WO2019121389A1 - Compositions d'agent de revêtement pour le revêtement de mousses dans un procédé dans le moule - Google Patents

Compositions d'agent de revêtement pour le revêtement de mousses dans un procédé dans le moule Download PDF

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Publication number
WO2019121389A1
WO2019121389A1 PCT/EP2018/084942 EP2018084942W WO2019121389A1 WO 2019121389 A1 WO2019121389 A1 WO 2019121389A1 EP 2018084942 W EP2018084942 W EP 2018084942W WO 2019121389 A1 WO2019121389 A1 WO 2019121389A1
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Prior art keywords
component
radical
weight
coating composition
solvent
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PCT/EP2018/084942
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German (de)
English (en)
Inventor
Karin REUTER
Lea FEDELER
Robert Frenzel
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Basf Coatings Gmbh
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Publication of WO2019121389A1 publication Critical patent/WO2019121389A1/fr

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    • 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
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • 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
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/227—Catalysts containing metal compounds of antimony, bismuth or arsenic
    • 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
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/281—Monocarboxylic acid compounds
    • 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
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
    • 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
    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
    • C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
    • C08G18/6225—Polymers of esters of acrylic or methacrylic acid
    • C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
    • 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
    • C08G18/78—Nitrogen
    • C08G18/7875—Nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring
    • C08G18/7887—Nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring having two nitrogen atoms in the ring
    • 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
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
    • C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
    • 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

Definitions

  • the present invention relates to two-component coating compositions which are suitable for coating foams in the in-mold coating process, to a process for coating foams and to the use of the two-component coating compositions for producing coated foams.
  • Suitable substrates of the prior art which already allow a certain weight reduction, are, for example, aluminum and high-performance steels.
  • Foams such as rigid foams and flexible foams, in particular as used in the automotive interior, for example in the equipment, upholstery and insulation, require high-quality foams
  • foams often have an irregular surface structure, which is usually rough and also partially open fibers or pores and their irregularity propagates to the coating surface after coating by the coating layers, usually filler layers, basecoat films and clearcoat films.
  • variable layer thicknesses Possible methods with which variable layer thicknesses can be produced are the overmolding process (injection-in-mold coating process) or the conventional in-mold coating process.
  • the painting is carried out as well as the application of the reinforcing material in a non-closed tool, while in closed process, the tool is closed after the application of the paint layer, before subsequently fed to the foam-forming composition and foamed.
  • the coating agent In all processes in which the coating agent is in contact with a tool surface, however, it also requires removal of the coating from the tool surface without damage to the surface damage. This can be achieved conventionally by providing the tool surface before use with a so-called external release agent or release agent. When using a demolding or release agent, however, this remains partially after the coating of the substrate with the coating agent on the tool surface, but also on the coating agent surface. Before a subsequent coating with, for example, a basecoat or the bonding with other components, this must be removed by a complex cleaning process.
  • Bleeding times in the mold need before the tool is closed and the foam-forming material is injected.
  • the coatings should preferably be recoated without expensive subsequent cleaning steps and / or grinding steps with a further coating layer, for example a basecoat and clearcoat.
  • foams or other materials with a porous surface should be seamlessly provided with highly elastic, flexible coatings, which are also UV-resistant.
  • a solvent-based two-component coating composition comprising a base paint component A and a curing agent component B, wherein the
  • hydroxy-functional poly (meth) acrylates A1 having a hydroxyl number of 50 to 120 mg KOH / g, preferably 65 to 100 mg KOH / g, more preferably 70 to 95 mg
  • polyester polyols A2 having a hydroxyl number of 100 to 200 mg KOH / g, preferably 110 to 180 mg KOH / g, particularly preferably 120 to 160 mg KOH / g;
  • R 1 - (C O) r -O- (AO) s R 2 (I) wherein R 1 is a saturated or unsaturated, aliphatic
  • Hydrocarbon radical having 6 to 30 carbon atoms
  • R 2 is H, a radical PO (OH) 2 or the optionally partially phosphated radical of a mono- or disaccharide or the optionally partially phosphated radical of an alditol, AO for one or more alkylene oxide radicals selected from the group consisting of ethylene oxide, propylene oxide and
  • crosslinking catalysts A4 selected from the group of bismuth carboxylates
  • additives A 7 selected from the group consisting of wetting and / or dispersing agents, rheology auxiliaries and leveling agents; contains and where the
  • i. contains at least one polyisocyanate B1, which has on average 2.4 to 5 NCO groups and contains at least one isocyanurate ring and
  • ii. contains at least one polyisocyanate B1, which has on average 2.4 to 5 NCO groups and at least one
  • Iminooxadiazinedione ring contains.
  • the two-component coating composition of the invention preferably has a solids content of from 30 to 60% by weight, more preferably from 35 to 55% by weight, most preferably from 40 to 50% by weight, and especially from 42 to 48% by weight, for example 43 to 47 wt .-% based on the total weight of the two-component coating composition.
  • the molar ratio of the NCO groups of the Flärter component B to the sum of the flydroxyl groups of the constituents A1 and A2 of the parent lacquer component A is preferably from 0.4: 1 to 1: 1, more preferably from 0.65: 1 to 0.85: 1, and most preferably from 0.7: 1 to 0.8: 1.
  • the specified ratio can be used to adjust the elasticity of the coating and its soiling tendency. The closer the ratio comes to 0.4: 1, the higher the elasticity of the
  • two-component coating composition refers to coating materials in which the reaction which leads to curing is initiated by mixing two components (stock paint and hardener) in a predetermined ratio.
  • the individual components are not coating materials, since they either are not capable of film formation or do not give any stable films (Rompp varnishes and printing inks, keyword two-component varnish).
  • poly (meth) acrylate means both polyacrylates and
  • Poly (meth) acrylates can therefore be selected from acrylates and / or
  • Methacrylates be constructed and contain other ethylenically unsaturated monomers such as styrene or acrylic acid.
  • aliphatic radical as used herein means a radical, an acyclic or cyclic, saturated or unsaturated carbon compound containing no aromatic structures (see: IUPAC Compendium of Chemical
  • Heteroatoms such as oxygen or nitrogen.
  • the solids content was determined according to ASTM D2369 (from 2015) at 110 ° C for 60 minutes on a sample of about 2 grams of the two-component coating composition. Analog is used in the determination the solid body of the base paint component A and the hardener component B method.
  • constituents of the base lacquer component A and hardener component B which are described in more detail below, in particular also the optionally differently strongly preferred constituents, can generally be selected independently of one another, so that, for example, the selection of a very particularly preferred constituent does not require that it only be used with other preferred, particularly preferred or very particularly preferred components can be combined. This is not precluded by the fact that in some cases it may be particularly useful and preferable to choose another preferred ingredient when using one particular preferred ingredient. Therefore, if preferred combinations are described below, they are not considered to be mandatory
  • the hydroxy-functional poly (meth) acrylates A1 have a hydroxyl number of 50 to 120 mg KOH / g.
  • the hydroxy-functional poly (meth) acrylates A1 preferably have one
  • hydroxyl number can be in the context of the present invention according to
  • the hydroxy-functional poly (meth) acrylates A1 preferably have an acid number of less than 25 mg KOH / g, particularly preferably an acid number of 1 to 20 mg KOH / g, very particularly preferably an acid number of 4 to 16 mg KOH / g, in particular 6 to 14 mg KOH / g or 8 to 12 mg KOH / g.
  • the acid number can be determined in the context of the present invention according to DIN EN ISO 2114: 2002-06 (method A).
  • the number average molecular weight M n and the weight average molecular weight M w can be determined by gel permeation chromatography (GPC) using a polymethyl methacrylate standard (PMMA standard).
  • the number-average molecular weight M n of the hydroxy-functional poly (meth) acrylates A1 is preferably in a range from 4000 to 10000 g / mol, more preferably 5000 to 9000 g / mol and very particularly preferably 5500 to 8000 g / mol, in particular 6000 to 7500 g / mol.
  • Poly (meth) acrylates A1 is preferably in a range from 8000 to 30,000 g / mol, particularly preferably 10,000 to 25,000 g / mol and very particularly preferably 12,000 to 22,000 g / mol, in particular 14,000 to 20,000 g / mol.
  • the hydroxy-functional poly (meth) acrylates A1 preferably have one
  • Hydroxyl functionality of 5 to 15, more preferably 6 to 14, most preferably 8 to 12.
  • the hydroxy-functional poly (meth) acrylates A1 can be prepared by means of the
  • the hydroxy-functional poly (meth) acrylates contain A1 in
  • carboxy-functional ethylenically unsaturated monomers and the monomers iii. are each preferably monoethylenically unsaturated.
  • the hydroxyl groups contained in the hydroxy-functional poly (meth) acrylate A1 are hydroxy-functional ethylenically unsaturated monomers, preferably hydroxy-functional acrylic esters and / or hydroxy-functional
  • hydroxy-functional (meth) acrylates are preferably hydroxyethyl methacrylate, hydroxyethyl acrylate,
  • Hydroxypropyl methacrylate and hydroxypropyl acrylate particularly preferred are hydroxyethyl methacrylate and 2-hydroxypropyl methacrylate.
  • the amount of hydroxy-functional ethylenically unsaturated monomers used in the preparation of the hydroxy-functional poly (meth) acrylates A1, preferably hydroxy-functional (meth) acrylates is measured at the target range for the hydroxyl number of 50 to 120 mg KOH / g.
  • the hydroxy-functional poly (meth) acrylates contain alginic amounts of carboxyl groups. These are preferably introduced into the poly (meth) acrylate in the polymerization reaction by using carboxy-functional monomers, particularly preferably by using acrylic acid and / or methacrylic acid.
  • the amount of carboxy-functional monomers used in the preparation of the hydroxy-functional poly (meth) acrylates A1, in particular acrylic acid and / or methacrylic acid, is measured at the target range for the acid number of less than 25 mg KOH / g.
  • unsaturated monomers are also iii. ethylenically unsaturated, in particular monoethylenically unsaturated monomers in the preparation of the
  • hydroxyl group-free and free of carboxyl groups are preferably selected from the group a. the alkyl esters of acrylic acid and / or the
  • Hydrocarbon radical having 1 to 8 carbon atoms, preferably 1 to 6, particularly preferably 1 to 4 carbon atoms or b. the group of non-acrylic and non-methacrylic ethylenically unsaturated, preferably monoethylenically unsaturated monomers.
  • the non-acrylic, non-methacrylic, hydroxyl group- and carboxyl group-free monoethylenically unsaturated monomers are particularly preferably styrenes. Based on the total weight of the ethylenically unsaturated monomers, the proportion of a. hydroxyl-free and carboxyl-free alkyl esters of (meth) acrylic acid total preferably 20 to 45 wt .-%, particularly preferably 25 to 40 wt .-% and most preferably 30 to 35 wt .-%.
  • the proportion of hydroxyl-free and carboxyl-group-free, non-acrylic and non-methacrylic ethylenically unsaturated monomers is preferably 30 to 60% by weight, more preferably 35 to 55% by weight and most preferably 40 to 50 wt .-%.
  • monoethylenically unsaturated monomers may be copolymerized into the hydroxy-functional poly (meth) acrylates A1, which are different from I., ii. and iii. differ.
  • the percentage by weight of such monomers in the total weight of the ethylenically unsaturated monomers used to prepare the hydroxy-functional poly (meth) acrylates is preferably 0 to 10% by weight, particularly preferably 0 to 5% by weight. This is very particularly preferred
  • An example of a monomer iv. is
  • the hydroxy-functional poly (meth) acrylate A1 can be used in an organic solvent, preferably an aprotic solvent.
  • an organic solvent preferably an aprotic solvent.
  • Solvent for this purpose is, for example, n-butyl acetate, which can also be used in the preparation of the hydroxy-functional poly (meth) acrylates.
  • solvent for this purpose, should the hydroxy-functional poly (meth) acrylates A1 be used in a solvent, then the solvent of course does not count as component A1, but is added to the solvent content. This also applies analogously to all constituents of the base lacquer component A and the hardener component B.
  • the coating compositions of the invention contain one or more polyester polyols A2 having a hydroxyl number of 100 to 200 mg KOH / g.
  • the polyester polyols A2 have a hydroxyl number of 110 to 180 mg KOH / g, particularly preferably 120 to 160 mg KOH / g.
  • the number-average molecular weight of the polyesterpolyols A2 is preferably in the range from 800 to 3000 g / mol, more preferably from 1000 to 2000 g / mol, very particularly preferably from 1000 to 1600 g / mol.
  • the number-average molecular weight of the polyesterpolyols A2 is determined in the context of the present invention by gel permeation chromatography using a polystyrene standard according to DIN 55672-1: 2016-03.
  • the polyester polyols A2 are branched.
  • the polyester polyols A2 preferably have a hydroxyl functionality of from 2.2 to 4, more preferably from 2.5 to 3.5, very particularly preferably from 2.7 to 3.3.
  • the acid number of the polyesterpolyols A2 is preferably less than 10 mg KOH / g, more preferably less than 5 mg KOH / g and most preferably less than 3 mg KOH / g, in particular ⁇ 2.5 mg KOH / g, such as 0.2 to 2 mg KOH / g.
  • the species A3 has a structure which can be represented by the following formula (I):
  • R 1 - (C O) r -O- (AO) s R 2 (I) wherein R 1 is a saturated or unsaturated, aliphatic hydrocarbon radical having 6 to 30, preferably 8 to 26, particularly preferably 10 to 24 and very particularly preferably 12 to 24 carbon atoms,
  • R 2 is H, a radical PO (OH) 2 or the optionally partially phosphated radical of a mono- or disaccharide or the optionally partially phosphated radical of an alditol, in particular of sorbitol,
  • the radicals R 1 are preferably acyclic radicals.
  • the radicals AO may be the same or different and be arranged randomly within the s radicals, in a block-like or gradient-like manner.
  • the above-mentioned cases are the radicals other than ethylene oxide propylene oxide radicals.
  • the species of formula (II) are alkoxylated fatty alcohols, preferably ethoxylated fatty alcohols, optionally
  • R 2 is an optionally partially phosphated radical of a mono- or disaccharide or an optionally partially phosphated radical of an alditol.
  • mixtures of the species A3 in which s 0 applies for at least one species and s> 0, preferably 1 to 25 or 2 to 25, particularly preferably 4 to 22 or 6 to 20 and all, for at least one further species particularly preferably 8 to 18 applies.
  • mixtures comprising the abovementioned alkoxylated fatty alcohols with s> 0 and / or the abovementioned alkoxylated fatty acids with s> 0 and comprising at least one further species selected from the group
  • the crosslinking catalyst serves primarily to catalyze the reaction between the free isocyanate groups of the polyisocyanates B1 and the
  • the crosslinking catalyst (s) A4 are selected from the group of bismuth carboxylates.
  • the bismuth carboxylates preferably have the general formula (II)
  • the carboxylate radicals are branched and very particularly preferably have these in alpha position to the carbon atom of the carboxylate group on a tertiary or quaternary, preferably quaternary carbon atom.
  • bismuth carboxylates bismuth trineodecanoate has been found to be particularly suitable.
  • the bismuth carboxylates are preferably used in combination with the carboxylic acid HOOC (C n H 2n + i) on which the carboxyate is based, in which n has the abovementioned meaning.
  • the free carboxylic acid is formally not to be regarded as part of the crosslinking catalyst A4 in the context of this invention, even if it may optionally serve as promoter of catalysis in addition to the stabilizing effect, but is one of the other additives A8 as described below.
  • the coating compositions according to the invention very preferably contain small amounts of polyether-modified alkylpolysiloxanes A5, preferably of polyether-modified methylpolysiloxanes.
  • polyether-modified alkylpolysiloxanes A5 preferably of polyether-modified methylpolysiloxanes.
  • Alkylpolysiloxanes in particular the aforementioned amounts
  • Polyether-modified methylpolysiloxanes based on the solids of the parent lacquer component A, there is an improved effect of the species A3 on the Entformungs Koch, the cured coated fiber-reinforced component from the mold.
  • the combined use of the species A3 and A5 is therefore particularly preferred.
  • the coating compositions according to the invention may be pigmented and / or filled with fillers.
  • fillers In principle, all inorganic and organic pigments and fillers can be used as pigments and fillers.
  • the refractive index is often used to distinguish. If this is above 1, 7, as one usually speaks of pigments, it is below this value of fillers.
  • Typical inorganic pigments are oxide and oxide hydroxide pigments, such as titanium dioxide, in particular rutile, zinc oxide, iron oxide and
  • Chromium oxide, oxide mixed phase pigments such as bismuth-molybdenum-vanadium oxide yellow, chromium titanium yellow, spinel blue, iron manganese brown, zinc iron brown, iron manganese black and spinel black, sulfide and
  • Sulfidselenidpigmente such as zinc sulfide, lithopone, cadmium yellow and Cadmium red, chromate and chromate-molybdenum mixed-phase pigments such as chrome yellow and molybdate orange and red, complex salt pigments such as iron blue, silica clays such as aluminum silicate and ultramarine (blue, violet and red), pigments of chemical elements such as aluminum, Copper-zinc alloys and in particular carbon black, and other pigments, such as barium sulfate.
  • complex salt pigments such as iron blue, silica clays such as aluminum silicate and ultramarine (blue, violet and red)
  • pigments of chemical elements such as aluminum, Copper-zinc alloys and in particular carbon black
  • other pigments such as barium sulfate.
  • Typical organic pigments are monoazo pigments, disazo pigments and polycyclic pigments such as perylene pigments and
  • Phthalocyanine pigments are derived from Phthalocyanine pigments.
  • Typical inorganic fillers are silicates such as talc and kaolin, silicas such as precipitated or fumed silicas, oxides such as aluminum hydroxide or magnesium hydroxide, sulfates such as
  • blanc fixe and calcium sulfate as well as various carbonates.
  • the coating compositions according to the invention may contain additives from the group of wetting agents and / or dispersants, rheology auxiliaries, such as, for example, thickeners and / or thixotropic agents and leveling agents, which are constituents A1 to A6.
  • Wetting and dispersing agents are used in particular when the inventive
  • Coating composition containing one or more pigments A6 and / or fillers A6.
  • Flärter component B comprises polyisocyanates B1 which have an NCO group functionality of greater than 2.4 to 5, preferably 2.6 to 4, especially preferably from 2.8 to 3.6, with the proviso that at least one of the polyisocyanates B1 contains at least one isocyanurate ring and at least one of the polyisocyanates B1 contains at least one iminooxadiazinedione ring.
  • the polyisocyanates B1 are preferably oligomers, preferably trimers or tetramers of diisocyanates. Particularly preferred are Iminooxadiazindione, isocyanurates, allophanates and / or biurets of diisocyanates.
  • the polyisocyanates B1 of the hardener component B are particularly preferably aliphatic and / or cycloaliphatic, very particularly preferably aliphatic polyisocyanates.
  • Isophorone diisocyanate most preferably only hexamethylene diisocyanate as the diisocyanate-based of the above-mentioned oligomers, in particular the tri- or tetramers mentioned above.
  • the hardener component B comprises aliphatic
  • Polyisocyanates B1 based on trimers and / or tetramers of aliphatic diisocyanates, preferably trimers of aliphatic diisocyanates selected from the group consisting of hexamethylene diisocyanate and isophorone diisocyanate, preferably only hexamethylene diisocyanate, wherein a part of the polyisocyanates at least one Iminooxadiazindion structure, and another part of
  • Polyisocyanates contain at least one isocyanurate and optionally at least one allophanate structure.
  • Polyisocyanates B1 can affect the hardness, flexibility and elasticity of the resulting cured coating.
  • Polyisocyanate B1 leads to coatings with particular hardness, which prevents substrate structures from hardening up to
  • Coating surface propagate and there an undesirable ripple occurs.
  • Such polyisocyanates are available, for example, from Covestro under the name Desmodur N3900.
  • Suitable additives A8 or B2 are UV absorbers,
  • additives A8 or B2 are used which are able to reduce or prevent the soiling of the coated foams.
  • Particularly suitable for this purpose are polysiloxanes, in particular alkylpolysiloxanes, the latter preferably bearing one or more hydroxyl groups, particularly preferably 2 to 4 hydroxyl groups, on their alkyl groups.
  • the solvent-based two-component coating composition according to the invention contain as additive alkylpolysiloxanes which contain hydroxyalkyl groups.
  • These additives are preferably in amounts of 0.05 to 1, 5 wt .-%, particularly preferably 0.1 to 1 wt .-% in the inventive
  • the abovementioned additives also facilitate demolding.
  • the coating compositions according to the invention are solvent-based coating compositions.
  • the coating compositions of the invention contain organic solvents as the main solvent.
  • the organic solvents are volatile constituents of the composition according to the invention, which evaporate completely or partially during drying or venting of the wet films produced therefrom. Besides the property of the solvents the components of the
  • these also serve to adjust the viscosity of the coating composition.
  • the proportion of organic solvents based on the total weight of the compositions according to the invention is preferably 40 to 70 wt .-%, particularly preferably 45 to 65 wt .-% and most preferably 50 to 60 wt .-%, in particular 52 to 58 wt. %.
  • Organic solvents which are preferred in the context of the present invention are aprotic. Particular preference is given to polar aprotic organic solvents. Most preferably, the organic solvents behave chemically inert to the remaining constituents of the base paint component A and in particular to the constituents of the curing agent component B.
  • Preferred organic solvents in the context of the present invention are, for example, ketones, such as acetone, methyl ethyl ketone, cyclohexanone,
  • Esters such as ethyl acetate, n-butyl acetate, ethylene glycol diacetate, butyrolactone, diethyl carbonate, propylene carbonate, ethylene carbonate, 2-methoxypropyl acetate (MPA) and ethylethoxypropionate;
  • Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and N-ethylpyrrolidone; Methylal, butyl, 1,3-dioxolane, glycerol formal; and somewhat less preferred because they are nonpolar, hydrocarbons such as benzene, toluene, n-hexane, cyclohexane and solvent naphtha.
  • Very particularly preferred solvents belong to the class of esters,
  • the master paint component A preferably comprises
  • hydroxy-functional poly (meth) acrylates A1 having a hydroxyl number of 50 to 120 mg KOH / g, an acid number of less than 25 mg KOH / g and a number average molecular weight of 4000 to 10,000 g / mol;
  • polyester polyols A2 having a hydroxyl number of 100 to 200 mg KOH / g, an acid number of less than 10 mg KOH / g and a number average molecular weight of 800 to 3000 g / mol;
  • Hydrocarbon radical having 6 to 30 carbon atoms
  • R 2 is H, a radical PO (OH) 2 or the optionally partially phosphated radical of a monosaccharide or the optionally partially phosphated radical of an alditol, AO is one or more alkylene oxide radicals selected from the group consisting of ethylene oxide and propylene oxide,
  • crosslinking catalysts A4 selected from the group of bismuth carboxylates
  • additives A 7 selected from the group consisting of wetting and / or dispersing agents, Rheologieskarn and leveling agents, for the case that one or more pigments A6 and / or one or more fillers A6 in the base paint component A are included ,
  • the parent lacquer component A comprises
  • hydroxy-functional poly (meth) acrylates A1 having a flyroxyl number of 65 to 100 mg KOH / g, an acid number of 1 to 20 mg KOH / g and a number average molecular weight of 5000 to 9000 g / mol;
  • polyesterpolyols A2 having a flythroxyl number of 110 to 180 mg KOFI / g, an acid number of less than 5 mg KOFI / g and a number average molecular weight of 1000 to 2000 g / mol;
  • R 1 - (C O) r -O- (AO) s R 2 (I) wherein R 1 is a saturated or unsaturated, aliphatic
  • Hydrocarbon radical having 10 to 24 carbon atoms
  • R 2 is H, a radical PO (OH) 2 or the optionally partially phosphated radical of a monosaccharide or the optionally partially phosphated radical of an alditol, AO is one or more alkylene oxide radicals selected from the group consisting of ethylene oxide and propylene oxide,
  • crosslinking catalysts A4 selected from the group of bismuth carboxylates of the general formula (II)
  • additives A 7 selected from the group consisting of wetting and / or dispersing agents, Rheologieskarn and leveling agents, for the case that one or more pigments A6 and / or one or more fillers A6 in the base paint component A are included ,
  • the master paint component A comprises
  • hydroxy-functional poly (meth) acrylates A1 having a hydroxyl number of 70 to 95 mg KOH / g, an acid number of 4 to 16 mg KOH / g and a number average molecular weight of 5500 to 8000 g / mol;
  • polyester polyols A2 having a hydroxyl number of 120 to 160 mg KOH / g, an acid number of less than 3 mg KOH / g and a number average molecular weight of 1000 to 1600 g / mol;
  • Hydrocarbon radical having 10 to 24 carbon atoms
  • R 2 is H, a radical PO (OH) 2 or the optionally partially phosphated radical of a monosaccharide or the optionally partially phosphated radical of an alditol, AO is one or more alkylene oxide radicals selected from the group consisting of ethylene oxide and propylene oxide,
  • additives A 7 selected from the group consisting of wetting and / or dispersing agents, Rheologieskarn and leveling agents, for the case that one or more pigments A6 and / or one or more fillers A6 in the base paint component A are included ,
  • the hardener component B comprises
  • one or more aliphatic polyisocyanates B1 which have on average 2.4 to 4, preferably 2.6 to 4 and particularly preferably 2.8 to 3.6 NCO groups and contain at least one isocyanurate ring and ii. one or more aliphatic polyisocyanates B1, which have on average 2.4 to 4, preferably 2.6 to 4 and particularly preferably 2.8 to 3.6 NCO groups and at least one iminooxadiazinedione ring.
  • the Flärter component B comprises the aforementioned
  • Polyisocyanates B1 wherein the isocyanurate ring and the Iminooxadiazindion ring is formed in each case by trimerization of diisocyanates which are selected from the group consisting of flexamethylene diisocyanate and isophorone diisocyanate.
  • the amount of constituents A1 with respect to the sum of the weights of constituents A1 and A2 can likewise vary within wide limits.
  • the proportion of constituents A1 based on the total by weight of constituents A1 and A2 is more than 80% by weight, more preferably more than 85% by weight and less than 98% by weight, very particularly preferably 88 to 96% by weight. -% or 90 to 94 wt .-%.
  • the amount of the components A1 plus A2 is preferably 75 to 95% by weight, more preferably 80 to 90% by weight, and most preferably 82 to 88% by weight.
  • the entirety of the species A3 is preferably in an amount of 1 to 12% by weight, more preferably 2 to 10% by weight, and most preferably in one Amount of 4 to 10 wt .-% based on the solids of the parent lacquer component A included.
  • the crosslinking catalyst or catalysts A4 are preferably used in an amount of 0.3 to 3 wt .-%, particularly preferably 0.5 to 2.5 wt .-%, in particular 0.8 to 2.5 wt .-% based on the Solid body of the base paint component A used.
  • Their content is preferably 0.5 to 6 wt .-%, particularly preferably 1 to 5 wt .-%, most preferably 2 to 4 wt .-% based on the solids of the parent lacquer component A, the two-component coating composition according to the invention ,
  • the content of the two-component coating composition of the invention pigments A6 and / or fillers A6 can in wide
  • Ranges vary.
  • the total content of pigments and / or fillers 0.1 to 10 wt .-%, more preferably 0.2 to 3 wt .-% and most preferably 0.3 to 1, 5 wt .-% based on the solids the
  • the content of the novel two-component coating composition of additives A 7 can likewise vary within wide limits.
  • flow control agents are present in the two-component coating composition according to the invention, their content, based on the solids of the parent coating component A, is preferably from 0.1 to 3% by weight, more preferably from 0.2 to 1.5% by weight and particularly preferably 0.3 to 1 wt .-%.
  • the same amount ranges preferably also apply to the
  • wetting and dispersing agents usually varies in broader ranges, in particular depending on the pigment and / or
  • Filler content and the type of pigments and / or fillers are usually based on the solids
  • Stock paint component A preferably 0.2 to 8 wt .-%, particularly preferably 0.5 to 6% by weight.
  • the total content of additives A 7 based on the solids content of the basecoat component A is preferably 0 to 10% by weight, more preferably 0.1 to 8% by weight and most preferably 0.5 to 5% by weight.
  • the hardener component B preferably contains at least 80% by weight, more preferably at least 90% by weight and most preferably at least 95% by weight, better still 100% by weight of the above-identified polyisocyanates B1.
  • the hardener component may also comprise further di- or polyisocyanates B3 which do not fall under the definition of the polyisocyanates B1, in particular those which have an NCO functionality which is less than 2.4 or greater than 5.
  • the amount of constituents B1 which contain at least one isocyanurate ring and those which contain at least one iminooxadiazinedione ring, relative to the sum of the weights of these two constituents, can likewise vary within wide limits.
  • the proportion of constituents B1 which contain at least one isocyanurate ring is preferably greater than 60% by weight, particularly preferably greater than 70, based on the total by weight of constituents B1 which contain at least one isocyanurate ring plus those which contain at least one iminooxadiazinedione ring Wt .-% and less than 95 wt .-%, most preferably 75 to 90 wt .-% or 80 to 85 wt .-%. If constituents B1 contain both an isocyanurate ring and an iminooxadiazine dione ring, then these, even with regard to their amount used, are formally assigned only to constituents B1 which contain an isocyanurate ring.
  • the optional additives A8 and B2 can, based on the total weight of the two-component coating composition according to the invention in a total amount of 0 to a maximum of 8 wt .-%, preferably at most 5 wt .-%, such as 0.5 to 8 wt .-% or 1 to 5 wt .-% contained.
  • Another object of the present invention is a process for producing coated foams or of components thereof.
  • a component is understood to mean, as usual, an individual part which, connected to other components, forms an assembly. If, for example, the component is the part of a body, for example a motor vehicle, it can be assembled with other body components to form a body. If the component is, for example, a shoe sole, then it can be joined together with other components of a shoe to form a shoe sole. In general, however, the invention is independent of the purpose of the invention
  • the foams include, inter alia, elastomeric foams, in particular flexible foams, but also duroplastic foams, in particular hard foams.
  • the foams can be open-celled, closed-cell or mixed-celled. Also so-called integral foams are counted herein to the foams.
  • Particularly preferred foams are polyurethane foams. These are usually composed of one or more polyols and one or more of
  • Polyol component is usually added to water, which with a part of the
  • polystyrene foams Polyisocyanate with formation of carbon dioxide, and thus reacted with foaming.
  • long-chain polyols soft to elastic foams, in particular soft foams, are obtained.
  • short-chain polyols are used, as a rule strongly cross-linked structures are formed, which as a rule leads to formation of rigid foams leads.
  • the polyols used to make the polyurethane foams preferably include polyester polyols, polyether polyols and / or polyester polyether polyols, and are preferably selected from the group of the aforementioned polyols.
  • the foam formulations can also be admixed with fibers. If such formulations are foamed, so-called fiber-reinforced foams are produced. Fibers are preferably used in the production of rigid foams.
  • the foams are in one
  • RIM Reaction Injection Molding
  • the coating of the foams takes place during the formation of the foams.
  • a surface of a molding tool preferably without the use of an external mold release agent, is coated with the coating composition of the invention, preferably by spraying or spraying, for example pneumatically or electrostatically.
  • the masterbatch component A and the curing agent component B of the two-component coating composition according to the invention are fed via separate feeds to the mold.
  • the parent lacquer component A and the hardener component B in the feed temperatures between 15 and 70 ° C, more preferably 15 to 40 ° C, in particular 20 to 30 ° C.
  • the supply can be done under pressure.
  • the coating agent layer is then flashed off.
  • the flash-off time is preferably less than 2 minutes, more preferably less than 1 minute, and most preferably less than 30 seconds. It is advantageous if the mold has a temperature of 20 to 100 ° C, more preferably 30 to 90 ° C, most preferably 40 to 80 ° C, especially 50 to 70 ° C. has.
  • the dry film thickness is 20 to 120 miti, more preferably 25 to 100 miti.
  • the mold is closed after the application of the coating agent layer and the preferably to be carried out venting, before then the foam formulation
  • Coating composition coated can be removed from the mold.
  • the reaction time usually varies in the range of 1 to 8 minutes, typically 2 to 6 minutes, at a temperature of the mold in the range of preferably 45 to 75 ° C, more preferably 50 to 70 ° C, most preferably 52 to 65 ° C. Then the demoulding takes place.
  • coated foams can be used in many areas. For example, in the interior and exterior of motor vehicles, especially as a seat cushion or fenders, steering wheel, sill or bumper panels, but also as shoe soles, or in the field of furniture and furniture upholstery.
  • the coated component can, if desired, without grinding,
  • Coating agents such as one or more basecoats and one or more clearcoats to form one or more
  • Basecoat films or one or more clearcoat films be coated.
  • no filler layer is applied to the foam coated according to the invention, but directly a basecoat film or a topcoat film, in particular a clearcoat film.
  • Basecoats or clearcoats are used. Such basecoats and clearcoats are available, for example, from BASF Coatings GmbFI, clearcoats of the EverGloss product line in particular having proven particularly useful as clearcoats.
  • Another object of the present invention is the use of
  • A1 hydroxy-functional poly (meth) acrylate having a hydroxyl number of 82.5 mg
  • A4 bismuth neodecanoate
  • B1 a Hexamethylene diisocyanate trimer of the isocyanurate type with a
  • B1 b Iminooxadiazinedione type hexamethylene diisocyanate trimer having an NCO content of 23.5% by weight
  • Example 1 The coating composition of Example 1 was manually pneumatically (SATA Jet 4000 B HVLP with 1, 0 nozzle) applied to the surface of a mold a) in plate form and a mold b) in shoe brolly (the molds each consist of aluminum alloys, plate size: 200 mm x 200 mm x 20 mm, unstructured, shoe sole shape: outsole;
  • the mold temperatures were 55 ° C and 65 ° C respectively (in the case of the plate shape) and 65 ° C in the shoe sole mold.
  • the coating was then flashed off (flash-off time: 20 to 25 s, dry layer thickness: about 80 ⁇ m (light microscopy)).
  • polyester polyol mixture with an OH number of 51 mg KOH / g (BASF Italia SpA)
  • the different foam densities result from different degrees of compression in the mold, which is produced by different amounts of the components at the same mixing ratio.
  • the mixing ratio of the A component to the B component is 100: 86.7 (w / w).
  • Reactint BLUW X17 AB was used as blue pigment paste.
  • Polyurethane foams were made in closed form at 55 ° C and 65 ° C, respectively, over a period of 4 minutes.
  • the coated foam could be removed manually, easily and completely from the tool without any aids.
  • the surface of the coating met the required matting in the shoe industry.
  • the test was carried out 24 hours after the production of the foam. With the crosshatching device, 6 parallel cuts are made at a distance of 2 mm to the substrate. These are then crossed by 6 sections cut at right angles, also at a distance of 2 mm. Subsequently, an adhesive tape is applied and pulled off abruptly at an angle of 60 °.
  • the foam coated according to the invention exhibits, in contrast to an uncoated foam, only a lower uptake of dirt.
  • Example 2 In this example, the paint formulation of Example 1 is used in conjunction with a foam system (from the Elastopan® S series from BASF), which leads to very low density foams (250 g / l).
  • a foam system from the Elastopan® S series from BASF
  • a mold in steering wheel shape consisting of an upper and a lower part was cleaned, tempered to a temperature of 62 to 65 ° C and by means of a spray gun with the coating composition of Example 1, as in Example 1, manually painted (upper and lower part ).
  • a steel ring (the so-called skeleton) was inserted into the mold, which causes additional strength of the steering wheel. Thereafter, the mold was closed and a polyether-based polyurethane foam-forming composition was injected, thereby frothing the skeleton.
  • Example 2 Seconds the mold was opened and the steering wheel demoulded.
  • the cross-cut test was carried out as indicated in Example 1 and surprisingly also gave the excellent cross-cut cutoff value of 0, although in the present case it is the coating of a polyether-based foam, while the coating agent according to the invention is polyester-based.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)

Abstract

La présente invention concerne une composition d'agent de revêtement à deux composants, à base de solvant, qui comprend un composant de laque mère A et un composant durcisseur B, le composant de laque mère A contenant au moins un poly(méth)acrylate à fonctionnalité hydroxy A1, présentant un indice d'hydroxyle de 0 à 120 mg de KOH/g ; au moins un polyester-polyol A2 présentant un indice d'hydroxyle de 100 à 200 mg KOH/g ; au moins une espèce A3 de formule générale R1-(C=O)r-O-(AO)s-R2, dans laquelle R1 représente un radical hydrocarboné saturé ou insaturé, aliphatique, comprenant 6 à 30 atomes de carbone, R2 représente H, un radical PO(OH)2 ou le radical le cas échéant partiellement phosphaté d'un monosaccharide ou d'un disaccharide ou le radical le cas échéant partiellement phosphaté d'un alditol steht, AO représente un ou plusieurs radicaux d'oxyde d'alkylène du groupe constitué par l'oxyde d'éthylène, l'oxyde de propylène et l'oxyde de butylène, r = 0 ou 1 et s = 0 à 30 ; au moins un catalyseur de réticulation A4 choisi dans le groupe des carboxylates de bismuth ; et le composant durcisseur B contenant au moins un polyisocyanate B1, qui présente en moyenne 2,4 à 5 groupes NCO et au moins un cycle isocyanurate et au moins un polyisocyanate B, qui présente en moyenne 2,4 à 5 groupes NCO et qui contient au moins un cycle iminooxadiazinedione. L'invention concerne en outre un procédé pour la préparation de mousses revêtues à l'aide de la composition d'agent de revêtement à deux composants à base de solvant ainsi que son utilisation pour la production de mousses revêtues.
PCT/EP2018/084942 2017-12-21 2018-12-14 Compositions d'agent de revêtement pour le revêtement de mousses dans un procédé dans le moule WO2019121389A1 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112442305A (zh) * 2019-08-29 2021-03-05 江苏宏源机电科技有限公司 一种高固体分涂料及其制备方法
EP3858882A1 (fr) * 2020-02-03 2021-08-04 BASF Coatings GmbH Compositions d'agent de revêtement destinées au revêtement des matières alvéolaires et matériaux composites renforcés par des fibres selon le procédé de finition dans le moule
WO2021156052A1 (fr) * 2020-02-03 2021-08-12 Basf Coatings Gmbh Composition de revêtement sur laquelle un autre revêtement peut être appliqué et procédé de revêtement de substrats faisant appel à de telles compositions

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US20070004892A1 (en) * 2005-07-01 2007-01-04 Rye Karen R Flexible polymer coating and coated flexible substrates

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112442305A (zh) * 2019-08-29 2021-03-05 江苏宏源机电科技有限公司 一种高固体分涂料及其制备方法
EP3858882A1 (fr) * 2020-02-03 2021-08-04 BASF Coatings GmbH Compositions d'agent de revêtement destinées au revêtement des matières alvéolaires et matériaux composites renforcés par des fibres selon le procédé de finition dans le moule
WO2021156052A1 (fr) * 2020-02-03 2021-08-12 Basf Coatings Gmbh Composition de revêtement sur laquelle un autre revêtement peut être appliqué et procédé de revêtement de substrats faisant appel à de telles compositions
JP7447288B2 (ja) 2020-02-03 2024-03-11 ビーエーエスエフ コーティングス ゲゼルシャフト ミット ベシュレンクテル ハフツング 再被覆可能なコーティング組成物及びそのような組成物で基材をコーティングする方法

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