EP2152775A1 - Procédé de production d'un matériau de revêtement - Google Patents

Procédé de production d'un matériau de revêtement

Info

Publication number
EP2152775A1
EP2152775A1 EP08734470A EP08734470A EP2152775A1 EP 2152775 A1 EP2152775 A1 EP 2152775A1 EP 08734470 A EP08734470 A EP 08734470A EP 08734470 A EP08734470 A EP 08734470A EP 2152775 A1 EP2152775 A1 EP 2152775A1
Authority
EP
European Patent Office
Prior art keywords
organic
silanes
functionalized silanes
coating material
monoalkoxy
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Withdrawn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
EP08734470A
Other languages
German (de)
English (en)
Inventor
Nora Laryea
Carolin Thurn
Stefan Sepeur
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.)
Nano X GmbH
Original Assignee
Nano X GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=39708162&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP2152775(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Nano X GmbH filed Critical Nano X GmbH
Priority to EP11173075.0A priority Critical patent/EP2385076B1/fr
Publication of EP2152775A1 publication Critical patent/EP2152775A1/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Withdrawn legal-status Critical Current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
    • C09D183/04—Polysiloxanes
    • 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
    • C09D183/02—Polysilicates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3206—Polyhydroxy compounds aliphatic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3802—Low-molecular-weight compounds having heteroatoms other than oxygen having halogens
    • C08G18/3804—Polyhydroxy compounds
    • C08G18/3812—Polyhydroxy compounds having fluorine atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/71—Monoisocyanates or monoisothiocyanates
    • C08G18/718—Monoisocyanates or monoisothiocyanates containing silicon
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • 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
    • C09D183/04—Polysiloxanes
    • C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • 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
    • C09D183/04—Polysiloxanes
    • C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
    • 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
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16

Definitions

  • the invention relates to a method for producing a coating material. It further relates to the use of the coating material.
  • Alternative powder coatings are epoxy- or acrylate-modified polymers which are crosslinked by means of appropriate catalysts and which are used, for example, as clearcoats for automotive applications.
  • these coating systems which are known for example from US 6,376,608 Bl, show only moderate chemical resistance or scratch resistance.
  • WO 2006/042658 A1 also describes reactions of isocyanates (HDI) with amino-functional silanes, which are crosslinked, for example, with appropriate catalysts, which, however, are only dissolved in aprotic solvents or aprotic solvent mixtures.
  • HDI isocyanates
  • US 2002/0042461 A1 discloses a compound having at least one cyclic olefin addition polymer which contains inter alia an organic carboxylic acid, phosphoric acid or sulfonic acid, ammonium, primary to tertiary amino compounds or a quaternary ammonium hydroxide compound and the optical transparency, solvent resistance, Has heat resistance and good adhesion to metals and inorganic substances.
  • the object of the invention is to provide a method for producing a new coating material in the form of a powder coating, can be made with the scratch-resistant coatings.
  • This object is achieved according to the invention by a method for producing a coating material, wherein one or more organic molecules, oligomers or polymers having at least one functional group with a silane having at least one functional organic group on an organic side chain to form a covalent bond between the organic molecule , Oligomer or polymer and the silane, so that a higher molecular weight silane results, which is directly curable by a catalyst.
  • the resulting compounds are present as a powder coating or as a flowable resin.
  • the first variant is particularly useful when the remaining functional groups perform a function, for example, antimicrobial, germ repellent, hormonal, enzymatic or biochemical in any other way.
  • Preferred embodiments of the invention are that the organic molecule, oligomer or polymer selected from the group consisting of alcohols, polyols, amines, isocyanates, hydrogen sulfide compounds, phosphates, anhydrides, carboxylic acids, methacrylates, acrylates, amino acids or DNA, hormones, enzymes, peptides, Sugars, polysaccharides, biomedical agents and natural products.
  • Preferred embodiments of the invention are that the silanes functionalized with an organic side chain group from the group consisting of monoamine-functionalized silanes (trialkoxy, dialkoxy, monoalkoxy), diamine-functionalized silanes (trialkoxy, dialkoxy, monoalkoxy), triamine functionalized Silanes, sec-amine-functionalized silanes, tert-amine-functionalized silanes, quat-amine functionalized silanes, dipodal-amine functionalized silanes, anhydride-functionalized silanes, acrylate- and methacrylate-functionalized silanes (trialkoxy, dialkoxy, monoalkoxy), epoxy -functionalized silanes (trialkoxy, dialkoxy, monoalkoxy), halogen-functionalized silanes (trialkoxy, dialkoxy, monoalkoxy), isocyanate and masked isocyanate-functionalized silanes, phosphate-functionalized silanes, sulfur-functionalized silanes, vinyl- and ole
  • silanes are the following: 3-aminopropyltriethoxysilane, aminoethylaminopropyltrimethoxysilane, aminoethylaminopropyltrimethoxysilane,
  • Triethoxysilylpropyldisulfidosilane bis-triethoxysilylpropyldisulfidosilane, bis-
  • Triethoxysilylpropyltetroasulfodosane N-cyclohexylaminomethylmethyldiethoxysilane, N-cyclohexylaminomethyltriethoxysilane, N-phenylaminomethyltrimethoxysilane,
  • the water content is at most 1%, and more preferably the reaction is carried out without the presence of water. In general, the humidity for the reaction is not disturbing.
  • the resulting compound which in turn represents a silane, has a molecular weight of at least 500 g / mol.
  • the silane or silanes are at least 5%, preferably at most 1% and more preferably not pre-crosslinked inorganic.
  • the organic molecule is selected from the group consisting of alcohols, amines, isocyanates, hydrogen sulfide compounds, phosphates, anhydrides, carboxylic acids, amino acids, hormones, enzymes, peptides, sugars, polysaccharides, and natural products.
  • An embodiment of the invention is that the reaction product is dissolved in protic or aprotic solvents.
  • solvents in particular alcohols, acetates, ethers or reaction diluents are added.
  • the dissolution takes place with heating to at least 50 0 C.
  • a development of the invention consists in using as catalysts up to 20% by weight, preferably 0.5 to 50% by weight of silanes, in particular aminosilanes, or Lewis acids or Lewis bases, in particular in the form of transition metal complexes, salts or particles, preferably micro- or nanoparticles.
  • transition metal complexes, salts or particles are titanium, aluminum, tin or zirconium complexes.
  • inorganic or organic particles in particular micro-, sub-micro- or nanoparticles are added as fillers.
  • matting agents wetting dispersants, UV absorbers, UV stabilizers, HALS stabilizers, free-radical scavengers, defoamers, waxes, biocides, preservatives, inorganic or organic fillers, Teflon particles, waxes or color pigments are added.
  • the coating material electrostatically, triboelectrically or wet-chemically, in particular by spraying, dipping, flooding, rolling, brushing, printing, spinning, knife coating or by evaporation in a vacuum on a substrate can be applied.
  • a further development of the method according to the invention is that the coating material after application at temperatures from room temperature to 1200 0 C, preferably from 50 0 C to 250 0 C curable, wherein the curing is preferably carried out thermally, with microwave radiation or UV radiation.
  • a development of the invention consists in that the curing takes place at room temperature by the addition of organic acids or bases or with UV light by free-radical or cationic polymerization after the addition of radically or cationically initiating photoinitiators.
  • hexanediol 11.8 g are heated with 49.5 g of ICTES (isocyanatopropyltriethoxysilane) to 80 0 C with stirring and mixed with 0.1 g of dibutyltin dilaurate. Thereafter, the mixture is allowed to cool to 50 0 C and further processed by method A and B.
  • ICTES isocyanatopropyltriethoxysilane
  • Stage 2 Method A Powder Coating Formulation: At this temperature, 10 g of reaction product are mixed with 0.1 g of aluminum acetylacetonate (50% dissolved in 2-butanol). This mixture is then further slowly cooled to room temperature. The subsequently crystallized resin is then comminuted in a special mill in particle sizes of ⁇ 50 microns and sieved. As a leveling additive 0.8% Byk 359 are added to the powder and mixed well.
  • the powder thus produced is then applied by electrostatic or triboelectric spraying onto an already colored steel sheet and dried at 130 0 C in a convection oven.
  • reaction product 80 g of the reaction product are dissolved in 20 g of 1-methoxy-2-propanol and 0.2 g
  • Base lacquer-painted steel plate the drying takes place in a convection oven at 150 0 C for about 20 min cured.
  • the obtained layer according to method A and B produced samples show excellent scratch resistance to steel wool and chemical resistance to 36% sulfuric acid without attack (etching) of> 30 min.
  • reaction product (stage 1) are dissolved in 1 g of isopropanol and 0.1 g
  • polycarbonate substrates are coated by flooding and at 130 0 C for 60 min. Hardened in a convection oven.
  • the polycarbronate substrates are flooded before application with a primer (0.5% 3-aminoproyltriethoxysilane solution in ethanol) and treated at room temperature for 5 min
  • the layers show very high scratch resistance against punctate marks, e.g. by key or screwdriver. After 1000 h in the QUV test, the layers show no visible visible yellowing
  • Step 1
  • 3 g of the waxy mixture are then mixed with 0.1 g of zirconium lactate and 9 g of ethanol. Thereafter, a stainless steel plate (degreased and oil-free) is sprayed with the mixture and cured at 180 ° C for 1 h in a drying oven.
  • the coated surface shows a significantly less visible fingerprint after exposure to the surface with a finger greased with Nivea Creme compared to untreated surface. After 1 h, the fingerprint is wiped with a dry paper towel and also shows a much better residue-free cleaning compared to the reference. The fingerprint is still visible after rubbing on the untreated surface. Then the surface is treated with edible oil and water and shows in comparison to uncoated stainless steel surface a strong drop formation, whereby the drops can be easily removed from the surface with a dry cloth without residue.
  • the mixture was then applied to a polycarbonate plate by dipping and then dried at 130 ° C.
  • the coated sample disc is placed over a distance of 15 cm over a pot of boiling water and observed for 20 sec. There was no fogging of the coated plate side in this test.

Abstract

L'invention concerne un procédé de production d'un matériau de revêtement, ainsi que l'utilisation d'un tel matériau de revêtement. L'invention a pour but de disposer d'un procédé de production d'un nouveau matériau de revêtement, capable de fournir des revêtements résistant aux rayures et pouvant être utilisé sous forme de peinture en poudre. A cet effet, l'invention est caractérisée en ce qu'on fait réagir une ou plusieurs molécules organiques, un ou plusieurs oligomères ou polymères ayant au moins un groupe fonctionnel présentant un ou plusieurs silanes ayant au moins un groupe organique fonctionnel sur une chaîne latérale organique, avec formation d'une liaison covalente entre les molécules organiques, l'oligomère ou le polymère et le silane, de manière à obtenir un silane hautement moléculaire directement durcissable par un catalyseur. On a découvert avec surprise qu'en faisant réagir des silanes fonctionnalisés organiquement, par exemple, ayant une fonction NCO (et, de toute façon, légèrement pré-réticulés), avec des partenaires de réaction appropriés, on obtenait une nouvelle classe de composés pouvant être utilisés comme matériaux de revêtement, par exemple sous forme de peintures en poudre ou de liants hautement solides, par exemple à 100% de résines.
EP08734470A 2007-04-27 2008-04-08 Procédé de production d'un matériau de revêtement Withdrawn EP2152775A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP11173075.0A EP2385076B1 (fr) 2007-04-27 2008-04-08 Procédé de fabrication d'un matériau de revêtement

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102007020404A DE102007020404A1 (de) 2006-09-18 2007-04-27 Verfahren zur Herstellung eines Beschichtungsmaterials
PCT/DE2008/000586 WO2008131715A1 (fr) 2007-04-27 2008-04-08 Procédé de production d'un matériau de revêtement

Related Child Applications (1)

Application Number Title Priority Date Filing Date
EP11173075.0A Division EP2385076B1 (fr) 2007-04-27 2008-04-08 Procédé de fabrication d'un matériau de revêtement

Publications (1)

Publication Number Publication Date
EP2152775A1 true EP2152775A1 (fr) 2010-02-17

Family

ID=39708162

Family Applications (2)

Application Number Title Priority Date Filing Date
EP08734470A Withdrawn EP2152775A1 (fr) 2007-04-27 2008-04-08 Procédé de production d'un matériau de revêtement
EP11173075.0A Not-in-force EP2385076B1 (fr) 2007-04-27 2008-04-08 Procédé de fabrication d'un matériau de revêtement

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP11173075.0A Not-in-force EP2385076B1 (fr) 2007-04-27 2008-04-08 Procédé de fabrication d'un matériau de revêtement

Country Status (8)

Country Link
US (1) US20100092686A1 (fr)
EP (2) EP2152775A1 (fr)
JP (1) JP2010524670A (fr)
KR (1) KR20100017394A (fr)
CN (1) CN101679598B (fr)
DE (1) DE102007020404A1 (fr)
RU (1) RU2468042C2 (fr)
WO (1) WO2008131715A1 (fr)

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US20100092686A1 (en) 2010-04-15
WO2008131715A1 (fr) 2008-11-06
EP2385076B1 (fr) 2016-03-23
KR20100017394A (ko) 2010-02-16
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JP2010524670A (ja) 2010-07-22
DE102007020404A1 (de) 2008-10-30

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