WO2020213159A1 - Produit optique à faible frange d'interférence et agent de revêtement pour celui-ci - Google Patents

Produit optique à faible frange d'interférence et agent de revêtement pour celui-ci Download PDF

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Publication number
WO2020213159A1
WO2020213159A1 PCT/JP2019/016851 JP2019016851W WO2020213159A1 WO 2020213159 A1 WO2020213159 A1 WO 2020213159A1 JP 2019016851 W JP2019016851 W JP 2019016851W WO 2020213159 A1 WO2020213159 A1 WO 2020213159A1
Authority
WO
WIPO (PCT)
Prior art keywords
hard coat
coat layer
silane coupling
coupling agent
layer
Prior art date
Application number
PCT/JP2019/016851
Other languages
English (en)
Japanese (ja)
Inventor
紘 大石
敏哉 上野
芳昭 宮本
Original Assignee
日本精化株式会社
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 日本精化株式会社 filed Critical 日本精化株式会社
Priority to PCT/JP2019/016851 priority Critical patent/WO2020213159A1/fr
Priority to TW109112646A priority patent/TW202104474A/zh
Publication of WO2020213159A1 publication Critical patent/WO2020213159A1/fr

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/38—Layered products comprising a layer of synthetic resin comprising epoxy resins
    • 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
    • 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
    • B32B7/02—Physical, chemical or physicochemical properties
    • B32B7/023—Optical properties
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions 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
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/61—Additives non-macromolecular inorganic
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
    • G02B1/14—Protective coatings, e.g. hard coatings

Definitions

  • the present invention relates to optical articles such as spectacle lenses, particularly optical articles in which the generation of interference fringes is suppressed, and coating agents used for such optical articles.
  • Optical articles such as spectacle lenses have a laminated structure in which an antireflection layer, an antifouling layer, etc. are coated on a glass or plastic base material.
  • a plastic base material is often used to reduce the weight of eyeglasses, but since the surface of the plastic base material is easily scratched, a hard coat layer is formed to protect the surface.
  • it is required to appropriately set the thickness and the refractive index of each member.
  • Patent Document 1 describes a problem that interference fringes are generated due to a difference in refractive index between a transparent base film such as a PET film and a transparent hard coat layer and a slight variation in thickness, resulting in a decrease in visibility. It is described that fine particles of metal oxides such as zirconium oxide and titanium oxide are blended as a high refractive index in the coating agent, and the interference fringes are eliminated by matching the reflectance with the reflectance of the easy-adhesion layer of the PET film. There is. However, since fine particles of metal oxides such as zirconium oxide and titanium oxide are expensive, there is a problem that the production cost is high.
  • Patent Document 2 discloses an spectacle lens in which a functional layer including a hard coat layer having a constant refractive index and a primer layer having a constant refractive index is formed on a plastic base material.
  • a functional layer including a hard coat layer having a constant refractive index and a primer layer having a constant refractive index is formed on a plastic base material.
  • Patent Document 2 proposes to suppress the occurrence of interference fringes by setting the thickness T of the functional layer in the range of 9.1 to 100 ⁇ m.
  • the occurrence of interference fringes can be further suppressed by increasing, equating, decreasing or making the refractive index of the lens substrate, the refractive index of the primer layer, and the refractive index of the hard coat layer in this order. ..
  • the hard coat layer becomes thick, there is a problem that the hard coat layer is cracked during manufacturing.
  • Patent Document 3 has a lens base material and a hard coat layer, and the hard coat layer is polyfunctional in an amount of more than 40% by mass and 60% by mass or less in the inorganic oxide particles, the silane coupling agent, and the matrix component.
  • an optic lens obtained by curing a curable composition containing a sex epoxy compound.
  • this spectacle lens cracks during manufacturing are suppressed by setting the film thickness of the hard coat layer to 10 ⁇ m or more and 50 ⁇ m or less.
  • the content of the polyfunctional epoxy compound exceeds 40%, there is a problem that sufficient hardness cannot be obtained.
  • an object of the present invention is that in an optical article in which a functional layer of a hard coat layer including a hard coat layer or a primer layer is formed on a plastic layer having a high refractive index, fine particles of metal oxides such as zirconia and titanium oxide are formed.
  • the purpose is to make the interference fringes inconspicuous and to suppress the occurrence of cracks during the production of the hard coat layer without blending the high refractive index agent.
  • the present invention at least suppresses the total thickness of the hard coat layer and the primer layer to reduce the occurrence of interference fringes, and the hard coat layer contains a mixture of a trifunctional silane coupling agent and a bifunctional silane coupling agent. By doing so, the generation of cracks during manufacturing is suppressed.
  • Examples of the material of the plastic base material that can be used in the present invention include diallyl carbonate, polycarbonate, polyurethane, polythiourethane, and episulfide (refractive index 1.40 to 1.84).
  • Examples of the material of the primer layer that can be used in the present invention include polyurethane resin, polyester resin, acrylic resin, and epoxy resin.
  • the primer layer can be formed on the plastic base material by a known method such as dip coating, die coating, flow coating, and gravure coating.
  • the hard coat layer that can be used in the present invention is formed by using a coating agent prepared by adding an epoxy group-containing silane coupling agent, an inorganic oxide such as silica particles, a polyfunctional epoxy, or the like.
  • the hard coat layer can be formed on the plastic base material by a known method such as dip coating, die coating, flow coating, and gravure coating.
  • the epoxy resin used for the hard coat layer of the present invention is preferably a compound having two or more epoxy groups from the viewpoint of maintaining hardness, and examples thereof include an aliphatic epoxy compound, an alicyclic epoxy compound, and an aromatic epoxy compound.
  • aliphatic epoxy compounds include 1,6-hexanediol diglycidyl ether, ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, tetraethylene glycol diglycidyl ether, and nonaethylene glycol diglycidyl ether.
  • Examples of alicyclic epoxy compounds include 3,4-epoxycyclohexylmethyl-3', 4'-epoxycyclohexanecarboxylate, isophoronediol diglycidyl ether, bis-2,2-hydroxycyclohexylpropanediglycidyl ether and the like.
  • Examples of aromatic epoxy compounds include resorcin diglycidyl ether, bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, bisphenol S diglycidyl ether, orthophthalate diglycidyl ester, phenol novolac polyglycidyl ether, cresol novolac polyglycidyl ether and the like. Including.
  • the epoxy group-containing silane coupling agent used for the hard coat layer of the present invention is (A) glycidoxymethyltrimethoxysilane, glycidoxymethyltriethoxysilane, ⁇ -glycidoxyethyltriethoxysilane, ⁇ -glycid.
  • the trifunctional silane cup The solid content ratio of the ring agent to the bifunctional silane coupling agent (trifunctional silane coupling agent: bifunctional silane coupling agent) is preferably 95: 5 to 10:90, more preferably 90:10. ⁇ 10: 90.
  • the inorganic oxide used for the hard coat layer of the present invention includes particles such as zinc oxide (ZnO), silicon dioxide (SiO 2 ), titanium oxide (TiO 2 ), zirconium oxide (ZrO 2 ), and tin oxide (SnO 2 ). Can be mentioned. Although silicon dioxide is preferred, they can be used alone or in combination with two or more inorganic oxides.
  • an inorganic or organic antireflection layer can be further formed on the hard coat layer, if necessary.
  • an antifouling layer can be further formed on the antireflection layer, if necessary.
  • the antifouling layer has a function of imparting water repellency and oil repellency to the surface of the optical article, and is, for example, a layer made of an organosilicon compound containing fluorine.
  • the present invention since a mixture of a trifunctional silane coupling agent and a bifunctional silane coupling agent is blended in the hard coat layer, even if the film thickness of the hard coat layer is increased to reduce interference fringes, It is possible to suppress the occurrence of cracks during manufacturing.
  • the optical article of the present invention has at least a plastic base material and a hard coat layer formed on the plastic base material.
  • the refractive index of the plastic substrate is 1.40 to 1.84
  • the thickness of the hard coat layer is 15 to 30 ⁇ m
  • the trifunctional silane coupling agent is 1.
  • a mixture of bifunctional silane coupling agents is provided.
  • the optical article of the present invention may be provided with a primer layer on a plastic base material.
  • the refractive index of the primer layer at that time is preferably in the range of 1.45 to 1.67.
  • Component A Metal oxide A-1: Water-dispersed silica sol (Snowtex O: manufactured by Nissan Chemical Industries, Ltd., etc.) A-2: Organic solvent-dispersed silica sol (methanol silica sol: manufactured by Nissan Chemical Industries, Ltd., etc.)
  • Component B Epoxy group-containing silane coupling agent B-1: ⁇ -glycidoxypropyltrimethoxysilane (GPTMS) B-2: ⁇ -glycidoxypropyltriethoxysilane (GPTES) B-3: ⁇ -glycidoxypropyl (methyl) dimethoxysilane (GPDMS) B-4: ⁇ -glycidoxypropyl (methyl) diethoxysilane (GPDES)
  • Component C Polyfunctional epoxy compound JER827 (manufactured by Mitsubishi Chemical Corporation) Ingredient D: Leveling agent SH28PA (manufactured by Toray Dow Corning Co., Ltd.)
  • Component E Curing catalyst Aluminum tris
  • Example 1 16.2 parts by mass of A-1 and 21.6 parts by mass of A-2 were added as the component A, 51.9 parts by mass of B-1 was added as the component B, and the mixture was stirred at 40 ° C. for 2 hours.
  • As the F component 15.0 parts by mass of F-1 and 1.8 parts by mass of F-2 were added, and 2.5 parts by mass of C component, 1.0 part by mass of D component, and 2.1 parts by mass of E component were added. Then, the solvent was recovered to obtain a coating liquid having a solid content concentration of 60%. Using the coating liquid, dip coat the lenses with different refractive indexes, pre-dry them at 80 ° C. for 10 minutes, and then heat-cure them at 120 ° C. for 1 hour to form a hard coat layer. The appearance (presence or absence of cracks) and scratch resistance were evaluated.
  • the plastic base material and the optical article in which the hard coat layer is formed on the plastic base material, and the refractive index of the plastic base material is 1.40 to 1.84.
  • the thickness of the hard coat layer is in the range of 15 ⁇ m to 30 ⁇ m, and the hard coat layer contains a trifunctional silane coupling agent and a bifunctional silane coupling agent, preferably 95: 5 to 10:90.
  • Optical articles can be provided that include a mixture containing in a solid content ratio of 90:10 to 10:90. In such an optical article, interference fringes are suppressed, and even if the film thickness of the hard coat layer is increased, cracks do not occur during manufacturing.
  • the solid content concentration of the coating liquid was 35% (Comparative Example 3)
  • the film thickness was forcibly increased, the appearance deteriorated. Therefore, by setting the solid content concentration of the coating liquid in the range of 40 to 70%, preferably 55 to 70% in order to increase the film thickness, it is possible to provide an optical article in which interference fringes are suppressed.
  • ⁇ Evaluation method> (1) Measurement of film thickness A reflection spectroscopic film thickness meter FE-3000 manufactured by Otsuka Electronics Co., Ltd. was used to measure the film thickness of each layer after curing. (2) Confirmation of interference fringes Interference fringes were visually confirmed under a three-wavelength fluorescent lamp. The evaluation criteria were ⁇ for those who passed and ⁇ for those who failed. (3) Initial appearance The coating film formed up to the hard coat layer was visually confirmed to evaluate the occurrence of cracks. Those without cracks were marked with ⁇ , and those with cracks were marked with x.
  • an optical article such as a spectacle lens
  • interference fringes are not conspicuous and crack generation during manufacturing can be suppressed.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Inorganic Chemistry (AREA)
  • Optics & Photonics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Surface Treatment Of Optical Elements (AREA)
  • Laminated Bodies (AREA)

Abstract

Produit optique comprenant une couche de plastique ayant un indice de réfraction élevé sur lequel est formée une couche de revêtement dur ou une couche fonctionnelle comprenant une couche d'apprêt et une couche de revêtement dur, une composition d'agent de revêtement étant fournie, rendant les franges d'interférence moins visibles et supprimant l'apparition de fissures pendant la production de la couche de revêtement dur, sans avoir à mélanger de fines particules d'oxyde métallique tel que de l'oxyde de zirconium et de l'oxyde de titane à l'intérieur de celles-ci. Cette composition d'agent de revêtement contient un agent de couplage silane trifonctionnel et un agent de couplage silane bifonctionnel à un rapport de teneur en solides de 95:5 à 10:90.
PCT/JP2019/016851 2019-04-19 2019-04-19 Produit optique à faible frange d'interférence et agent de revêtement pour celui-ci WO2020213159A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/JP2019/016851 WO2020213159A1 (fr) 2019-04-19 2019-04-19 Produit optique à faible frange d'interférence et agent de revêtement pour celui-ci
TW109112646A TW202104474A (zh) 2019-04-19 2020-04-15 低干涉條紋光學物品及其塗佈劑

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/JP2019/016851 WO2020213159A1 (fr) 2019-04-19 2019-04-19 Produit optique à faible frange d'interférence et agent de revêtement pour celui-ci

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WO2020213159A1 true WO2020213159A1 (fr) 2020-10-22

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4186949A4 (fr) * 2020-10-16 2024-04-17 Nippon Fine Chemical Co., Ltd. Produit optique à franges d'interférence réduites et composition d'agent de revêtement s'y rapportant

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02117976A (ja) * 1988-10-26 1990-05-02 Asahi Optical Co Ltd コーティング組成物
JPH1010301A (ja) * 1996-04-12 1998-01-16 Nikon Corp フォトクロミックプラスチックレンズ及びその製造方法
JPH11119167A (ja) * 1997-10-15 1999-04-30 Nikon Corp ジオプトリーが異なる複数のメガネレンズの組み合わせ
JPH11133204A (ja) * 1997-09-01 1999-05-21 Seiko Epson Corp 硬化膜付きプラスチックレンズ
US20020061407A1 (en) * 1998-12-29 2002-05-23 Colton James P. Abrasion resistant coating composition and coated articles
US20060158747A1 (en) * 2005-01-18 2006-07-20 Yuji Kato Plastic lens for spectacles
JP2012078538A (ja) * 2010-09-30 2012-04-19 Fujifilm Corp ハードコート層を有する反射防止フィルム、該反射防止フィルムの製造方法、該反射防止フィルムを具備する偏光板及び液晶表示装置
JP5464846B2 (ja) * 2008-12-01 2014-04-09 ホーヤ レンズ マニュファクチャリング フィリピン インク 眼鏡レンズ、眼鏡および眼鏡レンズ製造方法
JP2014091750A (ja) * 2012-11-01 2014-05-19 Kikusui Chemical Industries Co Ltd コーティング剤組成物
WO2015163464A1 (fr) * 2014-04-24 2015-10-29 ホヤ レンズ タイランド リミテッド Verre de lunettes
JP2018123043A (ja) * 2017-02-03 2018-08-09 日揮触媒化成株式会社 シリカ系粒子分散液の製造方法、シリカ系粒子分散液、透明被膜形成用塗布液及び透明被膜付基材

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02117976A (ja) * 1988-10-26 1990-05-02 Asahi Optical Co Ltd コーティング組成物
JPH1010301A (ja) * 1996-04-12 1998-01-16 Nikon Corp フォトクロミックプラスチックレンズ及びその製造方法
JPH11133204A (ja) * 1997-09-01 1999-05-21 Seiko Epson Corp 硬化膜付きプラスチックレンズ
JPH11119167A (ja) * 1997-10-15 1999-04-30 Nikon Corp ジオプトリーが異なる複数のメガネレンズの組み合わせ
US20020061407A1 (en) * 1998-12-29 2002-05-23 Colton James P. Abrasion resistant coating composition and coated articles
US20060158747A1 (en) * 2005-01-18 2006-07-20 Yuji Kato Plastic lens for spectacles
JP5464846B2 (ja) * 2008-12-01 2014-04-09 ホーヤ レンズ マニュファクチャリング フィリピン インク 眼鏡レンズ、眼鏡および眼鏡レンズ製造方法
JP2012078538A (ja) * 2010-09-30 2012-04-19 Fujifilm Corp ハードコート層を有する反射防止フィルム、該反射防止フィルムの製造方法、該反射防止フィルムを具備する偏光板及び液晶表示装置
JP2014091750A (ja) * 2012-11-01 2014-05-19 Kikusui Chemical Industries Co Ltd コーティング剤組成物
WO2015163464A1 (fr) * 2014-04-24 2015-10-29 ホヤ レンズ タイランド リミテッド Verre de lunettes
JP2018123043A (ja) * 2017-02-03 2018-08-09 日揮触媒化成株式会社 シリカ系粒子分散液の製造方法、シリカ系粒子分散液、透明被膜形成用塗布液及び透明被膜付基材

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4186949A4 (fr) * 2020-10-16 2024-04-17 Nippon Fine Chemical Co., Ltd. Produit optique à franges d'interférence réduites et composition d'agent de revêtement s'y rapportant

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