US20100029519A1 - Performance additives for improving the wetting properties of ionic liquids on solid surfaces - Google Patents

Performance additives for improving the wetting properties of ionic liquids on solid surfaces Download PDF

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Publication number
US20100029519A1
US20100029519A1 US12/363,960 US36396009A US2010029519A1 US 20100029519 A1 US20100029519 A1 US 20100029519A1 US 36396009 A US36396009 A US 36396009A US 2010029519 A1 US2010029519 A1 US 2010029519A1
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Prior art keywords
radical
methyl
methylimidazolium
composition according
butyl
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US12/363,960
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Peter Schwab
Stefan Kempka
Matthias Seiler
Bernd Gloeckler
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Evonik Operations GmbH
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Individual
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Assigned to EVONIK GOLDSCHMIDT GMBH reassignment EVONIK GOLDSCHMIDT GMBH ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: KEMPKA, STEFAN, SEILER, MATTHIAS, DR., GLOECKLER, BERND, SCHWAB, PETER, DR.
Publication of US20100029519A1 publication Critical patent/US20100029519A1/en
Assigned to EVONIK DEGUSSA GMBH reassignment EVONIK DEGUSSA GMBH MERGER (SEE DOCUMENT FOR DETAILS). Assignors: EVONIK GOLDSCHMIDT GMBH
Abandoned legal-status Critical Current

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    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
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    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
    • C23G5/06—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using emulsions
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D21H21/22—Agents rendering paper porous, absorbent or bulky
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2207/283—Esters of polyhydroxy compounds
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    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
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    • 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
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    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • 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
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    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
    • C10M2211/044—Acids; Salts or esters thereof
    • C—CHEMISTRY; METALLURGY
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    • C10M2211/06—Perfluorinated compounds
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/08—Amides
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/08—Amides
    • C10M2215/082—Amides containing hydroxyl groups; Alkoxylated derivatives
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/20—Containing nitrogen-to-oxygen bonds
    • C10M2215/206—Containing nitrogen-to-oxygen bonds hydroxylamines
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/047—Thioderivatives not containing metallic elements
    • C—CHEMISTRY; METALLURGY
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/077—Ionic Liquids
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C—CHEMISTRY; METALLURGY
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    • C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
    • C11D2111/10—Objects to be cleaned
    • C11D2111/14—Hard surfaces
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
    • H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
    • H01G9/20—Light-sensitive devices
    • H01G9/2004—Light-sensitive devices characterised by the electrolyte, e.g. comprising an organic electrolyte
    • H01G9/2013—Light-sensitive devices characterised by the electrolyte, e.g. comprising an organic electrolyte the electrolyte comprising ionic liquids, e.g. alkyl imidazolium iodide

Definitions

  • the invention relates to improving the wetting properties of ionic liquids on solid surfaces.
  • Ionic liquids are used and have been proposed for numerous applications in which the wetting of solid surfaces plays an important role. Examples of such applications are use as lubricant and in separation processes, in particular distillative separation processes. Ionic liquids often have an unsatisfactory wetting and spreading behavior and therefore prove to be unsuitable despite an excellent property profile because of this deficiency.
  • the correct wetting properties of the liquids can substantially improve performance in the application.
  • One object of the invention is a composition which comprise from 50 to 99.999% by weight, preferably from 80 to 99.999% by weight, in particular at least 95% by weight and particularly preferably from >98 to 99.999% by weight, of one or more ionic liquids,
  • the amount of solvents, auxiliaries and/or additives is present in the composition in an amount of at least 0.01% by weight.
  • the ionic liquid itself is present in a very high concentration and should be optimized in terms of its performance in, for example, lubrication by means of a performance additive.
  • the water or solvent concentration is normally also of importance in addition to the ionic liquid.
  • the invention does not intend to encompass within the scope of the invention any previously disclosed product, process of making the product or method of using the product, which meets the written description and enablement requirements of the USPTO (35 U.S.C. 112, first paragraph) or the EPO (Article 83 of the EPC), such that applicant(s) reserve the right and hereby disclose a disclaimer of any previously described product, method of making the product or process of using the product.
  • ionic liquids are salts of the general Formulae I, II or III:
  • n 1, 2, 3 or 4
  • [A] + is a quaternary ammonium cation, an oxonium cation, a sulphonium cation or a phosphonium cation
  • [Y] n ⁇ is a monovalent, divalent, trivalent or tetravalent anion; or mixed salts of the general Formulae (II)
  • [A 1 ] + , [A 2 ] + and [A 3 ] + are selected independently from among the groups mentioned for [A] + , [Y] n ⁇ is as defined for Formula (I) and [M 1 ] + , [M 2 ] + , [M 3 ] + are monovalent metal cations, [M 4 ] 2+ is a divalent metal cation and [M 5 ] 3+ is a trivalent metal cation; or mixtures of all Formulae (I) to (III).
  • Ionic liquids comprise, for example, anions such as halides, carboxylates, phosphates, thiocyanates, isothiocyanates, dicyanamides, sulphates, alkylsulphates, sulphonates, alkylsulphonates, tetrafluoroborate, hexafluorophosphate or bis(trifluoromethylsulphonyl)imide combined with, for example, substituted ammonium, phosphonium, pyridinium or imidazolium cations, with the abovementioned anions and cations representing a small selection from the large number of possible anions and cations and no claim to completeness therefore being made or any restriction being imposed.
  • anions such as halides, carboxylates, phosphates, thiocyanates, isothiocyanates, dicyanamides, sulphates, alkylsulphates, sulphonates, alkylsulphonates, tetrafluorobo
  • the ionic liquids used according to the invention are preferably composed of at least one quaternary nitrogen and/or phosphorus compound and/or sulphur compound and at least one anion and their melting points are below about +250° C., preferably below about +150° C., in particular below about +100° C.
  • the ionic liquids used according to the invention or mixtures thereof are particularly preferably liquid at room temperature.
  • the ionic liquids which are preferably used for the purposes of the invention can, for example, be composed of at least one cation of the general formulae:
  • alkanolamine ester quats Preference is given to quaternary ammonium salts of alkylated fatty acids, also referred to as alkanolamine ester quats, characterized by the generic formula of the type R 1 R 2 R 3 R 4 N + A ⁇ (IV) where R 1 is an alkyl radical having from 1 to 20 carbon atoms, R 2 is an alkyl radical having from 1 to 4 carbon atoms, R 3 is a (CH 2 CHRO) n —H radical where n is from 1 to 200 and R is H or CH 3 , R 4 is an alkyl radical having from 1 to 4 carbon atoms or a (CH 2 CHRO) n —H radical where n is from 1 to 200 and R is H or CH 3 and A ⁇ is a monovalent anion.
  • R 1 is an alkyl radical having from 1 to 20 carbon atoms
  • R 2 is an alkyl radical having from 1 to 4 carbon atoms
  • R 3 is a (CH 2 CHRO
  • each radical R 6 is independently an alkyl group or hydroxyalkyl group having from 1 to 6 carbon atoms, or a benzyl group, preferably a methyl group
  • the radicals R 7 are each, independently of one another, hydrogen, a linear or branched alkyl group having from 11 to 22 carbon atoms, a linear or branched alkenyl group having from 11 to 22 carbon atoms, with the proviso that at least one radical R 7 is not hydrogen
  • Q is selected independently from among the groups of the formulae —O—CO)—, —C(O)O, —NR 8 —C(O)—, —C(O)—NR 8 —, —O—C(O)—O, —CHR 9 —O—C(O)— or —CH(OCOR 7 )—CH 2 —O—C(O)—, where R 8 is hydrogen, methyl, ethyl, propyl or butyl and R 9 is hydrogen or methyl, and Q
  • the quaternary ammonium compounds can contain mixtures of the compounds which have different groups R 7 which are not hydrogen whose value extends from 1 to m. Such mixtures preferably have an average of from 1.2 to 2.5 groups R 7 which are not hydrogen.
  • the proportion of nonhydrogen groups R 7 is preferably from 1.4 to 2.0 and more preferably from 1.6 to 1.9.
  • Preferred quaternary ammonium compounds are the compounds of the type:
  • R 6 , R 7 and X are as defined above for Formula (I), with the proviso that R 7 is not hydrogen.
  • the moiety —C(O)R 7 is preferably a fat-containing acyl group.
  • Fat-containing acyl groups which can be used are derived from natural sources of triglycerides, preferably tallow, vegetable oils, partially hydrogenated tallow and partially hydrogenated vegetable oils. Sources of triglycerides which can be used are soybean oil, tallow, partially hydrogenated tallow, palm oil, palm kernels, rapeseeds, lard, coconut, rape, safflower oil, maize, rice and tall oil and mixtures of these components.
  • compositions of the fatty acid-containing compounds are subject to certain natural fluctuations, depending on harvest to harvest or on the many vegetable oil sources.
  • the R 7 groups are usually mixtures of linear and branched carbon chains of the saturated and unsaturated aliphatic fatty acids.
  • the proportion of unsaturated groups R 7 in such mixtures is preferably at least 10%, particularly preferably at least 25% and very particularly preferably from 40 to 70%.
  • the proportion of multiply unsaturated groups R 7 in such mixtures is less than 10%, preferably less than 5% and particularly preferably less than 3%. If necessary, partial hydrogenation can be carried out in order to increase the saturated character and thus improve the stability (e.g. odour, colour, etc.) of the end product.
  • the content of unsaturated material, expressed by the iodine number should be in the range from 5 to 150 and preferably in the range from 5 to 50.
  • the ratio of cis and trans isomers of the double bonds in the unsaturated groups R 7 is preferably greater than 1:1 and particularly preferably in the range from 4:1 to 50:1.
  • quaternary ammonium salts are ditallowedimethylammonium chloride, ditallowedimethylammonium methylsulphate, dimethylammonium chloride of di(hydrogenated tallow) distearyldimethylammonium chloride and dibehenyldimethylammonium chloride.
  • cations are ions derived from saturated or unsaturated cyclic compounds or from aromatic compounds having in each case a trivalent nitrogen atom in a 4- to 10-membered, preferably 5- or 6-membered, heterocyclic ring which may be substituted.
  • Such cations can be described in simplified form (i.e. without indication of the precise position and number of the double bonds in the molecule) by the general Formulae (XIII), (XIV) and (XV), where the heterocyclic rings may, if appropriate, also contain a plurality of heteroatoms.
  • R 1 and R 2 are as defined above,
  • cyclic nitrogen compounds of the abovementioned type are pyrrolidine, dihydropyrrole, pyrrole, imidazoline, oxazoline, oxazole, thiazoline, thiazole, isoxazole, isothiazole, indole, carbazole, piperidine, pyridine, the isomeric picolines and lutidines, quinoline and isoquinoline.
  • Examples of such compounds are pyrazole, 3,5-dimethylpyrazole, imidazole, benzimidazole, N-methylimidazole, dihydropyrazole, pyrazolidine, pyridazine, pyrimidine, pyrazine, 2,3-, 2,5- and 2,6-dimethylpyrazine, cinnoline, phthalazine, quinazoline, phenazine and piperazine. Cations derived from imidazole and its alkyl and phenyl derivatives have been found to be particularly useful as constituents of ionic liquids.
  • Possible cations also include ions which contain two nitrogen atoms and are represented by the general Formula (XVI)
  • imidazolium ions mention may be made of 1-methylimidazolium, 1-ethylimidazolium, 1-(1-butyl)imidazolium, 1-(1-octyl)imidazolium, 1-(1-dodecyl)imidazolium, 1-(1-tetradecyl)imidazolium, 1-(1-hexadecyl)imidazolium, 1,3-dimethylimidazolium, 1-ethyl-3-methylimidazolium, 1-(1-butyl)-3-methylimidazolium, 1-(1-butyl)-3-ethylimidazolium, 1-(1-hexyl)-3-methylimidazolium, 1-(1-hexyl)-3-ethylimidazolium, 1-(1-hexyl)-3-methylimidazolium, 1-(1-hexyl)-3-ethylimidazolium,
  • ionic liquids are those in which the cation [A] + is a pyridinium ion (XVIIa),
  • pyridinium ions As very particularly preferred pyridinium ions (XVIIa), mention may be made of 1-methylpyridinium, 1-ethylpyridinium, 1-(1-butyl)pyridinium, 1-(1-hexyl)pyridinium, 1-(1-octyl)pyridinium, 1-(1-hexyl)pyridinium, 1-(1-octyl)pyridinium, 1-(1-dodecyl)pyridinium, 1-(1-tetradecyl)pyridinium, 1-(1-hexadecyl)pyridinium, 1,2-dimethylpyridinium, 1-ethyl-2-methylpyridinium, 1-(1-butyl)-2-methylpyridinium, 1-(1-hexyl)-2-methylpyridinium, 1-(1-octyl)-2-methylpyridinium, 1-(1-dodecyl)-2-methyl
  • ionic liquids are those in which the cation [A] + is a pyrazinium ion (XVIId),
  • ionic liquids are those in which the cation [A] + is a pyrazolium ion (XVIIf), (XVIIg) or (XVIIg′),
  • Possible ionic liquids are additionally those in which the cation [A] + is a pyrazolium ion (XVIIh),
  • Suitable ionic liquids also include those in which the cation [A] + is a 1-pyrazolinium ion (XVIIi),
  • ionic liquids are those in which the cation [A] + is a 2-pyrazolinium ion (XVIIj),
  • ionic liquids are those in which the cation [A] + is an imidazolinium ion (XVIIl),
  • Additional possible ionic liquids are those in which the cation [A] + is an imidazolinium ion (XVIIm) or (XVIIm′),
  • ionic liquids are those in which the cation [A] + is an imidazolinium ion (XVIIn) or (XVIIn′),
  • Additional possible ionic liquids are those in which the cation [A] + is a thiazolium ion (XVIIo) or (XVIIo′) or an oxazolium ion (XVIIp),
  • Possible ionic liquids also include those in which the cation [A] + is a 1,2,4-triazolium ion (XVIIq), (XVIIq′) or (XVIIq′′),
  • ionic liquids are those in which the cation [A] + is a 1,2,3-triazolium ion (XVIIr), (XVIIr′) or (XVIIr′′),
  • ionic liquids are those in which the cation [A] + is an imidazolidinium ion (XVIIt),
  • Possible ionic liquids also include those in which the cation [A] + is an ammonium ion (IV),
  • ammonium ions (IV) mention may also be made of methyltri(1-butyl)ammonium, 2-hydroxyethylammonium, bis(2-hydroxyethyl)dimethylammonium, N,N-dimethylpiperidinium and N,N-dimethylmorpholinium.
  • Possible ionic liquids also include those in which the cation [A] + is a derivative of ethanolamine, e.g. a cholinium ion (XVIIw), or of a diethanolamine (XVIIw′), or of a triethanolamine (XVIIw′′),
  • XVIIw cholinium ion
  • XVIIw′ diethanolamine
  • XVIIw′′ triethanolamine
  • R, R 1 and R 2 are alkyl groups having from 1 to 4 carbon atoms, particularly preferably a methyl group
  • R 3 and/or R 4 are saturated or unsaturated fatty acid or acyl radicals having from 8 to 22 carbon atoms, preferably from 12 to 18 carbon atoms. It is also possible for mixtures of the acyl or fatty acid radicals (in particular, for example, in naturally occurring ratios) to be present.
  • R 1 , R 2 each being an alkyl radical having from 1 to 4 carbon atoms, in particular a methyl group
  • R 3 being a fatty acid radical
  • R 4 and R 5 each being a fatty acid radical or hydrogen.
  • Possible ionic liquids include those in which the cation [A] + is a phosphonium ion (VI), where
  • pyridinium ions XVIIa
  • imidazolium ions XVI
  • ammonium ions IV
  • 1-methylpyridinium 1-ethylpyridinium, 1-(1-butyl)pyridinium, 1-(1-hexyl)pyridinium, 1-(1-octyl)pyridinium, 1-(1-hexyl)pyridinium, 1-(1-octyl)pyridinium, 1-(1-dodecyl)pyridinium, 1-(1-tetradecyl)pyridinium, 1-(1-hexadecyl)pyridinium, 1,2-dimethylpyridinium, 1-ethyl-2-methylpyridinium, 1-(1-butyl)-2-methylpyridinium, 1-(1-hexyl)-2-methylpyridinium, 1-(1-octyl)
  • the metal cations [M 1 ] + , [M 2 ] + , [M 3 ] + , [M 4 ] 2+ and [M 5 ] 3+ mentioned in the Formulae (IIIa) to (IIIj) are generally metal cations of groups 1, 2, 6, 7, 8, 9, 10, 11, 12 and 13 of the Periodic Table. Suitable metal cations are, for example, Li + , Na + , K + , Cs + , Mg 2+ , Ca 2+ , Ba 2+ , Cr 3+ , Fe 2+ , Fe 3+ , Co 2+ , Ni 2+ , Cu 2+ , Ag + , Zn 2+ and Al 3+ .
  • the ionic liquids used according to the invention comprise at least one of the abovementioned cations combined with at least one anion.
  • Possible anions are in principle all anions which in combination with the cation lead to an ionic liquid.
  • the anion [Y] n ⁇ of the ionic liquid is selected, for example, from:
  • R a , R b , R c and R d are each, independently of one another,
  • Possible anions are, for example, chloride; bromide; iodide; thiocyanate; hexafluorophosphate; trifluoromethanesulphonate; methanesulphonate; formate; acetate; glycolate; lactate; oxalate; citrate; malate; maleate; tartrate; mandelate; nitrate; nitrite; trifluoroacetate; sulphate; hydrogensulphate; methylsulphate; ethylsulphate; 1-propylsulphate; 1-butylsulphate; 1-hexylsulphate; 1-octylsulphate; phosphate; dihydrogenphosphate; hydrogenphosphate; C 1 -C 4 -dialkylphosphates; propionate; tetrachloroaluminate; Al 2 Cl 7 ⁇ ; chlorozincate; chloroferrate; bis(trifluoromethylsulphonyl)imide; bis(pentafluor
  • Preferred anions are selected from the group comprising, without making any claim as to completeness, the halides, bis(perfluoroalkylsulphonyl)amides or -imides such as bis(trifluoromethylylsulphonyl)imide, alkyltosylates and aryltosylates, perfluoroalkyltosylates, nitrate, sulphate, hydrogensulphate, alkylsulphates and arylsulphates, polyether sulphates and sulphonates, perfluoroalkylsulphates, sulphonate, alkylsulphonates and arylsulphonates, perfluorinated alkylsulphonates and arylsulphonates, alkylcarboxylates, and arylcarboxylates, perfluoroalkylcarboxylates, perchlorate, tetrachloroaluminate, saccharinate.
  • the halides
  • dicyanamide dicyanamide, thiocyanate, isothiocyanate, tetraphenylborate, tetrakis(pentafluorophenyl)borate, tetrafluoroborate, hexafluorophosphate, polyether phosphates and phosphate.
  • ionic liquids or mixtures thereof which contain a combination of a 1,3-dialkylimidazolium, 1,2,3-trialkylimidazolium, 1,3-dialkylimidazolinium and 1,2,3-trialkylimidazolinium cation with an anion selected from the group consisting of the halides, bis(trifluoromethylylsulphonyl)imide, perfluoroalkyltosylates, alkylsulphates and -sulphonates, perfluorinated alkylsulphonates and alkylsulphates, perfluoroalkylcarboxylates, perchlorate, dicyanamide, thiocyanate, isothiocyanate, tetraphenylborate, tetrakis(pentafluorophenyl)borate, tetrafluoroborate, hexafluorophosphate, acetate, glyco
  • acyclic quaternary ammonium salts such as TEGO® IL T16ES, TEGO® IL K5MS, TEGO® IL DS or TEGO® IL 2MS (products of Evonik Goldschmidt GmbH).
  • Particularly preferred ionic liquids for the purposes of the present disclosure are:
  • performance additives improves the wetting properties of preferably single-phase compositions containing ionic liquids on solid surfaces.
  • performance additives are substances which improve the wetting properties and/or the spreading behavior of ionic liquids on solid surfaces.
  • wetting refers to the covering of the surface by the liquid. Improved wetting behavior can be recognized by fewer unwetted places existing and wetting being uniform.
  • Spreading is, for the present purposes, the spontaneous wetting of the solid surface.
  • the liquid spreads spontaneously in the form of a flat disc on the surface.
  • a monomolecular film is formed and the contact angle is zero.
  • a lowering of the surface tension of the liquid is a necessary but not sufficient condition for spreading.
  • compositions of the invention serve for the lasting wetting of solid surfaces and contain at least one ionic liquid and at least one performance additive and if appropriate solvents and/or further auxiliaries or additives.
  • compositions of the invention comprise from 50 to 99.999% by weight, preferably from 80 to 99.999% by weight, in particular at least 95% by weight and particularly preferably from >98 to 99.999% by weight, of one or more ionic liquids,
  • compositions of the invention preferably consist of a single phase.
  • compositions of the invention can contain organic solvents or water and/or mixtures thereof as solvents; preference is given to no solvents or organic solvents being present.
  • Surfactants as such are used in aqueous systems or organic systems which have non-ionic character.
  • the surfactants mentioned can also positively influence the wetting properties and the spreading behavior of ionic liquids.
  • radical P is:
  • R 20 is a hydrogen, alkyl or carboxyl radical.
  • R 20 is preferably a hydrogen or methyl radical or acetyl radical.
  • the index g is from 0 to 6, the index h is from 0 to 20, the index i is from 0 to 50, where h+i ⁇ 1, the index j is from 0 to 10 and the index k is from 0 to 10.
  • the index g being from 0 to 3
  • the index h being from 5 to 80
  • the index i being from 0 to 30, with the indices j and k preferably being ⁇ 5, in particular 0.
  • polyether siloxane derivatives are those of the general formula (XVIII):
  • a and b are average values since the silicone polyether copolymers which are concomitantly used according to the invention are present in the form of generally equilibrated mixtures.
  • the radicals R1 are alkyl radicals having from 1 to 4 carbon atoms, e.g. methyl, ethyl, propyl or butyl radicals, or aryl radicals, with phenyl radicals being preferred.
  • methyl radicals are preferred, so that at least 80% of the radicals R1 are methyl radicals.
  • Particular preference is given to polysiloxanes in which all radicals R1 are methyl radicals.
  • the value of a can, on the basis of experience, be combined only in the indicated way with values of b since otherwise the increased viscosity makes handling impossible.
  • Particularly preferred silicone polyether copolymers are those of the general formula (xx)
  • Suitable polyether siloxanes are structures of the Formula (XXI)
  • the compounds of the structures indicated are present as statistical mixtures and the indices indicated therefore correspond to the arithmetic means of the mixtures.
  • compositions of the invention preferably contain one or more nonionic surfactants, particularly preferably one or more organo-modified siloxanes, particularly preferably one or more polyether siloxanes and especially polyether siloxanes of the Formula (XVIII), as performance additive.
  • nonionic surfactants particularly preferably one or more organo-modified siloxanes, particularly preferably one or more polyether siloxanes and especially polyether siloxanes of the Formula (XVIII), as performance additive.
  • the trademark proprietors are:
  • TEGO TEGOSURF AROSURF REWOQUAT VARONIC ADOGEN REWOMID VARAMID REWOCOROS REWOPAL are trademarks of Evonik Goldschmidt GmbH SURFYNOL, DYNOL, ENVIROGEM are trademarks of Air Products, Inc.
  • AGNIQUE is a trademark of Cognis TRITON is a trademark of DOW Chemical Company
  • GENAPOL is a trademark of Clariant
  • PLURONIC is a trademark of BASF
  • EMPIGEN is a trademark of Albright&Wilson
  • performance additives can be used either alone or in any mixtures with one another together with the ionic liquids. Further customary solvents, auxiliaries and additives can likewise have been or be mixed in.
  • solid surfaces are glass, metal, semiconductors, polymers, ceramic, stone and leather and fabrics or membranes comprising these materials.
  • metal surfaces are surfaces of aluminium, chromium, nickel, magnesium, titanium, vanadium, iron, copper, zinc, cobalt, gallium, germanium, zirconium, molybdenum, palladium, silver, tin, tungsten, platinum, gold, lead and alloys thereof, also with other elements such as carbon, in particular steel.
  • An example of a steel surface is a surface of S235JRG2 steel.
  • Examples of semiconductor surfaces are surfaces of silicon and titanium dioxide.
  • polymer surfaces are surfaces of natural or synthetic thermoplastics, thermosets and elastomers.
  • plastic surfaces are polyacrylates such as polymethyl methacrylate, polyacrylonitrile, polyacrylic acid, polyvinyl halides such as polyvinyl chloride, polyvinyl alcohol, polyethylene, polypropylene, polybutadiene, polyacrylonitrile, polyethers, polysulphides, polysulphones, polyether sulphone, polyketones, polyesters, polycarbonates, polystyrene, formaldehyde resins, epoxy resins, polyamides, polyureas, polyurethanes, polyimides, polyphenols, polypyrroles, polyfuran, polythiophene, polybenzimidazoles, polyamines, polyanhydrides, polytetrafluoroethylene, polyvinylidene fluoride, polylactates, polysiloxanes, polysilanes, copolymers and blends thereof and mixtures or copolymers, oligomers and block (co)polymers thereof.
  • Natural polymers are rubber, lig
  • Ceramic surfaces are surfaces of clay, kaolin, clay minerals, aluminium oxide, beryllium oxide, zirconium oxide, silicon carbide, silicon nitride, aluminium nitride, boron nitride, boron carbide.
  • membrane surfaces are particularly preferred.
  • the invention likewise provides for the use of the compositions comprising one or more ionic liquids and one or more performance additives and also further additives and/or auxiliaries, wherein the composition has a contact angle with the treated surface which is at least 100 smaller, preferably 200 smaller, particularly preferably 300 smaller and very particularly preferably 400 smaller, than that without the addition of the performance additive.
  • the invention likewise provides for the use in a method of wetting solid surfaces by ionic liquids, preferably optimized wetting by addition of the performance additive, with particular preference being given here to the wetted surface being at least 30% greater, preferably 50% greater, particularly preferably 80% greater and very particularly preferably 100% greater, than without addition of the performance additive. This is also associated with an increase in the diameter of the wetted area, which is likewise at least 50% greater than the diameter of the wetted surface without addition of the performance additive.
  • the mixing ratios of ionic liquid and performance additive are in the range from 100 000:1 to 1:10 000, preferably from 10 000:1 to 1:1, particularly preferably from 10 000:1 to 10:1, very particularly preferably from 1000:1 to 100:1 (all ratios are ratios of % by weight).
  • the mixtures can contain further solvents, in particular organic solvents and/or water.
  • organic solvents are aliphatic, cycloaliphatic, aromatic, heterocyclic, heteroaromatic substituted or unsubstituted alcohols, aldehydes, ketones, carboxylic esters, carboxamides, carboxylic anhydrides, carbonates, carbamates, nitrites, ethers, polyethers, alkanes, alkenes, halogenated hydrocarbons, thiols, thioethers, thioesters, amino acids, polyols, sulphones, sulphoxides, ureas and thioureas.
  • the proportion of the solvent in the total mixture is in the range from 99.9% to 0.01%, preferably from 50% to 0.05%, particularly preferably from 25% to 0.1% and very particularly preferably from 10% to 0.5% (all percentages are % by weight).
  • the increase in wettable area for the compositions of the invention relative to composition without at least one performance additive is in a range selected from the group consisting of about 40% to about 1500% and about 50% to about 1200%.
  • the mixtures can also be used advantageously for many other chemical-industrial processes, thus generally in the metal processing industry, for example in cooling lubricants, hardening oils, hydraulic fluid emulsions, polishing pastes, mould release agents, drawing oils, pickling agents or metal cleaners.
  • mixtures of the invention can be used in the leather, paper, printing, electroplating and photographic industries.
  • mixtures can be used in water treatment, for example in the treatment of wastewater.
  • mixtures can be used in crop protection formulations.
  • the surfactants can be used either alone or in mixtures with one another and can contain further additives and auxiliaries which can be specifically selected according to the application.
  • ionic liquid 8 g
  • IL ionic liquid
  • the sample was stirred with a spatula until it was homogeneous and 50 ⁇ l were subsequently pipetted onto a PP film.
  • the maximum spread after 5 minutes was determined.
  • the diameter (D) of the resulting circle is determined in mm. The higher the measured value, the greater the spreading and wetting and thus the effect of the performance additive according to the invention.
  • TEGO WET 505 Alkyl alkoxylate (CAS No. 303152-49-0)
  • TEGO Twin 4000 Polyether-modified polysiloxane (CAS No. 780769-22-4)
  • TEGOPREN 5878 Polyether-modified polysiloxane (CAS No. 27306-78-1)
  • TEGO STO 85 V Polyoxyethylene(20)sorbitan trioleate (CAS No. 9005-70-3)
  • the diameter of the wetted area is, in each case demonstrated by way of example, more than 50% greater than the diameter of the wetted area without the performance additive.
  • the wetted area itself has increased to an even greater extent in relative terms.
  • the contact angle to polypropylene film (PP film) of the ionic liquids measured changes significantly after the addition of the performance additives.
  • the contact angle is a measure of the spreading properties of the performance additives.
  • the spreading capability is greater the lower the contact angle (higher range value in the following table).
  • mixtures of an ionic liquid and the performance additives according to the invention were applied by means of a doctor blade to a glass plate and the wetting properties and the film formation of the products was checked.
  • a glass plate was prepared by precleaning it using water and cleaners, subsequently rinsed under running water and degreased by means of ethanol. This glass plate was placed on a horizontal substrate and the box doctor blade was placed at one end of the glass plate. Part of the liquid was introduced into the box which was drawn in one stroke over the glass plate.
  • the applied layer should be no more than 50 ⁇ m. The layer formed was assessed immediately afterwards. Here, the number of craters was counted. The results show that the number of craters was significantly reduced by addition of the performance additive compared to the blank. The addition of a performance additive thus improves the wetting properties of the ionic liquids.

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