US20110058142A1 - Optical Article Comprising a Double-Layer Abrasion and Scratch Resistant Coating and Method for Production Thereof - Google Patents

Optical Article Comprising a Double-Layer Abrasion and Scratch Resistant Coating and Method for Production Thereof Download PDF

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Publication number
US20110058142A1
US20110058142A1 US12/160,587 US16058707A US2011058142A1 US 20110058142 A1 US20110058142 A1 US 20110058142A1 US 16058707 A US16058707 A US 16058707A US 2011058142 A1 US2011058142 A1 US 2011058142A1
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US
United States
Prior art keywords
layer
groups
composition
resistant
abrasion
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.)
Abandoned
Application number
US12/160,587
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English (en)
Inventor
Fabien Berit-Debat
Christian Bovet
Jean-Paul Cano
Amelie Kudla
Yves Leclaire
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.)
EssilorLuxottica SA
Original Assignee
Essilor International Compagnie Generale dOptique SA
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 Essilor International Compagnie Generale dOptique SA filed Critical Essilor International Compagnie Generale dOptique SA
Assigned to ESSILOR INTERNATIONAL COMPAGNIE GENERALE D'OPTIQUE reassignment ESSILOR INTERNATIONAL COMPAGNIE GENERALE D'OPTIQUE ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: KUDLA, AMELIE, LECLAIRE, YVES, BOVET, CHRISTIAN, CANO, JEAN-PAUL, BERIT-DEBAT, FABIEN
Publication of US20110058142A1 publication Critical patent/US20110058142A1/en
Abandoned legal-status Critical Current

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Classifications

    • G02B1/105
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B05SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05DPROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/02Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by baking
    • B05D3/0254After-treatment
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B05SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05DPROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
    • B05D7/50Multilayers
    • B05D7/52Two layers
    • B05D7/54No clear coat specified
    • B05D7/546No clear coat specified each layer being cured, at least partially, separately
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING 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
    • C09D183/00Coating compositions based on 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; Coating compositions based on derivatives of such polymers
    • C09D183/04Polysiloxanes
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/10Optical coatings produced by application to, or surface treatment of, optical elements
    • G02B1/14Protective coatings, e.g. hard coatings
    • 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
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/24Structurally defined web or sheet [e.g., overall dimension, etc.]
    • Y10T428/24942Structurally defined web or sheet [e.g., overall dimension, etc.] including components having same physical characteristic in differing degree
    • Y10T428/2495Thickness [relative or absolute]
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/26Web or sheet containing structurally defined element or component, the element or component having a specified physical dimension
    • Y10T428/263Coating layer not in excess of 5 mils thick or equivalent
    • Y10T428/264Up to 3 mils
    • Y10T428/2651 mil or less
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/31504Composite [nonstructural laminate]
    • Y10T428/31511Of epoxy ether

Definitions

  • a coating that is “on” a substrate or that has been deposited “onto” a substrate is defined as being a coating (i) that is positioned above the substrate, (ii) that is not necessarily in contact with the substrate, which means that one or more intermediate coating(s) may be arranged between the substrate and the coating of interest, and (iii) that does not necessarily totally cover the substrate.
  • PC polycarbonate
  • Polycarbonates are commercially available and are marketed for example by GENERAL ELECTRIC COMPANY under the trade name LEXAN®, by TEIJIN under the trade name PANLITE®, by BAYER under the trade name BAYBLEND®, by MOBAY CHEMICHAL Corp. under the trade name MAKROLON® and by DOW CHEMICAL Co. under the trade name CALIBRE®.
  • the bilayered scratch-resistant and abrasion-resistant coating may be deposited directly onto a bare substrate.
  • the substrate main surface be coated with one or more functional coating(s) prior to depositing the abrasion-resistant coating of the invention.
  • These functional coatings may be, without limitation, an impact-resistant primer layer, a polarized coating, a photochromic coating, an antistatic coating, an additional abrasion-resistant and/or scratch-resistant coating or a coloured coating.
  • Curing catalysts do particularly act on the polymerization of the epoxy functions and do favour the action of the condensation catalysts.
  • the compounds that can be employed encompass the imidazole derivatives and their imidazolium salts, N-cyanoguanidine (H 2 NC( ⁇ NH)NHCN, cyanamide dimer), also known under the name dicyandiamide, acetylacetone metallic salts of formula M(CH 3 COCHCOCH 3 ) n , wherein M is a metallic ion, preferably Zn 2+ , Co 3+ , Fe 3+ or Cr 3+ , and n is an integer ranging typically from 1 to 3, preferably corresponding to the metal M oxidation level, ammonium tetrathiocyanatodiamine chromate(III) NH 4 [Cr(SCN) 4 (NH 3 ) 2 ], also known under the name Reinecke salt, compounds based on aluminium, metal-based carboxylates such as zinc, titanium, zirconium, tin or magnesium, for
  • Curing and condensation catalysts are used in usual amounts in order to obtain the condensation and the hardening of the compositions of the invention within a time period of about a few hours at temperatures of about 100° C.
  • Curing catalysts are typically used in an amount ranging from 0 to 5% by weight as related to the total weight of the upper (or lower) layer composition, preferably from 0.1 to 3%.
  • Condensation catalysts are typically used in an amount ranging from 0 to 10% by weight as related to the total weight of the upper (or lower) layer composition, preferably from 0 to 8%.
  • the “theoretical dry matter weight of component I, II, III or IV” means:
  • the upper and lower abrasion-resistant layer compositions of the invention may contain in some embodiments the same compound categories, but they are different as regards the contents of their components.
  • the theoretical dry matter weight of compounds I represents preferably from 30 to 60% of the upper layer composition dry matter weight, more preferably from 40 to 55%.
  • the theoretical dry matter weight of compounds II represents preferably from 30 to 60% of the upper layer composition dry matter weight, more preferably from 40 to 55%.
  • the sum of the theoretical dry matter weights of compounds I and II represents preferably at least 75% of the lower layer composition dry matter weight, more preferably at least 80%, even more preferably at least 85%.
  • the upper layer composition dry matter weight represents preferably from 5 to 40%, more preferably from 15 to 25% by weight, as related to the total weight of the composition.
  • the sum of the weights of compounds I and II represents preferably from 25 to 65% of the upper layer composition weight, preferably from 30 to 60%, more preferably from 35 to 55%.
  • the weight ratio of compounds I to compounds II in this composition does preferably range from 0.25 to 0.60, more preferably from 0.30 to 0.60, and even more preferably from 0.35 to 0.45.
  • the theoretical dry matter weight of the lower layer composition represents preferably from 10 to 50%, more preferably from 25 to 40% by weight, as related to the total weight of the composition.
  • M′′ represents a metal or a metalloid
  • Z′′ groups being the same or different, are hydrolyzable groups and z, equal to or higher than 4, preferably from 4 to 6, is the metal or metalloid M′′ valence, the ratio:
  • antireflective coatings are preferably, multilayered coatings comprising high refractive index (HI) layers and low refractive index (LI) layers, alternately.
  • the LI layers of the antireflective coating comprise a mixture of SiO 2 and Al 2 O 3 .
  • a layer of an antireflective stack is said to be a high refractive index layer when its refractive index is higher than 1.55, preferably higher than or equal to 1.6, more preferably higher than or equal to 1.8 and even more preferably higher than or equal to 2.0.
  • a layer of an antireflective stack is said to be a low refractive index layer when its refractive index is lower than or equal to 1.55, preferably lower than or equal to 1.50, more preferably lower than or equal to 1.45.
  • the antireflective coating is typically applied by vacuum deposition according to any of following procedures: i) by evaporation, optionally ion beam assisted; ii) by ion beam sputtering; iii) by cathode sputtering; iv) by plasma-assisted chemical vapour deposition.
  • an antireflective coating comprising a stack exclusively comprising mineral dielectric layers is preferred. It does preferably comprise a stack of at least three dielectric layers with high refractive index and low refractive index layers, alternately.
  • an optical article of the invention comprises a substrate successively coated with an impact-resistant primer layer, the bilayered scratch-resistant and abrasion-resistant coating of the invention, an antireflective stack and a hydrophobic and/or oleophobic coating.
  • the article of the invention is preferably an optical lens, more preferably an ophthalmic lens for spectacles, or an optical or ophthalmic lens blank.
  • the lens may be a polarized lens or a photochromic lens.
  • an optical article comprising a substrate having at least one main surface
  • the optical article comprising a substrate onto which the abrasion- and scratch-resistant coating of the invention has been formed may also be a temporary support, onto which said coating is stored, waiting for being transferred to another substrate, which is typically the final substrate, such as a substrate for an ophthalmic lens.
  • the lower layer and the upper layer of the bilayered coating should be deposited onto the temporary support in reverse order as compared to the expected stacking order on the final support.
  • thermoplastic (co)polymers that can be suitably used for making the temporary support encompass polysulfones, aliphatic poly(meth)acrylates, such as methyl poly(meth)acrylate, polyethylene, polypropylene, polystyrene, SBM bloc copolymers (styrene, butadiene and methyl methacrylate), polyphenylene sulfide (PPS), arylene polyoxides, polyimides, polyesters, polycarbonates such as bisphenol A polycarbonate, polyvinyl chloride, polyamides such as nylons, their copolymers and mixtures thereof. Polycarbonate is the preferred thermoplastic material.
  • further functional coatings may be formed on the lower layer of the bilayered coating prior to conducting the transfer.
  • This composition is obtained by mixing the components mentioned in the table hereunder.
  • the resulting layer has a high refractive index because of the titanium-based colloid.
  • the substrate for the ophthalmic lens ORMA® was coated by being dip coated with a 8 ⁇ m-thick impact-resistant primer layer, prepolymerized for 30 minutes at 90° C.
  • a substrate for an ophthalmic lens ORMA® was coated by being dip coated with a lower layer composition.
  • the dewetting rate of these lenses was adjusted in such a way that the deposited thickness be of 2.5 ⁇ m.
  • the lower layer composition was then prepolymerized in an oven for 30 min at 100° C.
  • the lens was cooled for 15 minutes at room temperature and was then directly coated by being dip coated with an abrasion-resistant and/or scratch-resistant coating additional layer (the dewetting rate of the lens being adjusted in such a way that the deposited thickness be of 1 ⁇ m), such a deposition being followed with a polymerisation final step of the whole, that was conducted at 90° C. for 30 minutes.
  • the abrasion resistance was measured by means of the value obtained in the BAYER ISTM test, the scratch resistance using a steel wool test, and the abrasion-resistant coating adhesion using the “cross-hatch test”.
  • Obtaining a high value in the BAYER ISTM test is an indication of a high level of abrasion resistance, whereas a low value in the steel wool test is an indication of a high level of scratch resistance.
  • the abrasion resistance was evaluated by determining the BAYER ISTM values for substrates coated with the abrasion-resistant coating of the invention or with a comparative abrasion-resistant coating, for substrates coated with the abrasion-resistant coating of the invention and with an antireflective coating (examples 1, 2, 4, 5), for substrates coated with a primer coating and with the abrasion-resistant coating of the invention (examples 15, 19, 21, 22), for substrates coated with an additional abrasion-resistant and/or scratch-resistant coating and with the abrasion-resistant bilayered coating of the invention (example 18), or for substrates coated with the abrasion-resistant bilayered coating of the invention and with a supplementary abrasion-resistant and/or scratch-resistant coating layer (example 20).
  • the scratch resistance was measured by using the steel wool test which did consist in performing 5 forward and back motions by rubbing with the hand along 4-5 cm the face of a glass coated according to the invention with a steel wool, in the fiber direction, while applying a constant pressure on the steel wool during this operation (5 k g forward, 2.5 k g back).
  • a piece of about 3 cm ⁇ 3 cm of extra fine steel wool STARWAX (grade 000) folded upon itself was used.
  • the adhesion test was made based on the ASTM D3359-93 standard and resulted in a qualitative ordering ranging from 0 to 5, 0 being the best result.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Ophthalmology & Optometry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Laminated Bodies (AREA)
  • Surface Treatment Of Optical Elements (AREA)
  • Eyeglasses (AREA)
  • Surface Treatment Of Glass (AREA)
  • Epoxy Resins (AREA)
  • Paints Or Removers (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Silicon Polymers (AREA)
  • Wrappers (AREA)
  • Decoration By Transfer Pictures (AREA)
US12/160,587 2006-11-23 2007-11-22 Optical Article Comprising a Double-Layer Abrasion and Scratch Resistant Coating and Method for Production Thereof Abandoned US20110058142A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0655085 2006-11-23
FR0655085A FR2909187B1 (fr) 2006-11-23 2006-11-23 Article d'optique comportant un revetement anti-abrasion et anti-rayures bicouche, et procede de fabrication
PCT/FR2007/052383 WO2008062142A1 (fr) 2006-11-23 2007-11-22 Article d'optique comportant un revetement anti-abrasion et anti-rayures bicouche, et procede de fabrication

Related Parent Applications (1)

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US (2) US20110058142A1 (cg-RX-API-DMAC7.html)
EP (1) EP2092377B1 (cg-RX-API-DMAC7.html)
JP (1) JP4918101B2 (cg-RX-API-DMAC7.html)
CN (1) CN101553743B (cg-RX-API-DMAC7.html)
AT (1) ATE545051T1 (cg-RX-API-DMAC7.html)
BR (1) BRPI0718835B1 (cg-RX-API-DMAC7.html)
ES (1) ES2382008T3 (cg-RX-API-DMAC7.html)
FR (1) FR2909187B1 (cg-RX-API-DMAC7.html)
PL (1) PL2092377T3 (cg-RX-API-DMAC7.html)
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US20130293835A1 (en) * 2012-05-04 2013-11-07 Essilor Internatinal (Compagnie Generale D'Optique D'Optique) Abrasion-resistant film and ophthalmic lens containing same
US20140106163A1 (en) * 2011-07-01 2014-04-17 Essilor International (Compagnie Generale D'optique) Optical article including an antireflection coating having improved crack-resistance properties under mechanical stress
WO2014078497A1 (en) * 2012-11-16 2014-05-22 Liquipel Ip Llc Apparatus and methods for plasma enhanced chemical vapor deposition of dielectric/polymer coatings
EP2801846A1 (de) * 2013-05-06 2014-11-12 Carl Zeiss Vision International GmbH Optisches Element mit einer Beschichtung hoher Diffusivität
US20150024212A1 (en) * 2013-07-22 2015-01-22 Itoh Optical Industrial Co., Ltd. Hard coating composition
US20150024925A1 (en) * 2012-02-28 2015-01-22 Bluescope Steel Limited Protective coating compositions for photocatalytic layers on substrates
US20150277152A1 (en) * 2012-11-09 2015-10-01 Essilor International (Compagnie Generale D'optique) Optical article comprising a precursor coating of an anti-fog coating and a temporary layer made of metal fluorides or compounds including magnesium and oxygen
EP3327091A1 (en) 2016-11-23 2018-05-30 Essilor International Epoxy functional composition protecting dyes from photo-degradation and cured coatings prepared therefrom
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US20180251675A1 (en) * 2017-03-01 2018-09-06 Younger Mfg. Co. Dba Younger Optics Optical articles comprising photochromic poly(urea-urethane)
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EP3489270A1 (en) 2017-11-28 2019-05-29 Essilor International (Compagnie Generale D'optique) Heat-curable hybrid epoxy functional composition and transparent heat-cured abrasion-resistant coatings prepared therefrom
EP3632950A1 (en) 2018-10-05 2020-04-08 Essilor International Storage-stable heat-curable hybrid epoxy functional composition and transparent heat-cured coatings prepared therefrom
US10683433B2 (en) * 2014-10-29 2020-06-16 Ppg Industries Ohio, Inc. Protective coating system for plastic substrate
US10723915B2 (en) 2018-11-26 2020-07-28 Itoh Optical Industrial Co., Ltd. Hard coating composition
US20210130545A1 (en) * 2017-08-17 2021-05-06 Shin-Etsu Chemical Co., Ltd. Water-repellent member and method for manufacturing water-repellent member
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US11512818B2 (en) 2020-07-10 2022-11-29 Junming Ding Multi-mode portable lighting device with novel battery charging unit
US20230148164A1 (en) * 2020-04-23 2023-05-11 Essilor International Water based anti-abrasion coating
US12022583B2 (en) 2020-07-10 2024-06-25 Asiatelco Technologies, Inc. Portable devices, systems and methods with automated heat control assembly
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FR2985255B1 (fr) 2011-12-28 2015-08-07 Ecole Polytech Article revetu d'un revetement interferentiel ayant des proprietes stables dans le temps.
JP2016056025A (ja) * 2013-01-29 2016-04-21 オーエムジー株式会社 光学ガラスフィルタ
US9110230B2 (en) 2013-05-07 2015-08-18 Corning Incorporated Scratch-resistant articles with retained optical properties
FR3007024A1 (fr) 2013-06-14 2014-12-19 Essilor Int Article revetu d'une couche de nature silico-organique ameliorant les performances d'un revetement externe
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FR3039786B1 (fr) 2015-08-05 2017-09-29 Essilor Int Procede de lamination d'un revetement interferentiel comportant une couche de nature organique-inorganique et article ainsi obtenu
FR3039828B1 (fr) 2015-08-05 2021-12-17 Essilor Int Article a proprietes thermomecaniques ameliorees comportant une couche de nature organique-inorganique
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FR3045672B1 (fr) 2015-12-18 2018-03-16 Corporation De L'ecole Polytechnique De Montreal Article comprenant une couche organique-inorganique de bas indice de refraction
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EP3287818B1 (en) 2016-08-23 2020-11-11 Corporation de L'Ecole Polytechnique de Montreal Ophthalmic lens having increased resistance to hot and humid environment
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WO2018198937A1 (ja) * 2017-04-27 2018-11-01 日本板硝子株式会社 被膜付き透明基板、被膜付き透明基板の被膜を形成するための塗工液及び被膜付き透明基板の製造方法
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ATE545051T1 (de) 2012-02-15
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FR2909187A1 (fr) 2008-05-30
CN101553743A (zh) 2009-10-07
PL2092377T3 (pl) 2012-07-31
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US20170003420A1 (en) 2017-01-05
US10222511B2 (en) 2019-03-05

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