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
  • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
  • C08G18/72—Polyisocyanates or polyisothiocyanates
  • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
  • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
  • C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
  • C08G18/7621—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
• • 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
  • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
  • C08G69/48—Polymers modified by chemical after-treatment
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/08—Processes
  • C08G18/16—Catalysts
  • C08G18/22—Catalysts containing metal compounds
  • C08G18/24—Catalysts containing metal compounds of tin
  • C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
  • C08G18/246—Catalysts containing metal compounds of tin tin salts of carboxylic acids containing also tin-carbon bonds
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/40—High-molecular-weight compounds
  • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
  • C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
  • C08G18/423—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing cycloaliphatic groups
  • C08G18/4233—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing cycloaliphatic groups derived from polymerised higher fatty acids or alcohols
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/40—High-molecular-weight compounds
  • C08G18/48—Polyethers
  • C08G18/50—Polyethers having heteroatoms other than oxygen
  • C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
  • C08G18/5024—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino groups
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/40—High-molecular-weight compounds
  • C08G18/60—Polyamides or polyester-amides
  • C08G18/603—Polyamides
• • 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
  • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
  • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
  • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
  • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
  • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
  • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
  • C08G18/72—Polyisocyanates or polyisothiocyanates
  • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
  • C08G18/78—Nitrogen
  • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
  • C08G18/798—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing urethdione groups
• • 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
  • C08G18/8064—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with monohydroxy compounds
• • 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
  • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
  • C09D7/40—Additives
  • C09D7/65—Additives macromolecular

Definitions

• Aqueous formulations play a significant role in a wide variety of applications.
• the rheological properties of these aqueous formulations play a crucial role.
• These rheological properties are typically controlled by rheology control agents, also referred to herein as rheology additives.
• Rheology control agents are generally suitable for increasing the viscosity
• Coating can be applied to substrates.
• Rheology control agents play a significant role.
• Such effect pigments are, for example, metallic effect pigments, such as, for example, aluminum pigments, brass pigments,
• the effect pigments also include, for example, interference pigments or pearlescent pigments such as, for example, metal oxide mica pigments, fish silver, bismuth oxychloride or basic lead carbonate.
• interference pigments or pearlescent pigments such as, for example, metal oxide mica pigments, fish silver, bismuth oxychloride or basic lead carbonate.
• Rheology control agents are used. In general, it is believed that these would, in the ideal case, exert their effect by setting a suitable minimum viscosity as well as a pseudoplastic flow behavior and also by corresponding elastic proportions; In addition to the actual orientation of the pigments, a uniform layer thickness and the distribution of the pigments in the matrix are of decisive importance here.
• Excipients used for example, clay minerals, silicic acids, special polyamides or polysaccharide-based thickeners.
• a disadvantage of the use of these rheological auxiliaries is that they are usually present in the form of dry solids. Consequently, said rheological excipients are first digested to a semifinished product prior to use using shear forces. However, this is often undesirable because associated with additional effort. In addition, the handling of dry, powdery products that can cause dusts during processing, undesirable.
• US 2012/125235 describes combinations of specific polyamides with amide waxes and / or hydrogenated castor oil. On the one hand, due to their consistency, corresponding combinations are usually difficult to handle and incorporate (especially in aqueous media), on the other hand it is known that, for example
• EP 0 877 063 describes the use of special neutralized polyamides, which are used here as an aqueous dispersion as anti-settling agents. Even with these products, the performance properties, for example, in terms of incorporation or quality of the achieved pigment orientation - often not enough. Often For example, corresponding additives can be handled only as low-percentage semi-finished products and with corresponding effort.
• Acidic polyamides as anti-settling agents are described, for example, in JP 2005 171 155 A and WO 201 1/052707 A1.
• EP 1 188 779 A1 discloses rheologically active urea-urethane solutions. These often allow a strong thixotropic behavior, but often show limitations in terms of pigment orientation.
• Associative thickeners for example, so-called polyurethane thickeners, which act associatively via hydrophobic interactions.
• their behavior is highly system specific, is often affected by other system components (for example cosolvents or wetting and dispersing additives), and in many cases does not have the desired properties, e.g. in terms of elasticity.
• the object of the present invention was, in particular, to provide an improved correspondingly high-quality, well-effective
• Rheology control agent with improved properties, especially with regard to the anti-sedimentation effect and the pH-independence of the effect.
• preparations according to the invention are coating agents, they should, in addition to the advantages already mentioned, have improved properties with regard to pigment orientation, in particular with respect to coating agents which are not additized according to the invention
• the additives according to the invention additionally allow an improved flop behavior corresponding coatings. Further improvements are the following
• radicals R1 are independently selected from the group consisting of
• Hydrocarbon radicals having from 6 to 40, preferably 6 to 24, particularly preferably 6 to 13, very particularly preferably 6 to 10 carbon atoms, which optionally contain one or more isocyanurate groups; the radicals R 3 are independently (k + 1) -valent organic radicals which are selected from the group consisting of saturated or unsaturated, preferably saturated, linear or
• branched, aliphatic hydrocarbon radicals having 2 to 40, preferably 2 to 20, more preferably 2 to 8, and most preferably 2 to 4
• Aromade radicals wherein the aromatic hydrocarbon radicals optionally carry one or more linear or branched alkyl substituents having 1 to 10, preferably 1 to 4 carbon atoms; Araliphatic hydrocarbon radicals having 8 to 40, preferably 8 to 20, particularly preferably 8 to 12 and very particularly preferably 8 to 10
• radicals R4 are independently of one another divalent organic radicals which are selected from the group consisting of saturated or unsaturated, preferably saturated, linear or
• radicals R5 independently of one another are divalent organic radicals which are selected from the group consisting of saturated or unsaturated, preferably saturated, linear, branched or cyclic, preferably linear, aliphatic hydrocarbon radicals
• the Hydrocarbon radicals optionally contain ether oxygen atoms and / or tertiary amino groups; araliphatic hydrocarbon radicals having 8 to 40, preferably 8 to 32, particularly preferably 8 to 24 and very particularly preferably 8 to 18 or 8 to 16 or 8 to 12 carbon atoms; aromatic hydrocarbon radicals having from 6 to 40, preferably 6 to 32, more preferably 6 to 24 and most preferably 6 to 18 or 6 to 16 or 6 to 12 carbon atoms; the radicals R6 are selected from the group of the aromatic radicals having 6 to 40, preferably 6 to 32, particularly preferably 6 to 24 and very particularly preferably 6 to 18 or 6 to 16 or 6 to 12 carbon atoms or very particularly preferably as the radicals R4 are defined and chosen independently of them; the radicals E independently is COOH or COO ® ® Z, very particularly preferably represent COOH, wherein Z ®
• substituted ammonium ions whose organic substituents are preferably selected from the group of alkyl radicals having 1 to 24 carbon atoms, aryl radicals having 6 to 24 carbon atoms, alkylaryl radicals having 7 to 25 carbon atoms, where the alkyl radicals, aryl radicals and alkylaryl radicals optionally carry one or more hydroxyl groups and alkaline earth metal cations, preferably calcium and / or magnesium, or wherein Z ® is omitted when Z5 is a protonated or quaternized amino group, and
• the radicals Z5 independently of one another for an amide group, preferably
• m is 1 to 5, preferably 1 or 2, more preferably 1;
• n is 1 to 12, preferably 1 to 6, more preferably 1 to 4 or 1 to 3 and most preferably 1 or 2;
• k is 1 to 5, preferably 1 to 4, more preferably 1 to 3, even more preferably 1 or 2 and most preferably 1.
• indices m, n, k and v are integers for the individual defined species, as usual. When looking at the totality of the species, especially in molecularly disparate species, for example at higher values for v, these indices represent number average values of the sum of all the individual species.
• hydrocarbon radicals when referring to hydrocarbon radicals, as used in the usual definition, this means that the radicals are composed of only carbon and hydrogen. Where these radicals may optionally additionally contain heteroatoms such as ether oxygen atoms, hydroxyl groups or tertiary amino groups, this is explicitly stated. In the event that a hydrocarbon radical may contain further carbon- and heteroatom-containing radicals, such as, for example, isocyanurate groups, this is likewise stated explicitly. Contains one
• R1 is selected from the group consisting of
• R a is a linear or branched alkyl or alkenyl radical having 1 to 18 carbon atoms
• R b is one or more radicals from the group consisting of C 2 H 4, C ⁇ He and C4H8 and v is an integer from 1 to 25.
• R1 is selected from the group consisting of
• Radicals from the group consisting of C2H4 and C3H6 and v is an integer from 1 to 15.
• R2 is selected from the group consisting of
• R3 is selected from the group consisting of
• k stands for an integer 1, 2 or 3.
• R4 is selected from the group consisting of linear or branched alkylene or alkenylene radicals having from 4 to 40 carbon atoms. Most preferably, R4 is selected from the group consisting of branched alkylene or alkenylene radicals having 30 to 38 carbon atoms, wherein Z4 and Z5 are each an amide group.
• R 5 is selected from the group consisting of linear or branched alkylene radicals having 2 to 13 carbon atoms, cycloalkylene radicals 3 to 13 carbon atoms and arylalkylene radicals having 7 to 13 carbon atoms.
• R 5 is selected from the group consisting of linear or branched alkylene radicals having 4 to 8 carbon atoms, cycloalkylene radicals 4 to 8 carbon atoms and arylalkylene radicals having 7 or 8 carbon atoms.
• R6 is selected from the aforementioned R4 preferred groups.
• the number-average molecular weight of the species of the general formula (I) is preferably from 1000 to 7500 g / mol, more preferably from 1400 to 4000 g / mol, very particularly preferably from 1600 to 3800 g / mol, better still 2000 to 3000 g / mol.
• the rheology control agents of the invention contain or consist of one or more of the species of general formula (I). As inventive Rheology control agents are referred to the reaction products obtained by the process of the invention. Ideally, these consist of one or more of the species of general formula (I).
• the rheology control agents of the invention are components of those described below
• Rheology control agent compositions the latter generally containing solvents, in particular polar, aprotic solvents and optionally ionogenic compounds, in particular salts. Both the rheology control agents and the rheology control agent compositions are typically included
• the rheology control agent compositions are the usual forms of storage and delivery of the additives.
• Rheology control agent as described below by reacting a group-containing and / or urethane group-containing building block (A) with a
• amide group-containing building block (B) produced.
• the definitions of the radicals and indices in the building blocks (A) and (B) and the species used in their preparation correspond to the definitions as in formula (I) and their preferred
• starting compounds and end products has the same meaning. The same applies to the preferred selections of the radicals and groups or the preferred number ranges of the indices. If, in exceptional cases, another preference is given, this is indicated accordingly.
• the building block (A) has a group reactive toward alcohols and / or amines, which is preferably an isocyanate group (alternative (A1)) or uretdione group (alternative (A2)).
• R1 -X-H (III) in which X is O or N (R7), where R7 is H, an alkyl radical having 1 to 12
• X is oxygen and m is 1 to 4, more preferably 1 or 2, and most preferably m is 1.
• diisocyanates examples include 1,4-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, 2,2,4-trimethyl-1,6-hexamethylene diisocyanate, 1,1,10-decamethylene diisocyanate, 1,4-cyclohexylene diisocyanate, p-phenylene diisocyanate, Phenylene diisocyanate, 2,6-tolylene diisocyanate, 2,4-tolylene diisocyanate and mixtures thereof, p- and m-xylylene diisocyanate, 1,5-naphthylene diisocyanate,
• Isophorone diisocyanate 4-4 ', - diisocyanatodicyclohexylmethane, 3,3'-dimethyl-4,4'-bisphenylene diisocyanate, 3,3'-dimethyl-diisocyanatodiphenylmethane, the
• Particularly preferred isocyanates are tolylene diisocyanate (TDI) and
• Isophorone diisocyanate also in combination or as a mixture of its isomers, in particular as a mixture of 2,4-TDI and 2,6-TDI.
• IPDI Isophorone diisocyanate
• the preparation of such preferred monoadducts from a diisocyanate and a monoalcohol or monoamine is also described, for example, in EP 1 188 779 A1.
• Carbon atoms, an aryl radical having 6 to 12 carbon atoms or an alkylaryl radical having 7 to 12 carbon atoms, while maintaining the uretdione function to corresponding uretdione-functional urethanes or ureas are implemented.
• X is oxygen, so that the free isocyanate groups react to urethane groups.
• urethane groups react to urethane groups.
• urethane groups react to urethane groups.
• isocyanate-functional uretdiones are the dimers of
• Hexamethylene diisocyanate, TDI and IPDI Hexamethylene diisocyanate, TDI and IPDI.
• the group R d preferably represents a radical selected from the group consisting of alkyl groups, alkenyl groups or alkylaryl groups, in particular methyl, ethyl, n-propyl, isopropyl, allyl, n-butyl, sec-butyl, t Butyl, benzhydryl and benzyl group and trialkylsilyl groups, in particular the trimethylsilyl group.
• E ' is a group E, most preferably a group COOH.
• the amide group-containing building block (B) is preferably prepared in one of the following ways.
• alkyl radical having 1 to 12 carbon atoms which optionally contains one or more ether oxygen atoms and / or carries one or more hydroxyl groups, an aryl radical having 6 to 12 carbon atoms,
• alkylaryl radical having 7 to 12 carbon atoms, or less preferably a radical -R3 '[- Z2-R2- [Z1 -R1] m -] k -,
• R3 ' is a (k' + 1) -valid organic radical, which is otherwise defined as radical R3,
• R1, R2, Z1 and Z2 are as defined in formula (I),
• k 1 to 4
• k ' 1 to 4
• H 2 C C (R f ) -E '(X) where R is hydrogen or an alkyl radical having 1 to 2 carbon atoms, particularly preferably hydrogen, in such a stoichiometric ratio that the resulting amido-containing building block (B ) contains exactly one end group E '.
• the dicarboxylic acids are preferably aliphatic, cycloaliphatic or aromatic, linear or branched, saturated or unsaturated dicarboxylic acids having at least 2, more preferably 3 to 40 carbon atoms.
• dicarboxylic acids examples include adipic acid, oxalic acid, malonic acid,
• Succinic acid glutaric acid, pimelic acid, suberic acid, sebacic acid, azelaic acid, undecanedioic acid, 1,1,1-undecanedicarboxylic acid, dodecanedioic acid, hexadecanedioic acid, docosenedioic acid maleic acid, fumaric acid, terephthalic acid or isophthalic acid, alone or used in mixtures.
• Acid anhydrides such as maleic anhydride, glutaric anhydride, phthalic anhydride and succinic anhydride, which are optionally modified with alkyl or alkylene groups such.
• Dodecenylsuccinic anhydride are also included in the invention.
• Polymeric dicarboxylic acids such as the dicarboxylic acid of polybutadiene can be used as well as hydroxy-functional dicarboxylic acids such. Tartaric acid,
• dimerized fatty acids known in the art as dimer acids, are known as
• Dicarboxylic acids for the preparation of the additives of the invention are preferred. These dimer acids can have both a low monomer content and a proportion of preferably not more than 5 percent by weight of trimer acid.
• Suitable oligomerized fatty acids are preferably dimers of unsaturated monocarboxylic acids, wherein the monocarboxylic acids are usually 10 to 28
• Carbon atoms preferably 12 to 24 carbon atoms, more preferably 14 to 20 carbon atoms, and most preferably 16 to 18 carbon atoms.
• oligomerized fatty acids are preferably dimers of unsaturated long-chain monocarboxylic acids, the long-chain monocarboxylic acids usually having 10 to 28 carbon atoms, preferably 12 to 24 carbon atoms, more preferably 14 to 20 carbon atoms and most preferably 16 to 18 carbon atoms, with unsaturated short chain monocarboxylic acid, wherein the short-chain monocarboxylic acids have 3 to 9 carbon atoms.
• a typical example of such a dimer is 5- (or 6) carboxy-4-hexylcyclohex-2-ene-1-octanoic acid, a monocyclic dicarboxylic acid having 21 carbon atoms.
• Preferred fatty acids for the preparation of the dimer acids are e.g. Tall oil fatty acid, oleic acid, tallow fatty acids, linoleic acid, linolenic acid (cis and trans isomers),
• Tetracosahexaenoic acid (nisic acid), ⁇ -elaeostearic acid, ⁇ -elaeostearic acid, o calendulic acid, ⁇ -calendulic acid, crepenoic acid, dihomo-v-linolenic acid,
• Tetracosapentaenoic acid 5-dodecenoic acid, 7-tetradecenoic acid, palmitoleic acid, cis-13-eicosenoic acid, vaccenic acid, 15-docosenoic acid, 1-tetracenoic acid, elaidic acid, cis-1-eicosenoic acid, metic acid, erucic acid, nervonic acid.
• Suitable hydroxy-functional unsaturated fatty acids for the preparation of dimer acids are dimorphic acid, densipolic acid and lesquerolic acid.
• R4 is a hydrocarbon radical having 30 to 34 carbon atoms.
• the radicals Y and Y ' are each one
• R6 is defined as R4, most preferably identically R4 is.
• R4 is a hydroxyl group and the radical E 'is a group COOH.
• the diamines H2N-R5-NH2 are preferably ethylenediamine
• diamines are those containing ether oxygen atoms, such as 4,7-dioxadecane-1, 10-diamine, 4.1-dioxatetradecane-1, 14-diamine, 4,7,10-trioxadecane-1,13 -diamine, polyoxyalkylene-diamines which ethylene oxide and / or propylene oxide groups, arranged randomly or in blocks, have a number average molecular weight of 148 to 4000 g / mol and, for example as Jeffamine® D 230, D 400, D 2000, D 4000 and Jeffamine® ED 600, ED 900, ED 2003 and EDR 148 are available from Huntsman, Polytetrahydrofurandiamine such. Bis (3-aminopropyl) polytetrahydrofuran 350, 750, 1100 and 2100 (numbers indicate approximate molecular weight).
• ether oxygen atoms such as 4,7-dioxadecane-1, 10-diamine,
• An alkylene radical is one example of which is N, N'-bis (3-aminopropyl) methylamine.
• Mono amino alcohols with primary amino group used such as 2-aminoethanol, 3-amino-1-propanol, 1-amino-2-propanol, 2- (2-aminoethoxy) ethanol, 2-ethyl-2-amino-1, 3-propanediol and 2-amino-2-hydroxymethyl-1,3-propanediol.
• monoamino alcohols having a secondary amino group such as diethanolamine, 3- (2-hydroxyethylamino) -1-propanol or
• Diisopropanolamine find use.
• Particularly preferred species of the general formula (HX) k-R3-NH (R8) are the following monoamino alcohols with primary
• Used amino group 2-aminoethanol, 3-amino-1-propanol, 1-amino-2-propanol, 2- (2-aminoethoxy) ethanol and 2-amino-2-hydroxymethyl-1, 3-propanediol, including 2-aminoethanol, 3-amino-1-propanol, 1-amino-2-propanol, 2- (2-aminoethoxy) ethanol and 2-amino-2-hydroxymethyl-1, 3-propanediol, including 2-aminoethanol, 3-amino-1-propanol, 1-amino-2-propanol, 2- (2-aminoethoxy) ethanol and 2-amino-2-hydroxymethyl-1, 3-propanediol, including 2-aminoethanol, 3-amino-1-propanol, 1-amino-2-propanol, 2- (2-aminoethoxy) ethanol and 2-amino-2-hydroxymethyl-1, 3-propanediol, including 2-aminoethanol, 3-
• R 8 is preferably H, or an alkyl radical having 1 to 12 carbon atoms which optionally contains one or more ether oxygen atoms and / or carries one or more hydroxyl groups,
• alkylaryl radical having 7 to 12 carbon atoms, or less preferably a radical -R3 '[- Z2-R2- [Z1 -R1] m -] k-,
• R3 ' is a (k' + 1) -valid organic radical, which is otherwise defined as radical R3,
• R1, R2, Z1 and Z2 are as defined in formula (I),
• k 1 to 4
• k ' 1 to 4
• H 2 C C (R f ) -E '(X) where R is hydrogen or an alkyl radical having 1 to 2 carbon atoms, particularly preferably hydrogen, in such a stoichiometric ratio that the resulting amido-containing building block (B ) contains exactly one end group E '.
• R7 is hydrogen, by ring-opening polymerization (a) in the presence of one or more species of general formula (XII)
• X is as defined in formula (III) and is preferably oxygen
• R 8 is preferably H, or
• alkyl radical having 1 to 12 carbon atoms which optionally contains one or more ether oxygen atoms and / or one or more
• alkylaryl radical having 7 to 12 carbon atoms, or less preferably a radical -R3 '[- Z2-R2- [Z1 -R1] m ⁇ ] k ⁇ ,
• R3 ' is a (k' + 1) -valid organic radical, which is otherwise defined as radical R3,
• R1, R2, Z1 and Z2 are as defined in formula (I),
• H 2 C C (R f ) -E '(X) where R is hydrogen or an alkyl radical having 1 to 2 carbon atoms, particularly preferably hydrogen, in such a stoichiometric ratio that the resulting amido-containing building block (B ) contains exactly one end group E '.
• the building block (A) is prepared by the process (A1) and the building block (B) by the process according to (B1 (a)) and the building blocks are subsequently converted to a species of the general formula (Ia), and if E 'is COOR d , E' is converted to E; or
• the building block (A) is prepared by the process (A1) and the building block (B) by the process according to (B1 (b)) and the building blocks are subsequently converted into a species of the general formula (Ia), and if E 'is COOR d , E' is converted to E; or
• the building block (A) is prepared by the process (A1) and the building block (B) by the process according to (B2 (a)) and the building blocks are subsequently converted into a species of the general formula (Ia), and if E 'is COOR d , E' is converted to E; or
• the building block (A) is prepared by the process (A1) and the building block (B) by the process according to (B2 (b)) and the building blocks are subsequently converted to a species of the general formula (Ia), and if E 'is COOR d , E' is converted to E; or
• the building block (A) is prepared by the process (A1) and the building block (B) by the process according to (B3 (a)) and the building blocks are subsequently converted into a species of the general formula (Ia), and if E 'is COOR d , E' is converted to E; or
• the building block (A) is prepared by the process (A1) and the building block (B) by the process according to (B3 (b) (c)) and the building blocks are subsequently converted into a species of the general formula (Ia) and if E 'is COOR d , E' is converted to E; or
• one or more species resulting from process (A1) and / or process (A2) can be reacted with one or more species resulting from process (B1), process (B2) and / or process (B3). If E 'for COOR d where R d is a protective group, the protective group is then split off, wherein E 'is optionally converted to E with salinization.
• Processes (i) and (ii) are particularly preferred, and process (i) is very particularly preferred.
• process sequence (i) is preferred in which the species of the general formulas (VI) and (Via) are identical and the stoichiometry of the components is selected such that in the preparation of building block (B) obtained by the process (B1) directly a building block with the terminal remainder -R6-E arises, that is, that the
• Process steps B1 (a) and B1 (b) are omitted.
• Rheology control agent in liquid form, preferably in lower
• liquid form is broadly understood herein to include, for example, any liquid form from thin viscous to viscous to pasty or gelatinous
• rheology control agent compositions of this invention containing rheology control agents are also included
• Rheology control agent in a solvent Suitable solvents are all known organic solvents, such as alcohols, esters, aliphatic and aromatic hydrocarbons, halogenated
• Solvent in particular polar aprotic solvents.
• Rheology control agent compositions as a solution in aprotic organic solvents.
• Particularly suitable are polar, aprotic organic solvents, very particularly preferably those which are selected from the group of amides, lactams, Sulfoxides and ionic liquids (that is, organic salts with a
• Particularly preferred polar, aprotic organic solvents are substituted or unsubstituted, preferably unsubstituted N-alkylbutyrolactams, dialkylsulphoxides, substituted or unsubstituted amides, in particular carboxamides.
• N-alkylbutyrolactams are N-methylbutyrolactam, N-ethylbutyrolactam, N-
• Octyl butyrolactam and N-hydroxyethyl butyrolactam An example of a dialkyl sulfoxide is dimethylsulfoxide.
• Examples of amides are ⁇ , ⁇ -dimethylformamide, N, N-dimethylacetamide, ⁇ , ⁇ -dialkylamidoalkyl ester, N, N-dialkylamidoalkyl ether,
• Preferred ionic liquids suitable as solvents are substituted imidazolium salts, e.g. 1-ethyl-3-methylimidazolium acetate, 1-ethyl-3-methylimidazolium acetate, 1-ethyl-3-methylimidazolium ethylsulfate, 1-butyl-3-methylimidazolium ethylsulfate, 1-ethyl-3-methylimidazolium thiocyanate and 1-butyl-3-methylimidazolium thiocyanate.
• substituted imidazolium salts e.g. 1-ethyl-3-methylimidazolium acetate, 1-ethyl-3-methylimidazolium acetate, 1-ethyl-3-methylimidazolium ethylsulfate, 1-butyl-3-methylimidazolium ethylsulfate, 1-ethyl-3-methylimidazolium thio
• Preferred solvents include dimethylsulfoxide and especially those N-alkylbutyrolactams whose nitrogen-bonded alkyl radical is linear or branched, preferably linear and the alkyl radical contains 1 to 20 or preferably 1 to 16, more preferably 1 to 12 and most preferably 3 to 10 carbon atoms, and also N, N-dimethylamidoalkyl esters, ⁇ , ⁇ -dimethylamidoalkyl ethers, formylmorpholine and acetylmorpholine.
• salts that is to say ionogenic compounds.
• These are preferably salts of cations of main groups I and II of the Periodic Table of the Elements (alkali metals and alkaline earth metals) or ammonium salts, preferably lithium, calcium or magnesium salts, more preferably lithium or calcium salts.
• Preferred anions are monovalent anions, more preferably halide, pseudohalide, Formate, acetate and / or nitrate, most preferably chloride, acetate and / or nitrate.
• the rheological control agent compositions according to the invention comprise, in addition to one or more of the urea- and / or urethane-substituted amides of the formula (I) or the rheology control agents according to the invention or an organic solvent prepared by the invention, preferably a polar, aprotic organic solvent and, if appropriate one or more ionic compounds.
• organic solvent preferably a polar, aprotic organic solvent and, if appropriate one or more ionic compounds.
• Solvents and ionic compounds are in particular the abovementioned, under the heading "Storage and delivery forms of the inventive
• the rheology control agent compositions according to the invention each based on the total weight of
• the aforesaid rheological control agent composition consists of the aforementioned constituents (i), (ii) and (iii), the percentage figures of the widest ranges for (i), (ii) and (iii) or preferred ranges or particularly preferred ranges add up or very particularly preferred ranges in each case to 100 wt .-%.
• the solvent is a polar, preferably aprotic, organic solvent, which in turn
• N-alkyl butyrolactams is preferably selected from the group consisting of N-alkyl butyrolactams, dialkyl sulfoxides and carboxylic acid amides.
• the ionogenic compound is a salt which is preferably selected from the group consisting of
• the rheology control agent compositions according to the invention particularly preferably contain, in each case based on the total weight of the
• the rheology control agent compositions according to the invention very particularly preferably contain, in each case based on the total weight of the
• the rheology control agent compositions according to the invention most preferably contain, in each case based on the total weight of the
• the rheology control agents according to the invention are preferably suitable for
• Aqueous systems are those which contain water as the main solvent or even as the sole solvent.
• aqueous systems are those which contain less than 35% by weight, more preferably less than 25% by weight, most preferably less than 20% by weight of organic solvents, based on the sum of
• aqueous systems may contain water-soluble organic or inorganic substances, for example salts, in particular the contained in the previous section ionogenic compounds.
• the invention also relates to the use of the formulations according to the invention for the rheology control of a liquid composition.
• Composition is preferably as a coating agent, in particular as a lacquer, as a plastic formulation, as a pigment paste (for example, effect pigment paste), as
• Sealant formulation as a cosmetic, as a ceramic formulation, as
• Adhesive formulation as liquid formulations for use in the gas and
• Oil extraction as a liquid formulation for the manufacture of electrical components and circuits (e.g., so-called "printed electronics"), as a liquid formulation for use in energy storage media (e.g., batteries), as a cleaning agent, as
• Potting compound as a building material formulation, as a lubricant, as a filler, as a wax emulsion, as a metalworking fluid (metal working fluid), in the form of a spray (eg. As so-called. Deposition Aid in pesticides), as an ink or as an ink, for example as an inkjet ink , in front.
• the present invention relates to a liquid composition useful as a coating agent, as a plastic formulation, as a pigment paste (e.g.
• Ceramic formulation as an adhesive formulation, as liquid formulations for use in gas and oil extraction, as a liquid formulation for the production of electrical components and circuits, as a liquid formulation for use in
• Energy storage media as a cleaning agent, as potting compound, as
• Building material formulation as a lubricant, as a filler, as a wax emulsion, as a metalworking fluid, in the form of a spray, as an ink or as an ink and which are preferably 0.1 to 7 wt .-% of the inventive
• Rheology control agent based on the total weight of the formulation contains.
• the invention relates to a liquid composition (ie
• Formulation which 0.2 to 5 wt .-%, particularly preferably 0.3 to 3 wt .-%, based on the total weight of the liquid composition including the rheology control agent according to the invention.
• the preparation according to the invention as rheology control agent for the rheology control of paints, printing inks, inks (such as, for example, inkjet inks), plastic formulations, cosmetic preparations,
• Detergents building material formulations, metalworking fluids, Lubricants, lubricants and / or adhesives, as well as formulations used in natural gas and petroleum extraction.
• the paints, printing inks and inks, in particular inkjet inks are preferably water-based paints, printing inks and inks, in particular inkjet inks.
• Coatings can be used in a wide variety of fields, including automotive coatings, building coatings, protective coatings, and others for painting ships and bridges, can and coil coating paints, and wood and furniture coatings.
• Resists which are used for color filters, for example in liquid crystal displays.
• the paint application also includes pasty materials, which usually have a very high proportion of solids and a small proportion of liquid
• pigment pastes or pastes based on effect pigments such as metallic effect pigments, such as
• the effect pigments also include, for example, interference pigments or pearlescent pigments, for example metal oxide mica pigments, fish silver, bismuth oxychloride or basic lead carbonate.
• the plastic formulations can be (liquid) starting materials for the production of plastic materials which are preferably converted by a chemical crosslinking process ("curing" into a thermoset)
• Preferred plastic formulations are unsaturated polyester resins, vinyl ester resins, acrylate resins, epoxy resins, Polyurethane resins, formaldehyde resins (such as melamine-formaldehyde or urea-formaldehyde) These can be cured under a wide variety of conditions, for example at room temperature (cold-curing systems) or at elevated temperature (hot-curing systems), optionally also under pressure ("closed mold”). Application, Sheet Molding Compound or Bulk Molding Compound).
• the plastic formulations also include PVC plastisols.
• the liquid starting material is hydrous or in a very polar organic medium.
• the cosmetic preparations may be varied, preferred
• water-based, liquid compositions that are used in the so-called personal care or health care sector, such as lotions, creams, pastes such as toothpaste, foams such as shaving cream, gels such for example, shaving gel, shower gel or pharmaceuticals in gel formulation, hair shampoo, liquid soaps, nail polishes, lipsticks and hair dyes.
• wax emulsions are preferably dispersions of solid waxes at room temperature in particulate form in water or an organic medium.
• the building material formulations may be liquid or pasty materials used in construction, which are used in the construction sector and are preferably aqueous and solidify upon curing, e.g. hydraulic binders such as concrete, cement, mortar, tile adhesive and gypsum.
• hydraulic binders such as concrete, cement, mortar, tile adhesive and gypsum.
• the metalworking fluids may preferably be water-based systems. Examples include cutting fluids, drilling fluids (as used in metalworking), release agents (often in the form of aqueous emulsions, for example, for aluminum die casting and foundry applications), foundry washes, and foundry coatings Liquids for the surface treatment of metals (for example, "surface finishing", surface cleaning and galvanization).
• the lubricants are - preferably water-based - agents which are used for lubrication, that is, the reduction of friction and wear, and the power transmission, cooling, vibration damping,
• the liquid formulations for use in the gas and oil extraction are preferably water-based liquids that are used in the development of a deposit or in the subsequent exploitation of the same.
• Drilling fluids also known as drilling muds or drilling fluids, are preferred here.
• An area of application for corresponding aqueous formulations For example, the so-called. "Hydraulic fracturing”.
• Another field of application are oil-based drilling mud.
• Detergents can be used to clean a wide variety of objects. They cause or assist the removal of impurities, residues and
• Detergents also include detergents (mainly for cleaning textiles, their precursors and leather), detergents and detergents, and personal care products.
• the adhesives can be all process materials which are liquid under processing conditions and which can join the adherends by means of surface adhesion and internal strength. Preference is given here to water-based adhesives. In the following, the invention is illustrated by examples.
• the number average molecular weight is the number average molecular weight distribution determined by gel permeation chromatography (GPC). The molecular weight distribution was determined according to DIN 55672 Part 1: 2007-08. The eluent used was a solution of dibutylamine (1% by volume) in tetrahydrofuran. For the calibration narrowly distributed, linear polystyrene standards with molecular weights between MP 1000000 and M P 162 g / mol were analyzed.
• the amine number was determined according to DIN 53176: 2002-1 1, using 2-propanol as the solvent for the titration.
• the sample (at least 0.5 g) is weighed to the nearest 0.1 mg in an 80 ml beaker and dissolved in 50 ml of 2-propanol.
• the sample is heated slightly until complete dissolution.
• the sample is placed on the magnetic stirrer and the electrode is completely immersed.
• the sample is titrated with 0.1 N isopropanolic hydrochloric acid.
• the acid number was determined according to DIN EN ISO 21 14: 2002-06, using 2-propanol as the solvent for the titration.
• the sample (at least 0.5 g) is weighed to the nearest 0.1 mg in an 80 ml beaker and dissolved in 50 ml of 2-propanol. If necessary, the sample is heated slightly until complete dissolution. The sample is placed on the magnetic stirrer, the electrode is completely immersed. The sample is titrated with 0.1 N ethanolic KOH.
• OH number reagent (14.4 g of p-toluenesulfonic acid are dissolved in 360 ml of ethyl acetate and mixed with about 60 ml of acetic anhydride).
• the reagent is added with a burette or a dispenser.
• the sample is heated for 15 minutes at 50 ° C. in a water bath or block thermostat. After cooling to room temperature, the sample decomposes the excess Acetic anhydride with about 30 ml of a pyridine-water mixture (3: 1) and stirred for about 5 min. Subsequently, the sample is titrated with 0.5 N ethanolic KOH.
• the hydroxyl number of the polyamide building blocks was determined by a method based on DIN ISO 4629.
• the sample (at least 0.5 g) is weighed accurately into an 80 ml weighing flask with a ground lid and dissolved in 20 ml of tetrahydrofuran After addition of 10.0 ml of OH number reagent A2 (12.5 g of 4-dimethylaminopyridine are dissolved in about 500 ml of tetrahydrofuran) and 5.0 ml of reagent B (about 25 ml
• Acetic anhydride are dissolved in about 500 ml of tetrahydrofuran), the sample is stirred for 30 min on the magnetic stirrer. About 2.0 ml of water are added and again for 10 min. touched. The sample is then titrated potentiometrically with 0.2 N ethanolic KOH.
• the isocyanate content was determined in accordance with DIN EN ISO 9369: 1997-08.
• the sample (at least 0.5 g) is weighed to the nearest 0.1 mg in an 80 ml beaker and dissolved in approx. 5 ml chlorobenzene (if necessary with heating). After addition of 9.5 ml of 0.2 N dibutylamine solution (in chlorobenzene), the sample is stirred and after
• 90.00 g of a monoadduct according to the patent EP 1 188779 are prepared from a lauryl alcohol and 2,4-tolylene diisocyanate.
• the reaction product is waxy and has an NCO content of 1 1, 1 wt .-%.
• a monoadduct according to the patent EP 1 188779 are prepared from a polyethylene glycol monomethyl ether having a hydroxyl number of 125 mg KOH / g and a mixture of 35% 2,6-tolylene diisocyanate and 65% 2,4-tolylene diisocyanate.
• Butylpolyethylenglycol having a hydroxyl number of 270 mg KOH / g and a mixture of 35% 2,6-tolylene diisocyanate and 65% 2,4-tolylene diisocyanate prepared.
• 125 g of a monoadduct according to the patent EP 1 188779 are prepared from a C13-C15 fatty alcohol ethoxylated with 5 mol of ethylene oxide having a hydroxyl value of 140 mg KOH / g and a mixture of 20% 2,6-tolylene diisocyanate and 80%.
• the adduct prepared contains 7.15% by weight of NCO.
• the adduct prepared contains 10.7 wt .-% NCO.
• the adduct prepared contains 8.10% by weight of NCO.
• a four-necked flask is provided with stirrer, dropping funnel, thermometer and reflux condenser.
• 71. 42 g (0.14 mol) of a polyethylene glycol monomethyl ether having a hydroxyl number of 13 mg KOH / g are weighed out and heated to 80 ° C. under a nitrogen atmosphere.
• 28.57 g (0.07 mol) Desmodur N3400 be added via a dropping funnel within 10 minutes and the mixture over a
• Polyamide AM1 In a four-necked flask equipped with stirrer, condenser, thermometer and water separator, 29.64 g of N-ethylpyrrolidone are weighed out and mixed with 0.07 mol of hexamethylenediamine (10.27 g of an 80% aqueous solution) and 0.035 mol of aminoethanol (2.14 g). added. The solution is heated to 100 ° C and the apparatus is rendered inert with nitrogen. 0.105 mol (61, 95 g) dimer fatty acid are added at 100 ° C to this solution. Under
• the hydroxyl number is 18.9 mg KOH / g.
• the hydroxyl number is 14.1 mg KOH / g.
• N-methylpyrrolidone In a four-necked flask equipped with stirrer, condenser, thermometer and water separator, 29.85 g of N-methylpyrrolidone are weighed out and mixed with 0.07 mol of hexamethylenediamine (10.27 g of an 80% aqueous solution) and 0.035 mol of 1-amino-2-propanol (2.63 g). The solution is heated to 100 ° C and the apparatus is rendered inert with nitrogen. 0.105 mol (61, 95 g) dimer fatty acid are added at 100 ° C to this solution. Under
• the hydroxyl number is 34.0 mg KOH / g.
• N-octylpyrrolidone 29.85 g of N-octylpyrrolidone are weighed into a four-necked flask equipped with stirrer, condenser, thermometer and water separator and admixed with 0.07 mol of hexamethylenediamine (10.27 g of an 80% aqueous solution) and 0.035 mol of 1-amino-2-propanol (2.63 g). The solution is heated to 100 ° C and the apparatus is rendered inert with nitrogen. 0.105 mol (61, 95 g) dimer fatty acid are added at 100 ° C to this solution. Under
• the hydroxyl number is 19.6 mg KOH / g.
• Polyamide AM8 30.23 g of N-octylpyrrolidone are weighed into a four-necked flask equipped with stirrer, condenser, thermometer and water separator and admixed with 0.07 mol of m-xylylenediamine (9.59 g) and 0.035 mol of aminoethanol (2.14 g). The solution is heated to 100 ° C and the apparatus is rendered inert with nitrogen. 0.105 mol (61, 95 g) dimer fatty acid are added at 100 ° C to this solution. Under water separation, the temperature is gradually increased up to 170 ° C and held at this temperature until no further reaction water over distilled. The reaction is monitored by determining the amine number of the product produced. The hydroxyl number is 17.1 mg KOH / g.
• the hydroxyl number is 18.9 mg KOH / g.
• N-ethylpyrrolidone 167.48 g are weighed into a four-necked flask equipped with stirrer, condenser, thermometer and water separator and admixed with 0.26 mol of hexamethylenediamine (37.75 g of an 80% strength aqueous solution).
• the solution is heated to 100 ° C and the apparatus is rendered inert with nitrogen. Following are 0.24 moles (141, 6 g) Dimer fatty acid added at 100 ° C to this solution. With water separation, the temperature is gradually increased up to 160 ° C and the reaction stopped when an amine value of 18.2 mg KOH / g.
• the acid value of the product produced is 18.2 mg KOH / g.
• Patent DE 10 2006 010 721 A1 The amine number of the product is 18.2 mg KOH / g, the acid number is 15.2 mg KOH / g.
• Isocyanuric acid AD1 added with a pipette. The temperature is raised to 60 ° C and held for 2.5 hours. The product obtained is amber and highly viscous.
• Isocyanuric acid AD1 is metered in with a pipette over a period of 5 minutes. The temperature is raised to 60 ° C and held for 2.5 hours. The product obtained is amber-colored and of high viscosity (the number average M n determined by gel permeation chromatography is 2230 g / mol).
• Example B7 In a four-necked flask equipped with stirrer, condenser and thermometer, 62.72 g of N-methylpyrrolidone, 26.21 g of the prepared polyamide solution AM 10 (corresponding to 18.35 g (0.01 mol) of polyamide) and 5.18 g (0 , 01 mol) of the synthesized Isocyanaturethans AD6 and inertized the apparatus with nitrogen. With stirring, the mixture is heated to 60 ° C and held this temperature range for 3 hours. The product obtained is amber-colored and highly viscous (the number average M n determined by gel permeation chromatography is 2301 g / mol).
• Isocyanuric acid AD1 added with a pipette. The temperature is raised to 60 ° C and held for 2.5 hours. Subsequently, the reaction mixture is treated with 0.5 wt .-% lithium chloride and over a period of one hour at 80 ° C.
• the product obtained is amber and liquid.
• Uretdionurethane AD7 is metered in with a pipette over a period of 5 minutes. The temperature is raised to 80 ° C and held for 3 hours. A yellow, viscous product is obtained (the number average M n determined by gel permeation chromatography is 3709 g / mol).
• Example B18 the number average M n determined by gel permeation chromatography is 3709 g / mol.
• Example B20 In a four-necked flask equipped with stirrer, condenser and thermometer, 65.72 g of N-ethylpyrrolidone and 23.43 g of the prepared polyamide solution AM1 1 (corresponding to 16.40 g (0.0065 mol) of polyamide) are heated to 40.degree Apparatus rendered inert with nitrogen. With stirring, 7.85 g (0.013 mol) of the synthesized isocyanuric acid AD2 are metered in with a pipette over a period of 5 minutes. The temperature is raised to 60 ° C and held for 2 hours. The product obtained is amber and viscous.
• Example B20 Example B20:
• Test System 1 Effect pigment orientation of an aluminum basecoat
• the effect pigment slurries are prepared by the formulation given in Table 4.
• the basecoat is prepared according to the formulation given in Table 5. 200 g of the basecoat are then each weighed into a 350 ml PE beaker and the respective rheology additive is incorporated with stirring with the Dispermat LV (from Getzmann) (5 min, 800 rpm, 5 cm paddle stirrer).
• the Rheology additives are used at a dosage of 1, 5% active substance to achieve a minimum viscosity of 600 mPas for the coating.
• the basecoats are then stored overnight at RT and then adjusted with the Brookfield viscometer LV DV-I (Brookfield, spindle 3 at 50 rev / min.) By addition of demineralized water to an injection viscosity of 600-800 mPas.
• the basecoat is applied by means of the application automat APL 2.71 automaton with a HVLP spray gun, 1 .3 mm nozzle (Oerter & Köhne GmbH & Co. KG) on DIN A4 aluminum sheets (type:
• Dispermat LV 5 cm paddle, 800 rpm.
• Spray application can not achieve or this viscosity can not be achieved by increasing the dosage according to data sheet.
• Comparative Examples VB4 and VB7 are so poor that a measurement of the flop value is not possible.
• the dosage of Comparative Example VB4 was carried out with the maximum dosage according to the technical data sheet.
• Comparative Examples VB1 and VB6 Comparative Examples VB1 and VB6.
• the examples according to the invention are thus better suitable for improving the effect pigment orientation of basecoats than the comparative examples.
• Test System 2 Storage stability of an effect pigment basecoat
• the effect pigment slurries and the basecoat are prepared according to the formulation given in Tables 7 and 8. After that, 100 g each of the
• Basecoat was weighed into a 350 ml PE beaker and incorporated the respective rheology additive with stirring with the Dispermat LV, Fa Getzmann (5 min., 800 rev / min., 5 cm paddle).
• the rheology additives are used with a dosage of 1, 5% active substance to a minimum viscosity of 600 mPas (spindle 3 at 50 rev / min., Brookfield viscometer LV DV-I, Brookfield) for the paint to achieve. If the minimum viscosity is not reached, the dosage of the respective additive according to the
• the basecoats are then stored overnight at RT and then adjusted with the Brookfield viscometer LV DV-I, Brookfield (spindle 3 at 50 rev / min.) By addition of demineralized water to an injection viscosity of 600-800 mPas.
• the basecoat is filled into 100 ml glass bottles and stored at RT for 4 weeks.
• the storage stability of the effect pigment basecoat is assessed by measuring the formation of syneresis in percent compared to the total volume. The lower the value for the syneresis, the better the storage stability of the coating and thus the rheological effectiveness of the respective rheology additive.
• Dispermat LV 10 min., 800 rpm, 5 cm paddle stirrer
• Component 10min Continue stirring, Dispermat LV, 5 cm paddle stirrer,
• Test system 3 Stability in a 2-component PU white paint
• the preparation of the white paint is carried out according to the table 10
• step wiper model 421/1 from Erichsen at a
• Compatibility of the rheology additive plays an important role in its suitability.
• the evaluation of the compatibility is carried out by measuring the gloss at 20 ° with a micro-trigloss from. BYK-Gardner at a wet film thickness of 90 ⁇ after drying overnight.
• Component A blank sample and AQ610 semi-finished product other examples according to Table 1 1 *
• Data sheet of the reference product (AQ610) requires due to the dosage form ine prior preparation as a semi-finished product before use in the paint.
• Component B Zero sample and AQ610 semi-finished product other examples according to Table 1 1 *
• Table 1 1 semi-finished product AQ-610
• Test System 4 Stability in an acrylate-styrene copolymer clearcoat
• the preparation of the clearcoat is carried out according to the formulation given in Table 13. Thereafter, 50 g of the clearcoat are each weighed into a 175 ml PE cup and the respective rheology additive with stirring with the Dispermat LV with a dosage of 0.5% active substance (based on total paint) incorporated (5 min., 1000 rpm, 2.5 cm toothed disc). Subsequently, the samples are allowed to stand for 1 day at RT and then performs the test of stability as a measure of the rheological effectiveness under application conditions.
• the sample with a step wiper (Model 421/1) from. Erichsen at a wet film thickness of 30-300 ⁇ and an automatic Aufziehbank BYK Gardner. At a speed of 5 cm / s on BYK Gardner contrast cards No. 2801. After application, the contrast cards are hung directly horizontally for drying. After drying, the layer thickness in ⁇ (wet) is determined at which the paint does not expire, that is, no runners or bead formation is recognizable. The higher the value for the stability when using the same active substance, the better the rheological effectiveness.
• VB10 and B21 are significantly different in that VB10 unlike B21 carries no COOH end group but is capped with tall oil fatty acid. VB10 has lower stamina compared to B21 and an unacceptable appearance due to speckling.
• Test System 5 Storage stability of an iron oxide yellow pigment concentrate
• the pigment concentrate is prepared according to the formulation given in Table 15. Thereafter, 50 g of the pigment concentrate in each case are poured into a 175 ml PE Weighed in the beaker and incorporated the respective rheology additive while stirring with the Dispermat LV with a dosage of 0.5% active substance (based on total) (5 min., 1000 rpm, 2.5 cm toothed disk). Only the semifinished product of VB3 had to be incorporated into the millbase due to the low content of active substance. The pigment concentrates are then filled into 50 ml snap-cap jars and stored at 40 ° C. for 6 weeks. The assessment of the storage stability of the
• Concentration of pigment takes place by measuring the synesis formation in percent compared to the total volume and by visual assessment of the sediment with the help of a metal spatula. The lower the value for the syneresis and the sediment, the better the storage stability of the pigment concentrate and thus the rheological effectiveness of the particular rheology additive.
• Test System 6 Anti-settling in an aqueous basecoat
• the effect pigment slurries and the basecoat are prepared according to the formulation given in Table 17 and 18. After that, 50 g each of the
• Basecoat weighed into a 100 ml glass bottle and stored for 4 days at RT.
• Dispermat LV 10 min., 800 rpm, 5 cm paddle stirrer
• the examples according to the invention are therefore more suitable for avoiding settling in the basecoat than the comparative examples.

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• 2018
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