EP3829492A1 - Inertage de surfaces de matériau par l'intermédiaire de molécules perfluorées fonctionnalisées - Google Patents

Inertage de surfaces de matériau par l'intermédiaire de molécules perfluorées fonctionnalisées

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Publication number
EP3829492A1
EP3829492A1 EP19756323.2A EP19756323A EP3829492A1 EP 3829492 A1 EP3829492 A1 EP 3829492A1 EP 19756323 A EP19756323 A EP 19756323A EP 3829492 A1 EP3829492 A1 EP 3829492A1
Authority
EP
European Patent Office
Prior art keywords
perfluorinated
compounds
group
functionalized
groups
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.)
Pending
Application number
EP19756323.2A
Other languages
German (de)
English (en)
Inventor
Konstanze SCHÄFER
Astrid JOHN-MÜLLER
Stefanie KRÄMER
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.)
Technische Universitaet Berlin
Original Assignee
Technische Universitaet Berlin
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 Technische Universitaet Berlin filed Critical Technische Universitaet Berlin
Publication of EP3829492A1 publication Critical patent/EP3829492A1/fr
Pending legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D5/00—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures
    • B05D5/08—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures to obtain an anti-friction or anti-adhesive surface
    • B05D5/083—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures to obtain an anti-friction or anti-adhesive surface involving the use of fluoropolymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/10—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by other chemical means
    • B05D3/102—Pretreatment of metallic substrates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/28—Materials for coating prostheses
    • A61L27/34—Macromolecular materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/08—Materials for coatings
    • A61L31/10—Macromolecular materials
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/10—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by other chemical means
    • B05D3/101—Pretreatment of polymeric substrate
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/10—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by other chemical means
    • B05D3/104—Pretreatment of other substrates
    • 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
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
    • C04B41/009—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone characterised by the material treated
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
    • C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
    • C04B41/4505—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements characterised by the method of application
    • C04B41/455—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements characterised by the method of application the coating or impregnating process including a chemical conversion or reaction
    • C04B41/4556—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements characterised by the method of application the coating or impregnating process including a chemical conversion or reaction coating or impregnating with a product reacting with the substrate, e.g. generating a metal coating by surface reduction of a ceramic substrate
    • 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
    • C04B41/466—Halogenated compounds, e.g. perfluor-compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/12—Chemical modification
    • C08J7/126—Halogenation
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C30/00—Coating with metallic material characterised only by the composition of the metallic material, i.e. not characterised by the coating process
    • C23C30/005—Coating with metallic material characterised only by the composition of the metallic material, i.e. not characterised by the coating process on hard metal substrates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2/00—Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
    • A61F2/02—Prostheses implantable into the body
    • A61F2/30—Joints
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2400/00—Materials characterised by their function or physical properties
    • A61L2400/10—Materials for lubricating medical devices
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2400/00—Materials characterised by their function or physical properties
    • A61L2400/18—Modification of implant surfaces in order to improve biocompatibility, cell growth, fixation of biomolecules, e.g. plasma treatment
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2420/00—Materials or methods for coatings medical devices
    • A61L2420/02—Methods for coating medical devices
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D2201/00—Polymeric substrate or laminate
    • B05D2201/02—Polymeric substrate
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D2202/00—Metallic substrate
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D2203/00—Other substrates
    • B05D2203/30—Other inorganic substrates, e.g. ceramics, silicon
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D2506/00—Halogenated polymers
    • B05D2506/10—Fluorinated polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04—Polyurethanes

Definitions

  • the invention preferably relates to a method for inerting material surfaces, preferably ceramic, metal, glass or plastic surfaces
  • Ceramics and high-performance ceramics and metals generally have relatively high surface energies. Many plastics also have
  • hydrophobic structure relatively low surface energies.
  • all these types of plastic have in common that substances or cells can usually be deposited on the surface.
  • a relatively high surface energy for ceramics, metals or plastics leads to the attachment of cells.
  • the attachment of cells, in particular non-specific cell attachment is to be prevented.
  • the surfaces of the medical products have no or only a very slight interaction with lipophilic or hydrophilic substances, so that there is no cell attachment or substance attachment on the surface.
  • lipophilic or hydrophilic substances for example, in the case of a cardiac machine, it may be on surfaces which are not sufficiently inert for the deposition of coagulation factors and coagulation proteins that lead to the formation of plaque. The detachment of such plaques can
  • WO 2012 / 100100A2 discloses a method in which a coating is applied to a surface, which consists of a polyfluorinated or perfluorinated polymer (e.g. Teflon). This
  • PFCs Perfluorocarbones
  • functional groups that is to say PFCs which generally consist only of C and F
  • This second layer also holds via adhesion, since the PFCs behave very lipophilic in an aqueous environment and attach to the lipophilic structures of the first layer. This creates an inert surface.
  • Non-stick coatings with wear-resistant surfaces are also desirable in the field of tool technology for ceramic and metal surfaces, in particular with high mechanical loads, for example for tableting tools.
  • Teflon is particularly low
  • Teflon coatings A problem with Teflon coatings is, on the one hand, a lack of resistance to higher temperatures (above 260 ° C) and, on the other hand, a lack of resistance to abrasion.
  • Patent WO 2007/025293 shows a method in which perfluoropropyl ether
  • polyurethane surfaces are activated by isocyanate groups or by an alkaline treatment.
  • the fluorine-containing compounds preferably have hydroxyl or cabonyl groups or a
  • Halogen atom In contrast, polyurethane surfaces are not activated in advance in the novel process disclosed here, but instead are subjected to a perfluorination of the surface.
  • Compounds are acid chlorides and sulfonic acid chlorides that are inherently active enough to react with polyurethane surfaces without prior activation.
  • the method disclosed here thus represents a shortening and simplification of the perfluorination of polyurethane surfaces. In the prior art, such good hyperhydrophobic surfaces or structures are not formed in particular on ceramic surfaces.
  • the object of the invention was to provide a method for inerting surfaces - in particular ceramic surfaces - and chemical compounds which eliminates the disadvantages of the prior art.
  • it was the
  • the object of the invention to greatly improve the hydrophobic properties of previous fluorinated surfaces by the additional generation of hyperhydrophobic structures (see FIG. 1).
  • the object of the invention was also to provide a method for inerting ceramic, metal or plastic surfaces and inerted ceramic, metal or plastic surfaces, which are characterized by a low surface energy and high
  • the invention relates to a method for
  • Inerting material surfaces includes the following steps
  • the functionalized perfluorinated compound comprises a perfluorinated compound and a functional group, wherein the
  • perfluorinated compound comprises at most 20 fully fluorinated atoms.
  • the method according to the invention leads to the generation of a hyperhydrophobic structure, above all by the arrangement of the functionalized perfluorinated compounds used on the material surface.
  • a hyperhydrophobic structure above all by the arrangement of the functionalized perfluorinated compounds used on the material surface.
  • particularly good hyperhydrophobic surfaces or structures are obtained, in particular on ceramic surfaces when using perfluorinated compounds which comprise at most 20 completely fluorinated atoms.
  • the inerting of material surfaces is preferably understood to mean a modification of the surfaces, which leads to the fact that the
  • modified surfaces have low adhesion or wettability
  • the described inerting of the material surfaces preferably corresponds to a reduction in the surface energy due to the action of two factors; on the one hand by perfluorination of the surface and on the other hand by building hyperhydrophobic structures similar to those of the lotus effect.
  • perfluorinated compounds For the purpose of inerting, it is preferred that a sufficient areal density of the perfluorinated compounds is achieved so that the material surface is shielded from external molecules by the perfluorinated compounds. In the This is not the case for the connection of perfluorinated compounds to plastics in derivatizations for analysis processes.
  • the material surface is a metal, ceramic or plastic surface. But others can too
  • Material surfaces such as glass surfaces, for example, are rendered inert by means of the methods described, ceramic surfaces are particularly preferred.
  • the method be an immediate covalent
  • Binding between the material surface and the perfluorinated compounds is generated. In other embodiments of the invention, however, it can also be preferred that an intermediate layer is first applied to the material surface, to which the perfluorinated compounds are covalently bound.
  • the intended perfuorated ones are used to mediate a covalent bond
  • a functionalized perfused compound preferably denotes a perfluorinated compound which has at least one functional group.
  • the functional group preferably mediates the covalent bond with atoms of the material surface, preferably the ceramic, metal, plastic or glass surface or an intermediate layer.
  • Coulombic forces between two atomic nuclei or between electrons Is one Difference in electronegativity (electronegativity as a measure of the ability of an atom to attract electrons) between the binding partners (up to approx. 1.5), is preferably referred to as polar bonds. With very high electronegativity differences (from approx. 1, 5) the limit case of a covalent bond comes into play, the ionic bond. This is essentially based on the electrostatic attraction between non-charged ions.
  • the functional groups of the functionalized perfluorinated compounds thus preferably permit addition, substitution, esterification, esterification, condensation or other types of linking reactions in order to produce a covalent compound or an ionic relationship or a metal bond.
  • Preferred functional groups or functionalities are selected from the group comprising haloalkanes, hydroxyl, ether, amino, sulhydryl, aldehyde, keto, carboxyl, ester and acid amide groups, groups with radicals or ions and molecules from the groups of substances Carboxylic acids, peroxycarboxylic acids,
  • Thiocarboxylic acids sulfonic acids, sulfinic acids, sulfenic acids, sulfoxides,
  • Carboxylic acid halides sulfonic acid halides, carboxylic acid amides,
  • Sulfonic acid amides carboxylic acid hydrazides, nitriles, aldehydes, thioaldehydes, ketones, thioketones, oximes, alcohols, phenols, thiols, amines, imines, hydrazines, ethers, esters, thioethers, thioesters, hydrogen halides,
  • Heteroatoms such as Br, I, CI, H, Si, N, O, S, P, hydroxyl, amino, carboxyl groups, haloalkanes, carboxamides, alcohols, hydrazines, isocyanates, thiocyanates and acid amides are particularly preferred.
  • the functional groups are preferably nucleophilic leaving groups which permit nucleophilic substitution.
  • nucleophilic substitution means the exchange of a group or an atom (hereinafter referred to as a leaving group) by a new group or a new atom.
  • the leaving group should have a lower nucleophilicity than the attacking nucleophile.
  • nucleophile means a molecule that either carries a negative charge (electron pair donor) or partial charge or that meets the classic concept of a Lewis base. For the determination of the nucleophilicity the
  • Electronegativity and the resulting dipole or monopoly The greater the electronegativity, the stronger the nucleophile.
  • nucleophilic substitution the nucleophile attacks the organic chemical molecule on the carbon atom on which the leaving group is also located. Two types of reactions are used here, nucleophilic substitution 1.
  • R alkyl
  • the functionalized are perfluorinated
  • the functionalized are perfluorinated
  • the method is thus characterized in that the functionalized perfluorinated compounds are one
  • perfluorinated compound with at least one functional group which comprises at least one double bond and can be attached by UV crosslinking
  • Plasma or corona treatment of the material surface arise and / or is a perfluorinated compound with at least one functional group which is suitable for the cycloaddition.
  • the functionalized perfluorinated compound is a perfluorinated compound with at least one functional group, the functional group preferably being a nucleophilic leaving group, particularly preferably selected from a group comprising Br, I, CI, H, N, O, S, P , Hydroxyl, amino, carboxyl groups, carboxylic acids, thiocarboxylic acids, sulfonic acids,
  • Sulfinic acids carboxylic acid halides, sulfonic acid halides, acid amides, carboxylic acid amides, alcohols, sulfonic acid amides,, phenols, hydrazines, thiols, amines, imines, hydrazines, isocyanates, thiocyanates, isothiocyanates.
  • the functionalized perfluorinated compounds preferably comprise one
  • the perfluorinated compounds are preferably linear or branched acyclic or cyclic, polycyclic or
  • the functionalized perfluorinated compounds are functionalized perfluorocarbons (PFC).
  • Molecules selected from the group of the perfluorocarbones preferably denote linear or branched acyclic or cyclic, polycyclic or heterocyclic aliphatic alkanes, alkenes, alkynes, aromatic compounds or
  • Combinations of these compounds can be in which all H atoms are replaced by F atoms which optionally additionally have at least one non-fluorinated or partially fluorinated substituent in the form of one or more functional groups, aliphatic chains or heteroatoms, in particular Br, I, CI, H, Si, N, O, S, P, or these are in connection with one or more other functional groups.
  • the perfluorocarbones are selected from the group comprising C1-C100, preferably C1-C50, particularly preferably C1-C30, very preferably CI-C20, most preferably C1-C20 alkanes, alkenes or alkynes linear, branched, cyclic, polycyclic or heterocyclic, C6-C50, preferably O Q -C30, particularly preferably C1-C20 aromatic or heteroaromatic systems can also be preferred.
  • the C atoms are preferably largely, most preferably completely, perfluorinated.
  • the functionalized perfluorocarbones comprise between 1 and 50, preferably between 1 and 20, particularly preferably between 1 and 10, very particularly preferably between 2 and 10 perfluorinated carbon atoms.
  • Functionalized perfluorinated compound a perfluorinated compound and a functional group, the perfluorinated compound comprising at most 20, most preferably at most 10, fully fluorinated atoms.
  • These preferred functionalized perfluorinated compounds lead to particularly good results (e.g. hyperhydrophobic structures, in particular hyperhydrophobic properties of the surfaces). If you wet a solid surface with a liquid, you can measure the contact angle between the solid and liquid phase. The higher the
  • the contact angle the more hydrophobic (water-repellent) the surface. If the contact angle is less than 90 degrees, the material is hydrophilic, i.e. water-attracting. Such material surfaces are wetted by the water. If the contact angle is between 90 and 160 degrees, one speaks of a hydrophobic material. It is water repellent; Water droplets roll off the surface, taking dirt particles with them. So the surface is washed clean by itself. Is the
  • the functionalized perfluorinated compound comprises a perfluorinated compound and a functional group, the perfluorinated compound comprising at most 20, very particularly preferably at most 10, completely fluorinated atoms, the hyperhydrophobic properties are particularly of
  • These perfluorinated compounds are preferably also referred to as short-chain molecular residues.
  • the functionalized perfluorinated molecules are based on one of the following substances:
  • Metal organyls e.g. lithium organyl are also particularly preferred.
  • Carbon atom compounds wherein at least one carbon atom is attached to a metal
  • the modifications are biocompatible and can be used medically, since similar molecules are already used in medical applications for other functions, for example as contrast agents or as
  • R perfluorocarbon residue or aliphatic chain
  • the perfluorinated part or molecular residue comes from the group of perfluorosilicon compounds containing linear or branched acyclic or cyclic, polycyclic or heterocyclic aliphatic silanes, in which all H atoms are replaced by F atoms, which optionally additionally contain non-fluorinated or partially fluorinated substituents with one or more functional groups or heteroatoms, in particular Br, I, CI, H, Al, N, O, S, P or these in combination with one or more other functional groups.
  • Perfluorosilicon compounds from the group comprising Sh-Shoo, preferably Si-i-Siso, particularly preferably Sii-Si3o, very preferably Sh-S o, most preferably Sh-S o perfluorinated silicon compounds are used.
  • perfluorosilicon compounds are also functionalized with suitable substituents. That the functionalized
  • Perfluorosilicon compounds have a perfluorinated part or molecular residue, as described above, and additionally at least one functional group for mediating a covalent bond.
  • Perfluorosilicon compounds between 1 and 50, preferably between 1 and 20, particularly preferably between 1 and 10, very particularly preferably 2 and 10 perfluorinated Si atoms.
  • the Si atoms of the molecular residue, ie the component without a functional group, are preferably completely fluorinated.
  • Silicon tetrahalides Silicon tetrahalides, silicones, silicone oils, zeolites, zirconium silicates.
  • the perfluorinated compound is selected from the group of further perfluorinated compounds, it being based on compounds selected from NF3, N2F4, SNF3, CF3SN, SF4, SF6, perfluorinated nitrogen-sulfur compounds.
  • the perfluorinated part of the molecule consists of fluorine-phosphorus compounds or fluorine-aluminum compounds.
  • the perfluorinated compound is characterized by short-chain molecules.
  • the functionalized perfluorinated compounds comprise between 1 and 50, preferably between 1 and 20, particularly preferably between 1 and 10, very particularly preferably 2 and 10 perfluorinated atoms, the atoms preferably also being selected from the group C, Si, S or N or combinations of these, such as SN (nitrogen-sulfur).
  • the atoms of the constituent of the perfluorinated compound are preferably without
  • the perfluorinated compound contain two or more perfluorinated molecules selected from the group of perfluorocarbones (PFC), perfluorosilicon compounds and other perfluorinated compounds.
  • PFC perfluorocarbones
  • the functionalized perfluorinated compounds described above can be combined into several units. The following molecules are mentioned as examples:
  • These molecules can be linked to the other molecules contained in the compound according to the invention via Nh groups or OH groups or other suitable groups.
  • a large number of different ceramic surfaces can advantageously be rendered inert by the functionalized perfluorinated compounds disclosed.
  • ceramic comprises ceramic materials which are inorganic, non-metallic and polycrystalline.
  • the ceramic can, for example, be selected from a group comprising aluminum oxide, zirconium oxide, aluminum titanate, silicon carbide, silicon nitride or aluminum nitride or other non-metallic or metallic substances or
  • High-performance ceramics or technical ceramics which have been optimized for technical applications are particularly preferred.
  • they can have special hardnesses, conductivities or temperature behavior etc. in order to meet the respective requirements for the desired application.
  • Materials for high-performance ceramics such as made of aluminum oxide, zirconium oxide, aluminum titanate, silicon carbide, silicon nitride or aluminum nitride or other non-metallic or metallic substances or dispersion ceramics and
  • the ceramic surface is formed by a ceramic is selected from a group comprising aluminum oxide, zirconium oxide, aluminum titanate, silicon carbide, silicon nitride or aluminum nitride or other non-metallic or metallic substances or dispersion ceramics and piezoceramics, porcelain, stoneware, stealite, glass ceramic, Cordlerite, titanium oxide, yttrium oxide, beryllium oxide, magnesium oxide, uranium oxide, titanates.
  • Preferred ceramic compounds include, for example, following particles MgO, Zr02, B4C, S3C, Si3N4, BN, AI2Ti05, Pb (Zr, Ti) 02, BaTi03, AIN or AI203.
  • Various functionalized metal surfaces can also advantageously be rendered inert by the functionalized perfluorinated compounds disclosed.
  • the metal surface is formed by a metal selected from a group comprising titanium, aluminum, cadmium, chromium, iron, gold, iridium, cobalt, copper, nickel, palladium, platinum, silver, zinc and tin and alloys which these contain such as titanium alloys or stainless steel, very particularly preferably the metal surface is formed by titanium or a titanium alloy.
  • the preferred metals, especially titanium, can be used with the
  • the metals can be used in a variety of ways. Especially for medical Applications, for example for implants with metal components, can be ensured by the covalent connection of the functionalized perfluorinated compounds that undesired deposits of biological material or cells do not occur.
  • Plastic formed selected from a group containing polyacetals, polyacrylates, polyamides, polyaryls, celluloses, polyesters, polyoleofins, polystyrenes, polyvinyacatates, polyvinyl chlorides, polyether ketones, polyaryl ether ketones, polylactides, amino resins, epoxy resins, polyether alcohols, butadiene elastomers, isopolymer elastomers, fluorocarbon elastomers, fluorocarbon elastomers Silicone elastomers, pentene elastomers, sulfide elastomers, urethane elastomers and vinyl chloride elastomers.
  • Perfluorinated compounds can be implemented in various ways.
  • the ceramic or metal surfaces can be preactivated by acids (e.g. with sulfuric acid or hydrofluoric acid), by other agents
  • a direct reaction with functionalized perfluorinated compounds without preactivation can also be provided.
  • the ceramic or metal surfaces are coated with an intermediate layer with which the functionalized perfluorinated compounds react.
  • the material surface is activated before the reaction of the functionalized perfluorinated compounds, the activation preferably using acid, laser, corona, ozone or
  • Plasma treatment takes place.
  • acids for this purpose, particularly preferably a hydrogen fluoride (hydrofluoric acid) or a sulfuric acid.
  • acids for this purpose, particularly preferably a hydrogen fluoride (hydrofluoric acid) or a sulfuric acid.
  • other activations for example by means of plasma or laser radiation, are also conceivable.
  • different activation takes place for partial areas of the material surface. In this way, different degrees of inertization can be realized in a controlled manner on the material surface.
  • a selective surface treatment i.e. a different activation of the sub-areas e.g. a defined pattern between regions of different can advantageously be achieved by laser treatment or by a selectively generated printed image and the associated accessibility or inaccessibility for the reactions with the functionalized perfluorinated compounds
  • Properties e.g. high and very low surface energy are generated.
  • different activation takes place for partial areas of the material surfaces according to a predetermined pattern, so that different inerting of the ceramic or metal surface is realized according to the predetermined pattern.
  • the invention relates to inertized
  • the perfluorinated compounds being covalently bonded to a ceramic or metal surface.
  • the invention relates to inertized
  • Material surfaces preferably ceramic, metal or plastic surfaces can be produced or produced by a method according to the invention or preferred
  • perfluorinated compounds are covalently bound to a material surface, preferably a ceramic, metal or plastic surface.
  • Inerted material surfaces preferably inertized ceramic, metal or
  • plastic surfaces preferably means a material surface which, through inerting, has low adhesion or wettability
  • the inertized material surface preferably the inertized ceramic, metal or plastic surface can also be referred to as an inert ceramic, metal or plastic surface.
  • the inertized material surfaces are characterized by the advantages described.
  • the inertized material surfaces are characterized by extremely low surface energies, which makes them highly chemical
  • Substances or cells are effectively prevented, so that they are particularly suitable for medical applications.
  • the perfluorinated compounds can be connected to the surface of the material, preferably the metal, ceramic or plastic, for example from a group, by a linker or spacer molecule containing in particular haloalkanes, hydroxyl, ether, amino, sulhydryl, aldehyde, keto, carboxyl, ester and acid amide groups, groups with radicals or ions and molecules from the groups of substances
  • Preferred linker molecules are based on hydroxyl or amino groups
  • Disulfide bridges are very particularly preferred.
  • the inertized material surface is characterized in that the covalent bond is carried out by a linker or spacer molecule, the linker or spacer molecule preferably being on hydroxyl or
  • Carboxamides compounds with multiple bonds, carbamates, disulfide bridges and hydrazides, haloalkanes, sulhydryl, aldehyde, keto, carboxyl, ester and acid amide groups, thiols, amines, imines, hydrazines, or disulfide groups, glycerol, succinylglycerol, orthoesters and vinyl ether, phosphoric acid ester is based, with ester and ether groups and disulfide bridges being very particularly preferred.
  • Functional molecules are used that generate electrical conductivity, for example, or that promote cell growth. Other examples are those
  • FGF fibroblast growth factor
  • VEGF vascular endothelial growth factor
  • NGF Nerve Growth Factor
  • the invention relates to the use of a material surface rendered inert using the described methods, preferably a ceramic, metal or plastic surface in a medical product, preferably in an implant in which cell attachment is wholly or partially undesirable, particularly preferably in one Heart implant, a stent, a prosthesis, a joint, in dental implants or in a medical device through which
  • Substances especially blood or blood components, are conducted.
  • Material surfaces preferably the ceramic, metal or plastic surfaces, are characterized by a particularly high level of biocompatibility and have an extremely low risk of complications.
  • an implant preferably denotes a medical one
  • a dental implant preferably denotes an implant for the mouth or jaw area and can preferably both replace tooth structures and support them.
  • a heart implant is preferably understood to mean a device which mimics the function of the human heart, for example to bridge the time that a patient has to wait for a donor heart.
  • the medical products are characterized by particularly low deposits and can therefore be worn in the body for long periods of time without deposits or wear leading to complications.
  • the invention relates to the use of the inertized material surfaces, preferably the ceramic or metal surfaces, in a product of electrical engineering, in particular microelectronics.
  • the inertized material surfaces preferably the ceramic or metal surfaces
  • Metal surfaces can be effectively avoided.
  • the methods described, in particular using short-chain perfluorinated compounds, advantageously also ensure that the desired electrical properties of the ceramic or metal surfaces do not change as a result of the inerting. It is known that above perfluorinated interfaces the otherwise existing electrical field of a material is comparatively very small. This cannot develop an electrostatic attraction.
  • the invention relates to the use of the inertized material surfaces in window glasses, furnishings, sanitary facilities or buildings.
  • the method described can advantageously also be used for inerting glass surfaces or ceramics, which are typically used in window glasses, furnishings, sanitary facilities or buildings.
  • Material surfaces which have been rendered inert in the above-mentioned applications are distinguished by the fact that there is little or no surface
  • Hyperhydrophobic surfaces are perfluorinated surfaces that have additional lotus-like structures due to the orderly linked perfluorinated molecular chains. In contrast to Teflon surfaces with only a few fluorine atoms pointing away from the surface, the effectiveness of
  • Hyperhydrophobic surfaces extremely reinforced. Perfluorinated surfaces with attached irregular perfluorinated chains are unable to build ordered hyperhydrophobic structures.
  • Hydrofluoric acid by other agents, by laser treatment, by corona, ozone or plasma treatment or other processes and subsequent reaction with functionalized perfluorinated compounds
  • a defined pattern between areas of different properties e.g. high and very low surface energy
  • hydrofluoric acid hydrofluoric acid
  • sulfuric acid concentrated sulfuric acid
  • Oxygen atoms are split off as water (see reaction equation 1).
  • the zirconium atom By splitting off the oxygen, the zirconium atom can exist as a tetravalent ion (Zr 4 ) and form an ionic compound with the fluoride ions (salt). This removes the zirconium ion from the surface structure of the ceramic and "rinses it out”.
  • the activated first protonated state of the ceramic can attack the positively perfluorinated methyl iodide carbon nucleophilically, so that a perfluorinated methyl group is added.
  • the perfluorinated "ether" formed is more difficult for body cells to cleave than a non-perfluorinated methyl group, since the fluorine atoms contained are bad due to their low relative atomic mass, high electronegativity and their small radius (ionic radius)
  • methyl groups with their hydrogen atoms can form both van der Waals interactions and hydrogen bonds, which is significantly more difficult with the perfluorinated residues.
  • the ionically activated intermediate can also be used as an electrophilic reactant.
  • the zirconium ion is attacked nucleophilically by the perfluorinated alcohol. With the elimination of hydrofluoric acid (which can re-enter the reaction process for further surface activation), the perfluorinated “Diether” is formed.
  • reaction equation 4 also shows one
  • Reactant is used.
  • a primary amine is used as the nucleophilic reaction partner.
  • Perfluorinated secondary amines can also fulfill this type of reaction.
  • the amine attacks and binds to the positively charged zirconium by means of a lone pair of electrons from nitrogen.
  • a proton (H + ) is split off and forms HF with the fluoride ion, which is again available for surface activation.
  • the reaction type corresponds to a condensation in which water is split off as a by-product (see reaction equation 5 & 6).
  • the silane oxygen nucleophilically attacks the positively polarized zirconium.
  • An H + and an OH group are split off as water.
  • silanes or other semimetals or metals are used to increase the electrical conductivity.
  • Zirconium (IV) oxide can electrolytically transport oxygen ions at high temperatures. This creates an electrical voltage. The doping will improve the electrical conductivity.
  • Zirconium (IV) oxide surface reduces or prevents conduction of the electrical current.
  • this insulator effect enables precise manufacture of control systems for conducting the electrical current.
  • Reaction equation 7 addition and hydrogenation of tetrafluoroethene on the activated ceramic surface
  • Reaction equation 7 shows an analog to the first step of the Ziegler direct method.
  • the tetrafluoroethylene is additively added to the activated zirconium oxide surface and hydrogenated.
  • Reaction equation 8 reaction of a perfluorinated metal organyl with the activated ceramic surface
  • the reaction equation 8 shows the reaction of a perfluorinated metal organyl
  • LiF lithium fluoride
  • Reaction equation 9 reaction of the activated non-ionic state of the
  • reaction already described in reaction equation 8 can also be carried out with the non-ionic intermediate state of the activated zirconium oxide surface.
  • a further activation is achieved by the metalation of the surface oxygen, two perfluorinated organyl residues already clinging to the
  • the aluminum oxide used in a corundum structure is also suitable for these reactions.
  • Reaction equation 10 reaction of the alumina ceramic with hydrofluoric acid
  • the oxygen of the surface structure of the ceramic is protonated by the hydrofluoric acid, so that AI (OH) 3 and AIF3 are formed as an intermediate. Water is split off by further protonation of the OH groups and the more reactive AIF 3 is formed .
  • Reaction equation 1 1 Reaction of the activated ceramic surface with a perfluorinated haloalkyl
  • the oxygen of the AI (OH) 3 nucleophilically attacks the positively polarized carbon atom of trifluoroiodomethane.
  • Iodine is formed as iodide and forms the by-product hydrogen iodide (HI) with the proton of the OH group.
  • Reaction equation 12 reaction of the activated ceramic surface with a
  • the alcohol oxygen of the perfluorinated alcohol nucleophilically attacks the aluminum.
  • An OH group is split off as OH and the alcohol proton (H + ), which form water as a by-product.
  • silane oxygen nucleophilically attacks the aluminum and it becomes OH and that
  • Proton of the silane OH group is split off, so that water forms as a by-product.
  • AI (OH) 3 HO-Si ((CF 2 ) 2 9 -CF 3 ) 3 - ⁇ AI (OH) 2 OSi ((CF 2 ) 2 , -CF 3 ) 3
  • Reaction equation 14 Linking a perfluorinated silane to the activated one
  • the lithium organyl shown in reaction equation 15 is strongly polarized.
  • the negatively polarized organyl carbon atom nucleophilically attacks the aluminum. It will be OH
  • Titanium (IV) oxide (T1O2) is another high performance ceramic that is characterized by the above
  • the oxygen atoms of the Ti0 2 surface are protonated by HF until the more reactive TiF 4 is formed.
  • Reaction equation 17 nucleophilic substitution on the activated ceramic surface
  • reaction equation 17 The trifluoroiodomethane shown in reaction equation 17 is polarized, so that a
  • Oxygen of the activated ceramic surface attacks the positively polarized carbon atom of trifluoroiodomethane nucleophilically and iodide is split off. This accumulates with the proton split off to hydrogen iodide (Hl) as a by-product.
  • Hl hydrogen iodide
  • Electrophilic and as such is attacked nucleophilically by the oxygen of the perfluorinated alcohol.
  • the proton (H + ) of the alcohol group is split off, which assembles with a fluoride ion to form HF as a by-product, which is used for further
  • Reaction equation 19 activated ceramic surface as electrophile
  • the perfluorinated primary amine acts as a nucleophile.
  • the amine nitrogen nucleophilically attacks the positive titanium.
  • An H + of the amino group is split off, which together with an F forms the by-product HF.
  • reaction equation 20 the silane oxygen nucleophilically attacks the titanium on the ceramic surface. OH is split off, which forms as a by-product with H + water.
  • reaction equation 21 Linking a perfluorinated silane to the activated ceramic surface
  • reaction equation 21 the silane oxygen nucleophilically attacks the titanium on the ceramic surface. OH is split off, which forms as a by-product with H + water.
  • Reaction equation 22 addition and hydrogenation of tetrafluoroethene on the activated ceramic surface
  • Reaction equation 23 reaction of a perfluorinated metal organyl with the activated ceramic surface
  • the lithium organyl shown in reaction equation 23 is strongly polarized.
  • the negatively polarized organyl carbon atom attacks the titanium nucleophilically.
  • OH is split off, which forms as a by-product with Li + LiOH.
  • Reaction Equation 24 Reaction of the activated non-ionic state of the
  • reaction equation 24 shows a nucleophilic attachment of the negatively polarized organyl to the titanium. Li + also binds to the oxygen atoms on the ceramic surface, so that a reactive species is created.
  • a coating with accessible functional groups can alternatively be applied (cf. examples 1 and 3 of the exemplary inerting routes of plastic surfaces by means of functionalized perfluorinated compounds)
  • the ceramic may be coated with a polyurethane compound which contains OH groups and bonds well to the surface of the ceramic.
  • a reaction with functionalized perfluorinated compounds can then be brought about via the OH groups, in which case a perfluorinated compound with an isocyanate group is used.
  • the ceramic is coated with a polymer compound that contains NH2 groups and bonds well to the surface of the ceramic.
  • a reaction with functionalized perfluorinated compounds is then brought about via the NH2 groups, in which case a perfluorinated compound with aldehyde group is used.
  • the ceramic is coated with a polymer compound that enables an azide-alkyne cycloaddition.
  • This polymer compound contains azide groups, via which the functionalized perfluorinated compounds are bound by means of an alkyne group.
  • Other variants of click chemistry can also be used.
  • the inerting of plastic surfaces can be implemented in different ways:
  • Examples of basic connection options for functionalized perfluorinated compounds on functional groups of a plastic surface or a coating include:
  • R or R ' functionalized perfluorinated compound
  • Another possibility is the crosslinking of functionalized perfluorinated compounds with double bonds (e.g. perfluorinated sulfonic acids or perfluorinated carboxylic acids or perfluorinated monomers of plastics such as acrylates) with plastics which also contain double bonds (e.g. polyester) under UVA radiation.
  • perfluorinated compounds are preferably suitable, on whose functional group a nucleophilic attack can be undertaken or positively charged perfluorinated ions.
  • Other chemical compounds are also possible.
  • the molecules shown would be biodegradable. After connection to the plastic, the protruding perfluorinated chains shield the connection of degrading enzymes.
  • the plastic is coated with a polyurethane compound that contains OH groups.
  • a reaction with functionalized perfluorinated compounds is then brought about via the OH groups, as exemplified above under 1) / 3).
  • the plastic is coated with a polyacrylamide compound that contains NH2 groups.
  • a reaction with functionalized perfluorinated compounds is then brought about via the NH2 groups, as exemplified above under 1) / 3).
  • the plastic is coated with a layer that enables an azide-alkyne cycloaddition.
  • This polymer compound contains azide groups, via which the functionalized perfluorinated compounds are bound by means of an alkyne group.
  • Other variants of click chemistry can also be used.
  • Polyurethane plates were wetted with nonafluoro-1-butanesulfonyl chloride (Sigma Aldrich, Art. No. 51974-1 G-F) and incubated in a closed container for 30 min at room temperature. The plates were then in
  • the glass surface was then wetted with perfluorobutyryl chloride (Sigma Aldrich, Art. No. 257923-5G) and incubated in a closed container for 30 min at room temperature. Then the glass support in
  • An uncoated titanium support was surface-activated in an HF bath for 30 s and then washed in isopropanol and in distilled water and dried.
  • the titanium surface was then wetted with perfluorobutyryl chloride (Sigma Aldrich, Art. No. 257923-5G) and incubated in a closed container for 30 min at room temperature.
  • the titanium support was then washed in isopropanol and with distilled water and dried.
  • the steel surface was then wetted with perfluorobutyryl chloride (Sigma Aldrich, Art. No. 257923-5G) and incubated in a closed container for 30 min at room temperature.
  • the titanium support was then washed in isopropanol and with distilled water and dried.
  • a ceramic plate was surface-activated in an HF bath for 30 s and then washed in isopropanol and in distilled water and dried.
  • the ceramic surface was then wetted with perfluorobutyryl chloride (Sigma Aldrich, Art. No. 257923-5G) and incubated in a closed container for 30 min at room temperature.
  • the ceramic plate was then washed in isopropanol and with distilled water and dried.

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Abstract

La présente invention concerne un procédé d'inertage de surfaces de matériau, de préférence, de surfaces de céramique, métal ou plastique à l'aide de composés perfluorés fonctionnalisés aux fins de formation de structures hyperhydrophobes. Les surfaces inertes, ainsi fabriquées ou aptes à être fabriquées, possèdent une énergie superficielle extrêmement faible, sont résistantes à tout dépôt de substances ou de cellules et possèdent un très faible coefficient de frottement. L'invention concerne également des possibilités d'application pratiques des surfaces inertes.
EP19756323.2A 2018-07-30 2019-07-30 Inertage de surfaces de matériau par l'intermédiaire de molécules perfluorées fonctionnalisées Pending EP3829492A1 (fr)

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WO2007025293A2 (fr) * 2005-08-26 2007-03-01 The University Of North Carolina At Chapel Hill Utilisation de derives d'acides de fluoropolymeres pour surfaces resistant aux salissures
US20070172666A1 (en) * 2006-01-24 2007-07-26 Denes Ferencz S RF plasma-enhanced deposition of fluorinated films
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US9932484B2 (en) 2011-01-19 2018-04-03 President And Fellows Of Harvard College Slippery liquid-infused porous surfaces and biological applications thereof
US20130280485A1 (en) * 2012-04-19 2013-10-24 Massachusetts Institute Of Technology Superhydrophobic and Oleophobic Functional Coatings Comprised of Grafted Crystalline Polymers Comprising Perfluoroalkyl Moieties
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Ipc: A61F 2/30 19850101AFI20230112BHEP