EP1572819A1 - Composition silicone pour revetement dur, a base de silice colloidale, durcissable par voie cationique, antibuee et/ou antisalissures. - Google Patents
Composition silicone pour revetement dur, a base de silice colloidale, durcissable par voie cationique, antibuee et/ou antisalissures.Info
- Publication number
- EP1572819A1 EP1572819A1 EP03815084A EP03815084A EP1572819A1 EP 1572819 A1 EP1572819 A1 EP 1572819A1 EP 03815084 A EP03815084 A EP 03815084A EP 03815084 A EP03815084 A EP 03815084A EP 1572819 A1 EP1572819 A1 EP 1572819A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- formula
- crosslinkable
- oligomer
- composition according
- nhco
- 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.)
- Withdrawn
Links
Classifications
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N29/00—Investigating or analysing materials by the use of ultrasonic, sonic or infrasonic waves; Visualisation of the interior of objects by transmitting ultrasonic or sonic waves through the object
- G01N29/34—Generating the ultrasonic, sonic or infrasonic waves, e.g. electronic circuits specially adapted therefor
- G01N29/341—Generating the ultrasonic, sonic or infrasonic waves, e.g. electronic circuits specially adapted therefor with time characteristics
- G01N29/343—Generating the ultrasonic, sonic or infrasonic waves, e.g. electronic circuits specially adapted therefor with time characteristics pulse waves, e.g. particular sequence of pulses, bursts
-
- 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
- C09D183/00—Coating 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
- C09D183/04—Polysiloxanes
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- 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
- C09D183/00—Coating 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
- C09D183/04—Polysiloxanes
- C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
-
- 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
-
- 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
- G02B1/18—Coatings for keeping optical surfaces clean, e.g. hydrophobic or photo-catalytic films
-
- Y—GENERAL 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
Definitions
- the field of the present invention is that of compositions which can be crosslinked cationically in a scratch-resistant hard coating. More preferably, the present invention relates to compositions which can be crosslinked cationically with a hard coating, moreover having anti-fouling and / or anti-fogging properties.
- Thermoplastic materials such as polycarbonate, have taken a prominent place in many applications, as glass substitutes. This is the case, for example, in the automotive field, where they are used for the manufacture of lenses for headlight optics and rear lights of vehicles. This is also the case in the field of eyewear where they are used for the production of spectacle lenses.
- the main advantage of these thermoplastic materials is that they are lighter and less brittle than glass.
- these materials also have a major drawback, namely their low hardness compared to that of glass. As a result, these materials are more easily subject to scratching and alteration, even under normal use.
- compositions intended to form this type of coating Compositions based on thermally crosslinkable epoxyalkoxysilanes are described in US Pat. No. 4,211,823. These compositions make it possible to obtain hard polysiloxane coatings. A notable drawback of these compositions is the time required for crosslinking.
- patent application WO-A-02/00561 claims a method for manufacturing a coating obtained by crosslinking, cationically, of a epoxy monomer essentially based on glycidyl first by photopolymerization, then by thermal post-crosslinking in the presence of a thermal crosslinking catalyst.
- An American patent US-B-6,210,790 claims a colloidal silica modified by epoxy or propenyl ether groups and introduced into compositions crosslinkable by cationic route in hard coating.
- Colloidal silica is grafted with alkoxysilane in water.
- the composition comprises multifunctional monomers and in particular siloxane monomers with epoxy units and a cationic initiator of the onium salt type.
- a drawback of the technique described in this patent is on the one hand that it involves the prior functionalization of the colloidal silica with an alkoxysilane and on the other hand that it is necessary to remove the solvent for functionalization of the silica before crosslinking.
- Document FR-A-2 749 587 describes a composition crosslinkable by radiation with a hard coating having anti-fog properties.
- This composition comprises a colloidal silica, an olefin comprising at least two unsaturations and at least one divalent oxyalkylene radical, and a trialkoxysilane with an olefinic functional group.
- the main anti-fog coating obtained from the composition described in document FR-A-2,749,587 has the main drawback of being sensitive to inhibition by oxygen in the air.
- composition of the prior art is capable of providing a hard coating having jointly anti-fog and anti-fouling properties. Indeed, it turns out that the mechanisms of anti-fog and anti-fouling properties are generally incompatible.
- a first objective of the present invention is to provide a new cationically curable composition in a hard coating.
- a cationically crosslinkable composition with a hard coating comprising colloidal particles of non-functionalized silica, characterized in that it additionally comprises:
- At least one monomer, oligomer and / or crosslinkable and / or polymerizable silicone polymer comprising:
- - R ° identical or different when a> l, represents an alkyl, cycloalkyl, aryl, vinyl, hydrogen, alkoxy radical, preferably a lower C ⁇ -C 6 alkyl,
- Z 1 identical or different when the number of units of formula (I) is greater than 1, is an organic substituent comprising at least one reactive epoxy, and / or alkenylether and / or oxetane and / or dioxolane and / or carbonate function , and preferably Z 1 being an organic substituent comprising at least one reactive epoxy and / or dioxolane function,> and a total number of silicon atoms per molecule at least equal to 2, and
- hard coating is meant a coating whose pencil hardness is at least equal to H.
- this composition also comprises, as anti-fogging compound, at least one monomer, oligomer and / or crosslinkable and / or polymerizable silicone polymer comprising at least one unit of formula (II):
- - Z 2 identical or different when the number of units of formula (II) is greater than 1, is an organic substituent comprising at least one oxyalkyl or polyoxyalkyl function ((CH) m O) x or (CH 2 -CH (CH 3 ) -O) y or copolymers, said monomer, oligomer and / or polymer having a viscosity of less than 500 mPa-s "1 and preferably less than 300 mPa.s " 1 .
- An effective compound may be, for example, a mixture of a silicone-polyether block copolymer and of free polyether, sold under the reference Rhodorsil® oil 10646.
- An effective organic compound can also be a vinyl ether sold under the reference Rapicure® DPE2 (CAS N ° 765-12-8), DVE3 (CAS N ° 114188-95-3), or DPE3 (114266-85-2). It participates in effect in cationic polymerization and is integrated into the network making the treatment very effective.
- anti-fog compounds can be, for example, sodium sulfosuccinate. It may also be any surfactant comprising hydrophilic groups such as polyoxyethylene, polyoxypropylene, sulfate, sulfonate or carboxylate of alkali metals, polyols, amine salts, quaternary amines.
- composition according to the invention comprises, as anti-fouling compound, at least one monomer, oligomer and / or crosslinkable silicone polymer and / or polymerizable comprising at least one unit of formula (III):
- R ° represents an alkyl, cycloalkyl, aryl, vinyl, hydrogen, alkoxy radical, preferably a C 1 -C 6 lower alkyl,
- Y is a polymerizable group or a fluorine or hydrogen atom, a is between 1 and 7,
- perfluoropolyether compound has an average molecular weight between 500 and 20,000.
- - perfluorinated compounds containing an epoxy function or vinyl ether such as glycidyloctafluoropentylether the glycidyltetrafluoroethylether, glycidyl Tetrafluoropropylether, the glycidylhexa-decafluorononyl the glycidyldodecafluoroheptylether the heptadecafluorononyloxirane the heptafluorobutyloxirane the hexadecafluorononylether the hexadecafluoro8- (trifluoromethyl ) nonyloxirane, dodecafluoro ⁇ trifluoromethylheptyloxirane, octafluoropentanol, heptadecafluorononanol, heptadecafluoro- decanol ... - Asahi Glass products such as C 8 F
- the cationic initiator can be chosen from those whose cationic entity is selected from onium salts of formula (V):
- A represents an element from groups 15 to 17 such as for example: I, S, Se, P orN,
- R 1 represents a C 6 -C 20 carbocyclic or heterocyclic aryl radical, said heterocyclic radical possibly containing nitrogen or sulfur as heteroelements,
- R 2 represents RI or a linear or branched C1-C30 alkyl or alkenyl radical; said radicals RI and R2 being optionally substituted by a C1-C25 alkoxy, C1-C25 alkyl, nitro, chloro, bromo, cyano, carboxy, ester or mercapto group, • n is an integer ranging from 1 to v + 1 , v being the valence of the element A,
- the anionic entity of the initiator is a borate of formula (IN): [BX a R b ] " (NI)
- a phenyl radical substituted by at least one electron-withdrawing group such as for example OCF 3 , CF 3 , ⁇ O 2 , CN, and / or by at least 2 halogen atoms (especially fluorine), and this when the cationic entity is an onium of an element from groups 15 to 17,
- a phenyl radical substituted by at least one element or an electron-withdrawing group in particular a halogen atom (especially fluorine), CF 3 , OCF 3 , NO 2 , CN, and this when the cationic entity is an organometallic complex of a element from groups 4 to 10
- an aryl radical containing at least two aromatic rings such as for example biphenyl, naphthyl, optionally substituted by at least one element or an electron-withdrawing group, in particular a halogen atom, in particular fluorine, OCF3, CF3, NO2, CN, whatever the cationic entity.
- the initiator can advantageously be chosen from the group consisting of: [(C 8 H 17 ) -O- ⁇ -I- ⁇ )] + , [B (C 6 F 5 ) 4 ] -, [(CH 3 ) 2 -CH- ⁇ -I- ⁇ -CH3] + , [B (C 6 F 5 ) 4 ] - [(C ⁇ 2 H 25 - ⁇ -I- ⁇ ] + , [B (C 6 F 5 ) 4 ] - [(C 8 H 17 -O- ⁇ ) 2 I] + , [B (C 6 F 5 ) 4 ] -
- the initiator can also be a non-toxic onium salt whose cationic structure is of formula (Nile):
- R 1 represents the radical - ⁇ -R 2 , R 2 being a linear or branched alkyl radical comprising from 1 to 20 carbon atoms, preferably 1 to 15 carbon atoms.
- the anionic structure of the onium salt is chosen from the group comprising: Cl “ , B, BF 4 " , PF 6 ⁇ CF 3 SO 3 -, ⁇ (SO 2 CF 3 ) 2 -, C (SO 2 SF 3 ) 2 ' , B (C 6 F 5 ) -f, B (PhOCF 3 ) 4 “ , SbF ⁇ f and / or AsF 6 " .
- the following initiators have been found to be particularly interesting:
- Such initiators are described in document FR-A-2 762 001.
- the silicone oligomer is defined by the following formula (VIII)
- R ° represents an alkyl, cycloalkyl, aryl, vinyl, hydrogen, alkoxy radical, preferably a lower C ⁇ -C 6 alkyl,
- the silica used can be from different sources: precipitation silica, combustion silica, silica aerogels, silica sol and / or natural silica.
- the amorphous silica contained mainly or completely in the silicone phase comes from silica sol and more particularly from silica organosols; a general description of silica soils is given in document US 2,801,185 and "The colloid chemistry of silica and silicates" (Ralph K. Iler, Cornell University Press - 1955, see in particular pages 120-121).
- silica organosols examples include those from the companies Clariant, Fuso Chemicals, Nalco, Degussa-Huls and Dupont Chemicals.
- the silica particles have an average diameter of less than 1 ⁇ m, and more preferably between 50 and 500 nm.
- colloidal or combustion silica used to reinforce the coating is conveyed in an organic solvent and in particular an alcoholic solvent such as secondary or tertiary primary alcohols.
- alcoholic solvent such as secondary or tertiary primary alcohols.
- Isopropanol or diacetone alcohol are the solvents of choice.
- ketones tetrahydrofuran, hydrocarbon fractions or fluorinated solvents.
- the proportion of organic solvent in the composition according to the invention is at least equal to 10 parts by weight.
- Another subject of the invention relates to a process for producing a cationically crosslinkable composition as a hard coating as described above, which essentially comprises the step consisting in mixing particles of colloidal silica which is not functionalized with:
- At least one monomer, oligomer and / or crosslinkable and / or polymerizable silicone polymer comprising at least one unit of formula (I) and a total number of silicon atoms per molecule at least equal to 2,
- Another object of the invention relates to a process for producing a hard coating on a support based on at least one thermoplastic material, characterized in that it comprises the steps consisting in: a) mixing a non-functionalized colloidal silica with:
- At least one monomer, oligomer and / or crosslinkable and / or polymerizable silicone polymer comprising at least one unit of formula (I) and a total number of silicon atoms per molecule at least equal to 2,
- At least one monomer, oligomer and / or crosslinkable and / or polymerizable silicone polymer comprising at least one unit of formula (III) or a compound; b) applying the mixture obtained on the support based on at least one thermoplastic material, and c) curing the composition by crosslinking into a hard coating by thermal or actinic route.
- a volatile organic solvent which is evaporated before irradiation.
- the solvent is volatilized before irradiation but can also react with the base, in the case of alcohols which react with the oxirane functions during the process, in this case there is a reactive diluent.
- a last object of the invention relates to a hard coating obtained from the composition or by the process according to the invention.
- compositions of the examples are the following:
- Highlink OG (OG1-32 (ethylene glycol), OG8-32 (pentanediol), OG401-31 (ethylene glycol monopropyl ether), OG502-30 (isopropanol), OG502-31 (isopropanol), OG600-51 (butyl acetate)) marketed by Clariant®
- This solution is sold by the company EXXENE for anti-abrasion coatings. This solution is applied by soaking on a polycarbonate plate at 20 ° C and then dried at 25 ° C for 10 min followed by thermal crosslinking at 122 ° C for 35 min. The thickness of the film is two micrometers.
- Example 2 Preparation of a UN formulation according to the invention without anti-fog 10 g of siloxane resin having a monomer content (A) greater than 90% are loaded into a beaker, obtained by hydrosilylation of 4-vinylcyclohex-1-ene epoxide (NCMX), 1.25 g of photoinitiator system containing 20% of PI photoinitiator dissolved in isopropanol; 40g of highlink colloidal silica in solution in isopropanol at 30%. The system is stable for at least 6 months at room temperature away from light and heat. The solution is applied by soaking on a polycarbonate plate. Leave to drain for a minute.
- NCMX 4-vinylcyclohex-1-ene epoxide
- the system is crosslinked by passing over a UN bench at the speed of 5m / min equipped with two 160W / cm Hg lamps.
- the system is dry and very hard at the end of the bench.
- the thickness of the film is 3 micrometers.
- the pencil hardness is 3 hours immediate and greater than 4 hours after 24 hours. Annealing for 1 hour at 150 ° C or under an InfraRed ramp for a few minutes allows a hardness of 5 hours to be obtained.
- Example 3 Preparation of a UN formulation according to the invention with anti-fog
- siloxane resin having a monomer content (A) greater than 90% are charged into a beaker, 1.25 g of photoinitiator system containing 20% of photoinitiator PI dissolved in isopropanol; 40g of highlink colloidal silica in solution in isopropanol and 0.5 g of polyether silicone Rhodorsil oil 10646.
- the system is stable for at least 6 months at room temperature away from light and heat.
- the solution is applied by soaking on a polycarbonate plate.
- the system is crosslinked by passing over a UN bench at the speed of 5 m / min equipped with two lamps of 160 / cm Hg.
- the system is dry and very hard at the end of the bench.
- the film thickness is 3 micrometers
- the pencil hardness is 3 hours immediate and greater than 4 hours after 24 hours.
- Polycarbonate glass placed in the fridge at 5 ° C does not fog when it comes out of the fridge and placed in an atmosphere at 100% relative humidity and 25 ° C.
- siloxane resin having a monomer content (A) greater than 90% are charged into a beaker, 1.25 g of photoinitiator system containing 20% of photoinitiator PI dissolved in isopropanol; 38g of highlink colloidal silica in solution in isopropanol and 2 g of polyfluorosilane tridecafluoro-1,1,2,2 tetrahydrooctyl trimethoxysilane
- the system is stable for at least 6 months at room temperature away from light and heat.
- the solution is applied by soaking on a polycarbonate plate.
- the system is crosslinked by passing over a UN bench at the speed of 5m / min equipped with two 160W / cm Hg lamps. The system is dry and very hard at the end of the bench.
- the thickness of the film is 3 micrometers.
- the pencil hardness is 3 hours immediate and greater than 4 hours after 24 hours.
- thermal post-crosslinking is carried out for 1 hour at 100 ° C. to be sure of removing traces of unreacted alkoxy silyl.
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- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Health & Medical Sciences (AREA)
- Pathology (AREA)
- Immunology (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Analytical Chemistry (AREA)
- Paints Or Removers (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Silicon Polymers (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0215946A FR2848563B1 (fr) | 2002-12-16 | 2002-12-16 | Composition silicone pour revetement dur, a base de silice colloidale, durcissable par voie cationique, antibuee et/ou antisalissures |
FR0215946 | 2002-12-16 | ||
PCT/FR2003/003614 WO2004063300A1 (fr) | 2002-12-16 | 2003-12-08 | Composition silicone pour revetement dur, a base de silice colloidale, durcissable par voie cationique, antibuee et/ou antisalissures. |
Publications (1)
Publication Number | Publication Date |
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EP1572819A1 true EP1572819A1 (fr) | 2005-09-14 |
Family
ID=32338852
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP03815084A Withdrawn EP1572819A1 (fr) | 2002-12-16 | 2003-12-08 | Composition silicone pour revetement dur, a base de silice colloidale, durcissable par voie cationique, antibuee et/ou antisalissures. |
Country Status (7)
Country | Link |
---|---|
US (2) | US20060040113A1 (ja) |
EP (1) | EP1572819A1 (ja) |
JP (1) | JP4191141B2 (ja) |
CN (2) | CN101851467A (ja) |
AU (1) | AU2003296771A1 (ja) |
FR (1) | FR2848563B1 (ja) |
WO (1) | WO2004063300A1 (ja) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005089697A (ja) * | 2003-09-19 | 2005-04-07 | Toagosei Co Ltd | 活性エネルギー線硬化型組成物 |
JP2005150235A (ja) | 2003-11-12 | 2005-06-09 | Three M Innovative Properties Co | 半導体表面保護シート及び方法 |
US8163354B2 (en) * | 2006-05-29 | 2012-04-24 | Essilor International Compagnie Generale D'optique | Process for obtaining a hard coated article having anti-fouling properties |
US8105623B2 (en) * | 2006-06-30 | 2012-01-31 | Bausch & Lomb Incorporated | Fluorinated poly(ether)s end-capped with polymerizable cationic hydrophilic groups |
US20080014532A1 (en) * | 2006-07-14 | 2008-01-17 | 3M Innovative Properties Company | Laminate body, and method for manufacturing thin substrate using the laminate body |
US20080255318A1 (en) * | 2006-11-21 | 2008-10-16 | Momentive Performance Materials Inc. | Organosilicone compositions and methods for preparing them |
US20090017323A1 (en) * | 2007-07-13 | 2009-01-15 | 3M Innovative Properties Company | Layered body and method for manufacturing thin substrate using the layered body |
US20090017248A1 (en) * | 2007-07-13 | 2009-01-15 | 3M Innovative Properties Company | Layered body and method for manufacturing thin substrate using the layered body |
KR20090107882A (ko) * | 2008-04-10 | 2009-10-14 | 삼성전자주식회사 | 고정층을 포함하는 경사 조성 봉지 박막 및 그의 제조방법 |
JP2010062269A (ja) * | 2008-09-02 | 2010-03-18 | Three M Innovative Properties Co | ウェーハ積層体の製造方法、ウェーハ積層体製造装置、ウェーハ積層体、支持層剥離方法、及びウェーハの製造方法 |
US9011970B2 (en) * | 2010-07-30 | 2015-04-21 | Essilor International | Process for preparing articles having anti-fog layer by layer coating and coated articles having enhanced anti-fog and durability properties |
JP5737466B1 (ja) | 2013-08-02 | 2015-06-17 | ダイキン工業株式会社 | 重合性官能基及び架橋性官能基からなる群より選択される少なくとも1種の基を含有する含フッ素重合体を含む組成物及び塗装物品 |
KR101546729B1 (ko) * | 2013-12-11 | 2015-08-24 | 한국과학기술원 | 에폭시 실록산 수지 조성물을 이용한 하드코팅막 및 이의 제조 방법 |
KR102626778B1 (ko) * | 2019-01-11 | 2024-01-17 | 누리온 케미칼즈 인터내셔널 비.브이. | 방오성 코팅 |
KR102442232B1 (ko) | 2019-12-02 | 2022-09-13 | 다우 실리콘즈 코포레이션 | 이형 코팅 제조용 조성물 |
WO2021232218A1 (en) * | 2020-05-19 | 2021-11-25 | Carl Zeiss Vision International Gmbh | Spectacle lens with antifogging properties |
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US4486504A (en) * | 1982-03-19 | 1984-12-04 | General Electric Company | Solventless, ultraviolet radiation-curable silicone coating compositions |
FR2688790B1 (fr) * | 1992-03-23 | 1994-05-13 | Rhone Poulenc Chimie | Compositions a base de polyorganosiloxanes a groupements fonctionnels reticulables et leur utilisation pour la realisation de revetements anti-adhesifs. |
US5385955A (en) * | 1992-11-05 | 1995-01-31 | Essilor Of America, Inc. | Organosilane coating composition for ophthalmic lens |
US5393818A (en) * | 1993-04-06 | 1995-02-28 | Shell Oil Company | Solvent-free laminating adhesive composition from epoxidized block polymer |
JP3196621B2 (ja) * | 1995-04-20 | 2001-08-06 | 信越化学工業株式会社 | 水溶性表面処理剤 |
JP2001316626A (ja) * | 2000-05-02 | 2001-11-16 | Seikoh Chem Co Ltd | コーティング剤 |
US6514574B1 (en) * | 2000-06-29 | 2003-02-04 | Essilor International Compagnie Generale D'optique | Process for making an abrasion resistant coating onto an organic glass substrate |
US6558803B1 (en) * | 2000-07-03 | 2003-05-06 | Adhesives Research Inc. | Ambifunctional perfluorinated polyethers |
AU8114101A (en) * | 2000-08-07 | 2002-02-18 | 3M Innovative Properties Co | Information display protectors |
JP2002348534A (ja) * | 2001-05-25 | 2002-12-04 | Nippon Arc Co Ltd | ハードコート組成物およびハードコート製品 |
WO2002102907A1 (fr) * | 2001-06-13 | 2002-12-27 | Nippon Arc Co., Ltd. | Composition de revetement et article revetu de ladite composition |
US6593392B2 (en) * | 2001-06-22 | 2003-07-15 | Corning Incorporated | Curable halogenated compositions |
JP4149924B2 (ja) * | 2001-09-11 | 2008-09-17 | スリーエム イノベイティブ プロパティズ カンパニー | 耐汚染性ナノ複合材ハードコートおよびその製造方法 |
EP2257605A4 (en) * | 2008-03-11 | 2011-03-09 | 3M Innovative Properties Co | HART COATING COMPOSITION |
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2002
- 2002-12-16 FR FR0215946A patent/FR2848563B1/fr not_active Expired - Fee Related
-
2003
- 2003-12-08 JP JP2004566097A patent/JP4191141B2/ja not_active Expired - Fee Related
- 2003-12-08 CN CN201010196246A patent/CN101851467A/zh active Pending
- 2003-12-08 CN CNA2003801082992A patent/CN1735667A/zh active Pending
- 2003-12-08 AU AU2003296771A patent/AU2003296771A1/en not_active Abandoned
- 2003-12-08 EP EP03815084A patent/EP1572819A1/fr not_active Withdrawn
- 2003-12-08 WO PCT/FR2003/003614 patent/WO2004063300A1/fr active Application Filing
-
2005
- 2005-06-16 US US11/153,622 patent/US20060040113A1/en not_active Abandoned
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2007
- 2007-03-26 US US11/727,402 patent/US8328929B2/en not_active Expired - Fee Related
Non-Patent Citations (1)
Title |
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See references of WO2004063300A1 * |
Also Published As
Publication number | Publication date |
---|---|
JP2006511673A (ja) | 2006-04-06 |
FR2848563A1 (fr) | 2004-06-18 |
AU2003296771A1 (en) | 2004-08-10 |
JP4191141B2 (ja) | 2008-12-03 |
FR2848563B1 (fr) | 2006-07-28 |
US20080064832A1 (en) | 2008-03-13 |
CN101851467A (zh) | 2010-10-06 |
WO2004063300A1 (fr) | 2004-07-29 |
US8328929B2 (en) | 2012-12-11 |
CN1735667A (zh) | 2006-02-15 |
US20060040113A1 (en) | 2006-02-23 |
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