WO2009156579A1 - Coating composition and process for preparing it - Google Patents
Coating composition and process for preparing it Download PDFInfo
- Publication number
- WO2009156579A1 WO2009156579A1 PCT/FI2009/050528 FI2009050528W WO2009156579A1 WO 2009156579 A1 WO2009156579 A1 WO 2009156579A1 FI 2009050528 W FI2009050528 W FI 2009050528W WO 2009156579 A1 WO2009156579 A1 WO 2009156579A1
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- WIPO (PCT)
- Prior art keywords
- coating composition
- composition according
- weight
- salt
- coating
- Prior art date
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- 239000008199 coating composition Substances 0.000 title claims abstract description 55
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000000758 substrate Substances 0.000 claims abstract description 17
- 239000000126 substance Substances 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 230000003670 easy-to-clean Effects 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims description 65
- 239000011521 glass Substances 0.000 claims description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 14
- 239000000375 suspending agent Substances 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- -1 silane compound Chemical class 0.000 claims description 11
- 229910000077 silane Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000000919 ceramic Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 239000012266 salt solution Substances 0.000 claims description 6
- 239000004567 concrete Substances 0.000 claims description 4
- 239000011435 rock Substances 0.000 claims description 4
- 229920001971 elastomer Polymers 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 239000005060 rubber Substances 0.000 claims description 3
- 229920001169 thermoplastic Polymers 0.000 claims description 3
- 229920001187 thermosetting polymer Polymers 0.000 claims description 3
- 239000004416 thermosoftening plastic Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 125000003158 alcohol group Chemical group 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 239000005871 repellent Substances 0.000 abstract description 5
- 238000000576 coating method Methods 0.000 description 19
- 239000011248 coating agent Substances 0.000 description 18
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000523 sample Substances 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 230000004913 activation Effects 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 239000004033 plastic Substances 0.000 description 7
- 229920003023 plastic Polymers 0.000 description 7
- 229920001296 polysiloxane Polymers 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000001680 brushing effect Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 230000005923 long-lasting effect Effects 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000005357 flat glass Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000005661 hydrophobic surface Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920005606 polypropylene copolymer Polymers 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 239000013074 reference sample Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 230000001846 repelling effect Effects 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- BPCXHCSZMTWUBW-UHFFFAOYSA-N triethoxy(1,1,2,2,3,3,4,4,5,5,8,8,8-tridecafluorooctyl)silane Chemical compound CCO[Si](OCC)(OCC)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCC(F)(F)F BPCXHCSZMTWUBW-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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
- C03C17/28—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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/02—Polysilicates
-
- 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
- C04B41/46—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements with organic materials
- C04B41/49—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes
- C04B41/4905—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes containing silicon
- C04B41/4922—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes containing silicon applied to the substrate as monomers, i.e. as organosilanes RnSiX4-n, e.g. alkyltrialkoxysilane, dialkyldialkoxysilane
- C04B41/4933—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes containing silicon applied to the substrate as monomers, i.e. as organosilanes RnSiX4-n, e.g. alkyltrialkoxysilane, dialkyldialkoxysilane containing halogens, i.e. organohalogen silanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
Definitions
- the invention relates to a coating composition, a process for preparing it, and its use.
- the invention relates to a coating composition having hydrophobic, oleophobic and dirt-repellent properties, to a process for preparing it, and to its use.
- compositions providing an easy-to-c!ean surface for various material surfaces have been widely described in literature in the field.
- US patent publication 2006/0185555 A1 discloses a two-component coating system which, when applied to smooth surfaces, gives an easy-to- ciean surface.
- the first component of the system comprises fluoroalkylsiiane, aikyisilane or a mixture thereof, and the second component comprises water, an organic or inorganic acid and a solvent.
- Each component is prepared separately, combined with each other and mixed for 2 minutes, after which the mixture is ready to be used.
- the system is applicable to windscreens, glass- walled shower cubicles, glass facades, wall tiles and sanitary ceramics.
- WO publication 2007/068545 A2 relates to a storage-stable coating composition which is abrasion and weather resistant and which gives, when applied to smooth surfaces, an easy-to-clean surface.
- the composition comprises hydrolyzable fluoroalkylsiiane, hydrochloric acid as catalyst of hydrolysis and condensation, water, isopropanol and solvent.
- the composition is applicable to metal, glass, ceramic substances and glazed surfaces, such as windscreens, glass-walled shower cubicles, glass facades, wall tiles and sanitary ceramics.
- US patent publication 2004/0005469 A1 describes a process for preparing a product with a long-lasting, easy-to-clean surface.
- the surface is coated with a coating mixture comprising a gel-forming metal oxide, such as SiO 2 , and hydrophobic agent evenly distributed in a metal oxide network structure. Silicones, silanes, siloxanes, silicone oils and silicone greases are suitable to be used as the hydrophobic agent.
- the coating mixture is prepared by dissolving the hydrophobic agent in a solvent and by adding concentrated hydrochloric acid and water to this mixture.
- a metal oxide gel coating is prepared for the surface of the product with a sol-ge! method, the gel being formed on the surface in situ during the application of the coating mixture.
- the coating mixture is applicable to metals, plastics, inorganic substances, rocks and particularly glass and glass porcelain.
- silicone-based compositions which can be prepared to have a neutral pH without using an acid may also be used as dirt repellents.
- a problem with surfaces treated with silicone is that they are difficult to after-treat, which is due to the known surface-tension-reducing effect of the silicones. It has turned out that it is virtually impossible for paint, for example, to adhere to a silicone-based surface due to the extensive water and oi! repelling property of the surface.
- compositions containing silane contain strong acid which is required for activating silane in order to achieve the desired properties for the coating when the composition is applied to the surface of a substrate. Owing to the presence of the strong acid, the composition is strongly acidic, due to which treatment of the composition requires particular care. On the other hand, due to their acidic nature, the compositions are not applicable to all surfaces because they are corrosive. Problems arise particularly with metals, such as aluminium, and plastics, in which case the strongly acidic composition reacts with different functional groups of plastics.
- An object of the invention is thus to provide a coating composition with high wear and scratch resistance when applied to a surface and giving, at the same time, an easy-to-clean and dirt-repellent surface to the end product.
- a further object of the invention is to provide a coating composition which the end user finds easy to handle and which is applicable to being applied to all types of surfaces.
- the object of the invention is achieved with a coating composition which is characterized by what is stated in the independent claims. Preferred embodiments of the invention are disclosed in the dependent claims.
- the invention is based on the idea that the fluorosilane compound in the coating composition is activated without an acid by means of a sait solution.
- An advantage of the coating composition according to the invention is that the composition to be applied has a neutral pH, i.e. approximately 6 to 7, which means that it is easy to handle. Further, a neutral composition without corrosive properties is applicable to all types of surfaces, such as glass, ceramic substances, rocks, concrete, metals, rubber, thermoplastics and thermosetting plastics, such as polycarbonates, ABS plastics, polypropylene, copolymers of propylene and ethylene, polyurethane and epoxies as well as to painted surfaces.
- the coating composition is also storage-stable and provides a durable coating when applied to a product.
- a smooth durable coating with homogeneous properties through the whole cross direction of the coating is provided by applying to the surface of the product a composition containing an agent with easy-to-clean properties.
- the invention relates to a coating composition comprising one or more fluoroalkylsilane compounds, volatile substance, salt and water.
- one or more fluoroalkylsilane compounds is/are used as an agent with dirt-repellent properties.
- fluoroalkylsilane compounds are available as commercial products, for example under trademark DYNASYLAN ® F 8261 (tridecafluorooctyltriethoxysilane) from the company Degussa AG.
- Usable fluoroalkylsilanes have the general formula
- the amount of fluoroaSkyisilane compound in the composition is 0.1 to 10% by weight, preferably 2 to 3% by weight, more preferably 0.5 to 1.5% by weight, based on the total composition.
- a solvent or a diluter is used as the volatile substance.
- these include alcohols, for example methanol, ethanol, isopropanol, n-butanol and white spirit, esters, such as ethyl acetate, ethers, glycols and glycol ethers. Mixtures of said substances may also be used.
- isopropanol is used.
- the amount of volatile substance in the composition is 50 to 80% by weight, preferably 70 to 80% by weight,
- the fluoroaikyisilane compound is activated by means of salt, water, alcohol and the oxygen present.
- methanol, ethanol, isopropanol, n-butanol or white spirit may be used as the alcohol.
- Oxygen of air appropriately serves as the oxygen source.
- Activation of the fluoroaikyisilane compound refers, in this invention, to hydrolysis of the silane compound, which means that the compound decomposes into a colloidal suspension, i.e. a sol, in the liquid, and the compound is brought to an active state in order for it to be capable of forming a durable network structure while it is gelled on the surface of the substrate.
- the activation is appropriately carried out in a tank.
- the amount of oxygen present in the tank is approximately 10 to 40% by volume, preferably approximately 40% by volume, based on the total volume of the composition.
- the activation stage takes about 38 to 72 hours, after which the composition is ready to be used.
- Inorganic salt in particular, is used as salt in the coating composition according to the invention.
- Particularly appropriate salts include halides of alkali metals and alkali earth metals, particularly chlorides.
- NaCI is used as salt.
- the amount of salt in the composition is 0.25 to 0.75% by weight.
- the amount of water in the composition is 5 to 45% by weight, preferably about 20% by weight,
- suspending agent may be added to the ready-for- use, activated coating composition, whereby the rate of gelling on the surface of the substrate can be controlled in a desired manner by selecting an appropriate suspending agent on the basis of the evaporation rate.
- the desired evaporation rate may vary depending on which substrate the coating composition is applied to. In coating metals, for example, it may be desirable that the gelling take place slowly.
- Alcohols for example ethanol, isopropanol, n-butano! and white spirit
- ketones for example acetone, for example ethyl acetate, ethers and hydrocarbons, for example xylene, may be used as the suspending agent.
- n-butanol as the suspending agent.
- a suitable suspending agent for polyurethane and polyester plastics is xylene.
- Acetone is also suitable for polyesters.
- Ethyl acetate and ketones are suitable for acryl-based plastics.
- the pH of the coating composition according to the invention is in the neutral range, i.e. approximately 6 to 7.
- the invention also relates to a process for preparing a coating composition of the above-described type, the process comprising
- the coating composition according to the invention is applied to the surface of the substrate by means of what is called a sol-gel method.
- a sol-gel method In the activation of the fluoroalkylsilane compound in the volatile substance in accordance with the invention, polycondensation of the compound takes place, whereby long silane chains are formed and a colloidal suspension, i.e. a sol, is provided.
- the obtained sol is then applied to the substrate, whereby, along with the evaporation of the volatile substance, the surface of the substrate is provided in situ with a gel network structure in which the silane compound is evenly distributed in the cross direction of the whole gei structure.
- the rate of the gel formation may be controlled, if desired, by means of the suspending agent present.
- the coating composition according to the invention provides a durable gel coating for the substrate at the room temperature within 35 to 45 minutes from the application.
- several factors affect the gel ⁇ ng time, such as the surrounding humidity, and great humidity may slow down the gelling.
- Gel formation on the surface of the substrate may be accelerated, if desired, with heat treatment. Heat treatment may be performed at a temperature of 45 to 80 0 C for 15 minutes, for example.
- hexadecyi trimethoxysilane may be added to the composition in an amount of 1 to 5% by weight on weight basis of the composition, in which case the end product is provided not only with easy-to-clean properties but also a particularly good moisture barrier.
- a coating composition is applicable to metals, plastics and concrete as wel! as to other porous surfaces.
- the coating composition according to the invention may be applied to the substrate with any known technique, such as by spraying, with a roll, by wiping with a cloth, by embedding, brushing or draw coating.
- the thickness of the network-structured coating composition on the surface of the end product is approximately 1 to 5 nm.
- the invention also relates to the use of a composition according to the invention or a composition prepared with a process according to the invention on the surface of the substrate, wherein a durable, easy-to- ciean surface is provided.
- Glass, ceramics, rock, concrete, metal, rubber or many thermoplastics or thermosetting plastics, such as PU, PVC, PE and PP, may be used as the substrate.
- Formulation 1 12.5 g of NaCl salt is mixed into 1 000 g of uitrapurified water manually or with a mechanical stirrer until the salt is completely dissolved in the water, and the mixture is dear.
- Formulation 2 1.0 g of fiuoroalkylsilane (DYNASYLAN ® F 8261 from the company Degussa AG) is mixed into 100 g of isopropanol manually or with mechanical stirrer until the a clear solution is obtained. [0032] 20 g of formulation 1 and the obtained formulation 2 (101 g) are mixed with each other for about 10 minutes. The obtained mixture is stored in a tank for activation of the silane in such a way that 30 to 40% by volume of air space remains in the tank, based on the amount of solution. The silane is allowed to be activated for 72 hours. The excess salt is filtered off from the solution, after which the solution is ready to be used.
- DYNASYLAN ® F 8261 from the company Degussa AG
- An example illustrates the durability of the coating composition according to the invention on the surface of a window glass.
- the coating composition was applied with a cloth and allowed to be gelled on the surface of the glass for 24 hours, after which the wash resistance of the coating was determined by means of a brush according to the standard SFS 3755, when applicable.
- the pieces to be tested were brushed 5 000 times. After each 1 000 times, a contact angle was measured from the pieces, and the durability of the coatings was assessed by means of it.
- the test conditions were as follows:
- sample A represents the coating composition according to the invention, prepared in the manner described in Example 1.
- Sample B is a reference composition in which formulation 2 was prepared in the same way as in Example 1 but formulation 1 was prepared by adding 0.5 g of 33.3-% hydrochlorid acid to 10 g of ultrapurified water. Formulations 1 and 2 were combined, after which the obtained composition was allowed to be activated for 10 hours.
- sample C is a reference composition, i.e. the silicone-based acid-activated product DYNASYLAN ® F 8263 from the company Degussa AG.
- sample A the contact angle of the coating composition according to the invention (sample A) was smaller than the contact angle of reference sample B before the test was started, the surface energy in sample A was, surprisingly, lower than in B from the start, which is shown by formation of large drops on the glass surface.
- the coating composition according to the invention when used, self- cleaning of the glass is more efficient than with reference compositions.
- This effect has a practical significance for instance when using the coating in the windscreen of a car, in which case drizzle or washing water does not remain as small drops on the surface of the glass, which would deteriorate visibility, but it is gathered as larger drops on the surface. Deteriorated visibility is particularly harmful when one is driving in the dark, in which case the reflection of externa! lights from small drops may be significant.
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Abstract
The invention relates to an acid-free coating composition comprising one or more fluoroalkylsilane compounds, volatile substance, salt and water, a process for preparing it and its use. Applied to a substrate, the coating composition provides an easy-to-clean and dirt-repellent surface.
Description
COATING COMPOSITION AND PROCESS FOR PREPARING IT
BACKGROUND OF THE INVENTION
[0001] The invention relates to a coating composition, a process for preparing it, and its use. Particularly, the invention relates to a coating composition having hydrophobic, oleophobic and dirt-repellent properties, to a process for preparing it, and to its use.
[0002] Compositions providing an easy-to-c!ean surface for various material surfaces have been widely described in literature in the field. US patent publication 2006/0185555 A1 , for example, discloses a two-component coating system which, when applied to smooth surfaces, gives an easy-to- ciean surface. The first component of the system comprises fluoroalkylsiiane, aikyisilane or a mixture thereof, and the second component comprises water, an organic or inorganic acid and a solvent. Each component is prepared separately, combined with each other and mixed for 2 minutes, after which the mixture is ready to be used. The system is applicable to windscreens, glass- walled shower cubicles, glass facades, wall tiles and sanitary ceramics.
[0003] WO publication 2007/068545 A2 relates to a storage-stable coating composition which is abrasion and weather resistant and which gives, when applied to smooth surfaces, an easy-to-clean surface. The composition comprises hydrolyzable fluoroalkylsiiane, hydrochloric acid as catalyst of hydrolysis and condensation, water, isopropanol and solvent. The composition is applicable to metal, glass, ceramic substances and glazed surfaces, such as windscreens, glass-walled shower cubicles, glass facades, wall tiles and sanitary ceramics.
[0004] US patent publication 2004/0005469 A1 describes a process for preparing a product with a long-lasting, easy-to-clean surface. The surface is coated with a coating mixture comprising a gel-forming metal oxide, such as SiO2, and hydrophobic agent evenly distributed in a metal oxide network structure. Silicones, silanes, siloxanes, silicone oils and silicone greases are suitable to be used as the hydrophobic agent. The coating mixture is prepared by dissolving the hydrophobic agent in a solvent and by adding concentrated hydrochloric acid and water to this mixture. A metal oxide gel coating is prepared for the surface of the product with a sol-ge! method, the gel being formed on the surface in situ during the application of the coating mixture. The coating mixture is applicable to metals, plastics, inorganic substances, rocks
and particularly glass and glass porcelain.
[0005] As known, silicone-based compositions which can be prepared to have a neutral pH without using an acid may also be used as dirt repellents. A problem with surfaces treated with silicone is that they are difficult to after-treat, which is due to the known surface-tension-reducing effect of the silicones. It has turned out that it is virtually impossible for paint, for example, to adhere to a silicone-based surface due to the extensive water and oi! repelling property of the surface.
[0006] A problem with the above-described compositions containing silane is that the compositions contain strong acid which is required for activating silane in order to achieve the desired properties for the coating when the composition is applied to the surface of a substrate. Owing to the presence of the strong acid, the composition is strongly acidic, due to which treatment of the composition requires particular care. On the other hand, due to their acidic nature, the compositions are not applicable to all surfaces because they are corrosive. Problems arise particularly with metals, such as aluminium, and plastics, in which case the strongly acidic composition reacts with different functional groups of plastics.
[0007] Further, a problem with compositions already on the market is their restricted preservability and insufficient durability on the surface of a product, it can be assumed that a silane activated with an acid is not capable of forming sufficiently long silane chains to form a gel-like network structure, which would guarantee a good abrasive resistant surface for the end product, but partial decomposition of silane also takes place in the acid activation. This results in a short silane chain and there will be no durable network structure formed by long silane chains.
BRIEF DESCRIPTION OF THE INVENTION
[0008] An object of the invention is thus to provide a coating composition with high wear and scratch resistance when applied to a surface and giving, at the same time, an easy-to-clean and dirt-repellent surface to the end product. A further object of the invention is to provide a coating composition which the end user finds easy to handle and which is applicable to being applied to all types of surfaces. The object of the invention is achieved with a coating composition which is characterized by what is stated in the
independent claims. Preferred embodiments of the invention are disclosed in the dependent claims.
[0009] The invention is based on the idea that the fluorosilane compound in the coating composition is activated without an acid by means of a sait solution.
[0010] An advantage of the coating composition according to the invention is that the composition to be applied has a neutral pH, i.e. approximately 6 to 7, which means that it is easy to handle. Further, a neutral composition without corrosive properties is applicable to all types of surfaces, such as glass, ceramic substances, rocks, concrete, metals, rubber, thermoplastics and thermosetting plastics, such as polycarbonates, ABS plastics, polypropylene, copolymers of propylene and ethylene, polyurethane and epoxies as well as to painted surfaces.
[0011] The coating composition is also storage-stable and provides a durable coating when applied to a product.
DETAILED DESCRIPTION OF THE INVENTION
[0012] in accordance with the present invention, a smooth durable coating with homogeneous properties through the whole cross direction of the coating is provided by applying to the surface of the product a composition containing an agent with easy-to-clean properties. Thus, in accordance with one aspect, the invention relates to a coating composition comprising one or more fluoroalkylsilane compounds, volatile substance, salt and water.
[0013] In this invention, one or more fluoroalkylsilane compounds is/are used as an agent with dirt-repellent properties. These are available as commercial products, for example under trademark DYNASYLAN® F 8261 (tridecafluorooctyltriethoxysilane) from the company Degussa AG. Usable fluoroalkylsilanes have the general formula
F3C(CF2)m(CH2)nSiR yX(3-y)
where X is chlorine or RO, and R is a linear or branched alkyl group with 1 to 4 carbon atoms, R1 is a linear or branched or cyclic alkyl group with 1 to 8 carbon atoms, n is 0 or 2, y is 0, 1 or 2, and m is 0 to 18.
[0014] The amount of fluoroaSkyisilane compound in the composition is 0.1 to 10% by weight, preferably 2 to 3% by weight, more preferably 0.5 to 1.5% by weight, based on the total composition.
[0015] In accordance with the invention, a solvent or a diluter is used as the volatile substance. These include alcohols, for example methanol, ethanol, isopropanol, n-butanol and white spirit, esters, such as ethyl acetate, ethers, glycols and glycol ethers. Mixtures of said substances may also be used. Preferably, isopropanol is used. The amount of volatile substance in the composition is 50 to 80% by weight, preferably 70 to 80% by weight,
[0016] In this invention, the fluoroaikyisilane compound is activated by means of salt, water, alcohol and the oxygen present. For instance methanol, ethanol, isopropanol, n-butanol or white spirit may be used as the alcohol. Oxygen of air appropriately serves as the oxygen source. Activation of the fluoroaikyisilane compound refers, in this invention, to hydrolysis of the silane compound, which means that the compound decomposes into a colloidal suspension, i.e. a sol, in the liquid, and the compound is brought to an active state in order for it to be capable of forming a durable network structure while it is gelled on the surface of the substrate. The activation is appropriately carried out in a tank. !t is essential in the activation that the amount of oxygen present in the tank is approximately 10 to 40% by volume, preferably approximately 40% by volume, based on the total volume of the composition. The activation stage takes about 38 to 72 hours, after which the composition is ready to be used.
[0017] Inorganic salt, in particular, is used as salt in the coating composition according to the invention. Particularly appropriate salts include halides of alkali metals and alkali earth metals, particularly chlorides. In an embodiment of the invention, NaCI is used as salt. The amount of salt in the composition is 0.25 to 0.75% by weight.
[0018] The amount of water in the composition is 5 to 45% by weight, preferably about 20% by weight,
[0019] Further, suspending agent may be added to the ready-for- use, activated coating composition, whereby the rate of gelling on the surface of the substrate can be controlled in a desired manner by selecting an appropriate suspending agent on the basis of the evaporation rate. The desired evaporation rate may vary depending on which substrate the coating composition is applied to. In coating metals, for example, it may be desirable
that the gelling take place slowly. Alcohols, for example ethanol, isopropanol, n-butano! and white spirit, ketones, for example acetone, for example ethyl acetate, ethers and hydrocarbons, for example xylene, may be used as the suspending agent. It can be mentioned, by way of example, that when the substrate is a metal or PVC plastic, it is appropriate to use n-butanol as the suspending agent. A suitable suspending agent for polyurethane and polyester plastics is xylene. Acetone is also suitable for polyesters. Ethyl acetate and ketones are suitable for acryl-based plastics.
[0020] 5 to 100% by weight of suspending agent is added to the coating composition activated in the above-described manner. The content of the suspending agent in the coating composition is thus approximately 4 to 50% by weight of the amount of the total composition.
[0021] The pH of the coating composition according to the invention is in the neutral range, i.e. approximately 6 to 7.
[0022] The invention also relates to a process for preparing a coating composition of the above-described type, the process comprising
- mixing the salt and the water to obtain a salt solution
- mixing the silane compound and the volatile substance to obtain a mixture
- mixing said salt solution and said mixture with each other to obtain a raw composition
- allowing the raw composition to stand for 38 to 72 hours, obtaining thus an activated coating composition
- adding, if desired, suspending agent to the activated coating composition.
[0023] In forming the salt solution of salt and water, it is important to take into account that the pH of the salt solution is neutral.
[0024] The coating composition according to the invention is applied to the surface of the substrate by means of what is called a sol-gel method. In the activation of the fluoroalkylsilane compound in the volatile substance in accordance with the invention, polycondensation of the compound takes place, whereby long silane chains are formed and a colloidal suspension, i.e. a sol, is provided. The obtained sol is then applied to the substrate, whereby, along with the evaporation of the volatile substance, the surface of the substrate is provided in situ with a gel network structure in which the silane compound is evenly distributed in the cross direction of the whole gei structure. As
presented above, the rate of the gel formation may be controlled, if desired, by means of the suspending agent present.
[0025] The coating composition according to the invention provides a durable gel coating for the substrate at the room temperature within 35 to 45 minutes from the application. However, several factors affect the gelϋng time, such as the surrounding humidity, and great humidity may slow down the gelling. Gel formation on the surface of the substrate may be accelerated, if desired, with heat treatment. Heat treatment may be performed at a temperature of 45 to 80 0C for 15 minutes, for example.
[0026] Other substances may be added to the coating composition according to the invention to provide desired properties. For example, hexadecyi trimethoxysilane may be added to the composition in an amount of 1 to 5% by weight on weight basis of the composition, in which case the end product is provided not only with easy-to-clean properties but also a particularly good moisture barrier. Such a coating composition is applicable to metals, plastics and concrete as wel! as to other porous surfaces.
[0027] The coating composition according to the invention may be applied to the substrate with any known technique, such as by spraying, with a roll, by wiping with a cloth, by embedding, brushing or draw coating. The thickness of the network-structured coating composition on the surface of the end product is approximately 1 to 5 nm.
[0028] The invention also relates to the use of a composition according to the invention or a composition prepared with a process according to the invention on the surface of the substrate, wherein a durable, easy-to- ciean surface is provided. Glass, ceramics, rock, concrete, metal, rubber or many thermoplastics or thermosetting plastics, such as PU, PVC, PE and PP, may be used as the substrate.
[0029] The following examples illustrate the invention.
EXAMPLE 1
[0030] Formulation 1. 12.5 g of NaCl salt is mixed into 1 000 g of uitrapurified water manually or with a mechanical stirrer until the salt is completely dissolved in the water, and the mixture is dear.
[0031] Formulation 2. 1.0 g of fiuoroalkylsilane (DYNASYLAN® F 8261 from the company Degussa AG) is mixed into 100 g of isopropanol manually or with mechanical stirrer until the a clear solution is obtained.
[0032] 20 g of formulation 1 and the obtained formulation 2 (101 g) are mixed with each other for about 10 minutes. The obtained mixture is stored in a tank for activation of the silane in such a way that 30 to 40% by volume of air space remains in the tank, based on the amount of solution. The silane is allowed to be activated for 72 hours. The excess salt is filtered off from the solution, after which the solution is ready to be used.
EXAMPLE 2
[0033] 40 g of n-butanol is added to 100 g of the activated product prepared in Example 1. A coating composition is obtained which gives an extremely long-lasting wear resistant coating to metais.
EXAMPLE 3
[0034] 5 g of xylene is added to 100 g of the activated product prepared in Example 1. The obtained composition is mixed into polyurethane- polyester-based paint. A highly moisture resistant and hydrophobic surface is obtained.
EXAMPLE 4
[0035] 5 g of acetone is added to 100 g of the activated product prepared in Example 1. The obtained composition gives polyester resins good moisture resistance and hydrophobicity.
EXAMPLE 5: DETERMINING WASH RESISTANCE OF COATING
[0036] An example illustrates the durability of the coating composition according to the invention on the surface of a window glass. The coating composition was applied with a cloth and allowed to be gelled on the surface of the glass for 24 hours, after which the wash resistance of the coating was determined by means of a brush according to the standard SFS 3755, when applicable. The pieces to be tested were brushed 5 000 times. After each 1 000 times, a contact angle was measured from the pieces, and the durability of the coatings was assessed by means of it. The test conditions were as follows:
Device: Braive Instruments
Brush: DIN 53778
Lubricant: water
Temperature: 23 0C
[0037] In Table 1 , sample A represents the coating composition according to the invention, prepared in the manner described in Example 1. Sample B is a reference composition in which formulation 2 was prepared in the same way as in Example 1 but formulation 1 was prepared by adding 0.5 g of 33.3-% hydrochlorid acid to 10 g of ultrapurified water. Formulations 1 and 2 were combined, after which the obtained composition was allowed to be activated for 10 hours. Likewise, sample C is a reference composition, i.e. the silicone-based acid-activated product DYNASYLAN® F 8263 from the company Degussa AG.
[0038] The results of the test are given in Table 1 , The contact angie of the water drop remaining on the glass was measured in the test.
TABLE 1 : CONTACT ANGLES
[0039] It turned out in the test that water was gathered as larger drops on the glass coated with the coating composition according to the invention than on the glasses coated with the reference compositions. Generally speaking, iarge drops move, as known, more easily on the surface of glass than small drops, although the contact angle of small drops is larger than that of large drops. A large contact angle, in turn, indicates that the surface energy of the drop is low, which means that the drop moves easily on the surface. A small contact angle, in turn, refers to high surface energy, in which case the drop moves more slowly on the surface. Although the contact angle of the coating composition according to the invention (sample A) was smaller than the contact angle of reference sample B before the test was started, the surface energy in sample A was, surprisingly, lower than in B from the start, which is shown by formation of large drops on the glass surface. Thus, when the coating composition according to the invention is used, self-
cleaning of the glass is more efficient than with reference compositions. This effect has a practical significance for instance when using the coating in the windscreen of a car, in which case drizzle or washing water does not remain as small drops on the surface of the glass, which would deteriorate visibility, but it is gathered as larger drops on the surface. Deteriorated visibility is particularly harmful when one is driving in the dark, in which case the reflection of externa! lights from small drops may be significant.
[0040] It can also be seen from the results that the contact angle of the coating composition according to the invention (sample A) became, surprisingly, even larger as the glass brushing times increased. It can be assumed that decomposition of the gel structure takes place in sample B during the test, and the gel structure is not capable of "correcting itself", i.e. being reformed on the surface of the substrate. No such decomposition is observed in sample A but the gel structure is capable of being reformed over time. This phenomenon can partly be explained by the coating composition according to the invention being gelled more slowly than an acid-activated coating composition (sample B).
[0041] The results thus show that the coating composition according to the invention was preserved weli on the glass surface. In contrast, a coating containing acid-activated fiuoroalkylsilane is not preserved on the glass in the same way but some wear can be observed on the basis of the test results.
[0042] It is obvious to a person skilled in the art that as the technology advances, the basic idea of the invention can be implemented in a plurality of different ways. The invention and its embodiments are thus not confined to the above examples but may vary within the claims.
Claims
1. An acid-free coating composition comprising one or more fiuoroalkylsiiane compounds, volatile substance, salt and water.
2. A coating composition according to claim 1 , wherein the amount of sϋane compound in the composition is 0.1 to 10% by weight, preferably 2 to 3% by weight, more preferably 0.5 to 1.5% by weight, based on the total composition.
3. A coating composition according to claim 1 or 2, wherein the volatile substance is alcohol, ester or a mixture thereof.
4. A coating composition according to claim 3, wherein the alcohol is isopropanol.
5. A coating composition according to any one the preceding claims, wherein the amount of volatile substance is 50 to 80% by weight, preferably 70 to 80% by weight, based on the total composition.
6. A coating composition according to any one of the preceding claims, wherein the salt is NaCI.
7. A coating composition according to any one of the preceding claims, wherein the amount of salt is 0.25 to 0.75% by weight.
8. A coating composition according to any one of the preceding claims, wherein the amount of water is 5 to 45% by weight, preferably approximately 20% by weight.
9. A coating composition according to any one of the preceding claims, further comprising suspending agent.
10. A coating composition according to claim 9, wherein the suspending agent is alcohol, ketone, ester or hydrocarbon.
11. A coating composition according to claim 9 or 10, wherein the amount of suspending agent is 4 to 60% by weight, based on the total composition.
12. A process for preparing a coating composition according to any one of claims 1 to 11 , the process comprising
- mixing the salt and the water to obtain a salt solution
- mixing the silane compound and the volatile substance to obtain a mixture
- mixing said salt solution and said mixture with each other to obtain a raw composition - allowing the raw composition to stand for 38 to 72 hours, obtaining thus an activated coating composition
- adding, if desired, suspending agent to the activated coating composition.
13. The use of a composition according to any one of claims 1 to 11 or of a coating composition prepared with a process according to claim 12 on the surface of a substrate, wherein a durable, easy-to-clean and dirt-repelient surface is provided.
14. The use according to claim 13, wherein the substrate is glass, ceramics, rock, concrete, metal, rubber, thermoplastic or thermosetting plastic.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09769422.8A EP2294153A4 (en) | 2008-06-27 | 2009-06-17 | Coating composition and process for preparing it |
| AU2009264158A AU2009264158A1 (en) | 2008-06-27 | 2009-06-17 | Coating composition and process for preparing it |
| JP2011515497A JP2011525938A (en) | 2008-06-27 | 2009-06-17 | Coating composition and method for producing the same |
| CN2009801247117A CN102076798A (en) | 2008-06-27 | 2009-06-17 | Coating composition and process for preparing it |
| MX2010014244A MX2010014244A (en) | 2008-06-27 | 2009-06-17 | Coating composition and process for preparing it. |
| BRPI0914716A BRPI0914716A2 (en) | 2008-06-27 | 2009-06-17 | acid-free coating composition, process for preparing a coating composition, and use of a composition. |
| US13/000,589 US20110132229A1 (en) | 2008-06-27 | 2009-06-17 | Coating composition and process for preparing it |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI20085659A FI122754B (en) | 2008-06-27 | 2008-06-27 | Coating composition and process for its preparation |
| FI20085659 | 2008-06-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2009156579A1 true WO2009156579A1 (en) | 2009-12-30 |
Family
ID=39589420
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/FI2009/050528 WO2009156579A1 (en) | 2008-06-27 | 2009-06-17 | Coating composition and process for preparing it |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20110132229A1 (en) |
| EP (1) | EP2294153A4 (en) |
| JP (1) | JP2011525938A (en) |
| KR (1) | KR20110025983A (en) |
| CN (1) | CN102076798A (en) |
| AU (1) | AU2009264158A1 (en) |
| BR (1) | BRPI0914716A2 (en) |
| FI (1) | FI122754B (en) |
| MX (1) | MX2010014244A (en) |
| RU (1) | RU2011102701A (en) |
| WO (1) | WO2009156579A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR20220100627A (en) | 2022-08-01 | 2024-03-12 | Παπαδοπουλος Νικολαος-Ξαφακης Σωτηριος Ομορρυθμη Εταιρεια, | Method of developing protective and easy-to-clean high-resistance nanocoating systems for multiple substrates |
| EP4442771A1 (en) | 2023-04-05 | 2024-10-09 | Papadopoulos Nikolaos-Xafakis Sotirios G.P. | Antifouling and antistatic coatings through automated application |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6361871B1 (en) * | 1999-02-03 | 2002-03-26 | Degussa Ag | Composition of organofluorine-functional silanes and/or siloxanes, process for preparing it and its use |
| US20020081385A1 (en) * | 2000-10-10 | 2002-06-27 | Fraunhofer-Gesellschaft Zur Forderung Der Angewandten Forschung E.V. | Method for producing fluoroalkyl-functionalized silane coatings |
| WO2005014742A1 (en) * | 2003-07-22 | 2005-02-17 | Leibniz-Institut Für Neue Materialien Gemeinnützige Gmbh | Liquid-repellent coating composition and coating having high alkali resistance |
| WO2007068545A2 (en) * | 2005-12-15 | 2007-06-21 | Evonik Degussa Gmbh | Storage-stable coating composition for abrasion-resistantly and weathering-stably providing smooth inorganic surfaces with easy-to-clean properties |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4118184A1 (en) * | 1991-06-03 | 1992-12-10 | Inst Neue Mat Gemein Gmbh | COATING COMPOSITIONS BASED ON FLUORIC INORGANIC POLYCONDENSATES, THEIR PRODUCTION AND THEIR USE |
| MXPA06010676A (en) * | 2004-03-19 | 2007-02-21 | Doerken Ewald Ag | Compressed-air conditioner. |
-
2008
- 2008-06-27 FI FI20085659A patent/FI122754B/en active IP Right Grant
-
2009
- 2009-06-17 JP JP2011515497A patent/JP2011525938A/en active Pending
- 2009-06-17 WO PCT/FI2009/050528 patent/WO2009156579A1/en active Application Filing
- 2009-06-17 US US13/000,589 patent/US20110132229A1/en not_active Abandoned
- 2009-06-17 BR BRPI0914716A patent/BRPI0914716A2/en not_active IP Right Cessation
- 2009-06-17 CN CN2009801247117A patent/CN102076798A/en active Pending
- 2009-06-17 KR KR1020117001839A patent/KR20110025983A/en not_active Application Discontinuation
- 2009-06-17 AU AU2009264158A patent/AU2009264158A1/en not_active Abandoned
- 2009-06-17 EP EP09769422.8A patent/EP2294153A4/en not_active Withdrawn
- 2009-06-17 RU RU2011102701/05A patent/RU2011102701A/en unknown
- 2009-06-17 MX MX2010014244A patent/MX2010014244A/en not_active Application Discontinuation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6361871B1 (en) * | 1999-02-03 | 2002-03-26 | Degussa Ag | Composition of organofluorine-functional silanes and/or siloxanes, process for preparing it and its use |
| US20020081385A1 (en) * | 2000-10-10 | 2002-06-27 | Fraunhofer-Gesellschaft Zur Forderung Der Angewandten Forschung E.V. | Method for producing fluoroalkyl-functionalized silane coatings |
| WO2005014742A1 (en) * | 2003-07-22 | 2005-02-17 | Leibniz-Institut Für Neue Materialien Gemeinnützige Gmbh | Liquid-repellent coating composition and coating having high alkali resistance |
| WO2007068545A2 (en) * | 2005-12-15 | 2007-06-21 | Evonik Degussa Gmbh | Storage-stable coating composition for abrasion-resistantly and weathering-stably providing smooth inorganic surfaces with easy-to-clean properties |
Non-Patent Citations (1)
| Title |
|---|
| See also references of EP2294153A4 * |
Also Published As
| Publication number | Publication date |
|---|---|
| FI122754B (en) | 2012-06-29 |
| EP2294153A1 (en) | 2011-03-16 |
| RU2011102701A (en) | 2012-08-10 |
| BRPI0914716A2 (en) | 2015-10-20 |
| JP2011525938A (en) | 2011-09-29 |
| EP2294153A4 (en) | 2014-01-01 |
| US20110132229A1 (en) | 2011-06-09 |
| FI20085659A (en) | 2009-12-28 |
| MX2010014244A (en) | 2011-06-20 |
| KR20110025983A (en) | 2011-03-14 |
| AU2009264158A1 (en) | 2009-12-30 |
| CN102076798A (en) | 2011-05-25 |
| FI20085659A0 (en) | 2008-06-27 |
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