WO2023243675A1 - 眼鏡レンズ - Google Patents

眼鏡レンズ Download PDF

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Publication number
WO2023243675A1
WO2023243675A1 PCT/JP2023/022175 JP2023022175W WO2023243675A1 WO 2023243675 A1 WO2023243675 A1 WO 2023243675A1 JP 2023022175 W JP2023022175 W JP 2023022175W WO 2023243675 A1 WO2023243675 A1 WO 2023243675A1
Authority
WO
WIPO (PCT)
Prior art keywords
lens
repeating unit
resin layer
compound
transmittance
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/JP2023/022175
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
クリストフ プロヴァン
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.)
Nikon Essilor Co Ltd
Original Assignee
Nikon Essilor 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 Nikon Essilor Co Ltd filed Critical Nikon Essilor Co Ltd
Priority to JP2024528934A priority Critical patent/JP7830643B2/ja
Priority to EP23823965.1A priority patent/EP4542287A1/en
Priority to CN202380046161.1A priority patent/CN119301511A/zh
Publication of WO2023243675A1 publication Critical patent/WO2023243675A1/ja
Priority to US18/982,184 priority patent/US20250116884A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • GPHYSICS
    • G02OPTICS
    • G02CSPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C7/00Optical parts
    • G02C7/02Lenses; Lens systems ; Methods of designing lenses
    • G02C7/022Ophthalmic lenses having special refractive features achieved by special materials or material structures
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00Processes of polymerisation
    • C08F2/46Polymerisation initiated by wave energy or particle radiation
    • C08F2/48Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F230/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
    • C08F230/04Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
    • C08F230/08Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041Lenses
    • GPHYSICS
    • G02OPTICS
    • G02CSPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C7/00Optical parts
    • GPHYSICS
    • G02OPTICS
    • G02CSPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C7/00Optical parts
    • G02C7/10Filters, e.g. for facilitating adaptation of the eyes to the dark; Sunglasses
    • G02C7/104Filters, e.g. for facilitating adaptation of the eyes to the dark; Sunglasses having spectral characteristics for purposes other than sun-protection

Definitions

  • Patent Document 1 describes, as the radically polymerizable component (A), a silsesquioxane component (A1) having a radically polymerizable group and a bifunctional radically polymerizable monomer (A2) represented by the general formula (1).
  • a photochromic curable composition is disclosed, which further contains a photochromic compound (B).
  • the present disclosure provides a spectacle lens having a lens base material and a resin layer disposed on the lens base material, the resin layer containing a compound represented by formula (A) and a resin,
  • the resin contains repeating unit 1 derived from silsesquioxane having a polymerizable group and repeating unit 2 derived from a monofunctional monomer, and the mass ratio of repeating unit 1 to repeating unit 2 is 60/40 to 95/5. and relates to an eyeglass lens whose transmittance at a wavelength of 556 nm is 65 to 80%.
  • FIG. 1 is a cross-sectional view of one embodiment of a spectacle lens.
  • a spectacle lens 10 shown in FIG. 1 has a lens base material 12 and a resin layer 14 disposed on the lens base material 12.
  • the resin layer 14 is arranged so as to be in direct contact with the lens base material 12, but the present invention is not limited to this form, and other layers (for example, , primer layer, etc.) may be disposed. That is, the resin layer 14 may be placed directly on the lens base material 12, or may be placed indirectly on the lens base material 12 via another layer. Further, in FIG. 1, the resin layer 14 is arranged on one side of the lens base material 12, but the resin layer 14 may be arranged on both sides of the lens base material 12.
  • the eyeglass lens of the present disclosure provides a brightening effect indoors where ultraviolet rays are not substantially irradiated, whereas the eyeglass lens loses its color outdoors where ultraviolet rays are irradiated. Can be used as regular undyed eyeglass lenses.
  • the average transmittance of the spectacle lens in the wavelength range of 380 to 780 nm before specific irradiation is T 11 (%), and the average transmittance of the spectacle lens in the wavelength range of 380 to 780 nm after specific irradiation is T 12 (%).
  • T 11 is preferably 70 to 90%, more preferably 72 to 87%.
  • T 12 is preferably 80 to 90%, more preferably 85 to 90%.
  • ⁇ T 1 is preferably 2.0 to 20.0%, more preferably 2.0 to 18.0%.
  • the average transmittance of the eyeglass lens in the wavelength range of 380 to 780 nm before specific irradiation refers to the average transmittance of the eyeglass lens in the wavelength range of 380 to 780 nm when the eyeglass lens is left indoors under fluorescent light for 30 minutes, similar to the measurement of the transmittance of the eyeglass lens at a wavelength of 556 nm.
  • the transmittance was measured using the eyeglass lens after the treatment.
  • the average transmittance of the spectacle lens in the wavelength range of 430 to 470 nm before specific irradiation is T 21 (%)
  • the average transmittance of the spectacle lens in the wavelength range of 430 to 470 nm after specific irradiation is T 22 (%).
  • the spectacle lens satisfies the relationship of formula (2).
  • T 21 is preferably 75 to 90%, more preferably 84 to 90%.
  • T22 is preferably 82 to 90%, more preferably 85 to 90%.
  • ⁇ T 2 is preferably 0.0 to 6.0%, more preferably 0.0 to 3.0%.
  • the average transmittance of the eyeglass lens in the wavelength range of 430 to 470 nm before specific irradiation refers to the average transmittance of the eyeglass lens in the wavelength range of 430 to 470 nm when the eyeglass lens is left indoors under fluorescent light for 30 minutes, similar to the measurement of the transmittance of the eyeglass lens at a wavelength of 556 nm.
  • the transmittance was measured using the eyeglass lens after the treatment.
  • the average transmittance of the eyeglass lens in the wavelength range of 630 to 670 nm before specific irradiation refers to the average transmittance of the eyeglass lens in the wavelength range of 630 to 670 nm when the eyeglass lens is left indoors under fluorescent light for 30 minutes, similar to the measurement of the transmittance of the eyeglass lens at a wavelength of 556 nm.
  • the transmittance was measured using the eyeglass lens after the treatment.
  • the thickness of the lens base material is often 1 to 30 mm for ease of handling.
  • Repeating unit 1 is a repeating unit derived from silsesquioxane having a polymerizable group.
  • repeating unit 1 is a repeating unit obtained by polymerizing silsesquioxane having a polymerizable group.
  • the polymerizable group include radically polymerizable groups and cationic polymerizable groups.
  • radically polymerizable groups include (meth)acryloyl groups.
  • the cationically polymerizable group include alicyclic ether groups such as epoxy groups and oxetanyl groups, cyclic acetal groups, cyclic lactone groups, cyclic thioether groups, spiro-orthoester groups, and vinyloxy groups.
  • Repeating unit 2 is a repeating unit derived from a monofunctional monomer.
  • the repeating unit 2 is a repeating unit obtained by polymerizing a monofunctional monomer.
  • Monofunctional monomers are monomers that have one polymerizable group. Examples of the polymerizable group include the groups exemplified as the polymerizable group of the above-mentioned silsesquioxane, preferably a radically polymerizable group, and more preferably a (meth)acryloyl group.
  • the monofunctional monomer may have a functional group other than the polymerizable group.
  • monofunctional monomers include ethylene glycol monoethyl ether methacrylate, (meth)acrylic acid, 2-(2-ethoxyethoxy)ethyl acrylate, methoxypolyethylene glycol monoacrylate, methoxypolyethylene glycol monomethacrylate, phenoxypolyethylene glycol acrylate, 2-Acryloyloxyethyl succinate, 2-ethylhexyl acrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, tetrahydrofurfuryl acrylate, 2-ethylhexylcarbitol acrylate, 3-methoxybutyl acrylate, benzyl acrylate, cyclohexyl acrylate, isoamyl Acrylates, isobutyl acrylate, methoxytriethylene glycol acrylate, phenoxytetraethylene glycol acrylate, cetyl acrylate, isostearyl acrylate, steary
  • Resin X may be used alone or in combination of two or more.
  • the content of resin X is preferably 80 to 99.99% by mass, more preferably 85 to 99.95% by mass, and even more preferably 90 to 99% by mass, based on the total mass of the resin layer.
  • the thickness of the resin layer is preferably 1 to 150 ⁇ m, more preferably 2 to 40 ⁇ m, and even more preferably 5 to 25 ⁇ m.
  • each eyeglass lens was fixed at a position 10 cm from the light source using a slide projector (CABIN CS-15, manufactured by Iwasaki Electric Co., Ltd., using a halogen lamp), and irradiated with ultraviolet rays at 90 mW/cm 2 for 240 seconds.
  • the average transmittance in each wavelength region after specific irradiation was measured using a spectrophotometer (U-4100, manufactured by Hitachi), and the difference in average transmittance before and after specific irradiation in each wavelength region ( ⁇ T 1 ⁇ T 4 (results are shown in the average ⁇ T column in the table) were determined.
  • the undyed clear lens is the lens base material (lens base material 1 or lens base material 2) used in each eyeglass lens of Examples and Comparative Examples.

Landscapes

  • Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Ophthalmology & Optometry (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Eyeglasses (AREA)
PCT/JP2023/022175 2022-06-17 2023-06-15 眼鏡レンズ Ceased WO2023243675A1 (ja)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP2024528934A JP7830643B2 (ja) 2022-06-17 2023-06-15 眼鏡レンズ
EP23823965.1A EP4542287A1 (en) 2022-06-17 2023-06-15 Eyeglass lens
CN202380046161.1A CN119301511A (zh) 2022-06-17 2023-06-15 眼镜片
US18/982,184 US20250116884A1 (en) 2022-06-17 2024-12-16 Spectacle lens

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2022098334 2022-06-17
JP2022-098334 2022-06-17

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US18/982,184 Continuation US20250116884A1 (en) 2022-06-17 2024-12-16 Spectacle lens

Publications (1)

Publication Number Publication Date
WO2023243675A1 true WO2023243675A1 (ja) 2023-12-21

Family

ID=89191393

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2023/022175 Ceased WO2023243675A1 (ja) 2022-06-17 2023-06-15 眼鏡レンズ

Country Status (5)

Country Link
US (1) US20250116884A1 (https=)
EP (1) EP4542287A1 (https=)
JP (1) JP7830643B2 (https=)
CN (1) CN119301511A (https=)
WO (1) WO2023243675A1 (https=)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2025004856A1 (ja) * 2023-06-30 2025-01-02 株式会社ニコン・エシロール 組成物、眼鏡レンズ

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010204383A (ja) * 2009-03-03 2010-09-16 Idemitsu Kosan Co Ltd 赤色強調眼鏡及びゴーグル用樹脂成形体
WO2013008825A1 (ja) 2011-07-11 2013-01-17 株式会社トクヤマ フォトクロミック硬化性組成物
JP2013524300A (ja) * 2010-04-15 2013-06-17 オークリー インコーポレイテッド 彩度を増強されたアイウェア
WO2017189700A1 (en) * 2016-04-26 2017-11-02 The Regents Of The University Of California Negative photochromic materials with tunable properties
CN108929595A (zh) * 2018-08-13 2018-12-04 电子科技大学 一种隐形墨水组合物、隐形墨水组合物的制备方法及其应用
CN111849248A (zh) * 2020-07-13 2020-10-30 电子科技大学 一种光敏变色防伪条形码及其制备方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014136804A1 (ja) 2013-03-04 2014-09-12 株式会社トクヤマ フォトクロミック硬化性組成物、その硬化体及びその硬化体を含む積層体

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010204383A (ja) * 2009-03-03 2010-09-16 Idemitsu Kosan Co Ltd 赤色強調眼鏡及びゴーグル用樹脂成形体
JP2013524300A (ja) * 2010-04-15 2013-06-17 オークリー インコーポレイテッド 彩度を増強されたアイウェア
WO2013008825A1 (ja) 2011-07-11 2013-01-17 株式会社トクヤマ フォトクロミック硬化性組成物
WO2017189700A1 (en) * 2016-04-26 2017-11-02 The Regents Of The University Of California Negative photochromic materials with tunable properties
CN108929595A (zh) * 2018-08-13 2018-12-04 电子科技大学 一种隐形墨水组合物、隐形墨水组合物的制备方法及其应用
CN111849248A (zh) * 2020-07-13 2020-10-30 电子科技大学 一种光敏变色防伪条形码及其制备方法

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
HEMMER ET AL.: "Tunable Visible and Near Infrared Photoswitches", J. AM. CHEM. SOC., 2016
MELMY ET AL.: "Photoswitching Using Visible Light: A New Class of Organic Photochromic Molecules", J. AM. CHEM. SOC., 2014

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2025004856A1 (ja) * 2023-06-30 2025-01-02 株式会社ニコン・エシロール 組成物、眼鏡レンズ

Also Published As

Publication number Publication date
EP4542287A1 (en) 2025-04-23
JPWO2023243675A1 (https=) 2023-12-21
JP7830643B2 (ja) 2026-03-16
CN119301511A (zh) 2025-01-10
US20250116884A1 (en) 2025-04-10

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