WO2003014232A1 - Materiau pour produire des revetements resistants a l'usure, hydrophobes et/ou oleophobes - Google Patents

Materiau pour produire des revetements resistants a l'usure, hydrophobes et/ou oleophobes Download PDF

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Publication number
WO2003014232A1
WO2003014232A1 PCT/DE2002/002667 DE0202667W WO03014232A1 WO 2003014232 A1 WO2003014232 A1 WO 2003014232A1 DE 0202667 W DE0202667 W DE 0202667W WO 03014232 A1 WO03014232 A1 WO 03014232A1
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WO
WIPO (PCT)
Prior art keywords
substrate
acid
hydrophobic
temperature
material according
Prior art date
Application number
PCT/DE2002/002667
Other languages
German (de)
English (en)
Inventor
Stefan Sepeur
Frank Gross
Jan Interwies
Original Assignee
Nano-X Gmbh
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Nano-X Gmbh filed Critical Nano-X Gmbh
Publication of WO2003014232A1 publication Critical patent/WO2003014232A1/fr

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Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING 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
    • C09D183/00Coating 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
    • C09D183/04Polysiloxanes
    • C09D183/08Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
    • CCHEMISTRY; METALLURGY
    • C03GLASS; MINERAL OR SLAG WOOL
    • C03CCHEMICAL 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
    • C03C17/00Surface treatment of glass, not in the form of fibres or filaments, by coating
    • C03C17/28Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material
    • C03C17/30Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material with silicon-containing compounds
    • CCHEMISTRY; METALLURGY
    • C04CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04BLIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B41/00After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
    • C04B41/009After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone characterised by the material treated
    • CCHEMISTRY; METALLURGY
    • C04CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04BLIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B41/00After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
    • C04B41/45Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
    • C04B41/46Coating 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
    • C04B41/49Compounds 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
    • C04B41/4905Compounds 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
    • C04B41/4922Compounds 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
    • C04B41/4933Compounds 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
    • CCHEMISTRY; METALLURGY
    • C04CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04BLIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B41/00After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
    • C04B41/45Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
    • C04B41/46Coating 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
    • C04B41/49Compounds 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
    • C04B41/4905Compounds 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
    • C04B41/495Compounds 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 oligomers or polymers
    • C04B41/4977Compounds 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 oligomers or polymers characterised by the number of silicon atoms
    • CCHEMISTRY; METALLURGY
    • C04CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04BLIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B41/00After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
    • C04B41/80After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone of only ceramics
    • C04B41/81Coating or impregnation
    • C04B41/82Coating or impregnation with organic materials
    • C04B41/84Compounds having one or more carbon-to-metal of carbon-to-silicon linkages
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING 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
    • C09D183/00Coating 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
    • C09D183/04Polysiloxanes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING 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
    • C09D4/00Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • CCHEMISTRY; METALLURGY
    • C03GLASS; MINERAL OR SLAG WOOL
    • C03CCHEMICAL 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
    • C03C2217/00Coatings on glass
    • C03C2217/70Properties of coatings
    • C03C2217/76Hydrophobic and oleophobic coatings

Definitions

  • the present invention relates to a material for producing abrasion-resistant, hydrophobic and / or oleophobic coatings and their use.
  • EP 0 109 171 discloses fluorocarbon resins or generally fluorochemical copolymers and cardboards and textile fibers coated therewith.
  • the coating materials known from the prior art at least partially have a comparatively good water, oil and / or dirt-repellent effect, they are still in need of improvement. Improvements are possible, in particular with regard to the abrasion resistance and chemical resistance that can be achieved. This is particularly important in the areas in which the coating materials are to be used for coating ceramic floor tiles or chrome surfaces in the sanitary area.
  • the surfaces coated with the coating materials known from the prior art frequently also show a loss of the hydrophobic effect in the strongly basic medium.
  • the present object is achieved by a material with the features of claim 1 and a use with the features of claim 6.
  • a hydrophobic and / or oleophobic group is understood to mean a branched or unbranched alkyl and / or polyfluoroalkyl and / or perfluoroalkyl group. These groups can be straight-chain or branched or can also contain saturated, unsaturated or aromatic cyclic groups.
  • the hydrophobic and / or oleophobic groups can furthermore have substituents, the substituents preferably having functionalities which later crosslink e.g. enable by UV or heat-induced polymerization reactions. Examples of such substituents are generally substituents e.g. with vinyl groups or the like. Moreover, such groups capable of crosslinking are familiar to the person skilled in the art from the prior art mentioned at the beginning.
  • the abrasion resistance of coatings which are produced from the material according to the invention and are based on silanes with hydrophobic and / or oleophobic groups is increased because it has previously been assumed that longer chain lengths are used for the hydrophobic and / or oleophobic groups tend to reduce abrasion resistance. It is preferred if the chain length of the at least one alkyl group contained in the corresponding silane and / or polyfluoroalkyl and / or perfluoroalkyl group is between 10 and 30 carbon atoms, a chain length of 12 to 20 carbon atoms being particularly preferred on account of the availability of the corresponding starting compounds and the ease of handling.
  • the material according to the invention for producing abrasion-resistant hydrophobic and / or oleophobic coatings generally contains the abovementioned silane in a solvent and / or emulsifier. Due to economic, ecological and procedural conditions, it is preferred if this solvent and / or emulsifying agent is water or at least has a high water content. Aqueous solutions of alcohols such as ethanol, methanol, propanol, isopropanol and / or butanol (in all its isomeric forms) are therefore also particularly good as solvents and / or emulsifiers and thus as a constituent of the material according to the invention for producing abrasion-resistant, hydrophobic and / or oleophobic coatings.
  • alcohols such as ethanol, methanol, propanol, isopropanol and / or butanol (in all its isomeric forms) are therefore also particularly good as solvents and / or emulsifiers and thus as
  • the material for producing abrasion-resistant, hydrophobic and / or oleophobic coatings furthermore contains a compound which acts as an activator on the silane contained in the material and already described, which is in particular an alkoxysilane. It is preferred if this compound is an acid which, by protonating the oxygen of the alkoxy group, accelerates the hydrolytic cleavage of the alkoxide group. Essentially methoxy groups and ethoxy groups are used as alkoxide groups and the hydrolytic cleavage of the alkoxide group can be controlled via the acid strength of the acid used as activator. It is particularly preferred if the acid used as an activator is an inorganic acid or an organic acid, ie in particular HCl, H 2 SO 4 and H 3 PO 4 and acetic or formic acid
  • the material according to the invention has a very wide range of applications. Almost all known natural and synthetic substrates can be coated with the material according to the invention with the formation of wear-resistant hydrophobic and / or oleophobic coatings. It is therefore preferred if the substrate is a glass-like and / or ceramic substrate (e.g. glass, ceramic, enamel), a textile (e.g. Curtain fabric, awning fabric, clothing fabric), a fiber, leather, wood, a metal (e.g. chrome, brass, copper, zinc, stainless steel), a plastic, paper, cardboard or a natural material.
  • a glass-like and / or ceramic substrate e.g. glass, ceramic, enamel
  • a textile e.g. Curtain fabric, awning fabric, clothing fabric
  • a fiber leather, wood, a metal (e.g. chrome, brass, copper, zinc, stainless steel), a plastic, paper, cardboard or a natural material.
  • the surface of the same is applied during the application of the coating, i.e. has at least room temperature during the application of the material according to the invention for producing abrasion-resistant, hydrophobic and / or oleophobic coatings.
  • the temperature for carrying out such a coating is in the range from about room temperature to about 400 ° C., preferably in the range from 40 to 200 ° C. and particularly preferably in the range from 60 to 170 ° C.
  • the preferred temperature ranges for the application of the coating result the temperature resistance of the silanes preferably used in the material according to the invention and / or the substrates to be coated.
  • the level of the temperature when applying the material according to the invention is of particular importance for the layer formation, since it determines the drying rate, i.e. affects the rate at which the solvent and / or emulsifier is removed.
  • the material according to the invention can furthermore be applied to the substrate by any coating method known to the person skilled in the art, it preferably being carried out by pouring, flooding, dipping or spinning and particularly preferably by spraying.
  • post-annealing it is advantageous if after the application of the material according to the invention so-called post-annealing takes place.
  • heat is further supplied to the substrate, advantageously in such a way that the substrate temperature is maintained. This not only enables drying, but also cross-linking of the molecules within the coating, depending on the selected conditions and the silanes used.
  • the preparation of the silanes intended for use in the material according to the invention, in particular trialkoxysilanes, is generally familiar to the person skilled in the art, so that a Description of the manufacturing process can be omitted here.
  • the coating of, for example, a sanitary ware is generally carried out as follows.

Abstract

La présente invention concerne un matériau pour produire des revêtements résistants à l'usure, hydrophobes et/ou oléophobes. Ce matériau comprend au moins un alkoxysilane qui présente au moins un groupe alkyle et/ou polyfluoroaryle et/ou perfluoroaryle avec une longueur de chaîne d'au moins 10 atomes de carbone.
PCT/DE2002/002667 2001-07-21 2002-07-19 Materiau pour produire des revetements resistants a l'usure, hydrophobes et/ou oleophobes WO2003014232A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2001135684 DE10135684A1 (de) 2001-07-21 2001-07-21 Material zur Herstellung abriebfester, hydrophober und/oder oloephober Beschichtungen
DE10135684.6 2001-07-21

Publications (1)

Publication Number Publication Date
WO2003014232A1 true WO2003014232A1 (fr) 2003-02-20

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PCT/DE2002/002667 WO2003014232A1 (fr) 2001-07-21 2002-07-19 Materiau pour produire des revetements resistants a l'usure, hydrophobes et/ou oleophobes

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Country Link
DE (1) DE10135684A1 (fr)
WO (1) WO2003014232A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102008047306A1 (de) 2008-09-16 2010-04-15 JODLAUK, Jörg Zusammensetzung temper- und sinterbarer Überzugsmassen
US7811627B2 (en) 2005-03-09 2010-10-12 Astenjohnson, Inc. Papermaking fabrics with contaminant resistant nanoparticle coating and method of in situ application
DE102009023497A1 (de) 2009-06-02 2010-12-09 Nanogate Ag Glasurzusammensetzung mit Glasplättchen verschiedener Größe
EP4317098A1 (fr) 2022-08-01 2024-02-07 Papadopoulos Nikolaos-Xafakis Sotirios G.P. Systèmes de nano-revêtement durables faciles à nettoyer

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4997738A (en) * 1988-12-01 1991-03-05 Shindengen Electric Manufacturing Co., Ltd. Electrophotographic photoreceptor having silicate with perfluoroalkyl groups in protective layer
WO1999018168A1 (fr) * 1997-10-06 1999-04-15 Saint-Gobain Vitrage Revetement hydrophobe notamment pour vitrage
WO1999019084A1 (fr) * 1997-10-15 1999-04-22 Yazaki Corporation Substrat transparent portant une couche hydrophobe anti-tache et son procede de production
EP0545201B1 (fr) * 1991-11-29 1999-10-27 PPG Industries Ohio, Inc. Surface en verre hydrofuge durable
EP1113064A1 (fr) * 1998-06-04 2001-07-04 Nippon Sheet Glass Co., Ltd. Procede pour produire un article recouvert d'un film hydrofuge, article recouvert d'un film hydrofuge, et composition liquide pour revetement a base d'un film hydrofuge
EP0799873B1 (fr) * 1996-04-02 2001-11-21 Saint-Gobain Glass France Composition pour un revêtement non-mouillable, procédé de traitement d'un vitrage à l'aide de la composition et produits obtenus

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4997738A (en) * 1988-12-01 1991-03-05 Shindengen Electric Manufacturing Co., Ltd. Electrophotographic photoreceptor having silicate with perfluoroalkyl groups in protective layer
EP0545201B1 (fr) * 1991-11-29 1999-10-27 PPG Industries Ohio, Inc. Surface en verre hydrofuge durable
EP0799873B1 (fr) * 1996-04-02 2001-11-21 Saint-Gobain Glass France Composition pour un revêtement non-mouillable, procédé de traitement d'un vitrage à l'aide de la composition et produits obtenus
WO1999018168A1 (fr) * 1997-10-06 1999-04-15 Saint-Gobain Vitrage Revetement hydrophobe notamment pour vitrage
WO1999019084A1 (fr) * 1997-10-15 1999-04-22 Yazaki Corporation Substrat transparent portant une couche hydrophobe anti-tache et son procede de production
EP1113064A1 (fr) * 1998-06-04 2001-07-04 Nippon Sheet Glass Co., Ltd. Procede pour produire un article recouvert d'un film hydrofuge, article recouvert d'un film hydrofuge, et composition liquide pour revetement a base d'un film hydrofuge

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7811627B2 (en) 2005-03-09 2010-10-12 Astenjohnson, Inc. Papermaking fabrics with contaminant resistant nanoparticle coating and method of in situ application
US9562319B2 (en) 2005-03-09 2017-02-07 Astenjohnson, Inc. Papermaking fabrics with contaminant resistant nanoparticle coating and method of in situ application
US10577744B2 (en) 2005-03-09 2020-03-03 Astenjohnson, Inc. Fabric with contaminant resistant nanoparticle coating and method of in situ application
DE102008047306A1 (de) 2008-09-16 2010-04-15 JODLAUK, Jörg Zusammensetzung temper- und sinterbarer Überzugsmassen
DE102009023497A1 (de) 2009-06-02 2010-12-09 Nanogate Ag Glasurzusammensetzung mit Glasplättchen verschiedener Größe
DE102009023497B4 (de) * 2009-06-02 2012-04-19 Nanogate Ag Glasurzusammensetzung mit Glasplättchen verschiedener Größe, Verfahren zu deren Herstellung, Verfahren zur Herstellung von glasierter Sanitärkeramik sowie Verwendung der Glasurzusammensetzung
EP4317098A1 (fr) 2022-08-01 2024-02-07 Papadopoulos Nikolaos-Xafakis Sotirios G.P. Systèmes de nano-revêtement durables faciles à nettoyer

Also Published As

Publication number Publication date
DE10135684A1 (de) 2003-02-06

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