl, sulfonium salt, diazonium salt, and onium salt can be used.
  • photopolymerization initiator examples include benzophenone, N, N, N ′, N′-tetramethyl-4,4′-diaminobenzophenone (Michler ketone), N, N, N ′, N′-tetraethyl-4, 4'-diaminobenzophenone, 4-methoxy-4'-dimethylaminobenzophenone, ⁇ -hydroxyisobutylphenone, 2-ethylanthraquinone, t-butylanthraquinone, 1,4-dimethylanthraquinone, 1-chloroanthraquinone, 2,3-dichloro Anthraquinone, 3-chloro-2-methylanthraquinone, 1,2-benzoanthraquinone, 2-phenylanthraquinone, 1,4-naphthoquinone, 9,10-phenanthraquinone, thioxanthone, 2-
  • the photopolymerization initiator is 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, 1 ⁇ -hydroxyalkylphenone compounds such as [4- (2-hydroxyethoxy) -phenyl] -2-hydroxy-2-methyl-1-propan-1-one; bis (2,4,6-trimethylbenzoyl) -Acylphosphine oxide compounds such as phenylphosphine oxide, bis (2,6-dimethoxybenzoyl) -2,4,4-trimethyl-pentylphosphine oxide, 2,4,6-trimethylbenzoyl-diphenylphosphine oxide Oligo (2-hydroxy-2-methyl-1- (4- (1-methylvinyl Phenyl) propanone) or a combination thereof.
  • the content of the photopolymerization initiator may be 0.1 to 5% by mass, 0.2 to 3% by mass, or 0.3 to 2% by mass with respect to the total amount of the photocurable resin composition. .
  • the content of the photopolymerization initiator is 0.1% by mass or more, photopolymerization can be particularly favorably started.
  • the content of the photopolymerization initiator is 5% by mass or less, the intermediate film tends to be less yellowish.
  • the resin composition for an interlayer film of the present embodiment may further contain other components such as various additives in addition to the components (A) to (C) as necessary.
  • various additives include plasticizers, polymerization inhibitors, antioxidants, light stabilizers, silane coupling agents, surfactants, leveling agents, and inorganic fillers.
  • the polymerization inhibitor is added for the purpose of enhancing the storage stability of the resin composition, and an example thereof is paramethoxyphenol.
  • Antioxidants are added for the purpose of improving the heat resistant colorability of the interlayer film, and examples thereof include phosphorus-based; phenol-based; thiol-based antioxidants such as triphenyl phosphite.
  • the light stabilizer is added for the purpose of increasing the resistance to active energy rays such as ultraviolet rays, and an example thereof is HALS (Hindered Amine Light Stabilizer).
  • Silane coupling agents are added to improve adhesion to glass plates.
  • Examples include methyltrimethoxysilane, methyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, and ⁇ -aminopropyltrimethoxysilane. , ⁇ -aminopropyltriethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropylmethyldiethoxysilane, and ⁇ -glycidoxypropylmethyldiisopropenoxysilane.
  • the surfactant is added to control the peelability from the base material, and examples thereof include a polydimethylsiloxane compound and a fluorine compound.
  • the leveling agent is added to impart flatness to the resin composition, and examples thereof include compounds that lower the surface tension of silicon-based and fluorine-based compounds. These additives may be used alone, or a plurality of additives may be used in combination. The content of these additives is generally about 0.01 to 5% by mass with respect to the total amount of the resin composition.
  • the inorganic filler can be used as long as appropriate transparency of the laminated glass is maintained.
  • examples of the inorganic filler include crushed silica, fused silica, mica, clay mineral, short glass fiber, fine glass 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.
  • the photocurable resin composition for an interlayer film can be produced, for example, by mixing an acrylic polymer and an additive that is added as necessary and stirring them.
  • a laminated glass having the intermediate film 5 illustrated in FIG. 1 is manufactured by, for example, the method according to the embodiment shown in FIG. 2, FIG. 3, or FIG. can do.
  • the method shown in FIG. 2 includes a step (a) of applying a photocurable resin composition to the surface of the first glass plate 11 and forming a photocurable resin layer 5a on the first glass plate 11. Then, the first glass plate 11 and the second glass plate 12 are bonded together with the resin layer 5a interposed therebetween to obtain a laminate 1a having the first glass plate, the resin layer 5a, and the second glass plate.
  • the ultraviolet rays may be irradiated from either side of the first glass plate 11 and the second glass plate 12.
  • the method shown in FIG. 3 includes a step (a) of applying a photocurable resin composition to the surface of the first glass plate 11 and forming a photocurable resin layer 5a on the first glass plate 11.
  • a peelable protective sheet may be placed on the resin layer 5a, and the resin layer 5a may be irradiated with ultraviolet rays in that state. You may irradiate an ultraviolet-ray from the 1st glass plate 11 side.
  • the method shown in FIG. 4 includes a step (a) of applying a photocurable resin composition to the surface of the first glass plate 11 and forming a photocurable resin layer 5a on the first glass plate 11.
  • the resin layer 5a is substantially completely cured through partial curing (also referred to as temporary curing) and subsequent further curing (main curing).
  • partial curing also referred to as temporary curing
  • main curing subsequent further curing
  • the resin layer (intermediate film) after the main curing does not have to be strictly cured completely, and a small amount of unreacted acrylic monomer may remain in the intermediate film. This also applies to the cured resin layers in FIGS.
  • a film material may be prepared and the resin layer 5a may be bonded to the surface of the glass plate.
  • an additional intermediate film and a glass plate (a third glass plate, etc.) are formed on the first glass plate side and / or the second glass plate side in the same manner as in FIGS. ) May be laminated.
  • a resin layer or an intermediate film may be formed on the first glass plate or the second plate, and a third glass plate may be bonded thereto. The same applies to the case of producing a laminated glass plate having four or more glass plates.
  • the laminated glass may be heated and pressurized. Bubbles in the laminate can be efficiently removed by heating and pressurizing the laminate.
  • an autoclave is used for heating and pressurization.
  • the heating temperature may be 30 to 150 ° C, or 50 to 70 ° C.
  • the pressure may be 0.3 to 1.5 MPa, or 0.3 to 0.5 MPa.
  • the heating and pressurization time may be 5 to 60 minutes, or 10 to 30 minutes. If the heating and pressurizing conditions are within these ranges, bubbles in the laminate can be removed particularly effectively.
  • Raw Material (A) Acrylic Polymer Synthetic Acrylic Polymer A-1 96.0 g of isostearyl acrylate (manufactured by Osaka Organic Chemical Co., Ltd., trade name “ISTA”) as an initial monomer was attached to a reaction vessel equipped with a cooling tube, a thermometer, a stirring device, a dropping funnel and a nitrogen introduction tube. 24.0 g of hydroxyethyl acrylate (manufactured by Osaka Organic Chemical Industry Co., Ltd., trade name “HEA”) and 150.0 g of methyl ethyl ketone were added. The reaction solution was heated from 25 ° C. to 80 ° C.
  • acrylic polymer A-1 (weight average molecular weight 120,000, Tg: -18 ° C.), which is a copolymer of isostearyl acrylate and 2-hydroxyethyl acrylate, was obtained.
  • EHA 2-ethylhexyl acrylate
  • Acrylic polymer A-3 96.0 g of isostearyl acrylate (manufactured by Osaka Organic Chemical Co., Ltd., trade name “ISTA”) as an initial monomer was attached to a reaction vessel equipped with a cooling tube, a thermometer, a stirring device, a dropping funnel and a nitrogen introduction tube. 24.0 g of hydroxyethyl acrylate (manufactured by Osaka Organic Chemical Industry Co., Ltd., trade name “HEA”) and 150.0 g of methyl ethyl ketone were added. Heating was performed from 25 ° C. to 80 ° C. for 15 minutes while purging nitrogen with an air flow of 100 ml / min.
  • Acrylic polymer A-4 In a reaction vessel equipped with a cooling tube, a thermometer, a stirrer, a dropping funnel and a nitrogen introduction tube, 120.0 g of lauryl acrylate as an initial monomer (manufactured by Kyoeisha Chemical Co., Ltd., trade name “Light Acrylate LA”), 150.0 g of methyl ethyl ketone was added. While the inside of the reaction vessel was purged with nitrogen at an air flow of 100 ml / min, it was heated from 25 ° C. to 80 ° C. for 15 minutes.
  • Acrylic polymer A-5 In a reaction vessel equipped with a cooling tube, a thermometer, a stirrer, a dropping funnel and a nitrogen introducing tube, 78.4 g of n-butyl acrylate (manufactured by Wako Pure Chemical Industries, Ltd.) as an initial monomer and 2-ethylhexyl acrylate 19. 6.0 g, 2.0 g of acrylic acid (manufactured by Wako Pure Chemical Industries, Ltd.) and 100.0 g of ultrapure water (manufactured by Wako Pure Chemical Industries, Ltd.) and 3.0 g of polyvinyl alcohol as a stabilizer were added. The reaction vessel was heated from 25 ° C. to 65 ° C.
  • acrylic polymer A-5 weight average molecular weight 2270000, Tg: ⁇ 18 ° C.
  • FA-512AS dicyclopentenyloxyethyl acrylate, manufactured by Hitachi Chemical Co., Ltd., trade name “FA-512AS”
  • FA-129AS nonanediol diacrylate, manufactured by Hitachi Chemical Co., Ltd., trade name “FA-129AS”
  • Weight average molecular weight (Mw) The weight average molecular weight of the acrylic polymer was determined by converting from a chromatogram obtained by gel permeation chromatography (GPC) using a standard polystyrene calibration curve. As a standard polystyrene for preparing a calibration curve, 5 sample sets (PStQuick MP-H, PStQuick B [trade name, manufactured by Tosoh Corporation]) were used. GPC was measured with the following apparatus and measurement conditions.
  • HLC-8320GPC High-speed GPC device HLC-8320GPC (detector: differential refractometer) (trade name, manufactured by Tosoh Corporation)
  • Solvent Tetrahydrofuran (THF) -Column: Column TSKGEL SuperMultipore HZ-H (trade name, manufactured by Tosoh Corporation)
  • Column size Column length is 15 cm and column inner diameter is 4.6 mm ⁇
  • Flow rate 0.35 mL / min ⁇
  • Sample concentration 10 mg / THF 5 mL
  • Injection volume 20 ⁇ L
  • Tg Glass transition temperature
  • the Tg of the acrylic polymer was determined by viscoelasticity measurement using a rheometer (manufactured by Anton Paar, MCR302). Measurement conditions and methods are shown below. Measurement conditions and rotor name: Parallel plate (PP12) ⁇ Frequency: 1 (s -1 ) ⁇ Strain amount: 1% Measuring method: The acrylic polymer formed to a thickness of 200 ⁇ m was attached to the metal stage of the rheometer. In this state, while heating the metal stage to 50 ° C., the acrylic polymer film was sandwiched between the metal stage and a parallel plate facing the metal stage. The distance between the metal stage and the parallel plate was set to 195 ⁇ m.
  • the metal plate was cooled to ⁇ 70 ° C., and then the viscoelasticity of the acrylic polymer was measured while increasing the temperature from ⁇ 70 ° C. to 50 ° C. at a temperature increase rate of 3 ° C./min.
  • the temperature at the maximum peak of tan ⁇ was recorded as the glass transition temperature (Tg).
  • the first glass plate / intermediate film / second glass plate laminate (laminated glass) is heated and pressurized in an autoclave under the conditions of a temperature of 50 ° C., a pressure of 0.5 MPa, and a holding time of 30 minutes.
  • a photocurable resin composition is apply
  • the thickness of the resin layer is adjusted so that the thickness of the cured intermediate film is 3.8 ⁇ 10 2 ⁇ m.
  • a light release separator is laminated on the resin layer.
  • the resin layer is photocured by irradiating the resin layer with ultraviolet rays (light quantity: 1.0 ⁇ 10 3 mJ / cm 2 ) using an ultraviolet irradiation device (manufactured by Eye Graphics Co., Ltd.) to form an intermediate film. .
  • the light release separator is peeled from the intermediate film, and a second glass plate is laminated on the exposed intermediate film using a vacuum laminator.
  • the first glass plate / intermediate film / second glass plate laminate (laminated glass) is heated and pressurized in an autoclave under the conditions of a temperature of 50 ° C., a pressure of 0.5 MPa, and a holding time of 30 minutes.
  • a photocurable resin composition is apply
  • the thickness of the resin layer is adjusted so that the thickness of the cured intermediate film is 3.8 ⁇ 10 2 ⁇ m.
  • the resin layer is temporarily cured by irradiating ultraviolet rays (light quantity: 3.0 ⁇ 10 2 mJ / cm 2 ) using an ultraviolet irradiation device (manufactured by Eye Graphics Co., Ltd.).
  • a second glass plate is laminated on the temporarily cured resin layer using a vacuum laminator. Thereafter, the resin layer is further photocured by irradiating the resin layer sandwiched between the first glass plate and the second glass with ultraviolet rays to form an intermediate film.
  • the first glass plate / intermediate film / second glass plate laminate (laminated glass) is heated and pressurized in an autoclave under the conditions of a temperature of 50 ° C., a pressure of 0.5 MPa, and a holding time of 30 minutes.
  • a photocurable resin composition is apply
  • a second glass plate is laminated on the formed resin layer using a vacuum laminator. The resin layer sandwiched between the first glass plate and the second glass plate is photocured by ultraviolet irradiation to form an intermediate film. Then, a photocurable resin composition is apply
  • a laminated body of the first glass plate / intermediate film / second glass plate / resin layer is laminated on the third glass plate with a vacuum laminator so that the resin layer faces inward.
  • the resin layer sandwiched between the second glass plate and the third glass plate is photocured by ultraviolet irradiation to form an intermediate film.
  • the autoclave of the first glass plate / intermediate film / second glass plate / intermediate film / third glass plate laminate is maintained at a temperature of 50 ° C., a pressure of 0.5 MPa, and a holding time of 30 minutes. Heat and pressurize inside.
  • the first glass plate and the second glass plate are bonded together while interposing the resin film for the intermediate film.
  • the obtained laminated body of the first glass plate / intermediate film / second glass plate is put in a rubber bag and deaerated at a vacuum degree of 2660 Pa for 20 minutes.
  • the laminate that has been degassed in the rubber bag and then transferred to the oven is pressed with a vacuum pressure while being held at 90 ° C. for 30 minutes.
  • the laminated body preliminarily pressure-bonded in this manner is pressure-bonded in an autoclave at 135 ° C. and a pressure of 118 N / cm 2 for 20 minutes to obtain a laminated glass.
  • Viscoelasticity of the interlayer film The viscoelasticity of the interlayer film of each laminated glass was measured using a dynamic viscoelasticity measuring instrument (TA Instruments Co., Ltd., product name “RSA-G2”) in the temperature range of ⁇ 70 to 100 ° C. The measurement was performed in the tensile measurement mode under conditions of a frequency of 0.05 Hz, 0.5 Hz, 5 Hz, or 50 Hz and a strain amount of 1%. From the measurement results, a master curve was created using TRIOS Software (TA Instruments Co., Ltd., product name) using the Arrhenius equation with a reference temperature of 25 ° C. From the obtained master curve, the storage elastic modulus at a frequency of 1000 Hz and the maximum value of the loss coefficient (tan ⁇ ) within a frequency range of 100 to 100,000 Hz were read.
  • a dynamic viscoelasticity measuring instrument (TA Instruments Co., Ltd., product name “RSA-G2”) in the temperature range of ⁇ 70 to 100 ° C. The measurement was performed in the
  • Example 1 60 parts by mass of acrylic polymer A-1, 30.9 parts by mass of isostearyl acrylate (ISTA), 9 parts by mass of 4-hydroxybutyl acrylate (4HBA), and 0.1 of 1-hydroxycyclohexyl phenyl ketone (I-184) The mass parts were mixed by stirring to obtain a liquid photocurable resin composition at 25 ° C. Using the obtained photocurable resin composition, a float glass plate (110 mm long, 110 mm wide, 2.7 mm thick) as the first glass plate, and a polycarbonate resin plate (PC plate, vertical) as the second glass plate 110 mm, width 110 mm, thickness 3.0 mm), and a laminated glass was produced by Method I.
  • I-184 1-hydroxycyclohexyl phenyl ketone
  • Example 2 60 parts by mass of acrylic polymer A-2, 30.9 parts by mass of ethylhexyl acrylate (EHA), 9 parts by mass of 4-hydroxybutyl acrylate (4HBA), and 0.1 part by mass of 1-hydroxycyclohexyl phenyl ketone (I-184) The parts were mixed by stirring to obtain a photocurable resin composition that was liquid at 25 ° C. Using the obtained photocurable resin composition, a float glass plate (110 mm long, 110 mm wide, 2.7 mm thick) as the first glass plate, and a polycarbonate resin plate (PC plate, vertical) as the second glass plate 110 mm, width 110 mm, and thickness 3.0 mm) were used to produce a laminated glass by Method II.
  • EHA ethylhexyl acrylate
  • 4HBA 4-hydroxybutyl acrylate
  • I-184 1-hydroxycyclohexyl phenyl ketone
  • Example 3 60 parts by mass of acrylic polymer A-1, 30.9 parts by mass of dicyclopentenyloxyethyl acrylate (FA-512AS), 9 parts by mass of 4-hydroxybutyl acrylate (4HBA), and 1-hydroxycyclohexyl phenyl ketone (I-184) 0.1 parts by mass was mixed by stirring to obtain a liquid photocurable resin composition at 25 ° C.
  • a float glass plate 110 mm long, 110 mm wide, 2.7 mm thick
  • a polycarbonate resin plate PC plate, vertical
  • Example 4 A laminated glass was produced in the same manner as in Example 1 except that a polymethyl methacrylate resin plate (PMMA plate, 110 mm long, 110 mm wide, 3.0 mm thick) was used as the second glass plate.
  • PMMA plate 110 mm long, 110 mm wide, 3.0 mm thick
  • Example 5 Tempered glass plate (110 mm long, 110 mm wide, thickness 0.55 mm) as the first glass plate, and polycarbonate resin plate (PC plate, 110 mm long, 110 mm wide, 5.0 mm thick) as the second glass plate A laminated glass was produced in the same manner as in Example 1 except that it was used.
  • Example 6 Using the same photocurable resin composition as in Example 1, a tempered glass plate (110 mm long, 110 mm wide, 0.55 mm thick) as the first glass plate and the third glass plate was used as the second glass plate.
  • a laminated glass was prepared by Method IV using a polycarbonate resin plate (PC plate, 110 mm long, 110 mm wide, 5.0 mm thick).
  • Comparative Example 2 A photocurable resin composition that is liquid at 25 ° C. by mixing 99.9 parts by mass of acrylic polymer A-1 and 0.1 parts by mass of 1-hydroxycyclohexyl phenyl ketone (I-184). Got. A laminated glass was produced in the same manner as in Example 1 except that the obtained photocurable resin composition was used.
  • Example 3 A laminated glass was produced in the same manner as in Example 1 except that the acrylic polymer A-3 was used in place of the acrylic polymer A-1.
  • Example 4 A laminated glass was produced in the same manner as in Example 1 except that the acrylic polymer A-4 was used in place of the acrylic polymer A-1.
  • Example 5 A laminated glass was produced in the same manner as in Example 1 except that a float glass plate (110 mm long, 110 mm wide, 2.7 mm thick) was used instead of the PC plate as the second glass plate.
  • a float glass plate 110 mm long, 110 mm wide, 2.7 mm thick
  • the light release separator is peeled from the film material for the interlayer film.
  • the exposed resin layer is affixed to float glass (length 110 mm, width 110 mm, thickness 2.7 mm) as a first glass plate, and in that state, a roller is pressed from the side of the heavy release separator to put the resin layer on the float glass. Adhere closely. Thereafter, the heavy release separator is released from the resin layer.
  • the exposed resin layer is attached to a float glass plate (110 mm long, 110 mm wide, 2.7 mm thick) as a second glass plate in a vacuum state using a vacuum laminator.
  • the obtained laminate is heated and pressurized in an autoclave under the conditions of a temperature of 50 ° C., a pressure of 0.5 MPa, and a 30-minute hold to obtain a laminated glass having a structure of float glass / intermediate film / float glass.
  • Comparative Example 7 Structure of float glass / intermediate film / PC as in Comparative Example 6 except that a PC plate (110 mm long, 110 mm wide, 3.0 mm thick) was used instead of the float glass plate as the second glass plate A laminated glass having was produced.
  • Acrylic polymer A-5 was dissolved in ethyl acetate to prepare an acrylic polymer solution having a concentration of 40% by mass.
  • Tolylene diisocyanate (Nikka Trading, trade name “TDI”) as a crosslinking agent was dissolved in ethyl acetate to prepare a crosslinking agent solution having a concentration of 25% by mass.
  • 100 parts by mass of the acrylic polymer solution and 2.0 parts by mass of the crosslinking agent solution were mixed and stirred.
  • the obtained mixed solution was formed on a polyethylene terephthalate film as a heavy release separator, and the coating film was dried to form a resin layer having a thickness of 3.8 ⁇ 10 2 ⁇ m.
  • a polyethylene terephthalate film as a light release separator was laminated on the formed resin layer to obtain an interlayer film material.
  • a laminated glass having a structure of float glass / intermediate film / float glass was obtained according to Method VI of Comparative Example 6 except that the obtained film material for interlayer film was used.
  • Comparative Example 9 A laminated glass was produced in the same manner as in Comparative Example 8, except that a PC plate (110 mm long, 110 mm wide, 3.0 mm thick) was used instead of the float glass plate as the second glass plate.
  • Comparative Example 11 A laminated glass was produced in the same manner as in Comparative Example 10 except that a PC plate (110 mm long, 110 mm wide, 3.0 mm thick) was used instead of the float glass plate as the second glass plate.
  • E mgH / A
  • E Impact strength [J / cm 2 ]
  • m Mass of hard sphere [kg]
  • g Gravitational acceleration
  • H Crack height [m]
  • A Laminated glass area [cm 2 ]
  • the impact strength of the laminated glass was measured for each of a test in which a hard sphere collides with the laminated glass from the first glass plate side and a test in which the rigid sphere collides with the laminated glass from the second glass plate or the third glass plate side. .
  • the laminated glasses prepared in the examples and comparative examples were fixed to a sample holder of an accelerated weather resistance tester (manufactured by Suga Test Instruments Co., Ltd., SX75), and a xenon long life arc lamp as a light source was 180 W / m 2.
  • the sample was subjected to an accelerated weathering test under the conditions of a temperature of 63 ° C., a humidity of 50% RH, and a test time of 300 hours while irradiating light with a wavelength of 300 to 400 nm.
  • the case where haze is 1.0 or less and bubbles are not visually confirmed is “Pass”, and the case where haze is 1.0 or more or occurrence of bubbles is visually confirmed is “NG”. did.
  • a frame-shaped spacer having a rectangular opening with a length of 80 mm and a width of 30 mm is arranged on a soda glass plate having dimensions of 100 mm in length and width, and the spacer is soda glass using Nystack (manufactured by Nichiban Co., Ltd.). Affixed to the board.
  • the photocurable resin composition was filled in the spacer frame without any gaps. From that, a polyester film (Toyobo Co., Ltd., trade name: Cosmo Shine A4300) larger than the spacer and having a length of 200 mm, a width of 100 mm, and a thickness of 125 ⁇ m was bonded.
  • the photocurable resin composition was exposed from above the polyester film with an illuminance of 100 mW and an exposure amount of 3.0 ⁇ 10 3 mJ / cm 2 using an exposure machine equipped with a high-power metal halide lamp.
  • the photocurable resin composition was cured by exposure to obtain a test sample in a state where the soda glass plate and the polyester film were bonded together by a cured product of the photocurable resin composition.
  • a notch having a length of 200 mm and a width of 10 mm was cut from the sample polyester film with a cutter.
  • the polyester film of the cut part was grasped, at 25 ° C., at a peeling angle of 180 °, and at a peeling speed of 60 mm / min.
  • the polyester film was peeled off from the cured product of the photocurable resin composition in the length direction of the sample. From the load at this time, peel strength (N / 10 mm) was determined.
  • the laminated glass of each example showed excellent impact strength with sufficiently low haze.
  • the laminated glass of each comparative example was not sufficient in terms of either haze or impact strength.
  • the laminated glass of each comparative example shown in Table 3 or Table 4 was not sufficient in terms of impact resistance and / or showed high haze, such as peeling in an impact resistance test.

Landscapes

  • Laminated Bodies (AREA)
  • Joining Of Glass To Other Materials (AREA)

Abstract

L'invention concerne un verre feuilleté comprenant : deux plaques de verre qui sont disposées de façon à se faire face ; et une couche intermédiaire qui est prise en sandwich entre les deux plaques de verre. Parmi les deux plaques de verre, l'une est une plaque en plastique transparent, et l'autre est une plaque en verre inorganique. La couche intermédiaire est formée du produit durci d'une composition de résine photodurcissable qui comprend un polymère acrylique (A), un monomère acrylique (B) et un initiateur de photopolymérisation (C). Ce verre feuilleté présente une résistance aux chocs au moins égale à 0,03 J/cm2comme mesuré par un test de résistance aux chocs dans lequel on laisse tomber une sphère indéformable sur le verre feuilleté.
PCT/JP2017/038931 2016-10-31 2017-10-27 Verre feuilleté et son procédé de production, et composition de résine photodurcissable pour couche intermédiaire pour verre feuilleté WO2018079720A1 (fr)

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PCT/JP2017/038931 WO2018079720A1 (fr) 2016-10-31 2017-10-27 Verre feuilleté et son procédé de production, et composition de résine photodurcissable pour couche intermédiaire pour verre feuilleté

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WO2020130116A1 (fr) * 2018-12-21 2020-06-25 積水化学工業株式会社 Couche intermédiaire pour verre feuilleté et verre feuilleté

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CN114072367B (zh) 2019-07-02 2023-09-22 积水化学工业株式会社 夹层玻璃用中间膜以及夹层玻璃

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JPH06206739A (ja) * 1993-01-13 1994-07-26 Nippon Shokubai Co Ltd 合わせ硝子製造用接着用樹脂
JPH07118038A (ja) * 1993-10-19 1995-05-09 Sekisui Chem Co Ltd 合わせガラス用中間膜
JP2001031451A (ja) * 1999-07-22 2001-02-06 Mitsubishi Plastics Ind Ltd 合わせガラス用中間膜及び合わせガラス
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WO2020130116A1 (fr) * 2018-12-21 2020-06-25 積水化学工業株式会社 Couche intermédiaire pour verre feuilleté et verre feuilleté
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JP7377200B2 (ja) 2018-12-21 2023-11-09 積水化学工業株式会社 合わせガラス用中間膜、及び合わせガラス

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