EP3192853A1 - Oberflächenbehandlungsverfahren zum erzeugen einer oleophoben und/oder hydrophoben beschichtung - Google Patents

Oberflächenbehandlungsverfahren zum erzeugen einer oleophoben und/oder hydrophoben beschichtung Download PDF

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Publication number
EP3192853A1
EP3192853A1 EP16305039.6A EP16305039A EP3192853A1 EP 3192853 A1 EP3192853 A1 EP 3192853A1 EP 16305039 A EP16305039 A EP 16305039A EP 3192853 A1 EP3192853 A1 EP 3192853A1
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Prior art keywords
group
general formula
hydrophobic
epilame
different
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EP16305039.6A
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English (en)
French (fr)
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EP3192853B1 (de
Inventor
Franck Martin
Guillaume GRACY
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SIKEMIA
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Sikemia
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/72—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing sulfur, selenium or tellurium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/14—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by electrical means
    • B05D3/141—Plasma treatment
    • B05D3/142—Pretreatment
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D5/00—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures
    • B05D5/08—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures to obtain an anti-friction or anti-adhesive surface
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/74—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing phosphorus
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/76—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing silicon
    • 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
    • C23C22/00—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals
    • C23C22/02—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals using non-aqueous solutions
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D1/00—Processes for applying liquids or other fluent materials
    • B05D1/18—Processes for applying liquids or other fluent materials performed by dipping
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/081—Thiols; Sulfides; Polysulfides; Mercaptals used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/023—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/0405—Phosphate esters used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/049—Phosphite
    • C10M2223/0495—Phosphite used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/0603—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/04—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having a silicon-to-carbon bond, e.g. organo-silanes
    • C10M2227/045—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having a silicon-to-carbon bond, e.g. organo-silanes used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/06—Instruments or other precision apparatus, e.g. damping fluids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/015—Dispersions of solid lubricants
    • C10N2050/02—Dispersions of solid lubricants dissolved or suspended in a carrier which subsequently evaporates to leave a lubricant coating
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2080/00—Special pretreatment of the material to be lubricated, e.g. phosphatising or chromatising of a metal

Definitions

  • the present invention relates to a method for treating a surface selected from the group consisting of sapphire, brass, rhodium-plated brass, gold-plated brass, nickel, steel, hardenable steel, iron, aluminum, titanium, lead, silver, gold, chromium, copper, manganese, vanadium, lithium, cobalt, silicon and various alloys and metal oxides thereof metals, said surface treatment method comprising a step of applying, on said surface, hydrophobic and / or oleophobic molecules and / or application of an epilame.
  • the document US2014 / 087197 relates to the application of a hydrophobic and / or oleophobic molecular layer so as to constitute an anti-fingerprint coating and the document EP2865737 relates to the production of an epilamate consisting in covering a surface of an epilame (also called coupling agent), that is to say to cover a surface of a product or a substance making it possible to avoid a liquid, for example a lubricant, does not spread but on the contrary it remains localized at a precise location.
  • the application of an epilame reduces the surface energy of an article and modifies the surface tension by applying a hydrophobic and / or oleophobic molecular layer.
  • the so-called “chemical” epilams (which are distinguished from so-called “mechanical” epilams) comprise two parts, namely (1) the anchor (or hook) which determines the attachment of the epilame to a surface and (2) ) the functional body which confers the epilame properties on the molecule, especially via fluorinated groups.
  • the document EP2865737 relates to an establishment of a tie layer on a surface, this tie layer being provided so that an epilame subsequently applied adheres more strongly to the surface comprising the tie layer.
  • the tie layer according to this prior document thus constitutes an intermediate layer between the surface to be treated and the epilame itself.
  • such a tie layer can be applied according to a vacuum evaporation technique, a flash evaporation technique or by an atomic layer deposition technique.
  • the document US2014 / 087197 whose purpose is to apply a hydrophobic and / or oleophobic molecular layer so as to constitute an anti-bump coating on a surface, proposes an intermediate coating of this surface with a transition layer intended for provide improved adhesion of the hydrophobic and / or oleophobic molecular layer.
  • the transition layer according to this prior document is therefore an intermediate layer between the surface to be treated and the hydrophobic and / or oleophobic molecules.
  • the present invention aims to overcome the drawbacks of the state of the art by providing a method minimizing the number of manufacturing process steps and optimizing the adhesion (attachment) of epilams and / or hydrophobic molecules and and / or oleophobic on a pretreated surface so that the epilame anchors and / or the hydrophobic and / or oleophobic molecules bind strongly and durably to the pretreated surface, thus allowing for high resistance of the coupling agents (epilam) and / or or hydrophobic and / or oleophobic molecules at successive washing cycles.
  • the coupling agents epilam
  • a method of treating a surface as indicated at the beginning characterized in that it comprises a pretreatment step by a plasma process of said surface before said step d application of hydrophobic and / or oleophobic molecules and / or application of an epilame.
  • plasma pretreatment of said surface makes it possible to create attachment sites directly at the latter so that subsequent treatment with a coupling agent (epilame) and / or hydrophobic and / or oleophobic molecules of this same surface then having attachment sites is optimized. More particularly, it has been shown that pretreatment by a plasma method with creation of hooks on the surface to be treated subsequently allows a coupling agent (epilame) and / or hydrophobic and / or oleophobic molecules. adhere more strongly and resist better to successive washing cycles.
  • a coupling agent epilame
  • a plasma treatment for example by oxygen plasma or by nitrogen plasma makes it possible to provide the surface, during a pretreatment stage, with adequate attachment sites of the -OH type or - NH 2 , these attachment sites to ensure a better adhesion of epilams and / or hydrophobic molecules and / or oleophobes applied thereafter.
  • the sites of hooks formed by plasma treatment are nucleophilic sites promoting the anchoring of epilame anchors but also hydrophobic and / or oleophobic molecules.
  • each R 1 independent of each other, and identical or different from each other at each occurrence, are selected from the group consisting of (CR 5 R 6 ) n , where each R 5 and R 6 , which are identical to or different from each other, are independently selected from the group consisting of H, a linear or branched alkyl group having from 1 to 8 carbon atoms, which is optionally substituted by at least one atom of the halogen family, an aryl group or an aralkyl group, n being from 1 to 30.
  • each R 1 independent of one another, and identical or different from each other at each occurrence, are (CH 2 ) n and n is between 1 and 30.
  • each R ' independent of one another, and identical or different from each other at each occurrence, are selected from the group consisting of a bond, (CR 5 R 6 ) n , where each R 5 and R 6 , identical to or different from each other, are independently selected from the group consisting of H, a linear or branched alkyl group having 1 to 8 carbon atoms, which is optionally substituted with at least one atom of the halogen family, an aryl group or an aralkyl group, n being between 1 and 30.
  • each R ' independent of each other, and identical or different from each other at each occurrence, are a bond, (CH 2 ) n and n is between 2 and 12, preferably each R 'is a bond.
  • repeating alkylene oxide units may be mentioned (O-CH 2 -CH 2 -O) m , (O-CH 2 -CH 2 -CH 2 O) m , (OCH 2 -CH (CH 3 )) m and (O-CH (CH 3 ) -CH 2 ) m , where m is between 1 and 100, preferably m is between 2 and 30, preferentially, m is between 3 and 10.
  • perfluoroalkyl groups comprising from 1 to 50 carbon atoms
  • the following compounds may be mentioned: perfluoropropyl, perfluorobutyl, perfluoropentyl, perfluorohexyl, perfluorooctyl, perfluorononyl and perfluorodecyl and the like.
  • the perfluoroalkyl group comprises 3 to 25 carbon atoms, preferably 4 to 20 carbon atoms, more preferably 6 to 12 carbon atoms.
  • the method for treating a surface according to the invention comprises a preliminary step of dissolving in a solvent said hydrophobic and / or oleophobic molecules and / or said epilam, for example monomer of general formula (I) and or dimer of general formula (II) to form a surface treatment solution.
  • said preliminary step of dissolving in a solvent to form a surface treatment solution is carried out by dissolving in a solvent selected from the group consisting of isopropanol, ethanol and methanol. , dimethylformamide, acetone, tetrahydrofuran, preferably isopropanol.
  • said preliminary step of dissolving in a solvent forms a surface treatment solution comprising said hydrophobic and / or oleophobic molecules and / or said epilam, for example said monomer of general formula (I) and / or said dimer of general formula (II), in a proportion of 0.01% to 10% v / v in a solvent, preferably in a proportion of 0.1% to 5% v / v.
  • said step of bringing said pretreated surface into contact with said hydrophobic and / or oleophobic molecules and / or with said epilame, for example with said monomer of general formula (I) and / or with said dimer of general formula (II), is carried out by spraying, dipping, spraying, buffering, wiping, spin coating and deep coating.
  • the present invention also relates to an article (or a product), in particular an article (or a product) for watches, automobiles, microelectronics, optics, aeronautics, nautical, medical field, packing or construction, having at least a portion of surface treated according to the method according to the invention.
  • the present invention also relates to a use of hydrophobic and / or oleophobic molecules and / or an epilame, for example a monomer of general formula (I) and / or a dimer of general formula (II) in a surface treatment, in particular for treating a surface of a timepiece, automobile, microelectronics, optics, aeronautics, nautical, medical field, packing or construction.
  • Other embodiments of the use of hydrophobic and / or oleophobic molecules and / or an epilame, for example a monomer of general formula (I) and / or a dimer of general formula (II), according to the invention are indicated in the appended claims.
  • Step 2 starting from 10,11-bis (2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9 heptadecafluorononyl) icosane-1, 20-diol (formula A)
  • 10,11-bis (9-bromononyl) -1,1,1,2,2,3,3,4,4,5,5, 6,6,7,7,8,8 is obtained , 13,13,14,14, 15,15,16,16,17,17,18,18,19,19,20,20,20 tetracyclafluoroicosane.
  • Step 4 starting from tetraethyl 10,11-bis (2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptadecafluorononyl) -icosane -1,20-diylbisphosphonate (formula C)
  • This process for synthesizing a compound of general formula (I) according to the invention is therefore based on a substitution of at least one halogenated group of a starting molecule.
  • Step 4 starting from tetraethyl 10,11-bis (2,2,3,3,4,4,5,5,5-nonafluoropentyl) icosane-1,20-diylbisphosphonate (formula G)
  • This process for synthesizing a compound of general formula (I) according to the invention is therefore also based on a substitution of at least one halogenated group of a starting molecule.
  • pretreatment with an oxygen plasma was carried out on the surfaces to be treated with the PICO LF PCCE apparatus for 4 minutes at a power of 100 W.
  • the pretreated surfaces were treated by immersion for 5 minutes or 15 minutes in epilamization solutions containing a monomer of general formula (I) and / or a dimer of general formula (II) in a proportion of 2.5 ⁇ 10 -3 moIL -1 in isopropanol as solvent. Then, the treated substrates were drained for 1 minute and then dried under hot air (55 ° C) for 5 minutes.
  • the contact angle measurement reports the ability of a liquid (eg, an oil) to spread over a surface by wettability.
  • the method consists in measuring the angle of the tangent of the profile of a drop deposited on the substrate, with the surface of the substrate.
  • This measure makes it possible, in particular, to discriminate the polar or apolar nature of the interactions at the liquid-solid interface and thus to deduce the hydrophilic or hydrophobic nature of a surface.
  • the more a large angle is measured the more the surface has a hydrophobic / oleophobic character.
  • the smaller the angle the more hydrophilic the surface.
  • the DSA100 apparatus associated with the DSA4 version 2.0 software were used to perform these contact angle measurements.
  • a brass surface that has been pre-treated or not with oxygen plasma has been treated with a dimer (OLEOXEIN +) according to the invention corresponding to the general formula (II) and which is the following:
  • pretreatment of the surface by oxygen plasma before treatment with a dimer of general formula (II) allows the latter to cling (adhere) more strongly to the treated surface and in particular to resist better hydrolysis in an acidic or basic medium, this conferring on the epilame a high stability over time.
  • pre-treatment with oxygen plasma makes it possible to significantly increase the resistance to successive washing cycles, whereas the treatment of the surface by immersion in a solution containing epilam lasted 5 or 15 minutes.
  • a plasma pretreatment of oxygen can significantly increase the resistance to successive wash cycles, that the treatment of the surface by immersion in a solution containing epilame lasted 5 or 15 minutes.
  • pre-treatment with oxygen plasma makes it possible to significantly increase the resistance to successive washing cycles, whereas the treatment of the surface by immersion in a solution containing epilam lasted 5 or 15 minutes.
  • pretreatment of the surface with oxygen plasma before treatment with a molecule of general formula (II) according to the invention, allows the latter to cling (to adhere) more strongly to the surface. treated and in particular better to resist hydrolysis in acidic or basic, this conferring on the epilame a high stability over time.
  • an oxygen plasma pretreatment significantly increases the resistance to successive washing cycles, that the treatment of the surface by immersion in a solution containing epilame lasted 5 or 15 minutes.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
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  • Application Of Or Painting With Fluid Materials (AREA)
EP16305039.6A 2016-01-15 2016-01-15 Oberflächenbehandlungsverfahren zum erzeugen einer oleophoben und/oder hydrophoben beschichtung Active EP3192853B1 (de)

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EP16305039.6A EP3192853B1 (de) 2016-01-15 2016-01-15 Oberflächenbehandlungsverfahren zum erzeugen einer oleophoben und/oder hydrophoben beschichtung

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EP16305039.6A EP3192853B1 (de) 2016-01-15 2016-01-15 Oberflächenbehandlungsverfahren zum erzeugen einer oleophoben und/oder hydrophoben beschichtung

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EP3192853A1 true EP3192853A1 (de) 2017-07-19
EP3192853B1 EP3192853B1 (de) 2023-04-26

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3799964A1 (de) * 2019-10-02 2021-04-07 ETA SA Manufacture Horlogère Suisse Herstellungsverfahren eines epilamisierten mechanischen bauteils

Citations (7)

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Publication number Priority date Publication date Assignee Title
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US20120148875A1 (en) * 2010-06-22 2012-06-14 Wd Media (Singapore) Pte. Ltd. Lubricant for magnetic disc, magnetic disc and method of producing the same
FR2967199A1 (fr) * 2010-11-10 2012-05-11 Vallourec Mannesmann Oil & Gas Procede de revetement d'un composant tubulaire filete, composant tubulaire filete et joint resultant
WO2013167624A1 (fr) * 2012-05-10 2013-11-14 Association Suisse Pour La Recherche Horlogère Recouvrement de surfaces destinees a l'horlogerie a l'aide de compositions catanioniques contenant des molecules phosphoniques et des amines
EP2687580A1 (de) * 2012-07-19 2014-01-22 Breitling AG Uhr
US20140087197A1 (en) 2012-09-21 2014-03-27 Apple Inc. Oleophobic coating on sapphire
EP2865737A1 (de) 2013-10-28 2015-04-29 The Swatch Group Research and Development Ltd. Edelprodukt aus Epilam

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EP3799964A1 (de) * 2019-10-02 2021-04-07 ETA SA Manufacture Horlogère Suisse Herstellungsverfahren eines epilamisierten mechanischen bauteils
WO2021063534A1 (fr) * 2019-10-02 2021-04-08 Eta Sa Manufacture Horlogère Suisse Procede de fabrication d'une piece mecanique epilamee
KR20220052367A (ko) * 2019-10-02 2022-04-27 에타 쏘시에떼 아노님 마누팍투레 홀로게레 스위세 에필람 처리된 기계적 부품을 제조하기 위한 방법
US12099330B2 (en) 2019-10-02 2024-09-24 Eta Sa Manufacture Horlogère Suisse Method for manufacturing an epilame mechanical part

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