EP1397451A2 - Revetements permanents hydrophobes appliques sur des substrats et leur procede de production - Google Patents

Revetements permanents hydrophobes appliques sur des substrats et leur procede de production

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Publication number
EP1397451A2
EP1397451A2 EP02729876A EP02729876A EP1397451A2 EP 1397451 A2 EP1397451 A2 EP 1397451A2 EP 02729876 A EP02729876 A EP 02729876A EP 02729876 A EP02729876 A EP 02729876A EP 1397451 A2 EP1397451 A2 EP 1397451A2
Authority
EP
European Patent Office
Prior art keywords
groups
coatings according
coatings
crosslinking
resin component
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.)
Withdrawn
Application number
EP02729876A
Other languages
German (de)
English (en)
Inventor
Dieter Lehmann
Dietmar Appelhans
Michaela Gedan-Smokla
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Leibniz Institut fuer Polymerforschung Dresden eV
Original Assignee
Leibniz Institut fuer Polymerforschung Dresden eV
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 Leibniz Institut fuer Polymerforschung Dresden eV filed Critical Leibniz Institut fuer Polymerforschung Dresden eV
Publication of EP1397451A2 publication Critical patent/EP1397451A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/06—Polyurethanes from polyesters
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/46—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen
    • C08G18/4607—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen having halogens
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/798—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing urethdione groups
    • 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
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
    • 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
    • C08G2150/00—Compositions for coatings
    • C08G2150/20—Compositions for powder coatings
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]

Definitions

  • the invention relates to the field of chemistry and relates to hydrophobic permanent coatings on substrates which can be used, for example, for the production of lacquer layers, and a process for their production.
  • Liquid coating systems which contain solvents and therefore do not meet the more recent requirements for zero emissions. Furthermore, the newer requirements consist in surface properties that are as water, oil, dust, dirt and scratch resistant as possible, as well as improved sliding properties of coated surfaces.
  • the coating surfaces have previously been made hydrophobic by physically embedded or chemically bound perfluorinated additives.
  • an ultrahydrophobic layer property is understood to mean that the contact angle is> 130 ° with a drop of water attached.
  • a perfluoroalkyl group-containing coating agent is known as a polymer solution based on perfluoroalkyl group-containing acrylic acid esters with alkylated and aromatic side groups and an isocyanate as crosslinking agent / hardener.
  • the surface hydrophobicity is specified with a contact angle of ⁇ 117 °. This means that no ultrahydrophobic properties of the coated surface are achieved.
  • the synthesis of poly (amidurethane) block copolymers with perfluoroalkyl-containing side groups in solution for use as coating agents is known. This process is very complex and the contact angles achieved gave values of ⁇ 116 °.
  • these polymers are coated with polyurethanes in various proportions of perfluoroalkyl-containing mass after application to the one to be coated
  • Compounds or perfluoroalkylated polyether diols can be obtained as a soft chain segment with free diisocyanates in the presence of dibutyltin dilaurate and optionally hydroxyl-containing binders to form prepolymers.
  • Perfluoroalkyl compounds based on polyether diols have been realized, which have been tested as coating agents.
  • the object of the invention is to provide permanent coatings which have hydrophobic to ultrahydrophobic properties and a simple and uncomplicated process for their production.
  • the perfluoroalkyl group-containing coating compositions consist of the hardener component (A) and resin component (B) with special functional groups which are processed into a crosslinked layer and which are coupled to the surface area of the substrate. This is achieved according to the invention by at least one two-stage or multi-stage reaction, which can take place in parallel and / or in succession, on the one hand by means of the thermal filming of the perfluoroalkyl group-containing coating agents on the substrate surface, a chemical coupling between coating agent and substrate surface and on the other hand by selection of the curing process Partial crosslinking and crosslinking of the perfluoroalkyl group-containing coating compositions are advantageously effected in the range ⁇ 160 ° C.
  • the resulting cured perfluoroalkyl group-containing coatings have permanently hydrophobic to ultrahydrophobic surface properties.
  • the individual sub-stages of filming and crosslinking with the coupling between coating agents containing perfluoroalkyl groups and substrate surface can advantageously be:
  • the perfluoroalkyl group-containing coating agents used can be applied to the substrate surfaces as a melt, powder, dispersion or solution.
  • the hardener component (A) contained in the perfluoroalkyl group-containing coating compositions for the catalyzed and / or uncatalyzed thermal crosslinking is advantageously (poly) epoxy and / or blocked (poly) isocyanate and / or (poly) uretdione compounds.
  • the hardener component used has chemically coupled, pendant and / or terminal perfium alkyl groups with at least one trifluoromethyl end group. In the event that the resin component (B) has such perfium alkyl groups, the hardener component (A) can also have no perfioroalkyl groups.
  • the hardener component (A) contained in the perfluoroalkyl group-containing coating compositions for thermal filming and catalyzed and / or uncatalyzed thermal pre-crosslinking and simultaneous or subsequent photochemical and / or subsequent radiation-chemical crosslinking are advantageously (poly) epoxy and / or blocked (poly ) isocyanate and / or (poly) uretdione compounds for the pre-crosslinking and coupling reaction to the substrate surface and low molecular weight and / or oligomeric and / or polymeric photoinitiators for the photochemical crosslinking reaction and optionally additional olefinically unsaturated groups, preferably based on (meth) acrylate for the photochemical and / or radiation-chemical crosslinking.
  • the hardener component used has chemically coupled, pendant and / or terminal perfium alkyl groups with at least one trifluoromethyl end group.
  • the hardener component (A) can also have no perfioroalkyl groups.
  • the hardener component (A) contained in the perfluoroalkyl group-containing coating compositions for thermal filming and simultaneous or subsequent photochemical and / or subsequent radiation-chemical crosslinking is advantageously low-molecular and / or oligomeric and / or polymeric photoinitiators and, if appropriate, additionally olefinically unsaturated groups, preferably based on (meth) acrylate.
  • the hardener component used has chemically coupled, pendant and / or terminal perfium alkyl groups with at least one trifluoromethyl end group. In the event that the resin component (B) is such Has Perfiuoralkyl distribution, the hardener component (A) may not have Perfiuoralkyl fate.
  • the hardener component (A) has additional epoxy and / or blocked isocyanate and / or uretdione groups to form covalent bonds with functional groups on the substrate surface.
  • additional epoxy and / or blocked isocyanate and / or uretdione groups to form covalent bonds with functional groups on the substrate surface.
  • amino and / or hydroxy and / or carboxylic acid groups can be present in the hardener component (A), which form covalent bonds with remaining reactive groups on the substrate surface.
  • the resin component (B) contained in the perfluoroalkyl group-containing coating compositions for the various process steps for thermal filming, for partial crosslinking and complete crosslinking and for coupling between perfluoroalkyl group-containing coating compositions and substrate surfaces are differently functionalized polymers.
  • the resin component (B) contained in the perfluoroalkyl group-containing coating compositions for the catalyzed and / or uncatalyzed, thermal crosslinking is advantageously polyester and / or polyurethane and / or poly (meth) acrylate substance classes with functional groups in the form of amino - And / or hydroxy and / or carboxylic acid groups.
  • the resin component (B) used has chemically coupled, pendant and / or terminal Perfiuoralkyl phenomenon with at least one trifluoromethyl end group.
  • the resin component (B) can also have no perfioralkyl groups.
  • the functional groups present in the form of amino and / or hydroxy and / or carboxylic acid groups are advantageously used for complete crosslinking and for the formation of covalent bonds with the substrate surface, which form covalent bonds with remaining reactive groups on the substrate surface.
  • the resin component (B) contained in the perfluoroalkyl group-containing coating compositions for thermal filming and catalyzed and / or uncatalyzed, thermal partial crosslinking and simultaneous or subsequent photochemical and / or subsequent radiation-chemical crosslinking advantageously around polyester and / or polyurethane and / or poly (meth) acrylate substance classes with functional groups in the form of amino and / or hydroxyl and / or carboxylic acid groups for partial crosslinking and for the formation of covalent bonds with the substrate surface which form remaining covalent bonds in the reactive groups of the substrate surface, and additionally have olefinically unsaturated groups, preferably based on (meth) acrylate, for photochemical and / or radiation-chemical crosslinking.
  • the resin component (B) used has chemically coupled, pendant and / or terminal Perfiuoralkyl phenomenon with at least one trifluoromethyl end group.
  • the resin component (B) can also have no perfioroalkyl groups.
  • the resin component (B) contained in the perfluoroalkyl group-containing coating compositions for thermal filming and simultaneous or subsequent photochemical and / or subsequent radiation-chemical crosslinking are polymers with olefinically unsaturated groups, preferably based on (meth) acrylate for the photochemical and / or radiation-chemical ones Crosslinking, and with additional functional groups in the form of amino and / or hydroxyl and / or carboxylic acid groups to form covalent bonds with remaining reactive groups on the substrate surface.
  • the resin component (B) used has chemically coupled, pendant and / or terminal Perfiuoralkyl phenomenon with at least one trifluoromethyl end group. In the event that the hardener component (A) has such perfium alkyl groups, the resin component (B) can also have no perfioralkyl groups.
  • the additives contained in the perfluoroalkyl group-containing coating compositions for the various process steps for thermal filming, for partial crosslinking and complete crosslinking and for the coupling between perfluoroalkyl group-containing coating compositions and the substrate surfaces are known additives and auxiliaries which are added in known proportions by mass. Such additives can be used, for example, for the production of the perfluoroalkyl group-containing coating compositions as a melt, powder, dispersion or solution.
  • the catalysts contained in the perfluoroalkyl group-containing coating compositions for the various process steps for thermal filming, for partial crosslinking and complete crosslinking and for coupling between perfluoroalkyl group-containing coating compositions and substrate surfaces are known catalysts which are in the customary range of ⁇ 3% by mass, based on the Total mass of hardener component (A) and resin component (B) can be used. It must be taken into account here that the catalysts used for crosslinking and coupling between coating agents containing perfluoroalkyl groups and functionalized substrate surfaces are effective and are not deactivated in order to be able to implement the parallel and / or successive multi-stage reactions of the various process steps.
  • perfluoroalkyl group-containing substances which are used as terminal and / or lateral perfiuoralkyl groups with at least one trifluoromethyl end group chemically coupled in hardener component (A) and / or resin component (B) are present in the perfluoroalkyl group-containing coating compositions in amounts of 0.1-70% by mass and preferably of 1, 0 to 30 percent by mass.
  • the perfluoroalkyl group-containing substances which are present as terminal and / or pendant perfiuoralkyl groups with at least one trifluoromethyl end group chemically coupled in hardener component (A) and / or resin component (B) are in the perfluoroalkyl group-containing coating compositions via one or more, also different spacer chains with a chain length of 1 up to 60 carbon atoms, where the spacer chain can be unbranched and / or branched and also functional groups such as ether and / or carboxylic acid ester and / or carboxylic acid amide and / or sulfonic acid amide and / or imide and / or urethane and / or May contain sulfide and / or sulfone groups, among others, or bound directly to the hardener component (A) and / or resin component (B).
  • Perfluoroalkyl group-containing substances are used in the perfluoroalkyl group-containing coating compositions as perfiuoralkyl groups with at least one trifluoromethyl end group and having chain lengths of 2 to 25 carbon atoms.
  • the perfiuoralkyl groups are directly via a functional group and / or via a functionalized alkylene chain and / or via a functionalized arylene chain and / or via a functionalized alkylene arylene chain and / or via a functionalized alkylene arylene alkylene chain and / or via a functionalized arylene alkylene chain and / or via a functionalized arylene alkylene arylene chain to the hardener component (A) and / or resin component (B) chemically bound. All functionalized chains can still carry cycloaliphatic and / or heterocyclic units.
  • the perfluoroalkyl group-containing substances which are present as terminal and / or lateral perfiuoralkyl groups with at least one trifluoromethyl end group chemically coupled in hardener component (A) and / or resin component (B), can be used in the perfluoroalkyl group-containing coating compositions as perfluoroalkylcarboxamide derivatives and / or perfluoroalkylsulfonic acid amide derivatives functional group in the form of an alkylene hydroxy group, alkylene amino group, alkylene carboxylic acid group,
  • Alkylene carboxylic acid ester group alkylene epoxy group except in the presence of amino groups, alkylene isocyanate group except in the presence of amino and hydroxy groups, alkylene uretdione group or alkylene carbonate group, but also defined mixtures of such perfluoroalkylcarboxamide derivatives and / or perfluoroalkylsulfonic acid amide derivatives for the production of modified
  • Hardener components (A) and / or resin components (B) are used.
  • the functionalized alkylene chains can have cycloaliphatic and / or aromatic and / or heterocyclic units.
  • perfluoroalkyl group-containing substances which are present as terminal and / or pendant perfiuoralkyl groups with at least one trifluoromethyl end group chemically coupled in the hardener component (A) and / or the resin component (B) can be used in the perfluoroalkyl group-containing coating compositions as perfluoroalkyl carboxylic acid, perfluoroalkyl carboxylic acid esters,
  • Perfluoroalkylcarboxylic acid halides or perfluoroalkylsulfonic acid halides can be used for the synthesis of modified hardener components (A) and resin components (B).
  • Perfiuoralkyl groups with at least one trifluoromethyl end group can be present in the perfluoroalkyl group-containing coating compositions as a perfluoroalkylalkylene derivative and / or perfluoroalkylarylene derivative with at least one functional group.
  • Functional groups of the point of connection between perfluoroalkyl group-containing substances and hardener component (A) and / or resin component (B) are advantageously ether, ester, urethane, urea, carboxamide, imide, sulfonamide, sulfone groups, C-C single or double bonds.
  • the substrate surface is a surface which, after various known cleaning or activation steps, carries functional groups which form a chemical coupling between the perfluoroalkyl group-containing coating compositions and the substrate surface.
  • Functional groups on the substrate surface are advantageously hydroxyl, amino, epoxy, isocyanate, acid groups, in particular carboxylic acid groups, ester, blocked isocyanate or uretdione groups.
  • the coupling listed in the perfluoroalkyl group-containing coating compositions for thermal filming, for partial crosslinking and complete crosslinking and for the coupling between the perfluoroalkyl group-containing coating compositions and the substrate surface is the formation of covalent bonds in addition to noncovalent bonds in the form of ionic / electrostatic and / or van der-Waals bonds.
  • the coating agent containing perfluoroalkyl groups consisting of a hardener component (A) and a resin component (B), is applied as a melt, powder, dispersion or solution to a surface, with filming while supplying energy with or without partial crosslinking of the layer components and at least one Partial coupling of this layer with the surface area of the substrate is carried out in one or more stages and the complete crosslinking of the layer is then carried out again with the supply of energy.
  • the supply of energy is advantageously understood to mean a thermal treatment or photochemical and / or radiation-chemical treatment.
  • filming means a partial or complete film formation or a layer application of the perfluoroalkyl group-containing coating agent on a substrate surface.
  • thermal filming and subsequent or simultaneous thermally catalyzed and / or uncatalyzed partial crosslinking in a manufacturing process in which the perfluoroalkyl group-containing coating agent on the substrate surface to be coated is heated for a short time to ⁇ 130 ° C and, after cooling, a forming process with subsequent radiation chemical Networking takes place.
  • This advantageous process control by selecting the individual process steps can be improved by selected known catalysts or catalyst systems which, at temperatures below 150 ° C., couple between the coating agent containing perfluoroalkyl groups and the Allow substrate surface and a partial crosslinking of the perfluoroalkyl group-containing coating agent.
  • Resin component (B) contains a total of 8% by mass of chemically coupled perfluorooctanoic acid amide.
  • the additives and auxiliaries white pigment (TiO 2 ) 0.6 mass% and a flow aid (Acronal 4F) 0.6 mass% and catalyst (zinc acetylacetonate, 1 mass%) are added to this mass in succession.
  • the homogenized mass is quenched by introducing it into liquid nitrogen, comminuted in a laboratory grinding plant with a separator with cooling and the powder dried at 30 ° C. in vacuo.
  • the powder thus produced is applied electrostatically to a coated substrate surface containing uretdione groups.
  • the thermal filming and partial coupling between the perfluoroalkyl group-containing coating agent and the coated substrate surface is carried out at 130 ° C./10 minutes and the thermal crosslinking at 155 ° C./25 minutes.
  • Contact angle measurements with water on the substrate surface showed a progression angle of 130 °. Examinations of cross cuts prove good adhesion.
  • the perfluoroalkyl group-containing hardener component (Aa) and hardener component (Ab) [in a ratio of 2: 1, both consisting of a polyepoxide; Aa and Ab 25.0 mass%] and the perfluoroalkyl group-containing resin component (B) [hydroxyl-terminated polyester, 75.0 mass%] in the melt Homogenized 90 ° C. A total of 12% by mass of chemically coupled perfluorooctanoic acid amide are contained.
  • the additives and auxiliaries white pigment (TiO 2 ) 0.6 mass% and a flow aid (Acronal 4F) 0.6 mass% and catalyst (2-methylimidazole, 1 mass%) are added to this mass in succession.
  • the homogenized mass is quenched by introducing it into liquid nitrogen, comminuted in a laboratory grinding plant with a separator with cooling and the powder dried at 30 ° C. in vacuo.
  • the powder produced in this way is applied electrostatically to a pretreated structured aluminum surface and heated to 110 ° C./10 minutes for thermal filming and partial coupling and to 160 ° C./15 minutes for thermal crosslinking.
  • Contact angle measurements with water on the substrate surface showed a progression angle of 135 °. Examinations of cross cuts prove good adhesion.
  • the hardener component (A) and the perfluoroalkyl group-containing, thermally and radiation-chemically curable resin component (B) are homogenized in a ratio of 1: 3 at 90 ° C. in accordance with Example 1. Additives, auxiliaries and catalysts are added to this mass in succession. Resin component (B) contains a total of 7% by mass of chemically coupled perfluorooctanoic acid amide.
  • the homogenized mass is quenched by introducing it into liquid nitrogen, comminuted in a laboratory grinding plant with a separator with cooling and the powder dried at 30 ° C. in vacuo.
  • the powder thus produced is applied electrostatically to a primed substrate surface containing epoxy groups and heated to 120 ° C./5 minutes for thermal filming, partial crosslinking and coupling.
  • the substrate surface is then cross-linked with a radiation dose of 15 kGy.
  • Contact angle measurements with water on the substrate surface showed progression angles from 125 to 130 °. Examinations of cross cuts prove good adhesion.
  • the substrate is heated to 120 ° C / 20 minutes for thermal filming and coupling.
  • the substrate surface is then irradiated with a radiation dose of 11 kGy.
  • Contact angle measurements with water on the substrate surface showed a progression angle of 125 °. Examinations of cross cuts prove good adhesion.
  • the perfluoroalkyl group-containing hardener component (Aa) and hardener component (Ab) [in a ratio of 2: 1, both consisting of a polyepoxide; Aa and Ab 25.0 mass%] and the perfluoroalkyl group-containing photocrosslinkable resin component (B) [hydroxyl-terminated polyester with methacrylate groups, 75.0 mass%] in the melt at 90 ° C.
  • a total of 14 mass% of chemically coupled perfluorooctanoic acid amide are contained.
  • a flow aid (Acronal 4F) 0.6 mass% and catalyst (2-methylimidazole, 0.5 mass%) and 2.0 mass% benzophenone are added to this mass in succession as a photocrosslinker.
  • the coating agent is applied as an aqueous dispersion to a primed substrate surface containing epoxy groups.
  • the substrate surface is heated to 130 ° C / 20 minutes for thermal filming, partial crosslinking and coupling.
  • the substrate surface is then crosslinked by UV radiation (photochemical crosslinking, 3 minutes). Contact angle measurements with water on the substrate surface showed a progression angle of 130 - 140 °. Examinations of cross cuts prove good adhesion.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne le domaine de la chimie et, plus précisément, les revêtements qui peuvent être utilisés, par exemple, pour produire des couches de vernis. L'invention concerne également leur procédé de production. L'invention vise à produire des revêtements permanents ayant des propriétés hydrophobes à ultrahydrophobes. Pour ce faire, les revêtements permanents hydrophobes sont composés d'une couche réticulée composée d'une composante durcisseur (A) et d'une composante résine (B), sachant que (A) et/ou (B) contiennent des groupes perfluoroalkyle latéraux et/ou terminaux couplés chimiquement et au moins un groupe terminal trifluorométhyle, avec un couplage entre la couche et la zone superficielle du substrat. A cet effet, on utilise également un procédé, selon lequel on applique sur une surface l'agent de revêtement contenant des groupes perfluoroalkyle sous forme de matière fondue, poudre, dispersion ou solution. Ainsi, on obtient la formation d'un film par apport d'énergie, avec ou sans réticulation partielle; au moins un couplage partiel et enfin, à nouveau par apport d'énergie, la réticulation complète de la couche .
EP02729876A 2001-04-25 2002-04-19 Revetements permanents hydrophobes appliques sur des substrats et leur procede de production Withdrawn EP1397451A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10120989 2001-04-25
DE2001120989 DE10120989A1 (de) 2001-04-25 2001-04-25 Hydrophobe permanente Beschichtungen auf Substraten und Verfahren zu ihrer Herstellung
PCT/DE2002/001494 WO2002087784A2 (fr) 2001-04-25 2002-04-19 Revetements permanents hydrophobes appliques sur des substrats et leur procede de production

Publications (1)

Publication Number Publication Date
EP1397451A2 true EP1397451A2 (fr) 2004-03-17

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Application Number Title Priority Date Filing Date
EP02729876A Withdrawn EP1397451A2 (fr) 2001-04-25 2002-04-19 Revetements permanents hydrophobes appliques sur des substrats et leur procede de production

Country Status (5)

Country Link
US (1) US7141276B2 (fr)
EP (1) EP1397451A2 (fr)
AU (1) AU2002302343A1 (fr)
DE (1) DE10120989A1 (fr)
WO (1) WO2002087784A2 (fr)

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DE102009001145A1 (de) * 2009-02-25 2010-09-09 Leibniz-Institut Für Polymerforschung Dresden E.V. Verfahren zur Aushärtung und Oberflächenfunktionalisierung von Formteilen
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JP2014512417A (ja) 2011-02-21 2014-05-22 ロス テクノロジー コーポレーション． 低ｖｏｃ結合剤系を含む超疎水性および疎油性被覆物
WO2013090939A1 (fr) 2011-12-15 2013-06-20 Ross Technology Corporation Composition et revêtement pour une performance superhydrophobe
WO2014003852A2 (fr) 2012-06-25 2014-01-03 Ross Technology Corporation Revêtements élastomères ayant des propriétés hydrophobes et/ou oléophobes
CN108822722B (zh) * 2018-07-29 2020-03-06 湖南科技大学 一种基于荷叶仿生的疏水性聚氨酯海洋防污涂层材料及制备方法

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WO2002087784A2 (fr) 2002-11-07
DE10120989A1 (de) 2002-11-07
US20040126589A1 (en) 2004-07-01
US7141276B2 (en) 2006-11-28
WO2002087784A3 (fr) 2003-01-03

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