DE2901835A1 - HYDRAULIC LIQUIDS - Google Patents

HYDRAULIC LIQUIDS

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Publication number
DE2901835A1
DE2901835A1 DE19792901835 DE2901835A DE2901835A1 DE 2901835 A1 DE2901835 A1 DE 2901835A1 DE 19792901835 DE19792901835 DE 19792901835 DE 2901835 A DE2901835 A DE 2901835A DE 2901835 A1 DE2901835 A1 DE 2901835A1
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Germany
Prior art keywords
weight
formula
liquid
integer
carbon atoms
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.)
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Application number
DE19792901835
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German (de)
Inventor
Wolfgang Knoblauch
Konrad Von Dipl Chem Dr Werner
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.)
Hoechst AG
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Hoechst AG
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Publication date
Application filed by Hoechst AG filed Critical Hoechst AG
Priority to DE19792901835 priority Critical patent/DE2901835A1/en
Priority to AT80100161T priority patent/ATE2274T1/en
Priority to DE8080100161T priority patent/DE3061647D1/en
Priority to EP80100161A priority patent/EP0013925B1/en
Priority to BR8000298A priority patent/BR8000298A/en
Priority to ZA00800291A priority patent/ZA80291B/en
Priority to CA000343853A priority patent/CA1137071A/en
Priority to JP315480A priority patent/JPS5598296A/en
Priority to MX180870A priority patent/MX154414A/en
Publication of DE2901835A1 publication Critical patent/DE2901835A1/en
Withdrawn legal-status Critical Current

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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
    • 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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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/06—Metal compounds
    • C10M2201/062—Oxides; Hydroxides; Carbonates or bicarbonates
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/085—Phosphorus oxides, acids or salts
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    • C10M2207/02—Hydroxy compounds
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    • C10M2207/02—Hydroxy compounds
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    • C10M2207/025—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with condensed rings
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    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • 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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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • 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
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/044—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms having cycloaliphatic groups
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
    • C10M2215/065—Phenyl-Naphthyl amines
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    • C10M2215/221—Six-membered rings containing nitrogen and carbon only
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    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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    • C10M2215/22—Heterocyclic nitrogen compounds
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
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    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
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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

Abstract

1. Brake fluid for motor vehicles consisting of A) from 10 to 30 % by weight of at least one boric acid ester of the formula I see diagramm : EP0013925,P6,F1 in which R and R1 are alkyl of from 1 to 4 carbon atoms, and x and y are 2 or 3, B) from 50 to 80 % of at least one diluent selected from the group consisting of ethylene glycolmonoalkyl ether of the formula II R2 (OC2 H4 )n -OH in which R2 is alkyl of from 1 to 4 carbon atoms and n is an integer of from 1 to 4, C) 5 to 10 % of at least a further diluent according to formula III see diagramm : EP0013925,P6,F2 in which R3 and R4 are alkyl of from 1 to 4 carbon atoms, R5 is hydrogen or methyl and z is an integer of from 1 to 10, D) 1 to 10 % of at least one inhibitor and E) 5 to 18 % of at least one lubrifiant according to formula IV see diagramm : EP0013925,P6,F3 in which R6 is hydrogen, methyl or ethyl and m is an integer of from 2 to 10, percents by weight relative to the weight of the fluid.

Description

HOECHST AKTIENGESELLSCHAFT HOE 79/F 901 Dr.S/ba Werk GendorfHOECHST AKTIENGESELLSCHAFT HOE 79 / F 901 Dr.S / ba Gendorf plant

Hydraulische FlüssigkeitenHydraulic fluids

Die Erfindung betrifft eine hydraulische Flüssigkeit auf der Basis von Borsäureestern und Ethylenglykol-monoalkylethern The invention relates to a hydraulic fluid based on boric acid esters and ethylene glycol monoalkyl ethers

An hydraulische Flüssigkeiten, insbesondere an Bremsflüssigkeiten, werden hinsichtlich ihrer chemischen und physikalischen 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 Sjafety 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.Hydraulic fluids, especially brake fluids, high demands are placed on their chemical and physical properties. Corresponding the currently existing standards (see specifications DOT 3 and DOT 4 from the US Department of Transportation in Federal Motor Vehicle Sjafety Standard = FMVSS-No. 116 and Specification SAE-J 1703 of the Society of Automotive Engineers, New York), brake fluids should be a special high dry boiling point (reflux boiling point-dry) and Have wet boiling point (reflux boiling point-moist) and have a viscosity that changes only slightly over a wide temperature range.

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 Alky-In the German Auslegeschrift 17 68 933 and in the German Offenlegungsschriften 24 37 936 and 24 38 038 are Brake fluids based on (a) boric acid esters Orthoboric acid, alkylene glycol monoalkyl ethers and / or alkyl

030031/0116030031/0116

lenglykolen, (b) Polyoxalkylenglykol-monoalkylethern und gegebenenfalls (c) Polyoxalkylenglykolen beschrieben. Diese bekannten hydraulischen Flüssigkeiten lassen jedoch "bezüglich der eingangs genannten Anforderungen noch zu wünschen übrig.lenglycols, (b) polyoxalkylene glycol monoalkyl ethers and optionally described (c) polyoxalkylene glycols. However, these known hydraulic fluids "With regard to the requirements mentioned at the beginning, there is still a lot to be desired.

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.It is therefore the object of the invention to create a hydraulic fluid, in particular a brake fluid, which has excellent viscosity and has high dry boiling point and wet boiling point. The new Brake fluid is also supposed to be different To meet requirements in technical use, meet both the DOT 3 and DOT 4 specification.

Die erfindungsgemäße hydraulische Flüssigkeit besteht aus:The hydraulic fluid according to the invention consists of:

A) 10 bis 30 Gew,-%, bezogen auf Gesamtgewicht der Flüssigkeit, von mindestens einem Borsäureester der allgemeinen Formel IA) 10 to 30% by weight, based on the total weight of the Liquid of at least one boric acid ester of the general formula I

OC2H4OC2H4O.OC 2 H 4 OC 2 H 4 O.

R(OC2H4)xO-B B-O(C2H4O) R1 I,R (OC 2 H 4 ) x OB BO (C 2 H 4 O) R 1 I,

^OC2H4OC 2H4O^^ OC 2 H 4 OC 2H 4 O ^

worin bedeuten: R und Ri eine Alkylgruppe mit 1 bis 8 C-Atomen, und χ und y eine ganze Zahl von 1 bis 4,in which: R and Ri are an alkyl group with 1 to 8 Carbon atoms, and χ and y an integer from 1 to 4,

B) 50 bis 80 Gew.-%, bezogen auf das Gesamtgewicht der Flüssigkeit, von mindestens einem Ethylenglykol-monoalkylether der allgemeinen Formel IIB) 50 to 80% by weight, based on the total weight of the liquid, of at least one ethylene glycol monoalkyl ether of the general formula II

R2(OC2H4Jn-OH II,R 2 (OC 2 H 4 J n -OH II,

worin bedeuten: R2 eine Alkylgruppe mit 1 bis 4 C-Atomen und η eine ganze Zahl von 1 bis 4, 35in which: R 2 is an alkyl group having 1 to 4 carbon atoms and η is an integer from 1 to 4.35

C) 1 bis 10 Gew.-%, bezogen auf das Gesamtgewicht der Flüssigkeit, von mindestens einem Inhibitor,C) 1 to 10% by weight, based on the total weight of the liquid, of at least one inhibitor,

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-ri-ri

r-r-

D) O bis 15 Gew.-%, bezogen auf das Gesamtgewicht der Flüssigkeit, von mindestens einer Verbindung der Formel IIID) from 0 to 15% by weight, based on the total weight of the Liquid, of at least one compound of the formula III

R3-(OC2H3) OR4 III,R 3 - (OC 2 H 3 ) OR 4 III,

t.t.

worin bedeuten: R3 und R4 je eine geradkettige oder verzweigte, gesättigte Alkylgruppe mit 1 bis 4 C-Atomen, R5 ein Wasserstoffatom oder eine Methylgruppe und ζ eine ganze Zahl von 1 bis 10 sowiein which: R 3 and R 4 each represent a straight-chain or branched, saturated alkyl group having 1 to 4 carbon atoms, R 5 is a hydrogen atom or a methyl group and ζ is an integer from 1 to 10 and

E) 0 bis 20 Gew.-%, bezogen auf das Gesamtgewicht der Flüssigkeit, von mindestens einer Verbindung der FormelE) 0 to 20% by weight, based on the total weight of the liquid, of at least one compound of the formula

H (OC2H3)mOH IV,H (OC 2 H 3 ) m OH IV,

R6 R 6

worin bedeuten: R6 ein Wasserstoffatom und/oder eine Methylgruppe und/oder eine Ethylgruppe und m eine ganze zahl von 2 bis 10.in which: R 6 is a hydrogen atom and / or a methyl group and / or an ethyl group and m is an integer from 2 to 10.

Bei den Borsäureestern der Formel I (Komponente A) können R und R1, χ und y gleich oder verschieden sein. Die Alkylgruppe R und R-I kann geradkettig oder verzweigt sein, vorzugsweise ist sie geradkettig.In the case of the boric acid esters of the formula I (component A), R and R 1 , χ and y can be identical or different. The alkyl group R and RI can be straight-chain or branched; it is preferably straight-chain.

Bevorzugte Borsäureester der Formel I sind solche, bei denen R und R1 eine Alkylgruppe mit 1 bis 4 C-Atomen, und χ und y 2 oder 3 ist
Besonders bevorzugt sind Borsäureester der Formel I, worin R und R1 Methyl, Ethyl, Propyl oder Butyl, und χ und y 2 oder 3 ist.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 χ and y are 2 or 3
Boric acid esters of the formula I in which R and R 1 are methyl, ethyl, propyl or butyl and χ and y are 2 or 3 are particularly preferred.

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 inThe preparation of the boric acid esters of the formula I - a reaction product from orthoboric acid, diethylene glycol and an ethylene glycol monoalkyl ether suitable according to formula I in Molar ratio 1: 1: 1- takes place according to procedures known per se. The reaction components mentioned are in

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einem mit Rührer und gegebenenfalls mit Rückflußkühler ausgestattetem Reaktionsgefäß bei einer Temperatur von etwa 50 bis etwa 150 0C, vorzugsweise etwa 110 bis etwa 140 0C, 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. a, preferably about, is reacted with a stirrer and optionally equipped with a reflux condenser reaction vessel at a temperature of about 50 to about 150 0 C 110 to about 140 0 C with stirring, wherein the water of reaction formed is continuously removed. The reaction is expediently carried out in the presence of an inert solvent which forms an azeotrope with water, 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). To achieve a very high yield, it is advantageous to take the ethylene glycol monoalkyl ether in excess, ie preferably to use the three reaction components mentioned in molar amounts of about 1: 1: 1.2 to 1: 1: 2.5.

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 0C vakuumgestrippt (Druck etwa 7 bis 20 mbar).After the reaction, carried out with continuous removal of water, the solvent used, if any, is removed from the reaction product by customary distillation and - if further purification should still be necessary - it is expediently vacuum stripped at a temperature of 90 to 150 ° C. (pressure about 7 to 20 ° C) mbar).

Bei den Ethylenglykol-monoalkylethern der Formel II (Komponente B) kann die Alkylgruppe R2 geradkettig oder verzweigt sein, vorzugsweise ist sie geradkettig.In the case of the ethylene glycol monoalkyl ethers of the formula II (component B), the alkyl group R 2 can be straight-chain or branched; it is preferably straight-chain.

Bevorzugte Ethylenglykol-monoalkylether der Formel II sind solche, bei denen R2 Methyl, Ethyl, Propyl oder Butyl, und η 2 bis 4 ist.Preferred ethylene glycol monoalkyl ethers of the formula II are those in which R 2 is methyl, ethyl, propyl or butyl, and η is 2-4.

Ein besonders bevorzugter Ethylenglykol-monoalkylether gemäß Formel II ist das MethyltriethylenglykolA particularly preferred ethylene glycol monoalkyl ether according to formula II is methyl triethylene glycol

CH3(OC2H4J3OH.
35CH 3 (OC 2 H 4 J 3 OH.
35

Als Inhibitor (Komponente C), insbesondere von Korrosion undOxidation (Antioxidanz), können die bei der FormulierungAs an inhibitor (component C), in particular of corrosion and oxidation (antioxidant), the

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von hydraulischen Flüssigkeiten allgemein üblichen Verbindungen eingesetzt werden.of hydraulic fluids commonly used compounds.

Aus der großen Zahl der möglichen Korrosionsinhibitoren sind die folgenden Verbindungen, einzeln oder in Mischung miteinander, erfindungsgemäß bevorzugt:From the large number of possible corrosion inhibitors, the following compounds are available, individually or as a mixture with each other, preferred according to the invention:

Alkalisalze, vorzugsweise die Natriumsalze der Kohlensäure,Alkali salts, preferably the sodium salts of carbonic acid,

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;of phosphorous acid and phosphoric acid; Fatty acids, preferably caprylic acid, lauric acid, palmitic acid, Stearic acid and oleic acid; Alkali salts of fatty acids, preferably the sodium salt of lauric acid, palmitic acid, stearic acid and oleic acid;

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;Esters of phosphorous acid and phosphoric acid with aliphatic alcohols having 1 to 6 carbon atoms, preferably ethyl phosphate, dimethyl phosphate, isopropyl phosphate, diisopropyl phosphate, butyl phosphite and dimethyl phosphite.
Mono- and dialkylamines - optionally ethoxylated with 1 to 5 ethylene oxide units - and their salts with mineral or fatty acids, where alkyl is a group with 1 to 18 carbon atoms; of these are preferred: butylamine, hexylamine, octylamine, isononylamine, oleylamine, di-propylamine and di-butylamine;

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
Triazole, vorzugsweise Benztriazol.Alkanolamines - optionally ethoxylated with 1 to 5 ethylene oxide units - and their salts with fatty acids, where alkyl is a group with 1 to 6 carbon atoms; Of these, preferred are: monoethanolamine, diethanolamine and triethanolamine;
Cyclohexylamine; and
Triazoles, preferably benzotriazole.

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. 35The corrosion inhibitors are generally obtained in an amount from 1 to -10% by weight, preferably from 2 to 8% by weight based on the total weight of the liquid. 35

Aus der großen Zahl der für hydraulische Flüssigkeiten geeigneten Antioxidantien sind die folgenden Verbindungen,Of the large number of antioxidants suitable for hydraulic fluids, the following compounds are

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einzeln oder in Mischung miteinander, erfindungsgemäß bevorzugt:individually or in a mixture with one another, according to the invention preferred:

Alkalisalze der salpetrigen Säure, vorzugsweise Natriumnitrit; phenolische Verbindungen, vorzugsweise, Phenyl-anaphthylamin; Alkali salts of nitrous acid, preferably sodium nitrite; phenolic compounds, preferably phenyl-anaphthylamine;

substituierte Phenole, vorzugsweise Dibutylkresol, 2,6-Dibutyl-p-kresol, 2,6 Di-tert.-butyl-p-kresol und 2,4-Dimethyl-6-tert.-butylphenol; substituted phenols, preferably dibutyl cresol, 2,6-dibutyl-p-cresol, 2,6 di-tert-butyl-p-cresol and 2,4-dimethyl-6-tert-butylphenol;

Chinone, vorzugsweise Hydrochinone, Brenzchatechine, Anthrachinone und Phenothiazine, die gegebenenfalls kernsubstituiert sind.Quinones, preferably hydroquinones, pyrocatechins, anthraquinones and phenothiazines, which are optionally substituted in the nucleus.

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.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.

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.The hydraulic fluid according to the invention preferably contains of component A) 15 to 20% by weight, of component B) 55 to 65% by weight and of component C) 3 to 8% by weight, based in each case on the total weight of the liquid.

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.The hydraulic fluid according to the invention can in addition to components A), B) and C) also include D) dialkyl polyalkylene glycols of the formula III and / or E) contain polyoxyalkylene glycols of the formula IV. These components can can be used for the sake of convenience to precisely set a desired viscosity.

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 FormelOf the numerous compounds of the formula III which can be used, the alkyl polyethylene glycol tert-butyl ethers have been found proved to be particularly suitable. Alkyl polyethylene glycol tert-butyl ethers of the formula are preferably used

/CH3 / CH 3

on R3(OC2H4J7-OC-CH3 on R 3 (OC 2 H 4 J 7 -OC-CH 3

JD Z XCH3 JD ZX CH 3

in der R3 einen geradkettigen oder verzweigten Alkylrestin which R 3 is a straight-chain or branched alkyl radical

0300 3 1/0 1 T60300 3 1/0 1 T6

mit 1 bis 4 C-Atomen bedeutet und ζ eine ganze Zahl von 2 bis 10 / vorzugsweise 2 bis 5 ist. Diese Polyethylenglykoldiether sind in der deutschen Offenlegungsschrift 23 50 569 beschrieben. Der Anteil an Verbindungen der Formel III, sofern sie in der erfindungsgemäßen hydraulischen Flüssigkeit eingesetzt werden, liegt bei 0,5 bis 15 Gew.-%, vorzugsweise bei 5 bis 10 Gew.-%, bezogen auf das Gesamtgewicht der Flüssigkeit.with 1 to 4 carbon atoms and ζ is an integer of 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, if 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 liquid.

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.Compounds of the formula IV which can be used are polyethylene glycols, Polypropylene glycols and polybutylene glycols. Polyethylene glycols with a molecular weight can preferably be used up to 200, preferably from 100 to 150, in particular diethylene glycol and triethylene glycol.

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.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 wt .-%, preferably at 5 to 18% by weight, based on the total weight of the liquid.

Die Herstellung der Verbindungen der Formeln II; III und IV gehört seit langem zum Stand der Technik.The preparation of the compounds of the formulas II; III and IV have long been state of the art.

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.The preparation of the hydraulic fluids according to the invention takes place by mixing the components together, for example in a container with a stirrer, whereby a homogeneous mixture is obtained in a simple manner.

In der Regel wird das Zusammenmischen bei Atmosphärendruck und bei Raumtemperatur vorgenommen, es kann gegebenenfalls auch bei höherer Temperatur (30 bis 50 0C) durchgeführt werden, wobei zweckmäßigerweise Feuchtigkeit abgehalten wird.As a rule, 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.), in which case moisture is expediently kept away.

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Die Erfindung wird durch die nachstehenden Beispiele näher erläutert.The invention is illustrated in more detail by the following examples.

Als Borsäureester (Komponente A) werden die nachstehenden Verbindungen eingesetzt:The following compounds are used as boric acid esters (component A):

^)C2H4OC2H4O.^) C 2 H 4 OC 2 H 4 O.

CH3(OC2H4)2O-B B-O(C2H4O),CH3 CH 3 (OC 2 H 4 ) 2O-B BO (C 2 H 4 O), CH 3

.OC2H4OC2H4O.OC 2 H 4 OC 2 H 4 O

CH3(OC2H4)3O-B B-O(C2H4O)3CH3 CH 3 (OC 2 H 4 ) 3 O-B BO (C 2 H 4 O) 3 CH 3

3' DC2H4OC2H4O 3 'DC 2 H 4 OC 2 H 4 O

CH3 (CH2)2CH2(OC2H4)20-B B-O(C2H4O)2CH2 CCH2)2CH3 CH 3 (CH 2 ) 2 CH 2 (OC 2 H 4 ) 2 0-B BO (C 2 H 4 O) 2 CH 2 CCH 2 ) 2 CH 3

OC2H4OC2H4OOC 2 H 4 OC 2 H 4 O

Beispiel 1example 1

Es wird eine erfindungsgemäße Bremsflüssigkeit durch Mischen der folgenden Komponenten hergestellt:It becomes a brake fluid according to the invention by mixing made of the following components:

Gew.-% Komponente A: Borsäureester 2) 19,0% By weight of component A: boric acid ester 2) 19.0

Komponente B: Triethylenglykol-monomethylether 75,4 30Component B: triethylene glycol monomethyl ether 75.4 30

Komponente C: ölsäure 0,1Component C: oleic acid 0.1

Caprylamin + 2 EO 5,4Caprylamine + 2 EO 5.4

Di-isopropyl-phosphat 0,05Diisopropyl phosphate 0.05

Phenyl-a-naphthylamin 0,1 35Phenyl-a-naphthylamine 0.1 35

Diese Bremsflüssigkeit besitzt die folgenden Eigenschaften,This brake fluid has the following properties,

gemessen nach FMVSS Nr. 116 für DOT 3- und DOT 4-Bremsflüssigkeiten: 030031/0116 measured according to FMVSS No. 116 for DOT 3 and DOT 4 brake fluids: 030031/0116

Trocken-Siedepunkt:
Naß-Siedepunkt:
Viskosität bei -40 0C:Dry boiling point:
Wet boiling point:
Viscosity at -40 0 C:

Gummiquellung 72 h/120 0C Bodendurchme s se rRubber swelling 72 h / 120 0 C bottom diameter

4t-4t-

258 0C
172 0C
705 miti2/s258 0 C
172 0 C
705 with i 2 / s

+ 0,6 mm.+ 0.6 mm.

Zum Vergleich seien nachstehend die Forderungen für eine DOT 3-Bremsflüssigkeit und eine DOT 4-Bremsflüssigkeit angegeben:For comparison, the following are the requirements for a DOT 3 brake fluid and a DOT 4 brake fluid specified:

FMVSS 116FMVSS 116

Trocken-Siedepunkt
Naß-Siedepunkt
Viskosität bei -40 0CDry boiling point
Wet boiling point
Viscosity at -40 0 C.

DOT 3DOT 3

mind. 205 °Cat least 205 ° C

mind. 140 0Cat least 140 0 C

max. 1500 mm2/smax. 1500 mm 2 / s

DOT 4DOT 4

mind. 230 0C mind. 155 0C max.1800 mm2/sat least 230 0 C at least 155 0 C max 1800 mm 2 / s

Gummiquellung 72 h/120 0C: +0,15 bisRubber swelling 72 h / 120 0 C: +0.15 to

Bodendurchmesser +0,15 bis +1,4 mm +1,4 mm.Bottom diameter +0.15 to +1.4 mm +1.4 mm.

Beispiel 2Example 2

Es wird eine erfindungsgemäße Bremsflüssigkeit durch Mischen der folgenden Komponenten hergestellt:It becomes a brake fluid according to the invention by mixing made of the following components:

Komponente A: Borsäureester 3)Component A: boric acid ester 3)

Komponente B: Triethylenglykol-monomethyletherComponent B: triethylene glycol monomethyl ether

Komponente C: Caprylamin.+ 2 EOComponent C: caprylamine. + 2 EO

ölsäure Dephenylamin-Derivatoleic acid dephenylamine derivative

Gew.-? 30,0Weight? 30.0

64,464.4

5,4 0,1 0,15.4 0.1 0.1

Diese Bremsflüssigkeit besitzt die folgenden Eigenschaften:This brake fluid has the following properties:

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254254 0C 0 C 167167 0C 0 C 960960 mm2 /smm 2 / s 1313th ,7 mm2/s, 7 mm 2 / s + O+ O , 7 mm, 7 mm 88th ,6, 6

Trocken-S iedepunkt Naß-Siedepunkt Viskosität bei -4 0 0C Viskosität bei 20 0CDry boiling point Wet boiling point Viscosity at -4 0 0 C Viscosity at 20 0 C

Gummiquellung 72 h/120 0C BodendurchmesserRubber swell 72 h / 120 0 C base diameter

pH (nach SAE-J 1703pH (according to SAE-J 1703

10 Beispiel 3 „10 Example 3 "

^ Gew.-%^% By weight

Komponente A: Borsäureester 1) 15,0Component A: boric acid ester 1) 15.0

Komponente B: Tr ie thy le.nglykolmonome thy lether 64,4Component B: Trie thy le.nglykolmonome thy lether 64.4

Komponente C: n-Butylaminoxethylat 3,5Component C: n-butylamine oxyethylate 3.5

1 ς Phenyl-a-naphthylamin ,0,11 ς phenyl-a-naphthylamine, 0.1

Komponente E: Triethylenglykol 17,0Component E: triethylene glycol 17.0

Trocken-Siedepunkt Naß-Siedepunkt Viskosität -40 0C Viskosität 100 0CDry boiling point Wet boiling point Viscosity -40 0 C Viscosity 100 0 C

Gummiquellung 70 h/120 0C BodendurchmesserRubber swell 70 h / 120 0 C base diameter

pH (nach SAE)pH (according to SAE)

Beispiel 4Example 4

Komponente A: Borsäureester 2)Component A: boric acid ester 2)

Komponente B: TriethylenglykolmonomethyletherComponent B: triethylene glycol monomethyl ether

Di-triethylenglykolmonobutyletherDi-triethylene glycol monobutyl ether

Komponente C: n-Butylaminoxethylat CaprylaminoleatComponent C: n-butylamine oxyethylate caprylamine oleate

Benztriazol Phenyl-a-naphthylaminBenztriazole Phenyl-a-naphthylamine

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246246 OO CC. mm2 /smm 2 / s 171171 OO CC. mmmm 12521252 mm2 /smm 2 / s 2,2, 11 + 0,+ 0, 33 8,8th, 11

GewWeight - Q.
• ti- Q.
• ti 2121st ,3, 3 4949 ,1,1 8,8th, 88th 4,4, 33 0,0, 22 0,0, 22 0,0, 11

- γ- - γ-

260260 0C 0 C 174174 0C 0 C 13601360 mm2/seemm 2 / see 22 ,4 mm2/see, 4 mm 2 / see + 0+ 0 ,7 mm, 7 mm 88th ,0, 0

Gew.-%Wt%

Komponente D: Methyltetraethylenglykol-Component D: methyl tetraethylene glycol

tert.-butylether 7,0tert-butyl ether 7.0

Komponente E: Polyethylenglykol 200 5,0Component E: polyethylene glycol 200 5.0

Diethylenglykol 4,0Diethylene glycol 4.0

Trocken-Siedepunkt
Naß-Siedepunkt
Viskosität - 40 0C
Viskosität 100 0CDry boiling point
Wet boiling point
Viscosity - 40 0 C
Viscosity 100 0 C

. Gummiquellung 70 h/120 0C
Bodendurchmesser. Rubber swell 70 h / 120 0 C.
Bottom diameter

pH (nach SAE)pH (according to SAE)

Die Beispiele zeigen, daß die erfindungsgemäße hydraulische Flüssigkeit, die ganz spezielle Borsäureester der Formel I und Alkylenglykolmonoalkylether der Formel II in einer quantitativ spezifischen Menge enthält, in den entscheidenden Eigenschaften, nämlich Viskosität, Trocken-Siedepunkt und Naß-Siedepunkt, hervorragende Werte besitzen. Darüberhinaus sind die für einen technischen Einsatz besonders wichtigen Werte bezüglich Gummiquellung überraschend gut. Die erfindungsgemäßen v/asserunempfindlichen hydraulischen Flüssigkeiten eignen sich vor allem für hydraulische Bremssysteme, vorzugsweise von Motorfahrzeugen, für hydraulische Steuersysteme und hydraulische Transmissionen.The examples show that the hydraulic Liquid, the very special boric acid ester of the formula I and alkylene glycol monoalkyl ether of the formula II in one contains quantitatively specific amount, in the decisive properties, namely viscosity, dry boiling point and wet boiling point, have excellent values. In addition, they are special for technical use important values regarding rubber swelling are surprisingly good. The inventive water-insensitive hydraulic Liquids are particularly suitable for hydraulic brake systems, preferably of motor vehicles, for hydraulic control systems and hydraulic transmissions.

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Claims (3)

Patentansprüche HOE 79/F 901Claims HOE 79 / F 901 1. Hydraulische Flüssigkeit im wesentlichen bestehend aus1. Essentially consisting of hydraulic fluid the end A) 10 bis 30 Gew.-%, bezogen auf Gesamtgewicht der Flüssigkeit, von mindestens einem Borsäureester der allgemeinen Formel IA) 10 to 30% by weight, based on the total weight of the liquid, of at least one boric acid ester of the general formula I. .OC2H4OC2H4O.
R(OC2H4)XO-B^ B-O(C2H4O)7R1 I,.OC 2 H 4 OC 2 H 4 O.
R (OC 2 H 4 ) X OB ^ BO (C 2 H 4 O) 7 R 1 I, ^OC2H4OC2H4CT
10^ OC 2 H 4 OC 2 H 4 CT
10 worin bedeuten:R und Ri eine Alkylgruppe mit 1 bis 8 C-Atomen und χ und y eine ganze Zahl von Y bis 4,in which: R and Ri are an alkyl group with 1 to 8 carbon atoms and χ and y are an integer from Y to 4, B) 50 bis 80 Gew.-%, bezogen auf das Gesamtgewicht der Flüssigkeit, von mindestens einem Ethylenglykol-monoalkylether der allgemeinen Formel II,B) 50 to 80% by weight, based on the total weight of the liquid, of at least one ethylene glycol monoalkyl ether of the general formula II, R2(OC2Hi)n-OH II/R 2 (OC 2 Hi) n -OH II / worin bedeuten R2 eine Alkylgruppe mit 1 bis 4 C-Atomen und η eine ganze Zahl von 1 bis 4,where R 2 is an alkyl group with 1 to 4 carbon atoms and η is an integer from 1 to 4, C) 1 bis 10 Gew.-%, bezogen auf das Gesamtgewicht der Flüssigkeit von mindestens einem Inhibitor,C) 1 to 10% by weight, based on the total weight of the Liquid of at least one inhibitor, D) 0 bis 15 Gew.-%, bezogen auf das Gesamtgewicht der Flüssigkeit von mindestens einer Verbindung der Formel D) 0 to 15% by weight, based on the total weight of the liquid, of at least one compound of the formula R3-(OC2H3) -OR4 IIIR 3 - (OC 2 H 3 ) -OR 4 III i Z
30 i Z
30th worin bedeuten : R3 und R4 je eine geradkettige oder verzweigte, gesättigte Alkylgruppe mit 1 bis 4 C-Atomen, R5 ein Wasserstoffatom oder eine Methylgruppe und ζ eine ganze Zahl von 1 bis 10 sowiein which: R 3 and R 4 each represent a straight-chain or branched, saturated alkyl group having 1 to 4 carbon atoms, R5 is a hydrogen atom or a methyl group and ζ is an integer from 1 to 10 and 030031/0116030031/0116 E) O bis 20 Gew.-%, bezogen auf das Gesamtgewicht der Flüssigkeit, von mindestens einer Verbindung der FormelE) 0 to 20 wt .-%, based on the total weight of the Liquid, of at least one compound of the formula H(OC2H3)mOH IV,H (OC 2 H 3 ) m OH IV, R6 R 6 worin bedeuten: R6 ein Wasserstoffatom und/oder eine Methylgruppe und/oder eine Ethylgruppe und m eine ganze Zahl von 2 bis 10.in which: R 6 is a hydrogen atom and / or a methyl group and / or an ethyl group and m is an integer from 2 to 10. 2. Hydraulische Flüssigkeit nach Anspruch 1, dadurch gekennzeichnet, daß sie als Komponente2. Hydraulic fluid according to claim 1, characterized characterized as being a component D) 0,5 bis 15 Gew.-%, bezogen auf das Gesamtgewicht der Flüssigkeit, Alkyl-polyethylenglykol-tert.-butylether der FormelD) 0.5 to 15% by weight, based on the total weight of the Liquid, alkyl polyethylene glycol tert-butyl ether the formula ,CH3 , CH 3 R3(OC2H4) -OC-CH3
Z \R 3 (OC 2 H 4 ) -OC-CH 3
Z \ enthält, in der R3 einen geradkettigen oder verzweigten Alkylrest mit 1 bis 4 C-Atomen bedeutet, und ζ eine ganze Zahl von 2 bis 10 ist.contains, in which R 3 is a straight-chain or branched alkyl radical having 1 to 4 carbon atoms, and ζ is an integer from 2 to 10. 3. Hydraulische Flüssigkeit nach Anspruch 1, dadurch gekennzeichnet, daß sie als Komponente3. Hydraulic fluid according to claim 1, characterized in that that they are as a component E) 0,5 bis 20 Gew.-%, bezogen auf das Gesamtgewicht der Flüssigkeit, Polyoxethylenglykole mit einem Molekulargewicht von 100 bis 200 enthält.E) 0.5 to 20% by weight, based on the total weight of the Liquid containing polyethylene glycols with a molecular weight of 100 to 200. 030031/01 16030031/01 16
DE19792901835 1979-01-18 1979-01-18 HYDRAULIC LIQUIDS Withdrawn DE2901835A1 (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
DE19792901835 DE2901835A1 (en) 1979-01-18 1979-01-18 HYDRAULIC LIQUIDS
AT80100161T ATE2274T1 (en) 1979-01-18 1980-01-14 BRAKE FLUID FOR MOTOR VEHICLES.
DE8080100161T DE3061647D1 (en) 1979-01-18 1980-01-14 Brake fluids for motor vehicles
EP80100161A EP0013925B1 (en) 1979-01-18 1980-01-14 Brake fluids for motor vehicles
BR8000298A BR8000298A (en) 1979-01-18 1980-01-17 HYDRAULIC LIQUID
ZA00800291A ZA80291B (en) 1979-01-18 1980-01-17 Hydraulic fluids
CA000343853A CA1137071A (en) 1979-01-18 1980-01-17 Hydraulic fluids
JP315480A JPS5598296A (en) 1979-01-18 1980-01-17 Hydraulic liquid
MX180870A MX154414A (en) 1979-01-18 1980-01-18 IMPROVED HYDRAULIC LIQUID COMPOSITION

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19792901835 DE2901835A1 (en) 1979-01-18 1979-01-18 HYDRAULIC LIQUIDS

Publications (1)

Publication Number Publication Date
DE2901835A1 true DE2901835A1 (en) 1980-07-31

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ID=6060845

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DE19792901835 Withdrawn DE2901835A1 (en) 1979-01-18 1979-01-18 HYDRAULIC LIQUIDS
DE8080100161T Expired DE3061647D1 (en) 1979-01-18 1980-01-14 Brake fluids for motor vehicles

Family Applications After (1)

Application Number Title Priority Date Filing Date
DE8080100161T Expired DE3061647D1 (en) 1979-01-18 1980-01-14 Brake fluids for motor vehicles

Country Status (8)

Country Link
EP (1) EP0013925B1 (en)
JP (1) JPS5598296A (en)
AT (1) ATE2274T1 (en)
BR (1) BR8000298A (en)
CA (1) CA1137071A (en)
DE (2) DE2901835A1 (en)
MX (1) MX154414A (en)
ZA (1) ZA80291B (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2945094A1 (en) * 1979-11-08 1981-05-21 Hoechst Ag, 6000 Frankfurt HYDRAULIC LIQUID WITH IMPROVED PROPERTIES
DE19918199A1 (en) 1999-04-22 2000-10-26 Basf Ag Hydraulic fluid, especially motor vehicle brake fluid, contains one or more cyclic esters or amides of carboxylic acids, e.g. N-methyl-pyrrolidone
BRPI0916028A2 (en) * 2008-11-07 2015-11-10 Dow Global Technologies Inc fluid composition
CN109468158A (en) * 2018-11-15 2019-03-15 湖北回天新材料股份有限公司 A kind of HZY4 motor vehicle brake liquid

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3637794A (en) * 1967-04-13 1972-01-25 Olin Mathieson Borate esters prepared by successive reactions of boric acid with glycol monoethers and polyols
JPS5046584A (en) * 1973-08-11 1975-04-25
DE2437936C2 (en) * 1974-08-07 1983-02-10 Basf Ag, 6700 Ludwigshafen Cyclic orthoboric acid esters and their use as a component of brake fluids

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Publication number Publication date
BR8000298A (en) 1980-10-21
MX154414A (en) 1987-08-12
EP0013925A1 (en) 1980-08-06
ZA80291B (en) 1981-01-28
DE3061647D1 (en) 1983-02-24
CA1137071A (en) 1982-12-07
JPS5598296A (en) 1980-07-26
ATE2274T1 (en) 1983-02-15
EP0013925B1 (en) 1983-01-19
JPS6252798B2 (en) 1987-11-06

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