WO2010046181A2 - Additif antimousse pour le démoussage de peintures - Google Patents

Additif antimousse pour le démoussage de peintures Download PDF

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Publication number
WO2010046181A2
WO2010046181A2 PCT/EP2009/061838 EP2009061838W WO2010046181A2 WO 2010046181 A2 WO2010046181 A2 WO 2010046181A2 EP 2009061838 W EP2009061838 W EP 2009061838W WO 2010046181 A2 WO2010046181 A2 WO 2010046181A2
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WIPO (PCT)
Prior art keywords
carbon atoms
formula
hydrocarbon radical
radical
defoaming
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PCT/EP2009/061838
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German (de)
English (en)
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WO2010046181A3 (fr
Inventor
Pedro Cavaleiro
Philippe Favresse
Berend-Jan De Gans
Michael Schwan
Stefanie Volkmer
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Evonik Goldschmidt Gmbh
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Application filed by Evonik Goldschmidt Gmbh filed Critical Evonik Goldschmidt Gmbh
Priority to JP2011532556A priority Critical patent/JP5565878B2/ja
Priority to EP09782942A priority patent/EP2340095A2/fr
Priority to CN200980142166.4A priority patent/CN102196844B/zh
Publication of WO2010046181A2 publication Critical patent/WO2010046181A2/fr
Publication of WO2010046181A3 publication Critical patent/WO2010046181A3/fr

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D19/00—Degasification of liquids
    • B01D19/02—Foam dispersion or prevention
    • B01D19/04—Foam dispersion or prevention by addition of chemical substances
    • B01D19/0404—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance
    • B01D19/0413—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance compounds containing N-atoms
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D19/00—Degasification of liquids
    • B01D19/02—Foam dispersion or prevention
    • B01D19/04—Foam dispersion or prevention by addition of chemical substances
    • B01D19/0404—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
    • C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
    • C07C275/14—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/47—Levelling agents
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/16—Amides; Imides
    • C10M133/18—Amides; Imides of carbonic or haloformic acids
    • C10M133/20—Ureas; Semicarbazides; Allophanates
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
    • C10M171/004—Foam inhibited lubricant compositions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M173/00—Lubricating compositions containing more than 10% water
    • C10M173/02—Lubricating compositions containing more than 10% water not containing mineral or fatty oils
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/21—Urea; Derivatives thereof, e.g. biuret
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/102—Polyesters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/106—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing four carbon atoms only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/10—Amides of carbonic or haloformic acids
    • C10M2215/102—Ureas; Semicarbazides; Allophanates
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/18—Anti-foaming property
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/015—Dispersions of solid lubricants

Definitions

  • the invention relates to defoamers for defoaming paints, preferably those paints that are used as dip paints.
  • the antifoams according to the invention contain solids based on urea derivatives.
  • defoamers which are able to prevent or destroy unwanted foams even at very low use concentrations from about 0.001% by weight, to the medium to be defoamed.
  • defoamers are, for example, silicone oils, mineral oils, hydrophobic polyoxyalkylenes, long-chain alcohols and mixtures of these products with one another and emulsions thereof.
  • hydrophobic solids are to enhance the effectiveness often also added in amounts of 0.1 to 15 wt .-%, which specifically promote the inputs of drin ein EntFiumerwirk fürs to Schaumlamel ⁇ len and thus support the foam collapse very effective.
  • Suitable hydrophobic solids are corresponding silicic acids, metal stearates, polyolefins and waxes of suitable particle sizes.
  • urea and urea derivatives as an additive to defoamer formulations is also known per se.
  • EP-A-0 115 585 (DE 32 45 582) describes ureas which are prepared in situ in an organic carrier medium at relatively low temperatures and have defoaming properties for aqueous media. These is obtained by combining preferably equivalent amounts of isocyanates and amines in the corresponding organic carrier medium at temperatures below the melting point of the reaction product.
  • a disadvantage of the known methods and the defoamers obtained with you is the poor filterability of he ⁇ held defoamers, so that it is in the filtration of z. B., dipping paints, which contain the defoamer, comes to a relatively fast blocking of the filter.
  • Another disadvantage of the known method or the defoamers obtained with you is the complete or partial settling of the solid during storage. Inhomogeneous solid state distributions require an undesirable and time-consuming homogenization before use as a defoamer.
  • defoamers having urea derivatives have improved filterability when produced in the presence of a branched monohydric alcohol.
  • the invention thus relates to agents for defoaming aqueous media which, as defoamers, contain at least one urea derivative of the formula I.
  • R 1 is a hydrocarbon radical having 2 to 30 carbon atoms or a hydrocarbon radical having 3 to 24 carbon atoms and a nitrogen atom or a hydrocarbon radical having 2 to 30 carbon atoms and a carbonyl group
  • R 2 is a hydrogen atom or a hydrocarbon radical having 1 to 24 carbon atoms
  • R 3 is a hydrogen atom or a hydrocarbon radical having 1 to 24 carbon atoms
  • R 4 - are an organic radical having 2 to 30 carbon atoms and n - 0 to 5, in the form of solid particles, wherein the urea derivative is obtained by reacting at least one isocyanate with at least one amine in a carrier medium, characterized in that the reaction in the presence of a einwerti ⁇ gen alcohol of the formula VI
  • the agent according to the invention has the advantage that the solid particles have a better filterability and thus, when the agents are used as defoamers in dip paints, their filtration does not cause the filters to become blocked or clogged.
  • the compositions of the invention also have the advantage that they Herge ⁇ represents may have according to the prior art, a relatively low viscosity, in particular ⁇ sondere a lower viscosity compared to the means and therefore the filterability and pumpability of media in which the defoamer are used, is improved.
  • the agent of the invention and a method for its Her ⁇ position and its use are hereinafter of example described without the invention being limited to these exemplary embodiments . If ranges, general formulas or classes of compounds are stated below, these should not only include the corresponding regions or groups of compounds which are explicitly mentioned, but also all subregions and subgroups of compounds which are obtained by removing individual values (ranges) or Compounds can be obtained. Where documents are cited in the present description, their home is to halt fully into the disclosure content of the present OF INVENTION ⁇ dung. Be in the context of the present invention, compounds such.
  • polyethers which may have several units repeatedly, they may statistically distributed (statistical oligomer or polymer) or arranged (block oligomer or block polymer) occur in these compounds. Information on the number of units in such compounds is to be understood as an average, averaged over all corresponding compounds.
  • compositions according to the invention for defoaming aqueous media which contain at least one urea derivative of the formula I as defoamer
  • R 1 is a hydrocarbon radical having 2 to 30 carbon atoms or a hydrocarbon radical having 3 to 24 carbon atoms and a nitrogen atom or a hydrocarbon radical having 2 to 30 carbon atoms and a carbonyl group,
  • R 1 is a hydrogen atom or a hydrocarbon radical having 1 to 24 carbon atoms
  • R 3 is a hydrogen atom or a hydrocarbon radical having 1 to 24 carbon atoms
  • the proportion of the amine in the reaction mixture during the reaction is preferably from 500 to 20% by mass, preferably from 200 to 50% by mass, based on the mass of the alcohol of the formula VI.
  • the solid particles obtained in the reaction at least once dispersed in the presence of at least ei ⁇ nes dispersant.
  • the reaction mixture obtained in the reaction is preferably admixed with a dispersing aid and treated in an apparatus which is suitable for dispersion.
  • suitable Apparatu ren can z.
  • ceramic ball mills or a Superdissolver be used.
  • dispersants it is possible to use all known dispersants which are suitable for use in apolar media.
  • a dispersant polyether and / or Po ⁇ lyester used or sorbitan esters.
  • polyether and / or polyester which have styrene oxide units.
  • polyethers or polyesters are described, for example, in US 2006-0183815.
  • Particularly preferred polyether esters which have styrene units are, for. B. those caused by the partial or full implementation of
  • T is a hydrogen radical and / or an optionally substituted, linear or branched aryl, arylalkyl, alkyl or alkenyl radical having 1 to 24 carbon atoms,
  • A is at least one divalent radical selected from the group of the linear, branched, cyclic and aromatic hydrocarbons,
  • Z is at least one radical selected from the group of sulfonic acids, sulfuric acids, phosphonic acids, phosphoric acids, carboxylic acids, isocyanates, epoxides, especially phosphoric acid and (meth) acrylic acid
  • B is a radical of general formula (IX)
  • the reaction products may be in the form of the amides and / or the corresponding salts. If the molecule part "Z" has a multiple bond, as may be the case, for example, in the case of the polyethers and the alcohol-initiated polyesters in which the terminal OH group has been esterified with an unsaturated acid, such as (meth) acrylic acid, the bond takes place via a Michael addition of the NH function to the double bond.
  • an unsaturated acid such as (meth) acrylic acid
  • amino-functional polymers are amino-functional polyamino acids such as polylysine from Aldrich Chemical Co .; amino-functional silicones which are sold under the trade name Tegomer® ASi 2122 by Degussa AG; Polyamidoamines sold under the tradename Polypox®, Aradur® or "Starburst®” Dendrimers by Aldrich Chemical Co .; Polyallylamines and poly (N-alkyl) allylamines which are available under the trade names PAA from Nitto Boseki; Polyvinylamines, which are sold under the trade name Lupamin® by BASF AG; Polyalkyleneimines, such as, for example, polyethyleneimines, which are sold under the trade names Epomin® (Nippon Shokubai Co., Ltd.), Lupasol® (BASF AG); Polypropyleneimines which are available under the trade name Astramol® from DSM AG.
  • amino-functional polyamino acids such as polylysine from Aldrich Chemical Co
  • amino-functional polymers are the above-mentioned systems by crosslinking with amine-reactive groups. This crosslinking reaction takes place, for example, via polyfunctional isocyanates, carboxylic acids, (meth) acrylates and epoxides. Further examples are poly (meth) acrylate polymers which are dimethy laminopropyl (meth) acrylamide (Degussa AG) or dimethylaminoethyl (meth) acrylate (Degussa AG) as monomers.
  • amino-functional polymers having a molecular weight of 400 g / mol to 600,000 g / mol are used.
  • radical T examples include alkyl radicals having 1 to 24 carbon atoms, such as the methyl, ethyl, propyl, iso-propyl, butyl, isobutyl, tert-butyl, hexyl, iso-hexyl , Octyl, nonyl, iso-nonyl, decyl, dodecyl, hexadecyl and octadecyl.
  • optionally substituted aryl or arylalkyl radicals having up to 24 carbon atoms are the phenyl, benzyl, toluyl or phenethyl radical.
  • a particularly preferred embodiment of the dispersants is obtainable by the polyester group by known per se methods by ring-opening polymerization with a starter molecule such as T-CH 2 -OH or T-COOH and one or more lactones, such as ⁇ -propiolactone, ß- Butyrolactone, ⁇ -butyrolactone, 3,6-dimethyl-1,4-dioxane-2,5-dione, ⁇ -valerolactone, ⁇ -valerolactone, ⁇ -caprolactone, ⁇ -caprolactone, 4-methylcaprolactone, 2-methylcaprolactone,
  • 5-hydroxydodecanoic acid lactone 12-hydroxydodecanoic acid lactone, 12-hydroxy-9-octadecenoic acid, 12-hydroxyoctadecanoic acid.
  • Starter molecules such as T-COOH - as well as the fatty alcohols T-CH 2 -OH - which can be prepared therefrom, are preferably monobasic fatty acids based on natural vegetable or animal fats and oils with 6 to 24 known and customary in this field Carbon atoms, in particular with 12 to 18 carbon atoms, such as caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, isostearic acid, stearic acid, oleic acid, linoleic acid, petroselic acid, elaidic acid, arachidic acid, behenic acid, erucic acid, Ga dolein Textre, rapeseed oil fatty acid, soybean oil fatty acid, sunflower oil ⁇ fatty acid, tall oil fatty acid which can be used alone or in admixture in the form of their glycerides, methyl or ethyl esters or as free acids, as well as the processing obtained
  • the iodine value is the amount of iodine absorbed by 100 g of the compound to saturate the double bonds.
  • Both the fatty acids and the resulting alcohols can be modified by addition of alkylene oxides, in particular ethylene oxide and / or styrene oxide.
  • Examples of the polyether building blocks of B are alkylene oxides such as: ethylene oxide, propylene oxide, butylene oxide, styrene oxide, Dode- cenoxid, tetradecenoxide, 2, 3-Dimethyloxiran, cyclopentene, 1, 2-epoxypentane, 2-Isopropyloxiran, glycidyl methyl ester, glycidylisopropyl ester, Ep i ch lorh ydr in, 3-methoxy-2, 2-dimethyloxirane, 8-oxabicyclo [5.1.0] octane, 2-pentyloxirane, 2-methyl-3-phenyloxirane, 2, 3-epoxypropylbenzene, 2- (4-fluorophenyl ) oxirane, tetrahydrofuran, and their pure pairs of enantiomers or mixtures of enantiomers.
  • the group Z may be composed of addition products of the carboxylic
  • the weight ratio of regular polyester to polyether in the preferred dispersing agent is preferably between 50: 1 and 1: 9, preferably between 40: 1 and 1: 5 and be ⁇ Sonders preferably between 30: 1 and 1: 1.
  • dispersants preferably used can, for. See, for example, US-2006-0183815, which is fully ⁇ circumferentially referenced and whose disclosure should include the disclosure of the present invention.
  • the inventive composition comprises as urea derivatives before ⁇ preferably those in which R 1 is a hydrocarbon ⁇ radical having 2 to 30 carbon atoms, preferably from 2 to 20 and particularly preferably having 12 to 18 carbon atoms, an organic radical of the formula II,
  • R 5 is a hydrocarbon radical having 1 to 8 carbon atoms, preferably 1 to 6 carbon atoms, or an organic radical of the formula III,
  • R 6 is an organic radical having 2 to 30 carbon atoms, preferably having 2 to 20 carbon atoms
  • the radical R 2 is a hydrogen atom
  • the radical R 3 is a hydrogen atom
  • the radical R 4 is a hydrocarbon radical having 1 to 30, preferably 1 to 12 and particularly preferably 2 to 6 carbon atoms.
  • An equally preferred means comprises as urea derivatives before ⁇ preferably those based on, in which R 1 is a hydrocarbon radical having from 2 to 30, preferably 2 to 20 carbon atoms, R 2 and R 3 is a hydrogen atom and R 4 is the organic residue
  • R 7 is a hydrocarbon radical having 1 to 30, preferably ⁇ , from 1 to 12 carbon atoms.
  • compositions of the invention all mono- or polyisocyanates and all mono- or polyamine compounds can be converted ⁇ sets.
  • monoisocyanates z For example, all isocyanates obtainable by phosgenation reaction from known monoamines can be used. In particular 2-Ethylhexylisocyanat, Isotridecylisocyanat, palmityl, stearyl or C 8 -C 24 are used as -Alkylisocyanat monoisocyanates.
  • t lisocyanat isocyanates as lauryl, octadecyl, 1, 6-hexamethylene diisocyanate, stearyl and / or Palmity- or a mixture thereof are used.
  • Mono- or polyfunctional amines can be used as amines.
  • Preferred amines include octylamine, diethyltriamine, oleylamine, stearylamine, distearylamine, reaction products of stearylamine with hexamethylenediamine and toluene diisocyanate, ethylenediamine, propanediamine, butanediamine, hexanediamine, 1,12-dodecanediamine, 4,4'-diaminodiphenylmethane , 3,3'-dimethyl-4,4'-diaminodiphenylmethane, p-xylylenediamine, isophoronediamine or hydrazine and mixtures of two or more of these amines.
  • the isocyanate used is preferably stearyl isocyanate and the amine is propanediamine.
  • At least one organic and / or at least one mineral oil can be used as the carrier medium.
  • Such oils can z.
  • B. native oils such as. As soybean or sunflower oil or paraffin-based spindle oils or naphthene-based or aromatic mineral oils.
  • a siloxane and / or at least one organomodified siloxane is used as a carrier medium to ⁇ minimum.
  • As a carrier medium are also suitable for.
  • B. isobutyl or Isooctylstearat polyalkylene glycols and combinations of these products with said oils or siloxanes.
  • composition according to the invention preferably has a mass ratio of urea derivatives to carrier media of from 0.002 to 1 to 1 to 1, preferably from 0.01 to 1 to 0.20 to 1.
  • the defoaming agents according to the invention can also be converted into aqueous emulsions.
  • emulsifiers z For example, those having an HLB value of 4 to 18 (HLB value according to WC Griffin “Classification of surface active agents by HLB" J. Soc. Cosmetic Chemists 1, 311 (1950)) are preferred.
  • Nonionic emulsifiers are preferably used used.
  • E preferably used are mulgatoren z.
  • the proportion of E- mulgatoren the inventive agent for defoaming is preferably from 1 to 10 mass% based on the carrier Medi ⁇ order.
  • the agent according to the invention for defoaming aqueous media consists of a. Defoamers, of which at least one is preferably all a urea derivative of the formula I as defined above in the form of solid particles, b. one or more carrier media as indicated above, c. one or more monohydric alcohols of formula VI as indicated above, d. optionally one or more dispersants, e. optionally one or more emulsifiers and f. if necessary water.
  • the agent according to the invention for defoaming aqueous media consists of a. Defoamers, at least one of which is preferably all of a urea derivative of the formula I as defined above defi ned ⁇ in the form of solid particles, b. one or more carrier media as indicated above, c. one or more monohydric alcohols of the formula VI as indicated above, and d. one or more dispersants,
  • the mass fraction of component a is preferably from 5 to 40, component b from 25 to 75 and component c from 1 to 10. Particularly preferably, the proportion by weight of component a is from 10 to 30, and component b from 40 to 60 and component c of 2 to 5. If one or more dispersing additives are present in the composition according to the invention, they are preferably present in a proportion by mass of from 0.75 to 1 to 1.25 to 1, preferably about 1 to 1, based on a.
  • compositions according to the invention can be obtained by all known processes for the preparation of urea derivatives, with the proviso that the reaction of the isocyanate compound with the amine compound is carried out in the presence of a monohydric alcohol of the formula VI.
  • the reaction is carried out in accordance with the method described in DE 32 45 482.
  • the defoaming agent according to the invention is prepared by the process according to the invention described below.
  • the reaction is preferably carried out so that first the Trä ⁇ germedium is mixed with the alcohol of the formula VI and this mixture first amine and then with the nat with the isocyanate, preferably is added under constant stirring.
  • Mono- or polyfunctional isocyanates can be used as isocyanates.
  • monoisocyanates z. B. all obtainable by phosgenation reaction of known monoamines available isocyanates, in particular 2-ethylhexyl isocyanate, isotridecyl isocyanate, palmityl-stearyl isocyanate or Ci 8 -C 24 alkyl isocyanate.
  • Preferred isocyanates are stearyl isocyanate and / or palmityl isocyanate or a mixture thereof.
  • Mono- or polyfunctional amines can be used as amines.
  • Preferred amines include oleylamine, stearylamine, distearylamine, reaction products of stearylamine with hexamethylenediamine and tolylene diisocyanate, ethylenediamine, propanediamine, butanediamine, hexanediamine, 1,12-dodecanediamine, 4,4'-diaminodiphenylmethane, 3, 3 '-Dimethyl-4,4'-diaminodiphenylmethane, p-xylylenediamine, isophoronediamine or hydrazine and mixtures of two or more of these amines.
  • isocyanate and amine that the equivalence ratio of isocyanate functions to Aminfunkti- ons of 0.5 to 1 to 1 to 0.2, preferably from 1 to 1.2 to 1 to 0.8. Particular preference is given to using propane amine as amine and stearyl isocyanate as isocyanate.
  • propane amine as amine
  • stearyl isocyanate as isocyanate.
  • the reaction is carried out preferably at a temperature of 20 to 60 0 C using a stirrer which mixes the reaction onsgemisch with a 50 to 1000 revolutions per minute.
  • the reaction mixture obtained can be used directly as an agent for Ent ⁇ foaming aqueous media.
  • the resulting reaction mixture is dispersed prior to use as an agent for defoaming aqueous media after addition of one of the abovementioned dispersants.
  • a dispersant preferably added before ⁇ the reaction mixture obtained in the reaction with a dispersant and treated in an apparatus which is suitable for dispersion.
  • suitable apparatus can z.
  • ceramic ball mills or a Superdissolver be used.
  • reaction mixture or dispersed reaction mixture may be advantageous to filter the directly obtained reaction mixture or dispersed reaction mixture prior to use. This can preferably be done via a 25 micron filter.
  • the agents of the invention, or compositions obtained by the method according to the invention ⁇ SSE (defoamer) z can. B. for defoaming of coolants, polymer dispersions, paints and / or printing inks. Therefore, the present invention also provides aqueous media, corresponds holding an inventive agent for defoaming, and in particular ⁇ sondere cooling lubricants, polymer dispersions, paints, preferably ⁇ example paints, or printing inks.
  • T2 mixture of 80% by weight of Ecolane 100 (Total Germany GmbH) and 20% by weight of Polyöl 110 (Evonik Goldschmidt GmbH)
  • T3 mixture of 10% by weight of Indopol H 2100 (Innovene) and 90
  • T4 Nynas T22 (Nynas Petroleum (Stockholm, Sweden)
  • T5 TEGO STB 8932 (BP 18100) (Evonik Goldschmidt GmbH)
  • T6 50 wt. % Lithene PM (Sartomer) and 50% by weight Polyol 110 (Evonik Goldschmidt GmbH)
  • ROH 1 2-ethyl-ethanol
  • DA3 TEGO SMOV (all Evonik Goldschmidt GmbH)
  • the defoamers of Examples 1 to 17 were stored for one week at room temperature and then the settling behavior was visually assessed on the basis of an optionally present phase separation.
  • test specimens were prepared and evaluated according to the following recipes:
  • inventive examples are (Example 2, 4, 7, 8, 11, 12) with respect to their defoaming effect the examples not Inventive ⁇ invention (Example 13 to 15, and 17) clearly superior.
  • test was carried out in the styrene-acrylate dispersion Aronic® 290 D from BASF and the pure acrylate dispersion Acronal® A603 from BASF.
  • the defoamers according to the invention and not according to the invention were incorporated in the dispersions for one minute at 1000 rpm.
  • air was dispersed in for 1 minute at 2500 rpm by means of a turbine stirrer (diameter 4 cm).
  • the dispersion thus processed was then, immediately after stopping the stirrer, filled into a scale to the mark of 50 ml and weighed.
  • the weight is influenced by the amount of air entrained and is a measure of the effectiveness of the defoamer.
  • the results of Example 21 are summarized in Tables 4 and 5.
  • test specimen is prepared and evaluated according to the following recipes:
  • the polymer dispersions additized with defoamer were dispersed in air at 3000 rpm for 3 minutes by means of a turbine stirrer (diameter 4 cm).
  • the thus processed dispersion was then, immediately after stopping the stirrer, filled in a scale of 45g in a 100 ml graduated cylinder and read the volume.
  • the volume is influenced by the amount of air entrained and is a measure of the effectiveness of the defoamer.
  • the results of Application Example 22 are shown in Table 8.
  • the topcoats, the defoamers according to the invention according to Example 10 or 11 have, with respect to their deaeration, clearly superior to the topcoats comprising defoamers according to the invention according to Examples 15 and 16.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Dispersion Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Degasification And Air Bubble Elimination (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Paints Or Removers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Agent de démoussage de milieux aqueux qui contient, en tant qu'agent antimousse, des dérivés d'urée de formule (I) dans laquelle R1 représente un groupe hydrocarbure ayant 4 à 30 atomes de carbone ou un groupe hydrocarbure ayant 4 à 24 atomes de carbone et un atome d'azote ou un groupe hydrocarbure ayant 4 à 30 atomes de carbone et un radical carbonyle, R2 représente un atome d'oxygène ou un groupe hydrocarbure ayant 1 à 24 atomes de carbone, R3 représente un atome d'oxygène ou un groupe hydrocarbure ayant 1 à 24 atomes de carbone, R4 représente un groupe organique ayant 2 à 30 atomes de carbone et n vaut 0 à 5, sous forme de particules solides, lesdits dérivés d'urée étant obtenus par mise en réaction d'isocyanates avec des amines dans un milieu de support. Selon l'invention, la mise en réaction est effectuée en présence d'un alcool monovalent de formule R8-OH dans laquelle R8 représente un radical alkyle linéaire ou ramifié, de préférence ramifié, ayant 6 à 10 atomes de carbone.
PCT/EP2009/061838 2008-10-22 2009-09-14 Additif antimousse pour le démoussage de peintures WO2010046181A2 (fr)

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JP2011532556A JP5565878B2 (ja) 2008-10-22 2009-09-14 ラッカーを消泡するための消泡剤
EP09782942A EP2340095A2 (fr) 2008-10-22 2009-09-14 Additif antimousse pour le démoussage de peintures
CN200980142166.4A CN102196844B (zh) 2008-10-22 2009-09-14 用于使漆消泡的消泡剂

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DE102008043032A DE102008043032A1 (de) 2008-10-22 2008-10-22 Entschäumer zur Entschäumung von Lacken

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CN106492513A (zh) * 2016-11-14 2017-03-15 武汉宜田科技发展有限公司 一种湿法磷酸尾矿槽用消泡剂
US10414872B2 (en) 2017-08-01 2019-09-17 Evonik Degussa Gmbh Production of SiOC-bonded polyether siloxanes
US10577512B2 (en) 2016-10-05 2020-03-03 Evonik Operations Gmbh Compatibilizer for universal colorant in solventborne alkyd paints
US10752801B2 (en) 2017-12-27 2020-08-25 Evonik Operations Gmbh Wetting agents and dispersants having rheological character
US11021608B2 (en) 2018-02-08 2021-06-01 Evonik Operations Gmbh Aqueous polyorganosiloxane hybrid resin dispersion
US11236204B2 (en) 2019-05-28 2022-02-01 Evonik Operations Gmbh Production of SiOC-bonded polyether siloxanes
US11254819B2 (en) 2019-10-28 2022-02-22 Evonik Operations Gmbh Curing agent mixture
US11261298B2 (en) 2019-05-28 2022-03-01 Evonik Operations Gmbh Tailored SiOC-based polyethersiloxanes
US11286366B2 (en) 2019-05-28 2022-03-29 Evonik Operations Gmbh Process for recycling silicones
US11377523B2 (en) 2019-05-28 2022-07-05 Evonik Operations Gmbh Process for producing non-cyclic alkoxy-functional polysiloxanes
US11420985B2 (en) 2019-05-28 2022-08-23 Evonik Operations Gmbh Acetoxy systems
US11472822B2 (en) 2019-05-28 2022-10-18 Evonik Operations Gmbh Process for purifying acetoxysiloxanes
US12018149B2 (en) 2019-04-01 2024-06-25 Evonik Operations Gmbh Aqueous polyorganosiloxane hybrid resin dispersion
US12053721B2 (en) 2020-08-14 2024-08-06 Evonik Operations Gmbh Defoamer composition based on organofunctionally modified polysiloxanes
US12091579B2 (en) 2018-12-20 2024-09-17 Evonik Operations Gmbh Universal slip and flow control additives with recoatable quality

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DE102010003134A1 (de) 2010-03-23 2011-09-29 Evonik Goldschmidt Gmbh Vorhangstabilisatoren für die Papierherstellung und -verarbeitung
CN102961897B (zh) * 2012-10-21 2014-07-16 安徽銮威化工科技开发有限公司 一种静电植绒胶消泡剂及其应用
CN104906832B (zh) * 2015-05-22 2016-08-31 陕西省石油化工研究设计院 一种聚醚酯/矿物油复合型消泡剂及其制备方法
CN110575786B (zh) * 2018-06-11 2021-09-14 江苏四新科技应用研究所股份有限公司 一种新型疏水组合物

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10577512B2 (en) 2016-10-05 2020-03-03 Evonik Operations Gmbh Compatibilizer for universal colorant in solventborne alkyd paints
CN106492513A (zh) * 2016-11-14 2017-03-15 武汉宜田科技发展有限公司 一种湿法磷酸尾矿槽用消泡剂
CN106492513B (zh) * 2016-11-14 2018-11-27 武汉宜田科技发展有限公司 一种湿法磷酸尾矿槽用消泡剂
US10414872B2 (en) 2017-08-01 2019-09-17 Evonik Degussa Gmbh Production of SiOC-bonded polyether siloxanes
US10752801B2 (en) 2017-12-27 2020-08-25 Evonik Operations Gmbh Wetting agents and dispersants having rheological character
US11021608B2 (en) 2018-02-08 2021-06-01 Evonik Operations Gmbh Aqueous polyorganosiloxane hybrid resin dispersion
US12091579B2 (en) 2018-12-20 2024-09-17 Evonik Operations Gmbh Universal slip and flow control additives with recoatable quality
US12018149B2 (en) 2019-04-01 2024-06-25 Evonik Operations Gmbh Aqueous polyorganosiloxane hybrid resin dispersion
US11261298B2 (en) 2019-05-28 2022-03-01 Evonik Operations Gmbh Tailored SiOC-based polyethersiloxanes
US11286366B2 (en) 2019-05-28 2022-03-29 Evonik Operations Gmbh Process for recycling silicones
US11377523B2 (en) 2019-05-28 2022-07-05 Evonik Operations Gmbh Process for producing non-cyclic alkoxy-functional polysiloxanes
US11420985B2 (en) 2019-05-28 2022-08-23 Evonik Operations Gmbh Acetoxy systems
US11472822B2 (en) 2019-05-28 2022-10-18 Evonik Operations Gmbh Process for purifying acetoxysiloxanes
US11236204B2 (en) 2019-05-28 2022-02-01 Evonik Operations Gmbh Production of SiOC-bonded polyether siloxanes
US11254819B2 (en) 2019-10-28 2022-02-22 Evonik Operations Gmbh Curing agent mixture
US12053721B2 (en) 2020-08-14 2024-08-06 Evonik Operations Gmbh Defoamer composition based on organofunctionally modified polysiloxanes

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EP2340095A2 (fr) 2011-07-06
CN102196844B (zh) 2014-02-19
CN102196844A (zh) 2011-09-21
DE102008043032A1 (de) 2010-04-29
JP5565878B2 (ja) 2014-08-06
WO2010046181A3 (fr) 2010-07-01
JP2012506307A (ja) 2012-03-15

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