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WO2012008970A1 - Revêtement hydrophobe et procédé - Google Patents

Revêtement hydrophobe et procédé Download PDF

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Publication number
WO2012008970A1
WO2012008970A1 PCT/US2010/042297 US2010042297W WO2012008970A1 WO 2012008970 A1 WO2012008970 A1 WO 2012008970A1 US 2010042297 W US2010042297 W US 2010042297W WO 2012008970 A1 WO2012008970 A1 WO 2012008970A1
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WO
WIPO (PCT)
Prior art keywords
silane
group
amino
plasma
aminoethyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2010/042297
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English (en)
Inventor
Gaurav Saini
Matthew R. Linford
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Brigham Young University
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Brigham Young University
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Filing date
Publication date
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Priority to PCT/US2010/042297 priority Critical patent/WO2012008970A1/fr
Publication of WO2012008970A1 publication Critical patent/WO2012008970A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D5/00—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures
    • B05D5/08—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures to obtain an anti-friction or anti-adhesive surface
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D1/00—Processes for applying liquids or other fluent materials
    • B05D1/36—Successively applying liquids or other fluent materials, e.g. without intermediate treatment
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D2201/00—Polymeric substrate or laminate
    • B05D2201/02—Polymeric substrate
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/14—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by electrical means
    • B05D3/141—Plasma treatment
    • B05D3/142—Pretreatment
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D5/00—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures
    • B05D5/08—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures to obtain an anti-friction or anti-adhesive surface
    • B05D5/083—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures to obtain an anti-friction or anti-adhesive surface involving the use of fluoropolymers
    • B05D5/086—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures to obtain an anti-friction or anti-adhesive surface involving the use of fluoropolymers having an anchoring layer

Definitions

  • polymer/plastic materials have desirable bulk properties such as low density, low cost, good strength, and ease of processing that have allowed them to become integral components of countless consumer goods and devices.
  • plastics that have ideal bulk properties for certain applications are lacking in their surface properties, such as, for example, abrasion resistance and wetting.
  • various devices are designed to prevent water from entering interior portions of the devices in order to maintain proper functionality.
  • Manufacturers often design devices to be used in environments where water or other liquid materials may come into contact with the devices and components of the devices.
  • Devices and device components may have various protective coverings to protect interior portions of the devices and components.
  • the protective covering is made from multiple parts, resulting in various seams and openings that may expose interior portions to damage from liquids.
  • Many devices also require small openings or interstices in the protective cover in order to allow air or other gases to flow freely between the interior and exterior of the device while preventing liquids from passing through the cover.
  • a battery used in powering an electronic device may be susceptible to damage from moisture, and may nonetheless require an external source of oxygen to operate.
  • devices may contain a liquid material that is intended to be contained within the device for an extended time until the liquid is dispensed.
  • An ink jet cartridge for example, often contains a liquid ink solution that is contained within the cartridge for extended periods. Summary
  • An aspect of the invention involves treating a surface with an adhesion promoting compound or first silane or having at least one silane functional group and at least one amine group.
  • the surface formed by the first silane is then treated with a second silane.
  • Another aspect of the invention is treatment of a surface with a plasma to add an increased number of carboxyl groups to the surface before treatment of the hydrolyzed first silane with the amine group.
  • a plasma to add an increased number of carboxyl groups to the surface before treatment of the hydrolyzed first silane with the amine group.
  • Another aspect of the invention is a reaction product of a surface, a hydrolyzed first silane with an amine group and a second silane.
  • Another aspect of the invention is an article of manufacture comprising an article of a surface, a hydrolyzed first silane with an amine group and a second silane.
  • Devices that may be treated by the present invention are any devices that may benefit having hydrophobic surfaces. These include, but are not limited to,
  • anti-wetting/anti-fogging optical surfaces such as windows, vehicle windshields, lenses, optical devices, computer/led screens, and the like
  • apparel and other textile articles such as water-resistant outerwear (coats, jackets, liners, pants, gloves, footwear, socks, hats), stain resistant clothing, clothing (formal, casual, work, medical, athletic), carpeting & rugs, zipper fasteners, rope/cordage, camping equipment (tents, footprints, sleeping bags, sleeping pads, rain flies, screens, backpacks, dry bags, canopies), filters, upholstery, medical gowns, bedding (sheets, pillows, comforters, blankets, pillow cases, mattress pads, mattress covers, mattresses), Geotextiles, water sport apparel (swimming suits, wet suits, dry suits, Personal Flotation Devices, skull caps, booties, gloves), protective wear (chemical suites, bullet proof vests, firefighting apparel, helmets), and covers (pool covers, awnings, boat covers, protective covers)
  • water-resistant outerwear coats, jackets, liners, pants, gloves, footwear, socks, hats
  • stain resistant clothing clothing (formal, casual, work, medical, athletic), carpet
  • surfaces exposed to weather that may benefit from water resistance
  • building materials of any material such as synthetic or natural polymers (vinyl, wood, etc.), metals, and the doors and exterior surfaces of vehicles, such as cars, trains, and airplane, particularly for watercraft, and aircraft.
  • the coating may be useful on surfaces to mitigate accumulation of ice on aerodynamic or wing lifting surfaces and the like.
  • insulating materials such as feathers, hollow polymeric fibers, closed and open celled foam.
  • any device where a hydrophobic surface may be applicable is contemplated; including those listed in the Background, and other suitable devices, such as, for example, electronic equipment (both portable and nonportable devices), medical devices (such as tools, implants, diagnostic equipment, catheters), batteries, and fishing articles
  • Coating may be formed on portions of completed article assemblies, article sub-assemblies, individual articles, device components, and/or shell components. Coating may have a substantially consistent thickness respective to surface. Alternatively, coating may be applied to surface intermittently and/or in a specific pattern. Additionally, coating may be applied to surface only on desired portions of surface, such as, for example, portions of surface contacting or in close proximity to a seam, hole, interstice, or other opening defined in surface or adjacent to surface, or interior or exterior surface portions. Coating may comprise an ultra-thin transparent layer, enabling coating to be formed on surface with little to no impact on functionality or aesthetics of article.
  • Suitable substrate materials that may be treated include, for example, synthetic polymers, such as acrylics, nylons, polyesters, KevlarTM, NomexTM, polyolefins (polyethylenes, polypropylene, and other polyolefins), polycarbonates, polystyrenes, and copolymers of these with each other and with other monomers. Also included are blends of any of these materials in the same substrate, or composites of these materials with fibers or other materials, such as carbon fiber composites. Also contemplated are natural materials such as vegetable fibers or materials (e.g, cellulosic, ligninous, cotton, hemp), animal fibers or materials (e.g.
  • Suitable materials also include wood, paper, plaster, glass, silicon, composite materials, silicon-based materials, semiconducting materials, and insulating materials.
  • the surfaces may be coated directly upon a substrate material, or upon another suitable coating or film that is applied over the substrate (such as transparent plastic films for windshields or opaque films for waterproof surfaces).
  • the materials can be in any suitable form, such as fiber, yarn, bulk cloth, film, sheet, or bulk form. The coating can be applied in a batch or continuous process.
  • the substrate is plasma treated to remove organic contamination and increase the number density of reactive sites on the surface.
  • the plasma treatment may be either an air plasma, oxygen plasma, or a carbon dioxide plasma or equivalent.
  • the carbon dioxide plasma is intended to increase the number density of carboxyl, -COOH, groups on the surface.
  • the highest number density of -COOH groups is achieved by adjusting different variables such as plasma power which can be anywhere between 1 W-5000W, plasma treatment time, plasma treatment temperature which can be from -100°C-600°C and plasma gas pressure.
  • plasma power which can be anywhere between 1 W-5000W
  • plasma treatment time which can be from -100°C-600°C
  • plasma gas pressure a gas which can be from -100°C-600°C
  • Other materials that might add carboxyl groups to a surface during plasma treatment include carbon monoxide (CO), formic acid, acetic acid, trifluoroacetic acid, oxalic acid, oxalyl chloride, etc.
  • Oxygen and/or air plasmas may also introduce reactive functional
  • the substrate may comprise any material or combination of materials suitable for deposition of a silane compound.
  • materials suitable for forming substrate include the materials listed above.
  • a suitable substrate includes materials that can react with the plasma to form binding groups, such as carboxyl groups, on the surface.
  • carboxyl groups without being bound to any theory, it is believed that superior properties derive from a high- or higher-density of carboxyl groups, or even carbonyl groups, covalently bound to the surface of the substrate.
  • These carboxyl, or carbonyl groups may form covalent linkages with amine groups in the first silane, or may simply interact via acid-base interactions. This occurs from the acid/base interaction of carboxyl groups and amine groups, which forms a covalent bond upon thermally-induced dehydration.
  • These covalent linkages firmly attach the first silane to the surface, which in turn presents a robust, and adherent coating and presents a dense surface of reactive groups for attachment of the second silane.
  • Carbonyl groups may also react with amine groups, especially when either the carbonyl or amine group is on an aryl moiety.
  • the second silane to be chosen is to apply a
  • FIG. 1 illustrates an exemplary article 20 comprising a substrate 22 and a coating 26.
  • Substrate 22 may comprise a surface 24.
  • Coating 26 may comprise an adhesion promoting layer 28 and a hydrophobic layer 30.
  • Article 20 may comprise any suitable article or device having a surface portion.
  • article 20 may include, without limitation, any of those listed above, and also include electronic devices, silicon wafers, silicon chips, ink jet cartridges, plastic films, batteries, battery contacts, rechargeable batteries, mesh coverings, ear pieces, and components of the foregoing.
  • Article 20 may also comprise surfaces formed in any shape, size, texture, or configuration, including, for example, planar surfaces, curved surfaces, rough surfaces, smooth surfaces, and/or irregular surfaces.
  • article 20 may include various hearing aid devices, components, and/or accessories, including, for example, shell components, covers, in-the-ear domes (e.g., for open ear products), microphone covers (e.g., fabric mesh covers), volume controllers, switches, buttons, microphone ports, receiver ports, tubing, ear hooks, acoustic damping elements, battery doors, batteries, battery contacts, nozzles, DAI connectors, moisture and/or wax guards, face plate elements, ear molds (e.g., for standard ear molds and custom ear molds), and any other hearing aid device or component.
  • FIG. 2 illustrates a textile article 83, comprising fibers 81 , and yarns 82. To impart a hydrophobic surface to this article, the article, whether woven, knit, or non-woven, may be treated, or either the fibers or the yarns may be treated before manufacture of the woven, knit, or non- woven article.
  • FIG. 3 shows an exemplary portable electronic device (cell phone).
  • Hydrophobic surfaces may be applied to, for example, to casing 1 , front case 1 1 , rear case 12 , display screen 13, or keys 14, 15. Coatings may be selectively applied near the joints between 1 1 and 12, near holes and openings in the case, such as near openings for keys 14, 15.
  • Other portable electronic devices such as, PDAs, music players, media recorders and players, portable computers, and the like.
  • the plasma treated substrate can be hydrated with water vapor to further increase the bonding with the First Silane.
  • the substrate may also be hydrated with water vapor prior to deposition of the first silane.
  • the surface of the plasma-cleaned substrate is exposed to an amino silane, which is a silane with at least one amine group.
  • the first or amino silane acts as an adhesion promoter for second silane.
  • This silane could be any silane having an amine group.
  • This amine group could be on an alkyl or aryl moiety.
  • the substrate surface is exposed to the amino silane by any suitable system, such as vapor deposition systems.
  • the first silane has at least one silane group.
  • the silane group on the first silane may be represented by formula (I):
  • R 1 , R 2 , and R 3 may each be, independently, F, CI, Br, I, H, OH, a methoxy group, an ethoxy group, an isopropoxy group, an alkoxy group, an acetoxy group, a methyl group, an alkyl group, an aryl group, a perfluoroalkyl group, a partially fluorinated alkyl group, a dimethylamino group, a dialkylamino group, an ethylamino group, a monoalkylamino group, an amino group, a phenyl group, or a methoxyethoxyethoxy group.
  • the other group on the silane which is not R 1 , R 2 , or R 3 , and is directed to the left of the silicon, could be any chemical moiety that gives desired amino functionality to the silane molecule.
  • first silane may be represented by formula (II):
  • n may be an integer from 0- 32. In additional embodiments, n may be an integer from 1 -18. In at least one embodiment, n may be an integer from 3-4. Additionally, in formula (II), R 1 , R 2 , and R 3 may be as defined above for formula (I).
  • the first silane may also be represented as
  • L is any suitable group to attach the amine(s) and the silane(s).
  • L may be branched or straight, alkyl or aryl, and p and m may independently be 1 or greater than 1 .
  • R , R 2 , and R 3 may be as defined above for formula (I).
  • a suitable first silane is any compound that has amine groups that may interact with any surface carboxyl or carbonyl groups or other amine- reactive groups, and will interact favorably with the second silane.
  • the L group may be any suitable group that does not interact or interfere with the attachment to the substrate or the second silane, or materially affect the properties of the surface, such as through chemical reactions, stereo interference, or the like.
  • Suitable L groups one or a combination of straight or branched carbon chains, optionally containing all kinds of possible atoms.
  • Examples of the first silane include, but are not limited to 4- aminobutyltriethoxysilane, 1 -amino-2-(dimethylethoxysilyl)propane, n- (2-aminoethyl)-3 -aminoisobutyldimethylmethoxysilane, n-(2-aminoctyl)-
  • the surface treated with the first silane is exposed to water vapors to hydrolyze -Si(OR) 3 groups, or other hydrolyzable groups such as Si-CI, of the attached amino silane to -Si(OH) 3 groups, which makes the surface more reactive towards the second silane.
  • the hydrolysis may be by any suitable system, such as exposing the surface to moisture.
  • the surface is treated with a second silane to impart a surface with desired properties.
  • the second silane may be any second silane as disclosed in United States Patent
  • a second silane is deposited upon and bonded to the adhesion
  • the second silane is often chosen to provide an outer layer with a hydrophobic surface.
  • the second silane may also be chosen to provide other properties to the surface, such an oleophobic surface or a hydrophobic/oleophobic surface, or even a hydrophilic surface.
  • the hydrophobic layer may comprise a second silane having at least one perfluorinated aliphatic group.
  • hydrophobic layer may also comprise additional compounds in addition to the second silane.
  • the additional compounds in hydrophobic layer may impart various desirable properties to hydrophobic layer, such as, for example, microbial resistance, without preventing the hydrophobicity of the hydrophobic layer and/or the second silane from acting as a hydrophobic and/or oleophobic layer or compound.
  • the second silane may comprise long alkyl chains, partially fluorinated alkyl chains, and/or alkyl chains that have regions that are perfluorinated, any of which may be straight or branched.
  • the second silane may contain aryl groups.
  • the second silane may comprise alkyl chains having the general formulas CF 3 (CF2)n(CH 2 )mSiR R 2 R 3 and/or
  • the second silane and/or the hydrophobic layer may comprise mixtures of alkyl, perfluoroalkyl, or partially fluorinated alkyl chains.
  • the second silane may be capable of bonding to the first silane through, for example, a siloxane (Si-O-Si) linkage. Additionally, the second silane may be capable of forming polymers containing siloxane linkages.
  • the silane group on the second silane may be represented by formula (III):
  • R 4 , R 5 , and R 6 may each be, independently, F, CI, Br, I, H, OH, a methoxy group, an ethoxy group, an isopropoxy group, an alkoxy group, an acetoxy group, a methyl group, an alkyl group, a perfluoroalkyl group, a partially fluorinated alkyl group, a dimethylamino group, a dialkylamino group, an ethylamino group, a monoalkylamino group, an amino group, a phenyl group, or a methoxyethoxyethoxy group.
  • the second silane may be represented by formula (IV):
  • n may be an integer from 0-32, and R 4 , R 5 , and R 6 may be as defined above for formula (III). In additional embodiments, n may be integer from 1 -16. In at least one embodiment, n may be an integer from 5-9.
  • the second silane include, without limitation, (tridecafluoro-1 ,1 ,2,2-tetrahydrooctyl)trichlorosilane, (tridecafluoro- 1 ,1 ,2,2-tetrahydrooctyl)methyldichlorosilane, (tridecafluoro-1 ,1 ,2,2- tetrahydrooctyl)trimethoxysilane, (tridecafluoro-1 ,1 ,2,2- tetrahydrooctyl)triethoxysilane, (tris(tridecafluoro 1 ,1 ,2,2- tetrahydrooctyl)dimethylsiloxy)chlorosilane, (heptadecafluoro-1 ,1 ,2,2- tetrahydrodecyl)trichlorosilane, triethoxy(1 H,1 H,2H,2H- perfluorooclane,
  • the second silane may also include compounds according to the general formula
  • hydrophobic layer may comprise a germanium compound (e.g., a germane) in addition to or in place of a silane compound.
  • Germanium compounds may function as adhesion promoting and hydrophobic compositions in a manner similar to analogous silicon compounds.
  • silicon compounds listed above as examples of the first silane or the second silane may be substituted with analogous
  • germanium compounds in which the Si atom is replaced with a Ge atom.
  • a mixture of silanes could be employed in the second silane deposition.
  • a silane with a perfluorinated tail and a silane containing an alkyl chain could be jointly deposited in this manner.
  • the abrasion resistance of the coating can be further improved by using a cross-linker.
  • This cross-linker can be used in the following ways:
  • the mixtures of the amino silane and cross-linker, and second silane and cross-linker may have any percentage of cross-linker in them.
  • the use of this reagent will cross-link deposited aminosilane and/or second silane coatings, which will make them even more robust and hence more abrasion resistant.
  • cross-linkers can be used for this purpose, e.g., diisocyantes, which have a general formula OCN-R-NCO, diacidchlorides, which have a general formula CIOC-R-COCI, diesters, e.g., dimethyl and diethyl esters, which have a general formula CH3COO-R-COOCH3 or C 2 H 5 COO-R-COOC 2 H 5 , where R is a carbon chain containing all kinds of possible atoms in it.
  • Silanes can also be used as a cross-linker.
  • silanes have a general formula (RO) 3 -Si- L-Si(OR) 3 , (RO) 2 CH 3 -Si-L-Si-CH 3 (OR) 2 or RO(CH 3 ) 2 -Si-L-Si-(CH 3 ) 2 -OR ! where R may be C 2 H 5 , CH 3 and L may be a carbon chain, such as an alkyl or aryl group, containing all kinds of possible atoms in it.
  • alkoxy groups -OR
  • Other examples of possible cross-linkers are glycidoxypropyltrimethoxysilane and glutaraldehyde.
  • FIG. 1 is a schematic cross-section of the coated article.
  • FIG. 2 a schematic view of a coated article.
  • FIG. 3 a schematic view of a coated article.
  • FIG. 4 is a chart showing wetting test parameters for determining water repellancy.
  • FIG. 5 is a chart use for determining standard spray test ratings.
  • FIG. 6 is a graph showing wetting test data.
  • the plasma cleaning/treatment of the substrate was performed in a CO 2 or oxygen plasma.
  • a total of four plates (two active plates and two ground plates) were employed, and the voltage was applied to the active plates for plasma generation. These plates were arranged in the order: active, ground, ground and active (AGGA) from top to bottom.
  • the fabric was placed on the third plate from the top (the lower ground plate). The fabric was plasma treated at 100W for 2.5 minutes.
  • Amino silane functionalized fabric was then exposed to water vapors by injecting 1 mL of water into the chamber. This hydrolysis was for 20 minutes. This treatment is believed to hydrolyze -Si(OR) 3 groups of the amino silane to -Si(OH) 3 groups, and hence make the surface more reactive towards the attachment of second silane. After the reaction, unreacted water was pumped out of the chamber.
  • silane/adhesion promoter that is not amine terminated.
  • a comparative test was conducted which involves the use of 3- isocyanatopropyl triethoxysilane as the first silane or adhesion promoter in the treatment of a nylon surface.
  • the process used an air plasma to oxidize the surface.
  • the second silane, (tridecafluoro-1 ,1 ,2,2- tetrahydrooctyl)trimethoxysilane was bonded to the first silane in an attempt to make the surface hydrophobic. However it was found the surface did not become hydrophobic after the deposition.
  • chemical vapor deposition was performed on nylon without using the isocyanato silane adhesion promoter, where the remaining process was the same. The surface did not become
  • APTES triethoxysilane
  • a nylon swatch having a hydrophobic coating was made by the same chemical vapor deposition (CVD) process as in Example 2, but using an oxygen plasma.
  • the first and second silanes were APTMS, and
  • Example 3 The process of Example 3 was repeated, but the oxygen plasma was replaced with carbon dioxide plasma.
  • the hydrophobic coating lasted at least 1700 cycles in the abrasion test. From this it can be concluded that use of a carbon dioxide plasma helped significantly improve the abrasion resistance of the coating as noted above in similar samples.
  • An Apple iPod was also coated using the process of Example 4. CVD was done at 60 °C. The process used a C0 2 plasma, APTMS was the adhesion promoter. Treatment by the plasma and application of the APTMS, was followed by hydrolysis and application of (tridecafluoro- 1 ,1 ,2,2-tetrahydrooctyl)trimethoxysilane. To test hydrophobicity, water contact angles were measured. Water contact angles may be used as a measure of surface hydrophobicity. A higher water contact angle for a surface may indicate that the surface has a higher degree of
  • a comparative set of tests were conducted, comparing carbon dioxide plasma with oxygen plasma treatment, and comparing 3- aminopropyltrimethoxysilane (APTMS) and 3- isocyanatopropyltriethoxysilane (ICPTES) for the first silane.
  • Samples were produced by treating pieces of polyester fabric as a substrate essentially as described above. All tests were done with 20 minute depositions of each silane, and a 20 minute hydrolysis step. The temperature of the reaction was 100°C.
  • AATCC Test Method 22-2005, Water Repellency: Spray Test The spray 5 patterns were evaluated by comparison to a rating chart, which is shown in FIG. 5, and with reference to Table 2. The results are shown in Table 1 .
  • FIG. 6 is a graphical representation of data the wetting test data contained in Table 3 above.

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Abstract

La présente invention concerne un revêtement hydrophobe et un procédé de préparation de revêtement hydrophobe avec une couche promotrice d'adhésion formée à partir d'une composition promotrice d'adhésion et une couche hydrophobe. La composition promotrice d'adhésion peut comprendre un composé promoteur d'adhésion ayant un groupe amine et au moins un groupe fonctionnel silane et/ou un groupe fonctionnel germanium. La composition formant une couche hydrophobe peut comprendre un composé formant une couche hydrophobe ayant un groupe aliphatique hydrophobe et au moins un groupe fonctionnel silane et/ou un groupe fonctionnel germanium.
PCT/US2010/042297 2010-07-16 2010-07-16 Revêtement hydrophobe et procédé Ceased WO2012008970A1 (fr)

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US10472769B2 (en) 2013-10-10 2019-11-12 The Regents Of The University Of Michigan Silane based surfaces with extreme wettabilities
US10590350B2 (en) 2013-10-09 2020-03-17 The Regents Of The University Of Michigan Apparatuses and methods for energy efficient separations including refining of fuel products
CN113556996A (zh) * 2020-02-20 2021-10-26 金智娟 水解性环保型卫生巾

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DE102013220575A9 (de) 2013-03-14 2014-12-18 Honda Motor Co., Ltd. Verbundkörper, hergestellt aus verschiedenen Materialien und Verfahren zu dessen Herstellung
US10590350B2 (en) 2013-10-09 2020-03-17 The Regents Of The University Of Michigan Apparatuses and methods for energy efficient separations including refining of fuel products
US10472769B2 (en) 2013-10-10 2019-11-12 The Regents Of The University Of Michigan Silane based surfaces with extreme wettabilities
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CN113556996B (zh) * 2020-02-20 2023-01-10 金智娟 水解性环保型卫生巾

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