EP1171552A1 - Hydraulische flüssigkeiten, enthaltend cyclische carbonsäurederivate - Google Patents

Hydraulische flüssigkeiten, enthaltend cyclische carbonsäurederivate

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Publication number
EP1171552A1
EP1171552A1 EP00922626A EP00922626A EP1171552A1 EP 1171552 A1 EP1171552 A1 EP 1171552A1 EP 00922626 A EP00922626 A EP 00922626A EP 00922626 A EP00922626 A EP 00922626A EP 1171552 A1 EP1171552 A1 EP 1171552A1
Authority
EP
European Patent Office
Prior art keywords
carboxylic acid
acid derivatives
weight
motor vehicles
brake fluids
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.)
Granted
Application number
EP00922626A
Other languages
English (en)
French (fr)
Other versions
EP1171552B1 (de
Inventor
Bayram Aydin
Uwe Fidorra
Arthur Höhn
Ladislaus Meszaros
Jan Nouwen
Knut Oppenländer
Michael Roida
Michael Stösser
Bernd Wenderoth
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP1171552A1 publication Critical patent/EP1171552A1/de
Application granted granted Critical
Publication of EP1171552B1 publication Critical patent/EP1171552B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • 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
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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
    • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
    • 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

  • the present invention relates to hydraulic fluids, in particular brake fluids for motor vehicles, which contain 0.01 to 50% by weight of one or more cyclic carboxylic acid derivatives of the general formula I.
  • X represents an oxygen atom or a grouping of the formula NR 1 , where
  • R 1 denotes hydrogen or a linear or branched Ci to C 2 o ⁇ 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 a cycloalkyl group or an optionally denotes substituted phenyl group,
  • A denotes a grouping of the formula -CRR 3 -, where
  • R 2 and R 3 represent hydrogen or C 1 -C 6 -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 a number from 2 to 7
  • Hydraulic fluids and especially brake fluids for motor vehicles are subject to very high requirements with regard to their chemical and physical properties.
  • According to the existing standards and specifications for brake fluids from the US Department of Transportation in the Federal Motor Vehicle Safety Standard FMVSS-No. 116 and the standard SAE J 1704 published by the Society of Automotive Engineers are intended to modern brake fluids on the one hand via high dry boiling points (reflux boiling points, dry [Equilibrium reflux boiling point. "ERBP”]) and high wet boiling points (reflux boiling points, moist ["wet ERBP”]), but on the other hand also have a viscosity which changes only slightly within a wide temperature range.
  • ERBP Equilibrium reflux boiling point
  • 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.
  • Of particular interest are N-C ⁇ ⁇ to C o-alkylpyrrolidones-2.
  • the ring member X preferably represents a grouping of the formula NR 1 .
  • 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.
  • 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
  • the radical R 1 preferably denotes hydrogen or a linear or branched C 1 -C 6 -alkyl group, which is additionally interrupted by up to 3 non-adjacent oxygen atoms be 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 in ring sizes of four to six-membered rings.
  • the cyclic carboxylic acid derivatives I are known substances which are commercially available or can be synthesized by customary production methods.
  • a preferred embodiment of the present invention are brake fluids for motor vehicles which contain 0.01 to 50% by weight of one or more of the cyclic carboxylic acid derivatives I described.
  • preferred contents of the compounds I are 0.05 to 30% by weight, in particular 0.1 to 20% by weight, especially 0.5 to 10% by weight, in each case 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 meets the requirements mentioned at the beginning 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 clearly exceeds the more stringent requirements from the automotive industry for a low low-temperature viscosity in the presence of water.
  • the compounds I can therefore be used to lower the viscosity, in particular the low-temperature viscosity, in the presence of water in hydraulic fluids or brake fluids for motor vehicles, ie. H. set to a lower level.
  • hydraulic fluids and brake fluids for motor vehicles are their favorable corrosion behavior, good water compatibility, a gentle pH value, good resistance to cold, high temperature and oxidation as well as good chemical stability, a favorable behavior towards elastomers and rubber and good lubrication behavior.
  • the brake fluids for motor vehicles according to the invention also contain 0.1 to 97% by weight, in particular 30 to 97% by weight, in particular 50 to 97% by weight, in each case based on the total mass of the compounds I Brake fluid, one or more polyglycol ethers and / or their boric acid esters.
  • 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. Ethylene glycol or propylene glycol dialkyl ethers with up to 6 alkylene oxide units and each with up to 4 carbon atoms in the alkyl radicals are also suitable.
  • Suitable boric acid esters of the polyglycol ethers mentioned or of other polyglycol ethers are particularly described in EP-B 013 925 (cyclic bis-boric acid esters), DE-C 28 04 535 (nitrogen-containing boric acid esters), DE-A 24 38 038 (boric acid-alkylene glycol monoalkyl) - ether esters) and DE-B 17 68 933 (tris-alkoxyalkyl borate) described.
  • the brake fluids according to the invention for motor vehicles can also contain, as the main component, those based on carboxylic acid esters, mineral oils or silicone oils.
  • the brake fluids for motor vehicles according to the invention contain, in addition to the compounds I, 0.1 to 50% by weight, in particular 1 to 40% by weight, especially 5 to 30% by weight, based in each case on the Ge - 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 normally 2 to 10.
  • the effect of these high-boiling polyglycols is that of a lubricant, which is essentially due to an improvement in the temperature-viscosity behavior.
  • the polyglycols give the low viscosity polyglycol ethers sufficient viscosity at high temperatures and thus ensure adequate lubrication. Adequate lubrication is therefore necessary in the components of the motor vehicle brake system, since rubber or elastomers on metal have to slide as wear-free as possible.
  • the brake fluids for motor vehicles according to the invention contain, in addition to the compounds I, 0.01 to 10% by weight, in particular 0.02 to 6% by weight, especially 0.05 to 4% by weight, in each case based on the total mass of the brake fluid, one or more corrosion inhibitors.
  • Corrosion inhibitors in brake fluids have the task of preventing the destruction of metallic materials caused by corrosion.
  • the main corrosion inhibitors here are alkali metal salts of phosphoric acid and phosphorous acid, fatty acids such as caprylic, lauric, palmitic, stearic or oleic acid and their alkali metal salts, esters of phosphoric acid and phosphorous acid such as ethyl phosphate, dimethyl phosphate, isopropyl phosphate, diisopropyl phosphate or butisyl Dimethyl phosphite, optionally ethoxylated mono- and dialkylamines and their salts with mineral and fatty acids, for example Butylamine, hexylamine, octylamine, isononylamine, oleylamine, dipropylamine, diisopropylamine or dibutylamine, optionally ethoxylated alkanolamines, e.g.
  • Formulations of a conventional motor vehicle brake fluid were produced from the cyclic carboxylic acid derivatives listed below, which are commercially available or can be prepared by customary methods. The corresponding application data for the brake fluids additized in this way were determined.
  • the motor vehicle brake fluid BF 1 used without connections I had the following composition:
  • methyltriglycol-borate 75% by weight of methyltriglycol-borate, 22% by weight of a mixture of methyldi-methyltri- and methyl-tetraglycol,
  • DOT 5.1 Brake Fluid® 900 1265 180 262 It can be seen that the formulations 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 beyond that

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Description

Hydraulische Flüssigkeiten, enthaltend cyclische Carbonsäurederivate
Beschreibung
Die vorliegende Erfindung betrifft hydraulische Flüssigkeiten, insbesondere Bremsflüssigkeiten für Kraftfahrzeuge, welche 0,01 bis 50 Gew.-% eines oder mehrerer cyclischer Carbonsäurederivate der allgemeinen Formel I
I c=o (i)
(A) n
in der
X für ein Sauerstoffatom oder eine Gruppierung der Formel N-R1 steht, wobei
R1 Wasserstoff oder eine lineare oder verzweigte Ci- bis C2o~Al- kylgruppe bezeichnet, welche noch zusätzlich durch bis zu 9 nicht benachbarte Sauerstoffatome unterbrochen sein und/oder bis zu 6 Hydroxylgruppen tragen kann, oder eine Cycloalkyl- gruppe oder eine gegebenenfalls substituierte Phenylgruppe bezeichnet,
A eine Gruppierung der Formel -CRR3- bezeichnet, wobei
R2 und R3 für Wasserstoff oder Cι~ bis Cg-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.
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 Ve- hicle 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 stehen weitergehende Anforderun- gen aus dem Kreis der Automobilindustrie nach einer niedrigen Tieftemperaturviskosität in Anwesenheit von Wasser.
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.
Demgemäß wurden die eingangs definierten hydraulischen oder kraftübertragenden Flüssigkeiten gefunden.
Bei den cyclischen Carbonsäurederivaten der allgemeinen Formel I handelt es sich insbesondere um cyclische Carbonsäureamide (Lactame) und cyclische Carbonsäureester (Lactone) , welche als Vor- stufen 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-Cι~ bis C o-Alkylpyrrolidone-2.
Das Ringglied X steht vorzugsweise für eine Gruppierung der Formel N-R1.
Der Rest R1 bezeichnet neben Wasserstoff z.B. Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, iso-Butyl, sec.-Butyl, tert.-Bu- tyl, 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-Hy- droxybutyl, 2-Methoxyethyl, 2-Methoxypropyl, 3-Methoxypropyl, 4-Methoxybutyl, 2-Hydroxy-3-methoxypropyl, 3-Hydroxy-2-methoxy- propyl, 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 C ~ bis C -Alkyl bedeutet.
Der Rest R1 bezeichnet vorzugsweise Wasserstoff oder eine lineare oder verzweigte Cι~ 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 Cy- clohexyl- bzw. Phenylgruppe.
Als Beispiele für R2 und R3 können die entsprechenden bei R1 auf - geführten Reste dienen. Vorzugsweise stehen R2 und R3 jedoch für Wasserstoff oder Methylgruppen, vor allem für Wasserstoff.
Die Zahl n bedeutet vorzugsweise 2, 3 oder 4; damit ergäben sich Ringgrößen von vier- bis sechsgliedrigen Ringen.
Die cyclischen Carbonsäurederivate I sind bekannte Substanzen, die handelsüblich sind oder nach gängigen Herstellungsmethoden synthetisiert werden können.
Eine bevorzugte Ausfuhrungsform der vorliegenden Erfindung sind Bremsflüssigkeiten für Kraftfahrzeuge, welche 0,01 bis 50 Gew.-% eines oder mehrerer der beschriebenen cyclischen Carbonsäurederivate I enthalten. Sowohl für hydraulische Flüssigkeiten als auch für Bremsflüssigkeiten für Kraftfahrzeuge sind bevorzugte Gehalte an den Verbindungen I 0,05 bis 30 Gew.-%, insbesondere 0,1 bis 20 Gew.-%, vor allem 0,5 bis 10 Gew.-%, jeweils bezogen auf die Gesamtmasse der hydraulischen Flüssigkeit bzw. Bremsflüssigkeit.
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. Bremsflüs- sigkeiten für Kraftfahrzeuge die Viskosität, insbesondere die Tieftemperaturviskosität in Anwesenheit von Wasser, zu erniedrigen, d. h. auf ein niedrigeres Niveau einzustellen.
Entscheidende Anforderungen für Bremsflüssigkeiten gemäß DOT 5/DOT 5.1-Spezifikation sind:
Trockenkochpunkt (Equilibrium reflux boiling point; "ERBP") : > 260°C Naßkochpunkt ("wet ERBP"): > 180°C
Kinematische Viskosität bei -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 erfindungsgemäßen hydraulischen Flüssigkeiten und Bremsflüssigkeiten für Kraftfahrzeuge sind deren günstiges Korrosionsverhalten, eine gute Wasserverträglichkeit, ein schonender pH-Wert, eine gute Kälte-, Hochtemperatur- und Oxida- tionsstabilität sowie eine gute chemische Stabilität, eine günstiges Verhalten gegenüber Elastomeren und Gummi sowie ein gutes Schmierverhalten.
Die erfindungsgemäßen 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.
Geeignete Polyglykolether sind hierbei vor allem Ethylenglykolmo- noalkylether mit bis zu 6 Ethylenoxid-Einheiten und mit bis zu 4 Kohlenstoffatomen im Alkylrest. Weiterhin kommen Ethylenglykol- oder Propylenglykoldialkylether mit bis zu 6 Alkylenoxid-Einhei- ten und mit jeweils bis zu 4 Kohlenstoffatomen in den Alkylresten in Betracht.
Geeignete Borsäureester der genannten oder von anderen Polyglyko- lethern 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-Monoalkyl- ether-Ester) und DE-B 17 68 933 (Borsäure-tris-alkoxyalkylester) beschrieben.
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.
Die erfindungsgemäßen 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 Ge- samtmasse der Bremsflüssigkeit, eines oder mehrerer Polyglykole. Geeignete Polyglykole sind hierbei vor allem höhersiedende Umsetzungsprodukte von Ethylenoxid und/oder Propylenoxid und/oder Bu- tylenoxid mit Wasser oder Diolen, insbesondere entsprechende Umsetzungsprodukte von Gemischen aus Ethylenoxid und Propylenoxid mit Wasser finden Verwendung. Die Anzahl der Alkylenoxid-Einhei - ten in solchen Polyglykolen beträgt normalerweise 2 bis 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.
Die erfindungsgemäßen 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.
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 Dime- thylphosphit, 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'-Di- n-Butylaminoethanol oder 1, 1' -Iminodipropan-2-ol, Cyclohexylamin, Triazole wie Benzo- oder Tolutriazol sowie Nitroaromaten, z.B. 3-Nitrobenzaldehyd, in Betracht.
Weitere Komponenten und Hilfsmittel in den erfindungsgemäßen Bremsflüssigkeiten für Kraftfahrzeuge können übliche Antioxida- tionsmittel, z.B. solche auf Phenolbasis, und übliche Entschäumer sein. Anwendungstechnische Beispiele
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.
Die verwendete Kraftfahrzeug-Bremsflüssigkeit BF 1 ohne Verbindungen I hatte folgende Zusammensetzung:
75 Gew.-% Methyltriglykol-borat, 22 Gew.-% einer Mischung aus Methyldi- -Methyltri- und Methyl- tetraglykol,
< 3 Gew.-% einer Mischung aus N,N' -Di-n-Butylaminoethanol,
1, 1' -Iminodipropan-2-ol, Tolutriazol und 3-Nitro- benzaldehyd
< 0,5 Gew.-% Bisphenol A
Bei den erfindungsgemäßen Formulierungen wurden von BF 1 ausgehend 5 Gew.-% Methyltriglykol gegen 5 Gew.-% der erfindungsgemäßen cyclischen Carbonsäurederivate ausgetauscht.
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 V (4%H20) wet ERBP ERBP
[Gew. -% [cSt [cSt] [°C] [°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 Es wird ersichtlich, daß die erfindungsgemäßen 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 Anforderun- gen 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%H2OI < 1200 cSt] .

Claims

Patentansprüche
1. Hydraulische Flüssigkeiten, enthaltend 0,01 bis 50 Gew.-% ei- nes oder mehrerer cyclischer Carbonsäurederivate der allgemeinen Formel I
X^\
I ^,C=0 (I) <A)n
in der
X für ein Sauerstoffatom oder eine Gruppierung der Formel N-R1 steht, wobei
R1 Wasserstoff oder eine lineare oder verzweigte Cι~ bis C o~Alkylgruppe, welche noch zusätzlich durch bis zu 9 nicht benachbarte Sauerstoffatome unterbrochen sein und/ oder bis zu 6 Hydroxylgruppen tragen kann, oder eine Cy- cloalkylgruppe oder eine gegebenenfalls substituierte Phenylgruppe bezeichnet,
A eine Gruppierung der Formel -CR2R3- bezeichnet, wobei
R2 und R3 für Wasserstoff oder Cι~ bis Cs-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.
2. Hydraulische Flüssigkeiten nach Anspruch 1, enthaltend ein oder mehrere Carbonsäurederivate I, bei denen X für eine Gruppierung der Formel N-R1 steht.
3. Hydraulische Flüssigkeiten nach Anspruch 1 oder 2, enthaltend ein oder mehrere Carbonsäurederivate I, bei denen R1 Wasserstoff oder eine lineare oder verzweigte Cι~ bis Cß-Alkylgruppe bezeichnet, welche noch zusätzlich durch bis zu 3 nicht benachbarte Sauerstoffatome unterbrochen sein und/oder bis zu 2 Hydroxylgruppen tragen kann.
4. Hydraulische Flüssigkeiten nach den Ansprüchen 1 bis 3, enthaltend ein oder mehrere Carbonsäurederivate I, bei denen R2 und R3 für Wasserstoff oder Methylgruppen stehen.
5. Hydraulische Flüssigkeiten nach den Ansprüchen 1 bis 4, enthaltend ein oder mehrere Carbonsaurederivate I, bei denen n die Zahl 2, 3 oder 4 bedeutet.
6. Bremsflüssigkeiten für Kraftfahrzeuge, enthaltend 0,01 bis
50 Gew.-% eines oder mehrerer cyclischer Carbonsaurederivate gemäß den Ansprüchen 1 bis 5.
7. Bremsflüssigkeiten für Kraftfahrzeuge nach Anspruch 6, ent- haltend neben den Verbindungen I weiterhin 0,1 bis 95 Gew.-% eines oder mehrerer Polyglykolether und/oder deren Borsäure- ester.
8. Bremsflüssigkeiten für Kraftf hrzeuge nach Anspruch 6 oder 7, enthaltend neben den Verbindungen I weiterhin 0,1 bis
50 Gew.-% eines oder mehrerer Polyglykole.
9. Bremsflüssigkeiten für Kraftfahrzeuge nach den Ansprüchen 6 bis 8, enthaltend neben den Verbindungen I weiterhin 0,01 bis 10 Gew.-% eines oder mehrerer Korrosionsinhibitoren.
EP00922626A 1999-04-22 2000-04-11 Hydraulische flüssigkeiten, enthaltend cyclische carbonsäurederivate Expired - Lifetime EP1171552B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19918199A DE19918199A1 (de) 1999-04-22 1999-04-22 Hydraulische Flüssigkeiten, enthaltend cyclische Carbonsäurederivate
DE19918199 1999-04-22
PCT/EP2000/003230 WO2000065001A1 (de) 1999-04-22 2000-04-11 Hydraulische flüssigkeiten, enthaltend cyclische carbonsäurederivate

Publications (2)

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

Family

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Application Number Title Priority Date Filing Date
EP00922626A Expired - Lifetime EP1171552B1 (de) 1999-04-22 2000-04-11 Hydraulische flüssigkeiten, enthaltend cyclische carbonsäurederivate

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US (1) US6783693B1 (de)
EP (1) EP1171552B1 (de)
JP (1) JP2002543238A (de)
KR (1) KR100660953B1 (de)
AT (1) ATE243248T1 (de)
CA (1) CA2367913C (de)
DE (2) DE19918199A1 (de)
ES (1) ES2202113T3 (de)
PT (1) PT1171552E (de)
WO (1) WO2000065001A1 (de)

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US20040234701A1 (en) * 2003-02-19 2004-11-25 Caton Gregory James Lower alkyl carboxylic acid moieties as organoleptic stabilizers and preservatives of food and beverages and for preventing oxidative corrosion of metals
JP2015516495A (ja) 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 新規の低粘度機能性液体組成物
US20130310286A1 (en) * 2012-05-15 2013-11-21 Basf Se Novel low viscosity functional fluid composition
US10941367B2 (en) 2013-10-10 2021-03-09 Basf Se Functional fluid composition
JP7157247B2 (ja) 2020-04-23 2022-10-19 クラリアント・インターナシヨナル・リミテツド 低粘度機能性流体組成物
EP3929269A1 (de) 2020-06-22 2021-12-29 Clariant International Ltd Funktionale fluidzusammensetzung mit niedriger viskosität
EP4056669A1 (de) 2021-03-12 2022-09-14 Clariant International Ltd Niedrigviskose funktionsflüssigkeitszusammensetzung
EP4130211A1 (de) 2021-08-02 2023-02-08 Clariant International Ltd Funktionale fluidzusammensetzung mit niedriger viskosität

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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 (de) * 1972-12-12 1974-09-12 Basf Ag, 6700 Ludwigshafen Hydraulikflüssigkeiten
JPS5046584A (de) 1973-08-11 1975-04-25
DE2804535C2 (de) 1978-02-03 1984-04-26 Alfred Teves Gmbh, 6000 Frankfurt Hydraulische Flüssigkeiten
DE2901835A1 (de) 1979-01-18 1980-07-31 Hoechst Ag Hydraulische fluessigkeiten
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Title
See references of WO0065001A1 *

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US6783693B1 (en) 2004-08-31
KR20020010606A (ko) 2002-02-04
DE50002594D1 (de) 2003-07-24
JP2002543238A (ja) 2002-12-17
DE19918199A1 (de) 2000-10-26
PT1171552E (pt) 2003-10-31
KR100660953B1 (ko) 2006-12-26
ES2202113T3 (es) 2004-04-01
EP1171552B1 (de) 2003-06-18
WO2000065001A1 (de) 2000-11-02
CA2367913A1 (en) 2000-11-02
ATE243248T1 (de) 2003-07-15
CA2367913C (en) 2008-01-08

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