WO2011080472A2 - Article d'optique comportant un revetement antibuee temporaire ayant une durabilite amelioree - Google Patents
Article d'optique comportant un revetement antibuee temporaire ayant une durabilite amelioree Download PDFInfo
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- WO2011080472A2 WO2011080472A2 PCT/FR2010/052895 FR2010052895W WO2011080472A2 WO 2011080472 A2 WO2011080472 A2 WO 2011080472A2 FR 2010052895 W FR2010052895 W FR 2010052895W WO 2011080472 A2 WO2011080472 A2 WO 2011080472A2
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Classifications
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- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C7/00—Optical parts
- G02C7/02—Lenses; Lens systems ; Methods of designing lenses
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- 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
- C03C17/30—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material with silicon-containing compounds
-
- 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
-
- 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
- G02B1/11—Anti-reflection 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
- G02B1/11—Anti-reflection coatings
- G02B1/111—Anti-reflection coatings using layers comprising organic materials
-
- 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
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B27/00—Optical systems or apparatus not provided for by any of the groups G02B1/00 - G02B26/00, G02B30/00
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- 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
- C03C2217/00—Coatings on glass
- C03C2217/70—Properties of coatings
- C03C2217/75—Hydrophilic and oleophilic coatings
-
- 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
- C03C2218/00—Methods for coating glass
- C03C2218/30—Aspects of methods for coating glass not covered above
- C03C2218/31—Pre-treatment
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- 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
- Y10T428/249921—Web or sheet containing structurally defined element or component
- Y10T428/249953—Composite having voids in a component [e.g., porous, cellular, etc.]
Definitions
- the present invention relates to a coated optical article having on its surface silanol groups, generally an antireflection coating, the surface of which has been modified to allow effective and durable application of a temporary anti-fog solution, and that a method of manufacturing such an optical article.
- hydrophilic coatings having a low static contact angle with water, preferably less than 50 °, better less than 25 °.
- These permanent anti-fog coatings act as sponges to the mist and allow the water droplets to adhere to the surface of the substrate forming a very thin film giving a feeling of transparency.
- These coatings generally consist of very hydrophilic species such as sulfonates or polyurethanes.
- EP 1324078 discloses a lens coated with an anti-abrasion coating and a multilayer antireflection coating comprising an alternation of high and low refractive index layers whose outer layer is a low refractive index layer (1, 42-148) 5-100 nm thick forming an anti-fog coating consisting of a hybrid layer having a static contact angle with water of less than 10 °, obtained by vacuum deposition simultaneously of an organic compound and silica or silica and alumina, that is to say by co-evaporation of these various constituents.
- the anti-fog coating preferably contains from 0.02 to 70% by weight of organic compound relative to the total weight of the coating, and typically from 6 to 15% by weight, according to the examples.
- the organic compound has a hydrophilic group and a reactive group, for example a trialkoxysilyl group having 3 to 15 carbon atoms, and preferably has a molecular weight of 150 to 1500 g / mol.
- Some preferred compounds have a polyether backbone, especially polyoxyethylene, and a reactive group at each end of the molecule.
- the preferred compounds are polyethylene glycol glycidyl ether, polyethylene glycol monoacrylate and N- (3-trimethoxysilylpropyl) gluconamide.
- the anti-fog coating is therefore a layer of silica (or silica and alumina) incorporating a hydrophilic organic compound. Its anti-fog character however evolves over time, and a deterioration of the anti-fogging properties is gradually observed. When they become too weak, they can be restored by a "wash" treatment of the anti-fog film, in particular a plasma treatment.
- US Pat. Nos. 6,251, 523 and US 6,379,776 disclose an anti-fog and anti-reflective glass for automobiles or lenses, comprising a glass substrate having a silica-based antireflection coating of 10-250 nm in thickness having a surface roughness Ra of 1 order of 5-10 nm, itself coated with a permanent anti-fog coating 8 nm thick obtained by liquid or vapor deposition of the compound CH 3 0- (CH 2 CH 2 0) 6-9 - (CH 2 ) 3 Si (OCH 3 ) 3 or a hydrolyzate of this compound.
- the anti-fog coating has a static contact angle with the water of 3 °.
- Another solution for combining antireflection and anti-fogging properties is to use a porous thin layer of low refractive index, consisting in part of surfactants, which allow the layer to acquire anti-fogging properties.
- This layer is generally deposited on a hydrophilic surface.
- US Pat. No. 5,997,621 describes a porous antireflection and anti-fog coating based on metal oxides (silica beads) and anionic surfactants that are moderately soluble in water, generally having an ionic hydrophilic head of carboxylic acid, sulfonate, phosphate and a fluorinated chain.
- the surfactants are preferably capable of covalently bonding to the metal oxides.
- WO 97/43668 discloses an analogous construction.
- EP 0871046 discloses an anti-fog and antireflection system comprising a porous inorganic oxide-based layer deposited on a water-absorbing layer a few microns thick, obtained by polycondensation of an inorganic alkoxide hydrolyzate in the presence of a compound of polyacrylic acid.
- the porous layer which acts as an antireflection, allows access of water to the absorbent layer.
- Anti-fogging properties can also be obtained by applying temporary commercial solutions, available in the form of spray or wipes, on spectacle lenses having as an outer layer an anti-fouling coating (hydrophobic and oleophobic), often considered essential when the ophthalmic lens has an anti-reflective coating. They make it possible to obtain the anti-fogging property over a short period of time. The ease of cleaning provided by the antifouling coating is retained, but after some wiping, the anti-fogging property is largely degraded. Indeed, the temporary solutions contain materials of hydrophilic nature having weak interactions with the hydrophobic surface of the antifouling coating, so that after some wiping, these hydrophilic materials are removed.
- a more interesting solution is to obtain an anti-fog coating by applying a temporary hydrophilic solution to the surface of a precursor coating of an anti-fog coating, which is an alternative to permanent anti-fogging coatings.
- EP 1275624 discloses a lens coated with a hard inorganic hydrophilic layer based on metal oxides and silicon oxide. Its hydrophilic nature and the presence of nanoscale concave portions on its surface allow to impregnate a surfactant and retain it adsorbed for a long time, which maintains an anti-fogging effect for several days. However, an anti-fogging effect also occurs in the absence of surfactant.
- JP 2004-317539 and JP 2005-281 143 disclose a lens coated with a multilayer antireflective coating and / or an abrasion-resistant coating and an anti-fog coating precursor coating having a static contact angle with the coating. water from 50 ° to 90 °.
- the anti-fog coating itself which is a temporary coating, is obtained after application to the surface of the precursor coating of a surfactant.
- the precursor coating of the anti-fog coating is obtained from a composition comprising an organic compound comprising a hydrophilic group of polyoxyethylene nature, a reactive group capable of reacting with the outer layer of the antireflection coating, in particular a layer of silica, such as the groups alkoxysilane Si (OR) n , silanol SiOH or isocyanate, and optionally a fluorinated hydrophobic group, and the composition is chosen so that the static contact angle with water of the precursor coating of the anti-fog coating varies from 50 ° to 90 °.
- the organic compounds used in the precursor of the anti-fog coating preferably have a molar mass of 700-5000 or 430-3700 g / mol.
- Examples of such compounds include the compounds CH 3 0 (CH 2 CH 2 0) 22 CONH (CH 2 ) 3 Si (OCH 3 ) 3 or C 8 F 17 0 (CH 2 CH 2 0) 2 CONH ( CH 2 ) 3 Si (OCH 3 ) 3.
- the precursor coating is described as having 0.5 to 20 nm thickness. The relatively high contact angle of the precursor coating is sought because it allows, according to these applications, to easily remove dirt from the drying of water drops.
- Anti-fog coatings also having good mechanical properties, (abrasion and scratch resistance) are sought.
- the objective of the present invention is the preparation of such temporary anti-fogging coatings, which substantially improve the durability of the anti-fogging property, while retaining good mechanical properties.
- Another object of the invention is to obtain an immediately operational anti-fog coating, that is to say a coating which, when a transparent glass substrate coated with this coating is placed under conditions generating fogging on said coating of said substrate not equipped, allows to reach immediately (i.e. in less than 1 second) visual acuity> 6/10 th, and preferably 10/1 o Similarly, without fogging to an observer observing through the glass coated with a Snellen visual acuity scale E (SCALE ARMAIGNAC (Tridents) (Snellen's E) READING AT 5M, ref T6 available from FAX INTERNATIONAL) located 5 meters away.
- SCALE ARMAIGNAC Tridents
- Another object of the invention is to obtain an optical article having both anti-fog and antireflection properties.
- the present invention relates to an optical article, preferably a spectacle lens, comprising a substrate coated with a coating having on its surface silanol groups and, in direct contact with this coating, a precursor coating of a coating anti-fog, characterized in that the precursor coating of the anti-fog coating:
- - has a thickness less than or equal to 5 nm
- - has a static contact angle with water greater than 10 ° and less than 50 °.
- the invention also relates to an optical article, preferably a spectacle lens, as above, the precursor coating of the anti-fog coating is further coated with a film of a liquid solution containing at least one surfactant.
- this optical article is coated with a temporary anti-fog coating according to the invention.
- FIG. 1 shows the evolution, as a function of time, of the anti-fogging properties of optical articles according to the invention and comparatives initially exposed to steam. hot.
- a coating which is "on” a substrate / coating or which has been “deposited” on a substrate / coating is defined as a coating which (i) is positioned above the substrate / coating, (ii) not necessarily in contact with the substrate / coating, i.e. one or more intermediate coatings may be provided between the substrate / coating and the coating in question (however, it is preferably in contact with said substrate / coating), and (iii) does not necessarily cover the substrate / coating completely.
- anti-fog coating in the present application a coating which, when a transparent glass substrate coated with this coating is placed under conditions generating fogging on said substrate not equipped with said coating, allows immediate visual acuity> 6/10 th for an observer looking through a coated glass eye chart located 5 meters away.
- anti-fog coatings may either not fog up at their surface (no visual distortion in the ideal case, or visual distortion but visual acuity> 6 / 10th under the measurement conditions given below).
- a non-fog resistant coating does not allow visual acuity> 6 / 10th as long as it is exposed to fogging conditions and generally exhibits condensation under the measurement conditions indicated above.
- anti-fogging glass in the present application a glass equipped with an “anti-fog coating” as defined above.
- the precursor of the anti-fog coating according to the invention which is a hydrophilic coating, is not considered to be an anti-fog coating within the meaning of the invention, even if it exhibits certain anti-fogging properties, which can be noted, for example by means of a breath test described in the experimental part. Indeed, this precursor anti-fog coating does not allow a visual acuity> 6 / 10th under the measurement conditions indicated above, as shown in Figure 1, which will be discussed later.
- temporary anti-fog coating an anti-fog coating obtained after the application of a liquid solution containing at least one surfactant to the surface of a precursor coating of said anti-fog coating.
- the durability of a temporary anti-fog coating is generally limited by wiping its surface, the surfactant molecules not being permanently attached to the surface of the coating but simply adsorbed more or less sustainably.
- the optical article prepared according to the invention comprises a substrate, preferably transparent, having main front and rear faces, at least one of said main faces comprising a coating comprising on its surface silanol groups, preferably both main faces.
- rear face (generally concave) of the substrate is meant the face which, when using the article, is closest to the eye of the wearer.
- front face (generally convex) of the substrate means the face which, when using the article, is furthest from the eye of the wearer.
- the article according to the invention may be an optical article of any kind likely to be confronted with a fogging, such as a screen, a glazing for the automotive industry or the building, or a mirror, it is preferably an optical lens, better an ophthalmic lens, for spectacles, or an optical or ophthalmic lens blank.
- the coating comprising on its surface silanol groups of the invention may be formed on at least one of the main faces of a bare substrate, that is to say uncoated, or on at least one of the faces of a substrate already coated with one or more functional coatings.
- the substrate of the optical article according to the invention may be an inorganic or organic glass, for example an organic glass of thermoplastic or thermosetting plastic material.
- Particularly preferred classes of substrates are poly (thiourethanes), polyepisulfides and resins resulting from the polymerization or (co) polymerization of alkylene glycol bisalkylcarbonates. They are sold, for example, under the CR-39 ® trade name by PPG Industries (ORMA ® Essilor lenses).
- the main surface of the substrate is coated with one or more functional coatings prior to the deposition of the coating having on its surface silanol groups.
- These functional coatings conventionally used in optics may be, without limitation, a layer of shockproof primer, an anti-abrasion and / or anti-scratch coating, a polarized coating, a photochromic coating or a colored coating, in particular a layer of shockproof primer coated with an anti-abrasion and / or anti-scratch layer.
- the coating comprising on its surface silanol groups is preferably deposited on an abrasion-resistant and / or anti-scratch coating.
- the anti-abrasion and / or anti-scratch coating may be any layer conventionally used as an anti-abrasion and / or anti-scratch coating in the field of ophthalmic lenses.
- the abrasion-resistant and / or scratch-resistant coatings are preferably hard coatings based on poly (meth) acrylates or silanes, generally comprising one or more mineral fillers intended to increase the hardness and / or the refractive index of the product. coating once cured.
- (meth) acrylate is meant an acrylate or a methacrylate.
- the hard anti-abrasion and / or anti-scratch coatings are preferably prepared from compositions comprising at least one alkoxysilane and / or a hydrolyzate thereof, obtained for example by hydrolysis with a hydrochloric acid solution, and optionally condensation and / or curing catalysts and / or surfactants.
- the thickness of the anti-abrasion and / or anti-scratch coating generally varies from 2 to 10 ⁇ , preferably from 3 to 5 ⁇ .
- This coating may be any layer of shockproof primer conventionally used for articles made of transparent polymeric material, such as ophthalmic lenses.
- compositions based on thermoplastic polyurethanes such as those described in patents JP 63-141001 and JP 63-87223, poly (meth) acrylic primer compositions, such as those described in US Pat. US Pat. No. 5,015,523, compositions based on thermosetting polyurethanes, such as those described in patent EP 0404111 and compositions based on poly (meth) acrylic latex or polyurethane type latex, such as those described in US Pat. US 5,316,791 and EP 0680492.
- Preferred primer compositions are polyurethane-based compositions and latex-based compositions, particularly polyurethane and poly (meth) acrylic latices, and mixtures thereof.
- the primer layers generally have thicknesses, after hardening, of 0.2 to 2.5 ⁇ , preferably 0.5 to 1.5 ⁇ .
- coating comprising on its surface silanol groups is meant a coating which naturally has on its surface silanol groups, or a coating whose silanol groups have been created after it has been subjected to surface activation treatment.
- This coating is therefore a coating based on siloxanes or silica, for example, without limitation, a silica layer, a sol-gel coating, based in particular on organosilanes such as alkoxysilanes, or a coating based on colloids of silica.
- an anti-abrasion and / or anti-scratch coating may be in particular an anti-abrasion and / or anti-scratch coating, or, in the preferred embodiment, a monolayer antireflection coating or a multilayer antireflection coating whose outer layer has on its surface silanol groups.
- outer layer of a coating is meant the layer furthest from the substrate.
- the surface activation treatment creating silanol groups or at least increasing their proportion to the surface of a coating is generally conducted under vacuum. It can be a bombardment with energy and / or reactive species, for example an ion beam ("Ion Pre-Cleaning" or "IPC") or an electron beam, a discharge treatment corona, by effluvage, a UV treatment, or vacuum plasma treatment, usually an oxygen or argon plasma. It can also be an acidic or basic surface treatment and / or solvent (water, hydrogen peroxide or organic solvent). Many of these treatments can be combined.
- energetic species and / or reactive is meant in particular ionic species having an energy ranging from 1 to 300 eV, preferably from 1 to 150 eV, better from 10 to 150 eV, and more preferably from 40 to 150 eV.
- the energetic species can be chemical species such as ions, radicals, or species such as photons or electrons.
- the activating treatment may also be an acidic, basic chemical surface treatment, preferably carried out by a liquid route, or a treatment by means of a solvent or mixture of solvents.
- the coating having on its surface silanol groups is preferably a low silica refractive index layer (comprising silica), ideally consisting of a silica (SiO 2 ) layer, generally obtained by vapor deposition.
- a low silica refractive index layer comprising silica
- SiO 2 silica
- Said SiO 2 -based layer may comprise, in addition to silica, one or more other materials conventionally used for the manufacture of thin layers, for example one or more materials chosen from the dielectric materials described below in the present description.
- This SiO 2 based layer is preferably free of Al 2 O 3 .
- the inventors have found that it is not essential to carry out a surface treatment when the layer is a silica-based layer, in particular when it is obtained by evaporation.
- the coating comprising on its surface silanol groups preferably comprises at least 70% by weight of SiO 2 , better still at least 80% by weight and better still at least 90% by weight of SiO 2 . As has been said, in an optimal embodiment, it comprises 100% by weight of silica.
- the coating comprising on its surface silanol groups may also be a sol-gel coating based on silanes such as alkoxysilanes, for example tetraethoxysilane or organosilanes such as ⁇ -glycidoxypropyltrimethoxysilane.
- silanes such as alkoxysilanes, for example tetraethoxysilane or organosilanes such as ⁇ -glycidoxypropyltrimethoxysilane.
- Such a coating is obtained by liquid deposition, using a liquid composition containing a hydrolyzate of silanes and optionally colloidal materials of high (> 1.55, preferably> 1, 60, better> to 1.70) or of low ( ⁇ 1, 55) refractive index.
- Such a coating whose layers comprise an organic / inorganic hybrid matrix based on silanes in which are dispersed colloidal materials for adjusting the refractive index of each layer are described for example in the patent FR 2858420
- the coating comprising on its surface silanol groups is a silica-based layer deposited on an anti-abrasion coating, preferably deposited directly on this anti-abrasion coating.
- Said silica-based layer (comprising silica) is preferably a silica layer, generally obtained by vapor deposition. It preferably has a thickness less than or equal to 500 nm, better ranging from 5 to 20 nm, and even better from 10 to 20 nm thick.
- the deposition of said silica-based layer is carried out by regulating the pressure, by adding gas to the deposition chamber, the gas being in non-ionic form, preferably by addition of oxygen, at a pressure typically ranging from of 5.10 "to 5.10 4 5 mbar.
- the optical article according to the invention comprises an antireflection coating.
- an antireflection coating When such a coating is present, it generally constitutes the coating comprising on its surface silanol groups within the meaning of the invention.
- This antireflection coating may be any antireflection coating conventionally used in the field of optics, in particular ophthalmic optics, provided that it has on its surface silanol groups.
- An antireflective coating is defined as a coating deposited on the surface of an optical article that enhances the anti-reflective properties of the final optical article. It reduces the reflection of light at the article-air interface over a relatively large portion of the visible spectrum.
- antireflection coatings conventionally comprise a monolayer or multilayer stack of dielectric materials. They are preferably multilayer coatings, including high refractive index layers (H1) and low refractive index layers (B1).
- a layer of the antireflection coating is said layer of high refractive index when its refractive index is greater than 1, 55, preferably greater than or equal to 1, 6, better still greater than or equal to 1, 8 and even more. better than or equal to 2.0.
- a layer of an antireflection coating is called a low refractive index layer when its refractive index is less than or equal to 1.55, preferably less than or equal to 1.50, better still less than or equal to 1.45.
- the refractive indexes referred to herein are expressed at 25 ° C for a wavelength of 550 nm.
- the H1 layers are conventional high refractive index layers well known in the art. They generally comprise one or more mineral oxides such as, without limitation, zirconia (ZrO 2 ), titanium oxide (TiO 2 ), tantalum pentoxide (Ta 2 O 5 ), neodymium oxide (Nd 2 0 5 ), praseodymium oxide (Pr 2 O 3 ), praseodymium titanate (PrTiO 3 ), La 3 O 3 , Dy 2 O 5 , Nb 2 O 5 , Y 2 0 3 .
- ZrO 2 zirconia
- TiO 2 titanium oxide
- Ta 2 O 5 tantalum pentoxide
- Nd 2 0 5 neodymium oxide
- Pr 2 O 3 praseodymium oxide
- PrTiO 3 praseodymium titanate
- Bl layers are also well known and may include, without limitation, SiO 2 , MgF 2 , ZrF 4 , alumina (Al 2 O 3 ), AlF 3 , chiolite (Na 3 Al 3 F 14 ), cryolite (Na 3 [AlF 6 ]), and mixtures thereof, preferably SiO 2 or SiO 2 doped with alumina. It is also possible to use SiOF layers (Si0 2 doped with fluorine).
- a layer B1 comprising a mixture of Si0 2 and Al 2 O 3
- it preferably comprises from 1 to 10%, better still from 1 to 8% and even more preferably from 1 to 5% by weight of Al 2 0 3 relative to the total mass of Si0 2 + Al 2 0 3 in this layer.
- the layers H1 have a physical thickness varying from 10 to 120 nm
- the layers B1 have a physical thickness varying from 10 to 100 nm.
- the total thickness of the antireflection coating is less than 1 micrometer, better still less than or equal to 800 nm and better still less than or equal to 500 nm.
- the total thickness of the antireflection coating is generally greater than 100 nm, preferably greater than 150 nm.
- the antireflection coating comprises at least two layers of low refractive index (B1) and at least two layers of high refractive index (H1).
- the total number of layers of the antireflection coating is less than or equal to 8, better still less than or equal to 6.
- the layers H1 and B1 are alternated in the antireflection coating, although they may be alternated according to one embodiment of the invention. Two or more layers H1 may be deposited one on top of the other, just as two or more layers B1 (or more) can be deposited one on top of the other.
- the different layers of the antireflection coating are preferably deposited by vapor deposition, under vacuum, according to one of the following techniques: i) by evaporation, possibly assisted by ion beam; ii) ion beam sputtering; iii) sputtering; iv) plasma enhanced chemical vapor deposition.
- i) by evaporation, possibly assisted by ion beam ii) ion beam sputtering; iii) sputtering; iv) plasma enhanced chemical vapor deposition.
- the coating comprising on its surface silanol groups is an antireflection coating
- the light reflection factor of an article coated with such an antireflection coating is less than 2.5% per side, better than 2 % per side and even better less than 1% per face of the article.
- the article comprises a substrate whose two main surfaces are coated with an antireflection coating according to the invention and has a total value of R v (cumulative reflection due to the two faces) of less than 1, 5%.
- R v total value of R v (cumulative reflection due to the two faces) of less than 1, 5%.
- the "light reflection factor” is as defined in ISO 13666: 1998, and measured in accordance with ISO 8980-4, that is, it is the weighted average of the spectral reflection over the entire visible spectrum between 380 and 780 nm.
- the surface of this coating Before formation of the precursor of the anti-fog coating on the coating comprising on its surface silanol groups, for example an antireflection coating, it is usual to subject the surface of this coating to a physical or chemical activation treatment intended to increase the adhesion of the precursor of the anti-fog coating.
- a physical or chemical activation treatment intended to increase the adhesion of the precursor of the anti-fog coating.
- the coating having on its surface silanol groups is directly in contact with the precursor coating of an anti-fog coating, which will now be described.
- precursor of an anti-fog coating is meant in the present application a coating which, if it is applied to its surface a liquid solution containing a surfactant so as to form a film, constitutes an anti-fog coating in the sense of the invention.
- the assembly consisting of the precursor coating and the surfactant-based solution film constitutes the anti-fog coating itself.
- the precursor coating of the anti-fog coating is a coating having a thickness of less than or equal to 5 nm, preferably 4 nm or less, more preferably 3 nm or less, and still more preferably 2 nm or less, having a static contact angle with the water greater than 10 ° and less than 50 °, which is obtained by permanent grafting of at least one organosilane compound having a polyoxyalkylene group and at least one silicon atom carrying at least one hydrolyzable group.
- the coating is deposited by application of a composition comprising a hydrolyzate of the organosilane compound having a polyoxyalkylene group and at least one silicon atom carrying at least one hydrolyzable group.
- organosilane compounds It is recommended to avoid condensation of hydrolysed organosilane compounds so that they can retain a maximum of free silanol functions to react in order to facilitate the grafting of these compounds on the surface of the optical article and to limit the formation of siloxane prepolymers before grafting. This explains why the thickness of organosilane compound deposited is also low.
- composition rather quickly after hydrolysis, typically less than 2 hours, preferably less than 1 hour, better less than 30 minutes after hydrolysis (by adding an acidic aqueous solution, typically HCI).
- the composition is applied less than 10 minutes, more preferably less than 5 minutes and preferably less than 1 minute after hydrolysis.
- the organosilane compound used is capable, thanks to its silicon-containing reactive group, of establishing a covalent bond with the silanol groups present on the surface of the coating on which it is deposited.
- the organosilane compound of the invention comprises a polyoxyalkylene chain functionalized at one end or at both ends, preferably at a single end, with a group comprising at least one silicon atom bearing at least one hydrolysable group.
- This organosilane compound preferably comprises a silicon atom bearing at least two hydrolyzable groups, preferably three hydrolyzable groups. Of preferably, it does not include a urethane group. It is preferentially a compound of formula:
- the groups Y identical or different, are monovalent organic groups bonded to silicon by a carbon atom
- the X groups which are identical or different, are hydrolyzable groups
- R 1 is a group comprising a polyoxyalkylene function
- m is a integer equal to 0, 1 or 2.
- m 0.
- the groups X are preferably chosen from alkoxy groups -OR 3 , in particular C 1 -C 4 alkoxy, acyloxy -O-C (O) R 4, where R 4 is an alkyl radical, preferably C 1 -C 6 , preferably methyl or ethyl, halogens such as Cl, Br and I or trimethylsiloxy (CH 3 ) 3 SiO-, and combinations of these groups.
- R 4 is an alkyl radical, preferably C 1 -C 6 , preferably methyl or ethyl, halogens such as Cl, Br and I or trimethylsiloxy (CH 3 ) 3 SiO-, and combinations of these groups.
- the groups X are alkoxy groups, and in particular methoxy or ethoxy, and better ethoxy.
- the Y group is present when m is not zero, is preferably a hydrocarbon group, saturated or unsaturated, preferably C 1 -C 1 0 and better -C 4, for example an alkyl group such as methyl or ethyl , a vinyl group, an aryl group, for example phenyl, optionally substituted, in particular with one or more alkyl groups in dC 4 .
- Y represents the methyl group.
- the compound of formula I comprises a trialkoxysilyl group such as a triethoxysilyl or trimethoxysilyl group.
- the polyoxyalkylene group of the organosilane compound (R 1 group) preferably comprises less than 80 carbon atoms, preferably less than 60 carbon atoms, and more preferably less than 50 carbon atoms.
- the group R 1 preferably satisfies these same conditions.
- the group R 1 generally has the formula -LR 2 , where L is a divalent group bonded to the silicon atom of the compounds of formula I or II by a carbon atom, and R 2 is a group comprising a polyoxyalkylene group bonded to L group via an oxygen atom, this oxygen atom being included in the group R 2 .
- Non-limiting examples of L groups are optionally substituted linear or branched alkylene groups, cycloalkylene, arylene, carbonyl, amido, where combinations of these groups such as cycloalkylene alkyl, biscycloalkylene, biscycloalkylenealkylene, arylenealkylene, bisphenylene, bisphenylenealkylene, amido alkylene, an example of which is the group CONH (CH 2 ) 3 , or the groups -OCH 2 CH (OH) CH 2 - and -NHC (O) -.
- preferred L groups are alkylene groups, preferably linear, preferably having 10 carbon atoms or less, more preferably 5 or less carbon atoms, for example ethylene and propylene.
- Preferred R 2 groups include a polyoxyethylene - (CH 2 CH 2 0) n -, polyoxypropylene group, or combinations thereof.
- Preferred organosilanes of formula I are compounds of the following formula II:
- R ' is a hydrogen atom, an acyl group or a linear or branched alkyl group, optionally substituted with one or more functional groups, and which may also comprise one or more double bonds
- R is a linear or branched alkylene group , preferably linear, for example an ethylene or propylene group
- X, Y and m are as defined above
- n' is an integer ranging from 1 to 10, preferably 1 to 5
- n is an integer ranging from 2 to 50, preferably from 5 to 30, more preferably from 5 to 15, m 'is 0 or 1, preferably 0, m "is 0 or 1, preferably 0.
- the groups L 'and L " when present, may be chosen from the divalent groups L previously described and preferably represent the group -OCH 2 CH (OH) CH 2 - or the group -NHC (O) -.
- the groups -OCH 2 CH (OH) CH 2 - or -NHC (O) - are connected to the adjacent groups (CH 2 ) n '(in the case of a group L') and R '(in the case of a group L ") via their oxygen atom (for the group -OCH 2 CH (OH) CH 2 -) or via their nitrogen atom (for the group - NHC (O) -).
- m 0 and the hydrolyzable groups X denote methoxy or ethoxy groups. It is preferably 3.
- R ' may also denote an aliphatic or aromatic acyl group, in particular the acetyl group.
- R ' may denote a trialkoxysilylalkylene or trihalosilylalkylene group such as the - (CH 2 ) n "Si (R 5 ) 3 group where R 5 is a hydrolysable group such as the groups X defined above and n" is an integer such that the group n 'defined previously.
- R ' is the group - (CH 2 ) 3 Si (OC 2 H 5 ) 3 .
- the organosilane compound comprises two silicon atoms carrying at least one hydrolyzable group.
- n is 3, or ranges from 6 to 9, from 9 to 12, from 21 to 24, or from 25 to 30, preferably from 6 to 9.
- the organosilane compound of the invention does not have a fluorine atom.
- the mass content of fluorine in the precursor coating of the anti-fog coating is less than 5%, preferably less than 1% by weight and better still 0%.
- the molar mass of the organosilane compound according to the invention ranges from 400 to 4000 g / mol, preferably from 400 to 1500 g / mol, better still from 400 to 1200 g / mol, and still more preferably from 400 to 1000 g / mol. mol.
- the precursor of the anti-fog coating comprises more than 80% by weight of organosilane compound according to the invention, relative to the total mass of the precursor of the anti-fog coating, preferably more than 90%, better more than 95% and ideally more than 98%.
- the anti-fogging coating precursor consists of a layer of said organosilane compound.
- the anti-fogging coating precursor of the invention contains less than 5% by weight of metal oxide or metalloid (for example silica or alumina) with respect to the total weight of the coating, better not including not.
- metal oxide or metalloid for example silica or alumina
- the organosilane compound used for the formation of the anti-fog coating is deposited under vacuum, preferably none metal oxide is co-evaporated with it, according to the technique of co-evaporation of at least one organic compound and at least one inorganic compound described in EP 1324078.
- the precursor coating of the anti-fog coating does not contain a crosslinking agent, which means that it is preferably not formed from a composition containing a crosslinking agent, for example tetraethoxysilane.
- the anti-fogging precursor of the invention has a static contact angle with water strictly greater than 10 ° and strictly less than 50 °, preferably less than or equal to 45 °, better ⁇ 40 °, even better ⁇ 30 ° and ideally ⁇ 25 °.
- This contact angle is preferably from 15 ° to 40 °, more preferably from 20 ° to 30 °.
- the deposition of the organosilane compound on the surface of the coating comprising silanol groups can be carried out according to usual techniques, preferably by deposition in the gas phase or in the liquid phase, ideally in the gas phase, by evaporation under vacuum.
- the grafting When the grafting is carried out in the gaseous phase, for example by evaporation under vacuum, it may be followed, if necessary, by a step of removing the excess of the deposited organosilane compound so as to retain only the organosilane compound actually grafted with the surface of the coating having silanol groups. The ungrafted molecules are thus removed.
- Such an elimination step must be carried out in particular when the thickness of the initially deposited anti-fogging coating precursor is greater than 5 nm.
- This step of removing the excess organosilane compound is however in some cases non-existent, insofar as it is possible to deposit the organosilane compound so as to form a grafted layer, that is to say when it is ensure that the deposited thickness does not exceed a few nanometers. Adjusting the deposition parameters to achieve such thicknesses is within the reach of those skilled in the art.
- the precursor coating of the anti-fog coating by depositing an excess of organosilane compound on the surface of the silanol-containing coating and removing the excess of this deposited but ungrafted compound.
- the inventors have found that when directly forming a grafted organosilane compound layer having a thickness less than or equal to 5 nm, which does not require removal of an excess of organosilane compound, it is possible in certain cases to obtain an anti-fog coating precursor coating whose surface does not have sufficient affinity for a liquid solution containing at least one surfactant, which would lead to a coating which does not possess the desired anti-fogging properties.
- the actual physical thickness of the layer of organosilane compound deposited in excess is preferably less than or equal to 20 nm.
- the removal of the excess organosilane compound deposited can be carried out by rinsing (liquid route) using, for example, a solution of soapy water and / or wiping (dry).
- the removal step comprises rinsing followed by wiping.
- the rinsing is carried out by cleaning the article with soapy water (containing a surfactant) by means of a sponge. Then rinse with deionized water, and optionally, the lens is then wiped for typically less than 20 seconds, preferably 5 to 20 seconds, using a fabric CEMOI TM or Selvith TM impregnated alcohol, typically isopropyl alcohol. Then rinse again with deionized water and wipe with a cloth. All of these steps can be done manually or be partially or fully automated.
- the step of removing excess organosilane compound results in a layer of organosilane compound having a thickness of 5 nm or less.
- the organosilane compound deposited on the surface of the optical article thus forms a monomolecular or quasi-monomolecular layer.
- the organosilane compound may be previously dissolved in a solvent before being evaporated to better control the rate of evaporation and deposition.
- the thickness of the film can be controlled in this way by this dissolution and by adjusting the amount of solution to be evaporated.
- the grafting is carried out by a liquid route, for example by dipping or centrifugation, it is generally not necessary to carry out a step of removing the excess of deposited organosilane compound.
- the precursor coating of the anti-fog coating according to the invention has a low roughness.
- the roughness Ra is less than 2 nm, typically of the order of 1 nm.
- Ra (nm) is the value of the average roughness of the measured surface:
- a temporary anti-fog coating according to the invention is obtained by depositing a film of a liquid solution containing at least one surfactant on the surface of the precursor coating of the anti-fog coating.
- This solution provides the lenses with temporary protection against fogging by creating a uniform layer on their surface that helps disperse the water droplets on the glass surface so that they do not form visible fogging.
- the application of the surfactant solution can be carried out by any known technique, in particular by dipping or centrifugation.
- the surfactant solution is preferably applied by depositing a drop of this solution on the surface of the precursor of the anti-fog coating and then spreading it so as to cover preferably all of said precursor coating.
- the applied surfactant solution is generally an aqueous solution, preferably containing from 0.5 to 10%, more preferably from 2 to 8% by weight of surfactant.
- a commercial cleaning solution containing a surfactant available in the form of a spray or wipes, is used.
- surfactants can be used. These can be ionic (cationic, anionic or amphoteric) or nonionic, preferably nonionic or anionic. However, a mixture of surfactants belonging to these different categories is possible. These surfactants are for the most part commercially available.
- a surfactant having poly (oxyalkylene) groups is used.
- nonionic surfactants usable in the present invention include poly (alkyleneoxy) alkyl ethers, including poly (ethyleneoxy) alkyl-ethers, for example sold by ICI under the names BRU ®, poly (alkyleneoxy) alkylamines, polyalkylenoxyalkylamides, polyethoxylated, polypropoxylated or polyglycerolated fatty alcohols, polyethoxylated, polypropoxylated or polyglycerolated fatty alpha-diols, polyethoxylated, polypropoxylated or polyglycerolated fatty alkylphenols and polyethoxylated, polypropoxylated or polyglycerolated fatty acids all having a fatty chain comprising, for example, 8 to 18 carbon atoms, the number of ethylene oxide or propylene oxide groups being able to range, in particular, from 2 to 50, and the number
- Preferred anionic surfactants are those comprising a sulfonic acid group, mention may be made of alkylsulfosuccinates, alkylethersulfosuccinates, alkylamidesulfosuccinates, alkylsulfosuccinamates, dibasic salts of polyoxyethylene alkylsulphosuccinic acid, dibasic salts of alkylsulphosuccinic acid, alkylsulphoacetates.
- salts of sulfosuccinic acid half-esters, alkyl sulphates and aryl sulphates such as sodium dodecylbenzene sulphonate and sodium dodecyl sulphate, ethoxylated fatty alcohol sulphates, alkyl ether sulphates, alkyl amido ether sulphates, alkyl aryl polyether sulphates, alkyl sulphonates, alkyl phosphates, alkyl ether phosphates, alkyl amide sulfonates, alkylarylsulfonates, ⁇ -olefin sulfonates, ethoxysulfates of secondary alcohols, polyoxyalkylenated carboxylic ether acids, sulphates of monoglyceride, polyoxyethylene alkyl ether salts of sulfuric acid, salts of lake Sulfuric acid, N-acyltaurates such as N-acylmethyltaurine
- cationic surfactants that may be used in the present invention, mention may be made of the salts of primary, secondary or tertiary fatty amines, optionally polyoxyalkylenated, quaternary ammonium salts such as chlorides or bromides of tetraalkylammonium, alkylamidoalkyltrialkylammonium, trialkylbenzylammonium , trialkylhydroxyalkylammonium or alkylpyridinium, imidazoline derivatives or cationic amine oxides.
- quaternary ammonium salts such as chlorides or bromides of tetraalkylammonium, alkylamidoalkyltrialkylammonium, trialkylbenzylammonium , trialkylhydroxyalkylammonium or alkylpyridinium, imidazoline derivatives or cationic amine oxides.
- the surfactant used comprises a fluorinated surfactant.
- those having at least one fluoroalkyl or polyfluoroalkyl group and preferably those comprising at least one perfluoroalkyl group are preferably used.
- a commercially available surfactant solution for imparting antifogging property is Clarity Defog it ® solution from Nanofilm.
- hydrophilic compounds instead of a surfactant solution, it is possible to use hydrophilic compounds, more particularly compounds without surfactant properties comprising at least one hydrophilic group, preferably a poly (oxyalkylene) group, but the surfactant solutions are preferred. and give much better anti-fogging results than solutions based on non-surfactant hydrophilic compounds.
- the anti-fog coating of the invention preferably has a static contact angle with water of less than or equal to 10 °, more preferably less than or equal to 5 °.
- the anti-fogging effect exerted by the anti-fog coating is durable over time, since it is exercised for a period of time ranging from several days to several weeks, which is a clear improvement over known anti-fogging coatings. This durability is tested during mechanical stress corresponding to repeated wiping, in a procedure described in the experimental part.
- the anti-fog coating is temporary but easily renewable, since it is sufficient to carry out a new surfactant application when there are not enough surfactant molecules adsorbed on the surface of the precursor of the anti-fog coating. The latter therefore remains “activatable” in all circumstances.
- the optical article according to the invention does not have an antifouling coating, in particular no anti-fouling coating based on fluorinated silanes, but it turns out that it nevertheless has a satisfactory cleanability. Its ease of cleaning traces of sebum is worse than that of a fluoride antifouling coating, but better than that of a bare antireflection coating, that is to say without an antifouling coating. However, the ease of application of temporary anti-fogging products on the anti-fogging precursor according to the invention is greater than on the fluorinated antifouling coatings generally used. In addition, the durability of the anti-fogging effect obtained with a temporary anti-fogging product is better in the context of the invention than when this anti-fogging product is applied to an anti-fouling coating.
- the invention also relates to a method for preparing an optical article, preferably a spectacle lens, as defined above, comprising:
- This method may further comprise an additional step of depositing a film of a liquid solution containing at least one surfactant on the surface of the layer formed in step b), thus giving access to an anti-fog coating.
- the precursor coating of the anti-fog coating is not subjected to prolonged heating before the application of said liquid solution containing at least one surfactant. Heating the precursor coating at 50-60 ° for several hours could damage the optical article. Moreover, during the deposition of the precursor of the anti-fog coating, there is no need to heat the optical article.
- the invention finally relates to an optical article, preferably a spectacle lens, comprising a substrate coated with a coating having on its surface silanol groups, a part of the surface of said coating having on its surface silanol groups being direct contact with a precursor coating of an anti-fog coating as defined above, and another part of the surface of said coating having on its surface silanol groups, preferably the remainder of its surface, being in direct contact with and adhering to a hydrophobic and / or oleophobic coating.
- These parts can be continuous or discontinuous.
- Such an optical article can be used in particular as a demonstration article of anti-fogging properties, after application to its surface of a liquid solution containing at least one surfactant and / or a hydrophilic compound without surfactant properties as defined above, then exposing the article at conditions generating fog (breath, refrigerator, steam boiling ...) or by subjecting its surface to one or more wiping (s) before exposure to the conditions generating fogging.
- fog fog
- refrigerator steam boiling
- the optical article is misted on the part of the surface coated with hydrophobic and / or oleophobic coating and remains transparent in the area comprising the anti-fog coating.
- the hydrophobic and / or oleophobic coatings, or top-coats antifouling, used in this optical article are described in particular in the application WO 2010/055261. They are naturally different from the anti-fogging coatings of the invention.
- the hydrophobic and / or oleophobic coatings used preferably have a surface energy of less than or equal to 14 mJ / m 2 , preferably less than or equal to 12 mJ / m 2 , according to the Owens Wendt method described in the article referenced in WO2010 / 055261.
- Such an optical article can be formed, without the invention being limited to such a method, by using an optical article coated with a coating having on its surface silanol groups, at least a portion of the surface of said coating being coated directly with a hydrophobic and / or oleophobic coating, by subjecting at least a portion of said hydrophobic and / or oleophobic coating to a treatment to remove it, so as to expose the undercoating jacent having on its surface silanol groups, then depositing on the surface thus exposed at least one organosilane compound according to the invention, so as to form a precursor coating of an anti-fog coating as described above.
- any chemical or physical means for removing a portion of the hydrophobic and / or oleophobic coating may be used. It is preferable to use argon ion bombardment of the coating with an ion gun, but also vacuum plasma, corona discharge, electron beam bombardment or UV treatment. under conditions easily determinable by those skilled in the art. If the optical article comprises an electroconductive layer, in particular a conductive layer conferring antistatic properties in an antireflection coating, ionic bombardment is preferably used to avoid damage to the article.
- protection means such as a mask or any other appropriate technique, disposed on the surface of the article to be treated or possibly interposed between the source and the surface to be treated in the case of treatment with energetic species such as ions, photons or electrons.
- optical masks are conventional, and is described in particular in US Patent 5,792,537.
- the aforementioned optical article can be manufactured from a lens coated with a coating according to the invention, the surface containing silanol groups is partially exposed according to the method described above, and then deposit on the exposed surface a hydrophobic and / or oleophobic coating.
- the silica is used in the form of granules supplied by Optron Inc.
- the organosilane compound used in the examples to form the precursor of the anti-fog coating is 2- [methoxy (polyethyleneoxy) propyl] trimethoxysilane having 6 to 9 ethylene oxide units. (Examples 1-4, 6, 7), of formula (III) and molecular weight 450-600 g / mol (CAS No. 65994-07-2, Ref: SIM6492.7, supplied by Gelest, Inc. .), or 2- [methoxy (polyethyleneoxy) propyl] trimethoxysilane having 3 ethylene oxide units (Example 5), of formula (VIII).
- the comparative organosilane compounds used in Comparative Examples C4 to C7 are 2- [methoxy (polyethyleneoxy) propyl] triethoxysilane having 45 ethylene oxide units of the formula CH 3 0- (CH 2 CH 2 0) 4 5- (CH 2 ) 2 ) 3 Si (OC 2 H 5) 3 (IX), provided by Interchim, or the compound HO (CH 2 CH 2 O) 4 5 CONH (CH 2 ) 3 Si (OCH 2 CH 3 ) 3 (X), supplied by ABCR (CAS No. 37251-86-8).
- the compound of formula (X) is the compound used in Comparative Example 3 of JP 2005-281143.
- the glasses used in the examples according to the invention comprise a planar polythiourethane lens substrate (thermosetting PTU marketed by Mitsui Toatsu Chemicals), with a refractive index equal to 1.60, 65 mm in diameter, power -2.00 diopters and thickness 1, 2 mm.
- thermosetting PTU thermosetting PTU marketed by Mitsui Toatsu Chemicals
- This substrate is coated with an anti-abrasion and anti-scratch coating having a refractive index equal to 1.60, as well as a monolayer antireflection coating approximately 100 nm thick and having a refractive index equal to 1, 40, obtained by a sol-gel process (denoted antireflection coating X) (obtained by depositing an alkoxysilane composition comprising hollow colloidal particles, heated after deposition for 3 hours at 100 ° C.), or of a Zr0 2 / Si0 2 / Zr0 2 / Si0 2 tetracouche commercial anti-reflective coating (denoted antireflection coating Z) deposited on the anti-abrasion coating by vacuum evaporation of the materials in the order in which they were cited (respective thicknesses of the layers: 27, 21, 80 and 81 nm).
- the glasses comprising the antireflection coating X are subjected to a surface activation treatment by plasma (0.2 mbar, 200 ml 0 2 / min, 2 min at 500 W and then 5 min at 0 W).
- the glasses comprising the anti-reflective coating Z do not undergo any activation treatment.
- the glass used comprises a lens substrate made of ORMA ® material, comprising a polyurethane shockproof primer with a thickness of the order of 1 micron, itself coated with an anti-abrasion-resistant coating. a thickness of the order of 3 microns by depositing and curing a composition as defined in Example 3 of Patent EP 614957, in turn coated (except Example 4) with a five-layer anti-reflective coating Zr0 2 / SiO 2 / Zr0 2 / ITO / Si0 2 (denoted antireflection coating Y) deposited on the anti-abrasion coating by vacuum evaporation of the materials in the order in which they were cited (respective thicknesses layers: 29, 23, 68, 7 and 85 nm).
- An ITO layer is an electrically conductive layer of indium oxide doped with tin (In 2 0 3 : Sn).
- the glasses comprising the anti-abrasion coating are subjected to a surface activation treatment which consists in carrying out an ion bombardment with a rare gas or oxygen, in this case a gas rare which is argon, under vacuum, at a pressure typically of 3.5.10 ⁇ 5 mbar.
- a surface activation treatment which consists in carrying out an ion bombardment with a rare gas or oxygen, in this case a gas rare which is argon, under vacuum, at a pressure typically of 3.5.10 ⁇ 5 mbar.
- the antireflection coating is not subjected to any activation treatment before the deposition of the precursor of the anti-fog coating.
- the anti-fog coating precursor has been deposited according to two different methods:
- siloxane compound of formula III 1 g is diluted in 9 g of isopropanol. 4 g of the resulting solution are then diluted in 145 g of isopropanol. The solution is stirred for 2 minutes at room temperature and then slightly acidified with 0.2 g of 0.1 N HCl and finally deposited by centrifugal deposition (3000 rpm / 30 sec / acceleration: 2000 rpm / s, 50% humidity). on the antireflection coating X of a lens whose surface has been activated as indicated above. The precursor of the anti-fog coating is then heated for 15 minutes at 75 ° C and then 3 hours at 100 ° C.
- Example 2 the deposition is carried out on the antireflection coating Z of a vacuum evaporation lens using a Joule heat source.
- 150 ⁇ l of siloxane compound of formula III are impregnated in a nickel foam in a copper capsule (deposited thickness: 10 nm, deposition rate: 0.25 nm / s, pressure at start of the deposit: 2.10 "5 mBar).
- each lens is wiped with dry cloth until the surplus of siloxane compound of formula III deposited is removed. We then observe a homogeneous surface.
- the anti-fog coating of Example 2 has a thickness of 1 -3 nm.
- the Cémoi TM fabric designates a fabric supplied by the supplier Facol under the reference Microfibre M8405 30x40.
- Example 4 the deposition is carried out on the anti-abrasion coating of a lens by vacuum evaporation using a Joule effect heat source.
- the siloxane compound of formula III is poured into a copper capsule (in the absence of porous material), and this capsule is deposited on a heating support as a conductive tantalum.
- the evaporation device is a SATIS 1200 DLF machine.
- the evaporation pressure of the siloxane compound of formula III generally ranges from 5 ⁇ 10 -6 to 8 ⁇ 10 -6 mbar.
- each lens is rinsed with soapy water, optionally isopropyl alcohol, then deionized water and wiped with a dry Cémoi TM fabric so that the excess of siloxane compound of deposited formula III is evacuated.
- Example 5-6 the deposition is carried out on the anti-reflection coating Y of a vacuum evaporation lens according to a protocol similar to that of Example 4, using an organosilane of formula III or VIII, with a speed of programmed evaporation of 0.3 nm / s. A layer approximately 12 nm thick (before removal of the excess siloxane compound) is obtained, which is optionally heated for 1 hour at 60 ° C. (only for Examples C6 and O1). The excess of siloxane compound is then removed as described for Example 4. c) Comparative Examples
- the glasses of Comparative Example C1 differ from those of Example 1 in that they do not include antifogging precursor.
- the glasses of Comparative Example C2 differ from those of Example 2 in that they do not include antifogging precursor.
- the glasses of Comparative Example C3 differ from those of Comparative Example C2 in that an antifouling coating of 2-3 nm thick is formed on the antireflection coating by vacuum evaporation from the OPTOOL DSX ® composition.
- an antifouling coating of 2-3 nm thick is formed on the antireflection coating by vacuum evaporation from the OPTOOL DSX ® composition.
- Daikin Industries fluororesin comprising perfluoropropylene groups corresponding to the formula of US Pat. No. 6,183,872).
- the glasses of Comparative Examples C4 to C7 have an anti-fog coating precursor coating formed from an organosilane compound not in accordance with the invention because of a polyoxyalkylene group comprising more than 80 carbon atoms. d) Application of a liquid solution containing a surfactant (temporary anti-fog solution)
- Example 4A have anti-fogging properties comparable to those of Examples 1A and 2A. e1) Evaluation of the anti-fog properties
- Anti-fogging properties can be evaluated in three ways: by the "breath test” (qualitative test that does not use a visual acuity measurement), by the “hot steam” test and by the test " of the refrigerator ". Breath and refrigerator tests are considered to generate low fogging. The hot steam test is considered to generate a strong fogging stress. Breath test
- the tester places the glass to be evaluated about 2 cm from his mouth.
- the tester blows his breath for 3 seconds on the exposed surface of the glass.
- the tester visually observes the presence of a veil of condensation / distortion or not.
- the lenses are placed 24 hours in a temperature controlled environment (20-25 q C) and humidity of 50%.
- the glasses are placed 15 seconds above a heated container containing water at 55 ° C. Immediately afterwards, a visual acuity scale at 5 m is observed through the tested glass. The observer assesses visual acuity as a function of time and according to the following criteria:
- This test simulates the living conditions where a wearer places his face above his tea, coffee or a pot of boiling water.
- the glasses are placed in a hermetically sealed box containing a desiccant (silica gel).
- the boxes are themselves placed at least 24h in a refrigerator at 4 ⁇ C. After this time, the boxes are removed from the refrigerator and the glasses are immediately tested. These are placed in an atmosphere of 45-50% moisture and 20-25%.
- a visual acuity scale of 4 m is observed through the glass. The observer evaluates the visual acuity as a function of time and according to the same criteria as the hot steam test (scores 0, 1 or 2).
- FIG. 1 The results of the hot steam test are shown in FIG. It can be seen that only the glasses of Examples 1A and 2A constitute anti-fogging lenses within the meaning of the invention. They are also immediately operational. Glasses devoid of hydrophilic surface coating (Examples C2 and C3) and glasses equipped with an anti-fog coating precursor coating do not constitute anti-fogging lenses within the meaning of the invention, because they present a visual distortion that does not allow one to visual acuity> 6/10 th after exposure to hot steam. Nevertheless, the glasses of Examples 1 and 2 have anti-fogging properties in the context of the breath test.
- Non-fogging lenses eventually lead to a visual acuity of 10/10, due to the evaporation of water vapor. e2) Evaluation of properties of ease of cleaning (cleanability)
- Example C3 The glasses tested and the results are shown in Table 1 and show that the glass easier to clean is naturally the one with a fluoride antifouling coating (example C3).
- the glasses comprising an anti-fogging precursor according to the invention (Examples 1 and 2) are easier to clean than those which do not contain them, or equivalent to those (Examples C1 and C2), having an uncoated antireflection coating.
- Examples 1 and 2 are easier to clean than those which do not contain them, or equivalent to those (Examples C1 and C2), having an uncoated antireflection coating.
- the deposition of the temporary anti-fog solution is carried out as many times as necessary so that, at the initial moment, all the glasses are considered as anti-fogging at the end of the hot vapor test described above.
- the glasses are then wiped with a Cémoi cloth and again subjected to the hot steam test. (The glasses are wiped when the film of water due to fog has disappeared.If the glasses are wiped while the film of water is still present, partially remove the anti-fog solution).
- Wiping corresponds to two very strong rotations of a Cémoi cloth on the surface of the glass.
- the notes (0, 1 or 2) correspond to the level of steam at the exit of the second test with hot steam, after the corresponding number of wiping.
- Example C3 On a hydrophobic surface (example C3), wiping is sufficient to completely damage the anti-fogging properties provided by the Defog It temporary solution. On a more hydrophilic surface (surface of the antireflection coating of Example C1), 5 wiping is necessary to begin to observe a deterioration of the anti-fogging properties provided by the temporary solution Defog It.
- An anti-fog coating according to the invention therefore makes it possible to significantly improve the durability of the anti-fogging property provided by a temporary anti-fogging solution with respect to mechanical wiping. e5) Durability of the anti-fogging effect (after application of the Defog It solution)
- the reflection spectra of glasses were made before and after the deposition of the temporary solution Defog It. Each of the glasses has anti-fogging properties after the breath test after application of this solution.
- Table 3 shows the variations observed on the reflection spectra after depositing the Defog It temporary solution.
- the articles resulting from a modification of their surface by grafting the organosilane of formula III (before depositing the surfactant solution) retain antireflection properties corresponding to the criteria of the ophthalmic industry.
- a silicon substrate wafer was used rather than a lens in order to be able to measure the thicknesses of the deposited layers with greater precision.
- the optical article used in this example comprises a silicon substrate coated with a silica layer of 50 nm thick deposited in the vapor phase (programmed thickness: 140 nm, programmed deposition rate: 3 nm / s).
- This silica layer has after 3 days of its deposit a static contact angle with water of 33 °, evolving up to 43 ° in 2-3 months.
- the surface of the article is washed with soapy water and wiped with a dry Cémoi fabric. This gives a coating having a thickness of 1-3 nm and a homogeneous surface, and having a static contact angle with water of 39 °.
- the durability of the anti-fog coating was evaluated by performing 50 dry wiping of the surface of the optical article with a Cémoi cloth (50 roundtrip). After this operation, the article has a static contact angle with the water of less than 3 °, which shows that the temporary solution "Defog It" is still present on its surface.
- the thicknesses were determined by ellipsometry monolongeur wave considering that the overall refractive index of the silica / precursor bilayer of the anti-fog coating is equal to 1, 45. 5.
- This test evaluates the wiping resistance of the temporary anti-fog solution on the surface of the glasses. It is performed on two samples of each glass.
- the glasses After each hot steam test, the glasses should be dried at room temperature, so that the water film due to steam has disappeared. Indeed, if we wipe the glasses while the film of water is still present, we partially remove the anti-fog solution.
- the glasses are then manually wiped dry with a Cémoi cloth (2 wiping) and subjected a second time to the hot steam test, then dried as described. previously. Wiping corresponds to two very strong rotations of a Cémoi cloth on the surface of the glass.
- the glasses are then manually wiped dry with a Cémoi cloth (3 additional wiping) and submitted a third time to the hot steam test, which allows the attribution of the anti-fogging note after 5 wiping, then dried as described above.
- This cycle is repeated so as to be able to assign an anti-fogging score after 10 and 20 cumulative wiping, by performing a series of 5 and then a series of 10 additional wiping, separated by a drying step.
- the anti-fogging notes correspond to the steam level at the end of each hot steam test, after the corresponding number of wipings (cumulative number):
- Glasses are considered to have successfully passed the durability test if they are rated A or B.
- organosilane compounds according to the invention make it possible to form better anti-fogging coatings than the comparative compounds of formulas IX and X used in the prior art, which have a polyoxyalkylene chain which is too long.
- This result is surprising insofar as the compounds IX and X make it possible to form more hydrophilic coatings than the compounds III and VIII, and that it is generally expected to obtain better anti-fogging properties by increasing the hydrophilicity of a coating.
- Compound III is also significantly more efficient than compound VIII.
- a glass of ORMA ® material comprising on its concave and convex faces the same functional coatings as those of Examples 5-6, namely a shockproof polyurethane primer, an anti-abrasion coating and the anti-reflective coating Y (Zr0 2 / Si0 2 / Zr0 2 / ITO / Si0 2) is coated by vacuum evaporation on both sides with a layer of antifouling coating 2 nm thick based on the Optool DSX material ® from Daikin Industries.
- a mask made by laser cutting a plastic film so as to form a pattern, is then disposed on its convex face.
- the convex face partially protected by the mask is then exposed to argon ion bombardment by an ion gun, which has the effect of removing the antifouling coating in the pattern-protected, unprotected area, and exposing in this zone the outer layer of the antireflection coating Y, which is a layer of silica.
- the vaporization coating precursor deposition is then carried out in the exposed zone in the same manner as for Examples 5-6, using the organosilane of formula III, and holding the mask on the glass surface during deposition, so as to form a graft layer of antifogging coating precursor coating 2 to 3 nm thick.
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Abstract
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Priority Applications (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EA201200976A EA022678B1 (ru) | 2009-12-31 | 2010-12-22 | Оптическое изделие, содержащее временное противозапотевающее покрытие, характеризующееся улучшенной долговечностью |
CN201080060032.0A CN102686527B (zh) | 2009-12-31 | 2010-12-22 | 包含具有改进的耐久性的临时性防雾涂层的光学制品 |
JP2012546491A JP5965321B2 (ja) | 2009-12-31 | 2010-12-22 | 改善された耐久性を備える一時的防曇被覆を含む光学物品 |
KR1020127013832A KR101764280B1 (ko) | 2009-12-31 | 2010-12-22 | 향상된 내구성을 갖는 일시적 김서림-방지 코팅을 포함하는 광학 제품 |
PL10808928T PL2519474T3 (pl) | 2009-12-31 | 2010-12-22 | Wyrób optyczny, zawierający czasową powłokę przeciwdziałającą zaparowaniu, mającą zwiększoną trwałość |
ES10808928.5T ES2539711T3 (es) | 2009-12-31 | 2010-12-22 | Artículo de óptica que incluye un revestimiento anti-vaho temporal que tiene una durabilidad mejorada |
CA2785908A CA2785908C (fr) | 2009-12-31 | 2010-12-22 | Article d'optique comportant un revetement antibuee temporaire ayant une durabilite amelioree |
US13/260,697 US8709588B2 (en) | 2009-12-31 | 2010-12-22 | Optical article comprising a temporary anti-fogging coating with improved durability |
IN5119DEN2012 IN2012DN05119A (fr) | 2009-12-31 | 2010-12-22 | |
EP20100808928 EP2519474B1 (fr) | 2009-12-31 | 2010-12-22 | Article d'optique comportant un revetement antibuee temporaire ayant une durabilite amelioree |
AU2010338060A AU2010338060B2 (en) | 2009-12-31 | 2010-12-22 | Optical article comprising a temporary anti-fogging coating with improved durability |
BR112012016406A BR112012016406B1 (pt) | 2009-12-31 | 2010-12-22 | artigo óptico compreendendo um revestimento anti-embaçante temporário com durabilidade melhorada |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
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FR0959685A FR2954832A1 (fr) | 2009-12-31 | 2009-12-31 | Article d'optique comportant un revetement antibuee temporaire ayant une durabilite amelioree |
FR0959685 | 2009-12-31 | ||
FR1053269A FR2954833B1 (fr) | 2009-12-31 | 2010-04-28 | Article d'optique comportant un revetement antibuee temporaire ayant une durabilite amelioree |
FR1053269 | 2010-04-28 |
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WO2011080472A2 true WO2011080472A2 (fr) | 2011-07-07 |
WO2011080472A3 WO2011080472A3 (fr) | 2011-08-25 |
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PCT/FR2010/052895 WO2011080472A2 (fr) | 2009-12-31 | 2010-12-22 | Article d'optique comportant un revetement antibuee temporaire ayant une durabilite amelioree |
Country Status (15)
Country | Link |
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US (1) | US8709588B2 (fr) |
EP (1) | EP2519474B1 (fr) |
JP (1) | JP5965321B2 (fr) |
KR (1) | KR101764280B1 (fr) |
CN (1) | CN102686527B (fr) |
AU (1) | AU2010338060B2 (fr) |
BR (1) | BR112012016406B1 (fr) |
CA (1) | CA2785908C (fr) |
EA (1) | EA022678B1 (fr) |
ES (1) | ES2539711T3 (fr) |
FR (2) | FR2954832A1 (fr) |
IN (1) | IN2012DN05119A (fr) |
PL (1) | PL2519474T3 (fr) |
PT (1) | PT2519474E (fr) |
WO (1) | WO2011080472A2 (fr) |
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BR112012016406B1 (pt) | 2020-04-14 |
KR101764280B1 (ko) | 2017-08-03 |
EA022678B1 (ru) | 2016-02-29 |
EP2519474A2 (fr) | 2012-11-07 |
IN2012DN05119A (fr) | 2015-10-23 |
CN102686527A (zh) | 2012-09-19 |
JP2013516638A (ja) | 2013-05-13 |
US20120019767A1 (en) | 2012-01-26 |
PT2519474E (pt) | 2015-07-21 |
FR2954833A1 (fr) | 2011-07-01 |
EP2519474B1 (fr) | 2015-04-01 |
AU2010338060A1 (en) | 2012-07-12 |
EA201200976A1 (ru) | 2012-12-28 |
WO2011080472A3 (fr) | 2011-08-25 |
FR2954833B1 (fr) | 2013-03-22 |
JP5965321B2 (ja) | 2016-08-03 |
US8709588B2 (en) | 2014-04-29 |
CA2785908C (fr) | 2018-09-11 |
BR112012016406A2 (pt) | 2018-05-15 |
FR2954832A1 (fr) | 2011-07-01 |
PL2519474T3 (pl) | 2015-08-31 |
CA2785908A1 (fr) | 2011-07-07 |
CN102686527B (zh) | 2015-08-05 |
KR20120107084A (ko) | 2012-09-28 |
ES2539711T3 (es) | 2015-07-03 |
AU2010338060B2 (en) | 2015-01-22 |
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