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WO2010112157A1 - Vernis de protection - Google Patents

Vernis de protection Download PDF

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Publication number
WO2010112157A1
WO2010112157A1 PCT/EP2010/001807 EP2010001807W WO2010112157A1 WO 2010112157 A1 WO2010112157 A1 WO 2010112157A1 EP 2010001807 W EP2010001807 W EP 2010001807W WO 2010112157 A1 WO2010112157 A1 WO 2010112157A1
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WO
WIPO (PCT)
Prior art keywords
optionally
groups
isocyanate
component
formula
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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.)
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PCT/EP2010/001807
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German (de)
English (en)
Inventor
Hans-Josef Laas
Thomas Bäker
Markus Mechtel
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Covestro Deutschland AG
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Bayer MaterialScience AG
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Publication of WO2010112157A1 publication Critical patent/WO2010112157A1/fr
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Classifications

    • 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
    • C08G18/288—Compounds containing at least one heteroatom other than oxygen or nitrogen
    • C08G18/289—Compounds containing at least one heteroatom other than oxygen or nitrogen 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
    • C08G18/28—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
    • C08G18/3225—Polyamines
    • C08G18/3253—Polyamines being in latent form
    • C08G18/3256—Reaction products of polyamines with aldehydes or ketones
    • 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
    • C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
    • C08G18/3821—Carboxylic acids; Esters thereof with monohydroxyl 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
    • C08G18/70—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
    • C08G18/778—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur 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
    • C08G18/78—Nitrogen
    • C08G18/7806—Nitrogen containing -N-C=0 groups
    • C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
    • C08G18/7837—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing allophanate 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
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes

Definitions

  • the invention relates to coating compositions with a high solids content based on polyurea polymers and their use as a protective topcoat.
  • Reaction products of aliphatic or cycloaliphatic polyamines with fumaric acid esters and / or maleic esters, so-called polyaspartic esters, are known as formulation constituents for low-solvent or -free two-component (2K) -polyurethane or polyurea lacquers.
  • Coating compositions based on polyaspartic esters have been described for a large number of different applications, for example for vehicle repair and large vehicle painting (eg EP-A 0 470 461, EP-A 0 531 249, EP-A 1 581 575), which and textile coating (eg EP-A 1 277 876) or as a binder for electrical insulating lacquers (eg EP-A 1 199 320).
  • EP-A 0 689 881 describes binder combinations with high solids contents of up to 95% by weight, which consist of polyaspartic esters, polyketimines or -aldimines and preferably aliphatic or cycloaliphatic lacquer polyisocyanates as crosslinking component, for coating steel parts.
  • the present invention therefore relates to coating compositions comprising A) at least one amine of the formula (I)
  • X is an n-valent, isocyanate-inert radical, as obtained by removing the primary amino groups from an organic amine of the molecular weight range 60 to 6000 with n _
  • R 1 and R 2 are identical or different organic radicals having 1 to 18 carbon atoms and n is an integer> 1,
  • the invention also relates to the use of these coating compositions for coating any substrates, in particular as corrosion protection topcoat.
  • the component A) present in the coating compositions of the invention are amines of the formula (I)
  • X is an n-valent, isocyanate-inert radical, as obtained by removing the primary amino groups from an organic amine in the molecular weight range 60 to 6000 with n primary aliphatic and / or cycloaliphatically bonded amino groups, optionally one or more heteroatoms and / or others, opposite I- _ _
  • R 1 and R 2 are identical or different organic radicals having 1 to 18 carbon atoms and n is an integer> 1.
  • R 1 and R 2 have the abovementioned meaning, take place.
  • Suitable amines for the preparation of the polyaspartic esters A) are, for example, di-functional amines, ie. H. those of the formula (II) in which n is 2, such as. B. ethylene diamine, 1, 2-diaminopropane, 1, 4-diaminobutane, l, 5-diamino-2-methylpentane (Dytek A from. DuPont), 1, 6-diaminohexane, 2,5-diamino-2, 5-dimethylhexane, 2,2,4- and / or
  • IPDA amino-3,3,5-trimethyl-5-aminomethylcyclohexane
  • 1,3-diamino-2- and / or 4-methylcyclohexane isopropyl-2,4- and / or 2,6-diaminocyclohexane, l, 3-bis (aminomethyl) cyclohexane, 2,4'- and / or 4,4'-diamino-dicyclohexylmethane, 3,3'-dimethyl-
  • Suitable tri- or higher-functional amines for the preparation of polyaspartic esters A) are those of the formula (II) in which n is an integer> 3, such.
  • Preferred amino component but are those of the formula (II) in which n is 2, in particular aliphatic and / or cycloaliphatic diamines of the abovementioned type.
  • Very particularly preferred amino components for preparing the polyaspartic esters A) are l, 5-diamino-2-methylpentane, 2,4 '- and / or 4,4'-diamino-dicyclo-hexylmethane and / or 3,3'-dimethyl-4,4'-diamino-dicyclohexylmethane.
  • Fumaric acid diesters or maleic diesters of the formula (III) are used in the preparation of the aspartic acid esters or polyaspartic esters A), in which the radicals R 1 and R 2 represent identical or different radicals and organic radicals having 1 to 18, preferably 1 to 9 , particularly preferably 1 to 4, mean carbon atoms.
  • maleic acid esters of formula (III) in which the radicals R 1 and R 2 represent identical or different radicals and are a methyl, ethyl, n-butyl or 2-ethylhexyl radical.
  • Very particularly preferred polyaspartic esters A) are those which have been prepared using diethyl maleate.
  • the preparation of aspartic acid esters or polyaspartic esters A) can be carried out both in solution and solvent-free. In both cases, an equimolar reaction of the amine (II) with the fumaric diester and / or maleic diester (III) is preferably carried out. For a specific variation of performance properties, the equivalence ratio of maleic acid ester and / or fumaric acid ester (III) to _ _ _
  • Amino groups of component (II) of 1, 2: 1 to 1: 2, are varied. If mixtures of aspartic acid esters or polyaspartic esters A) are used in the coating composition according to the invention, the preparation of the polyasparagric esters can be carried out separately or in a reaction vessel. In addition to the amines A), the coating compositions of the invention may optionally contain further components B) containing isocyanate-reactive groups.
  • These compounds B which are referred to in the context of the present invention as polyaldimines or polyketimines, generally have molecular weights of from 112 to 6500, preferably from 140 to 2500, particularly preferably from 140 to 458.
  • the preferred polyaldimines or polyketimines optionally used as component B) include compounds of the formula (V)
  • R 3 and R 4 are the same or different radicals and hydrogen or inert organic radicals, such as.
  • B hydrocarbon radicals having up to 8 carbon atoms, in particular alkyl radicals having 1 to 8 carbon atoms, and wherein the radicals R 3 and R 4 together with the carbon atom can form a 5- or 6-membered cycloaliphatic ring, with the proviso that the Radicals R 3 and R 4 are not simultaneously hydrogen
  • n stands for an integer> 2.
  • aldehydes or ketones which can be used for the preparation of the polyaldimines or polyketimines correspond to the formula (VI)
  • aldehydes for the preparation of the polyaldimines optionally used as component B) are, for example, acetaldehyde, propionaldehyde, n-butyraldehyde, isobutyraldehyde, trimethylacetaldehyde, 2,2-dimethylpropanal, 2-ethylhexanal, 3-cyclohexane-1-carboxaldehyde, hexanal, Heptanal, octanal, valeraldehyde, benzaldehyde, tetrahydrobenzaldehyde, hexahydrobenzaldehyde, propargyl aldehyde, p-tolualdehyde, phenylethanal, 2-methylpentanal, 3-methylpentanal, 4-methylpentanal, sorbald
  • n-butyraldehyde isobutyraldehyde, trimethylacetaldehyde, 2-ethylhexanal and hexahydrobenzaldehyde.
  • Suitable ketones for the preparation of the polyketimines optionally used as component B) are, for example, acetone, methyl ethyl ketone, methyl propyl ketone, methyl isopropyl ketone, methyl butyl ketone, methyl isobutyl ketone, methyl tert-butyl ketone, methyl n-amyl ketone, methyl isoamyl ketone, methyl heptyl ketone, methyl undecyl ketone, di ethyl ketone, ethyl butyl ketone, ethyl amyl ketone, diisopropyl ketone, diisobutyl ketone, cyclohexanone, cyclopentanone, methylcyclohexanone, isophorone, 5-methyl-3-heptanone, 1-phenyl-2-propanone, acetophenone, methyl nonyl ketone,
  • cyclopentanone particularly preferred are cyclopentanone, cyclohexanone, methylcyclopentanone, methylcyclohexanone, 3,3,5-trimethylcyclopentanone, cyclobutanone, methylcyclobutanone, acetone, methyl ethyl ketone, methyl isobutyl ketone.
  • polyamines used for the preparation of the polyaldimines or polyketimines used as component B) in the novel coating compositions are the amines of the general formula (II) already explicitly described above in connection with the preparation of the polyaspartic esters A). in which n is an integer> 2, or any mixtures of such polyamines.
  • Preferred polyamine for the preparation of component B) is 1-amino-3,3,5-trimethyl-5-aminomethylcyclohexane (IPDA).
  • IPDA 1-amino-3,3,5-trimethyl-5-aminomethylcyclohexane
  • the polyaldimines or polyketimines B) are prepared by methods known per se by reacting the starting components while maintaining a stoichiometric ratio of amino groups to aldehyde or keto groups of 1: 1 to 1: 1.5.
  • acidic substances such as p-toluenesulfonic acid, hydrochloric acid, sulfuric acid or aluminum chloride are used.
  • the reaction is generally carried out within the temperature range of 20 to 180 ° C, the reaction optionally using an entraining agent (eg., Toluene, xylene, cyclohexane and octane) to remove the water of reaction, carried out until the calculated amount in water (1 mole of water per mole of primary amino group) is split off or until no more water is split off.
  • an entraining agent eg., Toluene, xylene, cyclohexane and octane
  • the phases are then separated or the entraining agent and, if present, unreacted starting materials are removed by distillation.
  • the products thus obtained can be used without further purification as component B) in the coating compositions according to the invention.
  • suitable compounds _ _ for the coating compositions of the invention suitable compounds _ _
  • polyester polyols are the usual known from polyurethane chemistry polyhydroxyl compounds such.
  • polyester polyols are the usual known from polyurethane chemistry polyhydroxyl compounds such.
  • polyether polyols are the usual known from polyurethane chemistry polyhydroxyl compounds such.
  • polyacrylate polyols are the usual known from polyurethane chemistry polyhydroxyl compounds such.
  • polyester polyols are the usual known from polyurethane chemistry polyhydroxyl compounds such.
  • polyether polyols are the usual known from polyurethane chemistry polyhydroxyl compounds such.
  • polyacrylate polyols are the usual known from polyurethane chemistry polyhydroxyl compounds such.
  • Suitable polyester polyols B) are, for example, those having a mean molecular weight, which can be calculated from functionality and hydroxyl number, of from 200 to 3000, preferably from 250 to 2500, having a hydroxyl group content of from 1 to 21% by weight, preferably from 2 to 18% by weight. %, as can be prepared in a manner known per se by reacting polyhydric alcohols with substancial amounts of polybasic carboxylic acids, corresponding carboxylic acid anhydrides, corresponding polycarboxylic acid esters of lower alcohols or lactones.
  • suitable polyhydric alcohols are especially those of the molecular weight range 62 to 400 such.
  • 1,2-ethanediol, 1,2- and 1,3-propanediol the isomeric butanediols, pentanediols, hexanediols, heptanediols and octanediols, 1,2- and 1,4-cyclohexanediol, 1,4-cyclohexanedimethanol, 4, 4 '- (1-methylethylidene) biscyclohexanol, 1,2,3-propanetriol, 1,1,1-trimethylolethane, 1, 2,6-hexanetriol, 1,1,1-trimethylolpropane, 2,2-bis (hydroxymethyl) -1,3-propanediol or 1,3,5-tris (2-hydroxyethyl) isocyanurate.
  • the acids or acid derivatives used to prepare the polyester polyols B) may be aliphatic, cycloaliphatic and / or heteroaromatic in nature and optionally, for. B. by halogen atoms, substituted and / or unsaturated.
  • suitable acids are, for example, polybasic carboxylic acids in the molecular weight range from 118 to 300 or derivatives thereof, for example succinic, adipic, sebacic, phthalic, isophthalic, trimellitic, phthalic, tetrahydrophthalic, maleic, maleic, dimeric and trimeric fatty acids, terephthalic bis-glykolester.
  • succinic, adipic, sebacic, phthalic, isophthalic, trimellitic, phthalic, tetrahydrophthalic, maleic, maleic, dimeric and trimeric fatty acids, terephthalic bis-glykolester To prepare the polyesterpolyols B) it is also possible to use any
  • Suitable polyester polyols B) are also those as they are in a conventional manner from lactones and simple polyhydric alcohols, such as. As the above exemplified, can be prepared as starter molecules under ring opening. Suitable lactones for the preparation of these polyester polyols are, for example, ⁇ -propiolactone, ⁇ -butyrolactone, ⁇ - and ⁇ -valerolactone, ⁇ -caprolactone, 3,5,5- and 3,3,5-trimethylcaprolactone or any desired mixtures of such lactones. - -
  • the preparation of these lactone is generally carried out in the presence of catalysts such as Lewis or Brönstedt acids, organic tin or titanium compounds at temperatures of 20 to 200 ° C, preferably 50 to 160 ° C.
  • catalysts such as Lewis or Brönstedt acids, organic tin or titanium compounds at temperatures of 20 to 200 ° C, preferably 50 to 160 ° C.
  • Suitable polyether polyols B) are, for example, those having a mean molecular weight, which can be calculated from functionality and hydroxyl number, of 200 to 6000, preferably 250 to 4000, having a hydroxyl group content of 0.6 to 34% by weight, preferably 1 to 27% by weight. -%, as they are accessible in a conventional manner by alkoxylation of suitable starter molecules.
  • any polyhydric alcohols for example those of the molecular weight range 62 to 400, as described above in the preparation of polyester polyols, can be used as starter molecules.
  • Alkylene oxides which are suitable for the alkoxylation reaction are, in particular, ethylene oxide and propylene oxide, which can be used in any desired order or even as a mixture in the alkoxylation reaction.
  • Suitable Polyacrylatpoylole B) are, for example, those of an average of functionality and hydroxyl number calculable molecular weight of 800 to 50,000, preferably from 1000 to 20,000, with a hydroxyl group content of 0.1 to 12% by weight, preferably 1 to 10, as in can be prepared by copolymerization of hydroxyl-containing olefinically unsaturated monomers with hydroxyl-free olefinic monomers.
  • Suitable monomers for preparing the polyacrylate polyols B) are vinyl or vinylidene monomers such as styrene, ⁇ -methylstyrene, o- or p-chlorostyrene, o-, m- or p-methylstyrene, p-tert-butylstyrene, acrylic acid , Acrylonitrile, methacrylonitrile, acrylic and methacrylic acid esters of alcohols having up to 8 carbon atoms, such as.
  • vinyl or vinylidene monomers such as styrene, ⁇ -methylstyrene, o- or p-chlorostyrene, o-, m- or p-methylstyrene, p-tert-butylstyrene, acrylic acid , Acrylonitrile, methacrylonitrile, acrylic and methacrylic acid esters of alcohols having up to 8 carbon atoms, such as.
  • hydroxyalkyl esters of acrylic acid or methacrylic acid having 2 to 4 carbon atoms in the hydroxyalkyl radical such as.
  • rythritol monoacrylate or methacrylate as well as any mixtures of such exemplified monomers.
  • the said isocyanate-reactive components B) may optionally also be used in the form of any desired mixtures.
  • components B) are present in an amount of up to 50% by weight, preferably up to 40% by weight, more preferably up to 30% by weight, based on the total amount of components A) and B). for use.
  • the coating compositions according to the invention contain silane-containing polyisocyanate components.
  • silane-containing polyisocyanates C) are, for example, the reaction products of aliphatic or cycloaliphatic polyisocyanates, such as those described in WO 2003/054049, JP-A 2005 015644 and EP-A 1 273 640.
  • the polyisocyanate component C) used is preferably allophanate polyisocyanates containing silane groups, which are prepared by reacting - -
  • c1) at least one hydroxyurethane and / or hydroxyamide having silane groups obtainable from the reaction of aminosilanes with cyclic carbonates or lactones with a molar excess of c2) of at least one diisocyanate with aliphatic, based on the NCO-reactive groups of component c1); cycloaliphatic, araliphatic and / or aromatically bonded isocyanate groups and optionally subsequent removal of unreacted Diisocyanatüber- shot were obtained.
  • the preparation of such silane-containing allophanate polyisocyanates is not claimed in the context of the present invention.
  • Starting compounds c1) for preparing the silane-containing polyisocyanate component C particularly suitable allophanate polyisocyanates are any reaction products of aminosilanes with cyclic carbonates or lactones.
  • Suitable aminosilanes for preparing the starting compounds c1) are, for example, those of the general formula (VII)
  • R 5 , R 6 and R 7 are the same or different radicals and each represents a saturated or unsaturated, linear or branched, aliphatic or cycloaliphatic radical or an optionally substituted aromatic or araliphatic radical having up to 18 carbon atoms, optionally up to 3 heteroatoms from the series oxygen, sulfur, nitrogen may contain, - -
  • R is hydrogen, a saturated or unsaturated, linear or branched, aliphatic or cycloaliphatic or an optionally substituted aromatic or Araliphatic radical having up to 18 carbon atoms or a radical of the formula
  • Suitable aminosilanes are, for example, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropylmethyldimethoxysilane, 3-aminopropylmethyldiethoxysilane, 3-aminopropylethyldiethoxysilane, 3-aminopropyldimethylethoxysilane, 3-aminopropyldiisopropylethoxysilane, 3-aminopropyltripropoxysilane, 3-aminopropyltri butoxysilane, 3-aminopropylphenyldiethoxysilane, 3-aminopropylphenyldimethoxysilane, 3-aminopropyltris (methoxyethoxyethoxy) silane, 2-aminoisopropyltrimethoxysilane, 4-aminobutyltrimethoxysilane, 4-aminobutyltrimeth
  • Preferred aminosilanes for preparing the starting component cl) are those of the general formula (VII) in which
  • R 5 , R 6 and R 7 are identical or different radicals and each represents a saturated, linear or branched, aliphatic or cycloaliphatic radical having up to 6 carbon atoms, which may optionally contain up to 3 oxygen atoms
  • Y is a linear or branched alkylene radical with 2 to 10 carbon atoms, which may optionally contain up to 2 imino groups (-NH-), and
  • R 8 represents hydrogen, a saturated, linear or branched, aliphatic or cycloaliphatic radical having up to 6 carbon atoms or a radical of the formula
  • Particularly preferred aminosilanes for preparing the starting component c1) are those of the general formula (VII) in which
  • R 5 , R 6 and R 7 each represent alkyl radicals having up to 6 carbon atoms and / or alkoxy radicals which contain up to 3 oxygen atoms, with the dimensional would be that at least one of the radicals R 5 , R 6 and R 7 is such an alkoxy radical,
  • Y is a linear or branched alkylene radical having 3 or 4 carbon atoms
  • R 8 is hydrogen, a methyl radical or a radical of the formula
  • Particularly preferred aminosilanes for preparing the starting component c1) are those of the general formula (VII) in which
  • R 5 , R 6 and R 7 are each methyl, methoxy and / or ethoxy, with the proviso that at least one of R 5 , R 6 and R 7 is a methoxy or ethoxy radical,
  • Y is a propylene radical (-CH 2 -CH 2 -CH 2 -), and R 8 is hydrogen, a methyl radical or a radical of the formula
  • aminosilanes are aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropylmethyldimethoxysilane and / or 3-aminopropylmethyldiethoxysilane.
  • Suitable cyclic carbonates are in particular those having 3 or 4 carbon atoms in the ring, which may optionally also be substituted, such as.
  • Suitable lactones are, for example, those having 3 to 6 carbon atoms in the ring, which may optionally also be substituted, such as.
  • Preferred lactones are ⁇ -propiolactone, ⁇ -butyrolactone, ⁇ -valerolactone, ⁇ -caprolactone and / or ⁇ -caprolactone.
  • the preparation of the starting compounds c1) by reacting the abovementioned amino silanes with the cyclic carbonates or lactones is known per se and can be carried out, for example, by the processes described in SU-A 295764, US Pat. No. 4,104,296, EP-A 0 833 830 or WO 1998 / 018844. In general, while the reactants are reacted at temperatures of 15 to 100 0 C, preferably 20 to 60 0 C in equimolar quantities to react together.
  • one of the components for example the aminosilane or the cyclic carbonate or lactone, is used in a molar excess amount, but preferably in an excess of not more than 10 mol%, particularly preferably not more than 5 mol% ,
  • available hydroxyflinktionellen starting compounds cl) containing urethane groups when using cyclic carbonates, amide groups when using lactones, are generally colorless low-viscosity liquids.
  • Suitable starting compounds c2) for the process according to the invention are any diisocyanates having aliphatically, cycloaliphatically, araliphatically and / or aromatically bound isocyanate groups which can be prepared by any desired method, for example by using B. by phosgenation or phosgene-free way, for example by urethane cleavage can be produced.
  • Suitable starting diisocyanates are for example those of the molecular weight range 140 to 400 g / mol, such as. B.
  • Preferred starting components c2) are the diisocyanates mentioned with aliphatically and / or cycloaliphatically bonded isocyanate groups.
  • Particularly preferred starting components c2) for the process according to the invention are 1, 6-diisocyanatohexane, 1-isocyanato-S ⁇ - trimethyl-S-isocyanatomethylcyclo-hexane, 2,4'- and / or 4,4'-diisocyanatodicyclohexylmethane or any mixtures thereof diisocyanates.
  • the hydroxyurethanes and / or hydroxyamides cl) containing silane groups are reacted with the diisocyanates c2) at from 40 to 200 ° C., preferably from 60 to 180 ° C., while maintaining an equivalent Ratio of isocyanate groups to isocyanate-reactive groups of from 4: 1 to 50: 1, preferably from 5: 1 to 30: 1, converted to allophanate polyisocyanates.
  • the urethane groups already present herein include "urea groups reactive in addition to isocyanate groups" in addition to the hydroxyl groups of component cl) and the urethane groups intermediately formed therefrom by NCO / OH reaction, since these are also present under the reaction conditions react to allophanate groups.
  • the preparation of the allophanate polyisocyanates containing silane groups can be carried out uncalcalyzed as thermally induced allophanatization.
  • suitable catalysts are preferably used to accelerate the allophanatization reaction.
  • These are the customary known allophanatization catalysts, for example metal carboxylates, metal chelates or tertiary amines of the type described in GB-A 0 994 890, alkylating agents of the type described in US Pat. No. 3,769,318 or strong acids, as described by way of example in EP-A-0 000 194.
  • Suitable allophanatization catalysts are, in particular, zinc compounds, such as, for example, zinc (II) stearate, zinc (II) n-octanoate, zinc (II) 2-ethyl-1-hexanoate, zinc (II) naphthenate or zinc (II) acetylacetonate, tin compounds, such as.
  • zinc compounds such as, for example, zinc (II) stearate, zinc (II) n-octanoate, zinc (II) 2-ethyl-1-hexanoate, zinc (II) naphthenate or zinc (II) acetylacetonate, tin compounds, such as.
  • Suitable, albeit less preferred, catalysts for preparing the alanphanate polyisocyanates containing silane groups which are particularly suitable as the polyisocyanate component C) are also those compounds which, in addition to the allophanatization reaction, also catalyze the trimerization of isocyanate groups to form isocyanurate structures.
  • Such catalysts are described, for example, in EP-A 0 649 866 page 4, line 7 to page 5, line 15.
  • Preferred catalysts are zinc and / or zirconium compounds of the abovementioned type. Very particular preference is given to using zinc (II) n-octanoate, zinc (II) 2-ethyl-1-hexanoate and / or zinc (II) stearate, zirconium (IV) n-octanoate, zirconium (IV) 2-ethyl-l-hexanoate and / or zirconium (IV) neodecanoate.
  • These catalysts are used in the preparation of the polyisocyanate component C) particularly suitable silane-containing AUophanatpolyisocyanate, if any, in an amount of 0.001 to 5 wt .-%, preferably 0.005 to 1 wt .-%, based on the total weight of the reactants cl) and c2) and can be added to the reaction both before the beginning of the reaction and at any time.
  • the preparation of the silane-containing AUophanatpolyisocyanate is preferably carried out solvent-free.
  • suitable solvents which are inert to the reactive groups of the starting components can also be used.
  • Suitable solvents are, for example, the known conventional lacquer solvents, such as.
  • the starting diisocyanate c2) or a mixture of different starting diisocyanates if appropriate under an inert gas, such as _ _
  • the hydroxy-functional starting compound cl) is added in the amount indicated above and, if appropriate, the reaction temperature for the urethanization by a suitable measure (heating or cooling) to a temperature of 30 to 120 ° C, preferably set from 50 to 100 ° C.
  • a suitable measure heating or cooling
  • the allophanatization can be carried out, for example, without addition of a catalyst by heating the reaction mixture to a temperature of from 140 to 200 ° C are started.
  • useful catalysts of the above kind are for accelerating the allophanatization reaction was used, and depending on the type and amount of catalyst used, temperatures in the range of 60 to 140 0 C, preferably 80 to 120 ° C, are sufficient.
  • the catalyst which may be used is admixed either with the silane component c1) and / or with the diisocyanate component c2) before the actual reaction is initiated. In this case, the intermediately forming and, when using hydroxyurethanes c1) in these urethane groups already present, spontaneously react further to the desired allophanate structure.
  • the catalyst optionally containing starting diisocyanates c2) optionally under inert gas, such as nitrogen, and optionally in the presence of a suitable solvent of the type mentioned, usually at optimal for the allophanatization temperatures in the range of 60 to 140 ° C, preferably 80 to 120 ° C, and reacted with the optionally containing the catalyst silane component cl).
  • the course of the reaction of cl) with c2) can be replaced by z. B. titrimetric determination of the NCO content be followed.
  • the reaction is stopped. This can be done by cooling the reaction mixture to room temperature in purely thermal reaction, for example.
  • suitable catalyst poisons for example acid chlorides such as benzoyl chloride or isophthaloyl dichloride.
  • the reaction mixture is then by thin film distillation under reduced pressure, for example at a pressure of less than 10 mbar, preferably below 3 mbar, more preferably below 1 mbar, under as gentle conditions as possible, for example at a temperature of 100 to 200 ° C, preferably from 120 up to 180 ° C, of volatiles (excess monomeric Diisocyana- th, optionally in the preparation of the starting compounds A) used in excess cyclic carbonates or lactones, optionally with solvents used and, in the absence of the use of a catalyst poison, optionally active catalyst).
  • volatiles excess monomeric Diisocyana- th, optionally in the preparation of the starting compounds A
  • solvents optionally with solvents used and, in the absence of the use of a catalyst poison, optionally active catalyst
  • the resulting distillates which in addition to the unreacted monomeric starting diisocyanates c2), optionally excessively used cyclic carbonates or lactones c2) and optionally used solvents and waiving the use of a catalyst poison optionally active catalyst, can be used without problems for re-oligomerization.
  • the volatile constituents mentioned are obtained by extraction with suitable isocyanate-inert solvents, - -
  • aliphatic or cycloaliphatic hydrocarbons such as pentane, hexane, heptane, cyclopentane or cyclohexane separated from the oligomerization.
  • the polyisocyanate component C) which is obtained is particularly suitable silane-containing allophanate polyisocyanates in the form of clear, virtually colorless resins, which as a rule have color numbers of less than 200 APHA, preferably less than 100 APHA, more preferably less than 100 below 80 APHA, an average NCO functionality of 2.0 to 5.0, preferably 2.4 to 4.8, more preferably 3.0 to 4.5, and an NCO content of 6.0 to 20.5 Wt .-%, preferably 10.0 to 18.0 wt .-%, particularly preferably 12.0 to 17.0 wt .-%, have.
  • the coating compositions of the invention may optionally contain organic solvents D) and / or further auxiliaries and additives E).
  • Suitable solvents D) are, for example, the abovementioned conventional inert lacquer solvents which are optionally used in the preparation of the alanphanate polyisocyanates containing silane groups which are particularly suitable as polyisocyanate component C). If appropriate, such coating solvents are used in the coating compositions according to the invention in an amount of up to 50%, preferably up to 30%, particularly preferably up to 10%, based on the total amount of components A) to E).
  • auxiliaries and additives E for example, curing catalysts, fillers, dyes, pigments, matting agents, flame retardants, hydrolysis stabilizers, microbicides, algicides, flow control agents, antioxidants, light stabilizers, water scavengers, thixotropic agents, wetting agents or deaerating agents can be used.
  • These auxiliaries and additives E) are mixed into the components A), B) and / or C) depending on the requirements of the problems to be solved by the application of the coating and their compatibility.
  • Hydrous or strongly alkaline reacting additives should, for example, not the polyisocyanate component C) but the amine A) and / or optionally component B) are admixed.
  • Suitable curing catalysts E) for the coating compositions according to the invention are, for example, the compounds known from polyurethane chemistry for accelerating isocyanate reactions, such as. B. the known tin or bismuth compounds and tertiary amines, as described for example in "Plastics Handbook 7, polyurethanes” Carl Hanser Verlag, Kunststoff - Vienna, 1984, pp 97-98, in more detail.
  • Such catalysts may be used, if at all, in amounts of up to 2% by weight, based on the weight of the binder consisting of the individual components A), optionally B) and C).
  • Suitable fillers are, for example, stone or plastic granules, glass beads, sand or cork, which can optionally be used in amounts of up to 100% by weight, based on the binder mixture consisting of the individual components A), optionally B) and C).
  • pigments examples include titanium dioxide, zinc oxide, iron oxides, chromium oxides or carbon blacks.
  • a detailed overview of pigments for paints are the "textbook of paints and coatings, Volume II, pigments, fillers, dyes", Kittel, Verlag WA Colomb in Heenemann GmbH, Berlin-Oberschwandorf, 1974, p 17-265.
  • the pigments mentioned by way of example may be used, if at all, in amounts of up to 100% by weight, based on the binder mixture consisting of the individual components A), if appropriate B) and C).
  • Matting agents, flame retardants, hydrolysis stabilizers, microbicides, algicides, leveling agents, antioxidants, light stabilizers, water scavengers, thixotropic agents, wetting agents or deaerating agents are also useful in the novel coating compositions as auxiliary agents and additives E), for example in "Lehrbuch der Lacke und Be harshungen, Band III. , Solvents, Plasticizers, Additives, Intermediates ", H. Kittel, Verlag WA Colomb in Heenemann GmbH, Berlin-Oberschwandorf, 1976, pp. 237-398.
  • Desiccants acting as water scavengers are described in more detail, for example, in "Kunststoff Handbuch 7, Polyurethane", Carl-Hanser-Verlag, Kunststoff-Vienna, 1983, p.
  • the total amount of such other auxiliaries and additives is generally up to 25 wt .-%, based on the consisting of the individual components A), optionally B) and C) binder. - -
  • the novel coating compositions are prepared by mixing the individual components A), C) and optionally B), D) and E), for example using the known dissolvers or vacuum dissolvers, which are often preferred in order to achieve extensive degassing of the coating compositions.
  • components B) containing isocyanate-reactive groups it is generally useful to prepare them in a first step with the polyamines A) and, if appropriate, further solvents D) and, if appropriate, further auxiliaries and additives E) to give a storage-stable binder component and the polyisocyanate component C), which may also optionally contain solvent D) and optionally further auxiliaries and additives E), as is customary in two-component systems, to add immediately before application.
  • the quantitative ratio of the components A), optionally B) and C) is selected so that each isocyanate-reactive group of the components A) and optionally B) 0.7 to 2.0, preferably 0.8 to 1.6, particularly preferably 0.9 to 1.4 isocyanate groups of component C) are omitted.
  • novel coating compositions can be prepared by conventional methods, for example by spraying, brushing, dipping, flooding or by means of rollers or squeegees on any substrates, such as.
  • any substrates such as.
  • metals, plastics, wood or glass one or more layers apply.
  • the lower proportion of required, if necessary, to be used organic solvent D) allows it to apply thick layers bubble-free in one operation.
  • the coating compositions according to the invention cure even at low temperatures, for example within the temperature range from -20 to + 60 ° C., preferably from -10 to + 40 ° C., to give light-stable and weather-resistant coating films which are characterized by high hardness and abrasion resistance combined with high Distinguish elasticity.
  • they can of course also be baked at relatively high temperatures, for example up to 14O 0 C.
  • the coating compositions according to the invention are particularly suitable for the production of coatings, in particular as anticorrosive coatings, on metallic materials such as are used, for example, in the production of vehicle bodies, machines, lining panels, drums or containers. - -
  • the substrates to be coated can be provided with suitable primers before the application of the inventive coating compositions. Due to their excellent direct adhesion to critical for conventional polyaspartic acid metallic substrates such. As zinc, aluminum or cold-rolled steel, can be dispensed with loss of quality but also on the co-use of a primer layer when using the inventive coating. In combination with the high layer thickness which can be applied in one operation, this means for the user of the coating composition according to the invention a significant reduction of the coating times and thus a noticeable increase in productivity.
  • the present invention therefore also relates to the use of the novel coating compositions for coating substrates, in particular the use for the direct coating of metallic substrates and the use of the coating compositions as corrosion protection coating. Consequently, therefore, the films obtained from the coating compositions according to the invention and substrates coated therewith are also the subject of the present invention.
  • NCO contents were determined in accordance with DIN EN ISO 11909. All viscosity measurements were carried out using a Physica MCR 51 rheometer manufactured by Anton Paar Germany GmbH (Ostrachdern) in accordance with DIN EN ISO 3219.
  • the Hazen color numbers were determined on a LICO 400 colorimeter from Hach Lange GmbH, Dusseldorf.
  • Polyaspartic esters prepared in accordance with EP-B 0403921 (polyaspartic D)) by reaction of 2 mol of diethyl maleate with 1 mole of 3,3'-dimethyl-4,4'-diamino-dicyclohexyl methane (Laromin C 260 ® Fa. BASF).
  • Viscosity approx. 10000 mPas
  • Equivalent weight 290 g / val
  • Viscosity approx. 10000 mPas
  • Polyaldimine prepared according to DE-A 2 325 824 by reacting 3 mol of isobutyric aldehyde with 1 mol of 1-amino-3,3,5-trimethyl-5-aminomethylcyclohexane (IPDA) and subsequent work-up by distillation of the reaction mixture.
  • Viscosity approx. 30 mPas
  • Isocyanurate group-containing HDI polyisocyanate prepared on the basis of Example 11 of EP-A 0 330 966, with the modification that 2-ethylhexanol instead of 2-ethyl-1,3-hexanediol was used as the catalyst solvent.
  • an amino-functional binder component was prepared by predischarging for 10 minutes with the aid of a dissolver and subsequent grinding on a bead mill with cooling in the proportions indicated there. - -
  • an amino-functional binder component was prepared by predischarging for 10 minutes with the aid of a dissolver and subsequent grinding on a bead mill with cooling in the proportions indicated there.
  • silane-free comparative polyisocyanate V 22.43 parts by weight of the silane-free comparative polyisocyanate V), likewise corresponding to an equivalent ratio of isocyanate groups to isocyanate-reactive groups of 1.1: 1, were added in a second coating batch of the same binder component and likewise incorporated well.
  • the two paints formulated in this way were applied to a degreased aluminum sheet and to cold-rolled steel with the aid of an airless spray coating in a wet film thickness of about 120 ⁇ m and at room temperature (about 23 ° C.) and a relative atmospheric humidity of approx. 50% cured.
  • the drying times according to DEN 53 150 were comparable with Tl about 80 min and T6 about 4 hours.
  • the pot lives of the coating compositions were about 6 hours in both cases.
  • Table 4 shows the results of cross hatch tests according to ISO 2409. Thereafter, the inventive, crosslinked with a silane-containing polyisocyanate coating has both aluminum and cold rolled steel compared to a conventional, d. H. with a silane group-free polyisocyanate crosslinked system improved adhesion.

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Abstract

L'invention porte sur une composition de revêtement ayant une teneur élevée en extrait sec, à base de polymères de type polyurée, ainsi que sur leur utilisation en tant que vernis de couverture de protection.
PCT/EP2010/001807 2009-04-03 2010-03-23 Vernis de protection Ceased WO2010112157A1 (fr)

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* Cited by examiner, † Cited by third party
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CN102250343A (zh) * 2011-05-05 2011-11-23 西安交通大学 一种采用负载型碱金属氟化物催化合成聚天冬氨酸酯的方法
WO2014123962A1 (fr) * 2013-02-05 2014-08-14 Air Products And Chemicals, Inc. Revêtement de polyurée à teneur élevée en matières solides, à faible brillance
WO2014138052A1 (fr) 2013-03-06 2014-09-12 Axalta Coating Systems IP Co. LLC Composition de revêtement à deux composants
EP2862957A1 (fr) 2013-10-16 2015-04-22 Coatings Foreign IP Co. LLC Procédé de production de revêtement multicouche
US9631281B2 (en) 2014-12-04 2017-04-25 Axalta Coating Systems Ip Co., Llc Processes for producing a multilayer coating
US20210102064A1 (en) 2019-10-07 2021-04-08 Covestro Llc Faster cure polyaspartic resins for faster physical property development in coatings
EP4198094A1 (fr) 2021-12-20 2023-06-21 Covestro Deutschland AG Structure multicouche sur supports métalliques à base de revêtements polyaspartate
CN117795023A (zh) * 2021-08-17 2024-03-29 赢创运营有限公司 从聚天冬氨酸酯和2-取代丁二酸酯得到的聚脲组合物

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EP3061779B2 (fr) 2015-02-27 2022-01-05 Mipa Se Agent de revêtement et son utilisation, en particulier destiné à former un revêtement de protection sur une surface
DE102020005446A1 (de) 2020-09-07 2022-03-10 Mankiewicz Gebr. & Co. (Gmbh & Co. Kg) Verbesserte Spachtelmassen und Verfahren zur Beschichtung großer Bauteile

Citations (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU295764A1 (ru) Л. П. Вахрушев, Э. В. Серебренникова , Н. В. Комаров СПОСОБ ПОЛУЧЕНИЯ КРЕМНКЙСОДЕРЖАЩИХ ГЛ И КОЛ ЬКАРБАМАТОВРСЕОСЮЗНА:ХЙЙ^Е1чл-rt.
GB994890A (en) 1961-12-18 1965-06-10 Ici Ltd New organic polyisocyanates and their manufacture
US3769318A (en) 1970-02-27 1973-10-30 Bayer Ag Process for the production of allophanate polyisocyanates
DE2325824A1 (de) 1973-05-22 1974-12-19 Veba Chemie Ag Polyurethan-zweikomponentenlacke
US4104296A (en) 1970-09-28 1978-08-01 Union Carbide Corporation Organofunctional silicon compounds
EP0000194A1 (fr) 1977-07-02 1979-01-10 Bayer Ag Procédé de préparation d'allophanates substitués par des groupements isocyanates et utilisation des allophanates pour la fabrication de vernis
EP0330966A2 (fr) 1988-02-27 1989-09-06 Bayer Ag Procédé de préparation de polyisocyanates contenant des groupes d'isocyanurate
EP0403921A2 (fr) 1989-06-23 1990-12-27 Bayer Ag Procédé pour la préparation de revêtements
EP0470461A2 (fr) 1990-08-10 1992-02-12 Bayer Ag Utilisation de combinaisons de liants à deux composants pour lacques de réparation pour véhicules
EP0531249A1 (fr) 1991-09-04 1993-03-10 Basf Corporation Nouvelle composition de revêtement durcissant dans des conditions ambiantes
EP0596360A1 (fr) 1992-11-06 1994-05-11 Bayer Ag Composés d'alcoxysilanes contenant des groupes amino
EP0649866A1 (fr) 1993-10-20 1995-04-26 Bayer Ag Polyisocyanates pour vernis et leur utilisation
EP0689881A1 (fr) 1994-05-05 1996-01-03 Bayer Ag Procédé de fabrication des couches
EP0816326A1 (fr) 1996-07-02 1998-01-07 Bayer Ag Procédé de préparation d'esters d'acide mono- ou polyaspartique
EP0833830A1 (fr) 1995-06-02 1998-04-08 Minnesota Mining And Manufacturing Company Alcoxysilane ayant des fonctions hydroxy et polyurethane a fonctions alcoxysilane fabrique a partir de cet alcoxysilane
WO1998018844A1 (fr) 1996-10-31 1998-05-07 Minnesota Mining And Manufacturing Company Produits d'etancheite a base de poly(ether-urethanne) fonctionnalise par hydroxycarbamoylalcoxysilane
EP1199320A1 (fr) 2000-10-17 2002-04-24 Bayer Ag Liant pour revêtement d'isolation électrique ayant des structures urée et/ou hydantoine
WO2002058569A1 (fr) 2001-01-24 2002-08-01 Bayer Aktiengesellschaft Enveloppe protectrice ayant une structure de revetement a deux couches
EP1273640A2 (fr) 2001-07-06 2003-01-08 Degussa AG Revêtement non aqueux thermodurcissable à deux composants
EP1277876A2 (fr) 2001-07-19 2003-01-22 Bayer Ag Utilisation d'un durcissant pour des systèmes de polyuréthane à deux composants pour revêtir des substrats flexibles
WO2003054049A1 (fr) 2001-12-20 2003-07-03 Henkel Kommanditgesellschaft Auf Aktien Promoteurs d'adherence pour polyurethanes reactifs
EP0994139B1 (fr) 1998-10-14 2004-04-28 Bayer MaterialScience AG Composées durcissables à l'humidité contenant des groupements ioscyanate et alcoxysilane
JP2005015644A (ja) 2003-06-26 2005-01-20 Yokohama Rubber Co Ltd:The 新規化合物およびそれを含有する硬化性樹脂組成物
EP1581575A1 (fr) 2003-01-03 2005-10-05 E.I. du Pont de Nemours and Company Preparations de revetement durables contenant des composes aspartiques
EP2014692A2 (fr) 2007-07-13 2009-01-14 Bayer MaterialScience AG Groupes d'allophanate et de silane contenant des polyisocyanates

Patent Citations (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU295764A1 (ru) Л. П. Вахрушев, Э. В. Серебренникова , Н. В. Комаров СПОСОБ ПОЛУЧЕНИЯ КРЕМНКЙСОДЕРЖАЩИХ ГЛ И КОЛ ЬКАРБАМАТОВРСЕОСЮЗНА:ХЙЙ^Е1чл-rt.
GB994890A (en) 1961-12-18 1965-06-10 Ici Ltd New organic polyisocyanates and their manufacture
US3769318A (en) 1970-02-27 1973-10-30 Bayer Ag Process for the production of allophanate polyisocyanates
US4104296A (en) 1970-09-28 1978-08-01 Union Carbide Corporation Organofunctional silicon compounds
DE2325824A1 (de) 1973-05-22 1974-12-19 Veba Chemie Ag Polyurethan-zweikomponentenlacke
EP0000194A1 (fr) 1977-07-02 1979-01-10 Bayer Ag Procédé de préparation d'allophanates substitués par des groupements isocyanates et utilisation des allophanates pour la fabrication de vernis
EP0330966A2 (fr) 1988-02-27 1989-09-06 Bayer Ag Procédé de préparation de polyisocyanates contenant des groupes d'isocyanurate
EP0403921A2 (fr) 1989-06-23 1990-12-27 Bayer Ag Procédé pour la préparation de revêtements
EP0403921B1 (fr) 1989-06-23 1994-11-02 Bayer Ag Procédé pour la préparation de revêtements
EP0470461A2 (fr) 1990-08-10 1992-02-12 Bayer Ag Utilisation de combinaisons de liants à deux composants pour lacques de réparation pour véhicules
EP0531249A1 (fr) 1991-09-04 1993-03-10 Basf Corporation Nouvelle composition de revêtement durcissant dans des conditions ambiantes
EP0596360A1 (fr) 1992-11-06 1994-05-11 Bayer Ag Composés d'alcoxysilanes contenant des groupes amino
EP0649866A1 (fr) 1993-10-20 1995-04-26 Bayer Ag Polyisocyanates pour vernis et leur utilisation
EP0689881A1 (fr) 1994-05-05 1996-01-03 Bayer Ag Procédé de fabrication des couches
EP0833830A1 (fr) 1995-06-02 1998-04-08 Minnesota Mining And Manufacturing Company Alcoxysilane ayant des fonctions hydroxy et polyurethane a fonctions alcoxysilane fabrique a partir de cet alcoxysilane
EP0816326A1 (fr) 1996-07-02 1998-01-07 Bayer Ag Procédé de préparation d'esters d'acide mono- ou polyaspartique
WO1998018844A1 (fr) 1996-10-31 1998-05-07 Minnesota Mining And Manufacturing Company Produits d'etancheite a base de poly(ether-urethanne) fonctionnalise par hydroxycarbamoylalcoxysilane
EP0994139B1 (fr) 1998-10-14 2004-04-28 Bayer MaterialScience AG Composées durcissables à l'humidité contenant des groupements ioscyanate et alcoxysilane
EP1199320A1 (fr) 2000-10-17 2002-04-24 Bayer Ag Liant pour revêtement d'isolation électrique ayant des structures urée et/ou hydantoine
WO2002058569A1 (fr) 2001-01-24 2002-08-01 Bayer Aktiengesellschaft Enveloppe protectrice ayant une structure de revetement a deux couches
EP1273640A2 (fr) 2001-07-06 2003-01-08 Degussa AG Revêtement non aqueux thermodurcissable à deux composants
EP1277876A2 (fr) 2001-07-19 2003-01-22 Bayer Ag Utilisation d'un durcissant pour des systèmes de polyuréthane à deux composants pour revêtir des substrats flexibles
WO2003054049A1 (fr) 2001-12-20 2003-07-03 Henkel Kommanditgesellschaft Auf Aktien Promoteurs d'adherence pour polyurethanes reactifs
EP1581575A1 (fr) 2003-01-03 2005-10-05 E.I. du Pont de Nemours and Company Preparations de revetement durables contenant des composes aspartiques
JP2005015644A (ja) 2003-06-26 2005-01-20 Yokohama Rubber Co Ltd:The 新規化合物およびそれを含有する硬化性樹脂組成物
EP2014692A2 (fr) 2007-07-13 2009-01-14 Bayer MaterialScience AG Groupes d'allophanate et de silane contenant des polyisocyanates

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
"Kunststoff Handbuch 7, Polyurethane", 1983, CARL-HANSER-VERLAG, pages: 545
"Kunststoff Handbuch 7, Polyurethane", 1984, CARL-HANSER-VERLAG, pages: 97 - 98
H. KITTEL: "Lehrbuch der Lacke und Beschichtungen, Band III., Lösemittel, Weichmacher, Additive, Zwischenprodukte", 1976, pages: 237 - 398
JUSTUS LIEBIGS ANNALEN DER CHEMIE B, vol. 562, 1949, pages 75 - 136
KITTEL: "Lehrbuch der Lacke und Beschichtungen, Band II, Pigmente, Füllstoffe, Farbstoffe", 1974, VERLAG W.A. COLOMB IN DER HEENEMANN GMBH, pages: 17 - 265

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Publication number Priority date Publication date Assignee Title
CN102250343A (zh) * 2011-05-05 2011-11-23 西安交通大学 一种采用负载型碱金属氟化物催化合成聚天冬氨酸酯的方法
CN102250343B (zh) * 2011-05-05 2012-11-28 西安交通大学 一种采用负载型碱金属氟化物催化合成聚天冬氨酸酯的方法
WO2014123962A1 (fr) * 2013-02-05 2014-08-14 Air Products And Chemicals, Inc. Revêtement de polyurée à teneur élevée en matières solides, à faible brillance
US10683424B2 (en) 2013-02-05 2020-06-16 Evonik Operations Gmbh Low gloss, high solids polyurea coatings
WO2014138052A1 (fr) 2013-03-06 2014-09-12 Axalta Coating Systems IP Co. LLC Composition de revêtement à deux composants
EP2862957A1 (fr) 2013-10-16 2015-04-22 Coatings Foreign IP Co. LLC Procédé de production de revêtement multicouche
US9631281B2 (en) 2014-12-04 2017-04-25 Axalta Coating Systems Ip Co., Llc Processes for producing a multilayer coating
US20210102064A1 (en) 2019-10-07 2021-04-08 Covestro Llc Faster cure polyaspartic resins for faster physical property development in coatings
US11827788B2 (en) 2019-10-07 2023-11-28 Covestro Llc Faster cure polyaspartic resins for faster physical property development in coatings
CN117795023A (zh) * 2021-08-17 2024-03-29 赢创运营有限公司 从聚天冬氨酸酯和2-取代丁二酸酯得到的聚脲组合物
EP4198094A1 (fr) 2021-12-20 2023-06-21 Covestro Deutschland AG Structure multicouche sur supports métalliques à base de revêtements polyaspartate
WO2023117614A1 (fr) 2021-12-20 2023-06-29 Covestro Deutschland Ag Structure multicouche sur des substrats métalliques à base de revêtements de polyaspartate

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