EP2340095A2 - Additif antimousse pour le démoussage de peintures - Google Patents

Additif antimousse pour le démoussage de peintures

Info

Publication number
EP2340095A2
EP2340095A2 EP09782942A EP09782942A EP2340095A2 EP 2340095 A2 EP2340095 A2 EP 2340095A2 EP 09782942 A EP09782942 A EP 09782942A EP 09782942 A EP09782942 A EP 09782942A EP 2340095 A2 EP2340095 A2 EP 2340095A2
Authority
EP
European Patent Office
Prior art keywords
carbon atoms
formula
hydrocarbon radical
radical
defoaming
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP09782942A
Other languages
German (de)
English (en)
Inventor
Pedro Cavaleiro
Philippe Favresse
Berend-Jan De Gans
Michael Schwan
Stefanie Volkmer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Evonik Operations GmbH
Original Assignee
Evonik Goldschmidt GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Evonik Goldschmidt GmbH filed Critical Evonik Goldschmidt GmbH
Publication of EP2340095A2 publication Critical patent/EP2340095A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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.

Landscapes

  • 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)
  • Paints Or Removers (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (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.
EP09782942A 2008-10-22 2009-09-14 Additif antimousse pour le démoussage de peintures Withdrawn EP2340095A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102008043032A DE102008043032A1 (de) 2008-10-22 2008-10-22 Entschäumer zur Entschäumung von Lacken
PCT/EP2009/061838 WO2010046181A2 (fr) 2008-10-22 2009-09-14 Additif antimousse pour le démoussage de peintures

Publications (1)

Publication Number Publication Date
EP2340095A2 true EP2340095A2 (fr) 2011-07-06

Family

ID=42046383

Family Applications (1)

Application Number Title Priority Date Filing Date
EP09782942A Withdrawn EP2340095A2 (fr) 2008-10-22 2009-09-14 Additif antimousse pour le démoussage de peintures

Country Status (5)

Country Link
EP (1) EP2340095A2 (fr)
JP (1) JP5565878B2 (fr)
CN (1) CN102196844B (fr)
DE (1) DE102008043032A1 (fr)
WO (1) WO2010046181A2 (fr)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
PL3305840T3 (pl) 2016-10-05 2021-05-04 Evonik Operations Gmbh Kompatybilizator dla uniwersalnych barwników w rozpuszczalnikowych farbach alkidowych
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
DK3434737T3 (da) 2017-07-26 2023-03-27 Evonik Operations Gmbh Modificerede pigmenter og deres anvendelse
EP3438158B1 (fr) 2017-08-01 2020-11-25 Evonik Operations GmbH Production de polyéthersiloxanes par une liaison sioc
PL3505550T3 (pl) 2017-12-27 2022-09-12 Evonik Operations Gmbh Środek zwilżający i dyspergujący o właściwości reologicznej
EP3524651B1 (fr) 2018-02-08 2025-11-26 Evonik Operations GmbH Dispersion aqueuse de résine polyorganosiloxanhybride
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
CN122521156A (zh) 2018-12-20 2026-08-07 赢创运营有限公司 具有可重涂性能的通用滑爽和流平添加剂
EP3719076A1 (fr) 2019-04-01 2020-10-07 Evonik Operations GmbH Dispersion aqueuse de résine polyorganosiloxanhybride
PL3744752T3 (pl) 2019-05-28 2025-02-10 Evonik Operations Gmbh Sposób wytwarzania niecyklicznych polisiloksanów funkcjonalizowanych alkoksylem
PL3744756T3 (pl) 2019-05-28 2024-10-28 Evonik Operations Gmbh Układy acetoksylowe
EP3744764A1 (fr) 2019-05-28 2020-12-02 Evonik Operations GmbH Fabrication de polyéthersiloxanes par une liaison sioc
DK3744763T3 (da) 2019-05-28 2024-11-04 Evonik Operations Gmbh Skræddersyede sioc baserede polyethersiloxaner
ES2913783T3 (es) 2019-05-28 2022-06-06 Evonik Operations Gmbh Procedimiento para la purificación de acetoxisiloxanos
EP3744774B1 (fr) 2019-05-28 2021-09-01 Evonik Operations GmbH Procédé de recyclage des silicones
ES2939033T3 (es) 2019-10-28 2023-04-18 Evonik Operations Gmbh Mezcla de endurecimiento
EP3954743A1 (fr) 2020-08-12 2022-02-16 Evonik Operations GmbH Utilisation de dioxyde de silicium pour améliorer la conductivité des revêtements
EP3954740A1 (fr) 2020-08-14 2022-02-16 Evonik Operations GmbH Composition antimousse basée sur les polysiloxanes organo-fonctionnels modifiés
JP7875007B2 (ja) 2021-05-27 2026-06-17 エボニック オペレーションズ ゲーエムベーハー 有機官能基で変性されたポリブタジエンをベースとする消泡剤組成物
EP4095201A1 (fr) * 2021-05-28 2022-11-30 Axalta Coating Systems GmbH Composition d'électrodéposition cathodique à composés organiques volatils réduits

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4338217A (en) * 1979-01-31 1982-07-06 Wacker-Chemie Gmbh Antifoams
US4477371A (en) * 1982-09-23 1984-10-16 Wacker-Chemie Gmbh Aqueous dispersible defoamers

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2720512C2 (de) * 1977-05-06 1986-01-16 Wacker-Chemie GmbH, 8000 München Antischaummittel
US4261845A (en) * 1980-01-18 1981-04-14 Texaco Development Corporation Novel polyureas and their use as grease thickening agents
NL8105919A (nl) 1981-12-31 1983-07-18 Philips Nv Dynamische versterkerschakeling.
DE3245482A1 (de) 1982-12-08 1984-06-14 Byk-Mallinckrodt Chemische Produkte Gmbh, 4230 Wesel Entschaeumer und verfahren zu ihrer herstellung
DE19917186C1 (de) 1999-04-16 2000-09-21 Goldschmidt Ag Th Mittel zur Entschäumung wäßriger Medien und dessen Verwendung
JP2002226543A (ja) * 2001-01-30 2002-08-14 Dainippon Ink & Chem Inc ポリ尿素樹脂の製造方法
JP2005238147A (ja) * 2004-02-27 2005-09-08 Sanyo Chem Ind Ltd 界面活性剤
DE102005004024A1 (de) * 2005-01-28 2006-08-03 Goldschmidt Gmbh Polyether/Polyester enthaltende Dispergierharze

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4338217A (en) * 1979-01-31 1982-07-06 Wacker-Chemie Gmbh Antifoams
US4477371A (en) * 1982-09-23 1984-10-16 Wacker-Chemie Gmbh Aqueous dispersible defoamers

Also Published As

Publication number Publication date
JP5565878B2 (ja) 2014-08-06
DE102008043032A1 (de) 2010-04-29
CN102196844A (zh) 2011-09-21
WO2010046181A2 (fr) 2010-04-29
CN102196844B (zh) 2014-02-19
WO2010046181A3 (fr) 2010-07-01
JP2012506307A (ja) 2012-03-15

Similar Documents

Publication Publication Date Title
WO2010046181A2 (fr) Additif antimousse pour le démoussage de peintures
EP1685895B1 (fr) Résines de dispersion contenant un polyéther/polyester.
EP1757664A2 (fr) Pâte d'une poudre nano-échelle et d'un dispersant
JP2012506307A5 (fr)
EP1044712B1 (fr) Agent antimousse pour milieux aqueux
EP2970696B1 (fr) Additif renforçant la thixotropie et composition le contenant
WO2015197644A1 (fr) Systèmes bi- ou multicomposants à base de polyuréthane à tendance latente à l'épaississement
EP0893155A2 (fr) Sels de polyamines, leur utilisation comme agents dispersants pour des pigments ou des charges
EP2723779B1 (fr) Copolymères en peignes tensioactifs
WO2015197647A1 (fr) Systèmes résine époxyde/durcisseur époxyde ayant une tendance latente à l'épaississement
WO2015144404A1 (fr) Résines de dispersion
DE102006010721B4 (de) Biuretverbindungen zur Rheologiesteuerung
WO2015197646A1 (fr) Systèmes à base de résines de polyester insaturées à tendance latente à l'épaississement
WO2015079033A1 (fr) Composés d'addition de polyamines
EP0115585B1 (fr) Procédé de fabrication d'anti-mousses et anti-mousses ainsi produits
DE102006059558A1 (de) Neuartige Dispergierharze, deren Herstellung und deren Verwendung zur Dispergierung von Feststoffen
DE102007047211A1 (de) Entschäumerzusammensetzungen
KR20060050393A (ko) 분말상 (폴리)우레아의 제조 방법
EP2099543A2 (fr) Antimousse pour milieux aqueux
EP0147726B1 (fr) Anti-mousse pour des dispersions aqueuses et des solutions de résines synthétiques
DE3912879A1 (de) Feines pulver aus einem oberflaechenbehandelten polyorganosilsesquioxan
EP1777246A2 (fr) Polymères contenant des groupes amides pour réguler la rhéologie
DE102005055711A1 (de) Feststoffe/Polyether/Polyester enthaltende Dispergiermittel
DE2506203A1 (de) Entschaeumer
WO2015197648A1 (fr) Systèmes à base d'acrylate à tendance latente à l'épaississement

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20110321

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO SE SI SK SM TR

AX Request for extension of the european patent

Extension state: AL BA RS

DAX Request for extension of the european patent (deleted)
RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: EVONIK DEGUSSA GMBH

17Q First examination report despatched

Effective date: 20171020

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20180103