WO2023090456A1 - 接着性粒子及び積層体 - Google Patents

接着性粒子及び積層体 Download PDF

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Publication number
WO2023090456A1
WO2023090456A1 PCT/JP2022/043162 JP2022043162W WO2023090456A1 WO 2023090456 A1 WO2023090456 A1 WO 2023090456A1 JP 2022043162 W JP2022043162 W JP 2022043162W WO 2023090456 A1 WO2023090456 A1 WO 2023090456A1
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WIPO (PCT)
Prior art keywords
group
particles
substrate
adhesive particles
laminate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2022/043162
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English (en)
French (fr)
Japanese (ja)
Inventor
滉生 大倉
恭幸 山田
武司 脇屋
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sekisui Chemical Co Ltd
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Sekisui Chemical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sekisui Chemical Co Ltd filed Critical Sekisui Chemical Co Ltd
Priority to KR1020247016033A priority Critical patent/KR20240115817A/ko
Priority to JP2022573498A priority patent/JPWO2023090456A1/ja
Priority to US18/711,722 priority patent/US20250011629A1/en
Priority to CN202280071315.8A priority patent/CN118159902A/zh
Priority to EP22895737.9A priority patent/EP4439161A4/en
Publication of WO2023090456A1 publication Critical patent/WO2023090456A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/08—Macromolecular additives
    • 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
    • B32B1/00—Layered products having a non-planar shape
    • 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
    • B32B17/10005—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 laminated safety glass or glazing
    • B32B17/10009—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 laminated safety glass or glazing characterized by the number, the constitution or treatment of glass sheets
    • B32B17/10036—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 laminated safety glass or glazing characterized by the number, the constitution or treatment of glass sheets comprising two outer glass sheets
    • 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
    • B32B17/10005—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 laminated safety glass or glazing
    • B32B17/10165—Functional features of the laminated safety glass or glazing
    • B32B17/10431—Specific parts for the modulation of light incorporated into the laminated safety glass or glazing
    • B32B17/10467—Variable transmission
    • B32B17/10495—Variable transmission optoelectronic, i.e. optical valve
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    • B32B17/1055—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 laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
    • B32B17/10614—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 laminated safety glass or glazing characterized by the resin layer, i.e. interlayer comprising particles for purposes other than dyeing
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
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    • B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/12—Powdering or granulating
    • C08J3/126—Polymer particles coated by polymer, e.g. core shell structures
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
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    • 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
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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    • C08J2333/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
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    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C—CHEMISTRY; METALLURGY
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Definitions

  • the present invention relates to adhesive particles and laminates using the adhesive particles.
  • Light control materials such as light control glass and light control film are sometimes used in display devices such as liquid crystal display devices and in-vehicle displays.
  • the light modulating material is a material that has the property that the light transmittance changes depending on whether or not an electric field is applied, and the amount of incident light can be adjusted.
  • the light modulating material uses particles as spacers to control the gap between the substrates.
  • an adhesive may be used to bond two sheets of glass or film substrates together.
  • the liquid crystal display element is constructed by arranging liquid crystal between two glass or film substrates.
  • particles are used as spacers in order to control the gap between the substrates.
  • an adhesive is sometimes used to bond two sheets of glass or film substrates together.
  • Patent Document 1 discloses a particle comprising a substrate particle and a coating portion disposed on the surface of the substrate particle.
  • the material of the coating portion is a compound having a specific structure.
  • Patent Literature 1 describes a thermoplastic resin as a material for the covering portion.
  • An object of the present invention is to provide adhesive particles that can sufficiently improve adhesiveness. Another object of the present invention is to provide a laminate using the adhesive particles.
  • a broad aspect of the present invention provides adhesive particles containing a compound having a structure represented by the following formula (1).
  • R1 and R2 each represent an organic group having an amino group, an organic group having an epoxy group, an organic group having an amide group, an organic group having an isocyanate group, or an organic group having a hydroxy group.
  • R3 represents an alkyl group having 1 to 2 carbon atoms, an alkoxy group having 1 to 2 carbon atoms, or a vinyl group; p is 1 or 1.5; when p is 1, q is 1, and R4 represents a hydrogen atom, an alkyl group having 1 to 2 carbon atoms, an alkoxy group having 1 to 2 carbon atoms, or a vinyl group; when p is 1.5, q is 0; ; n represents an integer from 1 to 100;
  • the 10% K value at 25°C is 100 N/mm 2 or more and 1500 N/mm 2 or less.
  • the 10% K value at 25°C after heating the adhesive particles at 120°C for 1 hour is 100 N/mm 2 or more and 1800 N/mm 2 or less.
  • the compression recovery rate at 25°C is 0.1% or more and 30% or less.
  • the adhesive particle comprises a substrate particle and a coating portion arranged on the surface of the substrate particle.
  • an exothermic peak is observed in differential scanning calorimetry in which the adhesive particles are heated from 100° C. to 150° C. in an air atmosphere at a heating rate of 5° C./min. be done.
  • a broad aspect of the invention comprising a first substrate, a second substrate, spacer particles disposed between said first substrate and said second substrate, A laminate is provided, wherein the spacer particles are adhered to the first substrate and the second substrate, and the material of the spacer particles comprises the adhesive particles described above.
  • a broad aspect of the invention comprising a first substrate, a second substrate, spacer particles disposed between said first substrate and said second substrate, The spacer particles are bonded to the first base material and the second base material, and the spacer particles contain a compound having a structural unit represented by the following formula (11): provided.
  • R3 represents an alkyl group having 1 to 2 carbon atoms, an alkoxy group having 1 to 2 carbon atoms, or a vinyl group
  • p is 1 or 1.5
  • R4 represents a hydrogen atom, an alkyl group having 1 to 2 carbon atoms, an alkoxy group having 1 to 2 carbon atoms, or a vinyl group
  • p is 1.5
  • q is 0
  • n represents an integer from 1 to 100.
  • the laminate has a curved surface portion.
  • the laminate is a light control laminate, and the light control layer is arranged between the first base material and the second base material. further provide.
  • the adhesive particles according to the present invention contain a compound having a structure represented by formula (1) above. Since the adhesive particles according to the present invention have the above configuration, the adhesiveness can be sufficiently enhanced.
  • FIG. 1 is a cross-sectional view schematically showing adhesive particles according to a first embodiment of the present invention.
  • FIG. 2 is a cross-sectional view schematically showing adhesive particles according to a second embodiment of the present invention.
  • FIG. 3 is a cross-sectional view schematically showing a laminate using adhesive particles according to the first embodiment of the present invention.
  • FIG. 4 is a cross-sectional view schematically showing a PDLC-type light control laminate using adhesive particles according to the first embodiment of the present invention.
  • FIG. 5 is a cross-sectional view schematically showing an SPD-type light control laminate using adhesive particles according to the first embodiment of the present invention.
  • (meth)acrylate means one or both of “acrylate” and “methacrylate”
  • (meth)acryl means one or both of "acrylic” and “methacrylic”. means both.
  • the adhesive particles according to the present invention contain a compound having a structure represented by formula (1) below.
  • R1 and R2 each represent an organic group having an amino group, an organic group having an epoxy group, an organic group having an amide group, an organic group having an isocyanate group, or an organic group having a hydroxy group.
  • R3 represents an alkyl group having 1 to 2 carbon atoms, an alkoxy group having 1 to 2 carbon atoms, or a vinyl group.
  • p is 1 or 1.5.
  • R4 represents a hydrogen atom, an alkyl group having 1 or 2 carbon atoms, an alkoxy group having 1 or 2 carbon atoms, or a vinyl group.
  • p is 1.5
  • q is 0 (R4 is absent).
  • n represents an integer from 1 to 100;
  • the adhesive particles according to the present invention have the above configuration, the adhesiveness of the adhesive particles can be sufficiently enhanced. As a result, when the adhesive particles are used as a material for the spacer particles, the separation of the spacer particles from the base material can be suppressed, so that the gap between the base materials can be controlled with high accuracy. Moreover, since the adhesive particles according to the present invention have the above configuration, it is possible to prevent the substrate from being scratched. Furthermore, since the adhesive particles according to the present invention have the above configuration, peeling of the base material can be suppressed when the particles are used in the light control laminate.
  • the adhesive particles according to the present invention are provided with the above configuration, for example, even if the laminate has a curved surface portion, the adhesive particles do not move on the curved surface portion, and the base material The uniformity of the gap between them can be ensured.
  • the adhesive particles according to the present invention can suppress the peeling of the adhesive particles from the substrate even if the laminate has a curved surface portion, so that the uniformity of the gap between the substrates can be ensured. can do. As a result, it is possible to suppress the occurrence of problems such as color unevenness in the liquid crystal display device caused by non-uniformity of the gap.
  • a spherical shape is not limited to a true spherical shape, but includes a substantially spherical shape, and includes, for example, a shape having an aspect ratio (major axis/minor axis) of 1.5 or less.
  • FIG. 1 is a cross-sectional view schematically showing adhesive particles according to the first embodiment of the present invention.
  • the adhesive particles 1 contain a compound having a structure represented by formula (1) above.
  • FIG. 2 is a cross-sectional view schematically showing adhesive particles according to the second embodiment of the present invention.
  • the adhesive particle 1A includes a base particle 11A and a covering portion 12A arranged on the surface of the base particle 11A.
  • the covering portion 12A covers the surfaces of the substrate particles 11A.
  • the adhesive particles 1A are coated particles in which the surfaces of the substrate particles 11A are coated with the coating portions 12A.
  • the covering portion may completely cover the surface of the base particle, or may not completely cover the surface of the base particle.
  • the substrate particles may have portions not covered with the covering portion.
  • the adhesive particles 1A contain a compound having a structure represented by formula (1) above.
  • the substrate particles may contain a compound having a structure represented by the above formula (1)
  • the coating portion may contain a compound having a structure represented by the above formula (1). good too. From the viewpoint of exhibiting the effect of the present invention more effectively, it is preferable that the covering portion contains a compound having a structure represented by the above formula (1).
  • the above formula (1) is represented by the following formula (1A) when p is 1.
  • R1 and R2 each represent an organic group having an amino group, an organic group having an epoxy group, an organic group having an amide group, an organic group having an isocyanate group, or an organic group having a hydroxy group.
  • R3 represents an alkyl group having 1 to 2 carbon atoms, an alkoxy group having 1 to 2 carbon atoms, or a vinyl group.
  • R4 represents a hydrogen atom, an alkyl group having 1 to 2 carbon atoms, an alkoxy group having 1 to 2 carbon atoms, or a vinyl group.
  • n represents an integer from 1 to 100;
  • the above formula (1) is represented by the following formula (1B) when p is 1.5.
  • R1 and R2 each represent an organic group having an amino group, an organic group having an epoxy group, an organic group having an amide group, an organic group having an isocyanate group, or an organic group having a hydroxy group.
  • R3 represents an alkyl group having 1 to 2 carbon atoms, an alkoxy group having 1 to 2 carbon atoms, or a vinyl group.
  • n represents an integer from 1 to 100;
  • a compound having a structure represented by the above formula (1B) is generally called a polysilsesquioxane.
  • q in the above formula (1) is 0 and R4 does not exist.
  • R1 and R2 are each an organic group having an amino group, an organic group having an epoxy group, an organic group having an amide group, an organic group having an isocyanate group, or represents an organic group having a hydroxy group.
  • R1 and R2 may be the same or different.
  • R1 and R2 are each preferably an organic group having an amino group or an organic group having an epoxy group. .
  • R3 represents an alkyl group having 1 to 2 carbon atoms, an alkoxy group having 1 to 2 carbon atoms, or a vinyl group. From the viewpoint of further improving the adhesiveness, in the above formulas (1), (1A) and (1B), R3 is preferably a methyl group, an ethyl group or a vinyl group, more preferably a methyl group. .
  • R4 represents a hydrogen atom, an alkyl group having 1 to 2 carbon atoms, an alkoxy group having 1 to 2 carbon atoms, or a vinyl group. From the viewpoint of further enhancing adhesiveness, in the above formulas (1) and (1A), R4 is preferably a methyl group, an ethyl group or a vinyl group, more preferably a methyl group.
  • n represents an integer of 1-100. From the viewpoint of further increasing the adhesiveness, in the above formulas (1), (1A) and (1B), n is preferably an integer of 2 or more, preferably an integer of 50 or less, more preferably an integer of 10 or less is.
  • R3 and R4 may be the same or different.
  • a plurality of R3 may be the same or different.
  • a plurality of R4 may be the same or different.
  • the compound having the structure represented by the above formula (1) may include the compound having the structure represented by the above formula (1A), and the compound having the structure represented by the above formula (1B). It may contain a compound having a structure represented by the above formula (1A) and a compound having a structure represented by the above formula (1B).
  • the compound having the structure represented by formula (1) may include the compound having the structure represented by formula (1A) and the compound having the structure represented by formula (1B).
  • the compound having the structure represented by the formula (1) may be a compound having the structure represented by the formula (1A) and the structure represented by the formula (1B).
  • the structure represented by the above formula (1) may be the structure represented by the above formula (1A) or the structure represented by the above formula (1B).
  • the compound having the structure represented by formula (1) above preferably contains the compound having the structure represented by formula (1A) above.
  • the structure represented by the above formula (1) is preferably the structure represented by the above formula (1A).
  • the content of the compound having the structure represented by the formula (1) in 100% by weight of the adhesive particles is preferably 1% by weight or more, more preferably 5% by weight or more, and still more preferably 10% by weight or more. Yes, preferably 50% by weight or less, more preferably 40% by weight or less, and even more preferably 30% by weight or less.
  • the adhesiveness is further enhanced, and the 10% K value at 25 ° C. of the adhesive particles is suitable.
  • the range can be easily controlled.
  • the compound having the structure represented by the formula (1) includes both the compound having the structure represented by the formula (1A) and the compound having the structure represented by the formula (1B). be.
  • the above content represents the sum of the content of the compound having the structure represented by formula (1A) and the content of the compound having the structure represented by formula (1B).
  • the tensile yield stress of the adhesive particles is preferably 0.07 MPa or more, more preferably 0.10 MPa or more, and still more preferably 0.12 MPa or more. is preferred.
  • the upper limit of the tensile yield stress of the adhesive particles is not particularly limited. In the following adhesion test A, the tensile yield stress of the adhesive particles may be 0.12 MPa or less, or 0.07 MPa or less.
  • Adhesion test A Glass substrates are prepared as the first base material and the second base material. 14000 particles/mm 2 of adhesive particles are scattered on the surface of the first substrate. A second substrate is then placed over the adhesive particles. The adhesive particles are adhered to the first and second substrates by heating at 120° C. for 1 hour under a pressure of 5 kgf/cm 2 in accordance with the method of JIS K6850 to prepare a specimen (test sample). Using a Tensilon universal material testing machine (for example, "RTI-1310" manufactured by A&D Co., Ltd.), the adhesive strength of the specimen obtained at a tensile speed of 20 mm / min and a load cell rating of 1000 N is measured at 23 ° C. . This measured value is taken as the tensile yield stress of the adhesive particles.
  • RTI-1310 manufactured by A&D Co., Ltd.
  • the 90° peel strength of the adhesive particles is preferably 0.1 N/30 mm or more, more preferably 0.5 N/30 mm or more, and still more preferably is preferably 1.0 N/30 mm or more.
  • the upper limit of the 90° peel strength of the adhesive particles is not particularly limited.
  • the adhesive particles may have a 90° peel strength of 10.0 N/30 mm or less, or 0.1 N/30 mm or less.
  • films with alignment films are prepared by casting a polyimide solution on a PET film, drying, and rubbing. 14000 particles/mm 2 of adhesive particles are scattered on the surface of the first substrate. A second substrate is then placed over the adhesive particles. The adhesive particles are adhered to the first and second substrates by heating at 120° C. for 1 hour under a pressure of 5 kgf/cm 2 in accordance with the method of JIS K6850 to prepare a specimen (test sample).
  • the measurement is performed using a tensile tester (for example, "Autograph AGS” manufactured by Shimadzu Corporation) at a tensile speed of 50 mm/sec. This measured value is taken as the 90° peel strength of the adhesive particles.
  • a tensile tester for example, "Autograph AGS” manufactured by Shimadzu Corporation
  • the 10% K value at 25° C. of the adhesive particles is preferably 100 N/mm 2 or more, more preferably 200 N/mm 2 or more, still more preferably 300 N/mm 2 or more, and preferably 1500 N/mm 2 or less. , more preferably 1000 N/mm 2 or less, still more preferably 800 N/mm 2 or less.
  • the 10% K value at 25°C of the adhesive particles is equal to or higher than the lower limit and equal to or lower than the upper limit, the adhesiveness of the adhesive particles can be further enhanced. As a result, it is possible to suppress the separation of the adhesive particles from the base material, so that when the adhesive particles are used as the material of the spacer particles, the gap between the base materials can be controlled with high accuracy. . Also, the substrate can be prevented from being damaged.
  • the 10% K value at 25°C of the adhesive particles can be measured as follows. Using a microcompression tester, the adhesive particles are compressed at 25° C. with a smooth indenter end face of a cylinder (50 ⁇ m in diameter, made of diamond) under conditions of applying a maximum test load of 20 mN for 60 seconds. The load value (N) and compression displacement (mm) at this time are measured. From the measured values obtained, the 10% K value at 25° C. can be obtained by the following formula. As the microcompression tester, for example, "Fischer Scope H-100" manufactured by Fisher Co., Ltd. is used.
  • Methods for controlling the 10% K value at 25° C. of the adhesive particles within a suitable range include a method of adjusting the content of the compound having the structure represented by the above formula (1), and a resin and Examples include a method of adjusting the type and content of the curing agent.
  • the 10% K value at 25° C. after heating the adhesive particles at 120° C. for 1 hour is preferably 100 N/mm 2 or more, more preferably 200 N/mm 2 or more, and still more preferably 300 N/mm 2 or more. Yes, preferably 1800 N/mm 2 or less, more preferably 1700 N/mm 2 or less, and even more preferably 1500 N/mm 2 or less.
  • the 10% K value at 25°C after heating the adhesive particles at 120°C for 1 hour is equal to or higher than the lower limit and equal to or lower than the upper limit, the adhesiveness of the adhesive particles can be further enhanced.
  • the spacer particles can disperse the stress applied to the base material, so that peeling of the base material can be further suppressed. Also, the substrate can be prevented from being damaged.
  • the 10% K value at 25°C after heating the adhesive particles at 120°C for 1 hour (10% K value at 25°C after heating) can be measured as follows.
  • the adhesive particles are heated at 120° C. for 1 hour in a blower constant temperature thermostat (for example, “DKN302” manufactured by Yamato Scientific Co., Ltd.).
  • a microcompression tester the adhesive particles after heating are compressed at 25° C. with a smooth indenter end face of a cylinder (50 ⁇ m in diameter, made of diamond) under conditions of applying a maximum test load of 20 mN for 60 seconds.
  • the load value (N) and compression displacement (mm) at this time are measured. From the measured values obtained, the 10% K value at 25° C. after heating can be obtained by the following formula.
  • the microcompression tester for example, "Fischer Scope H-100" manufactured by Fisher Co., Ltd. is used.
  • the content of the compound having the structure represented by the above formula (1) is A method of adjusting, a method of adjusting the type and content of the resin and the curing agent, which will be described later, and the like.
  • the compression recovery rate of the adhesive particles at 25°C is preferably 0.1% or more, more preferably 1.0% or more, and preferably 30% or less, more preferably 20% or less.
  • the compression recovery rate at 25° C. of the adhesive particles is equal to or higher than the lower limit and equal to or lower than the upper limit, the adhesiveness of the adhesive particles can be further enhanced.
  • the adhesive particles are used as a material for the spacer particles, the separation of the spacer particles from the base material can be suppressed, so that the gap between the base materials can be controlled with high accuracy.
  • peeling of the base material can be further suppressed when used in the light control laminate. .
  • the compression recovery rate of the adhesive particles at 25°C can be measured as follows.
  • a single adhesive particle that has been dispersed is subjected to a smooth indenter end face of a cylinder (50 ⁇ m in diameter, made of diamond) at 25° C. toward the center of the adhesive particle at an origin load value of 1.5°C.
  • a compression recovery rate is derived by applying a load under the conditions of 0 mN and a reverse load value of 10 mN and analyzing the recovery behavior after the load is removed. By measuring the load-compression displacement during this period, the compression recovery rate can be obtained from the following formula. Note that the load speed is 0.33 mN/sec.
  • the microcompression tester for example, "Fischer Scope H-100" manufactured by Fisher Co., Ltd. is used.
  • Compression recovery rate (%) [L2/L1] x 100
  • L1 Compressive displacement from the origin load value to the reverse load value when the load is applied
  • L2 Unloading displacement from the reverse load value to the origin load value when releasing the load
  • the average particle size of the adhesive particles is preferably 1 ⁇ m or more, more preferably 3 ⁇ m or more, still more preferably 10 ⁇ m or more, and preferably 150 ⁇ m or less, more preferably 100 ⁇ m or less. More preferably, it is 50 ⁇ m or less.
  • the particle diameter of the adhesive particles means the diameter when the adhesive particles are spherical, and when the adhesive particles have a shape other than a spherical shape, it is assumed to be a true sphere corresponding to the volume. means the diameter when The particle size of the adhesive particles is preferably an average particle size, more preferably a number average particle size.
  • the particle size of the adhesive particles can be measured by any particle size distribution analyzer. For example, it can be measured using a particle size distribution measuring apparatus using the principle of laser light scattering, electrical resistance value change, image analysis after imaging, or the like.
  • a particle size distribution measuring device (“Multisizer 4" manufactured by Beckman Coulter) is used to measure the particle size of about 100,000 adhesive particles, and the average value is A method of calculating is exemplified.
  • the CV value of the particle diameter of the adhesive particles is preferably 10% or less, more preferably 7% or less.
  • the smaller the CV value of the particle diameter of the adhesive particles the better.
  • the CV value of the particle diameter of the adhesive particles is equal to or less than the above upper limit. is performed, the adhesive particles can follow the laminate, and movement of the adhesive particles can be suppressed.
  • the lower limit of the CV value of the particle diameter of the adhesive particles is not particularly limited.
  • the CV value of the particle diameter of the adhesive particles may be 0% or more, or 7% or more.
  • the CV value (variation coefficient) of the particle size of the adhesive particles can be measured as follows.
  • CV value (%) ( ⁇ /Dn) ⁇ 100 ⁇ : standard deviation of the particle size of the adhesive particles Dn: average value of the particle size of the adhesive particles
  • the aspect ratio of the adhesive particles is preferably 1.5 or less, more preferably 1.3 or less.
  • the above aspect ratio indicates major axis/minor axis.
  • the aspect ratio is obtained by observing 10 arbitrary adhesive particles with an electron microscope or an optical microscope, defining the maximum diameter and the minimum diameter as the major diameter and the minor diameter, respectively, and averaging the major diameter / minor diameter of each spherical adhesive particle. It is preferable to obtain by calculating the value.
  • the lower limit of the aspect ratio of the adhesive particles is not particularly limited.
  • the aspect ratio of the adhesive particles may be 1.0 or more, or 1.1 or more.
  • an exothermic peak is preferably observed in differential scanning calorimetry in which the adhesive particles are heated from 100°C to 150°C in an air atmosphere at a heating rate of 5°C/min.
  • the exothermic peak means a peak with a calorific value of 50000 mJ/mg or more.
  • the differential scanning calorimetry may be performed under atmospheric conditions or under conditions other than atmospheric conditions (for example, nitrogen atmosphere).
  • 10 mg of the adhesive particles are preferably heated from 100° C. to 150° C. at a rate of temperature increase of 5° C./min under an air atmosphere.
  • a differential scanning calorimeter (“EXSTAR DSC7020” manufactured by SII) or the like is used for the differential scanning calorimetry.
  • the adhesive particles according to the present invention are suitably used as materials for spacer particles.
  • the adhesive particles according to the present invention are particularly suitable for use as a material for spacer particles in a light control laminate.
  • the adhesive particles may be used as a material for spacer particles for a light control glass, or may be used as a material for spacer particles for a light control film.
  • the adhesive particles are preferably used as a material for spacer particles for light control glass or a material for spacer particles for light control film.
  • the adhesive particles preferably contain a resin.
  • the above resins include polyolefin resins such as polyethylene, polypropylene, polystyrene, polyvinyl chloride, polyvinylidene chloride, polyisobutylene, and polybutadiene; acrylic resins such as polymethyl methacrylate and polymethyl acrylate; polycarbonates, polyamides, phenol formaldehyde resins; Melamine formaldehyde resin, benzoguanamine formaldehyde resin, urea formaldehyde resin, phenol resin, melamine resin, benzoguanamine resin, urea resin, epoxy resin, unsaturated polyester resin, saturated polyester resin, polyethylene terephthalate, polysulfone, polyphenylene oxide, polyacetal, polyimide, polyamideimide , polyetheretherketone, polyethersulfone, and divinylbenzene polymers.
  • the divinylbenzene polymer may be a divinylbenzene copolymer.
  • examples of the divinylbenzene copolymer and the like include a divinylbenzene-styrene copolymer and a divinylbenzene-(meth)acrylate copolymer.
  • the resin is preferably a thermosetting resin, more preferably an epoxy resin.
  • the epoxy resin is preferably a polyfunctional epoxy resin.
  • the polyfunctional epoxy resin may be a bifunctional epoxy resin, a bifunctional or higher functional epoxy resin, a trifunctional epoxy resin, or a trifunctional or higher functional epoxy resin. , a tetrafunctional epoxy resin, or a tetrafunctional or higher epoxy resin.
  • Bifunctional epoxy resins include bisphenol A type epoxy resins and bisphenol F type epoxy resins.
  • the trifunctional epoxy resins include triazine-type epoxy resins and glycidylamine-type epoxy resins.
  • Examples of the tetrafunctional epoxy resins include tetrakisphenolethane type epoxy resins and glycidylamine type epoxy resins. Only one type of the epoxy resin may be used, or two or more types may be used in combination.
  • the above resin is preferably used in combination with a curing agent.
  • the curing agent cures the resin.
  • the curing agent is not particularly limited.
  • the curing agent is preferably a thermosetting agent.
  • Examples of the curing agent include imidazole curing agents, amine curing agents, phenol curing agents, thiol curing agents, and acid anhydride curing agents. Only one kind of the curing agent may be used, or two or more kinds thereof may be used in combination. From the viewpoint of easily controlling the compression properties of the adhesive particles within a suitable range, the curing agent is preferably an amine curing agent.
  • the imidazole curing agent is not particularly limited.
  • Examples of the imidazole curing agent include 2-methylimidazole, 2-ethyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-phenylimidazolium trimellitate, 2,4-diamino-6.
  • the thiol curing agent is not particularly limited.
  • the thiol curing agent may be a polythiol curing agent.
  • Examples of the thiol curing agent include trimethylolpropane tris-3-mercaptopropionate, pentaerythritol tetrakis-3-mercaptopropionate, and dipentaerythritol hexa-3-mercaptopropionate.
  • the above amine curing agent is not particularly limited.
  • examples of the amine curing agent include ethylenediamine, hexamethylenediamine, octamethylenediamine, decamethylenediamine, norbornanediamine, 3,9-bis(3-aminopropyl)-2,4,8,10-tetraspiro[5.5].
  • undecane bis(4-aminocyclohexyl)methane, phenylenediamine, 2,2-bis[4-(4-aminophenoxy)phenyl]propane, metaphenylenediamine, diaminodiphenylmethane, diaminophenyl ether, metaxylenediamine, diaminonaphthalene, bisaminomethylcyclohexane, diaminodiphenylsulfone, and the like.
  • the amine curing agent is ethylenediamine, hexamethylenediamine, octamethylenediamine, metaphenylenediamine, norbornanediamine, diaminodiphenylmethane, diaminodiphenylsulfone, phenylenediamine, or 2,2-bis[4-(4-aminophenoxy)phenyl].
  • Propane is preferred.
  • the amine curing agent is the preferred compound described above, the compression properties of the adhesive particles can be easily controlled within a suitable range.
  • the amine curing agent may be ethylenediamine, norbornanediamine, phenylenediamine, or 2,2-bis[4-(4-aminophenoxy)phenyl ] Propane is more preferred, and norbornanediamine is even more preferred.
  • the acid anhydride curing agent is not particularly limited.
  • As the acid anhydride curing agent a wide range of acid anhydrides commonly used as curing agents for thermosetting resins such as epoxy resins can be used.
  • Examples of the acid anhydride curing agent include phthalic anhydride, tetrahydrophthalic anhydride, trialkyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, and methylbutenyltetrahydrophthalic anhydride.
  • anhydrides of phthalic acid derivatives maleic anhydride, nadic anhydride, methyl nadic anhydride, glutaric anhydride, succinic anhydride, glycerin bis trimellitic anhydride monoacetate, and ethylene glycol bis trimellitic anhydride.
  • acid anhydride curing agent trifunctional acid anhydride curing agent such as trimellitic anhydride, and pyromellitic anhydride, benzophenone tetracarboxylic anhydride, methylcyclohexene tetracarboxylic anhydride, polyazelaic anhydride, etc. and a tetrafunctional or higher acid anhydride curing agent.
  • the polymerization method is not particularly limited, and known methods such as radical polymerization, ionic polymerization, polycondensation (condensation polymerization, polycondensation), addition condensation, living polymerization, and living radical polymerization. Polymerization can be carried out by
  • the above adhesive particles can be easily obtained by performing dispersion polymerization or the like using a material containing a polyfunctional epoxy resin and a curing agent in a solution.
  • a method of suspension polymerization using a solution in which a polyfunctional epoxy resin and a curing agent are dissolved as an oil layer and a method of polymerizing by swelling a solution in which a polyfunctional epoxy resin and a curing agent are dissolved using non-crosslinked seed particles. It can be obtained by a method such as a seed polymerization method.
  • the adhesive particles may contain other components as necessary.
  • the other components include coloring agents, polymerization initiators, polymerization inhibitors, adhesion imparting agents, anti-coloring agents, surfactants, polymer dispersants, and the like. Only one of the other components may be used, or two or more thereof may be used in combination.
  • a laminate according to the present invention (hereinafter sometimes referred to as a laminate (A)) includes a first base material, a second base material, and the first base material and the second base material. and spacer particles disposed between.
  • the spacer particles adhere to the first base material and the second base material.
  • the material of the spacer particles contains the adhesive particles.
  • the spacer particles can be formed in the laminate (A) by thermosetting the thermosetting resin or by reacting the compound having the structure represented by the formula (1). can. Further, the spacer particles can be formed between the first base material and the second base material by heat-curing the thermosetting resin or reacting the compound having the structure represented by the formula (1). It can be adhered to materials.
  • a laminate (B) includes a first base material, a second base material, and the first base material and the second base material.
  • the spacer particles contain a compound having a structural unit represented by the following formula (11).
  • the spacer particles can be formed in the laminate (B) by thermosetting the thermosetting resin or reacting the compound having the structure represented by the formula (1). can.
  • the spacer particles can be formed between the first base material and the second base material by heat-curing the thermosetting resin or reacting the compound having the structure represented by the formula (1). It can be adhered to materials.
  • R3 represents an alkyl group having 1 to 2 carbon atoms, an alkoxy group having 1 to 2 carbon atoms, or a vinyl group.
  • p is 1 or 1.5.
  • R4 represents a hydrogen atom, an alkyl group having 1 or 2 carbon atoms, an alkoxy group having 1 or 2 carbon atoms, or a vinyl group.
  • p is 1.5, q is 0 (R4 is absent).
  • n represents an integer from 1 to 100;
  • the adhesiveness can be sufficiently improved, and the gap between the substrates can be controlled with high precision. can.
  • the layered product (A) and the layered product (B) according to the present invention are provided with the above configuration, it is possible to prevent the substrate from being scratched.
  • the layered product (A) and the layered product (B) according to the present invention have the above-described configuration, so that peeling of the base material can be suppressed when used in the light control layered product. .
  • the layered product (A) and the layered product (B) according to the present invention are provided with the above-described configuration, for example, even if the layered product has a curved surface portion, the spacer particles are formed in the curved surface portion. Gap uniformity between substrates can be ensured without movement. Moreover, even if the laminate has a curved surface portion, separation of the spacer particles from the base material can be suppressed, so that the uniformity of the gap between the base materials can be ensured. As a result, it is possible to suppress the occurrence of problems such as color unevenness in the liquid crystal display device caused by non-uniformity of the gap.
  • R3 represents an alkyl group having 1 to 2 carbon atoms, an alkoxy group having 1 to 2 carbon atoms, or a vinyl group.
  • R4 represents a hydrogen atom, an alkyl group having 1 to 2 carbon atoms, an alkoxy group having 1 to 2 carbon atoms, or a vinyl group.
  • n represents an integer from 1 to 100;
  • R3 represents an alkyl group having 1 to 2 carbon atoms, an alkoxy group having 1 to 2 carbon atoms, or a vinyl group.
  • n represents an integer from 1 to 100;
  • a compound having a structural unit represented by the above formula (11B) is generally called a polysilsesquioxane.
  • q in the above formula (11) is 0 and R4 does not exist.
  • R3 represents an alkyl group having 1 to 2 carbon atoms, an alkoxy group having 1 to 2 carbon atoms, or a vinyl group. From the viewpoint of further improving adhesiveness, in the above formulas (11), (11A) and (11B), R3 is preferably a methyl group, an ethyl group or a vinyl group, more preferably a methyl group. .
  • R4 represents a hydrogen atom, an alkyl group having 1 to 2 carbon atoms, an alkoxy group having 1 to 2 carbon atoms, or a vinyl group. From the viewpoint of further enhancing adhesiveness, R4 in the above formulas (11) and (11A) is preferably a methyl group, an ethyl group or a vinyl group, more preferably a methyl group.
  • n represents an integer of 1-100. From the viewpoint of further increasing the adhesiveness, in the above formulas (11), (11A) and (11B), n is preferably an integer of 2 or more, preferably an integer of 50 or less, more preferably an integer of 10 or less is.
  • R3 and R4 may be the same or different.
  • a plurality of R3 when n is 2 or more, a plurality of R3 may be the same or different.
  • a plurality of R4 when n is 2 or more, a plurality of R4 may be the same or different.
  • the compound having a structural unit represented by the formula (11) may contain a compound having a structural unit represented by the formula (11A), and has a structural unit represented by the formula (11B).
  • a compound having a structural unit represented by the above formula (11A) and a compound having a structural unit represented by the above formula (11B) may be included.
  • a compound having a structural unit represented by the formula (11) may include a compound having a structural unit represented by the formula (11A) and a compound having a structural unit represented by the formula (11B). . In this case, even if the compound having the structural unit represented by the formula (11) is a compound having the structural unit represented by the formula (11A) and the structural unit represented by the formula (11B) good.
  • the structural unit represented by formula (11) above may be the structural unit represented by formula (11A) above, or the structural unit represented by formula (11B) above.
  • the compound having the structural unit represented by formula (11) preferably contains a compound having the structural unit represented by formula (11A).
  • the structural unit represented by formula (11) above is preferably the structural unit represented by formula (11A) above.
  • the content of the compound having the structural unit represented by the above formula (11) is preferably 1% by weight or more, more preferably 5% by weight, based on 100% by weight of the spacer particles. Above, more preferably 10% by weight or more, preferably 50% by weight or less, more preferably 40% by weight or less, and even more preferably 30% by weight or less.
  • the compound having the structural unit represented by the formula (11) includes both the compound having the structural unit represented by the formula (11A) and the compound having the structural unit represented by the formula (11B). may contain. In this case, the content represents the sum of the content of the compound having the structural unit represented by formula (11A) and the content of the compound having the structural unit represented by formula (11B).
  • the spacer particles can be obtained by heating the adhesive particles.
  • the spacer particles can be obtained, for example, by heating the adhesive particles at 80° C. to 150° C. for 0.5 hours to 3 hours. More specific conditions can be obtained, for example, by heating the adhesive particles at 120° C. for 1 hour.
  • FIG. 3 is a cross-sectional view schematically showing a laminate using adhesive particles according to the first embodiment of the present invention.
  • the spacer particles 1X are adhered to the first base material 2 and the second base material 3 .
  • the material of the spacer particles 1X contains the adhesive particles.
  • the spacer particles 1X contain a compound having a structural unit represented by formula (11) above.
  • the spacer particles are formed in the layered body 51 by thermally curing the thermosetting resin or by reacting the compound having the structure represented by the formula (1). Further, the spacer particles can be formed between the first base material and the second base material by heat-curing the thermosetting resin or reacting the compound having the structure represented by the formula (1). glued to the material.
  • the laminate may or may not have a curved surface portion.
  • the laminate preferably has a curved surface portion.
  • the laminate may have a folded or curved shape.
  • the laminate preferably has a folded or curved shape, and is preferably used in a folded or curved shape.
  • the laminate may have a bent portion or a curved portion.
  • the laminate, the first substrate and the second substrate are flexible so that they can have a folded or curved shape.
  • the curvature of the curved surface portion of the laminate is preferably 300R or more and 1800R or less.
  • the adhesive particles according to the present invention can be used to reduce the thickness of the entire laminate. Adhesion can be sufficiently enhanced over a long period of time.
  • the laminate is preferably used for vehicle window glass, partitions, or the like.
  • Examples of the vehicle include vehicles, ships, aircraft, and the like.
  • the laminate is preferably used for window glass of vehicles such as vehicles, ships, and aircraft, partitions, and the like.
  • the laminate is preferably a windowpane or a partition, and more preferably a windowpane or a partition for a vehicle such as a vehicle, ship, or aircraft.
  • the laminate may be a window glass for a vehicle such as a vehicle, a ship, an aircraft, or the like, or may be a partition.
  • the vehicle is a transportation vehicle.
  • the partition may be a member that is arranged between the seats of the vehicle and partitions the seats.
  • the laminate may be a light modulating laminate.
  • the laminate is suitably used as a light control laminate.
  • the layered product is a light control layered product, it is preferable that the layered product further includes a light control layer arranged between the first base material and the second base material.
  • the light modulating layer contains the spacer particles.
  • the light control layered product may be a PDLC (Polymer Dispersed Liquid Crystal) type light control layered product or an SPD (Suspended Particle Device) type light control layered product.
  • the light control layered product is preferably an SPD type or PDLC type light control layered product.
  • the light control laminate may not be a liquid crystal display device.
  • FIG. 4 is a cross-sectional view schematically showing a PDLC-type light control laminate using adhesive particles according to the first embodiment of the present invention.
  • FIG. 5 is a cross-sectional view schematically showing an SPD-type light control laminate using adhesive particles according to the first embodiment of the present invention.
  • the size, thickness, shape, amount of addition, etc. of the light modulating layer and the adhesive particles are appropriately changed from the actual size and shape for convenience of illustration.
  • the light modulating layer 4 is sandwiched between the first base material 2 and the second base material 3 .
  • the light control layer 4 is arranged between the first base material 2 and the second base material 3 .
  • a sealant may be arranged around the light control layer 4 .
  • the light control layer 4 includes spacer particles 1X, liquid crystal capsules 4A, and binders 4B.
  • the liquid crystal capsule 4A is a liquid crystal material.
  • the liquid crystal capsules 4A are dispersed in the binder 4B.
  • the liquid crystal capsule 4A is held in a capsule shape in the binder 4B.
  • the liquid crystal material may be encapsulated and dispersed in the binder, or the liquid crystal material may be dispersed in the binder as a continuous phase.
  • the spacer particles 1X are in contact with the first base material 2 and the second base material 3.
  • the spacer particles 1X control the gap between the first base material 2 and the second base material 3.
  • the spacer particles 1X contain a compound having a structural unit represented by formula (11) above.
  • the material of the spacer particles 1X contains the adhesive particles described above.
  • Electrodes are formed on the surface of the first base material 2 and on the surface of the second base material 3 (not shown). Examples of materials for the electrodes include indium tin oxide (ITO). The electrodes are preferably transparent electrodes.
  • the orientation of the liquid crystal molecules in the liquid crystal capsule 4A is not uniform. It scatters in the binder and becomes opaque.
  • the liquid crystal molecules in the liquid crystal capsule 4A are aligned in a direction parallel to the electric field.
  • the binder 4B and the liquid crystal material have the same refractive index, light can be transmitted therethrough, resulting in a transparent state.
  • the light modulating layer 5 is sandwiched between the first substrate 2 and the second substrate 3 .
  • the light control layer 5 is arranged between the first base material 2 and the second base material 3 .
  • the light control layer 5 includes spacer particles 1X, light control suspension liquid droplets 5A, and a resin matrix 5B. Droplets 5A of light conditioning suspension are dispersed in a resin matrix 5B. The droplets 5A of the light control suspension are held in a droplet state in the resin matrix 5B.
  • the droplets 5A of the light adjusting suspension contain the dispersion medium 5Aa and the light adjusting particles 5Ab.
  • the light adjusting particles 5Ab are dispersed in the dispersion medium 5Aa.
  • the spacer particles 1X are in contact with the first base material 2 and the second base material 3.
  • the spacer particles 1X control the gap between the first base material 2 and the second base material 3.
  • the spacer particles 1X contain a compound having a structural unit represented by formula (11) above.
  • the material of the spacer particles 1X contains the adhesive particles described above.
  • Electrodes are formed on the surface of the first base material 2 and on the surface of the second base material 3 (not shown).
  • Materials for the transparent electrode include indium tin oxide (ITO) and the like.
  • the electrodes are preferably transparent electrodes.
  • the light adjustment particles 5Ab are arranged in a direction parallel to the electric field. Therefore, the incident light can pass between the arranged light adjusting particles 5Ab and can be transmitted through the light adjusting layer 5.
  • the light control layer preferably has light control properties. Dimmability is a property that the visible light transmittance changes depending on whether or not an electric field is applied, and the amount of incident light can be adjusted.
  • the light control layer includes the spacer particles.
  • the light modulating layer preferably further includes a binder and a liquid crystal material dispersed in the binder.
  • the liquid crystal material is not particularly limited, and may be any liquid crystal material as long as it has the property of changing its orientation when an electric field is applied.
  • the liquid crystal material may be dispersed in the binder as a continuous phase, or may be dispersed in the binder in the form of liquid crystal drops or liquid crystal capsules.
  • Examples of the liquid crystal material include nematic liquid crystal and cholesteric liquid crystal.
  • nematic liquid crystal Materials for the nematic liquid crystal include cyanobiphenyl, phenyl ester, azoxybenzene, fluorine-containing biphenyl, carbonate, and Schiff base materials. Only one kind of the nematic liquid crystal material may be used, or two or more kinds thereof may be used in combination.
  • Materials for the cholesteric liquid crystal include steroidal cholesterol derivatives, Schiff bases, azos, azoxys, benzoates, biphenyls, terphenyls, cyclohexylcarboxylates, phenylcyclohexanes, biphenylcyclohexanes, and pyrimidines.
  • cholesteric liquid crystal material Only one kind of the cholesteric liquid crystal material may be used, or two or more kinds thereof may be used in combination.
  • the binder holds the liquid crystal material and suppresses the flow of the liquid crystal material.
  • the binder is not particularly limited as long as it does not dissolve in the liquid crystal material, has strength to withstand external force, and has high transparency to reflected light and incident light.
  • the binder material include water-soluble polymer materials such as gelatin, polyvinyl alcohol, cellulose derivatives, polyacrylic acid-based polymers, ethyleneimine, polyethylene oxide, polyacrylamide, polystyrene sulfonate, polyamidine, isoprene-based sulfonic acid polymers, and materials capable of forming an aqueous emulsion such as fluorine resin, silicone resin, acrylic resin, urethane resin, and epoxy resin. Only one kind of the binder material may be used, or two or more kinds thereof may be used in combination.
  • the binder is preferably crosslinked with a crosslinking agent.
  • the cross-linking agent is not particularly limited as long as it forms cross-links between the binders and hardens the binder, makes it insoluble, or makes it insoluble.
  • Examples of the cross-linking agent include acetaldehyde, glutaraldehyde, glyoxal, potassium alum hydrate of a polyvalent metal salt compound, adipic acid dihydrazide, melamine formalin oligomer, ethylene glycol diglycidyl ether, polyamide epichlorohydrin, and polycarbodiimide. mentioned. Only one kind of the crosslinking agent may be used, or two or more kinds thereof may be used in combination.
  • the light control layer further comprises a resin matrix and a light control suspension dispersed in the resin matrix.
  • the light control suspension contains a dispersion medium and light control particles dispersed in the dispersion medium.
  • the light adjusting particles include carbon-based materials such as polyiodide and carbon black, metal materials such as copper, nickel, iron, cobalt, chromium, titanium, and aluminum, and inorganic compound materials such as silicon nitride, titanium nitride, and aluminum oxide. etc. Also, these materials may be particles coated with a polymer. Only one type of the light adjusting particles may be used, or two or more types may be used in combination.
  • the dispersion medium disperses the light adjustment particles in a fluid state.
  • the dispersion medium selectively adheres to the light control particles, coats the light control particles, and causes the light control particles to migrate to the phase-separated droplet phase upon phase separation from the resin matrix.
  • It is preferably a material that is functional, non-electrically conductive, and incompatible with the resin matrix.
  • the dispersion medium is preferably a liquid copolymer having a refractive index similar to that of the resin matrix when the light control laminate is formed.
  • a (meth)acrylic ester oligomer having a fluoro group or a hydroxyl group is preferable, and a (meth)acrylic ester oligomer having a fluoro group and a hydroxyl group is more preferable.
  • the fluoro or hydroxyl monomer units are oriented toward the light modulating particles and the remaining monomer units stabilize the droplets of the light modulating suspension in the resin matrix. Therefore, the light control particles are easily dispersed in the light control suspension, and the light control particles are easily guided into the phase-separated droplets during phase separation from the resin matrix.
  • Examples of the (meth)acrylic acid ester oligomer having a fluoro group or a hydroxyl group include 2,2,2-trifluoroethyl methacrylate/butyl acrylate/2-hydroxyethyl acrylate copolymer, and 3,5,5 acrylic acid.
  • the weight average molecular weight of the (meth)acrylate oligomer is preferably 1000 or more, more preferably 2000 or more, and preferably 20000 or less, more preferably 10000 or less.
  • the light control layer can be produced using the resin material for forming the resin matrix and the light control suspension.
  • the resin material is preferably a resin material that cures when irradiated with energy rays.
  • resin materials that are cured by irradiation with energy rays include polymer compositions that contain photopolymerization initiators and polymer compounds that are cured by energy rays such as ultraviolet rays, visible rays, and electron beams.
  • the polymer composition include a polymer composition containing a polymerizable monomer having an ethylenically unsaturated group and a photopolymerization initiator.
  • the polymerizable monomer having an ethylenically unsaturated group include non-crosslinkable monomers and crosslinkable monomers.
  • non-crosslinkable monomers examples include vinyl compounds such as styrene monomers such as styrene, ⁇ -methylstyrene, and chlorostyrene; vinyl ether compounds such as methyl vinyl ether, ethyl vinyl ether, and propyl vinyl ether; vinyl acetate, vinyl butyrate, Acid vinyl ester compounds such as vinyl laurate and vinyl stearate; halogen-containing monomers such as vinyl chloride and vinyl fluoride; ) Alkyl ( meth) acrylate compounds; oxygen atom-containing (meth) acrylate compounds such as 2-hydroxyethyl (meth) acrylate, glycerol (meth) acrylate, polyoxyethylene (meth) acrylate, glycidyl (meth) acrylate; (meth) acrylonitrile and the like Nitrile-containing monomers; halogen-containing (meth)acrylate compounds such as trifluoromethyl (meth)acrylate and pentafluor
  • crosslinkable monomers examples include vinyl monomers such as divinylbenzene, 1,4-divinyloxybutane and divinylsulfone as vinyl compounds; and tetramethylolmethane tetra(meth)acrylate as (meth)acrylic compounds.
  • polytetramethylene glycol diacrylate tetramethylolmethane tri(meth)acrylate, tetramethylolmethane di(meth)acrylate, trimethylolpropane tri(meth)acrylate, dipentaerythritol hexa(meth)acrylate, dipentaerythritol penta(meth)acrylate ) acrylate, glycerol tri(meth)acrylate, glycerol di(meth)acrylate, polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, polytetramethylene glycol di(meth)acrylate, 1,3-butylene glycol di(meth)acrylate Polyfunctional (meth)acrylate compounds such as (meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonaned
  • photopolymerization initiator examples include 2,2-dimethoxy-1,2-diphenylethan-1-one, 1-(4-(2-hydroxyethoxy)phenyl)-2-hydroxy-2-methyl-1-propane -1-one, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, 2-hydroxy-2-methyl-1-phenylpropan-1-one, and (1-hydroxycyclohexyl)phenylketone. be done.
  • the resin material may contain organic solvent-soluble resin, thermoplastic resin, poly(meth)acrylic acid, and the like.
  • the resin material may contain various additives such as an anti-coloring agent, an antioxidant, and an adhesion imparting agent, and may contain a solvent.
  • the first substrate is preferably a transparent substrate.
  • the second base material is preferably a transparent base material.
  • the transparent substrate is, for example, a substrate having optical transparency (light transmissive substrate). For example, light is transmitted from one side of the transparent substrate to the other side through the transparent substrate. For example, when viewing a substance on the other side through the transparent substrate from one side of the transparent substrate, the substance can be visually recognized. Transparency also includes translucence, for example.
  • the transparent substrate may be colorless and transparent, or may be colored and transparent.
  • the materials of the first base material and the second base material are not particularly limited.
  • the material of the first base material and the material of the second base material may be the same or different.
  • Materials for the substrate include glass and resin films.
  • the glass include soda-lime glass, lead glass, borosilicate glass for general construction, glasses of various compositions for other applications, and functional glasses such as heat-reflecting glass, heat-absorbing glass, and tempered glass.
  • the resin film include polyester films such as polyethylene terephthalate, polyolefin films such as polypropylene, and resin films such as acrylic resin films.
  • the base material is preferably a resin base material, more preferably a resin film, and a polyethylene terephthalate (PET) film because of its excellent transparency, moldability, adhesiveness, workability, etc. is more preferred.
  • the substrate preferably includes a substrate body and a conductive film formed on the surface of the substrate body so that an electric field for dimming can be applied.
  • the conductive film include indium tin oxide (ITO), SnO 2 and In 2 O 3 .
  • the conductive film is preferably a transparent conductive film.
  • the visible light transmittance of the first base material and the second base material is preferably 75% or more, more preferably 80% or more.
  • the visible light transmittance of the base material can be measured in accordance with ISO13837:2008 by carrying out spectrometry or the like.
  • Curing agent I amine curing agent, "Norbornanediamine” manufactured by Mitsui Chemicals Fine Co., Ltd.
  • Curing agent II aromatic amine curing agent, "4,4'-diaminodiphenylmethane” manufactured by Tokyo Chemical Industry Co., Ltd.
  • adhesive particles 15 parts by weight of bisphenol A epoxy resin, 12 parts by weight of liquid epoxy resin, 3 parts by weight of compound A, and 17 parts by weight of a dispersion stabilizer (polyvinylpyrrolidone) were placed in a reaction vessel equipped with a thermometer, a stirrer, and a cooling pipe. , and 550 parts by weight of ethanol were added and stirred at 45° C. for 1 hour to dissolve uniformly. Next, 2.5 parts by weight of curing agent I was added into the reaction vessel and reacted at 45° C. for 20 hours to obtain a reaction product. After washing the resulting reaction product with methanol, a classification operation was performed to recover the adhesive particles.
  • a dispersion stabilizer polyvinylpyrrolidone
  • Examples 2--7 The type and content (% by weight) of the resin, the type and content (% by weight) of the curing agent, and the type and content (% by weight) of the compound having the structure represented by the above formula (1) are shown in Table 1, Adhesive particles were produced in the same manner as in Example 1, except that the composition was changed as shown in 2.
  • the aqueous solution B was added. After that, emulsification was performed using a Shirasu Porous Glass (SPG) membrane (average pore size: about 20 ⁇ m). After that, the temperature was raised to 85° C. and polymerization was carried out for 9 hours. The whole amount of the polymerized particles was washed with water by centrifugation, classified, and freeze-dried to obtain substrate particles (particle size: 20 ⁇ m).
  • SPG Shirasu Porous Glass
  • Example 8 2.0 parts by weight of base particles, 1.8 parts by weight of epoxy resin (equal mixture of bisphenol A type epoxy resin and liquid epoxy resin), and dispersion 5.9 parts by weight of a stabilizer (polyvinylpyrrolidone), 1.2 parts by weight of cetyltrimethylammonium bromide, and 250 parts by weight of methanol were added. Then, it was uniformly dissolved by stirring at 45° C. for 1 hour. Next, 0.6 parts by weight of compound A and 0.1 parts by weight of curing agent I were added into the reaction vessel and reacted at 45° C. for 20 hours to obtain a reaction product. After the obtained reaction product was washed with methanol, a classification operation was performed to recover adhesive particles each having a substrate particle and a coating portion arranged on the surface of the substrate particle.
  • epoxy resin equal mixture of bisphenol A type epoxy resin and liquid epoxy resin
  • a stabilizer polyvinylpyrrolidone
  • cetyltrimethylammonium bromide 1.2 parts by weight of cety
  • Example 9 4.0 parts by weight of base particles, 1.6 parts by weight of epoxy resin (equal mixture of bisphenol A type epoxy resin and liquid epoxy resin), and dispersion 11 parts by weight of a stabilizer (polyvinylpyrrolidone), 2.4 parts by weight of cetyltrimethylammonium bromide, and 500 parts by weight of methanol were added. Then, it was uniformly dissolved by stirring at 45° C. for 1 hour. Next, 0.2 parts by weight of compound A and 0.1 parts by weight of curing agent I were added into the reaction vessel and reacted at 45° C. for 20 hours to obtain a reaction product. After the obtained reaction product was washed with methanol, a classification operation was performed to recover adhesive particles each having a substrate particle and a coating portion arranged on the surface of the substrate particle.
  • epoxy resin epoxy resin
  • a stabilizer polyvinylpyrrolidone
  • cetyltrimethylammonium bromide 2.4 parts by weight of cetyltrimethylammonium bromide
  • Comparative Examples 1 and 2 In Comparative Examples 1 and 2, the compound having the structure represented by the above formula (1) was not used, and the average particle size of the adhesive particles was changed as shown in Table 2. Adhesive particles were prepared in the same manner as in Example 1.
  • a light control film was prepared in which a known SPD layer was arranged between two sheets of PET film on which transparent and conductive ITO was vapor-deposited, except that 5% by weight of the obtained adhesive particles were dispersed.
  • a light control film was sandwiched between two sheets of transparent glass, a weight of 5 kg was placed, placed on a hot plate, and heated at 120°C for 1 hour, so that the spacer particles adhered to the first and second substrates.
  • An SPD type light control laminate was produced.
  • a light control film was prepared by disposing a known PDLC layer between two sheets of PET film on which transparent and conductive ITO was vapor-deposited, except that 5% by weight of the obtained adhesive particles were dispersed.
  • a light control film was sandwiched between two sheets of transparent glass, a weight of 5 kg was placed, placed on a hot plate, and heated at 120°C for 1 hour, so that the spacer particles adhered to the first and second substrates.
  • a PDLC type light control laminate was produced.
  • Average Particle Size About 100,000 particles of the obtained adhesive particles were measured for particle size using a particle size distribution analyzer (“Multisizer 4” manufactured by Beckman Coulter, Inc.) to measure the average particle size.
  • Adhesion tensile yield stress
  • a test body test sample was prepared according to the above-described adhesion test A.
  • Tensilon universal material testing machine RTI-1310 manufactured by A&D was used to measure the tensile yield stress of the specimen at 23°C (adhesion test A).
  • Adhesion (tensile yield stress) was determined according to the following criteria.
  • Tensile yield stress is 0.12 MPa or more
  • Tensile yield stress is 0.10 MPa or more and less than 0.12 MPa
  • Tensile yield stress is 0.07 MPa or more and less than 0.10 MPa
  • Tensile yield stress is 0.07 MPa less than
  • Adhesiveness (90° peel strength) Using the obtained adhesive particles, a test body (test sample) was prepared according to the above-described adhesion test B. In accordance with JIS K6854: 1999, using a tensile tester ("Autograph AGS" manufactured by Shimadzu Corporation), the 90 ° peel strength at 23 ° C. of the above test body was measured at a tensile speed of 50 mm / sec (adhesion sex test B). Adhesiveness (90° peel strength) was judged according to the following criteria.
  • the obtained light control laminate was curved using a cylindrical plate having a curvature of 0.1 to obtain a light control laminate having a curved surface portion.
  • VHX-2000 manufactured by Keyence Corporation
  • the number of remaining spacer particles was counted in five arbitrary 1 cm 2 regions on the surface of the second substrate. The standard deviation of the number of remaining spacer particles was determined, and the survivability of the spacer particles was judged according to the following criteria.
  • Standard deviation is less than 2 ⁇ : Standard deviation is 2 or more and less than 3 ⁇ 1: Standard deviation is 3 or more and less than 4 ⁇ 2: Standard deviation is 4 or more and less than 6 ⁇ : Standard deviation is 6 or more
  • the obtained light control laminate was curved using a cylindrical plate having a curvature of 0.1 to obtain a light control laminate having a curved surface portion.
  • the thickness of the light modulating layer of the light modulating laminate was measured using a scanning electron microscope.
  • the ratio of the minimum thickness of the light control layer to the maximum thickness of the light control layer was calculated, and the gap controllability was calculated as follows. Judged by the standard.
  • composition and results of the adhesive particles are shown in Tables 1 and 2 below.
  • Reference Signs List 1 1A Adhesive particles 11A Substrate particles 12A Coating portion 1X Spacer particles 2 First substrate 3 Second substrate 4, 5 Light control layer 4A Liquid crystal capsule 4B Binder 5A Liquid droplets of light control suspension 5Aa... Dispersion medium 5Ab... Light control particles 5B... Resin matrix 51... Laminated body 52... PDLC type light control layered body 53... SPD type light control layered body

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WO2018016378A1 (ja) * 2016-07-19 2018-01-25 積水化学工業株式会社 調光積層体及び調光積層体用樹脂スペーサ
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