CN102196844B - Defoaming agent for defoaming lacquers - Google Patents

Defoaming agent for defoaming lacquers Download PDF

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Publication number
CN102196844B
CN102196844B CN200980142166.4A CN200980142166A CN102196844B CN 102196844 B CN102196844 B CN 102196844B CN 200980142166 A CN200980142166 A CN 200980142166A CN 102196844 B CN102196844 B CN 102196844B
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carbon atom
alkyl
composition
formula
defoamer
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CN102196844A (en
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P·卡瓦莱罗
P·法夫雷斯
B-J·德甘斯
M·施万
S·沃尔克默
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Evonik Operations GmbH
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Evonik Goldschmidt GmbH
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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
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    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Dispersion Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

The present invention relates to substances for defoaming aqueous media. Said substances contain urea derivatives of formula (I) in the form of solid particles as defoaming agents. In formula (I), R1 is a hydrocarbon group comprising 4 to 30 carbon atoms, a hydrocarbon group comprising 4 to 24 carbon atoms and a nitrogen atom, or a hydrocarbon group comprising 4 to 30 carbon atoms and a carbonyl group, R2 is a hydrogen atom or a hydrocarbon group comprising 1 to 24 carbon atoms, R3 is a hydrogen atom or a hydrocarbon group comprising 1 to 24 carbon atoms, R4 is an organic group comprising 2 to 30 carbon atoms, and n is a number between 0 and 5. The urea derivatives are obtained by reacting isocyanates with amines in a carrier medium. The invention is characterized in that the reaction is carried out in the presence of a monovalent alcohol of formula (VI) R8-OH, in which R8 is a linear or branched, preferably branched, alkyl group comprising 6 to 10 carbon atoms.

Description

For making to paint the defoamer of froth breaking
Technical field
The present invention relates to make the defoamer of coating froth breaking, preferably make the defoamer as the coating froth breaking of deposition coating (deposition coating materials) type.Defoamer of the present invention comprises the solid based on urea derivative.
Background technology
In numerous commercial runs, particularly, when operating, must suppress or prevent completely to form the foam of not expecting during preparation or process operation in aqueous medium.This can, by the medium for the treatment of froth breaking is mixed and realized with the material that is known as anti-foaming agent or defoamer, even can prevent or destroy the foam of not expecting when using defoamer with low-down concentration more than approximately 0.001 % by weight.The example of the defoamer of the prior art comprises mixture each other of silicone oil, mineral oil, hydrophobicity polyoxyalkylene, long-chain alcohol and these materials and their emulsion.In order to strengthen its activity, conventionally add the so-called hydrophobic solid of 0.1 % by weight to 15 % by weight amount, it promotes the infiltration rate of active antifoam composition to foam lamella especially, and therefore very effectively makes foam collapse.Suitable hydrophobic solid is the wax of corresponding silica, Metallic stearates, Polyolefin and appropriate particle size.
By urea and urea derivative, as the auxiliary agent of defoamer preparation itself, be also known.
EP-A-0 115 585 (DE 32 45 582) has described at relatively low temperature, the urea of preparing at organic carrier medium situ, and it has the froth breaking character for aqueous medium.They are by corresponding organic carrier medium, at the temperature lower than product fusing point, the isocyanates of preferred equivalent and amine are obtained by mixing.
The urea derivative of having prepared thus following formula
Figure BPA00001349763200011
R=C 4-C 30alkyl
R '=chemical single bond, C 2-C 12on alkylidene, aryl, there is extra C 1-C 9the list of alkyl
Ring or bicyclic aryl, ring alkylidene
R "=H, C 1-C 24alkyl
R″″＝H、-CH 3-
x＝0-5。
Its shortcoming is, according to the described step of EP-A-0 115 585, because original position forms urea derivative, must use can not react with amine, particularly can not with the mounting medium of isocyanate reaction.
DE 19917186 has described a kind of method, be used for using urea derivative to prepare defoamer preparation as hydrophobic solid, in the original position lower than the urea derivative under their fusing points described in EP-A-0 115 585, prepare neither essential, neither be favourable, on the contrary in fact by specific melting and re-crystallization step, can prepare and have the defoamer preparation that improves character, its reality changes by the methodology of melting and recrystallization condition the properties of combination that customization (tailored) is provided.In addition, due to above-mentioned side reaction, by the route described in EP-A-0 115 585, if needed, the mounting medium that precipitability crystallization is not provided can be only used in independent preparation by urea derivative, no matter to the potential reaction of amine and/or isocyanates how they.
The defect of the defoamer of described known method and thus gained is the filterability of the difference of gained defoamer, and its result is in the filtration of deposition coating that for example comprises described defoamer, and filter can stop up relatively quickly.Another defect of the defoamer of described known method and thus gained is all or part of precipitation of solid in storage process.Inhomogeneous solids distribution certainly leads to as before defoamer not to be expected and homogenize consuming time.
Therefore, the object of this invention is to provide than the defoamer of prior art and there is better filterability and the more uniform defoamer of solids distribution after storage.
Unexpectedly, while having found to prepare under the monohydric alcohol in branching exists, the defoamer that comprises urea derivative demonstrates improved filterability.
Summary of the invention
Thus, the invention provides the composition for aqueous medium froth breaking, the urea derivative of at least one formula I that it comprises solid particulate form is as defoamer,
Figure BPA00001349763200031
formula I
Wherein
R 1it is the hydrocarbon that there is the alkyl of 2-30 carbon atom or there is 3-24 carbon atom and nitrogen-atoms
Base or there is the alkyl of 2-30 carbon atom and carbonyl,
R 2hydrogen atom or the alkyl with 1-24 carbon atom,
R 3hydrogen atom or the alkyl with 1-24 carbon atom,
R 4the organic group with 2-30 carbon atom, and
N is 0-5,
Described urea derivative obtains reacting of at least one isocyanates and at least one amine in comfortable mounting medium, it is characterized in that described reaction carries out under the existence of the monohydric alcohol of formula VI,
R 8-OH
R wherein 8the alkyl of=straight chain or branching.
Define in the claims other theme of the present invention.
Therefore composition of the present invention has following advantage: solid particle demonstrates better filterability, and when defoamer used as deposition coating, obstruction or the obstruction of filter do not followed in its filtration.Composition of the present invention also has following advantage: they can have lower viscosity, more specifically has the viscosity lower than the composition of preparing according to prior art, and has therefore strengthened filtering property and the pump suction property of the medium that uses above-mentioned defoamer.
The specific embodiment
Mode is by the following examples described composition of the present invention, Its Preparation Method And Use, and its intention is not that the present invention should be limited in these exemplary embodiments.In following related scope, general formula or compounds category part, they should comprise specifically mentioned respective range or compound group, also comprise by removing all part scopes that single value (scope) or compound obtain and secondary group of compound.In this description citing document part, its content should all belong to disclosure of the present invention.In the present invention, describe and for example in multiple foundation structure, can there is the compound of different units, polyethers part for example can there is random (random oligomer or polymer) or with the distribution of orderly fashion (block oligomers or block polymer) in these unit in these compounds.The numerical value of the element number in this compound is interpreted as the average mean value of all these compounds.
For making the present composition of aqueous medium froth breaking, the urea derivative of at least one formula I that it comprises solid particulate form is as defoamer
Figure BPA00001349763200041
formula I
Wherein
R 1it is the hydrocarbon that there is the alkyl of 2-30 carbon atom or there is 3-24 carbon atom and nitrogen-atoms
Base or there is the alkyl of 2-30 carbon atom and carbonyl,
R 2hydrogen atom or the alkyl with 1-24 carbon atom,
R 3hydrogen atom or the alkyl with 1-24 carbon atom,
R 4the organic group with 2-30 carbon atom, and
N is 0-5,
Described urea derivative obtains reacting of at least one isocyanates and at least one amine in comfortable mounting medium, it is characterized in that described reaction carries out under the existence of the monohydric alcohol of formula VI,
R 8-OH
R wherein 8=straight chain or branching, be preferably the alkyl of branching, and it has 6-10, preferred 7-9, and more preferably 8 carbon atoms.If the alcohol of the formula VI advantageously using is those alcohol that only have a side chain.For the alcohol of formula VI, particularly preferably use 2-Ethylhexyl Alcohol.
In course of reaction, as the ratio of reactant mixture amine partly, the quality of the alcohol based on formula VI, is preferably 500 quality %-20 quality %, more preferably 200 quality %-50 quality %.
If advantageously make the solid particle obtaining in reaction at least once disperse under the existence of at least one dispersant.For this reason, preferably the reactant mixture of gained in reaction and mixed being incorporated in the device that is suitable for disperseing of dispersing aid are processed.Applicable device can be for example laboratory dissolvers, ceramic ball milling or prepare dissolvers.
For dispersant, can use all known dispersants that are applicable to apolar medium.For dispersant, preferably use polyethers and/or polyesters or sorbitan ester class.Preferably use those polyethers and/or the polyesters with styrene oxide unit.For example in US 2006-0183815, such polyethers and polyester have been described.The particularly preferred example with the polyether ester class of styrene units be the partially or completely reaction by following material available those:
A) one or more amino-functional fluidized polymers with
B) polyester of one or more general formulas (VII)/(VIIa)
T-C(O)-[O-A-C(O)] x-OH (VII)
T-O-[C(O)-A-O-] y-Z (VIIa)
With
C) polyethers of one or more general formulas (VIII)/(VIIIa)
T-C(O)-B-Z (VIII)
T-O-B-Z (VIIIa)
Wherein
T is hydrogen and/or optional replacement, straight chain or aryl, aralkyl, alkyl or alkenyl branching, that have 1-24 carbon atom,
A is at least one divalent group that is selected from straight chain, branching, ring-type and alkyl aromatics,
Z is at least one group that is selected from sulfonic group, sulfate, phosphonate group, phosphate, carboxylic acid group, NCO, epoxy radicals, more particularly phosphate and (methyl) acrylic,
B is the group of general formula (IX)
-(C 1H 21O) a-(C mH 2mO) b-(C nH 2nO) c-(SO) d- (IX)
SO=-CH 2-CH (Ph)-O-, Ph=phenyl wherein,
A, b and c are the value of 0-100 independently of one another,
Its condition is summation >=0 of a+b+c, is preferably 5-35,10-20 more particularly,
Its condition is the summation > 0 of a+b+c+d,
D >=0, is preferably 1-5,
L, m and n independently of one another >=2, preferred 2-4,
X and y independently of one another >=2.
Product can amide-type and/or the form of its corresponding salt exist.When in molecule, part " Z " has multiple bond, possible situation is for example for the polyethers and the polyester that start preparation from alcohol, wherein end OH base is with unsaturated acids (methyl) acroleic acid esterification for example, and keyed jointing is to realize to the Michael addition of two keys by NH functional group.
The example of amino-functional fluidized polymer is the polyaminoacid of aminofunctional, for example, purchased from the polylysine of Aldrich Chemical Co.; Commercialization Tegomer by name purchased from Degussa AG
Figure BPA00001349763200051
the amino functionalised of ASi 2122; Purchased from the commercial Polypox by name of Aldrich Chemical Co.
Figure BPA00001349763200052
aradur
Figure BPA00001349763200061
or " Starburst
Figure BPA00001349763200062
" the polyamidoamines amine of dendrimer; Purchased from the commercialization of Nitto Boseki, be called PAH and poly-(N-alkyl) allyl amine of PAA; Commercialization Lupamin by name purchased from BASF AG
Figure BPA00001349763200063
polyvinylamine; Polyalkyleneimine, for example polyethylene imine based, commercial name Epomin
Figure BPA00001349763200064
(Nippon Shokubai Co., Ltd.), Lupasol
Figure BPA00001349763200065
(BASFAG); Commercialization Astramol by name purchased from DSMAG
Figure BPA00001349763200066
polytrimethylene imines.Crosslinked by with amine reactive group, is prepared other example of amino-functional fluidized polymer by above-mentioned system.For example by multiple functionalized isocyanates, carboxylic acid, (methyl) acrylate and epoxides, carry out this cross-linking reaction.Other example is poly-(methyl) acrylate polymer, and it comprises that dimethylaminopropyl (methyl) acrylamide (Degussa AG) or (methyl) acrylic acid dimethylamino ethyl ester are as monomer.
Preferably use molecular weight at the amino-functional fluidized polymer of 400g/mol-600000g/mol.
The example of group T is the alkyl with 1-24 carbon atom, for example methyl, ethyl, propyl group, isopropyl, butyl, isobutyl group, the tert-butyl group, hexyl, isohesyl, octyl group, nonyl, different nonyl, decyl, dodecyl, cetyl and octadecyl.The example with the aryl or aralkyl of the optional replacement that is no more than 24 carbon atoms is phenyl, benzyl, tolyl or phenethyl.
Polyester-based-[O-A-C (O)] x-and-[C (O)-A-O-] y-preferably average packet contains ester group and the mean molecule quantity M more than two nfor 100-5000g/mol.M particularly preferably nvalue=200-2000g/mol.
A particularly preferred embodiment of described dispersant is by using for example T-CH of initial molecule 2-OH or T-COOH and one or more of lactone (for example beta-propiolactone, beta-butyrolactone, gamma-butyrolacton, 3,6-dimethyl-1,4-diox-2,5-diketone, δ-valerolactone, gamma-valerolactone, 6-caprolactone, γ-hexalactone, 4-methyl-caprolactone, 2-methyl caprolactone, 5-hydroxyl dodecane lactone, 12-hydroxyl dodecane lactone, 12 hydroxyls-9-octadecanoid acid and 12-hydroxyl octadecanoid acid) the conventional method of ring-opening polymerization to prepare polyester group available.
Can initial molecule prepared therefrom for example T-COOH-and fatty alcohol T-CH 2-OH is preferably this area routine and known unary fatty acid, it is based on having 6-24 carbon atom, natural plants or animal tallow and the oil more particularly with 12-18 carbon atom, caproic acid for example, sad, capric acid, laurate, myristic acid, palmitic acid, palmitoleic acid, isostearic acid, stearic acid, oleic acid, linoleic acid, petroselic acid, elaidic acid, arachidic acid, behenic acid, erucic acid, gadoleic acid, rapeseed oil fatty acid, soya fatty acid, sunflower oil aliphatic acid, ready denier oil acid, their can be used separately or with their glyceride, the form of methyl esters or ethyl ester is mixed use, or as free acid, and the cuts obtaining by pressurization cracking is used.All aliphatic acid in theory with similar chain distribution have adaptability.
The in the situation that of needs, by known catalytic hydrogenation technology, the amount of the unsaturated part in these aliphatic acid and/or fatty acid ester is adjusted to expected iodine number, or by complete all hydrogenated and unhydrided fatty ingredient is mixed and reached.
Iodine number, as the tolerance of aliphatic acid average staturation, is for by two keys iodine amount saturated and that consumed by 100g compound.
By with oxyalkylene, more particularly aliphatic acid and gained alcohol described in the addition reaction correctability of ethylene oxide and/or styrene oxide.
The example of B polyether units is following oxyalkylene: ethylene oxide, propylene oxide, butylene oxide, styrene oxide, oxidation laurylene, oxidation tetradecene, 2, 3-dimethyl ethylene oxide, cyclopentene oxide, 1, 2-epoxy pentane, 2-isopropyl oxirane, glycidol methyl esters, glycidol isopropyl ester, chloropropylene oxide, 3-methoxyl group-2, 2-dimethyl ethylene oxide, 8-oxabicyclo [5, 1, 0] octane, 2-amyl group oxirane, 2-methyl-3-phenyl ethylene oxide, 2, 3-glycidyl benzene, 2-(4-fluorophenyl) oxirane, oxolane and their pure enantiomer counter pair or mixture of enantiomers.
Group Z can form from carboxylic acid anhydrides, as the addition compound product of succinyl oxide, maleic anhydride or phthalic anhydride.
In preferred dispersant polyester to the weight ratio of polyethers preferably at 50: 1 to 1: 9, more preferably at 40: 1 to 1: 5, and most preferably at 30: 1 to 1: 1.
Other details of the dispersant preferably using can be with reference to as the full text of US-2006-0183815, and be intended to its disclosure to comprise in the present disclosure of the invention.
Composition of the present invention comprises urea derivative, R in its preferred kind 1be to have 2-30 carbon atom, preferably have 2-20, more preferably the alkyl of 12-18 carbon atom is, the organic group of formula II or the organic group of formula III
Figure BPA00001349763200071
formula II,
R 5to there is 1-8 carbon atom, the alkyl of preferred 1-6 carbon atom,
Figure BPA00001349763200072
formula III,
R 6be to there is 2-30 carbon atom, preferably there is the organic group of 2-20 carbon atom, and radicals R 2hydrogen atom, radicals R 3hydrogen atom, and radicals R 4to there is 1-30, preferably 1-12, and the more preferably alkyl of 2-6 carbon atom.
A same preferred composition comprises urea derivative, R in its preferred kind 1to there is 2-30, the alkyl of preferred 2-20 carbon atom, R 2and R 3hydrogen atom, and R 4it is organic group
Figure BPA00001349763200081
formula IV,
R 7to there is 1-30, the alkyl of preferred 1-12 carbon atom.
Composition of the present invention can be by reacting all lists or polyisocyanates to acquisition with all list or polyamine compounds.The example of spendable monoisocyanates comprises by phosgenation reaction from the available all isocyanates of known monoamine.Applicable monoisocyanates is isocyanic acid 2-Octyl Nitrite, the different tridecane ester of isocyanic acid, isocyanic acid palm-stearyl ester or isocyanic acid C more particularly 18-C 24arrcostab.Preferred applicable isocyanates is isocyanic acid lauryl, isocyanic acid octadecane ester, two isocyanic acids 1,6-six methylene esters, isocyanic acid stearyl ester and/or isocyanic acid palm ester or their mixture.
For amine, can use single or multiple functionalized amine.The amine preferably using comprises product, ethylenediamine, propane diamine, butanediamine, the hexamethylene diamine, 1 of octylame, diethyl triamine, oleyl amine, stearylamine, distearyl amine, stearylamine and hexamethylene diamine and toluene di-isocyanate(TDI), 12-dodecane diamines, 4,4 '-diaminodiphenyl-methane, 3,3 '-dimethyl-4,4 '-diaminodiphenyl-methane, the mixture to sub-dimethylphenylene diamine, IPD or hydrazine and these amine of two or more.
Preferably use isocyanic acid stearyl ester as isocyanates and propane diamine as amine.
For mounting medium, can use at least one organic oil and/or at least one mineral oil.This oil can be natural oil for example, as soybean oil or sunflower oil, or for example paraffinic base bobbin oil or naphthyl or aromatic mineral oil.For mounting medium, preferably use at least one siloxanes and/or siloxanes that at least one is organically-modified.It is same applicable that what make mounting medium is the ester of gasoline, dimethylbenzene, toluene, medicinal white oils, LCFA (having the chain more than 4 carbon atoms) for example, for example isobutyl stearate or Ethylhexyl stearate, or the composition of PAG and these products and described oil or siloxanes for example.
The urea derivative of the present composition is preferably 0.002 to the mass ratio of mounting medium: 1-1: 1, more preferably 0.01: 1-0.20: 1.
By adding emulsifying agent, the composition that the present invention can be used for to froth breaking is converted into water-based emulsion.Those (HLB is according to W.C.Griffin, " Classification of surface active agents by HLB ", J.Soc.Cosmetic Chemists 1,311 (1950)) that spendable emulsifying agent comprises that HLB is for example 4-18.Preferably use nonionic emulsifier.More preferably the emulsifying agent using is ethoxylate, nonyl phenol ethoxylate, sorbitan ester and the fatty acid ethoxylate of for example fatty alcohol.Based on mounting medium, in the ratio of the composition emulsifying agent for froth breaking of the present invention preferably at 1 quality %-10 quality %.
In a preferred embodiment, of the present invention for making the composition of aqueous medium froth breaking by forming below:
A. defoamer, wherein at least one and be preferably all the derivative of the above-mentioned formula I of solid particulate form,
B. one or more of mounting medium as above,
C. the monohydric alcohol of one or more of formula VI as above,
D. the one or more of dispersant optionally existing,
E. the one or more of emulsifying agent optionally existing, and
F. the water optionally existing.
In an especially preferred embodiment, of the present invention for making the composition of aqueous medium froth breaking by forming below:
A. defoamer, wherein at least one and be preferably all the above-mentioned formula I of solid particulate form
Derivative,
B. one or more of mounting medium as above,
C. the monohydric alcohol of one or more of formula VI as above, and
D. one or more of dispersant.
Preferably, the mass fraction of component a is 5-40, and components b is 25-75, and amount of component b is 1-10.Particularly preferably, the mass fraction of component a is 10-30, and components b is 40-60, and amount of component b is 2-5.In the situation that one or more of dispersing additives are present in composition of the present invention, based on a, the mass fraction that they preferably exist is 0.75: 1-1.25: 1, and more preferably 1: 1.
Composition of the present invention can obtain by all known methods of preparing urea derivative, and its condition is under the existence of the monohydric alcohol of formula VI, to carry out reacting of isocyanate compound and amines.Described reaction is preferably being carried out according to the method route described in DE 32 45 482.
More preferably by following method of the present invention, prepare the composition for froth breaking of the present invention.
For the preparation of making in the defoamer of aqueous medium froth breaking or the inventive method of composition, under the fusing point of the urea derivative of the formula I lower than gained, under the existence of the alcohol of formula VI, isocyanates is reacted to obtain the urea derivative of formula I in a kind of above-mentioned mounting medium with amine.For alcohol, preferably use a kind of in above-mentioned alcohol, preferably 2-Ethylhexyl Alcohol.Preferably so that the amount of mass fraction in above-mentioned preferable range adds described alcohol in reactant mixture.
Preferably carry out described reaction so that first described mounting medium mixes with the alcohol of formula VI, and this mixture first mixes with amine, and mix with isocyanates subsequently, it preferably follows continuous stirring.
For isocyanates, can use single or multiple functionalized isocyanates.For monoisocyanates, for example, can use by phosgenation reaction from the available all isocyanates of known monoamine, more specifically isocyanic acid 2-Octyl Nitrite, the different tridecane ester of isocyanic acid, isocyanic acid palm-stearyl ester or isocyanic acid C 18-C 24arrcostab.For isocyanates, preferably use isocyanic acid stearyl ester and/or isocyanic acid palm ester or their mixture.
For amine, can use single or multiple functionalized amine.The amine preferably using comprises product, ethylenediamine, propane diamine, butanediamine, the hexamethylene diamine, 1 of oleyl amine, stearylamine, distearyl amine, stearylamine and hexamethylene diamine and toluene di-isocyanate(TDI), 12-dodecane diamines, 4,4 ' diaminodiphenyl-methane, 3,3 '-dimethyl-4,4 '-diaminodiphenyl-methane, two or more the mixture to sub-dimethylphenylene diamine, IPD or hydrazine and these amine.
Preferably use isocyanate functional group to the equivalent proportion of amine functional group 0.5: 1-1: 0.2, preferably 1: 1.2-1: 0.8 enough isocyanates and amine.
Particularly preferably use propane diamine as amine and isocyanic acid stearyl ester as isocyanates.When using these reactants, reaction preferably at 20-60 ℃, is carried out under in using with the agitator of 50-1000 rev/min of lower hybrid reaction mixture.
Gained reactant mixture can be directly as the composition that makes aqueous medium froth breaking.
Preferably, as before making the composition of aqueous medium froth breaking, after adding a kind of above-mentioned dispersant, gained reactant mixture is disperseed.For this reason, preferably dispersing aid is added in and reacts in the reactant mixture obtaining, and process the reactant mixture mixing in being suitable for the device disperseing.Applicable device can be as laboratory dissolvers, ceramic ball milling or prepare dissolvers.
Advantageously directly filter before use gained reactant mixture or filter the reactant mixture through disperseing.This can preferably be undertaken by 25 μ m filters.
Composition of the present invention can be used for for example making cooling lubricant, polymeric dispersions, coating and/or printing-ink froth breaking with the composition (defoamer) that derives from the inventive method.Therefore, the present invention also provides and comprises the present invention for the aqueous medium of the composition of froth breaking, more particularly cooling lubricant, polymeric dispersions, coating (preferred deposition coating) or printing-ink.
By with reference to embodiment, the present invention being described, its intention is not that the present invention is limited in these embodiments below.
Embodiment:
Embodiment 1-12: the preparation of defoaming composition of the present invention
In the container stirring, add 50g carrier material (according to table 1), be heated to temperature Y, and mix with 5g amine and 1g alcohol, and stir this mixture until it is completely even.After adding the isocyanates ISO of equimolar amounts under low whipping speed Z, there is the rear time t of reaction.Optionally under low whipping speed Z, add dispersing additive subsequently, to add the amount of dispersant to make dispersant be 1: 1 to the mass ratio of the total amount of used amine and isocyanates.
Embodiment 13-17: the preparation of contrast defoamer
Do not use alcohol of the present invention, and do not use dispersant, prepare in an identical manner non-defoamer of the present invention.
The carrier material using is as follows:
T1＝Ecolane 100(Total Deutschland GmbH)
The Ecolane 100 of T2=80 % by weight (Total Deutschland GmbH) and 20 quality %'s
Figure BPA00001349763200111
the mixture of 110 (Evonik Goldschmidt GmbH) DD
The Indopol H 2100 (Innovene) of T3=10 % by weight and the poly-1-decene (50Mpas) of 90 % by weight, the mixture of (Aldrich Deutschland GmbH)
T4＝Nynas T 22(
Figure BPA00001349763200112
Petroleum(Stockholm，Sweden))
T5＝TEGO STAB 8932(BP 18100)(Evonik Goldschmidt GmbH)
The lithene PM (Sartomer) of T6=50 % by weight and 50 % by weight
Figure BPA00001349763200113
110 (Evonik Goldschmidt GmbH)
The amine using is as follows:
A1=propane diamine
A2=octylame
A3=diethyl triamine
The alcohol using is as follows:
ROH 1=2-ethyl hexanol
ROH 2=3,5,5-trimethyl hexanol
The dispersing additive using is as follows:
DA1＝TEGO Dispers 685
DA2＝TEGO Dispers 650
DA3=TEGO SMOV (all from Evonik Goldschmidt GmbH)
The isocyanates using is as follows:
ISO 1=isocyanic acid lauryl
ISO 2=isocyanic acid octadecane ester
ISO 3=bis-isocyanic acids 1,6-bis-methylene esters
Embodiment 18: the evaluation of sedimentation character:
In order to evaluate the sedimentation of solid in defoamer, the defoamer of embodiment 1-17 is at room temperature stored to 1 week, then according to any visual assessment sedimentation character that is separated occurring.
Embodiment 19: filterability evaluation:
In order to evaluate filterability, by deriving from Erich Drehkopf GmbH, each defoamer of the quick E-D-Schnellsieb sieve filter 23 0g embodiment 1-17 that the mesh size of Lerchenberg 35,22359 Hamburg is 80 microns.After 15 minutes, filtrate is weighed and determine thus the filterability of product.In filtration residue, be less than in the situation of 0.5g, described product is defined as filterable.In filtration residue, be greater than in the situation of 1g, described product classified as not filterable.
Embodiment 18 and 19 result see table 1.
In the result of listing as table 1, know to show, embodiments of the invention (embodiment 1-12) they sedimentation character and filterability on be significantly better than non-embodiments of the invention (embodiment 13-17).
Application Example 20: the application in two component coating
In order to test the degassed activity of defoaming composition or defoamer, according to following formula, prepare tested media and evaluate:
Table 2:
1: the two component coating of filling a prescription
Figure BPA00001349763200141
Use Dispermat under 3000rpm by 50g mentioned component homogenize 3 minutes, the agitator disk of 3cm diameter is immersed to the mixture for the treatment of homogenize to position mostly.In this operation, by the method to limit, disperse to mix air.The diameter of the straight tube homogenize container using in this step is 6.5cm.48g gained coating is poured in petri diss (diameter 14cm), and at room temperature solidified 7 days.
According to the visually rank at the lip-deep irregularity of test system (irregularities) (as the air bubble of sealing), after solidifying, determine its performance.Diameter is more than or equal to 0.5mm/cm 2be less than 0.5mm/cm 2irregularity distinguish.In table 3, gather its result.
Table 3: the performance test results in two component coating
The defoamer adding Be more than or equal to the irregularity of 0.5mm Be less than the irregularity of 0.5mm
Nothing 57 87
From embodiment 2 0 12
From embodiment 4 3 9
From embodiment 7 0 11
From embodiment 8 1 10
From embodiment 11 1 9
From embodiment 12 0 11
From embodiment 13 16 43
From embodiment 14 12 24
From embodiment 15 32 23
From embodiment 17 28 47
As known in the embodiment being reported, show, embodiments of the invention (embodiment 2,4,7,8,11,12) are significantly better than non-embodiments of the invention (embodiment 13-15 and 17) in froth breaking activity.
Embodiment 21: the froth breaking active testing in the dispersion of commercial polymer
Cinnamic acrylic ester dispersion Acronal at BASF
Figure BPA00001349763200151
290D and at the pure acrylic acid ester dispersion Acronal of BASF
Figure BPA00001349763200152
in A603, test.
In 1 minute, with 1000rpm, the present invention and non-defoamer of the present invention are mixed in described dispersion separately.
Use turbine stirrer (diameter 4cm) with 2500rpm, air dispersion to be entered to be added with the polymeric dispersions 1 minute of defoamer.After agitator is closed down, add measuring cylinder to 50ml graticule the dispersion of processing thus immediately, and weigh.This weight is subject to the impact of the air capacity that adds by stirring, and is the tolerance of defoamer validity.Embodiment 21 the results are summarized in table 4 and 5.
Table 4: at polymeric dispersions Acronal
Figure BPA00001349763200161
the performance test results in 290D
Defoamer The amount of defoamer (% by weight) Sample rate (g/50ml)
Do not add - 39.4
Embodiment 10 0.25 49.5
Embodiment 11 0.055 48.4
Embodiment 15 0.25 43.1
Embodiment 16 0.055 42.1
Table 5: at polymeric dispersions Acronal the performance test results in A603
Defoamer The amount of defoamer (% by weight) Sample rate (g/50ml)
Do not add - 37.1
Embodiment 10 0.25 48.2
Embodiment 11 0.055 49.7
Embodiment 15 0.25 41.5
Embodiment 16 0.055 46.9
As known in the embodiment being reported, show, embodiments of the invention (embodiment 10 and 11) are significantly better than non-embodiments of the invention (embodiment 15 and 16) in their froth breaking activity.
Application Example 22: the application in one-component coating
In order to test the degassed activity of auxiliary agent, according to following formula, prepare test system and evaluate: the preparation of one pack system PU finish paint:
Use dissolvers with 2000rpm by the component homogenize of describing in table 6 15 minutes.Then the bead that adds 50g diameter 3mm, and disperse 45 minutes with 3350rpm.
Table 6: the preparation of abrasive
Figure BPA00001349763200171
Sieve to remove after bead, ground as shown in table 7 further machining obtains abrasive.
Table 7: the preparation of finish paint
Component Consumption (g) Adding mode
Abrasive 46.73 Add
Bayhydrol VPLS 2227 40.48 Under stirring, add
Cymel 327 6.11 Under stirring, add
Deionized water 6.68 Under stirring, add
With 1000rpm, the present invention who is reported in table 8 and non-defoamer of the present invention are mixed in finish paint 1 minute separately.
With turbine stirrer (diameter 4cm), with 3000rpm, air dispersion is entered to be added with the polymeric dispersions 3 minutes of defoamer.After agitator is closed down, immediately the dispersion of processing thus of 45g amount is added in 100ml measuring cylinder, and read volume.This volume is stirred down the impact of the amount of the air adding, and is the tolerance of defoamer validity.Table 8 has provided the result of Application Example 22.
Table 8: the performance test results in one pack system PU finish paint
Defoamer The amount of defoamer (% by weight) Sample rate (ml/45g)
Do not add - 57
Embodiment 10 1 49.5
Embodiment 11 1 48.4
Embodiment 15 1 53.1
Embodiment 16 1 52.1
As at table 8 know demonstration, use the finish paint from the defoamer of the present invention of embodiment 10 or 11 in their degassed property, to be better than significantly using the finish paint from the non-defoamer of the present invention of embodiment 15 and 16.

Claims (15)

1. for making the composition of aqueous medium froth breaking, it comprises
A. the urea derivative of at least one formula I of solid particulate form is as defoamer,
Figure FDA0000367725630000011
Wherein
R 1there is the alkyl of 4-30 carbon atom or there is the alkyl of 4-24 carbon atom and nitrogen-atoms or there is the alkyl of 4-30 carbon atom and carbonyl,
R 2hydrogen atom or the alkyl with 1-24 carbon atom,
R 3hydrogen atom or the alkyl with 1-24 carbon atom,
R 4the organic group with 2-30 carbon atom, and
N is 0-5,
Described urea derivative obtains reacting of at least one isocyanates and at least one amine in comfortable mounting medium, it is characterized in that described reaction carries out under the existence of the monohydric alcohol of formula VI,
R 8-OH
R wherein 8alkyl=straight chain or branching, that there is 6-10 carbon atom;
B. one or more above-mentioned mounting mediums;
C. the monohydric alcohol of one or more above-mentioned formula VI;
D. one or more dispersants that optionally exist;
E. one or more emulsifying agents that optionally exist; With
F. the water optionally existing.
2. composition claimed in claim 1, is characterized in that the described solid particle obtaining in described reaction is dispersed at least once under the existence of at least one dispersant.
3. composition claimed in claim 2, is characterized in that polyethers or polyester to be used as dispersant.
4. the composition described in claim 2 or 3, is characterized in that polyethers or the polyester with styrene oxide unit to be used as dispersant.
5. the composition described in any one in claim 1-3, is characterized in that R 1the organic group with the alkyl of 4-24 carbon atom, the organic group of formula II or formula III:
Figure FDA0000367725630000021
R 5the alkyl with 1-18 carbon atom,
R 6the organic group with 2-30 carbon atom,
R 2hydrogen atom, R 3hydrogen atom, and R 4it is the alkyl with 2-24 carbon atom.
6. the composition described in any one in claim 1-3, is characterized in that R 1the alkyl with 2-24 carbon atom, R 2and R 3hydrogen atom, and R 4it is organic group below
Figure FDA0000367725630000023
R 7it is the alkyl with 2-20 carbon atom.
7. the composition described in any one in claim 1-3, is characterized in that isocyanic acid stearyl ester to be used as described isocyanates, and propane diamine is used as to described amine.
8. the composition described in any one in claim 1-3, is characterized in that at least one organic oil and/or at least one mineral oil to be used as described mounting medium.
9. the composition described in any one in claim 1-3, is characterized in that at least one siloxanes and/or siloxanes that at least one is organically-modified as described mounting medium.
In claim 1-9 the composition for froth breaking described in any one in the purposes that makes cooling lubricant, polymeric dispersions, coating and printing-ink froth breaking.
11. aqueous mediums, it comprises the composition for froth breaking described in any one in claim 1-9.
Aqueous medium described in 12. claims 11, is characterized in that it is cooling lubricant, polymeric dispersions, coating or printing-ink.
Aqueous medium described in 13. claims 11 or 12, is characterized in that it is deposition coating.
14. prepare in claim 1-9 the method for composition described in any one, it is characterized in that obtaining by least one isocyanates in mounting medium and reacting of at least one amine the urea derivative of formula I, described reaction, at the temperature of the fusing point of the urea derivative lower than gained, is carried out under the existence of the monohydric alcohol of formula VI
R8-OH
Alkyl R8=straight chain or branching, that there is 6-10 carbon atom wherein.
Method described in 15. claims 14, is characterized in that the reactant mixture obtaining in reaction directly to filter, or filters the reactant mixture through disperseing after adding dispersant to disperse.
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