WO1992021492A1 - Article en verre resistant a l'humidite - Google Patents

Article en verre resistant a l'humidite Download PDF

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Publication number
WO1992021492A1
WO1992021492A1 PCT/US1992/003414 US9203414W WO9221492A1 WO 1992021492 A1 WO1992021492 A1 WO 1992021492A1 US 9203414 W US9203414 W US 9203414W WO 9221492 A1 WO9221492 A1 WO 9221492A1
Authority
WO
WIPO (PCT)
Prior art keywords
weight percent
meth
acrylate
monomer
group
Prior art date
Application number
PCT/US1992/003414
Other languages
English (en)
Inventor
Wells C. Cunningham
Kenneth L. Crouse
Original Assignee
Advanced Glass Treatment Systems
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 Advanced Glass Treatment Systems filed Critical Advanced Glass Treatment Systems
Publication of WO1992021492A1 publication Critical patent/WO1992021492A1/fr

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Classifications

    • 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
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • 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
    • B32B17/10018—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 only one glass sheet
    • C—CHEMISTRY; METALLURGY
    • C03—GLASS; MINERAL OR SLAG WOOL
    • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
    • C03C17/28—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material
    • C03C17/32—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material with synthetic or natural resins

Definitions

  • the present invention relates to strength
  • Coatings intended to contain glass fragments from fractured glass bottles are also known.
  • a method for increasing the strength of glass containers which ostensibly allows a reduction in container mass is described in U.S. Patent Nos.
  • Hashimoto et al (Hashimoto et al '976).
  • the method of Hashimoto et al comprises applying a reactive coating material to a glass container treated with a silane coupling agent or applying a mixture of the coating material and the silane coupling agent to the glass container and then irradiating the coated container to cure the coating.
  • Hashimoto et al demonstrate an increase in the strength of a container under dry conditions. Hashimoto et al also address short term exposure to "severe
  • the container comprises a glass substrate and a coating layer, comprising the cured reaction product of a reactive liquid coating composition, coating a surface of the substrate.
  • the coating composition comprises:
  • (meth)acryloyl groups per molecule from about 5 weight percent to about 50 weight percent of a crosslinking monomer having at least three (meth)acryloyl groups per molecule; from about 20 weight percent to about 60 weight percent of a fluorinated (meth) acrylate monomer; from about 1 weight percent to about 30 weight percent of an organosilane monomer having one or more
  • a process for increasing the humidity resistance of a glass substrate is disclosed. The process
  • the layer of coating composition is cured by irradiating the coated
  • the glass substrate of the present invention may comprise any silica based glass, e.g. borosilicate, soda-lime-silica or quartz glass.
  • the glass substrate comprises soda-lime-silica glass.
  • the coating composition and process set forth herein may also be used to increase the resistance of other glass substrates to moisture driven degradation of the tensile and/or flexural strength of the substrate to thereby produce moisture resistant glass articles, e.g. optical fibers, fluorescent lighting tubes, CRT tubes, automobile windshields, and glass sheets, other than glass containers.
  • moisture resistant glass articles e.g. optical fibers, fluorescent lighting tubes, CRT tubes, automobile windshields, and glass sheets, other than glass containers.
  • the film forming monomer may be any reactive liquid monomer having two (meth)acryloyl groups per molecule.
  • (meth) acrylate as used herein signifies that either the methacrylate or the acrylate form of the compound may be used
  • Suitable film forming di (meth) acrylate monomers include, e.g. di (meth) acrylic esters and di(meth)acrylamides.
  • di (meth) acrylic esters of alkyl diols di (meth) acrylic esters of dicarboxylic acids, di(meth)acrylamides of diamino compounds and mixtures thereof.
  • suitable film forming di (meth) acrylate monomers include ethylene glycol di (meth) acrylate, diethylene glycol di(meth)acrylate, triethyleneglycol di (meth) acrylate, polyethyleneglycol di (meth) acrylate, propylene glycol di (meth) acrylate, dipropylene glycol di(meth) acrylate
  • tripropyleneglycol di(meth)acrylate tripropyleneglycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1, 3 butanediol di(meth)acrylate, 1, 4 butanediol di(meth)acrylate, 1, 6 hexanediol
  • the coating material of the present invention may include from about 10 weight percent to about 74 weight percent of the film forming monomer. Preferably, the coating material of the present invention includes from about 20 weight percent to about 66 weight percent of the film forming monomer.
  • the crosslinking monomer may by any reactive liquid monomer having three or more (meth)acryloyl groups per molecule.
  • Suitable crosslinking monomers include, e.g. (meth)acrylic esters of polyhydric
  • (meth)acrylic functional groups and mixtures thereof.
  • (Meth)acrylic esters of polyhydric alcohols having an MW less than about 550 are preferred as the
  • crosslinking monomer examples include trimethylolpropane
  • ditrimethylolpropane tetra(meth)acrylate dipentaerythritol hexa (meth)acrylate, tri (meth)acrylate of tris(2-hydroxyethyl) isocyanurate and N, N', N" , N" ' terephthallylidenetetraacrylamide.
  • crosslinking monomer preferred as the crosslinking monomer.
  • the coating material of the present invention may include from about 5 weight percent to about 50 weight percent of the crosslinking monomer. Preferably, the coating material of the present invention includes from about 10 weight percent to about 40 weight percent of the crosslinking monomer.
  • a coating composition according to the present invention satisfies a further constraint wherein the combined weight of diacrylate film forming monomer and acrylate crosslinking monomer monoacrylate should not exceed 60% of the total weight of the coating composition. If the combined weight of the difunctional film forming monomer and the
  • polyfunctional crosslinking monomer monoacrylate exceed 60 % of the coating composition, the excess amount should be selected from the group consisting of
  • dimethacrylate film forming monomers dimethacrylate film forming monomers, methacrylate crosslinking monomers and mixtures thereof.
  • the fluorinated (meth)acrylate monomer of the prhsent invention may be a fluorinated
  • the fluorinated mono(meth)acrylate monomer of the present invention may be any fluorinated
  • mono(meth)acrylate monomer e.g. mono(meth)acrylate monomers having fluorine substituted alkyl, cycloalkyl, or alkoxy groups and having no fluorine atoms at the alpha carbon atom.
  • mono(meth)acrylate monomers having fluorine substituted alkyl, cycloalkyl, or alkoxy groups and having no fluorine atoms at the alpha carbon atom.
  • mono(meth)acrylic monomers include:
  • R H or CH 3
  • R H or CH 3
  • Preferred fluorinated mono(meth)acrylates include 1,1 dihydroperfluorobutyl(meth)acrylate, 1,1,5
  • the fluorinated di (meth)acrylate monomer of the present invention may be any fluorinated
  • di (meth)acrylate monomers include; e.g.
  • R H or CH 3 ,
  • n 1 to 26 ;
  • di(meth)acrylate monomer of the present invention comprises a perfluoropoly-etherdiacrylate having a molecular weight between about 1100 and about 2000.
  • the fluorinated acrylate monomers of the present invention provide a very significant and unexpected advantage in that they may be included in the coating composition in relatively high amounts, thereby
  • the fluorinated acrylate monomer of the present invention provides an unexpectedly rapid cure speed.
  • the coating composition of the resent invention is cured by a free radical
  • fluorinated acrylate monomers of the present invention than in their corresponding non-fluorinated analogs, substitution of a fluorinated monomer for its
  • substitution of a fluorinated acrylic monomer for a non-fluorinated acrylate monomer is not detrimental to the cure speed, but tends, unexpectedly, to increase the cure speed of the coating composition.
  • the coating material of the present invention may include from about 20 weight percent to about 60 weight percent of the fluorinated (meth)acrylate monomer.
  • the coating material of the present invention is not limited to the coating material of the present
  • invention includes from about 20 weight percent to about 46 weight percent of the fluorinated
  • the organosilane coupling agent of the coating composition of the present invention may be any organic radical having the organosilane coupling agent of the coating composition of the present invention.
  • organosilane monomer having one or more groups capable of reacting with the glass substrate and a
  • organosilane coupling agents are those of the general formula:
  • R is a nonhydrolyzable organic functional group which is capable of reacting with a
  • (meth)acryloyl group e.g. (meth)acryloxyalkyl, vinyl, allyl, mercaptoalkyl or aminoalkyl
  • R' is a nonhydrolyzable nonfunctional organic group, e.g. alkyl
  • X is a hydroxyl group or hydrolyzable group, e.g. alkoxy, acetoxy, amino or halo, and
  • n 0, 1 or 2.
  • the hydroxyl or hydrolyzable group X is capable of undergoing reaction with, or of undergoing hydrolysis and subsequent reaction with, silanol groups on the glass substrate to chemically bond the organosilane monomer to the surface of the glass substrate.
  • the nonhydrolyzable organic functional group is capable of undergoing reaction with a (meth)acryloyl group of the coating monomers to chemically bond the organosilane monomer within the coating layer.
  • n 0 or 1
  • the organic functional group R is a group capable of undergoing free radical polymerization and the hydrolyzable group X is alkoxy.
  • the organic functional group R is (meth)acryloxyalkyl
  • the nonfunctional organic group R' is methyl or ethyl
  • the hydrolyzable group X is methoxy or ethoxy.
  • suitable organosilane coupling agents include
  • methacryloxypropylmethyldiethoxysilane are particularly preferred as the organosilane.
  • organosilane coupling agents Mixtures of two or more organosilane coupling agents are also suitable as the organosilane coupling agent.
  • the coating material of the present invention may include from about 1 weight percent to about 30 weight percent of the organosilane. Preferably, the coating material of the present invention includes from about 5 weight percent to about 20 weight percent of the organosilane.
  • the polymerization initiator of the coating composition of the present invention is preferably a photoinitiator which dissociates or decomposes upon exposure to radiation to yield a free radical.
  • Photoinitiators which dissociate upon exposure radiation having a wavelength in the range of 40 nm to 400 nm are
  • Suitable photoinitiator compounds include, e.g. benzil, benzophenone, camphorquinone, benzoin n-butyl ether, thioxanthone,
  • Preferred photoinitiators include 2-hydroxy-2-methyl-1-phenyl-propan-1-one and 1-hydroxycyclohexylphenylketone.
  • the coating material of the present invention may be heat cured by including a thermal initiator, i.e. a compound which decomposes upon heating to yield free radical, in the coating
  • the thermal initiator may be substituted for the photoinitiator to provide heat curable
  • thermal initiators include, e.g. 2, 2 '-azobis (2, 4
  • the coating material of the present invention may include any effective amount of the polymerization initiator.
  • the coating material of the present invention includes from about 5 weight percent to about 20 weight percent of the polymerization initiator.
  • the polymerization initiator may be omitted from the coating composition, e.g. if the composition is to be cured by exposure to an electron beam.
  • the coating composition of the present invention is made by combining the various components of the composition and agitating the resultant combination to form a homogenous mixture.
  • a layer of reactive liquid coating composition is applied to the glass substrate by any convenient method, e.g. dipping, spray coating, flow coating or roll coating.
  • the coating composition may be diluted with a suitable solvent, e.g. methylethylketone,
  • tetrahydrofuran and various additives known in the art, e.g. leveling agents, surfactants, may be added to the coating composition in accord with the demands of the particular application method.
  • leveling agents e.g. leveling agents, surfactants
  • a layer of reactive liquid coating having a thickness of between 0.3 um and 30 urn is applied to a surface of the container.
  • the layer is between 1 um and 10 um thick.
  • a solventless layer of the reactive coating composition is applied by roll coating.
  • the reactive coating composition is applied to the entire exterior surface of the container.
  • the coating composition may be applied only to those surfaces of the container that are most likely to be damaged, e.g. the circumferential surfaces of a cylindrical container.
  • the coating composition is applied to the container within several hours of heat treating the container as described in copending, coassigned U. S. Application No. 537,507 entitled “Method for Enhancing Strength of A Glass Container and Strength Enhanced Glass Container” by W. C. Cunningham et al.
  • the '507 application describes a method for
  • the coating step may be carried out at any combination of the following features: (1) a temperature near the annealing temperature of the glass, e.g. above about 500 oC, applying a polymerizable coating composition to the heat treated container, preferably within six hours after the heat treatment, and curing the coating.
  • the coating step may be carried out at any combination of the following features:
  • the coating step is carried out at a temperature between about 15°C and about 35°C.
  • the layer of coating composition is cured by exposing the coated container to high
  • Suitable sources of high intensity UV radiation include, e.g. medium pressure mercury vapor lamps and high pressure mercury vapor lamps.
  • the speed with which a coating composition may be cured is an important variable with regard to the practical application of the process of the present invention.
  • the speed at which a given composition may be cured depends upon several variables, i.e. coating thickness, ambient O 2 concentration and the intensity of the radiation to which the composition is exposed.
  • the intensity of the radiation and the duration of the exposure are chosen to fully cure the exterior surface of the coating, i.e. to provide a "tack free" surface at the interface between the coating and the surrounding atmosphere.
  • the coated surface of the container is exposed in air to UV radiation having an intensity of greater than about 200 mW/cm 2 at a wavelength of between about 200 and about 450 nm for a time period between 0.1 second and 100 seconds.
  • oxygen has an inhibitory effect on the free radical polymerization reaction and consequently the presence of oxygen tends to decrease the speed of cure.
  • composition at a given intensity of radiation may be enhanced by carrying out the curing step in an inert, e.g. N 2 atmosphere.
  • an inert e.g. N 2 atmosphere.
  • Soda-lime silica microscope slides (nominally 1" ⁇
  • the coated slides were aligned in a rack and cured by passing the rack under a FUSION SYSTEMS 300 WPI "H bulb” high pressure mercury lamp.
  • the flawed side of each slide was alternately oriented upwardly and downwardly with the successive passes.
  • the slides were subjected to UV radiation at an intensity of about 550 mW/cm 2 for 1 second per pass. The number of passes required to obtain a tackfree coating was recorded for each side.
  • the coated slides were either stored under ambient conditions or soaked in distilled water overnight prior to testing.
  • the slides were tested in a INSTRON 1122 testing apparatus using a 4 point bend flexural test fixture with a span ratio of 2 and a crosshead speed of 0.2 in/min with the flawed side of the slide in tension.
  • the strength enhancement (S.E.) ratio is
  • Enhancement values were derived by testing coated slides that had been stored under ambient conditions and tested under ambient conditions. "High Humidity" strength enhancement values were derived by testing coated slides that had been stored submerged overnight in water and tested wet at room temperature. Five to twenty five samples were tested for each coating composition. Results are expressed as arithmetic averages.
  • compositions tested included 10 weight percent crosslinking monomer (trimethylolpropane triacrylate), 14 weight percent organosilane monomer (3-methacryloxypropyltrimethoxysilane) and 6 weight percent photoinitiator (2-hydroxy- 2-methyl-1-phenyl-propan-1-one).
  • weight percent crosslinking monomer trimethylolpropane triacrylate
  • organosilane monomer 3-methacryloxypropyltrimethoxysilane
  • photoinitiator 2-hydroxy- 2-methyl-1-phenyl-propan-1-one
  • compositions tested were applied to microscope slides, cured and tested according to the procedure set forth in EXAMPLE 1.
  • compositions included 14 weight percent organosilane monomer
  • non-fluorinated monomer exhibit increased cure speed while maintaining a high strength enhancement ratio under humid conditions.
  • results also indicate that, unlike non-fluorinated acrylate and methacrylate monomers there is no substantial difference in cure speed between a composition which includes a
  • composition which includes a fluorinated
  • alkyl (meth)acrylate monomer and a composition in which an analogous fluorinated compound having a longer carbon chain length has been substituted.
  • composition of the present invention included 10 weight percent
  • crosslinking monomer (trimethylolpropanetriacrylate), 14 weight percent organosilane monomer
  • Comparative formulation 1 (CF1), corresponding to Example 33 of the Hashimoto et al patents, included (by parts):
  • Comparative formulation 5 (CF5), corresponding to Example 69 of the Hashimoto et al patents, included (by parts) :
  • Comparative formulation 6 corresponding to Example 70 of the Hashimoto et al patents, and included (by parts) :
  • Example 1 60°C for one minute to evaporate the solvent, cured and then tested under ambient and under high humidity conditions according to the procedure set forth in Example 1 above.
  • the slides were coated under ambient conditions (about 21°C and about 23 % relative humidity).
  • compositions of the present invention are, in all cases,

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Geochemistry & Mineralogy (AREA)
  • Paints Or Removers (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)

Abstract

Article en verre ayant une résistance améliorée à la perte de solidité causée par l'humidité comprenant un substrat en verre et une couche consistuée d'une composition de revêtement réactif vulcanisé déposée sur une surface du substrat. La composition de revêtement réactif comprend entre environ 10 pourcent en poids et environ 74 pourcent en poids d'un monomère formant une pellicule comptant deux groupes (meth)acryloyle par molécule; entre environ 5 pourcent en poids et environ 50 pourcent en poids d'un monomère de réticulation réactif comptant au moins 3 groupes (meth)acryloyle par molécule; entre environ 20 pourcent en poids et environ 60 pourcent en poids d'un monomère (meth)acrylate fluoré; entre environ 1 pourcent en poids et environ 30 pourcent en poids d'un monomère organosilane comptant un ou plusieurs groupes fonctionnels capables de réagir avec le substrat de verre et comptant un groupe fonctionnel organique non hydrolysable capable de réagir avec un groupe meth(acryloyle) et une quantité efficace d'un composé initiateur de polymérisation. Une méthode permettant d'accroître la résistance d'un article en verre à la perte de solidité causée par l'humidité consiste à appliquer une couche de la composition de revêtement réactif décrite ci-dessus et à vulcaniser cette couche, de préférence en irradiant l'article revêtu avec un rayonnement UV de haute intensité.
PCT/US1992/003414 1991-05-31 1992-04-27 Article en verre resistant a l'humidite WO1992021492A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US70893191A 1991-05-31 1991-05-31
US708,931 1991-05-31

Publications (1)

Publication Number Publication Date
WO1992021492A1 true WO1992021492A1 (fr) 1992-12-10

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WO (1) WO1992021492A1 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0628614A1 (fr) * 1993-06-09 1994-12-14 Röhm Gmbh Matériau de revêtement résistant à l'abrasion à base d'acrylate
US5418304A (en) * 1993-06-09 1995-05-23 Roehm Gmbh Chemische Fabrik Scratch-resistant coating agent based on acrylates
USRE36294E (en) * 1993-06-09 1999-09-07 Rohm Gmbh Chemische Fabrik Scratch-resistant coating agent based on arcylates
WO2006073920A2 (fr) * 2004-12-30 2006-07-13 3M Innovative Properties Company Composants internes d'un dispositif optique comprenant un revetement dur
EP1700871A1 (fr) * 2005-03-10 2006-09-13 Nanogate Advanced Materials GmbH Composition à mouler pour préparer des éléments optiques de précision
US7173778B2 (en) 2004-05-07 2007-02-06 3M Innovative Properties Company Stain repellent optical hard coating
US7267850B2 (en) 2004-05-07 2007-09-11 3M Innovative Properties Company Article comprising fluorochemical surface layer
EP2239285A1 (fr) 2009-04-07 2010-10-13 Nanogate Advanced Materials GmbH Composition de formage
CN113698533A (zh) * 2021-08-31 2021-11-26 武汉羿阳科技有限公司 紫外固化树脂组合物、其制备的彩膜及彩膜在柔性oled封装结构中的应用
US11613596B2 (en) * 2017-06-30 2023-03-28 Fujifilm Corporation Composition, optical film, polarizing plate, display device, and method for producing composition

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4199421A (en) * 1977-02-23 1980-04-22 Mitsubishi Rayon Company, Limited Coating composition and a method for producing a synthetic resin molded product having an abrasion resistant surface
US4891241A (en) * 1987-04-28 1990-01-02 Dainippon Ink & Chemicals, Inc. Method of increasing the dynamical strength of glass container

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4199421A (en) * 1977-02-23 1980-04-22 Mitsubishi Rayon Company, Limited Coating composition and a method for producing a synthetic resin molded product having an abrasion resistant surface
US4891241A (en) * 1987-04-28 1990-01-02 Dainippon Ink & Chemicals, Inc. Method of increasing the dynamical strength of glass container

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5418304A (en) * 1993-06-09 1995-05-23 Roehm Gmbh Chemische Fabrik Scratch-resistant coating agent based on acrylates
USRE36294E (en) * 1993-06-09 1999-09-07 Rohm Gmbh Chemische Fabrik Scratch-resistant coating agent based on arcylates
EP0628614A1 (fr) * 1993-06-09 1994-12-14 Röhm Gmbh Matériau de revêtement résistant à l'abrasion à base d'acrylate
US7173778B2 (en) 2004-05-07 2007-02-06 3M Innovative Properties Company Stain repellent optical hard coating
US7332217B2 (en) 2004-05-07 2008-02-19 3M Innovative Properties Company Article and comprising fluorochemical surface layer
US7267850B2 (en) 2004-05-07 2007-09-11 3M Innovative Properties Company Article comprising fluorochemical surface layer
WO2006073920A2 (fr) * 2004-12-30 2006-07-13 3M Innovative Properties Company Composants internes d'un dispositif optique comprenant un revetement dur
WO2006073920A3 (fr) * 2004-12-30 2006-08-31 3M Innovative Properties Co Composants internes d'un dispositif optique comprenant un revetement dur
WO2006094997A1 (fr) * 2005-03-10 2006-09-14 Nanogate Advanced Materials Gmbh Composition de moulage pour la production d'optiques de precision
EP1700871A1 (fr) * 2005-03-10 2006-09-13 Nanogate Advanced Materials GmbH Composition à mouler pour préparer des éléments optiques de précision
US8246896B2 (en) 2005-03-10 2012-08-21 Nanogate Advance Materials Gmbh Impression composition for the preparation of precision optics
EP2239285A1 (fr) 2009-04-07 2010-10-13 Nanogate Advanced Materials GmbH Composition de formage
WO2010115672A1 (fr) 2009-04-07 2010-10-14 Nanogate Advanced Materials Gmbh Composition d'impression
US11613596B2 (en) * 2017-06-30 2023-03-28 Fujifilm Corporation Composition, optical film, polarizing plate, display device, and method for producing composition
CN113698533A (zh) * 2021-08-31 2021-11-26 武汉羿阳科技有限公司 紫外固化树脂组合物、其制备的彩膜及彩膜在柔性oled封装结构中的应用

Also Published As

Publication number Publication date
AU1927092A (en) 1993-01-08

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