EP1171552B1 - Hydraulic fluids, containing cyclic carboxylic acid derivatives - Google Patents

Hydraulic fluids, containing cyclic carboxylic acid derivatives Download PDF

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Publication number
EP1171552B1
EP1171552B1 EP00922626A EP00922626A EP1171552B1 EP 1171552 B1 EP1171552 B1 EP 1171552B1 EP 00922626 A EP00922626 A EP 00922626A EP 00922626 A EP00922626 A EP 00922626A EP 1171552 B1 EP1171552 B1 EP 1171552B1
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EP
European Patent Office
Prior art keywords
carboxylic acid
acid derivatives
cyclic carboxylic
group
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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EP00922626A
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German (de)
French (fr)
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EP1171552A1 (en
Inventor
Bayram Aydin
Uwe Fidorra
Arthur Höhn
Ladislaus Meszaros
Jan Nouwen
Knut Oppenländer
Michael Roida
Michael Stösser
Bernd Wenderoth
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BASF SE
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BASF SE
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    • 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/24—Aldehydes; Ketones
    • 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/16—Ethers
    • C10M129/20—Cyclic ethers having 4 or more ring atoms, e.g. furans, dioxolanes
    • C—CHEMISTRY; METALLURGY
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    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
    • C10M107/30—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M107/32—Condensation polymers of aldehydes or ketones; Polyesters; Polyethers
    • C10M107/34—Polyoxyalkylenes
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    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/52—Lubricating compositions characterised by the base-material being a macromolecular compound containing boron
    • C—CHEMISTRY; METALLURGY
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    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/04—Hydroxy compounds
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    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
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    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C10M2207/044—Cyclic ethers having four or more ring atoms, e.g. furans, dioxolanes
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M2209/1033—Polyethers, i.e. containing di- or higher polyoxyalkylene groups used as base material
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    • C10M2215/226—Morpholines
    • 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
    • C10M2215/30—Heterocyclic 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/061—Esters derived from boron
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/003—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions used as base material
    • 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

Definitions

  • FR-A 2 209 830 (corresponds to DE-B 2 260 701) discloses the Use of cyclic carboxylic acid derivatives in the form of N-alkylpyrrolidones in hydraulic fluids in an amount of 20 to 60 wt .-% to reduce wear and improve the lubricating properties.
  • Hydraulic fluids and especially brake fluids for motor vehicles are subject with regard to their chemical and physical properties very high requirements.
  • brake fluids from the U.S. Department of Transportation in the Federal Motor Vehicle Safety Standard FMVSS no. 116 and that of the Society of Automotive Engineers published standard SAE J 1704 are said to be modern Brake fluids on the one hand have high dry boiling points (Reflux boiling points, dry [Equilibrium reflux boiling point, "ERBP”]) and high wet boiling points (reflux points, moist ["wet ERBP”]), but also a viscosity have, which are within a wide temperature range little changes. There are also further requirements from the automotive industry after a low Low temperature viscosity in the presence of water.
  • cyclic carboxylic acid derivatives of the general formula I are, in particular, cyclic carboxamides (lactams) and cyclic carboxylic acid esters (lactones), which can serve as precursors in the preparation of the first-mentioned lactams.
  • lactones cyclic carboxylic acid esters
  • Five- and six-membered ring systems can be used as particularly preferred ring sizes.
  • NC 1 to C 20 alkyl pyrrolidones-2 are particularly preferred ring sizes.
  • the ring member X preferably represents a grouping of the formula NR 1 .
  • the radical R 1 denotes, for example, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, iso-pentyl, sec-pentyl , tert-pentyl, neo-pentyl, n-hexyl, cyclohexyl, phenyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, iso-nonyl, n-decyl, iso-decyl, n-undecyl, n-dodecyl, n-tridecyl, iso-tridecyl, n-tetradecyl, n-hexydecyl, n-octa
  • the radical R 1 preferably denotes hydrogen or a linear or branched C 1 -C 6 -alkyl group, which can additionally be interrupted by up to 3 non-adjacent oxygen atoms and / or can carry up to 2 hydroxyl groups, or a cyclohexyl or phenyl group ,
  • R 1 can serve as examples of R 2 and R 3 .
  • R 2 and R 3 are preferably hydrogen or methyl groups, especially hydrogen.
  • n is preferably 2, 3 or 4; this would result Ring sizes from four to six-membered rings.
  • the cyclic carboxylic acid derivatives I are known substances, which are commercially available or according to common manufacturing methods can be synthesized.
  • the brake fluids contain for motor vehicles 0.01 to 10 wt .-% of one or more of the described cyclic carboxylic acid derivatives I. Both for hydraulic Liquids as well as brake fluids for motor vehicles are preferred contents of the compounds I 0.5 to 10% by weight, based on the total mass of the hydraulic fluid or brake fluid.
  • the presence of the compounds I ensures in an excellent manner that the hydraulic fluid or brake fluid for Motor vehicles meet the requirements mentioned above and in addition to those for brake fluids from the US Department of Transportation in the Federal Motor Vehicle Safety Standard FMVSS no. 116 specified requirements of the specifications DOT 5 and DOT 5.1 for silicone-free brake fluids, also the tightened ones Requirements from among the automotive industry a low low temperature viscosity in the presence of water clearly exceeds.
  • the compounds I can therefore be used in hydraulic fluids or brake fluids for motor vehicles the viscosity, in particular the Low temperature viscosity in the presence of water, to decrease d. H. set to a lower level.
  • Suitable polyglycol ethers are especially ethylene glycol monoalkyl ethers with up to 6 ethylene oxide units and with up to 4 Carbon atoms in the alkyl radical. There are also ethylene glycol or Propylene glycol dialkyl ether with up to 6 alkylene oxide units and each with up to 4 carbon atoms in the alkyl radicals into consideration.
  • Suitable boric acid esters of those mentioned or of other polyglycol ethers are described in particular in documents EP-B 013 925 (cyclic Bis-boric acid ester), DE-C 28 04 535 (nitrogen-containing boric acid ester), DE-A 24 38 038 (boric acid-alkylene glycol monoalkyl ether ester) and DE-B 17 68 933 (tris-alkoxyalkyl borate) described.
  • the brake fluids according to the invention for motor vehicles as the main component also those based on carboxylic acid esters, Contain mineral oils or silicone oils.
  • the brake fluids used for motor vehicles according to the invention contained in a further preferred embodiment in addition to the compounds I further 0.1 to 50 wt .-%, in particular 1 to 40 wt .-%, especially 5 to 30 wt .-%, each based on the total mass of the brake fluid, one or more polyglycols.
  • Suitable polyglycols are above all higher-boiling reaction products of ethylene oxide and / or propylene oxide and / or butylene oxide with water or diols, in particular corresponding reaction products of mixtures of ethylene oxide and propylene oxide with water are used.
  • the number of alkylene oxide units in such polyglycols is usually 2 to 10.
  • the effect of these high-boiling polyglycols is one Lubricant, which essentially indicates an improvement in the Temperature-viscosity behavior is attributable.
  • the polyglycols give the thin polyglycol ethers at high Temperatures sufficient viscosity and thus ensure sufficient Lubrication. Sufficient lubrication is therefore in the components of the motor vehicle braking system necessary because there Glide rubber or elastomers on metal as wear-free as possible have to.
  • the brake fluids used for motor vehicles according to the invention contained in a further preferred embodiment in addition to the compounds I further 0.01 to 10 wt .-%, in particular 0.02 to 6 wt .-%, especially 0.05 to 4 wt .-%, each based on the total mass of the brake fluid, one or more Corrosion inhibitors.
  • Corrosion inhibitors in brake fluids have the task the destruction of metallic materials caused by corrosion to prevent.
  • corrosion inhibitors especially alkali metal salts of phosphoric acid and phosphorous Acid, fatty acids such as caprylic, lauric, palmitic, stearic or Oleic acid and its alkali metal salts, esters of phosphoric acid and the phosphorous acid such as ethyl phosphate, dimethyl phosphate, Isopropyl phosphate, diisopropyl phosphate, butyl phosphite or dimethyl phosphite, optionally ethoxylated mono- and dialkylamines and their salts with mineral and fatty acids, e.g.
  • butylamine Hexylamine, octylamine, isononylamine, oleylamine, dipropylamine, Diisopropylamine or dibutylamine, optionally ethoxylated Alkanolamines, e.g. Mono-, di- or triethanolamine, N, N'-din-butylaminoethanol or 1,1'-iminodipropan-2-ol, cyclohexylamine, Triazoles such as benzo- or tolutriazole and nitroaromatics, e.g. 3-nitrobenzaldehyde.
  • Alkanolamines e.g. Mono-, di- or triethanolamine, N, N'-din-butylaminoethanol or 1,1'-iminodipropan-2-ol, cyclohexylamine, Triazoles such as benzo- or tolutriazole and nitroaromatics, e.g. 3-nitrobenzaldehy
  • Brake fluids for motor vehicles can contain common antioxidants, e.g. those based on phenol, and conventional defoamers his.
  • the motor vehicle brake fluid BF 1 used without connections I had the following composition: 75% by weight Methyltriglycol-borate, 22% by weight a mixture of methyldi, methyltri and methyltetraglycol, ⁇ 3% by weight a mixture of N, N'-di-n-butylaminoethanol, 1,1'-iminodipropan-2-ol, tolutriazole and 3-nitrobenzaldehyde ⁇ 0.5% by weight Bisphenol A
  • BF 1 starting 5 wt .-% methyl triglycol against 5 wt .-% of cyclic carboxylic acid derivatives used according to the invention.

Abstract

Hydraulic fluids, in particular brake fluids for motor vehicles, comprising from 0.01 to 50 wt % of one or more cyclic carboxylates, or cyclic carboxamides, which can carry a linear or branched C1-bis C20 alkyl group on the nitrogen atom.

Description

Die vorliegende Erfindung betrifft die Verwendung eines oder mehrerer cyclischer Carbonsäurederivate der allgemeinen Formel I

Figure 00010001
in der

X
für ein Sauerstoffatom oder eine Gruppierung der Formel N-R1 steht, wobei
R1
Wasserstoff oder eine lineare oder verzweigte C1- bis C20-Alkylgruppe bezeichnet, welche noch zusätzlich durch bis zu 9 nicht benachbarte Sauerstoffatome unterbrochen sein und/oder bis zu 6 Hydroxylgruppen tragen kann, oder eine Cycloalkylgruppe oder eine gegebenenfalls substituierte Phenylgruppe bezeichnet,
A
eine Gruppierung der Formel -CR2R3- bezeichnet, wobei
R2 und R3
für Wasserstoff oder C1- bis C8-Alkylgruppen stehen, welche noch zusätzlich durch bis zu 4 nicht benachbarte Sauerstoffatome unterbrochen sein und/oder bis zu 3 Hydroxylgruppen tragen können, und
n
eine Zahl von 2 bis 7 bedeutet,
in hydraulischer Flüssigkeiten, insbesondere Bremsflüssigkeiten für Kraftfahrzeuge, in einer Menge von 0,01 bis 10 Gew.-% zur Erniedrigung der Viskosität, insbesondere der Tieftemperaturviskosität in Anwesenheit von Wasser.The present invention relates to the use of one or more cyclic carboxylic acid derivatives of the general formula I.
Figure 00010001
in the
X
represents an oxygen atom or a grouping of the formula NR 1 , where
R 1
Denotes hydrogen or a linear or branched C 1 - to C 20 -alkyl group, which can additionally be interrupted by up to 9 non-adjacent oxygen atoms and / or can carry up to 6 hydroxyl groups, or denotes a cycloalkyl group or an optionally substituted phenyl group,
A
denotes a grouping of the formula -CR 2 R 3 -, wherein
R 2 and R 3
represent hydrogen or C 1 - to C 8 -alkyl groups, which may additionally be interrupted by up to 4 non-adjacent oxygen atoms and / or may carry up to 3 hydroxyl groups, and
n
means a number from 2 to 7,
in hydraulic fluids, in particular brake fluids for motor vehicles, in an amount of 0.01 to 10% by weight to lower the viscosity, in particular the low-temperature viscosity in the presence of water.

FR-A 2 209 830 (entspricht DE-B 2 260 701) offenbart die Verwendung cyclischer Carbonsäurederivate in Form von N-Alkylpyrrolidonen in hydraulischen Flüssigkeiten in einer Menge von 20 bis 60 Gew.-% zur Verringerung des Verschleißes und zur Verbesserung der Schmiereigenschaften. FR-A 2 209 830 (corresponds to DE-B 2 260 701) discloses the Use of cyclic carboxylic acid derivatives in the form of N-alkylpyrrolidones in hydraulic fluids in an amount of 20 to 60 wt .-% to reduce wear and improve the lubricating properties.

Ullmanns Enzyklopädie der industriellen Chemie, 5. Auflage, Band A 13, Seite 173, lehrt den Einsatz von Pyrrolidon-(2) als Oxidationsinhibitor und Korrosionsinhibitor in Bremsflüssigkeiten.Ullmann's Encyclopedia of Industrial Chemistry, 5th edition, volume A 13, page 173, teaches the use of pyrrolidone- (2) as an oxidation inhibitor and corrosion inhibitor in brake fluids.

Hydraulische Flüssigkeiten und insbesondere Bremsflüssigkeiten für Kraftfahrzeuge unterliegen hinsichtlich ihrer chemischen und physikalischen Eigenschaften sehr hohen Anforderungen. Entsprechend der bestehenden Normen und Spezifikationen für Bremsflüssigkeiten vom US-Department of Tranportation im Federal Motor Vehicle Safety Standard FMVSS-Nr. 116 und der von der Society of Automotive Engineers herausgegebenen Norm SAE J 1704 sollen moderne Bremsflüssigkeiten einerseits über hohe Trockenkochpunkte (Rückflußsiedepunkte, trocken [Equilibrium reflux boiling point, "ERBP"]) sowie hohe Naßkochpunkte (Rückflußsiedepunkte, feucht ["wet ERBP"]) verfügen, andererseits aber auch eine Viskosität aufweisen, die sich innerhalb eines weiten Temperaturbereiches nur wenig ändert. Darüber hinaus bestehen weitergehende Anforderungen aus dem Kreis der Automobilindustrie nach einer niedrigen Tieftemperaturviskosität in Anwesenheit von Wasser.Hydraulic fluids and especially brake fluids for motor vehicles are subject with regard to their chemical and physical properties very high requirements. Corresponding the existing standards and specifications for brake fluids from the U.S. Department of Transportation in the Federal Motor Vehicle Safety Standard FMVSS no. 116 and that of the Society of Automotive Engineers published standard SAE J 1704 are said to be modern Brake fluids on the one hand have high dry boiling points (Reflux boiling points, dry [Equilibrium reflux boiling point, "ERBP"]) and high wet boiling points (reflux points, moist ["wet ERBP"]), but also a viscosity have, which are within a wide temperature range little changes. There are also further requirements from the automotive industry after a low Low temperature viscosity in the presence of water.

Die im Stand der Technik bekannten hydraulischen Flüssigkeiten und Bremsflüssigkeiten für Kraftfahrzeuge sind in dieser Hinsicht jedoch noch verbesserungsbedürftig. Es bestand daher die Aufgabe, hydraulische Flüssigkeiten bereitzustellen, welche die oben genannten Eigenschaften aufweisen.The hydraulic fluids known in the prior art and brake fluids for automobiles are in this regard but still in need of improvement. It was therefore the task to provide hydraulic fluids that meet the above Have properties.

Demgemäß wurde die eingangs definierte Verwendung von hydraulischen oder kraftübertragenden Flüssigkeiten gefunden.Accordingly, the initially defined use of hydraulic or power transmission fluids found.

Bei den cyclischen Carbonsäurederivaten der allgemeinen Formel I handelt es sich insbesondere um cyclische Carbonsäureamide (Lactame) und cyclische Carbonsäureester (Lactone), welche als Vorstufen bei der Herstellung der erstgenannten Lactame dienen können. Als besonders bevorzugte Ringgrößen können hierbei fünf- und sechsgliedrige Ringsysteme eingesetzt werden. Vor allem von Interesse sind N-C1- bis C20-Alkylpyrrolidone-2.The cyclic carboxylic acid derivatives of the general formula I are, in particular, cyclic carboxamides (lactams) and cyclic carboxylic acid esters (lactones), which can serve as precursors in the preparation of the first-mentioned lactams. Five- and six-membered ring systems can be used as particularly preferred ring sizes. Of particular interest are NC 1 to C 20 alkyl pyrrolidones-2.

Das Ringglied X steht vorzugsweise für eine Gruppierung der Formel N-R1.The ring member X preferably represents a grouping of the formula NR 1 .

Der Rest R1 bezeichnet neben Wasserstoff z.B. Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, iso-Butyl, sec.-Butyl, tert.-Butyl, n-Pentyl, iso-Pentyl, sec.-Pentyl, tert.-Pentyl, neo-Pentyl, n-Hexyl, Cyclohexyl, Phenyl, n-Heptyl, n-Octyl, 2-Ethylhexyl, n-Nonyl, iso-Nonyl, n-Decyl, iso-Decyl, n-Undecyl, n-Dodecyl, n-Tridecyl, iso-Tridecyl, n-Tetradecyl, n-Hexydecyl, n-Octadecyl, Eicosyl, 2-Hydroxyethyl, 2-Hydroxypropyl, 3-Hydroxypropyl, 4-Hydroxybutyl, 2-Methoxyethyl, 2-Methoxypropyl, 3-Methoxypropyl, 4-Methoxybutyl, 2-Hydroxy-3-methoxypropyl, 3-Hydroxy-2-methoxypropyl, 2,3-Dihydroxypropyl, 2,3-Dimethoxypropyl sowie Alkylen-. oxy-Gruppierungen der Formel -(CmH2mO)p-Z, in der m die Zahl 2, 3 oder 4 darstellt, p für eine Zahl von 1 bis 9 (für den Fall m=2) bzw. 1 bis 6 (für den Fall m=3) bzw. 1 bis 5 (für den Fall m=4) steht und Z Wasserstoff oder C1- bis C4-Alkyl bedeutet.In addition to hydrogen, the radical R 1 denotes, for example, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, iso-pentyl, sec-pentyl , tert-pentyl, neo-pentyl, n-hexyl, cyclohexyl, phenyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, iso-nonyl, n-decyl, iso-decyl, n-undecyl, n-dodecyl, n-tridecyl, iso-tridecyl, n-tetradecyl, n-hexydecyl, n-octadecyl, eicosyl, 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 4-hydroxybutyl, 2-methoxyethyl, 2-methoxypropyl, 3-methoxypropyl, 4-methoxybutyl, 2-hydroxy-3-methoxypropyl, 3-hydroxy-2-methoxypropyl, 2,3-dihydroxypropyl, 2,3-dimethoxypropyl and alkylene. oxy groupings of the formula - (C m H 2m O) p -Z, in which m represents the number 2, 3 or 4, p for a number from 1 to 9 (for the case m = 2) or 1 to 6 (for the case m = 3) or 1 to 5 (for the case m = 4) and Z is hydrogen or C 1 - to C 4 -alkyl.

Der Rest R1 bezeichnet vorzugsweise Wasserstoff oder eine lineare oder verzweigte C1- bis C6-Alkylgruppe, welche noch zusätzlich durch bis zu 3 nicht benachbarte Sauerstoffatome unterbrochen sein und/oder bis zu 2 Hydroxylgruppen tragen kann, oder eine Cyclohexyl- bzw. Phenylgruppe.The radical R 1 preferably denotes hydrogen or a linear or branched C 1 -C 6 -alkyl group, which can additionally be interrupted by up to 3 non-adjacent oxygen atoms and / or can carry up to 2 hydroxyl groups, or a cyclohexyl or phenyl group ,

Als Beispiele für R2 und R3 können die entsprechenden bei R1 aufgeführten Reste dienen. Vorzugsweise stehen R2 und R3 jedoch für Wasserstoff oder Methylgruppen, vor allem für Wasserstoff.The corresponding radicals listed for R 1 can serve as examples of R 2 and R 3 . However, R 2 and R 3 are preferably hydrogen or methyl groups, especially hydrogen.

Die Zahl n bedeutet vorzugsweise 2, 3 oder 4; damit ergäben sich Ringgrößen von vier- bis sechsgliedrigen Ringen.The number n is preferably 2, 3 or 4; this would result Ring sizes from four to six-membered rings.

Die cyclischen Carbonsäurederivate I sind bekannte Substanzen, die handelsüblich sind oder nach gängigen Herstellungsmethoden synthetisiert werden können.The cyclic carboxylic acid derivatives I are known substances, which are commercially available or according to common manufacturing methods can be synthesized.

Bei der vorliegenden Erfindung enthalten die Bremsflüssigkeiten für Kraftfahrzeuge 0,01 bis 10 Gew.-% eines oder mehrerer der beschriebenen cyclischen Carbonsäurederivate I. Sowohl für hydraulische Flüssigkeiten als auch für Bremsflüssigkeiten für Kraftfahrzeuge sind bevorzugte Gehalte an den Verbindungen I 0,5 bis 10 Gew.-%, bezogen auf die Gesamtmasse der hydraulischen Flüssigkeit bzw. Bremsflüssigkeit.In the present invention, the brake fluids contain for motor vehicles 0.01 to 10 wt .-% of one or more of the described cyclic carboxylic acid derivatives I. Both for hydraulic Liquids as well as brake fluids for motor vehicles are preferred contents of the compounds I 0.5 to 10% by weight, based on the total mass of the hydraulic fluid or brake fluid.

Das Vorliegen der Verbindungen I sorgt in hervorragender Weise dafür, daß die hydraulische Flüssigkeit bzw. Bremsflüssigkeit für Kraftfahrzeuge den eingangs genannten Anforderungen gerecht wird und neben den für Bremsflüssigkeiten vom US-Department of Tranportation im Federal Motor Vehicle Safety Standard FMVSS-Nr. 116 festgelegten Anforderungen der Spezifikationen DOT 5 bzw. DOT 5.1 für silikonfreie Bremsflüssigkeiten zusätzlich auch die verschärften Anforderungen aus dem Kreis der Automobilindustrie nach einer niedrigen Tieftemperaturviskosität in Anwesenheit von Wasser deutlich übertrifft. Die Verbindungen I können also dafür verwendet werden, in hydraulischen Flüssigkeiten bzw. Bremsflüssigkeiten für Kraftfahrzeuge die Viskosität, insbesondere die Tieftemperaturviskosität in Anwesenheit von Wasser, zu erniedrigen, d. h. auf ein niedrigeres Niveau einzustellen.The presence of the compounds I ensures in an excellent manner that the hydraulic fluid or brake fluid for Motor vehicles meet the requirements mentioned above and in addition to those for brake fluids from the US Department of Transportation in the Federal Motor Vehicle Safety Standard FMVSS no. 116 specified requirements of the specifications DOT 5 and DOT 5.1 for silicone-free brake fluids, also the tightened ones Requirements from among the automotive industry a low low temperature viscosity in the presence of water clearly exceeds. The compounds I can therefore be used in hydraulic fluids or brake fluids for motor vehicles the viscosity, in particular the Low temperature viscosity in the presence of water, to decrease d. H. set to a lower level.

Entscheidende Anforderungen für Bremsflüssigkeiten gemäß DOT 5/DOT 5.1-Spezifikation sind: Trockenkochpunkt (Equilibrium reflux boiling pomt; "ERBP") ≥ 260°C Naßkochpunkt ("wet ERBP") ≥ 180°C Kinematische Viskosität bei -40°C ("V") ≤ 900 cSt Crucial requirements for brake fluids according to DOT 5 / DOT 5.1 specification are: Dry cooking point (Equilibrium reflux boiling pomt; "ERBP") ≥ 260 ° C Wet cooking point ("wet ERBP") ≥ 180 ° C Kinematic viscosity at -40 ° C ("V") ≤ 900 cSt

Zusätzliche Anforderung aus der Automobilindustrie für DOT 5.1-Bremsflüssigkeiten sind:

  • Kinematische Viskosität bei -40°C in Gegenwart von 4% Wasser ("V(4%H2O)") : ≤ 1200 cSt
  • Weitere Vorteile der erfindungsgemäß verwendeten hydraulischen Flüssigkeiten und Bremsflüssigkeiten für Kraftfahrzeuge sind deren günstiges Korrosionsverhalten, eine gute Wasserverträglichkeit, ein schonender pH-Wert, eine gute Kälte-, Hochtemperaturund Oxidationsstabilität sowie eine gute chemische Stabilität, eine günstiges Verhalten gegenüber Elastomeren und Gummi sowie ein gutes Schmierverhalten.
    • Additional requirements from the automotive industry for DOT 5.1 brake fluids are:
  • Kinematic viscosity at -40 ° C in the presence of 4% water ("V (4% H 2 O) "): ≤ 1200 cSt
  • Further advantages of the hydraulic fluids and brake fluids for motor vehicles used according to the invention are their favorable corrosion behavior, good water compatibility, a gentle pH value, good cold, high temperature and oxidation stability as well as good chemical stability, favorable behavior towards elastomers and rubber and good lubricating behavior ,

    • Die erfindungsgemäß verwendeten Bremsflüssigkeiten für Kraftfahrzeuge enthalten in einer bevorzugten Ausführungsform neben den Verbindungen I weiterhin 0,1 bis 97 Gew.-%, insbesondere 30 bis 97 Gew.-%, vor allem 50 bis 97 Gew.-%, jeweils bezogen auf die Gesamtmasse der Bremsflüssigkeit, eines oder mehrerer Polyglykolether und/oder deren Borsäureester.The brake fluids used for motor vehicles according to the invention contained in a preferred embodiment in addition to Compounds I further 0.1 to 97 wt .-%, in particular 30 to 97 wt .-%, especially 50 to 97 wt .-%, each based on the Total mass of the brake fluid, one or more polyglycol ethers and / or their boric acid esters.

    Geeignete Polyglykolether sind hierbei vor allem Ethylenglykolmonoalkylether mit bis zu 6 Ethylenoxid-Einheiten und mit bis zu 4 Kohlenstoffatomen im Alkylrest. Weiterhin kommen Ethylenglykoloder Propylenglykoldialkylether mit bis zu 6 Alkylenoxid-Einheiten und mit jeweils bis zu 4 Kohlenstoffatomen in den Alkylresten in Betracht.Suitable polyglycol ethers are especially ethylene glycol monoalkyl ethers with up to 6 ethylene oxide units and with up to 4 Carbon atoms in the alkyl radical. There are also ethylene glycol or Propylene glycol dialkyl ether with up to 6 alkylene oxide units and each with up to 4 carbon atoms in the alkyl radicals into consideration.

    Geeignete Borsäureester der genannten oder von anderen Polyglykolethern sind insbesondere in den Schriften EP-B 013 925 (cyclische Bis-borsäureester), DE-C 28 04 535 (stickstoffhaltige Borsäureester), DE-A 24 38 038 (Borsäure-Alkylenglykol-Monoalkylether-Ester) und DE-B 17 68 933 (Borsäure-tris-alkoxyalkylester) beschrieben. Suitable boric acid esters of those mentioned or of other polyglycol ethers are described in particular in documents EP-B 013 925 (cyclic Bis-boric acid ester), DE-C 28 04 535 (nitrogen-containing boric acid ester), DE-A 24 38 038 (boric acid-alkylene glycol monoalkyl ether ester) and DE-B 17 68 933 (tris-alkoxyalkyl borate) described.

    Anstelle der genannten Polyglykolether und/oder deren Borsäureester können die erfindungsgemäßen Bremsflüssigkeiten für Kraftfahrzeuge als Hauptkomponente auch solche auf Basis von Carbonsäureestern, Mineralölen oder Silikonölen enthalten.Instead of the polyglycol ethers mentioned and / or their boric acid esters can the brake fluids according to the invention for motor vehicles as the main component also those based on carboxylic acid esters, Contain mineral oils or silicone oils.

    Die erfindungsgemäß verwendeten Bremsflüssigkeiten für Kraftfahrzeuge enthalten in einer weiteren bevorzugten Ausführungsform neben den Verbindungen I weiterhin 0,1 bis 50 Gew.-%, insbesondere 1 bis 40 Gew.-%, vor allem 5 bis 30 Gew.-%, jeweils bezogen auf die Gesamtmasse der Bremsflüssigkeit, eines oder mehrerer Polyglykole.The brake fluids used for motor vehicles according to the invention contained in a further preferred embodiment in addition to the compounds I further 0.1 to 50 wt .-%, in particular 1 to 40 wt .-%, especially 5 to 30 wt .-%, each based on the total mass of the brake fluid, one or more polyglycols.

    Geeignete Polyglykole sind hierbei vor allem höhersiedende Umsetzungsprodukte von Ethylenoxid und/oder Propylenoxid und/oder Butylenoxid mit Wasser oder Diolen, insbesondere entsprechende Umsetzungsprodukte von Gemischen aus Ethylenoxid und Propylenoxid mit Wasser finden Verwendung. Die Anzahl der Alkylenoxid-Einheiten in solchen Polyglykolen beträgt normalerweise 2 bis 10.Suitable polyglycols are above all higher-boiling reaction products of ethylene oxide and / or propylene oxide and / or butylene oxide with water or diols, in particular corresponding reaction products of mixtures of ethylene oxide and propylene oxide with water are used. The number of alkylene oxide units in such polyglycols is usually 2 to 10.

    Die Wirkung dieser hochsiedenden Polyglykole ist die eines Schmiermittels, was im wesentlichen auf eine Verbesserung des Temperatur-Viskositäts-Verhaltens zurückzuführen ist. Die Polyglykole verleihen den dünnflüssigen Polyglykolethern bei hohen Temperaturen genügend Viskosität und sorgen damit für eine ausreichende Schmierung. Eine genügende Schmierung ist deshalb in den Bauteilen des Kraftfahrzeug-Bremssystems notwendig, da dort Gummi oder Elastomere auf Metall möglichst verschleißfrei gleiten müssen.The effect of these high-boiling polyglycols is one Lubricant, which essentially indicates an improvement in the Temperature-viscosity behavior is attributable. The polyglycols give the thin polyglycol ethers at high Temperatures sufficient viscosity and thus ensure sufficient Lubrication. Sufficient lubrication is therefore in the components of the motor vehicle braking system necessary because there Glide rubber or elastomers on metal as wear-free as possible have to.

    Die erfindungsgemäß verwendeten Bremsflüssigkeiten für Kraftfahrzeuge enthalten in einer weiteren bevorzugten Ausführungsform neben den Verbindungen I weiterhin 0,01 bis 10 Gew.-%, insbesondere 0,02 bis 6 Gew.-%, vor allem 0,05 bis 4 Gew.-%, jeweils bezogen auf die Gesamtmasse der Bremsflüssigkeit, eines oder mehrerer Korrosionsinhibitoren.The brake fluids used for motor vehicles according to the invention contained in a further preferred embodiment in addition to the compounds I further 0.01 to 10 wt .-%, in particular 0.02 to 6 wt .-%, especially 0.05 to 4 wt .-%, each based on the total mass of the brake fluid, one or more Corrosion inhibitors.

    Korrosionsinhibitoren haben in Bremsflüssigkeiten die Aufgabe, die durch Korrosion verursachte Zerstörung metallischer Werkstoffe zu verhindern. Als Korrosionsinhibitoren kommen hierbei vor allem Alkalimetallsalze von Phosphorsäure und phosphoriger Säure, Fettsäuren wie Capryl-, Laurin-, Palmitin-, Stearin- oder Ölsäure sowie deren Alkalimetallsalze, Ester der Phosphorsäure und der phosphorigen Säure wie Ethylphosphat, Dimethylphosphat, Isopropylphosphat, Diisopropylphosphat, Butylphosphit oder Dimethylphosphit, gegebenenfalls ethoxylierte Mono- und Dialkylamine und deren Salze mit Mineral- und Fettsäuren, z.B. Butylamin, Hexylamin, Octylamin, Isononylamin, Oleylamin, Dipropylamin, Diisopropylamin oder Dibutylamin, gegebenenfalls ethoxylierte Alkanolamine, z.B. Mono-, Di- oder Triethanolamin, N,N'-Din-Butylaminoethanol oder 1,1'-Iminodipropan-2-ol, Cyclohexylamin, Triazole wie Benzo- oder Tolutriazol sowie Nitroaromaten, z.B. 3-Nitrobenzaldehyd, in Betracht.Corrosion inhibitors in brake fluids have the task the destruction of metallic materials caused by corrosion to prevent. Here come as corrosion inhibitors especially alkali metal salts of phosphoric acid and phosphorous Acid, fatty acids such as caprylic, lauric, palmitic, stearic or Oleic acid and its alkali metal salts, esters of phosphoric acid and the phosphorous acid such as ethyl phosphate, dimethyl phosphate, Isopropyl phosphate, diisopropyl phosphate, butyl phosphite or dimethyl phosphite, optionally ethoxylated mono- and dialkylamines and their salts with mineral and fatty acids, e.g. butylamine, Hexylamine, octylamine, isononylamine, oleylamine, dipropylamine, Diisopropylamine or dibutylamine, optionally ethoxylated Alkanolamines, e.g. Mono-, di- or triethanolamine, N, N'-din-butylaminoethanol or 1,1'-iminodipropan-2-ol, cyclohexylamine, Triazoles such as benzo- or tolutriazole and nitroaromatics, e.g. 3-nitrobenzaldehyde.

    Weitere Komponenten und Hilfsmittel in den erfindungsgemäß verwendeten Bremsflüssigkeiten für Kraftfahrzeuge können übliche Antioxidationsmittel, z.B. solche auf Phenolbasis, und übliche Entschäumer sein.Further components and auxiliaries in those used according to the invention Brake fluids for motor vehicles can contain common antioxidants, e.g. those based on phenol, and conventional defoamers his.

    Gegenstand der vorliegenden Erfindung sind auch hydraulische Flüssigkeiten, welche 0,01 bis 10 Gew.-% eines oder mehrerer cyclischer Carbonsäurederivate der allgemeinen Formel I

    Figure 00060001
    in der

    X
    für ein Sauerstoffatom oder eine Gruppierung der Formel N-R1 steht, wobei
    R1
    eine lineare oder verzweigte C1- bis C20-Alkylgruppe, welche noch zusätzlich durch bis zu 9 nicht benachbarte Sauerstoffatome unterbrochen sein und/oder bis zu 6 Hydroxylgruppen tragen kann, oder eine Cycloalkylgruppe oder eine gegebenenfalls substituierte Phenylgruppe bezeichnet,
    A
    eine Gruppierung der Formel -CR2R3- bezeichnet, wobei
    R2 und R3
    für Wasserstoff oder C1- bis C8-Alkylgruppen stehen, welche noch zusätzlich durch bis zu 4 nicht benachbarte Sauerstoffatome unterbrochen sein und/oder bis zu 3 Hydroxylgruppen tragen können, und
    n
    eine Zahl von 2 bis 7 bedeutet,
    enthalten.The present invention also relates to hydraulic liquids which contain 0.01 to 10% by weight of one or more cyclic carboxylic acid derivatives of the general formula I.
    Figure 00060001
    in the
    X
    represents an oxygen atom or a grouping of the formula NR 1 , where
    R 1
    denotes a linear or branched C 1 to C 20 alkyl group which can additionally be interrupted by up to 9 non-adjacent oxygen atoms and / or can carry up to 6 hydroxyl groups, or denotes a cycloalkyl group or an optionally substituted phenyl group,
    A
    denotes a grouping of the formula -CR 2 R 3 -, wherein
    R 2 and R 3
    represent hydrogen or C 1 - to C 8 -alkyl groups, which can additionally be interrupted by up to 4 non-adjacent oxygen atoms and / or can carry up to 3 hydroxyl groups, and
    n
    means a number from 2 to 7,
    contain.

    Anwendungstechnische BeispieleApplication engineering examples

    Von den nachfolgend aufgeführten cyclischen Carbonsäurederivaten, welche handelsüblich sind oder nach gängigen Methoden hergestellt werden können, wurden Formulierungen mit einer üblichen Kraftfahrzeug-Bremsflüssigkeit hergestellt. Die entsprechenden anwendungstechnischen Daten für die derart additivierten Bremsflüssigkeiten wurden ermittelt.Of the cyclic carboxylic acid derivatives listed below, which are commercially available or manufactured using standard methods have been formulations with a common automotive brake fluid manufactured. The corresponding application data for the brake fluids additized in this way were determined.

    Die verwendete Kraftfahrzeug-Bremsflüssigkeit BF 1 ohne Verbindungen I hatte folgende Zusammensetzung: 75 Gew.-% Methyltriglykol-borat, 22 Gew.-% einer Mischung aus Methyldi-, -Methyltri- und Methyltetraglykol, < 3 Gew.-% einer Mischung aus N,N'-Di-n-Butylaminoethanol, 1,1'-Iminodipropan-2-ol, Tolutriazol und 3-Nitrobenzaldehyd < 0,5 Gew.-% Bisphenol A The motor vehicle brake fluid BF 1 used without connections I had the following composition: 75% by weight Methyltriglycol-borate, 22% by weight a mixture of methyldi, methyltri and methyltetraglycol, <3% by weight a mixture of N, N'-di-n-butylaminoethanol, 1,1'-iminodipropan-2-ol, tolutriazole and 3-nitrobenzaldehyde <0.5% by weight Bisphenol A

    Bei den erfindungsgemäß verwendeten Formulierungen wurden von BF 1 ausgehend 5 Gew.-% Methyltriglykol gegen 5 Gew.-% der erfindungsgemäß verwendeten cyclischen Carbonsäurederivate ausgetauscht.In the formulations used according to the invention, BF 1 starting 5 wt .-% methyl triglycol against 5 wt .-% of cyclic carboxylic acid derivatives used according to the invention.

    Die anwendungstechnischen Ergebnisse wurden gemäß der im FMVSS-Standard Nr. 116 bzw. in SAE J 1704 beschriebenen Methoden bestimmt und sind der nachfolgenden Tabelle zu entnehmen: Additiv Gehalt [Gew.-% ] V [cSt ] V(4%H2O) [cSt] wet ERBP [°C] ERBP [°C] N-Methyl-pyrrolidon-2 5 702 1058 184 269 N-iso-Propyl-pyrrolidon-2 5 748 1136 187 269 N-sek.-Butyl-pyrrolidon-2 5 772 1163 186 267 N-tert.-Butyl-pyrrolidon-2 5 790 1196 184 263 N-n-Butyl-pyrrolidon-2 5 757 1141 185 269 N-n-Pentyl-pyrrolidon-2 5 797 1190 186 269 N-n-Hexyl-pyrrolidon-2 5 790 1175 184 270 zum Vergleich: BF 1 - 833 1223 181 269 Hydraulan® 508 - 795 1334 181 269 DOT 5.1 Brake Fluid® - 900 1265 180 262 The application results were determined in accordance with the methods described in FMVSS standard No. 116 or in SAE J 1704 and can be found in the table below: additive Content [% by weight] V [cSt] V (4% H2O) [cSt] wet ERBP [° C] ERBP [° C] N-methyl-pyrrolidone-2 5 702 1058 184 269 N-isopropyl-pyrrolidone-2 5 748 1136 187 269 N-sec-butyl-2-pyrrolidone 5 772 1163 186 267 N-tert-Butyl-2-pyrrolidone 5 790 1196 184 263 Nn-Butyl-2-pyrrolidone 5 757 1141 185 269 Nn-pentyl-pyrrolidone-2 5 797 1190 186 269 Nn-hexyl-pyrrolidone-2 5 790 1175 184 270 for comparison: BF 1 - 833 1223 181 269 Hydraulan® 508 - 795 1334 181 269 DOT 5.1 Brake Fluid® - 900 1265 180 262

    Es wird ersichtlich, daß die erfindungsgemäß verwendeten Formulierungen im Gegensatz zu herkömmlichen DOT 5.1-Bremsflüssigkeiten wie BF 1, Hydraulan 508 der BASF Aktiengesellschaft oder DOT 5.1 Brake Fluid der Firma Motul S.A. (France) zusätzlich zu den Anforderungen der DOT 5.1-Spezifikation auch die darüber hinaus gehende Forderung nach einer niedrigen Viskosität bei -40°C in Anwesenheit von 4% Wasser erfüllen [V(4%H2O) ≤ 1200 cSt].It can be seen that the formulations used according to the invention, in contrast to conventional DOT 5.1 brake fluids such as BF 1, Hydraulan 508 from BASF Aktiengesellschaft or DOT 5.1 Brake Fluid from Motul SA (France), in addition to the requirements of the DOT 5.1 specification, also those above meet further requirements for a low viscosity at -40 ° C in the presence of 4% water [V (4% H 2 O) ≤ 1200 cSt].

    Claims (10)

    1. The use of one or more cyclic carboxylic acid derivatives of the formula I
      Figure 00120001
      where
      X
      is an oxygen atom or a group of the formula N-R1,
      R1
      is hydrogen or a linear or branched C1- to C20- alkyl group which additionally may be interrupted by up to 9 nonneighboring oxygen atoms and/or may carry up to 6 hydroxyl groups, or a cycloalkyl group or an unsubstituted or substituted phenyl group,
      A
      is a group of the formula -CR2R3-,
      R2 and R3
      are each hydrogen or C1- to C8-alkyl groups which additionally may be interrupted by up to 4 nonneighboring oxygen atoms and/or may carry up to 3 hydroxyl groups and
      n
      is from 2 to 7,
      in hydraulic fluids in an amount of from 0.01 to 10% by weight for reducing the viscosity, in particular the low-temperature viscosity in the presence of water.
    2. The use of cyclic carboxylic acid derivatives I, in which X is a group of the formula N-R1, as claimed in claim 1.
    3. The use of cyclic carboxylic acid derivatives I, in which R1 is hydrogen or a linear or branched C1- to C6-alkyl group which additionally may be interrupted by up to 3 nonneighboring oxygen atoms and/or may carry up to 2 hydroxyl groups, as claimed in claim 1 or 2.
    4. The use of cyclic carboxylic acid derivatives I, in which R2 and R3 are each hydrogen or methyl groups, as claimed in any of claims 1 to 3.
    5. The use of cyclic carboxylic acid derivatives I, in which n is 2, 3 or 4, as claimed in any of claims 1 to 4.
    6. The use of cyclic carboxylic acid derivatives I as claimed in any of claims 1 to 5 as brake fluids for motor vehicles, in an amount of from 0.01 to 10% by weight.
    7. The use of cyclic carboxylic acid derivatives I as claimed in claim 6, the brake fluids furthermore containing from 0.1 to 97% by weight of one or more polyglycol ethers and/or boric acid esters thereof in addition to the compounds I.
    8. The use of cyclic carboxylic acid derivatives I as claimed in claim 6 or 7, the brake fluids furthermore containing from 0.1 to 50% by weight of one or more polyglycols in addition to the compounds I.
    9. The use of cyclic carboxylic acid derivatives I as claimed in any of claims 6 to 8, the brake fluids furthermore containing from 0.01 to 10% by weight of one or more corrosion inhibitors in addition to the compounds I.
    10. A hydraulic fluid, comprising from 0.01 to 10% by weight of one or more cyclic carboxylic acid derivatives of the formula I
      Figure 00140001
      where
      X
      is an oxygen atom or a group of the formula N-R1,
      R1
      is a linear or branched C1- to C20-alkyl group which additionally may be interrupted by up to 9 nonneighboring oxygen atoms and/or may carry up to 6 hydroxyl groups, or a cycloalkyl group or an unsubstituted or substituted phenyl group,
      A
      is a group of the formula -CR2R3-,
      R2 and R3
      are each hydrogen or C1- to C8-alkyl groups which additionally may be interrupted by up to 4 nonneighboring oxygen atoms and/or may carry up to 3 hydroxyl groups and
      n
      is from 2 to 7.
    EP00922626A 1999-04-22 2000-04-11 Hydraulic fluids, containing cyclic carboxylic acid derivatives Expired - Lifetime EP1171552B1 (en)

    Applications Claiming Priority (3)

    Application Number Priority Date Filing Date Title
    DE19918199A DE19918199A1 (en) 1999-04-22 1999-04-22 Hydraulic fluid, especially motor vehicle brake fluid, contains one or more cyclic esters or amides of carboxylic acids, e.g. N-methyl-pyrrolidone
    DE19918199 1999-04-22
    PCT/EP2000/003230 WO2000065001A1 (en) 1999-04-22 2000-04-11 Hydraulic fluids, containing cyclic carboxylic acid derivatives

    Publications (2)

    Publication Number Publication Date
    EP1171552A1 EP1171552A1 (en) 2002-01-16
    EP1171552B1 true EP1171552B1 (en) 2003-06-18

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    WO2004074547A2 (en) * 2003-02-19 2004-09-02 Intellectual Concepts, Llc Lower alkyl carboxylic acid moiety-containing anti- corrosion compositions and methods of use.
    JP2015516495A (en) 2012-05-15 2015-06-11 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ Novel low viscosity functional liquid composition
    US20130310286A1 (en) * 2012-05-15 2013-11-21 Basf Se Novel low viscosity functional fluid composition
    JP6422958B2 (en) 2013-10-10 2018-11-14 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ Novel functional fluid composition
    EP3938479B1 (en) 2020-04-23 2023-06-07 Clariant International Ltd Low viscosity functional fluid composition
    EP3929269A1 (en) 2020-06-22 2021-12-29 Clariant International Ltd Low viscosity functional fluid composition
    EP4056669A1 (en) 2021-03-12 2022-09-14 Clariant International Ltd Low viscosity functional fluid composition
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    US3334048A (en) * 1963-01-17 1967-08-01 Castrol Ltd Hydraulic fluids
    US3637794A (en) 1967-04-13 1972-01-25 Olin Mathieson Borate esters prepared by successive reactions of boric acid with glycol monoethers and polyols
    GB1323061A (en) * 1969-06-16 1973-07-11 Castrol Ltd Functional fluids and additives therefor
    DE2260701C2 (en) * 1972-12-12 1974-09-12 Basf Ag, 6700 Ludwigshafen Hydraulic fluids
    JPS5046584A (en) * 1973-08-11 1975-04-25
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