WO2008131715A1 - Verfahren zur herstellung eines beschichtungsmaterials - Google Patents
Verfahren zur herstellung eines beschichtungsmaterials Download PDFInfo
- Publication number
- WO2008131715A1 WO2008131715A1 PCT/DE2008/000586 DE2008000586W WO2008131715A1 WO 2008131715 A1 WO2008131715 A1 WO 2008131715A1 DE 2008000586 W DE2008000586 W DE 2008000586W WO 2008131715 A1 WO2008131715 A1 WO 2008131715A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- organic
- silanes
- functionalized silanes
- coating material
- monoalkoxy
- Prior art date
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.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2010504438A JP2010524670A (ja) | 2007-04-27 | 2008-04-08 | コーティング材料の製造方法 |
EP08734470A EP2152775A1 (de) | 2007-04-27 | 2008-04-08 | Verfahren zur herstellung eines beschichtungsmaterials |
CN200880016878.7A CN101679598B (zh) | 2007-04-27 | 2008-04-08 | 制备涂层材料的方法 |
RU2009143809/04A RU2468042C2 (ru) | 2007-04-27 | 2008-04-08 | Способ получения материала для покрытий |
US12/451,131 US20100092686A1 (en) | 2007-04-27 | 2008-04-28 | Method for the production of a coating material |
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 |
DE102007020404.5 | 2007-04-27 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2008131715A1 true WO2008131715A1 (de) | 2008-11-06 |
Family
ID=39708162
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/DE2008/000586 WO2008131715A1 (de) | 2007-04-27 | 2008-04-08 | Verfahren zur herstellung eines beschichtungsmaterials |
Country Status (8)
Country | Link |
---|---|
US (1) | US20100092686A1 (de) |
EP (2) | EP2152775A1 (de) |
JP (1) | JP2010524670A (de) |
KR (1) | KR20100017394A (de) |
CN (1) | CN101679598B (de) |
DE (1) | DE102007020404A1 (de) |
RU (1) | RU2468042C2 (de) |
WO (1) | WO2008131715A1 (de) |
Cited By (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009114580A2 (en) | 2008-03-11 | 2009-09-17 | 3M Innovative Properties Company | Hardcoat composition |
EP2235124A2 (de) * | 2007-12-27 | 2010-10-06 | 3M Innovative Properties Company | Schutzbeschichtungszusammensetzungen |
EP2479225A2 (de) * | 2009-09-18 | 2012-07-25 | LG Chem, Ltd. | Neuartige verwendung eines lipolyseenzyms zur formung einer fingerabdruckresistenten beschichtung, substrat mit der in diesem verfahren geformten fingerabdruckresistenten beschichtung und produkte mit dem substrat |
EP2479226A2 (de) * | 2009-09-18 | 2012-07-25 | LG Chem, Ltd. | Poröse struktur zur bildung einer fingerabdruckfesten beschichtung, verfahren zur bildung einer fingerabdruckfesten beschichtung mit der porösen struktur, substrat mit der in diesem verfahren gebildeten fingerabdruckfesten beschichtung und produkte mit dem substrat |
WO2013110566A1 (de) | 2012-01-27 | 2013-08-01 | Basf Se | Strahlungshärtbare antimikrobielle beschichtungsmasse |
WO2013110504A1 (en) | 2012-01-27 | 2013-08-01 | Basf Se | Radiation-curable antimicrobial coatings |
DE102012204298A1 (de) | 2012-03-19 | 2013-09-19 | Evonik Degussa Gmbh | Nicht wässriges, bei Umgebungstemperatur härtendes Beschichtungsmittel |
DE102012204290A1 (de) | 2012-03-19 | 2013-09-19 | Evonik Degussa Gmbh | Addukte aus Isocyanatoalkyl-trialkoxysilanen und aliphatischen, alkyl-verzweigten Diolen oder Polyolen |
EP2676982A1 (de) | 2012-06-20 | 2013-12-25 | Evonik Industries AG | Beschichtungsmittel mit hoher Kratzbeständigkeit |
WO2013189882A2 (de) | 2012-06-20 | 2013-12-27 | Evonik Industries Ag | Beschichtungsmittel mit hoher kratzbeständigkeit |
US8728455B2 (en) | 2012-01-27 | 2014-05-20 | Basf Se | Radiation-curable antimicrobial coatings |
EP2735578A1 (de) | 2012-11-26 | 2014-05-28 | Evonik Industries AG | Beschichtungsmittel mit hoher Kratzbeständigkeit |
US9051423B2 (en) | 2009-09-16 | 2015-06-09 | 3M Innovative Properties Company | Fluorinated coating and phototools made therewith |
US9096712B2 (en) | 2009-07-21 | 2015-08-04 | 3M Innovative Properties Company | Curable compositions, method of coating a phototool, and coated phototool |
CN104829808A (zh) * | 2014-02-10 | 2015-08-12 | 赢创工业集团股份有限公司 | 异氰酸根合烷基三烷氧基硅烷和氨基甲酸酯二醇的共聚物 |
EP3078723A1 (de) | 2015-04-09 | 2016-10-12 | Evonik Degussa GmbH | Addukte aus isocyanatoalkyltrimethoxysilanen und mit ihnen reaktiven flammschutzmitteln |
WO2017055418A1 (de) | 2015-09-30 | 2017-04-06 | Evonik Degussa Gmbh | Mit silikonharzen modifizierte isocyanatoalkylalkoxysilan-addukte und ihre verwendung |
EP3162827A1 (de) | 2015-10-29 | 2017-05-03 | Evonik Degussa GmbH | Beschichtungsmittel mit monoallophanaten auf basis von alkoxysilanalkylisocyanaten |
EP3263616A1 (de) | 2016-06-27 | 2018-01-03 | Evonik Degussa GmbH | Alkoxysilan-funktionalisierte allophanat-haltige beschichtungsmittel |
EP3263619A1 (de) | 2016-06-27 | 2018-01-03 | Evonik Degussa GmbH | Alkoxysilan- und allophanat-funktionalisierte beschichtungsmittel |
WO2020040738A1 (en) | 2018-08-21 | 2020-02-27 | Evonik Degussa Gmbh | Heat-curable coating compositions containing silane-functional polyurethane resins catalyzed by amidine salts |
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Also Published As
Publication number | Publication date |
---|---|
EP2152775A1 (de) | 2010-02-17 |
CN101679598A (zh) | 2010-03-24 |
JP2010524670A (ja) | 2010-07-22 |
KR20100017394A (ko) | 2010-02-16 |
US20100092686A1 (en) | 2010-04-15 |
EP2385076A1 (de) | 2011-11-09 |
DE102007020404A1 (de) | 2008-10-30 |
EP2385076B1 (de) | 2016-03-23 |
CN101679598B (zh) | 2014-01-01 |
RU2009143809A (ru) | 2011-06-10 |
RU2468042C2 (ru) | 2012-11-27 |
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