EP2473574A2 - Liquides ioniques dotés d'une viscosité améliorée - Google Patents

Liquides ioniques dotés d'une viscosité améliorée

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Publication number
EP2473574A2
EP2473574A2 EP10747462A EP10747462A EP2473574A2 EP 2473574 A2 EP2473574 A2 EP 2473574A2 EP 10747462 A EP10747462 A EP 10747462A EP 10747462 A EP10747462 A EP 10747462A EP 2473574 A2 EP2473574 A2 EP 2473574A2
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EP
European Patent Office
Prior art keywords
compound
ionic liquid
groups
weight
group
Prior art date
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EP10747462A
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German (de)
English (en)
Inventor
Klemens Massonne
Aurelie Alemany
Dirk Gerhard
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BASF SE
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BASF SE
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Priority to EP10747462A priority Critical patent/EP2473574A2/fr
Publication of EP2473574A2 publication Critical patent/EP2473574A2/fr
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
    • C09K5/02—Materials undergoing a change of physical state when used
    • C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
    • C09K5/047—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for absorption-type refrigeration systems
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    • 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
    • C10M171/02—Specified values of viscosity or viscosity index
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
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    • 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
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084—Acrylate; Methacrylate
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    • 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
    • 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
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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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
    • 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
    • C10M2215/08—Amides
    • 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
    • C10M2215/22—Heterocyclic nitrogen compounds
    • 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
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/223—Five-membered rings containing nitrogen and carbon only
    • C10M2215/224—Imidazoles
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/028—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
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    • 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
    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2221/02—Macromolecular compounds obtained by reactions of monomers involving only carbon-to-carbon unsaturated bonds
    • 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
    • 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
    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/09—Characteristics associated with water
    • C10N2020/091—Water solubility
    • 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
    • C10N2030/02—Pour-point; Viscosity index
    • 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
    • C10N2030/70—Soluble oils
    • 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
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • 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
    • C10N2040/34—Lubricating-sealants

Definitions

  • the present invention relates to a method for adjusting the viscosity of a salt having a melting point of less than 100 ° C at atmospheric pressure (abbreviated to ionic liquid), which is characterized in that a compound is added to the ionic liquid, which has a content of at least 0.1 Mol functional groups / 100g compound and the functional groups are selected from
  • Acid groups or their salts, acid amide, amino, ammonium and hydroxyl groups are acids or their salts, acid amide, amino, ammonium and hydroxyl groups.
  • Ionic liquids are of great interest for a wide variety of technical applications.
  • applications as a solvent or electrolyte are applications as a lubricant, hydraulic fluid or operating fluid, as a heat carrier, for heat transfer or as a sealing or Absperrroughkeit into consideration.
  • ionic liquids as absorbents in heat pumps, i. as operating fluid, z. B. from WO 2005/1 13702 known.
  • ionic liquids as a hydraulic fluid, lubricant, operating fluid, stop-off or sealing fluid are e.g. also listed in WO 2006/087333.
  • suitable ionic liquids must meet a variety of required properties. An essential feature in all these applications is the viscosity. Often many, but not all, of the required properties are met by a selected ionic liquid. The remaining, unfulfilled properties must, if possible, be adjusted accordingly.
  • the viscosity of the otherwise suitable ionic liquid may not be high enough.
  • the subject of the process according to the invention is the adjustment of the viscosity of an ionic liquid by adding a compound.
  • the ionic liquid is a salt with a melting point of less than 100 ° C at 1 bar.
  • the ionic liquid has a melting point less than 70 ° C and more preferably less than 30 ° C.
  • the ionic liquid is liquid under normal conditions (1 bar, 21 ° C).
  • the ionic liquid is a salt and therefore consists of at least one cation and at least one anion.
  • Preferred ionic liquids contain at least one organic compound as cation, very particularly preferably they contain only organic compounds as cations.
  • Suitable organic cations are, in particular, organic compounds containing heteroatoms, such as nitrogen, sulfur, oxygen or phosphorus, particular preference being given to organic compounds having a cationic group selected from an ammonium group, an oxonium group, a sulfonium group or a phosphonium group.
  • the ionic liquids are ammonium cation salts, which includes non-aromatic compounds having a localized positive charge on the nitrogen atom, e.g. Compounds with terminated nitrogen (quaternary ammonium compounds) or compounds with three nitrogen, wherein a bond is a double bond, or aromatic compounds with delocalized positive charge and at least one, preferably one or two nitrogen atoms in the ring system are understood.
  • organic cations are quaternary ammonium cations having preferably three or four aliphatic substituents, particularly preferably C 1 - to C 12 -alkyl groups, on the nitrogen atom.
  • Organic cations which contain a heterocyclic ring system having one or two nitrogen atoms as part of the ring system are also particularly preferred.
  • Suitable compounds are monocyclic, bicyclic, aromatic or non-aromatic ring systems. Examples include bicyclic systems, as described in WO 2008/043837.
  • bicyclic systems of WO 2008/043837 are diazabicyclo derivatives, preferably of a 7- and a 6-ring, which contain an amidinium group; in particular the 1,8-diazabicyclo- (5.4.0) undec-7-enium cation may be mentioned.
  • Very particularly preferred organic cations comprise a five- or six-membered heterocyclic ring system having one or two nitrogen atoms as part of the ring system.
  • Suitable cations are e.g. Pyridinium cations, pyridazinium cations, pyrimidinium cations, pyrazinium cations, imidazolium cations, pyrazolium cations
  • Atoms preferably a hydrocarbon group, in particular a C1 to C16 alkyl group, in particular a C1 to C10, particularly preferably a C1 to C4 alkyl groups substituted.
  • the carbon atoms of the ring system can also be substituted by organic groups having generally not more than 20 C atoms, preferably a hydrocarbon group, in particular a C1 to C16 alkyl group, in particular a C1 to C10, particularly preferably a C1 to C4 alkyl groups.
  • Particularly preferred ammonium cations are quaternary ammonium cations, imidazolium cations, pyrimidinium cations and pyrazolium cations.
  • the anion may be an organic or inorganic anion.
  • Suitable anions are, in particular, those from the group of halides and halogen-containing compounds of the formulas:
  • R a R P0 2 " , R a HP0 2 -, R a R b PO " , R a HPO " the group of the carboxylates of the general formulas:
  • R b is -O 2 S ' SO 2 -R c
  • M is a metal and Hal is fluorine, chlorine, bromine or iodine, r and t are integer positive numbers and indicate the stoichiometry of the complex and s is an integer positive number indicating the charge of the complex; the group of sulfides, hydrogen sulfides, polysulfides, hydrogen polysulfides and thiolates of the general formulas:
  • v is a whole positive number from 2 to 10; and the group of complex metal ions such as Fe (CN) 6 3 ", Fe (CN) 6 4" MnCv, Fe (CO) 4 ⁇
  • R a , R b , R c and R d are each independently
  • C 3 -C 12 -cycloalkyl and their aryl, heteroaryl, cycloalkyl, halogen, hydroxy, amino, carboxy, formyl, -O-, -CO- or -CO-O-substituted components, such as cyclopentyl , 2-methyl-1-cyclopentyl, 3-methyl-1-cyclopentyl, cyclohexyl, 2-methyl-1-cyclohexyl, 3-methyl-1-cyclohexyl, 4-methyl-1-cyclohexyl or C q F2 ( q-a ) - (ib) H2a-b with q ⁇ 30, 0 ⁇ a ⁇ q and b 0 or 1;
  • C 2 -C 30 -alkenyl and their aryl-, heteroaryl-, cycloalkyl-, halogen-, hydroxy-, amino-, carboxy-, formyl-, -O-, -CO- or -CO-O-substituted components, such as, for example 2 -Propenyl, 3-butenyl, cis-2-butenyl, trans-2-butenyl or Cq F2 ( q -a) - (ib) H2a-b with q ⁇ 30, 0 ⁇ a ⁇ q and b 0 or 1 ;
  • Aryl or heteroaryl having 2 to 30 carbon atoms and their alkyl, aryl, heteroaryl, cycloalkyl, halogen, hydroxy, amino, carboxy, formyl, -O-, -CO- or -CO-O- substituted components such as phenyl, 2-methylphenyl (2-tolyl), 3-methylphenyl (3-tolyl), 4-methylphenyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethyl - phenyl, 2,3-dimethyl-phenyl, 2,4-dimethyl-phenyl, 2,5-dimethyl-phenyl, 2,6-dimethyl-phenyl, 3,4-dimethyl-phenyl, 3,5-dimethyl-phenyl , 4-phenyl-phenyl, 1-naphthyl, 2-naphthyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-
  • two radicals are an unsaturated, saturated or aromatic, optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and / or heterocycles and optionally substituted by one or more oxygen and / or sulfur atoms and / or one or more substituted or unsubstituted imino groups interrupted ring.
  • R a , R b , R c and R d are preferably each independently a hydrogen atom or a C 1 to C 12 alkyl group.
  • Ra, Rb, Rc and Rd are preferably each independently a hydrogen atom or a C1 to C12 alkyl group.
  • Anions are particularly preferably those from the group of alkyl sulfates
  • R a is a C 1 to C 12 alkyl group, preferably a C 1 -C 6 alkyl group, the alkyl sulfonates
  • R a is a C 1 to C 12 alkyl group, preferably a C 1 -C 6 alkyl group, halides, in particular chloride and bromide and the pseudohalides, such as thiocyanate, dicyanamide, the carboxylates R a COO-;
  • R a is a C 1 to C 20 alkyl group, preferably a C 1 -C 8 alkyl group, in particular acetate, the phosphates,
  • dialkyl phosphates of the formula R a R b P0 4 - wherein R a and R b independently of one another represent a C 1 to C 6 alkyl group; in particular, R a and R b are the same alkyl group, which may be mentioned dimethyl phosphate and diethyl phosphate and the phosphonates, especially the Monoalkylphosphonklareester of the formula R a R b P03 " , wherein R a and R b independently of one another represent a C 1 to C 6 alkyl group.
  • Chloride bromide, hydrogen sulfate, tetrachloroaluminate, thiocyanate, dicyanamide, methylsulfate, ethylsulfate, methanesulfonate, formate, acetate, dimethyl phosphate,
  • Particularly preferred ionic liquids consist exclusively of an organic cation having one of the above anions.
  • the molar weight of the ionic liquids is preferably less than 2000 g / mol, more preferably less than 1500 g / mol, more preferably less than 1000 g / mol, and most preferably less than 750 g / mol; in a particular embodiment, the molecular weight is between 100 and 750 or between 100 and 500 g / mol.
  • they are imidazolium compounds, particularly preferably imidazolium compounds of the formula
  • R 1 and R 3 independently of one another represent an organic radical having 1 to 20 C atoms
  • R 2, R 4, and R 5 independently of one another represent an H atom or an organic radical having 1 to 20 C atoms,
  • R 1 and R 3 are preferably independently an organic group containing 1 to 10 C atoms. Particularly preferred is a coal hydrogen group which has no further heteroatoms, for example a saturated or unsaturated aliphatic group, an aromatic group or a hydrocarbon group which has both aromatic and aliphatic constituents. Very particular preference is given to a C1 to C10 alkyl group, a C1 to C10 alkenyl group, for example an allyl group, a phenyl group, a benzyl group. In particular, it is a C1 to C4 alkyl group, for example a methyl group, ethyl group, propyl group, i-propyl group or n-butyl group.
  • R 2, R 4 and R 5 are preferably independently of one another an H atom or an organic group which contains 1 to 10 C atoms.
  • R 2, R 4 and R 5 are an H atom or a hydrocarbon group which has no further heteroatoms, e.g. an aliphatic group, an aromatic group or a hydrocarbon group having both aromatic and aliphatic components.
  • Very particular preference is given to an H atom or a C1 to C10 alkyl group, a phenyl group or a benzyl group.
  • it is an H atom or a C1 to C4 alkyl group, e.g. a methyl group, ethyl group, propyl group, i-propyl group or n-butyl group.
  • the variable n is preferably 1.
  • Suitable anions X and preferred anions X are those listed above.
  • ionic liquids 1, 4-dimethyl-3-ethylimidazolium, 3-butylimidazolium, 1, 4-dimethyl-3-octylimidazolium, 1, 4,5-trimethylimidazolium, 1, 3,4,5-tetramethylimidazolium, 1, 4,5-trimethyl- 3-ethyl imidazolium, 1, 4,5-trimethyl-3-butylimidazolium or 1, 4,5-trimethyl-3-octylimidazolium; and as an anion, the above anions and preferred anions.
  • ionic liquids are:
  • the viscosity of the ionic liquid is adjusted by adding a compound.
  • the compound has a content of at least 0.1 mol, preferably 0.2 mol and more preferably of at least 0.5 mol of functional groups per 100 g of the compound, where the functional groups are selected from acid groups or their salts, acid amide, amino , Ammonium and hydroxyl groups.
  • the upper limit of the content of these functional groups is the theoretically maximum possible content of such functional groups; in general, the content is at most 2.5 moles, which z. B. in the diglycerol almost achieved, in particular a maximum of 2.1 mol, which z. B. can be achieved in the triglycerol and maximally 1, 4 mol, which are achieved in the polyacrylic acid.
  • Such a high content of functional groups is generally not necessary for the advantages of the invention, very good results are achieved with a content of functional groups of 0.1 to 1.5 mol / 100 g of compound, in particular from 0.2 to 1 , 1 mol / 100g of compound, and more preferably from 0.5 to 1.1 mol / 100g of compound.
  • the functional groups of the compound may be exclusively acid groups or exclusively acid amide groups or exclusively amino groups or exclusively ammonium groups or exclusively hydroxy groups.
  • the compound may also contain several of the said functional groups, for. B. compounds are suitable and easy to prepare, containing both acid groups and acid amide groups.
  • the salts of these acid groups may be salts with any cations, e.g. inorganic cations, such as metal cations of the 1. or 2nd main group or the ammonium cation Nh.
  • only a part of the acid groups may be present as a salt.
  • For polybasic acids i. Acids with more than one acid proton, optionally only part of the protons may be replaced by a cation.
  • the acid groups preferably sulfonic acid groups and carboxylic acid groups, particularly preferably carboxylic acid groups, can easily be converted completely or partially into salt groups, eg. B. by addition of a base as a neutralizing agent, they are then present in whole or in part as a salt of the neutralizing agent.
  • a neutralizing agent may be mentioned by way of example NaOH.
  • acid amide groups come z.
  • the amides of the above acid groups into consideration, preferably the sulfonic acid amides and carboxylic acid amides.
  • the carboxylic acid amides may be cyclic or non-cyclic amides.
  • the cyclic amides are referred to as lactams.
  • Amino groups may be primary, secondary or tertiary amino groups. Amino groups may also be part of heterocyclic ring systems, such as. In imidazole.
  • ammonium groups are meant groups having at least one nitrogen atom and one positive charge. It may be
  • hydroxyl groups may be bonded to aromatic or aliphatic groups of molecules, preferred are hydroxyl groups which are bonded to an aliphatic carbon atom. Any compounds satisfying the above conditions are contemplated.
  • the compound may be solid or liquid at room temperature (21 ° C).
  • Preferred compounds are homogeneously miscible with water at 21 ° C. (1 bar) or have a solubility of at least 20 g, preferably at least 30 g of compound in 100 g of water at 21 ° C. (1 bar) in water.
  • the compound preferably contains a total of at least 4, more preferably at least 5, functional groups per molecule, which may be a single or combinations of said functional groups; for oligomeric or polymeric compounds this is an average.
  • the compound contains only one kind of said functional groups, e.g. B. only amino groups, only carboxylic acid groups or wholly or partially their salts (carboxylate groups) or only Sulfonklaregrup- pen or wholly or partially their salts (sulfonate) or only Hydroxylgrupppen.
  • said functional groups e.g. B. only amino groups, only carboxylic acid groups or wholly or partially their salts (carboxylate groups) or only Sulfonklagrup- pen or wholly or partially their salts (sulfonate) or only Hydroxylgrupppen.
  • an oligomeric or polymeric compound e.g. is obtainable by (poly) condensation, (poly) adduct formation or free-radical polymerization from starting compounds.
  • the compound can therefore have a molecular weight of z. B. 100g / mol to 250,000 g / mol.
  • Preferred compounds have a molecular weight of 200 to 100,000 g / mol, particularly preferred compounds have a molecular weight of 300 to 50,000 g / mol.
  • Mg the actual molecular weight
  • Mn the number average molecular weight
  • Compounds with carboxylic acid groups or carboxylate groups are, for.
  • Polystyrenesulfonic acid, or polystyrenesulfonates, or polymers containing styrenesulfonic acid or styrenesulfonates may be mentioned as compounds with sulfonic acid groups or sulfonate groups. Mention may also be made of copolymers which contain AMPS (Lupasol® PR-140) or its salts. AMPS is an unsaturated acid amide with a sulfonic acid or sulfonate group.
  • Poly (meth) acrylic acid or (meth) acrylic acid copolymers can be obtained by free-radical polymerization, in particular by solution or bulk polymerization, of acrylic acid or methacrylic acid and in the case of the copolymers of further free-radically polymerizable monomers.
  • Suitable (meth) acrylic acid copolymers are those with any desired comonomers, e.g. one or more comonomers selected from acrylates, vinyl esters, vinyl ethers, vinyl aromatics such as styrene, olefins such as ethylene or propylene, or vinyl halides.
  • the comonomers may contain functional groups, e.g. As the above-mentioned as mandatory acid groups, acid amide groups or hydroxyl groups or other functional groups.
  • poly (meth) acrylic acid or (meth) acrylic acid copolymers of acrylic acid or methacrylic acid with maleic acid or maleic anhydride Preference is given to poly (meth) acrylic acid or (meth) acrylic acid copolymers of acrylic acid or methacrylic acid with maleic acid or maleic anhydride.
  • Poly (meth) acrylic acid and (meth) acrylic acid copolymers are e.g. B. offered by BASF under the brand Sokalan®.
  • Compounds with Carbonklareamid phenomenon are z.
  • Compounds having cyclic amide groups are, in particular, polyvinylpyrrolidone and vinylpyrrolidone copolymers which preferably contain at least 30% by weight, in particular at least 50% by weight, of vinylpyrrolidone, for example copolymers of vinylpyrrolidone and vinylimidazole (Sokalan® HP56)
  • the temperature dependence The viscosity of mixtures of ionic liquid with these polymers is particularly low. Such mixtures are therefore particularly suitable for the applications below, for. B. as hydraulic fluid.
  • Compounds with amino groups are for.
  • Vinylamine copolymers which at least 30 wt.%, In particular at least 50 wt.% Viny- consist of lamin.
  • Vinylamine copolymers are especially those with vinylformamide.
  • Such copolymers may, for. B. be prepared by partial hydrolysis of polyvinylformamide.
  • a suitable such compound is in particular polyvinylimidazole or a vinylimidazole copolymer which consists of more than 30% by weight, in particular at least 50% by weight, of vinylimidazole.
  • Compounds with ammonium groups can be obtained in a simple manner by protonation of compounds containing amino groups, preferably the compounds provided. The protonation can be done by adjusting the necessary pH.
  • Compounds with hydroxyl groups are for.
  • polyvinyl alcohol or vinyl alcohol copolymers which are preferably at least 30 wt.%, In particular at least 50 wt.% Of vinyl alcohol, and polyglycerols.
  • polyglycerols are particularly preferred.
  • Polyglycerols (English polyglycerol) are condensation products of glycerol.
  • Diglycerol is the condensation product (with dehydration) of two glycerol units and accordingly contains an ether group and 4 hydroxyl groups.
  • triglycerin, tetraglycerol, pentaglycerol, etc. are the condensation products of a corresponding number of glycerol units. Since the condensation proceeds with the participation of different hydroxyl groups, a uniform degree of condensation is generally also isomeric mixtures.
  • polyglycerols (English polyglycerol) having a number average molecular weight of 250 to 1000 g / mol are particularly preferred.
  • ionic liquid shall in the following also be understood to mean a mixture of ionic liquids
  • compound shall in the following also mean a mixture of compounds.
  • the compound is preferably added to the ionic liquid in an amount of 0.1 to 30 parts by weight per 100 parts by weight, more preferably in amounts of 1 to 20 parts by weight, and most preferably in amounts of 2 to 15 parts by weight 100 wt. Part added to ionic liquid.
  • the addition increases the viscosity of the ionic liquid.
  • the compound can be added to the pure ionic liquid, but it can also be added to mixtures which contain other substances in addition to the ionic liquid; it may be e.g. to act substances such as solvents or substances dissolved in the ionic liquid. Such mixtures may, for. B. arise during use of ionic liquids. It is therefore also an advantage of the process according to the invention that the viscosity can be increased or adjusted during the use of the ionic liquid (see below) by adding the compound.
  • the ionic liquid another nonionic solvent. It is preferably a solvent which is homogeneously miscible with the ionic liquid at 21 ° C (1 bar) and at 21 ° C, 1 bar has a dielectric constant greater than 7.5.
  • Preferred solvents are polar aliphatic solvents having hydroxyl groups or ether groups.
  • the amount of nonionic solvent, in particular water or methanol, is preferably at least 1 part by weight, in particular at least 5 parts by weight, more preferably at least 10 parts by weight and most preferably at least 20 parts by weight per 100 parts by weight ionic Liquid.
  • the non-ionic solvent may preferably divide the ionic liquid in amounts of from 1 to 150 parts by weight, more preferably from 5 to 100% by weight, and very preferably especially preferably from 10 to 80 parts by weight, in particular from 20 to 60 parts by weight, per 100 parts by weight of ionic liquid are added.
  • the addition of the nonionic solvent reduces the temperature dependence of the viscosity, which is important for many applications with a broad temperature range.
  • compositions containing an ionic liquid and the above compound By adding the compound to the ionic liquid according to the present invention, there are available compositions containing an ionic liquid and the above compound. Also obtainable are compositions containing an ionic liquid, the above compound and the above solvent.
  • compositions may contain more than 70% by weight, in particular more than 90% by weight and more preferably more than 95% by weight, more than 98% by weight or exclusively (100% by weight) of the ionic Liquid, the compound and ggb.
  • the solvent exist. This is especially the case before their use; During use, other substances may be included in the composition due to the nature of the use.
  • the viscosity of the composition when it is more than 90% by weight of the ionic liquid, the compound and the solvent, is preferably 10 mPa * s to 2,500 mPa * s at 20 ° C.
  • the viscosity stated is the dynamic viscosity.
  • composition of the invention is suitable for a variety of uses.
  • Called z. B. uses as a lubricant, hydraulic fluid, operating fluid in devices, eg. B. as an absorbent in thermodynamic cycle processes, which are based on absorption and desorption, as heat transfer, for heat transfer or as a sealing or Absperrroughkeit.
  • EMIM-MeSOs EMIM-methylsulfonate
  • EMIM-EtS0 4 EMIM ethylsulfate
  • EMIM acetate EMIM OAc
  • EMIM thiocyanate EMIM SCN
  • Tris-2 (hydroxyethyl) -methylammonium-methylsulfate (FS01) As polymeric compounds were used:
  • Sokalan® PA 80 S an acrylic acid-maleic acid copolymer from BASF
  • Sokalan® PA 1 10 S an acrylic acid-maleic acid copolymer from BASF Sokalan® HP56K from BASF, a copolymer of vinylpyrrolidone and vinylimidazole
  • K 60 Polyvinylpyrrolidone K 60 (K 60 is the Fikentscher K value, which is a measure of the molecular weight).
  • Polyglycerol-4 a polyglycerol from Solvay Chemicals, which consists predominantly of linear tetraglycerol and contains low levels of diglycerol and triglycerol.
  • the starting materials were mixed in the amounts indicated in the table, wherein in each case 100 parts by weight of the ionic liquid, the stated parts by weight of compound were added. Optionally, this mixture was added to water. The viscosity of the mixtures was determined at different temperatures.
  • Table 1 shows the composition of the mixtures and the viscosities.
  • the viscosity index of mixtures according to DIN ISO 2909 was determined.
  • the viscosity index is determined from viscosities at 40 ° C. and 100 ° C. according to the calculation specified in DIN ISO 2909. The higher the viscosity index, the lower the temperature dependence of the viscosity.
  • Sok : Sokalan PA 80 S
  • Blend in the 1st column refers only to EMIM methyl sulfonate and Sokalan HP56K and indicates the weight fraction of EMIM methyl sulfonate, the difference to 100 being the weight fraction of Sokalan HP56K.
  • Water content in the 2nd column indicates the additionally contained parts by weight of water per 100 parts by weight of the mixture of the 1st column.

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Abstract

L'invention concerne un procédé de réglage de la viscosité d'un sel ayant un point de fusion inférieur à 100°C pour une pression normale (ci-après dénommé liquide ionique), caractérisé en ce que l'on ajoute au liquide ionique un composé qui a une teneur d'au moins 0,1 mole de groupes fonctionnels/100g de composé et les groupes fonctionnels sont sélectionnés parmi les groupes acide, amide d'acide, amino, ammonium et hydroxyle.
EP10747462A 2009-09-03 2010-08-31 Liquides ioniques dotés d'une viscosité améliorée Withdrawn EP2473574A2 (fr)

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EP09169389 2009-09-03
PCT/EP2010/062663 WO2011026822A2 (fr) 2009-09-03 2010-08-31 Liquides ioniques dotés d'une viscosité améliorée
EP10747462A EP2473574A2 (fr) 2009-09-03 2010-08-31 Liquides ioniques dotés d'une viscosité améliorée

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WO2012016835A2 (fr) * 2010-07-26 2012-02-09 Basf Se Liquides ioniques présentant une certaine teneur en polymères ioniques
DE102010034758A1 (de) * 2010-08-19 2012-02-23 Schaeffler Technologies Gmbh & Co. Kg Schmiermittelzusammensetzung, Verfahren zu deren Herstellung, Verwendung in einem Wälzlager und Wälzlager mit diesem
SE535675C2 (sv) * 2011-03-22 2012-11-06 Högprestandasmörjmedel och tillsatser till smörjmedel för järnhaltiga och icke järnhaltiga material
EP2530138A1 (fr) * 2011-06-03 2012-12-05 Carl Bechem Gmbh Lubrifiant doté d'une viscosité à résistance
MX359374B (es) * 2013-10-22 2018-09-13 Mexicano Inst Petrol Aplicacion de una composicion quimica para la reduccion de la viscosidad de petroleos crudos pesados y extrapesados.
JP6374708B2 (ja) * 2014-05-29 2018-08-15 デクセリアルズ株式会社 イオン液体、潤滑剤及び磁気記録媒体
JP6294158B2 (ja) * 2014-05-29 2018-03-14 デクセリアルズ株式会社 イオン液体、潤滑剤及び磁気記録媒体
JP6729453B2 (ja) * 2017-03-07 2020-07-22 株式会社デンソー 熱媒体用基材、並びにそれを用いた熱輸送システムおよびヒートポンプシステム

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DE102004024967A1 (de) 2004-05-21 2005-12-08 Basf Ag Neue Absorptionsmedien für Absorptionswärmepumpen, Absorptionskältemaschinen und Wärmetransformatoren
JP4618630B2 (ja) * 2004-05-26 2011-01-26 協同油脂株式会社 潤滑剤組成物
DE102005007100A1 (de) 2005-02-16 2006-08-17 Solvent Innovation Gmbh Prozess- bzw. Arbeitsmaschine mit ionischer Flüssigkeit als Betriebsflüssigkeit
EP2074255B1 (fr) * 2006-10-13 2016-12-14 Basf Se Liquides ioniques servant à solubiliser des polymères
MX2009013879A (es) * 2007-06-20 2010-01-27 Klueber Lubrication Composicion de grasa lubricante.

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