EP1704193A2 - Revetement hydrophile a base de polysilazane - Google Patents

Revetement hydrophile a base de polysilazane

Info

Publication number
EP1704193A2
EP1704193A2 EP04803939A EP04803939A EP1704193A2 EP 1704193 A2 EP1704193 A2 EP 1704193A2 EP 04803939 A EP04803939 A EP 04803939A EP 04803939 A EP04803939 A EP 04803939A EP 1704193 A2 EP1704193 A2 EP 1704193A2
Authority
EP
European Patent Office
Prior art keywords
polysilazane
ionic
coating
reagent
hydrophilic
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Withdrawn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
EP04803939A
Other languages
German (de)
English (en)
Inventor
Andreas Dierdorf
Hubert Liebe
Andreas Wacker
Günter MOTZ
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.)
Clariant International Ltd
Original Assignee
Clariant International Ltd
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 Clariant International Ltd filed Critical Clariant International Ltd
Publication of EP1704193A2 publication Critical patent/EP1704193A2/fr
Withdrawn legal-status Critical Current

Links

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
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/16—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers in which all the silicon atoms are connected by linkages other than oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C03—GLASS; MINERAL OR SLAG WOOL
    • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
    • C03C17/28—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material
    • C03C17/30—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material with silicon-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • 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
    • C03C2217/00—Coatings on glass
    • C03C2217/70—Properties of coatings
    • C03C2217/75—Hydrophilic and oleophilic coatings

Definitions

  • the present invention relates to a transparent, permanently hydrophilic coating based on polysilazane in combination with an ionic reagent to increase the hydrophilicity.
  • Hydrophilic surfaces are characterized by good wettability with water, which is expressed measurably in a low contact angle. Such hydrophilic
  • certain detergents are suitable for temporarily imparting hydrophilicity to surfaces.
  • Such formulations have been available for a long time and are used, among other things. used as an anti-fog agent for glasses and optical devices, but these agents do not adhere to the surface and therefore only have an effect for a short time.
  • EP-0498 005 A1 describes an aqueous / alcoholic formulation based on a vinylpyrrolidone / vinyl acetate copolymer which is used as an anti-fogging agent for spectacle lenses.
  • hydrophilic coating materials consist of organic polymers or copolymers that contain polar groups. This
  • Coatings are characterized by the fact that they are able to absorb water and thus the surface is wetted with a water film.
  • a disadvantage of such coatings is their low abrasion resistance, moreover Due to the water absorption, the polymer swells, which causes the surface to dissolve or detach.
  • either UV curing or temperature treatment is necessary for curing such polymeric systems, which on the one hand is associated with high technical outlay and thus on costs and on the other hand is not suitable for temperature-sensitive substrates.
  • EP-0 339 909 B1 describes a thermally curable coating composition which contains polar copolymers which are composed of condensates of methacrylamide and further hydrophilic monomers. This formulation is applied to polycarbonate and PMMA and cured at 80-120 ° C.
  • EP-1 118 646 A1 describes a UV-curable coating composition with anti-fogging properties based on polyalkylene oxide di (meth) acrylates, hydroxyalkyl (methacrylates) and alkane polyol poly (methacrylates), which is applied to polycarbonate plates, cured and leads to a reduction in fogging ,
  • Fine-particle titanium dioxide particles in the anatase modification have photocatalytic properties and are also suitable for hydrophilically modifying surfaces.
  • the photocatalytic effect and the associated hydrophilicity only occur when these particles are exposed to UV radiation, i.e. they are not suitable for indoor use.
  • these particles tend to be organic
  • EP-0 913447 A1 describes a formulation based on photocatalytically active nano-metal oxides which, when applied to a glass pane and after irradiation with UV light, shows no quality of fogging when breathed on.
  • the adhesion of this anti-fog coating checked where, after erasing two or three times with an eraser, the coating can be completely removed.
  • Silicate surfaces such as glass and ceramics or surfaces made of metal oxides can be coated with halogen or alkoxysilanes which carry hydrophilic substituents. These react with the oxidic surface and are thus covalently bound. Due to the chemical bond between the substrate and the silane, the hydrophilic substituents are permanently fixed on the surface and their effects are retained.
  • No. 6,489,499 B1 describes a method for producing a hydrophilically modified glass surface, in which a solution of a siloxane-modified ethylene diamine tricarboxylic acid salt is used.
  • no quantitative statement about the contact angle is made, but only that the wetting of a coated glass surface to which a drop of water is applied is better than without a coating.
  • the disadvantage is that these silanes do not react with surfaces that do not contain oxide or hydroxide groups. For example, plastics, paints and resins cannot be given a hydrophilic effect with the aid of the hydrophilic silanes. Another disadvantage of this
  • Hydrophilizing reagents are that because of their low molecular weight they diffuse into the substrate on strongly absorbent surfaces or surfaces with large pores without sufficiently covering the surface with a hydrophilic effect.
  • Polysilazanes are suitable for the production of thin layers that can be used to protect substrates from scratches or corrosion, for example.
  • WO 02/088269 A1 describes a dirt-repellent coating solution based on polysilazane, but without aftertreatment with a further hydrophilizing reagent. By coating a surface with polysilazane and then curing in air, relatively hydrophilic surfaces are already obtained which have a contact angle of 30-40 ° C.
  • the object of the present invention was to develop an easy-to-use coating with which it is possible to provide a wide variety of materials such as glass, ceramics, metals, plastics, paints, resins and porous surfaces with a permanent hydrophilic effect.
  • the invention therefore relates to a hydrophilic coating for surfaces containing one or more polysilazanes and an ionic reagent or mixtures of ionic reagents to increase the hydrophilicity.
  • ionic reagents By applying ionic reagents to the polysilazane layer, charge is fixed on the substrate surface, which leads to a surface with high surface energy, which enables easy wetting with water. It is irrelevant whether the charge is a cationic or an anionic.
  • Polysilazanes are very reactive inorganic or organic polymers. Thanks to their high reactivity, they adhere very well to a wide variety of surfaces by forming permanent chemical bonds and are also able to react chemically with other applied reagents, and thus these reagents as well bind permanently.
  • the hydrophilic coating contains at least one polysilazane of the formula 1,
  • the hydrophilizing agents are ionic compounds which are generally applied in solution to the polysilazane coating applied first, react with it and therefore permanently adhere to it. These can be a wide variety of reagents that enable the desired permanent hydrophilic effect in combination with the polysilazane coating.
  • ionic hydrophilizing agents can be, for example
  • Salts of carboxylic acids in particular of hydroxycarboxylic acids, such as calcium, sodium or potassium gluconate, salts of tartaric acid, citric acid, malic acid, lactic acid or sugar acid. Solutions of these salts can also be obtained directly by reacting the corresponding acid with lyes.
  • Substituted ionic halogen-, hydroxy-, alkoxy- or alkylsilanes such as N- (trimethoxylsilylpropyl) ethylenediaminetriacetic acid, trisodium salt, N-trimethoxysilylpropyl-N, N, N-trimethylammonium chloride, N- (3-triethoxysilylpropyl) gluconyloxyl, grapplonyl amide ) -O- polyethylene oxide urethane, 1-trihydroxysilylpropionic acid disodium salt are suitable hydrophilizing agents.
  • Ionic oligomers or polymeric compounds such as surfactants or dispersing additives such as Byk®-151, Byk®-LP N 6640, Anti-Terra®-203, Disperbyk®-140, Byk®-9076, Byk®-154, Disperbyk®, Disperbyk® -181 are also suitable hydrophilizing agents.
  • Salts such as titanium phosphate which are similar to anatase Modification of titanium dioxide by irradiation with UV light can become "super-hydrophilic".
  • titanium phosphate has the advantage over anatase that it is not so aggressive towards organic materials and does not destroy them.
  • hydrophilization aids have in common that the contact angle of a surface coated with polysilazane is smaller than is observed without the use of these reagents.
  • the invention further relates to a method for producing a hydrophilic coating comprising one or more polysilazanes and an ionic reagent or mixtures of ionic reagents, in which the coating of a surface with at least one polysilazane is carried out in a first step and then an ionic hydrophilizing reagent in a second step or a mixture of ionic hydrophilizing reagents can be applied in a solvent.
  • Another object of the invention is a hydrophilic surface, obtainable by coating with the aforementioned polysilazanes and ionic hydrophilizing reagents.
  • Suitable substrates include:
  • Plastics such as Iron, stainless steel, galvanized steel, zinc, aluminum, nickel, copper, magnesium and their alloys, silver and gold, plastics, e.g. Polymethyl methacrylate, polyurethane, polycarbonate, polyesters such as polyethylene terephthalate, polyimides, polyamides, epoxy resins, ABS plastic, polyethylene, polypropylene, polyoxymethylene, porous mineral materials such as concrete, clay brick, marble, basalt,
  • Paint surfaces such as plastic emulsion paints, acrylic paints, Epoxy paints, melamine resins, polyurethane resins and alkyd paints and organic materials such as wood, leather, parchment, paper and textiles glass,
  • the coating with polysilazane can be carried out by wiping, dipping, spraying or spin-coating pure polysilazane or a polysilazane solution.
  • a thin layer of polysilazane is necessary, which is transparent and therefore the optical appearance of the
  • the layer thickness of the polysilazane layer is in the range from 0.01 to 10 micrometers, preferably 0.05 to 5 micrometers, particularly preferably 0.1 to 1 micrometers. It is possible to pretreat the surface to be coated with a primer first.
  • the subsequent coating with the hydrophilizing agent can also be carried out by dipping, spraying, spin coating or wiping.
  • Both the coating with polysilazane and the subsequent application of the ionic reagent are preferably carried out at a temperature in the range from 5 to 40 ° C., application at room temperature is particularly advantageous, which also enables the coating of temperature-sensitive substrates.
  • the coating time can be shortened considerably.
  • Particularly suitable solvents for polysilazane are organic solvents which contain no water and no reactive groups (such as hydroxyl or amine groups). These are, for example, aliphatic or aromatic hydrocarbons, halogenated hydrocarbons, esters such as ethyl acetate or butyl acetate, ketones such as acetone or methyl ethyl ketone, ethers such as tetrahydrofuran or dibutyl ether, and also mono- and polyalkylene glycol dialkyl ethers (Glymes) or mixtures of these solvents.
  • organic solvents which contain no water and no reactive groups (such as hydroxyl or amine groups). These are, for example, aliphatic or aromatic hydrocarbons, halogenated hydrocarbons, esters such as ethyl acetate or butyl acetate, ketones such as acetone or methyl ethyl ketone, ethers such as tetrahydrofuran or dibutyl
  • Another component of the polysilazane solution can be catalysts, such as tertiary amines, which accelerate the hardening of the polysilazane film or additives which facilitate the wetting of the background or film formation.
  • catalysts such as tertiary amines
  • Particularly suitable solvents for the hydrophilizing reagent are water, alcohols such as methanol, ethanol, isopropanol, ketones such as acetone or methyl ethyl ketone, carboxylic acids such as formic acid, acetic acid or propionic acid and esters such as ethyl acetate or butyl acetate or mixtures of these solvents.
  • the coatings with polysilazanes were carried out in an inert gas atmosphere in a glove box.
  • the various substrates were coated using a dipping apparatus.
  • the contact angle measurements were carried out on a Krüss device.
  • Perhydropolysilazane was used in various solvents as the polysilazane.
  • Mixtures of xylene and pegasol (name NP) or di-n-butyl ether (name NL) are common. Manufacturer is Clariant Japan K.K.
  • a polycarbonate disc (10 x 10 cm) was in a glove box with the help of a diving apparatus with a stepper motor at a speed of 20 cm / min. immersed in a 20% perhydropolysilazane solution in n-dibutyl ether. After a dwell time of 10 s, it was run at a speed of 20 cm / min. pulled out of the solution again. Allow to drain briefly and then take the sample out of the glove box. The sample is left in the air for 10 minutes and then immersed in an aqueous solution (10%) of the additive Byk-LP N-6640 (original solution is 40%, diluted 3: 1 with water). The sample is left in the solution for 24 hours and then rinsed off with water.
  • the contact angle of water could not be determined exactly, but was clearly below 10 °.
  • a stainless steel sample V2A was coated as described above.
  • the aqueous solution of the Byk additive was heated to 50 ° C and the steel sample for 30 min. dipped.
  • the contact angle of water was well below 10 °.
  • a stainless steel sample was used as described in experiment 2. Instead of the Byk additive, the sample was immersed in an aqueous, saturated Ca gluconate solution. After 24 hours, a contact angle of less than 10 ° could be measured.
  • a stainless steel sample was used as described in experiment 4.
  • the saturated Ca gluconate solution was heated to 50 ° C. and the sample was stored for 30 minutes.
  • the contact angle of water was well below 10 °.
  • a stainless steel sample was used as described in experiment 2. Instead of the Byk additive, the sample was immersed in a 10% aqueous solution of the disodium salt of carboxyethylsilanetriol for 24 hours. The contact angle of water was less than 10 °.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Geochemistry & Mineralogy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Paints Or Removers (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Silicon Polymers (AREA)
  • Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
  • Laminated Bodies (AREA)
  • Surface Treatment Of Glass (AREA)
  • Chemical Treatment Of Metals (AREA)

Abstract

L'invention concerne un revêtement hydrophile destiné à des surfaces, qui contient un ou plusieurs polysilazanes et un réactif ionique ou des mélanges de réactifs ioniques. Ce polysilazane est notamment un polysilazane de formule (1), (SiR'R"-NR"')n-, dans laquelle R', R", R" peuvent être identiques ou différents et représenter hydrogène ou des restes organiques ou organométalliques et n est calculé de sorte que le polysilazane présente un poids moléculaire moyen en nombre compris entre 150 et 150 000 g/mol. Dans un mode de réalisation préféré, le polysilazane est un perhydropolysilazane (R'=R"=R" = H). Le réactif ionique est de préférence un sel d'un acide carboxylique, notamment d'un acide hydroxycarboxylique, ou un silane cationique ou anionique, ou un oligomère ou un polymère. L'invention concerne en outre un procédé pour produire lesdits revêtements hydrophiles.
EP04803939A 2004-01-07 2004-12-16 Revetement hydrophile a base de polysilazane Withdrawn EP1704193A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004001288A DE102004001288A1 (de) 2004-01-07 2004-01-07 Hydrophile Beschichtung auf Polysilazanbasis
PCT/EP2004/014326 WO2005066285A2 (fr) 2004-01-07 2004-12-16 Revetement hydrophile a base de polysilazane

Publications (1)

Publication Number Publication Date
EP1704193A2 true EP1704193A2 (fr) 2006-09-27

Family

ID=34744635

Family Applications (1)

Application Number Title Priority Date Filing Date
EP04803939A Withdrawn EP1704193A2 (fr) 2004-01-07 2004-12-16 Revetement hydrophile a base de polysilazane

Country Status (13)

Country Link
US (1) US20070116968A1 (fr)
EP (1) EP1704193A2 (fr)
JP (1) JP2007517943A (fr)
KR (1) KR20060126535A (fr)
AR (1) AR047368A1 (fr)
AU (1) AU2004312142A1 (fr)
BR (1) BRPI0418370A (fr)
CA (1) CA2552733A1 (fr)
DE (1) DE102004001288A1 (fr)
NO (1) NO20063228L (fr)
RU (1) RU2006128576A (fr)
TW (1) TW200528527A (fr)
WO (1) WO2005066285A2 (fr)

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JP2019210370A (ja) * 2018-06-04 2019-12-12 メルク、パテント、ゲゼルシャフト、ミット、ベシュレンクテル、ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ ＧｍｂＨ ポリシラン骨格を有するブロックとポリシラザン骨格を有するブロックとを含んでなるブロックコポリマー
CN108906557B (zh) * 2018-08-03 2021-04-06 广州弘海化工科技有限公司 一种长效超亲水聚硅氮烷涂层及其制备方法
KR102170244B1 (ko) * 2019-01-02 2020-10-28 금오공과대학교 산학협력단 마그네슘 합금 표면상의 무기 폴리실라잔 코팅 방법 및 이에 의해 형성된 마그네슘 합금
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Also Published As

Publication number Publication date
BRPI0418370A (pt) 2007-05-15
KR20060126535A (ko) 2006-12-07
US20070116968A1 (en) 2007-05-24
CA2552733A1 (fr) 2005-07-21
WO2005066285A3 (fr) 2005-08-18
NO20063228L (no) 2006-08-09
AU2004312142A1 (en) 2005-07-21
JP2007517943A (ja) 2007-07-05
AR047368A1 (es) 2006-01-18
DE102004001288A1 (de) 2005-08-11
TW200528527A (en) 2005-09-01
RU2006128576A (ru) 2008-02-20
WO2005066285A2 (fr) 2005-07-21

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