Classifications

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  • 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
  • C08G18/284—Compounds containing ester groups, e.g. oxyalkylated monocarboxylic acids
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  • 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
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  • C08G18/2805—Compounds having only one group containing active hydrogen
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  • C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
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  • 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
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  • 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
  • C08G18/3271—Hydroxyamines
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  • 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
  • C08G18/3271—Hydroxyamines
  • C08G18/3275—Hydroxyamines containing two hydroxy groups
• • C—CHEMISTRY; METALLURGY
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  • 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
  • C08G18/3271—Hydroxyamines
  • C08G18/3278—Hydroxyamines containing at least three hydroxy groups
• • C—CHEMISTRY; METALLURGY
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  • 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
  • C08G18/3842—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring
  • C08G18/3851—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring containing three nitrogen atoms in the ring
  • C08G18/3853—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring containing three nitrogen atoms in the ring containing cyanurate and/or isocyanurate groups
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/40—High-molecular-weight compounds
  • C08G18/48—Polyethers
  • C08G18/4825—Polyethers containing two hydroxy groups
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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  • 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
  • C08G18/67—Unsaturated compounds having active hydrogen
  • C08G18/671—Unsaturated compounds having only one group containing active hydrogen
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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  • 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
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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  • 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
  • C08G18/794—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aromatic isocyanates or isothiocyanates
• • 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
  • C08G18/80—Masked polyisocyanates
• • 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
  • C08G18/80—Masked polyisocyanates
  • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
  • C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing 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
  • C08G18/80—Masked polyisocyanates
  • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
  • C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
  • C08G18/8074—Lactams
• • 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
  • C08G18/80—Masked polyisocyanates
  • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
  • C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
  • C08G18/8077—Oximes
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
  • C09B67/0084—Dispersions of dyes
  • C09B67/0085—Non common dispersing agents
  • C09B67/009—Non common dispersing agents polymeric dispersing agent
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
  • C09D175/04—Polyurethanes
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
  • C09K23/16—Amines or polyamines
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
  • Y10T428/00—Stock material or miscellaneous articles
  • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
  • Y10T428/2913—Rod, strand, filament or fiber
  • Y10T428/2933—Coated or with bond, impregnation or core
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
  • Y10T428/00—Stock material or miscellaneous articles
  • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
  • Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
  • Y10T428/2991—Coated

Definitions

• the present invention relates to wetting agents, dispersants and addition stabilizers suitable as dispersion stabilizers and salts thereof.
• the invention further relates to processes for the preparation of these addition compounds, their use as wetting and dispersing agents and dispersion stabilizers for organic and inorganic pigments and fillers in organic and aqueous systems and in liquid systems employable powdered or fibrous solids, which are coated with such wetting agents and dispersants ,
• Dispersants are generally suitable for the stabilization of solid particles in binders, paints, pigment pastes, plastics and plastic mixtures, for reducing the viscosity of such systems and for improving the flow properties.
• Dispersion stabilizers are generally suitable for stabilizing already produced dispersions.
• dispersants In order to bring solids into liquid media, high mechanical forces are required. It is customary to use dispersants in order to lower the dispersing forces and to keep the total energy input into the system required for deflocculation of the solid particles and thus also the dispersion time as low as possible.
• Such dispersants are surfactants, anionic, cationic or neutral structure. These substances are either applied directly to the solid in a small amount or added to the dispersing medium. It is also known that even after complete deflocculation of the solid agglomerates in primary particles, after the dispersion process, reagglomeration can occur, as a result of which the dispersion effort is partially or completely nullified.
• EP 158 406 and EP 208 041 for example, use amino- and amide-functional poly- and oligocopolymers based on polyamines and polycaprolactones for dispersing pigments in which all the reactive amino groups have been converted into amide groups.
• these products are complex and poorly reproducible reaction mixtures and have very poor solubilities in solvents and inadequate compatibility with binders and other resins.
• the present invention is therefore based on the object to eliminate the disadvantages of known dispersants described above, that is to develop additives that reduce the Mahlgutviscosticians the paints, pastes or plastic formulations so far with good stabilization of pigments or fillers that processing at high degree of filling is possible without the resistances of the cured coatings are adversely affected.
• dispersing additives are to be provided which also act as wetting agents.
• the additives provided should also act as dispersion stabilizers, in particular as emulsion stabilizers.
• addition compounds are surprisingly broadly compatible and can be used as dispersants and / or dispersion stabilizers in both polar and nonpolar binder systems. They greatly reduce the viscosity of the ground material during the dispersion and therefore allow formulations with a high solids content to be produced. Furthermore, the addition compounds according to the invention are good wetting agents.
• XH is an isocyanate-reactive group
• Q is NH 2 , OH or NHR, wherein R is a linear or branched alkyl group having 1 to 18 carbon atoms, (c2) an isocyanate group blocking agent, and
• Z is an organic radical radical having at least one tertiary
• hydroxyl groups are reacted with polycarboxylic acids having at least two carboxyl groups or their anhydrides in such an amount that at least 0.8 molecules of the polycarboxylic acid or of the polycarboxylic acid anhydride are used for each hydroxyl group to be reacted;
• component (a) at least 10%, preferably 20%, particularly preferably 40% of the isocyanate groups of component (a) are reacted with component (c) and as component (c) at least 5 mol% of one or more of components (d) and or (c2) and that 0 to 50%, preferably 0 to 35%, particularly preferably 0%, of the isocyanate groups of component (a) are reacted with one or more components (c3).
• component (a) polyisocyanates having at least two isocyanate groups per molecule used.
• Such isocyanates are known in the art in the art.
• Such monomeric diisocyanates are, for example, 1,4-diisocyanatobutane, hexamethylene diisocyanate (HDI), 2-methyl-1,5-diisocyanatopentane, 1,5-diisocyanato-2,2-dimethylpentane, 2,2,4- or 2,4, 4-trimethyl-1,6-diisocyanatohexane, 1, 10-diisocyanatodecane, 1, 3- and 1, 4-diisocyanatocyclohexane, 1, 3- and 1, 4-bis- (isocyanatomethyl) -cyclohexane, 1-isocyanato-3, 3,5-trimethyl-5-isocyanatomethylcyclohexane (isophorone diisocyanate, IPDI), 4,4'-diis
• the said monomeric isocyanates can also be used as such alone or in a mixture or in a mixture with their biuret, urethane, uretdione and / or isocyanurate groups having oligomeric or polymeric derivatives.
• One or more monomeric, oligomeric or polymeric polyisocyanates may be used in the present invention.
• the polyisocyanates must have an average functionality of at least 2.
• the average functionality is preferably at least 2.5 and more preferably at least 3.
• Particularly preferred are the above-described derivatives of HDI, TDI and / or IPDI and in particular those of TDI.
• polyisocyanates examples include those which can be obtained, for example, by addition of diisocyanates to polyols, such as Desmodur L from Bayer or which can be obtained by biuret reaction from diisocyanates, such as the commercial product: Desmodur N from Bayer or else those obtainable by cyclization of diisocyanates
• Polyisocyanates with isocyanurate basic structure such as the commercial products Desmodur HL and Desmodur IL from Bayer, the commercial products Polurene KC or Polurene HR from SAPICI, or trimeric isophorone diisocyanate (isocyanurate T1890 from Chemische Werke Hüls).
• Desmodur VL polyisocyanate based on diphenylmethane diisocyanate (MDI).
• Bayer AG 1 Desmodur Z 4370 (polyisocyanate based on isophorone diisocyanate (IPDI), Bayer AG), Desmodur N3400 (aliphatic HDI uretdione, Bayer AG), Thanecure T9 (aromatic TDI uretdione, TSE Industries), Crelan VP LS 2147 and Crelan VP LS 2347 ( Aliphatic IPDI uretdiones, Bayer AG), Polurene KD (polyisocyanurate based on toluene diisocyanate (TDI), SAPICI), Uronal RA.50 (polyisocyanurate based on TDI from Galstaff), Polurene A (polyisocyanate based on TDI-trimethylolpropane (TMP),
• trimerization products of diisocyanates based on hexamethylene diisocyanate (HDI), isophorodiisocyanate (IPDI) and / or tolylene diisocyanate (TDI) are preferably used as the polyisocyanates.
• the average functionality can be determined experimentally by determining the number average molecular weight M n and the NCO number as described in the examples of the present invention and calculating the NCO equivalent weight therefrom.
• the average functionality is the quotient of the number average molecular weight and the NCO equivalent weight.
• the average functionality is preferably 2.5 to 10, more preferably 3 to 6.
• component (a) The polyisocyanates of component (a) are reacted according to the invention with compounds of component (b) of the above formula (I).
• the compounds of the formula (I) are characterized in that they contain one, two or three isocyanate-reactive groups XH.
• the compounds of the formula (I) react irreversibly via their reactive XH groups with the isocyanates. "Irreversible” in this context means that the compounds of the formula (I) can not be cleaved off again as a blocking agent (for example thermally)
• a blocking agent for example thermally
• XH examples include OH, NH 2 , NHR, SH or COOH, wherein R is a branched or unbranched alkyl group having 1 to 18 carbon atoms.
• R is a branched or unbranched alkyl group having 1 to 18 carbon atoms.
• XH is OH, NH 2 or NHR.
• These functional groups are particularly preferably hydroxyl groups because these compounds are readily available and / or commercially available and the reaction products obtained are readily soluble in solvents used in the later use of the additives according to the invention.
• the isocyanate-unreactive groups Y may have the heteroatoms O, S, Si and / or N and / or contain ether, urethane, carbonate, amide and / or ester groups.
• hydrogen is substituted by halogen, preferably fluorine and / or chlorine.
• aliphatic, cycloaliphatic and / or araliphatic compounds it is possible to use aliphatic, cycloaliphatic and / or araliphatic compounds. It is also possible to use mixtures of such compounds, ie at least two different compounds of the formula (I).
• the aliphatic or araliphatic compounds of the formula (I) may be straight-chain or branched. They can be saturated or unsaturated. However, saturated compounds are preferred.
• Examples of compounds of the formula (I) are straight-chain or branched alcohols, such as methanol, ethanol, butanol, ethylhexanol, decanol, isotridecyl alcohol, lauryl alcohol, stearyl alcohol, isobomyl alcohol, benzyl alcohol, propargyl alcohol, oleyl alcohol, linoleyl alcohol, oxo alcohols, neopentyl alcohol, cyclohexanol, fatty alcohols, alkylphenols, monophenyldiglycol , Alkyl naphthols, phenylethanol, hydroxy-functional vinyl compounds such as hydroxybutyl vinyl ether, hydroxy-functional acrylates or methacrylates such as hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxybutyl (meth) acrylate and hydroxyethyl ethyleneurea and polyolefin polyols such as optionally hydrogen
• Examples of corresponding commercial products are the hydroxy-terminated hydrogenated P available under the name Polytail® from Mitsubishi Chemical olybutadiene or the hydroxy terminated ethylene / butylene copolymers Kraton® Liquid L-1203, L-1302 and L-2203 from Kraton Polymers or the liquid polybutadienes available from Nippon Soda Co. as NISSO-PB or those available from Baker Petrolite as Unilin® Alcohols saturated, long-chain, linear, substantially primary alcohols having chain lengths up to C 5 o and molecular weights of 375 to 700 g / mol and their available under the name Unithox® ethoxylates. Further examples are described inter alia in EP-A-154,678.
• esters, ethers, urethane, carbonate, amide and / or siloxane groups or combinations of these groups may therefore be, for example, polyethers, polyesters, polyurethanes, polycarbonates, polysiloxanes or mixed polyether polyesters, for example.
• polyesters can be prepared by reaction of dicarboxylic acids and their esterifiable derivatives such as anhydrides, acid chlorides or dialkyl esters such as dimethyl esters or diethyl esters by reaction with diols and mono-, di- or trifunctional starting components.
• dihydroxy polyesters can be suppressed, if necessary, by using stoichiometric amounts of monohydroxy compounds as described above.
• the esterification can be carried out in bulk or else by azeotropic esterification in the presence of an entraining agent.
• dicarboxylic acids are succinic, maleic, fumaric, glutaric, adipic, sebacic, pimelic, phthalic or dimerized fatty acids and their isomers and hydrogenation products.
• diols are: ethylene glycol, 1, 2-propanediol, 1, 3-propanediol, 1, 4-butanediol, 1, 6-hexanediol, neopentyl glycol, cis-i ⁇ -Cyclohexandimethanol, trans-1, 2-cyclohexanedimethanol, and polyglycols based on ethylene glycol and / or propylene glycol.
• Preferred polyesters of the formula (I) are those obtained by polycondensation of one or more, optionally alkyl-substituted, hydroxycarboxylic acids and / or ring-opening polymerization of the corresponding lactones such as propiolactone, valerolactone, caprolactone by means of a mono-, di- or trihydroxy starting component, such as in EP-A-154,678 (US-A-4,647,647).
• these have a number average molecular weight M n of 150 to 5000 g / mol.
• all compounds other than compounds of the formula (I) can be used as the starting component.
• the mono-, di-, or trifunctional alcohols used as starting components preferably have 1 to 30, more preferably 4 to 14, carbon atoms.
• Examples include n-butanol, long-chain, saturated and unsaturated alcohols such as propargyl alcohol, oleyl alcohol, linoleyl alcohol, oxo alcohols, cyclohexanol, phenylethanol, neo-pentyl alcohol, ethylene glycol, propylene glycol and glycerol, but also fluorinated alcohols, hydroxy-functional polydialkylsiloxanes, hydroxy-functional vinyl compounds such as hydroxybutyl vinyl ether, hydroxy-functional Acrylates or methacrylates such as hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxybutyl (meth) acrylate, hydroxyfunctional polyalkylene glycol acrylates and methacrylates.
• alkylene oxides such as ethylene oxide, propylene oxide, butylene oxide and / or styrene oxide
• alkylene oxides such as ethylene oxide, propylene oxide, butylene oxide and / or styrene oxide
• Polyoxyalkylenmonoalkyl-, Polyoxyalkylenmonoaryl-, Polyoxyalkylenmonoaralkyl- and Polyoxyalkylenmonocycloalkylether and these hydroxypolyethers in the as described above are used as starting components for the lactone polymerization. It is also possible in each case to use mixtures of the abovementioned compounds.
• Lactonpolymerisation is carried out by known methods, initiated by, for example, p-toluenesulfonic acid or dibutyltin dilaurate, at temperatures of about 70 ° C to 180 0 C.
• Particularly preferred ⁇ -caprolactone-based polyesters, optionally in combination with ⁇ -valerolactone are particularly preferred.
• mono-, di- or trihydroxypolyethers can be obtained, for example, by alkoxylation of compounds other than compounds of formula (I), such as alkanols, cycloalkanols, phenols or the hydroxypolyesters described above with alkylene oxides such as ethylene oxide, propylene oxide, butylene oxide, styrene oxide or mixtures thereof.
• alkylene oxides such as ethylene oxide, propylene oxide, butylene oxide, styrene oxide or mixtures thereof.
• mixed polyethers these may be random, gradient or in blocks.
• These polyethers suitably have a number average molecular weight (M n ) in the range of about 100 to 10,000, preferably from 150 to 5000 and more preferably from 200 to 3500 g / mol.
• polyethers based on ethylene oxide, propylene oxide and mixtures thereof Preference is given to polyethers based on ethylene oxide, propylene oxide and mixtures thereof. More preferably, monohydroxy-polyoxyalkylene monoalcohols such as allyl polyethers such as polyglycol A 350, A 500 polyglycol, polyglycol A 1100, A Polyglycol 11-4, polyglycol or polyglycol A 20-10 A 20-20 are Clariant AG or Pluriol ® A 010 R, ® Pluriol A 11 RE, Pluriol ® A 13 R, Pluriol ® A 22 R or Pluriol ® A 23 R BASF AG, vinyl polyether such as polyglycol V 500, polyglycol V 1100 or polyglycol V 5500 of Clariant AG, methanol started Polyoxyethylenmonoalkohole such as Pluriol ® A 350 e, Pluriol ® A 500 e, Pluriol ® A 750 e, Pl
• polyoxyalkylene monoalcohols which contain ethylene oxide and / or propylene oxide and / or butylene oxide groups and are optionally modified with styrene oxide.
• Particularly preferred is the use of polyoxyalkylene monoalcohols such as polyglycol B 11/50, polyglycol B 11/70, polyglycol B 11/100, polyglycol B 11/150, polyglycol B 11/300 or polyglycol B 11/700 from Clariant AG, Pluriol ® A 1000 PE, Pluriol A 1320 ® PE, or Pluriol A 2000 ® PE BASF AG or Terralox WA 110 from DOW Chemicals which are butanol-started polyoxyalkylenes of ethylene and propylene oxide having a terminal OH group.
• Preferred compounds of the formula (I) are hydroxy-functional polyethers, hydroxy-functional polyesters, hydroxy-functional polyether polyesters and / or aliphatic and / or cycloaliphatic alcohols having 2 to 30 carbon atoms, the hydrogen atoms of which are optionally partially replaced by halogen and / or aryl radicals.
• polysiloxanes for example amino- or hydroxy-functional polydialkylsiloxanes which contain hydroxyl groups which are not bonded to silicon atoms or aminoalkylpolysiloxanes which may optionally be polyether- and / or polyester-modified.
• the respective amino-functional compounds carry primary or secondary, but not tertiary amino groups.
• Polyurethanes, polyether polyurethanes, polyester-polyurethanes and / or polyether-polyester-polyurethanes which are obtained by addition reaction of diisocyanates with dihydroxy compounds in the presence of mono-, di- or trifunctional starter components can also be used as compounds of the formula (I) can.
• diisocyanate for the construction of the urethane group-containing compounds of the formula (I) it is possible to use the aliphatic, cycloaliphatic and / or aromatic diisocyanates having from 4 to 15 carbon atoms known per se from polyurethane chemistry, such as tetramethylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate,
• Preferred hydroxy compounds for the preparation of the urethane group-containing compounds of the formula (I) are diols having 2 to 12 carbon atoms, polyoxyalkylene glycols and dihydroxyfunctional Polyester with preferred number average molecular weights M n of at most 2000 g / mol used.
• the polyesters preferably have a number average molecular weight M n of 300 to 5000 g / mol and the polyethers of 200 to 2000 g / mol.
• the group Y may also contain carbonate groups as obtained by the prior art reaction with open-chain and / or cyclic carbonates.
• carbonates-modified linear polyesters or polycarbonate diols as used in polyurethane production are suitable. Examples are described in US 410 152 9, EP 0358 555, or WO 02/085507.
• Suitable carbonates are, for example, aliphatic, cycloaliphatic, araliphatic and / or aromatic carbonic esters, for example dialkyl carbonates, such as dimethyl carbonate, diethyl carbonate or diphenyl carbonate, catechol carbonate or cyclic alkylene carbonates.
• cyclic Alkylencarbonate with 5 or 6-membered rings, which may be optionally substituted.
• substituents aliphatic, cycloaliphatic and / or aromatic groups having up to 30 carbon atoms are preferred.
• suitable cyclic alkylene carbonates are ethylene carbonate, propylene carbonate, glycerol carbonate, trimethylene carbonate, 4-methyltrimethylene carbonate, 5-methyltrimethylene carbonate, 5,5-dimethyltrimethylene carbonate, 5.5-
• the radical Y can carry further groups which are inert in the formation of the addition product, for example the carboxylic acid amide group (-NHCO-), unactivated double bonds or urea groups (-NHCONH-).
• the proportion of the compounds of the formula (I) which carry such groups should, based on all the compounds of the formula (I) used, preferably be less than 50 mol%, preferably less than 5 mol%. Particular preference is given to compounds which do not contain any of these groups.
• esters, ethers, urethane, carbonate and / or siloxane groups may be present in block structure (for example poly (ethylene oxide block) propylene oxide block-epsilon-caprolactone), forming a gradient or even randomly arranged.
• polyacrylic acid esters and / or polymethacrylic acid esters having on average up to three NCO-reactive groups as obtained by anionic, cationic or free-radical polymerization of acrylic esters or methacrylic esters.
• Monohydroxy-functional polyacrylic acid esters or polymethacrylic acid esters are those which contain on average one hydroxyl group in the molecule.
• Such compounds have already been used in the art for the preparation of other dispersants such as described in US-A-4 032 698 or EP 318 999.
• These polyacrylates preferably have a number average molecular weight M n of 300 to 20,000 g / mol, more preferably 500 to 10,000 g / mol. They can be arranged in a block structure or also statistically or form a gradient.
• the carboxyl group of the monomeric acrylates or methacrylates may be, for example, esterified with aliphatic, cycloaliphatic and / or aromatic alcohols, such as methanol, butanol, cyclohexanol, 2-ethylhexanol, lauryl alcohol, stearyl alcohol, isobomyl alcohol, benzyl alcohol, or with ether alcohols, such as 2-methoxyethanol.
• aliphatic, cycloaliphatic and / or aromatic alcohols such as methanol, butanol, cyclohexanol, 2-ethylhexanol, lauryl alcohol, stearyl alcohol, isobomyl alcohol, benzyl alcohol, or with ether alcohols, such as 2-methoxyethanol.
• Phenoxyethanol, tetrahydrofurfuryl alcohol or glycidol be esterified with polyester alcohols such as hydroxy-functional polycaprolactone, or with Alkoxypolyalkylenglykolen such as methoxypolyethylene glycol or methoxypolypropylene glycol.
• the number average molecular weight M n of the esterification component is preferably below 2000 g / mol.
• vinyl esters such as vinyl acetate, vinyl ethers such as vinyl ethyl ether, styrene, vinyl toluene and / or vinylcyclohexane.
• the copolymers obtained in this way were synthesized from preferably not more than 50 mol% of non-acrylic-functional comonomers.
• hydroxy-functional poly-2-alkyl-2-oxazolines or poly-2-alkyl-2-oxazines may also function.
• Poly-2-alkyl-2-oxazolines or poly-2-alkyl-2-oxazines are, as known in the art, by cationic, ring-opening polymerization of 2-alkyl-2-oxazolines or 2-alkyl-2-oxazines with initiators such For example, para-toluenesulfonic acid, methyl tosylate or methyl triflate obtained. The oxazolinium or. Resulting from the living cationic polymerization mechanism
• Oxazinium end groups can be converted into the more stable hydroxyamides by alkaline hydrolysis via aminoester end groups.
• An alternative route to the preparation of monohydroxy-functional poly-2-alkyl-2-oxazolines or poly-2-alkyl-2-oxazines is the polymerization with 2- (4-hydroxyphenyl) -N-methyl-2-oxazolinium trifluoromethanesulfonate as initiating species. (Gross, G. Maier, O. Nuyken, Macromol Chem Phys., 197, 2811-2826 (1996)).
• the compatibility can be controlled by choice of the alkyl substituent, for example poly-2-ethyl-2-oxazoline is suitable for highly polar systems owing to its water solubility, while, for example, poly-2-lauryl-2-oxazoline is compatible in non-polar systems. If block copolymers of 2-ethyl-2-oxazoline and 2-lauryl-2-oxazoline formed, the polymers are characterized by a particularly broad compatibility.
• Such poly-2-alkyl-2-oxazolines or poly-2-alkyl-2-oxazines preferably have a number average molecular weight M n of 300 to 20,000 g / mol, more preferably 500 to 10,000 g / mol.
• addition compounds prepared with mixtures of various compounds of formula (I) are often advantageous. If the addition compounds according to the invention are to be used, for example, in universal tinting pastes for aqueous and nonpolar systems, a combination of water-soluble and nonpolar compounds of the formula (I) is advantageous.
• the number average molecular weight M n of the compound of the formula (I) is less than 20000 g / mol and is preferably not more than 10,000 g / mol, more preferably not more than 5000 g / mol, very particularly preferably not more than 3500 g / mol and even better at a maximum of 2000 g / mol.
• the minimum molecular weight M n is preferably 100 g / mol, particularly preferably 150 g / mol, very particularly preferably 200 g / mol and most preferably 400 g / mol.
• Preferably less than 50 mol% of the compounds of formula (I) used have a number average molecular weight of less than 100 g / mol, more preferably less than 25 mol%, most preferably less than 15 mol% and most preferably 0 mol%.
• di- or trifunctional compounds of the formula (I) are diols and triols or diamines and triamines without tertiary amino groups having 2 to 12
• Glycerol trimethylolpropane, fatty acid dialkanolamides, thiodiglycol, di (4-)
• a preferred group of compounds of formula (I) are polyoxyalkylene glycols particularly preferred with alkylene groups having 2 to 4, most preferably having 2 carbon atoms, and preferably number-average
• Preferred polyoxyalkylene glycols are polyethylene glycols.
• di- or trifunctional compounds of the formula (I) it is also possible to use those which can be obtained by polymerization of one or more lactones, preferably epsilon-caprolactone, as already mentioned, by means of di- or trihydroxy starter components.
• these polyester polyols Preferably, these polyester polyols have a number average molecular weight M n of 500 to 2000 g / mol.
• butanediol or ethylene glycol is preferred. But there are also the above diols or triols as starter components in question.
• the polyfunctional compounds of the formula (I) are difunctional or trifunctional polyethers, polyesters or polyetherpolyesters.
• Polyurethanes, polyether-polyurethanes, polyester-polyurethanes and / or polyether-polyester-polyurethanes which are obtained by addition reaction of a diisocyanate with a dihydroxy compound analogously to the corresponding monofunctional compounds of the formula (I) can also be used as polyfunctional compounds of the formula (I) can be.
• These urethane-containing compounds of the formula (I) preferably have an average functionality of not more than 2 and a number average molecular weight of from 300 to 2500 g / mol, preferably from 500 to 1500 g / mol.
• the di- or trifunctional compounds of the formula (I) bring about crosslinking between the reaction products of polyisocyanate and monofunctional compounds of the formula (I).
• the starting materials can be used in amounts such that the di- or trifunctional compounds of formula (I) represent the center of the molecule and that are bound to the polyisocyanates whose remaining isocyanate groups reacted with monofunctional compounds of formula (I) are or will be. There may of course also be some over-crosslinking or under-crosslinking.
• the reaction of the polyisocyanates with various compounds of the formula (I) can be carried out successively in a single reaction step or in several reaction steps. This can be done in any order. In many cases, however, it is expedient to react the polyisocyanate in succession with the components in the order first monofunctional and then polyfunctional compounds.
• the isocyanate addition can, depending on Reactivity of the individual reactants, in the usual temperature range for this type of reaction from room temperature to about 150 0 C.
• the catalysts known and customary in the prior art such as tertiary amines, such as triethylamine, dimethylcyclohexylamine, N-methylmorpholine, N 1 N 1 - dimethylpiperazine, 2- (dimethylaminoethoxy) ethanol, diazabicyclo- (2 , 2,2) -octane and similar and in particular organic metal compounds such as titanic acid esters, iron compounds such as iron (lll) acetylacetonate, tin compounds, such as tin diacetate, tin dioctoate, tin dilaurate or the dialkyl derivatives of Zinndialkylsalzen aliphatic carboxylic acids such as dibutyltin diacetate, dibutyltin dilaurate or the like become. These catalysts are usually used in amounts of 0.0001 to 0.1 parts by weight per 100 parts by weight of polyisocyanate.
• MQ of the formula (II) used are compounds in which M is an organic radical having a number average molecular weight of not more than 1000 g / mol, preferably not more than 500 g / mol and more preferably 300 g / mol, of i) at least one tertiary one Amino group and at least one OH group or ii) contains at least one hydrolyzable silane group, and wherein Q is Nhfe, NHR or
• M contains 1 to 10, more preferably 1 to 5, and most preferably 1 to 3, most preferably 1 to 2, OH groups.
• Primary OH groups are preferred.
• MQ with tertiary amino groups and OH groups are triethanolamine, N-methyldiethanolamine, aminopropylmethylethanolamine, 3- (diethylamino) propane-1, 2-diol, tetrakis (2-hydroxypropyl) ethylenediamine, bis (2-hydroxyethyl) dodecylamine, bis ( 2-hydroxyethyl) octadecylamine.
• Bis (trimethoxysilylpropyl) amine bis [(3-trimethoxysilyl) propyl] ethylenediamine, bis (3-trimethoxysilylpropyl) -N-methylamine, n-butylaminopropyltrimethoxysilane, t-butylaminopropyltrimethoxysilane, N-cyclohexylaminopropyltrimethoxysilane, 3- (2,4-dinitrophenylamino) propylthethoxysilane , N-ethylaminoisobutylmethyldiethoxysilane, N-ethylaminoisobutyltrimethoxysilane, N- (3-methacryloxy-2-hydroxypropyl) -3-aminopropyltriethoxysilane, N-methylaminopropylmethyldimethoxysilane, N-
• the terminal alkoxy groups can be hydrolyzed in water or aqueous media to form hydroxy functionalities
• Alkoxysilane-containing adducts are particularly suitable for hydroxyl-containing surfaces such as quartz or glass fibers, with which they undergo a particularly strong bond under reaction and therefore can also bring about improvements in adhesion and mechanical properties, in particular in combination with mitvernetzbaren radicals Y with, for example, acrylic groups.
• Blocking agents are used for reversible reaction with isocyanate groups. Of these, the blocking agents can be cleaved off, for example, thermally after conversion, so that the isocyanate groups are available for reaction again.
• blocked isocyanate in the present art is a term familiar to one of ordinary skill in the art and is used to prepare blocked isocyanates.
• Suitable blocking agents are known in the art, such as lactams, oximes, malonic esters, alkylacetoacetates, phenols, and amines, such as butanone oxime, acetone oxime, diisopropylamine, 1, 2,4-triazole, imidazole, dimethylpyrazole, Diethyl malonate, acetoacetic ester, epsilon-caprolactam or any mixtures of these blocking agents.
• those representatives of the classes of compounds are excluded as blocking agents which, in addition to the group which reversibly blocks the isocyanate groups, carry one or more groups which react irreversibly with isocyanate groups.
• those representatives of the classes of compounds which fall under the definition of the formula (I) are excluded.
• These representatives of the corresponding classes of compounds are assigned exclusively to component (b).
• Butanone oxime, imidazole, dimethylpyrazole, and epsilon-caprolactam or mixtures of these compounds are preferably used. Particularly preferred are imidazole and 3,5-dimethylpyrazole.
• the blocked polyisocyanate groups are prepared, for example, by
• the preparation of the blocked polyisocyanate adducts can be carried out by direct reaction of the isocyanate groups with the blocking agent or in the case of CH-acidic blocking agents, such as malonic acid esters with the addition of deprotonating agents.
• the component (c3) is optional and represented by the general formula (III) as Z-Q.
• the group Z is an organic basic radical having at least one tertiary amino group which contains no NCO-reactive groups.
• the radical Z is an aliphatic or cycloaliphatic group having at least one tertiary amino group, optionally in the form of a tertiary ring nitrogen atom of a heterocyclic ring system.
• the tertiary amino group or the tertiary ring nitrogen heterocyclic ring system can be bonded directly to the group Q or via an "organic spacer" group
• the spacer via which the tertiary amino group or the tertiary ring nitrogen heterocyclic ring system is bonded to the Q group may preferably comprise 2 to 10, more preferably 2 to 5 carbon atoms, more preferably an alkylene group having 2 to 10, most preferably 2 to 5 carbon atoms or a polyether group having the same number of carbon atoms Component (d) defined.
• a group of compounds that can be used as compounds ZQ of formula (III) consists of monohydroxyamines having a tertiary amino group or aliphatic diamines having a tertiary amino group and a primary or secondary amino group such as (N, N-diethylamino) ethanol, ( N 1 N-dimethylamino) ethanol, (N, N-dimethylamino) propanol 2- (diethylamino) ethylamine, 3- (dimethylamino) propylamine, 3- (diethylamino) propylamine, N, N-diethyl-1, 4- butanediamine, 1 -Diethylamino-4-aminopentane, of which 3- (dimethylamino) propylamine and (NN-diethylamino) ethanol are preferred.
• Preferred heterocycles are triazole, pyrimidine, imidazole, pyridine, morpholine, pyrrolidine, piperidine, Benzimidazole, benzothiazole and / or triazine and more preferably imidazole and benzimidazole.
• These heterocycles may have one or more substituents.
• they carry one of the following groups: alkyl and / or alkoxy groups having 1 to 6, preferably 1 to 4 carbon atoms (with a methoxy group being preferred) or tertiary amino groups.
• heterocyclic groups are bonded to the group Q via a ring nitrogen atom and an alkylene group, preferably having 2 to 5 carbon atoms.
• the heterocyclic group may of course contain, in addition to this ring nitrogen atom, further heteroatoms, including further ring nitrogen atoms.
• compounds of the formula (III) are N- (3-aminopropyl) imidazole, N- (3-aminopropyl) morpholine, N- (2-aminoethyl) piperidine, 1-methylpiperazine, aminoethylpiperazine.
• Characteristic of these compounds is that they contain per molecule at least 1 reactive group with at least 1 Zerewitinoff hydrogen atom, which can react with the NCO groups, and that they additionally have a nitrogen-containing basic group without reactive hydrogen.
• These basic groups are characterized by their pKa value according to the prior art (see US-A-3,817,944, 4,032,698 and 4,070,388).
• the pKa value can be found in the tables.
• the limit values given above refer to the measurement of the pKa value at 25 ° C. in a 0.01 molar concentration in water.
• These basic groups also impart a basicity to the addition compounds according to the invention.
• Compounds of formula ZQ can be obtained, for example, by reacting a (meth) acrylate or epoxide with an amine or nitrogen-containing heterocyclic ring system.
• reaction products between a (meth) acrylate and a nitrogen-containing heterocyclic ring system are the reaction products of the hydroxyethyl and hydroxypropyl esters of (meth) acrylic acid with the nitrogen-containing heterocyclic ring structure, the following Structural elements attached to the nitrogen of the heterocyclic ring structure are:
• 2-hydroxyethylyl propionate propionic acid 2-hydroxypropyl ester, 2-methylpropionic acid 2-hydroxyethylyl ester and 2-methylpropionic acid 2-hydroxypropyl ester, and ethoxylated and / or propoxylated derivatives thereof.
• the acrylic esters are preferred.
• the compounds Z-Q can also be prepared.
• a secondary hydroxyl group is formed as group Q and a tertiary amino group is formed on the reactive nitrogen atom.
• mixtures of different starting materials such as mixtures of polyisocyanates, and / or components (b) and / or components (c).
• Individual ones of the plurality of components (a), (b1), (b2) or (c) may be used in excess or deficiency.
• the proportions are chosen so that the isocyanate groups are substantially completely reacted. It is to be understood that preferably at least 90%, more preferably at least 95%, most preferably at least 98% and optimally all isocyanate groups are reacted.
• the addition compounds are capable of salt formation.
• they can also be used as dispersants in the form of the corresponding salts.
• partial or complete salinization can improve efficacy and / or improve solubility or compatibility.
• improvements can often be achieved by partial or complete neutralization.
• the salts are obtained from the obtained reaction product by neutralization with one or more organic or inorganic acids or by quaternization. The amount of acid to be used depends on the field of application. Depending on the individual case, the acid components can be used equimolar, in excess or in excess.
• polycarboxylic acids for example, up to one equivalent of polycarboxylic acid per basic group to be neutralized can be used to give the products an acidic character. Preference is approximately neutralized equimolar. Preference is given to salts with organic carboxylic acids or acidic phosphoric acid esters. Examples of such acidic phosphoric acid esters are listed in EP 893 155, EP 417 490 and US Pat. No. 5,143,952.
• carboxylic acids are aliphatic and / or aromatic carboxylic acids, such as short- or long-chain fatty acids, formic acid, acetic acid, neodecanoic acid, oleic acid, tall oil fatty acid, stearic acid, Rizinolic acid, natural saturated or unsaturated vegetable or animal fatty acids and their maleic anhydride adducts, maleic acid, fumaric acid, succinic acid, dodecenylsuccinic acid, 5-norbornene-2,3-dicarboxylic acid, adipic acid,
• carboxylic acids are aliphatic and / or aromatic carboxylic acids, such as short- or long-chain fatty acids, formic acid, acetic acid, neodecanoic acid, oleic acid, tall oil fatty acid, stearic acid, Rizinolic acid, natural saturated or unsaturated vegetable or animal fatty acids and their maleic anhydride adducts, maleic acid, fum
• Glutaric acid benzoic acid, nitrobenzoic acid, phthalic acid, tetrahydrophthalic acid, isophthalic acid, terephthalic acid, dimerized or trimerized fatty acids, citric acid and abietic acid.
• addition compounds according to the invention contains hydroxyl groups, these may optionally be reacted with polycarboxylic acids having at least two carboxyl groups or their anhydrides in such an amount with ester formation that at least 0.8 molecules of the polycarboxylic acid or the polycarboxylic anhydride are used for each hydroxyl group to be reacted.
• the thus reacted addition compounds thus contain per reacted OH group one or more carboxyl groups which are capable of salt formation with the amino groups.
• polycarboxylic acids examples include maleic acid, fumaric acid, succinic acid, dodecenylsuccinic acid, 5-norbornene-2,3-dicarboxylic acid, adipic acid, glutaric acid, phthalic acid, tetrahydrophthalic acid, isophthalic acid, terephthalic acid, dimerized or trimerized fatty acids and citric acid.
• anhydrides of 1,2-dicarboxylic acids such as maleic anhydride, succinic anhydride, dodecenylsuccinic anhydride, phthalic anhydride and tetrahydrophthalic anhydride.
• the addition compounds according to the invention preferably contain no ethylenically unsaturated groups.
• polyisocyanates preferably used with an average of at least 2.5 free isocyanate groups leads to the formation of branched, i. non-linear polyurethane structures. Consequently, non-linear addition compounds are particularly preferred according to the invention.
• the preparation of the addition compounds according to the invention can be carried out in bulk or in the presence of suitable solvents, solvent mixtures or other suitable carrier media.
• suitable solvents, solvent mixtures or other suitable carrier media are all solvents or carrier media which are not reactive under the chosen reaction conditions or whose reactivity towards the reactants is negligible and in which the reactants and the reaction products are at least partially soluble.
• hydrocarbons such as toluene, xylene, aliphatic and / or cycloaliphatic gasoline fractions
• chlorinated hydrocarbons such as chloroform, trichloroethane, cyclic and acyclic ethers such as dioxane, tetrahydrofuran
• polyalkylene glycol dialkyl ethers such as dipropylene glycol dimethyl ether
• esters of mono-, di- or polycarboxylic acids such as ethyl acetate, butyl acetate, Butyrolactone, dimethyl 2-methylglutarate, triacetin, phthalates or other plasticizers
• di- or polycarboxylic acid esters dialkyl esters of C 2 -C 4 -dicarboxylic acids called "dibasic esters" alkyl glycol esters such as ethyl glycol acetate, methoxypropyl acetate, ketones such as methyl isobut
• the formulation should be as solvent-free as possible or in correspondingly high-boiling carrier media.
• the solvents used for the synthesis may remain in the reaction mixture or be completely or partially removed and optionally replaced by other solvents or carrier media.
• the addition compounds according to the invention can also be combined with resins, resin solutions, reactive diluents, binders or with other additives known from the prior art, for example other wetting and dispersing agents, anti-settling agents, surface-active additives such as, for example, silicones and the like.
• the solvent can be removed, for example, by distilling off, if appropriate under reduced pressure and / or azeotropically with the addition of water, in whole or in part.
• the active substance can also be isolated by precipitation by addition of non-solvents such as aliphatic hydrocarbons, for example hexane, followed by separation by filtration and optionally drying.
• the active substance obtained by one of these methods can then be dissolved in a solvent suitable for the respective field of application or, if appropriate, used in pure form, for example in the case of powder coatings.
• the solvent in which the addition product is dissolved after addition of suitable higher-boiling solvents, optionally under reduced pressure and / or azeotrope with the addition of water, distilled off and thereby the addition product are converted into a suitable carrier for the respective application medium.
• suitable carrier for the respective application medium.
• the addition compounds can also be converted to a solid form by other processes known to the art for polymers. Examples of such processes are microencapsulation, spray drying, adsorption on a solid carrier such as SiO 2 or the PGSS method (Particle from Gas Saturated Solutions).
• the reactions can be carried out in the presence of conventional catalysts, for example organic tin compounds such as dibutyltin dilaurate, other organometallic compounds such as iron acetylacetonate, tertiary amines such as triethylenediamine, enzymes or the like.
• organic tin compounds such as dibutyltin dilaurate
• other organometallic compounds such as iron acetylacetonate
• tertiary amines such as triethylenediamine
• enzymes or the like for example organic tin compounds such as dibutyltin dilaurate, other organometallic compounds such as iron acetylacetonate, tertiary amines such as triethylenediamine, enzymes or the like.
• solubility and the compatibility with a wide variety of solvents, carrier media, binders, resins, solids and optionally other polymeric compounds can be tuned, which are present in coating and molding compositions in which the addition compounds according to the invention are used.
• the radicals Y should contain a sufficiently high proportion of polar groups such as polyethylene oxides in order to achieve sufficient water solubility for the respective application.
• this proportion of hydrophilic groups should also not be too high if this leads to an undesirable increase in water sensitivity in certain applications.
• nonpolar groups When used in non-polar systems such as long-oil alkyd paints, PVC plastisols or polyolefins, an appropriate proportion of nonpolar groups should preferably be present and when used in systems where broad compatibility is important, such as pigment concentrates, is a balanced combination of polar and nonpolar groups of Advantage.
• polydimethylsiloxane-containing addition compounds are particularly suitable.
• the addition compounds are used, for example, in a polyurethane resin or in a lacquer whose binder is a polyurethane, it is expedient to use such addition compounds according to the invention, which also contain urethane groups or the like in their molecule due to the groups contained in the starting compounds of the formula (I) Contain groups which are - as is known in the art, compatible with polyurethanes.
• Addition compounds according to the invention having surface-active substituents can alter the surface tension of the substrates produced therewith.
• very nonpolar groups such as long chain alkyl groups of greater than 12 carbon atoms, polydimethylsiloxane containing and / or perflouralkyl containing groups
• the products are useful for reducing the surface tension of liquid organic or aqueous or solid systems and related properties such as For example, to influence wetting properties, soiling, printability, flow and foaming behavior.
• the number average molecular weight M n of the addition compounds according to the invention is preferably at least 500 g / mol, more preferably at least 800 g / mol, very particularly preferably at least 1200 g / mol and ideally at least 2000 g / mol.
• Another object of the invention is a process for the preparation of the addition compounds of the invention, wherein a reaction is carried out by
• XH is an isocyanate-reactive group
• Q is NH 2 , OH or NHR, wherein R is a linear or branched alkyl group having 1 to 18 carbon atoms, (c2) an isocyanate group blocking agent, and
• Z is an organic radical radical having at least one tertiary
• hydroxyl groups are reacted with polycarboxylic acids having at least two carboxyl groups or their anhydrides in such an amount that at least 0.8 molecules of the polycarboxylic acid or of the polycarboxylic acid anhydride are used for each hydroxyl group to be reacted;
• component (a) at least 10% of the isocyanate groups of component (a) are reacted with component (c) and as component (c) at least 5 mol% of one or more of components (d) and / or (c2) are used and that 0 to 50% of the isocyanate groups of component (a) are reacted with component (c) and as component (c) at least 5 mol% of one or more of components (d) and / or (c2) are used and that 0 to 50% of the isocyanate groups of
• Component (a) with one or more components (c3) are reacted.
• Another object of the invention is the use of the above-described addition compounds according to the invention as wetting or dispersing agents and as dispersion stabilizers.
• the invention also provides powdery or fibrous solids which are to be incorporated into liquid systems and which are coated with these addition compounds as dispersants and as dispersion stabilizers or as wetting agents.
• the addition compounds according to the invention can be used instead of the dispersants known from the prior art, dispersion stabilizers or wetting agents.
• they can be used in the production or processing of paints, printing inks, inks, for example for ink-jet printing, paper coating, leather and textile dyes, pastes, pigment concentrates, ceramics, and cosmetic preparations, especially if these solids, such as pigments and / or fillers contain.
• molding compositions based on synthetic, semisynthetic or natural macromolecular substances, such as, for example, polyvinyl chloride, saturated or unsaturated polyesters, polyurethanes, polystyrenes, polyacrylates, polyamides, epoxy resins, polyolefins, such as polyethylene or polypropylene.
• synthetic, semisynthetic or natural macromolecular substances such as, for example, polyvinyl chloride, saturated or unsaturated polyesters, polyurethanes, polystyrenes, polyacrylates, polyamides, epoxy resins, polyolefins, such as polyethylene or polypropylene.
• the addition compounds are preferably used to prepare pigment concentrates, paints, pastes and / or molding compositions containing pigments and / or fillers.
• Examples of conventional binders are resins based on polyurethanes, cellulose nitrates, cellulose acetobutyrates, alkyds, melamines, polyesters, chlorinated rubbers, epoxides and acrylates.
• Examples of water-based coatings are cathodic or anodic electrodeposition coatings, for example for automobile bodies. Further examples are plasters, silicate paints, emulsion paints, water-based paints based on water-dilutable alkyds, alkyd emulsions, hybrid systems, 2-component systems, polyurethane and acrylate dispersions.
• the addition compounds of the invention are also particularly suitable for the production of solid concentrates, such as pigment concentrates.
• the compounds according to the invention are initially introduced in a carrier medium such as organic solvents, plasticizers and / or water, and the solids to be dispersed are added with stirring.
• these concentrates may contain binders and / or other adjuvants.
• the presscake which may contain organic solvents, plasticizers and / or water, the compound of the invention is added and the mixture thus obtained dispersed.
• the solid concentrates prepared in various ways can then be incorporated into different substrates such as Aikyd resins, polyester resins, acrylate resins, polyurethane resins or epoxy resins.
• pigments can also be dispersed directly in the addition compounds according to the invention without solvent, and are then particularly suitable for pigmenting thermoplastic and thermoset plastic formulations.
• the addition compounds according to the invention can also be advantageously used in the production of color filters for liquid crystal displays, screens, color resolvers, sensors, plasma screens, displays based on the SED (Surface Conduction Electron Emitter Display) and for MLCC (Multi Layer Ceramic Compounds).
• MLCC technology is used in the manufacture of microchips and printed circuit boards.
• the addition compounds of the invention can also be used for the preparation of cosmetic preparations such as make-up, powders, lipsticks, hair dyes, creams, nail polishes and sunscreen preparations. These may be in the usual forms such as W / O or O / W emulsions, solutions, gels, creams, lotions or sprays.
• the addition compounds according to the invention can advantageously be used in dispersions used for the preparation of these preparations. These may contain the carrier media customary for these purposes in cosmetics, such as, for example, water, castor oils or silicone oils and solids, for example organic and inorganic pigments, such as titanium dioxide or iron oxide.
• the invention further relates to the use of an addition compound according to the invention for producing a pigmented paint which is used in particular for producing a pigmented coating on a substrate, wherein the pigmented paint is applied to the substrate and wherein the pigmented paint applied to the substrate is baked or cured or crosslinked ,
• the dispersants may be used alone or in combination with binders customary in the art. When used in polyolefins, it may be advantageous, for example, to use corresponding low molecular weight polyolefins as support materials together with the dispersant.
• An inventive use of the addition compounds is also in the production of dispersible powder particles and / or fibrous particulate solids, in particular dispersible pigments or plastic fillers, wherein the particles are coated with the addition compound according to the invention.
• Such coatings of organic as well as inorganic solids are known in known manner, as described for example in EP-AO 270 126.
• the solvent or emulsifier can either be removed or remain in the mixture to form pastes.
• These pastes are common commercial products and may additionally contain binder portions as well as other auxiliaries and additives.
• the coating of the pigment surface can take place during or after the synthesis of the pigments, for example by addition of the addition products according to the invention to the pigment suspension or during or after the pigment finish.
• the pretreated in this way pigments are characterized by easier incorporation and improved viscosity, flocculation and gloss behavior and higher color strength, compared to untreated pigments.
• the addition compounds according to the invention can also be used as viscosity reducers and compatibilizers in synthetic resins.
• synthetic resins are the so-called “sheet molding compounds” (SMC) and “bulk molding compounds” (BMC), which consist of highly filler and fiber-containing unsaturated polyester resins.
• SMC sheet molding compounds
• BMC bulk molding compounds
• Their preparation and processing is described by way of example in DE-A-3643007.
• SMC and BMC resin blends is that often polystyrene (PS) is added to the formulation to reduce shrinkage during the processing process. PS is not compatible with the unsaturated polyester resins used and it comes to the separation of the components.
• PS polystyrene
• the additives according to the invention can, because of their good dispersing qualities, bring about compatibilization between PS and unsaturated polyester resin, which increases the storage stability and processing stability of such mixtures.
• the addition compounds according to the invention can in many cases, for example in incompatible polyol mixtures, polyol isocyanate mixtures or polyol blowing agent mixtures are used for polyurethane production, resulting from this incompatibility separation problems of the dispersions, in particular emulsions are completely or partially avoided ,
• the addition compounds according to the invention are added in an amount of preferably 0.01 to 10 wt .-%, based on the total amount of the preparations. Based on the solid to be dispersed, they are used in an amount of preferably 0.5 to 100 wt .-%. If solids which are difficult to disperse are used, the amount of added addition compound used according to the invention can certainly be higher.
• the amount of dispersant is generally dependent on the surface to be coated of the substance to be dispersed. For example, when titanium dioxide is used as a pigment, the amount of dispersant is less than in the case of, for example, carbon black. Generally, it can be said that for dispersing inorganic pigments less dispersant is necessary than for organic pigments, since the latter have a higher specific surface area and therefore a larger amount of dispersant is necessary.
• Typical dosages for inorganic pigments are 1-10 wt .-%, for organic pigments at 10-30 wt .-% (each active ingredient addition compound based on pigment). For very finely divided solids, for example having particle sizes below 100 nm (eg some carbon blacks), addition amounts of 30-80% by weight or more are necessary.
• a sufficient pigment stabilization for example color strength, gloss and transparency of the pigment dispersion or the degree of flooding (rub-out test) can be used in a white blend.
• the dispersion of the solids can be carried out as a single drive or as a mixed drive with multiple pigments simultaneously, with the best
• Results can usually be achieved in single-name auctions.
• the dispersants achieve their optimum effect when added to the millbase, especially when the first to be dispersed
• Solid is mixed only with the additive and optionally solvents ("premix"), since then adsorb the additive preferably on the solid surface without having to compete with the binder polymers. In practice, this procedure is only necessary in exceptional cases. If necessary, the addition compounds can also be used subsequently (as so-called "post-additives"), for example to solve flocculation or flocculation problems in a fully blended approach, but in this case increased additive dosages are generally required.
• the addition compounds of the invention may exert a more or less pronounced influence on the rheology of the system. They can therefore also be used in such cases for rheology control, optionally in combination with other rheological additives such as fumed silica, layered silicates (bentonites), hydrogenated castor oils or the additives BYK ® -410, BYK ® -420 and BYK ® -425 (BYK Chemie GmbH). Frequently, synergistic effects are observed. In many cases, the corrosion protection properties of coatings can also be improved by the use of the addition compounds according to the invention.
• pulverulent or fibrous solids are those which can be coated with dispersants, in particular organic and inorganic pigments which are used in paints, coating compositions, molding compositions or other plastics, inorganic or organic fillers which are used for filling or reinforcing paints, coating compositions , Molding compounds or other plastics are used.
• dispersants in particular organic and inorganic pigments which are used in paints, coating compositions, molding compositions or other plastics
• inorganic or organic fillers which are used for filling or reinforcing paints, coating compositions , Molding compounds or other plastics are used.
• a subset of such fillers are organic and / or inorganic fibers which are also used as fillers or reinforcing agents.
• pigments are mono-, di-, tri- and polyazo pigments, oxazine pigments, dioxazine pigments, thiazine pigments, diketo-pyrrolo-pyrroles, phthalocyanines, ultramarine and other metal complex pigments, indigoid pigments, diphenylmethane, triarylmethane , Xanthene, acridine, quinacridone, methine pigments, anthraquinone, pyranthrone, perylene and other polycyclic carbonyl pigments, carbon black based inorganic pigments, graphite, zinc, titanium dioxide, zinc oxide, zinc sulfide, zinc phosphate, barium sulfate, Lithophones, iron oxide, ultramarine, manganese phosphate, cobalt aluminate, cobalt stannate, cobalt zincate, antimony oxide, antimony sulfide, chromium oxide, zinc
• nanoscale organic or inorganic solids with particle sizes below 100 nm such as certain carbon black types or particles which consist of a metal oxide or semimetal oxide or hydroxide, and also particles which consist of mixed metal and / or metalloid oxides or consist of hydroxides.
• the oxides and / or oxide hydroxides of aluminum, silicon, zinc, titanium, and the like can be used to produce such extremely fine particulate solids.
• the production process of these oxide, hydoxide or oxide hydroxide particles can be carried out by a variety of methods such as, for example, ion exchange processes, plasma processes, sol-gel processes, precipitation, comminution (for example by grinding) or flame hydrolysis and the like.
• pulverulent or fibrous fillers are those which are composed of pulverulent or fibrous particles of aluminum oxide, aluminum hydroxide, silicon dioxide, kieselguhr, silica, quartz, silica gel, talc, kaolin, mica, perlite, feldspar, slate, calcium sulfate, barium sulfate, Calcium carbonate, calcite, dolomite, glass or carbon. Further examples of pigments or fillers can be found for example in EP-A-0 270 126. Flame retardants, such as e.g. Aluminum or magnesium hydroxide and matting agents such as e.g. Silicas can also be well dispersed and stabilized.
• the molecular weights or number average molecular weights M n are in the presence of titratable hydroxy or amino groups by end group determination on the
• the free NCO content of the polyisocyanates used and the reaction course of the NCO additions is determined according to EN ISO 9369 by reaction with butylamine and subsequent titration of the excess amine. These methods are also described in Saul Patai's "The Chemistry of Cyanates and their Thioderivates," Part 1, Chapter 5, 1977.
• hydroxy-functional caprolactone polyesters are prepared as described, for example, in EP 158678.
• Polyester from iso-decano! and epsilon-caprolactone (molar ratio 1: 8.3)
• Polyester from n-decanol and epsilon-caprolactone (molar ratio 1: 8,3)
• n-decanol and 857 parts of epsilon-caprolactone are homogenized, admixed with 0.02 part of DBTL and heated to 170.degree. It is stirred for about 6 hours at this temperature until a FK of 99% is reached.
• the product having a number average molecular weight M n of about 1100 g / mol is solid at room temperature and has an OH number of 51 mg KOH / g.
• Polyesters of 3-aminopropyltriethoxysilane and epsilon-caprolactone (molar ratio 1: 7,7)
• Polyesters of monophenylglycol and epsilon-caprolactone (molar ratio 1: 5.7)
• Polyesters of oleyl alcohol, epsilon-caprolactone and delta-valerolactone (molar ratio 1: 1, 08: 1, 08)
• Polyester of butoxypolypropylene glycol (with an average molecular weight of ca. 700), epsilon-caprolactone and delta-valerolactone (molar ratio 1: 10.5: 10.5)
• Example 2 Analogously to Example 1, instead of caprolactam 1, 45 parts of imidazole are used. The solids content is 52%. The amine number is 12 mg KOH / g.
• Example 2 Analogously to Example 1, 2.1 parts of 3,5-dimethylpyrazole are used instead of caprolactam. The solids content is 52%.
• Example 6 Analogously to Example 1, instead of caprolactam 1, 03 parts of 3,5-dimethylpyrazole are used. After it has reacted, 1.36 parts of API (aminopropylimidazole) are added. The solids content is 52%. The amine number is 6 mg KOH / g. Example 6
• Example 2 Analogously to Example 1, 0.93 parts of 2-butanone oxime are used instead of caprolactam. After it has reacted, 1.36 parts API are added. The solids content is 52%. The amine number is 6 mg KOH / g.
• Example 2 As in Example 1, 0.73 parts of imidazole are used instead of caprolactam. After it has reacted, 1.35 parts of API are added. The solids content is 52%. The amine number is 12 mg KOH / g.
• Example 2 Analogously to Example 1, 1.2 parts of caprolactam are used instead of 2.4 parts of caprolactam. After it has reacted, 1.35 parts of API are added. The solids content is 52%. The amine number is 6 mg KOH / g.
• Example 2 Analogously to Example 1, 3.2 parts of triethanolamine are used instead of caprolactam. The product is medium viscosity. The solids content is 52%. The amine number is 10 mg KOH / g and the OH number is 27 mg KOH / g.
• Example 11 Analogously to Example 1, 2.5 parts of N-methyldiethanolamine are used instead of caprolactam. The product is medium viscosity. The solids content is 52%. The amine number is 12 mg KOH / g. Example 11
• Example 2 Analogously to Example 1, 2.8 parts of aminopropylmethyl ethanolamine are used instead of caprolactam. The product is highly viscous. The solids content is 52%. The amine number is 13 mg KOH / g and the OH number is 12 mg KOH / g.
• Example 2 Analogously to Example 1, 3.1 parts of 3- (diethylamino) propane-1, 2-diol are used instead of caprolactam. The product is highly viscous. The solids content is 52%.
• Example 2 Analogously to Example 1, 2.1 parts of triethanolamine are used instead of caprolactam. The product is highly viscous. The solids content is 52%. The amine number is 7 mg KOH / g.
• NCO groups are implemented. Then it is treated with 1.40 parts of 3,5-dimethylpyrazole and stirred at 90 ° C. until the remaining NCO groups have reacted. The solids content is 30%.
• Shielding gas is heated to 60 ° C and added 0.001 parts of DBTL. After 0.75
• NCO groups is implemented. Then it is mixed with 3.3 parts of triethanolamine and stirred at 70 0 C until the remaining NCO groups are reacted.
• the product is medium viscosity, has a solids content of 52%, an amine value of 11 mg
• Example 9 1000 parts of Example 9 are mixed with 23 parts of maleic anhydride (MSA). When heated under inert gas, the MSA dissolves. It is stirred for 4 hours at 80 0 C. Then 21 parts of PMA are added and cooled. The final product has a solids content of 52%, an acid number of 13 mg KOH / g, an amine value of 10 mg KOH / g and an OH number of 13 mg KOH / g.
• Example 25 non-inventive comparative example
• polyisocyanate P1 28.1 parts are homogenized with 22.8 parts of intermediate A5, 12.5 parts of A7 and 34 parts of PMA. Under inert gas is heated to 80 0 C and 0.003 parts DBTL added. It is stirred for about 1 hour at this temperature until 60% of the NCO groups used are reacted. Then, a mixture of 1, 5 parts of N, N-dimethylaminopropane and 2 parts of triethanolamine is added and further stirred at 80 0 C until all NCO groups have reacted. The product has a solids content of 52%.
• P1 Aromatic TDI polyisocyanurate having a free NCO content of 8.0% as a 51% solution in butyl acetate, e.g. Desmodur®IL, Bayer AG
• P2 Aliphatic polyisocyanate (HDI trimer) having a free NCO content of 21.8%, e.g. Desmodur® N3300, Bayer AG
• P3 Aromatic TDI polyisocyanurate with a free NCO content of 8.0%; as a 51% solution in ethyl acetate, eg Desmodur® IL EA, Bayer AG
• Alkyd resin 70% in Solventnaphta; For example: manufacturer Vianova, Vialkyd AC 451 56 parts
• Pendulum hardness Pendulum hardness according to König Cross-hatch Cross-cut multi-blade knife Assessment according to DIN EN ISO 2431
• Alkyd resin 60% in Solventnaphta; For example: manufacturer Vianova, Vialkyd AC 451 74.0 parts
• Laropal A81 (aldehyde resin, BASF), 65% in PMA 25, 0 part PMA (methoxypropyl acetate) 3.0 parts
• Addition compound 11 5 parts iron oxide red, e.g. Bayferrox red 130M 60, 0 parts silica, e.g. Aerosil 200 0, 5 parts
• Pigment Red 170 e.g. Novopermrot F3RK70 40.0 parts
• Titanium dioxide e.g. Kronos 2160 65.0 parts
• Dispersion Dispermat CV / 30 min / 8000 rpm / 40 0 C / 1 mm beads 1: 1
• Addition compound according to the invention 19.60 parts Carbon black, eg Spezialschwarz 4 (Degussa AG) 34.00 parts 10000 parts + 10% PMA
• Dispersion Dispermat CV / 60 min./ 10000 U / min / 40 0 C / 1 mm beads 1: 1

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