EP0013925A1 - Bremsflüssigkeit für Motorfahrzeuge - Google Patents
Bremsflüssigkeit für Motorfahrzeuge Download PDFInfo
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- EP0013925A1 EP0013925A1 EP80100161A EP80100161A EP0013925A1 EP 0013925 A1 EP0013925 A1 EP 0013925A1 EP 80100161 A EP80100161 A EP 80100161A EP 80100161 A EP80100161 A EP 80100161A EP 0013925 A1 EP0013925 A1 EP 0013925A1
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M111/00—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
- C10M111/04—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential at least one of them being a macromolecular organic compound
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- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
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- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/106—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing four carbon atoms only
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
Definitions
- the invention relates to a hydraulic fluid based on boric acid esters and ethylene glycol monoalkyl ethers
- brake fluids In hydraulic fluids, especially brake fluids, in chemical and ph y sikali- rule properties high demands.
- brake fluids should be one have a particularly high dry boiling point (reflux boiling point dry) and wet boiling point (reflux boiling point wet) and have a viscosity that changes only slightly over a wide temperature range.
- Brake fluids based on (a) boric acid esters made of orthoboric acid, alkylene glycol monoalkyl ethers and / or alky are described in the German patent application 17 68 933 and in the German patent applications 24 37 936 and 24 38 038 Lenglykolen, (b) polyoxalkylene glycol monoalkyl ethers and optionally (c) polyoxalkylene glycols.
- these known hydraulic fluids still leave something to be desired with regard to the requirements mentioned at the outset.
- the new brake fluid should also meet both the DOT 3 and DOT 4 specifications in order to meet the various requirements in technical use.
- R and R 1 , x and y can be the same or different.
- the alkyl group R and R can be straight-chain or branched, preferably it is straight-chain.
- Preferred boric acid esters of the formula I are those in which R and R 1 are an alkyl group having 1 to 4 carbon atoms, and x and y are 2 or 3.
- Boric acid esters of the formula I are particularly preferred, in which R and R 1 are methyl, ethyl, propyl or butyl, and x and y are 2 or 3.
- the preparation of the boric acid esters of the formula I - a reaction product of orthoboric acid, diethylene glycol and an ethylene glycol monoalkyl ether suitable according to formula I in a molar ratio of 1: 1: 1 - is carried out according to procedures known per se.
- the reaction components mentioned are in a reaction vessel equipped with a stirrer and optionally a reflux condenser at a temperature of about 50 to about 150 ° C., preferably about 110 to about 140 ° C., is reacted with stirring, the water of reaction formed being continuously removed.
- the reaction is advantageously carried out in the presence of an inert solvent which forms an azeotrope with water, such as, for example, benzene, toluene, xylene, ethylbenzene and the like.
- the water of reaction can also be removed by carrying out the reaction under reduced pressure, for example in a water jet vacuum (7 to 20 mbar).
- a water jet vacuum 7.0 to 20 mbar.
- it is advantageous to take the ethylene glycol monoalkyl ether in excess that is to say to use the three reaction components mentioned preferably in molar amounts by weight of about 1: 1: 1.2 to 1: 1: 2.5.
- the solvent which may be used is removed from the reaction product by customary distillation and, if further purification should be necessary, it is expediently vacuum-stripped at a temperature of 90 to 150 ° C. (pressure about 7 to 20 mbar).
- the alkyl group R 2 can be straight-chain or branched, preferably it is straight-chain.
- Preferred ethylene glycol monoalkyl ethers of the formula II are those in which R 2 is methyl, ethyl, propyl or butyl and n is 2 to 4.
- a particularly preferred ethylene glycol monoalkyl ether according to formula II is methyl triethylene glycol
- component C in particular corrosion and oxidation (antioxidant), they can be used in the formulation of hydraulic fluids, common connections are used.
- the corrosion inhibitors are generally used in an amount of 1 to 10% by weight, preferably 2 to 8% by weight, based on the total weight of the liquid.
- the antioxidants are generally used in an amount of from 0.01 to 2.0% by weight, preferably from 0.05 to 1.0% by weight, based on the total weight of the liquid.
- the hydraulic fluid according to the invention preferably contains 15 to 20% by weight of component A), 55 to 65% by weight of component B) and 3 to 8% by weight of component C), in each case based on the total weight the liquid.
- the hydraulic fluid according to the invention can also contain D) dialkyl polyalkylene glycols of the formula III and / or E) polyoxyalkylene glycols of the formula IV.
- these components can be used to precisely set a desired viscosity.
- alkyl polyethylene glycol tert-butyl ethers have proven to be particularly suitable.
- Alkyl polyethylene glycol tert-butyl ethers of the formula are preferably used in R 3 is a straight-chain or branched alkyl radical with 1 to 4 carbon atoms and z is an integer from 2 to 10, preferably 2 to 5.
- These polyethylene glycol diethers are described in German Offenlegungsschrift 23 50 569.
- the proportion of compounds of the formula III, provided they are used in the hydraulic fluid according to the invention, is 0.5 to 15% by weight, preferably 5 to 10% by weight, based on the total weight of the fluid.
- Compounds of formula IV which can be used are polyethylene glycols, polypropylene glycols and polybutylene glycols.
- the proportion of polyoxyalkylene glycols of the formula IV, provided they are used in the hydraulic fluid according to the invention, is 0.5 to 20% by weight, preferably 5 to 18% by weight, based on the total weight of the fluid.
- the hydraulic liquids according to the invention are produced by mixing the components together, for example in a container with a stirrer, as a result of which a homogeneous mixture is obtained in a simple manner.
- the mixing is carried out at atmospheric pressure and at room temperature, it can optionally also be carried out at a higher temperature (30 to 50 ° C.), it being advisable to keep moisture away.
- a brake fluid according to the invention is produced by mixing the following components:
- This brake fluid has the following properties, measured in accordance with FMVSS No. 116 for DOT 3 and DOT 4 brake fluids:
- FMVSS 116 For comparison, the requirements for a DOT 3 brake fluid and a DOT 4 brake fluid are given below:
- This brake fluid has the following properties:
- the examples show that the hydraulic fluid according to the invention, which contains very specific boric acid esters of the formula I and alkylene glycol monoalkyl ethers of the formula II in a quantitatively specific amount, has outstanding values in the decisive properties, namely viscosity, dry boiling point and wet boiling point.
- the rubber swelling values that are particularly important for technical use are surprisingly good.
- the water-insensitive hydraulic fluids according to the invention are particularly suitable for hydraulic brake systems, preferably of motor vehicles, for hydraulic control systems and hydraulic transmissions.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Braking Arrangements (AREA)
- Valves And Accessory Devices For Braking Systems (AREA)
- Fluid-Pressure Circuits (AREA)
- Curing Cements, Concrete, And Artificial Stone (AREA)
Abstract
Description
- Die Erfindung betrifft eine hydraulische Flüssigkeit auf der Basis von Borsäureestern und Ethylenglykol-monoalkylethern
- An hydraulische Flüssigkeiten, insbesondere an Bremsflüssigkeiten, werden hinsichtlich ihrer chemischen und physikali- schen Eigenschaften hohe Anforderungen gestellt. Entsprechend den derzeit bestehenden Normen (vgl. Spezifikationen DOT 3 und DOT 4 vom US-Department of Transportation in Federal Motor Vehicle Safety Standard = FMVSS-Nr. 116 und Spezifikation SAE-J 1703 der Society of Automotive Engineers, New York) sollen Bremsflüssigkeiten einen besonders hohen Trocken-Siedepunkt (Rückflußsiedepunkt-trocken) und Naß-Siedepunkt (Rückflußsiedepunkt-feucht) besitzen und eine Viskosität aufweisen, die sich innerhalb eines weiten Temperaturbereiches nur wenig ändert.
- In der deutschen Auslegeschrift 17 68 933 und in den deutschen Offenlegungsschriften 24 37 936 und 24 38 038 sind Bremsflüssigkeiten auf der Basis von (a) Borsäureestern aus Orthoborsäure, Alkylenglykol-monoalkylethern und/oder Alkylenglykolen, (b) Polyoxalkylenglykol-monoalkylethern und gegebenenfalls (c) Polyoxalkylenglykolen beschrieben. Diese bekannten hydraulischen Flüssigkeiten lassen jedoch bezüglich der eingangs genannten Anforderungen noch zu wünschen übrig.
- Es ist demnach Aufgabe der Erfindung, eine hydraulische Flüssigkeit, insbesondere eine Bremsflüssigkeit zu schaffen, die eine ausgezeichnete Viskosität besitzt und einen hohen Trocken-Siedepunkt und Naß-Siedepunkt aufweist. Die neue Bremsflüssigkeit soll darüberhinaus, um eben den verschiedenartigen Anforderungen im technischen Gebrauch gerecht zu werden, sowohl die Spezifikation DOT 3 und DOT 4 erfüllen.
- Die erfindungsgemäße hydraulische Flüssigkeit besteht aus:
- A) 10 bis 30 Gew.-%, bezogen auf Gesamtgewicht der Flüssigkeit, von mindestens einem Borsäureester der allgemeinen Formel I
- B) 50 bis 80 Gew.-%, bezogen auf das Gesamtgewicht der Flüssigkeit, von mindestens einem Ethylenglykol-monoalkylether der allgemeinen Formel II
- C) 1 bis 10 Gew.-%, bezogen auf das Gesamtgewicht der Flüssigkeit, von mindestens einem Inhibitor,
- D) 0 bis 15 Gew.-%, bezogen auf das Gesamtgewicht der Flüssigkeit, von mindestens einer Verbindung der Formel III
- E) 0 bis 20 Gew.-%, bezogen auf das Gesamtgewicht der Flüssigkeit, von mindestens einer Verbindung der Formel
- Bei den Borsäureestern der Formel I (Komponente A) können R und R1, x und y gleich oder verschieden sein. Die Alkylgruppe R und R, kann geradkettig oder verzweigt sein, vorzugsweise ist sie geradkettig.
- Bevorzugte Borsäureester der Formel I sind solche, bei denen R und R1 eine Alkylgruppe mit 1 bis 4 C-Atomen, und x und y 2 oder 3 ist.
- Besonders bevorzugt sind Borsäureester der Formel I, worin R und R1 Methyl, Ethyl, Propyl oder Butyl, und x und y 2 oder 3 ist.
- Die Herstellung der Borsäureester der Formel I - ein Reaktionsprodukt aus Orthoborsäure, Diethylenglykol und einem gemäß Formel I geeigneten Ethylenglykol-monoalkylether im Molverhältnis 1 : 1 : 1 - erfolgt nach an sich bekannten Arbeitsweisen. Die genannten Reaktionskomponenten werden in einem mit Rührer und gegebenenfalls mit Rückflußkühler ausgestattetem Reaktionsgefäß bei einer Temperatur von etwa 50 bis etwa 150 °C, vorzugsweise etwa 110 bis etwa 140 °C, unter Rühren umgesetzt, wobei das entstehende Reaktionswasser kontinuierlich abgeführt wird. Die Umsetzung wird zweckmäßigerweise in Anwesenheit eines inerten, mit Wasser ein Azeotrop bildenden Lösungsmittels, wie beispielsweise Benzol, Toluol, Xylol, Ethylbenzol und dergleichen, durchgeführt. Das Entfernen des Reaktionswassers kann auch dadurch vorgenommen werden, daß man die Umsetzung unter vermindertem Druck, beispielsweise im Wasserstrahlvakuum (7 bis 20 mbar) durchführt. Zur Erzielung einer sehr hohen Ausbeute ist es vorteilhaft, den Ethylenglykolmonoalkylether im Überschuß zu nehmen, die genannten drei Reaktionskomponenten also vorzugsweise in den molaren Gewichtsmengen von etwa 1 : 1 : 1,2 bis 1 : 1 : 2,5 einzusetzen.
- Nach Beendigung der unter kontinuierlicher Wasser-Entfernung durchgeführten Umsetzung wird das gegebenenfalls verwendete Lösungsmittel durch übliche Destillation vom Reaktionsprodukt entfernt und dieses - sofern noch eine weitere Reinigung erforderlich sein sollte - zweckmäßigerweise bei einer Temperatur von 90 bis 150 °C vakuumgestrippt (Druck etwa 7 bis 20 mbar).
- Bei den Ethylenglykol-monoalkylethern der Formel II (Komponente B) kann die Alkylgruppe R2 geradkettig oder verzweigt sein, vorzugsweise ist sie geradkettig.
- Bevorzugte Ethylenglykol-monoalkylether der Formel II sind solche, bei denen R2 Methyl, Ethyl, Propyl oder Butyl, und n 2 bis 4 ist.
- Ein besonders bevorzugter Ethylenglykol-monoalkylether gemäß Formel II ist das Methyltriethylenglykol
- Aus der großen Zahl der möglichen Korrosionsinhibitoren sind die folgenden Verbindungen, einzeln oder in Mischung miteinander, erfindungsgemäß bevorzugt:
- Alkalisalze, vorzugsweise die Natriumsalze der Kohlensäure, der phosphorigen Säure und Phosphorsäure;
- Fettsäuren, vorzugsweise Caprylsäure, Laurinsäure, Palmitinsäure, Stearinsäure und ölsäure;
- Alkalisalze von Fettsäuren, vorzugsweise das Natriumsalz von Laurinsäure, Palmitinsäure, Stearinsäure und ölsäure;
- Ester der phosphorigen Säure und Phosphorsäure mit aliphatischen Alkoholen mit 1 bis 6 C-Atomen, vorzugsweise Ethylphosphat, Dimethylphosphat, Isopropyl-phosphat, Di-isopropyl-phosphat, Butylphosphit und Dimethylphosphit.
- Mono- und Dialkylamine - gegebenenfalls ethoxyliert mit 1 bis 5 Ethylenoxid-Einheiten - und deren Salze mit Mineral- oder Fettsäure, wobei Alkyl eine Gruppe mit 1 bis 18 C-Atomen ist; davon sind bevorzugt: Butylamin, Hexylamin, Octylamin, Isononylamin, Oleylamin, Di--propylamin und Di-butylamin;
- Alkanolamine - gegebenenfalls ethoxyliert mit 1 bis 5 Ethylenoxideinheiten - und deren Salze mit Fettsäuren, wobei Alkyl eine Gruppe mit 1 bis 6 C-Atomen ist; davon sind bevorzugt: Monoethanolamin, Diethanolamin und Triethanolamin;
- Cyclohexylamin; und
- Die Korrosionsinhibitoren werden in der Regel in einer Menge von 1 bis 10 Gew.-%, vorzugsweise von 2 bis 8 Gew.-%, bezogen auf das Gesamtgewicht der Flüssigkeit, eingesetzt.
- Aus der großen Zahl der für hydraulische Flüssigkeiten geeigneten Antioxidantien sind die folgenden Verbindungen, einzeln oder in Mischung miteinander, erfindungsgemäß bevorzugt:
- Alkalisalze der salpetrigen Säure, vorzugsweise Natriumnitrit; phenolische Verbindungen, vorzugsweise Phenyl-a-naphthylamin;
- substituierte Phenole, vorzugsweise Dibutylkresol, 2,6-Dibutyl-p-kresol, 2,6 Di-tert.-butyl-p-kresol und 2,4-Dimethyl-6-tert.-butylphenol;
- Chinone, vorzugsweise Hydrochinone, Brenzchatechine, Anthrachinone und Phenothiazine, die gegebenenfalls kernsubstituiert sind.
- Die Antioxidantien werden in der Regel in einer Menge von 0,01 bis 2,0 Gew.-%, vorzugsweise von 0,05 bis 1,0 Gew.-%, bezogen auf das Gesamtgewicht der Flüssigkeit, eingesetzt.
- Die erfindungsgemäße hydraulische Flüssigkeit enthält vorzugsweise von der Komponente A) 15 bis 20 Gew.-%, von der Komponente B) 55 bis 65 Gew.-% und von der Komponente C) 3 bis 8 Gew.-%, jeweils bezogen auf das Gesamtgewicht der Flüssigkeit.
- Die erfindungsgemäße hydraulische Flüssigkeit kann neben den Komponenten A), B) und C) auch noch D) Dialkyl-polyalkylenglykole der Formel III und/oder E) Polyoxialkylenglykole der Formel IV enthalten. Diese Komponenten können aus Zweckmäßigkeitsgründen zur genauen Einstellung einer gewünschten Viskosität verwendet werden.
- Von den zahlreichen verwendbaren Verbindungen der Formel III haben sich die Alkyl-polyethylenglykol-tert.-butylether als besonders geeignet erwiesen. Bevorzugt eingesetzt werden Alkyl-polyethylenglykol-tert.-butylether der Formel
- Brauchbare Verbindungen der Formel IV sind Polyethylenglykole, Polypropylenglykole und Polybutylenglykole. Bevorzugt verwendbar sind Polyethylenglykole mit einem Molekulargewicht bis zu 200, vorzugsweise von 100 bis 150,insbesondere Diethylenglykol und Triethylenglykol. Der Anteil an Polyoxialkylenglykolen der Formel IV, sofern sie in der erfindungsgemäßen hydraulischen Flüssigkeit eingesetzt werden, liegt bei 0,5 bis 20 Gew.-%, vorzugsweise bei 5 bis 18 Gew.-%, bezogen auf das Gesamtgewicht der Flüssigkeit.
- Die Herstellung der Verbindungen der Formeln II; III und IV gehört seit langem zum Stand der Technik.
- Die Herstellung der erfindungsgemäßen hydraulischen Flüssigkeiten erfolgt durch Zusammenmischen der Komponenten, beispielsweise in einem Behälter mit Rührorgan, wodurch in einfacher Weise ein homogenes Gemisch erhalten wird. In der Regel wird das Zusammenmischen bei Atmosphärendruck und bei Raumtemperatur vorgenommen, es kann gegebenenfalls auch bei höherer Temperatur (30 bis 50 °C) durchgeführt werden, wobei zweckmäßigerweise Feuchtigkeit abgehalten wird.
- Die Erfindung wird durch die nachstehenden Beispiele näher erläutert.
-
- Es wird eine erfindungsgemäße Bremsflüssigkeit durch Mischen der folgenden Komponenten hergestellt:
- Es wird eine erfindungsgemäße Bremsflüssigkeit durch Mischer; der folgenden Komponenten hergestellt:
Triazole, vorzugsweise Benztriazol.
Claims (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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AT80100161T ATE2274T1 (de) | 1979-01-18 | 1980-01-14 | Bremsfluessigkeit fuer motorfahrzeuge. |
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Application Number | Priority Date | Filing Date | Title |
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DE19792901835 DE2901835A1 (de) | 1979-01-18 | 1979-01-18 | Hydraulische fluessigkeiten |
DE2901835 | 1979-01-18 |
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EP0013925A1 true EP0013925A1 (de) | 1980-08-06 |
EP0013925B1 EP0013925B1 (de) | 1983-01-19 |
Family
ID=6060845
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EP80100161A Expired EP0013925B1 (de) | 1979-01-18 | 1980-01-14 | Bremsflüssigkeit für Motorfahrzeuge |
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EP (1) | EP0013925B1 (de) |
JP (1) | JPS5598296A (de) |
AT (1) | ATE2274T1 (de) |
BR (1) | BR8000298A (de) |
CA (1) | CA1137071A (de) |
DE (2) | DE2901835A1 (de) |
MX (1) | MX154414A (de) |
ZA (1) | ZA80291B (de) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0028789A1 (de) * | 1979-11-08 | 1981-05-20 | Hoechst Aktiengesellschaft | Hydraulische Flüssigkeit mit verbesserten Eigenschaften |
US6783693B1 (en) | 1999-04-22 | 2004-08-31 | Basf Aktiengesellschaft | Hydraulic fluids, containing cyclic carboxylic acid derivatives |
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JP5480285B2 (ja) * | 2008-11-07 | 2014-04-23 | ダウ グローバル テクノロジーズ エルエルシー | 低粘度機能性流体 |
CN109468158A (zh) * | 2018-11-15 | 2019-03-15 | 湖北回天新材料股份有限公司 | 一种hzy4机动车辆制动液 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2438038A1 (de) * | 1973-08-11 | 1975-02-20 | Chuo Kagaku Kogyo Kk | Bremsfluessigkeit fuer motorfahrzeuge |
DE2437936A1 (de) * | 1974-08-07 | 1976-02-19 | Basf Ag | Ortho-borsaeureester und deren verwendung als bestandteil von bremsfluessigkeiten |
DE1768933B2 (de) * | 1967-04-13 | 1977-11-10 | OHn Corp, New Haven, Conn. (V-StA.) | Wasserunempfindliche hydraulische fluessigkeiten |
-
1979
- 1979-01-18 DE DE19792901835 patent/DE2901835A1/de not_active Withdrawn
-
1980
- 1980-01-14 AT AT80100161T patent/ATE2274T1/de active
- 1980-01-14 EP EP80100161A patent/EP0013925B1/de not_active Expired
- 1980-01-14 DE DE8080100161T patent/DE3061647D1/de not_active Expired
- 1980-01-17 JP JP315480A patent/JPS5598296A/ja active Granted
- 1980-01-17 BR BR8000298A patent/BR8000298A/pt unknown
- 1980-01-17 CA CA000343853A patent/CA1137071A/en not_active Expired
- 1980-01-17 ZA ZA00800291A patent/ZA80291B/xx unknown
- 1980-01-18 MX MX180870A patent/MX154414A/es unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1768933B2 (de) * | 1967-04-13 | 1977-11-10 | OHn Corp, New Haven, Conn. (V-StA.) | Wasserunempfindliche hydraulische fluessigkeiten |
DE2438038A1 (de) * | 1973-08-11 | 1975-02-20 | Chuo Kagaku Kogyo Kk | Bremsfluessigkeit fuer motorfahrzeuge |
DE2437936A1 (de) * | 1974-08-07 | 1976-02-19 | Basf Ag | Ortho-borsaeureester und deren verwendung als bestandteil von bremsfluessigkeiten |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0028789A1 (de) * | 1979-11-08 | 1981-05-20 | Hoechst Aktiengesellschaft | Hydraulische Flüssigkeit mit verbesserten Eigenschaften |
US6783693B1 (en) | 1999-04-22 | 2004-08-31 | Basf Aktiengesellschaft | Hydraulic fluids, containing cyclic carboxylic acid derivatives |
Also Published As
Publication number | Publication date |
---|---|
DE2901835A1 (de) | 1980-07-31 |
DE3061647D1 (en) | 1983-02-24 |
JPS5598296A (en) | 1980-07-26 |
BR8000298A (pt) | 1980-10-21 |
CA1137071A (en) | 1982-12-07 |
EP0013925B1 (de) | 1983-01-19 |
MX154414A (es) | 1987-08-12 |
ZA80291B (en) | 1981-01-28 |
JPS6252798B2 (de) | 1987-11-06 |
ATE2274T1 (de) | 1983-02-15 |
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