WO2011070293A1 - Substrat hydrophobe comprenant un double primage - Google Patents
Substrat hydrophobe comprenant un double primage Download PDFInfo
- Publication number
- WO2011070293A1 WO2011070293A1 PCT/FR2010/052641 FR2010052641W WO2011070293A1 WO 2011070293 A1 WO2011070293 A1 WO 2011070293A1 FR 2010052641 W FR2010052641 W FR 2010052641W WO 2011070293 A1 WO2011070293 A1 WO 2011070293A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- layer
- substrate
- hydrophobic
- priming
- glass
- Prior art date
Links
Classifications
-
- 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
- C03C17/34—Surface treatment of glass, not in the form of fibres or filaments, by coating with at least two coatings having different compositions
- C03C17/42—Surface treatment of glass, not in the form of fibres or filaments, by coating with at least two coatings having different compositions at least one coating of an organic material and at least one non-metal coating
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/009—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone characterised by the material treated
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
- C04B41/52—Multiple coating or impregnating multiple coating or impregnating with the same composition or with compositions only differing in the concentration of the constituents, is classified as single coating or impregnation
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/80—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone of only ceramics
- C04B41/81—Coating or impregnation
- C04B41/89—Coating or impregnation for obtaining at least two superposed coatings having different compositions
-
- 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
- C03C2217/76—Hydrophobic and oleophobic coatings
Definitions
- the present invention relates to a hydrophobic substrate, in particular consisting of a glass material, a ceramic, a glass-ceramic and so on.
- the glazings according to the invention are preferably glass panes. They are used, in particular, in the aeronautical, railway or automobile field. They can also be used in the field of building or in the field of interior design such as, for example, decorative panels, furniture, appliances (doors of refrigerators or ovens, showcases) and so on.
- This type of treatment aims in a known manner to give the substrate the character of non-wettability, called anti-rain in some areas.
- Wettability refers to the property that polar or nonpolar liquids adhere to the substrate forming a film. This adhesion is also valid for dust or dirt of all kinds (fingerprints, insects, etc.). The presence of water and / or dirt is troublesome, in particular for a transparent substrate of the glazing type, in particular used in the field of transport.
- the property of non-wettability of a substrate is characterized by a contact angle between water and this high substrate.
- the contact angle when a drop of water is deposited on a flat solid surface, is defined as the angle formed between the tangent to the drop at the point of contact and said solid surface.
- the substrate is considered to have hydrophobic properties when said contact angle is initially greater than 90 °, preferably greater than 100 °.
- the liquid When the substrate has such hydrophobicity properties, the liquid then has a tendency to flow easily, in the form of drops, on the substrate, by simple gravity if the substrate is inclined, or under the effect of aerodynamic forces in the case of a moving vehicle.
- Agents known to give this hydrophobicity property are, for example, fluorinated alkylsilanes as described in the patent applications EP 0 492 417, EP 0 492 545 and EP 0 672 779. According to these documents, the hydrophobic layer can be obtained by applying to the surface of a substrate a solution containing fluorinated organosilanes in an organic solvent.
- EP 0 492 545 cites, in particular, n-hexadecane, toluene, xylene, etc. These solvents are particularly suitable for a fluorinated chlorosilane. It is also possible, according to this document, to use a methyl or ethyl alcohol as a solvent.
- Common hydrophobic agents are, in particular, alkylsilanes whose alkyl group has at least one perfluorinated end, that is to say consisting of a group F3C- (CF2) n -, in which n is a positive integer or no.
- Patent EP 944 687 more particularly describes liquid-developed rain coatings and comprising an underlayer or priming layer obtained from a precursor of the Si (OEt) 4 or SiCl 4 type and a functional layer based on perfluoroalkylsilane.
- EP 1 102 825 discloses a composition for a hydrophobic coating incorporating in the same layer both a fluorinated alkylsilane and a bis-silane.
- the application WO 2007/012779 alternately describes a hydrophobic coating consisting of a first bis-silane priming layer and a layer with hydrophobic properties incorporating a fluorinated alkylsilane.
- the main subject of the present invention is thus coatings resistant not only to abrasion and to UV radiation but also having a high chemical inertia, ie a chemical inertia that enables them to fulfill the specifications imposed on them. currently the automotive industry, especially in terms of salt corrosion.
- the substrates comprising the coatings according to the invention have performances substantially equal to or greater than those of the hydrophobic substrates known at this date with regard to the other specifications necessary for their different uses, in particular the initial properties of hydrophobicity, mechanical strength or UV resistance.
- the present invention relates first of all to a process for obtaining a hydrophobic coating on a glass, ceramic, or glass-ceramic substrate, preferably glass, said method being characterized in that it comprises:
- R 3 represents a linear, branched or aromatic, preferably linear, carbon chain in which the number of carbons establishing the bond between the two silicon atoms is less than 6 and preferably is between 1 and 4, inclusive;
- R 1 and R 2 each represent an alkyl group or a hydrogen atom
- X 1 and X 2 are hydrolyzable groups, especially chosen from -Cl, -OCH 3 or -OC 2 H 5; preferably X 1 and X 2 are -OC 2 H 5,
- q and q ' are equal to 0 or 1, and preferably are zero
- the first layer of S102 may comprise between 1 and 10 mol% of Al.
- the first dense priming layer may be deposited by any technique known for this purpose, including magnetron techniques, thermal CVD type deposition techniques, PE-CVD or vacuum or atmospheric plasma. Other techniques are of course possible, provided that they allow the deposition of a sufficiently dense layer in the sense of the present invention.
- the dense sub-layer may according to the invention also undergo an etching operation to increase the roughness, according to the principles described in WO 2005/084943, in particular for obtaining an RMS roughness of said layer between 1 and 30 nm.
- the hydrophobic coating comprises or consists of at least one fluorinated alkylsilane.
- the step of depositing the hydrophobic coating is placed implemented from a solution comprising a perfluoroalkylsilane of formula:
- m 0 to 15, preferably 3 to 7;
- p 0, 1 or 2, preferably 0 or 1, very preferably 0;
- R is an alkyl group or a hydrogen atom
- X is a hydrolyzable group such as a halide group or an alkoxy group.
- the invention also relates to a glass, ceramic, vitroceramic, preferably glass, substrate that can be obtained by the process described above.
- Said substrate is coated with a hydrophobic coating, said coating comprising three layers:
- a first priming layer of the material S1O2 optionally comprising a member of the group consisting of Al, B, C or Zr, the density of said layer being at least 1.9 g / cm 3 and preferably at least 2 0 g / cm 3 directly applied to said substrate,
- a second priming layer directly applied to the first priming layer, comprising Si-R 3 -Si groups, R 3 being chosen from the group consisting of linear, branched, or aromatic, preferably linear, alkyl chains in in which the number of carbons establishing the bond between the two silicon atoms is less than 6 and preferably is between 1 and 4, inclusive limits,
- a coating layer with hydrophobic properties in connection with said priming layer comprising fluorinated groups.
- the number of carbons establishing the bond between two silicon atoms is meant, in the sense of the present description, the smallest number of carbon atoms allowing the smallest linear junction between two silicon atoms and not the total number of carbon atoms placed between the two silicas. This definition is particularly relevant when a branched or aromatic ring group is present between them.
- the first layer of S102 may comprise between 1 and 10 mol% of Al.
- said layer may have been etched as previously described, such that its RMS roughness is between 1 and 30 nm.
- the coating layer with hydrophobic properties comprises or consists of an alkylsilane with a hydrophobic perfluorinated end.
- alkylsilane with perfluorinated end may be of the type represented by the general formula:
- m 0 to 15, preferably 3 to 7;
- the thickness of the layer with hydrophobic properties is between 1 and 100 nm, preferably between 1 nm and 10 nm.
- the thickness of the first dense priming layer may be between 1 nm and 100 nm, preferably between 2 nm and 80 nm.
- the thickness of the second bis-silane priming layer may be between 1 and 15 nm, preferably between 2 and 10 nm.
- the product of the invention is for example a monolithic glazing, laminated or multiple.
- “Monolithic glazing” means glazing consisting of a single sheet of glass
- laminated glazing a stack of several sheets integral with one another, for example sheets of glass or plastics fixed to each other by means of adhesive layers of polyvinyl butyral, polyurethane ...;
- multiple glazing an assembly of disjointed sheets, that is to say in particular separated from each other by layers of air.
- hydrophobic coating of the invention allows the flow of drops of water or other liquid on vertical or inclined surfaces, possibly under the effect of aerodynamic forces for example in the case of a moving vehicle.
- these flowing drops include dirt and drag them.
- the visibility through the glazing is improved to a degree that we can dispense in some cases cleaning devices (windshield wipers, windshield wipers).
- glazing for transport vehicles (automobile side windows, aviation or automobile windscreens) or for the building;
- - as a screen, including a television screen, touch screen, plasma screen.
- a first sample El according to the teaching of the application WO2007 / 012779 is prepared. More precisely, 0.3% of bis (triethoxysilyl) ethane (C 2 H 5 O) 3 Si (CH 2) 2 Si (OC 2 H 5) 3 is added to a solution comprising 90% of isopropanol and 10% of 0.3 N hydrochloric acid.
- the solution based on bis (triethoxysilyl) ethane is first deposited by ragging (4 cross passes) on a glass substrate previously polished with a cerium oxide solution and then thoroughly rinsed with demineralised water.
- the thickness of the priming layer thus obtained is about 7 nm.
- the perfluorodecyltriethoxysilane solution is in turn deposited by the same scraping technique.
- the deposition of the hydrophobic layers of the perfluoroalkylsilane type is carried out by the well known technique of scraping, wherein the material or its precursor is deposited via a soaked cloth.
- the deposition was implemented by any other technique known for this purpose in the field, in particular by spraying, which also allows better control of the thickness of layers, by centrifugation, according to methods known in the art by the term spin-coating, by soaking (processes often called dip-coating) or by watering (often called flow-coating processes).
- Example 2 The same steps as previously described for Example 1 are reproduced for the preparation of the second sample E2, but the glass substrate is this time treated with a 0.3% Si (OC 2 H 5) 4 priming solution in a solution of 90 % isopropanol and 10% water, during the first deposition step.
- the density of the silica underlayer thus obtained is about 1.4 g / cm 3 .
- the substrate thus coated with the underlayer is then brought into contact by the scraping technique, at ambient temperature, with a 3% solution of CF 3 (CF 2 ) 7 (CH 2 ) 2 Si (OC 2 H 5 ) 3 in a mixture of 90% isopropanol and 10% water acidified with HCl to 0.3 N. After 15 minutes of waiting at room temperature, the excess fluorosilanes is removed by cleaning with isopropanol.
- the thickness of the hydrophobic layer obtained is approximately 6 nm.
- a third sample E3 is prepared comprising only a dense layer of silica SiO 2 comprising 8 mol% of aluminum, deposited by high pressure magnetron.
- the glass substrate is introduced into the vacuum chamber of a magnetron device so as to deposit on its surface a dense layer of silica 5 nm thick and density close to 2.0 g / cm 3 .
- the conditions of the magnetron deposition are as follows: a target of dimension 56 ⁇ 12.5 cm 2 , containing 92% by weight of silicon and 8% of aluminum, is used.
- the pressure in the chamber used for the deposition is set at 8 ⁇ bar (200 Pascals) with gas flow rates of 15 sccm of argon and 12 sccm of oxygen.
- the plasma is lit by increasing the DC power from 0 to 2000 W at 20 W / s.
- the sputtering of the target is carried out, consisting in applying for 3 minutes a power of 2000W with pulses of 40 kHz and 4 ⁇ between the pulses.
- the speed of movement of the substrate under the target is adjusted to obtain a thickness of 5 nanometers of the dense layer of SiO 2 .
- CF3 (CF2) 7 (CH2 ) 2Si (OC2Hs) 3 as previously described.
- a layer with hydrophobic properties is obtained in a manner similar to that already described in Examples 1 and 2 above.
- a first hydrophobic coating having two sublayers was deposited on the substrate.
- a first priming consisting of a dense 5 nm silica underlayer is first deposited according to the protocol described in Example 3.
- the density of the second silica layer thus obtained is about 1, 4.
- the substrate and its double silica priming are then brought into contact at room temperature with the same solution of CF3 (CF2) 7 (CH2) 2Si (OC2H5) 3 as previously described, and a layer with hydrophobic properties is obtained in a manner similar to that already described in the previous examples.
- a second coating was deposited on the substrate hydrophobic according to the invention having two priming sub-layers.
- a first priming consisting of a 5 nm dense silica underlayer is first deposited according to the protocol previously described in Example 3.
- the substrate and its double priming (dense silica + bis-silane) are then brought into contact at room temperature with the same solution of CF3 (CF2) 7 (CH2) 2Si (OC2H5) 3 as previously described and a layer with hydrophobic properties is obtained in a manner similar to that already described in the preceding examples.
- the resistance to abrasion obtained by the measurement of the residual contact angle of the water on the sample after the hydrophobic coating grafted on the substrate has been abraded according to the Opel® friction test, conducted on the samples with a hardness felt Hl, a load of 0.4 kg / cm 2 on a surface of 1.5 cm 2 , with a translation speed of 50 cycles / minute and a rotation speed of 6 turns / minute.
- a sample is considered satisfactory if the contact angle remains greater than 90 ° after 5000 cycles.
- the abrasion and UV resistance properties are substantially identical and comply with the standards, as shown by the results obtained for the Opel® and UV tests on the different samples.
- the sample E5 according to the invention comprising two priming sub-layers, a first dense silica and a second constituted by bis-silanes, shows a resistance to saline corrosion, measured by the BSN test, much higher than that of the E1 and E2 sample coatings characteristic of the hydrophobic substrates known hitherto.
- the choice of implementing two sublayers according to the invention, a first dense silica and a second constituted by bis-silanes surprisingly leads to coatings having surprisingly high hydrolytic strengths as it is reported in table 1.
- the experimental protocol used to obtain the sample according to Example 6 is identical in all respects to that already described in Example 3
- the experimental protocol used to obtain the sample. according to Example 7 is identical in all respects to that already described in Example 4
- the experimental protocol used to obtain the sample according to Example 8 is identical in all respects to that already described in the example 5.
- thicknesses of the order of a few nanometers, for example from 2 to 20 nm or even from 2 to 10 nm, of the dense silica underlayer are sufficient to obtain a much improved hydrolytic resistance. , which advantageously limits the industrial cost of a deposit on the substrate of two successive priming layers according to the invention.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP20100801640 EP2509923B1 (fr) | 2009-12-10 | 2010-12-08 | Substrat hydrophobe comprenant un double primage et procede de fabrication |
ES10801640.3T ES2542204T3 (es) | 2009-12-10 | 2010-12-08 | Sustrato hidrófobo que comprende una doble imprimación y procedimiento de fabricación |
CN201080054605.9A CN102666412B (zh) | 2009-12-10 | 2010-12-08 | 包括双重底漆的疏水基材 |
PL10801640T PL2509923T3 (pl) | 2009-12-10 | 2010-12-08 | Podłoże hydrofobowe zawierające podwójny podkład i sposób wytwarzania |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0958841A FR2953823B1 (fr) | 2009-12-10 | 2009-12-10 | Substrat hydrophobe comprenant un double primage |
FR0958841 | 2009-12-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2011070293A1 true WO2011070293A1 (fr) | 2011-06-16 |
Family
ID=42282613
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2010/052641 WO2011070293A1 (fr) | 2009-12-10 | 2010-12-08 | Substrat hydrophobe comprenant un double primage |
Country Status (8)
Country | Link |
---|---|
EP (1) | EP2509923B1 (zh) |
KR (1) | KR20120101678A (zh) |
CN (1) | CN102666412B (zh) |
ES (1) | ES2542204T3 (zh) |
FR (1) | FR2953823B1 (zh) |
PL (1) | PL2509923T3 (zh) |
PT (1) | PT2509923E (zh) |
WO (1) | WO2011070293A1 (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013104456A1 (de) | 2012-01-11 | 2013-07-18 | Saint-Gobain Glass France | Wischersteuerung |
GB2536285A (en) * | 2015-03-13 | 2016-09-14 | 3M Innovative Properties Co | Coating process |
US11779716B2 (en) | 2017-08-03 | 2023-10-10 | Kindeva Drug Delivery L.P. | Method for making medicinal delivery device having multi-layer coating |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101814859B1 (ko) | 2014-08-14 | 2018-01-04 | 주식회사 엘지화학 | 소수성 기판 및 이의 제조방법 |
KR102025712B1 (ko) * | 2015-03-13 | 2019-09-26 | 후아웨이 테크놀러지 컴퍼니 리미티드 | 외장 지르코니아 세라믹 부재 및 그 제조 방법 |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0492417A2 (en) | 1990-12-21 | 1992-07-01 | Matsushita Electric Industrial Co., Ltd. | Method of manufacturing chemically adsorbed film |
EP0492545A2 (en) | 1990-12-25 | 1992-07-01 | Matsushita Electric Industrial Co., Ltd. | Transparent substrate with monomolecular film thereon and method of manufacturing the same |
EP0672779A2 (en) | 1991-07-26 | 1995-09-20 | Matsushita Electric Industrial Co., Ltd. | Method of making a surface of a substrate water- and oilrepellent |
EP0944687A1 (fr) | 1997-10-06 | 1999-09-29 | Saint-Gobain Vitrage | Revetement hydrophobe notamment pour vitrage |
FR2781495A1 (fr) * | 1998-07-24 | 2000-01-28 | Saint Gobain Vitrage | Composition de traitement hydrophobe, procede de formation d'un revetement a partir de cette composition et produits munis de ce revetement |
EP1142845A1 (en) * | 2000-03-31 | 2001-10-10 | Matsushita Electric Industrial Co., Ltd. | Anti-contaminant coating film, producing method thereof, anti-contaminant glass for automobile, producing method thereof, and automobile employing the glass |
WO2005084943A2 (fr) | 2004-02-24 | 2005-09-15 | Saint-Gobain Glass France | Substrat, notamment verrier, a surface hydrophobe, avec une durabilite amelioree des proprietes hydrophobes. |
WO2007012779A2 (fr) | 2005-07-26 | 2007-02-01 | Saint-Gobain Glass France | Revetement hydrophobe comprenant un primage comprenant un bis-silane et une couche hydrophobe comprenant un alkylsilane fluore |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6737105B2 (en) * | 2001-07-27 | 2004-05-18 | Vtec Technologies, Inc. | Multilayered hydrophobic coating and method of manufacturing the same |
-
2009
- 2009-12-10 FR FR0958841A patent/FR2953823B1/fr not_active Expired - Fee Related
-
2010
- 2010-12-08 KR KR1020127014871A patent/KR20120101678A/ko not_active Application Discontinuation
- 2010-12-08 PT PT108016403T patent/PT2509923E/pt unknown
- 2010-12-08 PL PL10801640T patent/PL2509923T3/pl unknown
- 2010-12-08 EP EP20100801640 patent/EP2509923B1/fr active Active
- 2010-12-08 CN CN201080054605.9A patent/CN102666412B/zh not_active Expired - Fee Related
- 2010-12-08 ES ES10801640.3T patent/ES2542204T3/es active Active
- 2010-12-08 WO PCT/FR2010/052641 patent/WO2011070293A1/fr active Application Filing
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0492417A2 (en) | 1990-12-21 | 1992-07-01 | Matsushita Electric Industrial Co., Ltd. | Method of manufacturing chemically adsorbed film |
EP0492545A2 (en) | 1990-12-25 | 1992-07-01 | Matsushita Electric Industrial Co., Ltd. | Transparent substrate with monomolecular film thereon and method of manufacturing the same |
EP0672779A2 (en) | 1991-07-26 | 1995-09-20 | Matsushita Electric Industrial Co., Ltd. | Method of making a surface of a substrate water- and oilrepellent |
EP0944687A1 (fr) | 1997-10-06 | 1999-09-29 | Saint-Gobain Vitrage | Revetement hydrophobe notamment pour vitrage |
FR2781495A1 (fr) * | 1998-07-24 | 2000-01-28 | Saint Gobain Vitrage | Composition de traitement hydrophobe, procede de formation d'un revetement a partir de cette composition et produits munis de ce revetement |
EP1102825A1 (fr) | 1998-07-24 | 2001-05-30 | Saint-Gobain Glass France | Composition de traitement hydrophobe, procede de formation d'un revetement et produits munis de ce revetement |
EP1142845A1 (en) * | 2000-03-31 | 2001-10-10 | Matsushita Electric Industrial Co., Ltd. | Anti-contaminant coating film, producing method thereof, anti-contaminant glass for automobile, producing method thereof, and automobile employing the glass |
WO2005084943A2 (fr) | 2004-02-24 | 2005-09-15 | Saint-Gobain Glass France | Substrat, notamment verrier, a surface hydrophobe, avec une durabilite amelioree des proprietes hydrophobes. |
WO2007012779A2 (fr) | 2005-07-26 | 2007-02-01 | Saint-Gobain Glass France | Revetement hydrophobe comprenant un primage comprenant un bis-silane et une couche hydrophobe comprenant un alkylsilane fluore |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013104456A1 (de) | 2012-01-11 | 2013-07-18 | Saint-Gobain Glass France | Wischersteuerung |
US9061658B2 (en) | 2012-01-11 | 2015-06-23 | Saint-Gobain Glass France | Wiper control |
GB2536285A (en) * | 2015-03-13 | 2016-09-14 | 3M Innovative Properties Co | Coating process |
US11779716B2 (en) | 2017-08-03 | 2023-10-10 | Kindeva Drug Delivery L.P. | Method for making medicinal delivery device having multi-layer coating |
Also Published As
Publication number | Publication date |
---|---|
EP2509923A1 (fr) | 2012-10-17 |
CN102666412B (zh) | 2016-05-18 |
PT2509923E (pt) | 2015-09-01 |
FR2953823A1 (fr) | 2011-06-17 |
KR20120101678A (ko) | 2012-09-14 |
CN102666412A (zh) | 2012-09-12 |
EP2509923B1 (fr) | 2015-04-29 |
ES2542204T3 (es) | 2015-08-03 |
FR2953823B1 (fr) | 2011-12-02 |
PL2509923T3 (pl) | 2015-10-30 |
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