EP0454110B1 - Fluids based on glycol compounds, for metal corrosion inhibiting brakes - Google Patents
Fluids based on glycol compounds, for metal corrosion inhibiting brakes Download PDFInfo
- Publication number
- EP0454110B1 EP0454110B1 EP91106665A EP91106665A EP0454110B1 EP 0454110 B1 EP0454110 B1 EP 0454110B1 EP 91106665 A EP91106665 A EP 91106665A EP 91106665 A EP91106665 A EP 91106665A EP 0454110 B1 EP0454110 B1 EP 0454110B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- glycol
- formula
- alkyl
- component
- weight
- 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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- 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
- C10M2227/062—Cyclic esters
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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
- 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
- C10M2227/062—Cyclic esters
- C10M2227/0625—Cyclic esters used as base material
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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
- 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
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- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/02—Groups 1 or 11
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- 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
- Preferred monocarboxylic acids and their alkali metal salts are the C5 to C18 monocarboxylic acids (fatty acids) and their sodium salts, such as caprylic acid, lauric acid, stearic acid and oleic acid.
- Preferred dicarboxylic acids and their alkali metal salts are those of the formula HOOC- (CH2) 4 ⁇ 10-COOH and their sodium salts, such as adipic acid, suberic acid, azelaic acid and sebacic acid.
- Preferred antioxidative aromatic compounds are those from the group of phenols, bisphenols, cresols, quinolines and naphthylamines, such as phenol, bisphenol A, 2,4-dimethyl-6-tert-butylphenol, styrene-modified phenol, 2,6-dimethyl-p- cresol, diphenylamine, phenyl- ⁇ -naphthylamine, styrenated diphenylamine, 4,4'-dioctyl-diphenylamine and polymeric 2,2,4-trimethyl-1,2-dihydroquinoline.
- Preferred monohydric alcohols are therefore those of the formula 8 below wherein R15 is H or CH3, preferably H, R16 is a preferably straight-chain alkyl radical having 1 to 12 carbon atoms, preferably 1 to 6 carbon atoms, and e is 0 to 15, preferably 0 to 8.
- component A) essentially consists of the specified glycol compounds from the group of glycols, glycol monoalkyl ethers and glycol dialkyl ethers, which are used in such a ratio that the desired brake fluid type is obtained.
- component A) essentially consists of the specified glycol compounds from the group of glycol and glycol monoalkyl boric acid esters, glycol monoalkyl ethers, glycol dialkyl ethers, glycols and glycol formals, which in turn are used in such a ratio that the desired brake fluid type is obtained.
- Composition 2 is a composition of Composition 2:
- Composition 4 is a composition having Composition 4:
- composition 6 is a composition of Composition 6:
- the invention is explained in more detail using examples and comparative examples.
- the percentages given in the examples and comparative examples are percentages by weight, and the individual brake fluids were prepared by mixing the specified components at room temperature.
- the brake fluids of the examples and comparative examples were tested for boiling point (dry boiling point), wet boiling point, viscosity at -40 ° C. and tin corrosion.
- the boiling point, wet boiling point and the viscosity at -40 ° C. were determined exactly in accordance with FMVSS No. 116.
- the tin corrosion was also determined in accordance with FMVSS No.
Description
Die Erfindung betrifft eine gegen Metallkorrosion inhibierte Bremsflüssigkeit, bestehend im wesentlichen aus mindestens einer Glykolverbindung als Hauptkomponente und mindestens einem Inhibitor für Flüssigkeiten auf der Basis von Glykolverbindungen.The invention relates to a brake fluid inhibited against metal corrosion, consisting essentially of at least one glycol compound as the main component and at least one inhibitor for liquids based on glycol compounds.
Die derzeit in Gebrauch befindlichen Bremsflüssigkeiten gehören bekanntlich zu den Typen DOT 3, DOT 4 und DOT 5 (DOT = Department of Transportation, USA). Die Eigenschaftsanforderungen für diese Flüssigkeiten sind in U. S. Federal Motor Vehicle Safety Standard 116 (FMVSS Nr. 116) und in U. S. Society of Automotive Engineers J 1703 (SAE J 1703) angegeben. Zu den wichtigen Eigenschaften einer Bremsflüssigkeit zählen bekanntlich der Trockensiedepunkt (auch Rückflußsiedepunkt-trocken oder einfach Siedepunkt genannt), der Naßsiedepunkt (auch Rückflußsiedepunkt-naß genannt) und die Viskosität bei -40 °C. Nachstehend sind die diesbezüglich geforderten Werte zusammengefaßt:
Es sind bereits eine Reihe von Bremsflüssigkeiten beschrieben, zum Beispiel in der britischen Patentschrift 850,990 und in den US-Patentschriften 3,711,411, 3,972,822, 4,088,590 und 4,371,448, die im wesentlichen aus mindestens einer Glykolverbindung als Hauptkomponente und mindestens einem Korrosionsinhibitor für Flüssigkeiten auf der Basis von Glykolverbindungen bestehen. Diese Bremsflüssigkeiten erfüllen mehr oder weniger gut die angegebenen Forderungen bezüglich Siedepunkt, Naßsiedepunkt und Viskosität bei -40 °C. Sie sind auch gegenüber einer Reihe von Metallen/Konstruktionsmaterialien korrosionsinhibiert, gegenüber dem Metall Zinn lassen sie aber hinsichtlich Korrosionsverhalten zu wünschen übrig. Der Mangel eines derartigen Korrosionsschutzes stellt ferner deswegen ein Problem dar, weil Bremsflüssigkeiten häufig in verzinnten Behältern abgefüllt und gelagert werden. Im Hinblick darauf sollte also eine auch gegen Zinnkorrosion besonders wirkungsvoll geschützte Bremsflüssigkeit zur Verfügung stehen.A number of brake fluids have already been described, for example in British patent specification 850,990 and in US Patents 3,711,411, 3,972,822, 4,088,590 and 4,371,448, which essentially consist of at least one glycol compound as the main component and at least one corrosion inhibitor for liquids based on glycol compounds consist. These brake fluids more or less meet the stated requirements regarding boiling point, wet boiling point and viscosity at -40 ° C. They are also corrosion-inhibited against a number of metals / construction materials, but against the metal tin they leave something to be desired in terms of corrosion behavior. The lack of such corrosion protection is also a problem because brake fluids are often filled and stored in tinned containers. With this in mind, a brake fluid that is particularly effective against tin corrosion should also be available.
Die Aufgabe der Erfindung besteht demnach darin, eine Bremsflüssigkeit zu schaffen, die sowohl die genannten Standardeigenschaften als auch eine gute Korrosionsinhibierung gegenüber den üblichen Metallen und gleichzeitig gegenüber Zinn aufweist. Die neue Bremsflüssigkeit soll also im Trockensiedepunkt, Naßsiedepunkt und in der Viskosität bei -40 °C den Typen DOT 3, DOT 4 und DOT 5 entsprechen und gerade im Hinblick auf das Metall Zinn besonders hoch antikorrosiv ausgerüstet sein.The object of the invention is therefore to provide a brake fluid which has both the standard properties mentioned and good corrosion inhibition compared to the usual metals and at the same time to tin. The new brake fluid should therefore correspond to types DOT 3, DOT 4 and DOT 5 in dry boiling point, wet boiling point and in viscosity at -40 ° C and should be particularly highly anticorrosive, especially with regard to tin.
Die erfindungsgemäße Bremsflüssigkeit besteht im wesentlichen aus
- A) mindestens einer Glykolverbindung als Hauptkomponente,
- B) mindestens einem Inhibitor für Flüssigkeiten auf der Basis von Glykolverbindungen und
- C) 0,005 bis 0,5 Gew.-%, vorzugsweise 0,01 bis 0,1 Gew.-%, Gewichtsprozente bezogen auf das Gewicht der (fertigen) Bremsflüssigkeit, von einem Gemisch saurer Phosphorsäureester (als zusätzlichem Inhibitor), das im wesentlichen aus Mono- und Diphosphorsäureestern besteht und erhalten worden ist durch Umsetzung von einer Phosphor enthaltenden Verbindung mit einem einwertigen Alkohol und einem Polyol.
- A) at least one glycol compound as the main component,
- B) at least one inhibitor for liquids based on glycol compounds and
- C) 0.005 to 0.5% by weight, preferably 0.01 to 0.1% by weight, percentages by weight based on the weight of the (finished) brake fluid, of a mixture of acidic phosphoric acid esters (as an additional inhibitor) which essentially consists of mono- and diphosphoric acid esters and has been obtained by reacting a phosphorus-containing compound with a monohydric alcohol and a polyol.
Die vorliegende Erfindung beruht auf der überraschenden Feststellung, daß durch Inkorporierung des speziellen Phosphorsäureesterproduktes gemäß Komponente C) in bekannte Bremsflüssigkeiten auf der Basis von Glykolverbindungen eine unerwartet hohe Korrosionsinhibierung gerade beim Metall Zinn erreicht wird, und zwar unabhängig von der Art der Basisverbindungen, die zur Gruppe der Glykole, deren Mono- und Diether, Glykolformale, Glykolborsäureester und dergleichen gehören können. Durch den Zusatz der Komponente C) wird offensichtlich ein spezieller Synergismus erhalten, der aus der Kombination der Komponente C) und den in der Flüssigkeit bereits befindlichen Inhibitoren resultieren dürfte. Mit dieser Kombination wird überraschenderweise gerade für das Metall Zinn ein hervorragender Korrosionsschutz erreicht und auch die Inhibierung gegenüber den üblichen Metallen, wie Gußeisen und Stahl, Kupfer, Aluminium, Zink und dergleichen, entspricht den derzeitigen Forderungen. Bremsflüssigkeiten auf der Basis von Glykolverbindungen mit Phosphorsäureestern verschiedener Art in Kombination mit üblichen Korrosionsinhibitoren, wie Alkylaminen, Alkanolaminen, Alkalimetallsalzen von anorganischen oder organischen Säuren, Triazolen und dergleichen, sind schon seit langem bekannt (vergleiche die eingangs genannten Druckschriften). Diese Bremsflüssigkeiten des Typs DOT 3, DOT 4 und DOT 5 weisen zwar einen relativ guten Korrosionsschutz gegenüber den üblichen Metallen auf, gegenüber Zinn lassen sie aber zu wünschen übrig. Es ist deshalb in der Tat überraschend, daß mit Hilfe des Phosphorsäureesterproduktes gemäß Komponente C) ein hoch antikorrosives Verhalten gerade gegen Zinn erhalten wird.The present invention is based on the surprising finding that by incorporating the special phosphoric acid ester product according to component C) into known brake fluids based on glycol compounds, an unexpectedly high corrosion inhibition is achieved, particularly in the case of metal tin, regardless of the type of basic compounds belonging to the group the glycols, their mono- and diethers, glycol formals, glycol boric acid esters and the like may include. The addition of component C) obviously results in a special synergism which should result from the combination of component C) and the inhibitors already present in the liquid. This combination surprisingly provides excellent corrosion protection, especially for the metal tin, and also the inhibition against the usual metals, such as cast iron and steel, copper, aluminum, zinc and the like, corresponds to the current requirements. Brake fluids based on glycol compounds with phosphoric acid esters of various types in combination with conventional corrosion inhibitors, such as alkylamines, alkanolamines, alkali metal salts of inorganic or organic acids, triazoles and the like, have been known for a long time (compare the publications mentioned at the outset). These brake fluids of the types DOT 3, DOT 4 and DOT 5 do have a relatively good corrosion protection against the usual metals, compared to tin, however, they leave something to be desired. It is therefore surprising, in fact, that with the aid of the phosphoric acid ester product according to component C), a highly anticorrosive behavior is obtained, especially against tin.
Die Komponente A) der erfindungsgemäßen Bremsflüssigkeit besteht aus einer oder mehreren Glykolverbindungen und bildet die Hauptkomponente der Flüssigkeit. Als Glykolverbindungen können all jene eingesetzt werden, die üblicherweise die Basis für die in Rede stehenden Bremsflüssigkeiten bilden (vergleiche die eingangs genannten Druckschriften). Es handelt sich in der Regel um die bekannten Glykolverbindungen aus der Gruppe der Glykole, Glykolmonoalkylether, Glykoldialkylether, Glykolformale, Glykolborsäureester und Glykolmonoalkylborsäureester.
Bevorzugte Glykole sind solche der nachstehenden Formel 1
worin R¹ H oder CH₃ ist und in der Polyalkoxylenkette auch H und CH₃ ist (damit soll ausgedrückt sein, daß R¹ innerhalb der Kette des Polyalkoxylenrestes auch die beiden genannten Bedeutungen annehmen kann), vorzugsweise H, und x 1 bis 8 ist, vorzugsweise 2 bis 5. Beispiele für Glykole sind Monoethylenglykol, Diethylenglykol, Triethylenglykol, Tetraethylenglykol und weitere Polyoxethylenglykole mit einem Molekulargewicht von bis zu 400 sowie die entsprechenden Propylenglykole und Mischoxalkylate, wobei die Ethylenglykole bevorzugt sind.Component A) of the brake fluid according to the invention consists of one or more glycol compounds and forms the main component of the fluid. All those that normally form the basis for the brake fluids in question can be used as glycol compounds (compare the publications mentioned at the beginning). These are generally the known glycol compounds from the group of glycols, glycol monoalkyl ethers, glycol dialkyl ethers, glycol formals, glycol boric acid esters and glycol monoalkyl boric acid esters.
Preferred glycols are those of formula 1 below
wherein R¹ is H or CH₃ and in the polyalkoxylene chain is also H and CH₃ (this is to say that R¹ within the chain of the polyalkoxylene radical can also take on the two meanings mentioned), preferably H, and x is 1 to 8, preferably 2 to 5. Examples of glycols are monoethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol and other polyoxethylene glycols with a molecular weight of up to 400 as well as the corresponding propylene glycols and mixed oxyalkylates, with the ethylene glycols being preferred.
Bevorzugte Glykolmonoalkylether sind solche der nachstehenden Formel 2
worin R² H oder CH₃ ist und in der Polyalkoxylenkette auch H und CH₃ ist, vorzugsweise H, R³ C₁ bis C₄-Alkyl und y 1 bis 6 ist, vorzugsweise 2 bis 4. Beispiele für Glykolmonoether sind Diethylenglykolmonomethylether, Triethylenglykolmonomethylether, Tetraethylenglykolmonomethylether, Diethylenglykolmonoisopropylether, Diethylenglykolmonobutylether, Triethylenglykolmonobutylether, Tetraethylenglykolmonoethylether und die entsprechenden Propylenglykolether und Mischoxalkylat-Derivate, wobei die Ethylenglykolether bevorzugt sind.Preferred glycol monoalkyl ethers are those of formula 2 below
wherein R² is H or CH₃ and in the polyalkoxylene chain is also H and CH₃, preferably H, R³ is C₁ to C₄-alkyl and y is 1 to 6, preferably 2 to 4. Examples of glycol monoethers are diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, tetraethylene glycol monomethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoisopropyl ether, , Triethylene glycol monobutyl ether, tetraethylene glycol monoethyl ether and the corresponding propylene glycol ether and mixed oxyalkylate derivatives, the ethylene glycol ether being preferred.
Bevorzugte Glykoldialkylether sind solche der nachstehenden Formel 3
worin R⁴ H oder CH₃ ist und in der Polyalkoxylenkette auch H und CH₃ ist, vorzugsweise H, R⁵ C₁ bis C₄-Alkyl, R⁶ C₁ bis C₄-Alkyl und z 1 bis 6 ist, vorzugsweise 2 bis 4. Beispiele für Glykoldiether sind Diethylenglykoldimethylether, Diethylenglykoldibutylether, Triethylenglykoldimethylether, Triethylenglykoldiisopropylether, Triethylenglykolmethylisopropylether, Tetraethylenglykoldimethylether, Tetraethylenglykoldiisopropylether und Tetraethylenglykoldibutylether und die entsprechenden Propylenglykolether und Mischoxalkylat-Derivate, wobei die Ethylenglykolether bevorzugt sind.Preferred glycol dialkyl ethers are those of formula 3 below
wherein R⁴ is H or CH₃ and in the polyalkoxylene chain is also H and CH₃, preferably H, R⁵ C₁ to C₄-alkyl, R⁶ C₁ to C₄-alkyl and z is 1 to 6, preferably 2 to 4. Examples of glycol diethers are diethylene glycol dimethyl ether, Diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol diisopropyl ether, triethylene glycol methyl isopropyl ether, tetraethylene glycol dimethyl ether, tetraethylene glycol diisopropyl ether and tetraethylene glycol dibutyl ether and the corresponding propylene glycol ethers and mixed oxyalkylate derivatives are preferred, wherein the ethylene oxide derivatives are preferred.
Bevorzugte Glykolformale sind solche der nachstehenden Formel 4
R⁷O-(CH₂CH₂O)m-CH₂-(OCH₂CH₂)n-OR⁸ (4)
worin R⁷ C₁ bis C₄-Alkyl ist, R⁸ C₁ bis C₄-Alkyl, m 1 bis 4 und n 1 bis 4 ist. Besonders bevorzugte Bis-(ethylenglykolmonoalkylether)-formale der Formel 4 sind solche, wenn R⁷ und R⁸ CH₃ sind und m jeweils 2 oder 3 ist, wobei m = n ist.Preferred glycol formals are those of Formula 4 below
R⁷O- (CH₂CH₂O) m -CH₂- (OCH₂CH₂) n -OR⁸ (4)
wherein R⁷ is C₁ to C₄ alkyl, R⁸ C₁ to C₄ alkyl, m is 1 to 4 and n is 1 to 4. Particularly preferred bis (ethylene glycol monoalkyl ether) formals of the formula 4 are those when R⁷ and R⁸ are CH₃ and m is in each case 2 or 3, where m = n.
Bevorzugte Glykolborsäureester und Glykolmonoalkyletherborsäureester sind solche der nachstehenden Formeln 5 und 6
[R⁹O-(CH₂CH₂O)a]₃-B (5)
worin R⁹ C₁ bis C₄-Alkyl ist und a 1 bis 6 ist, vorzugsweise 2 bis 4,
worin R¹⁰ und R¹¹ C₁ bis C₄-Alkyl sind und b und c jeweils 1 bis 6 ist, vorzugsweise 1 bis 4. Besonders bevorzugte Borsäureester der Formeln 5 und 6 sind solche, wenn R⁹ CH₃ ist und a 2, 3 oder 4 ist; R¹⁰ und R¹¹ CH₃ sind und b und c jeweils 2, 3 oder 4 ist.Preferred glycol boric acid esters and glycol monoalkyl ether boric acid esters are those of the formulas 5 and 6 below
[R⁹O- (CH₂CH₂O) a ] ₃-B (5)
wherein R⁹ is C₁ to C₄ alkyl and a is 1 to 6, preferably 2 to 4,
wherein R¹⁰ and R¹¹ are C₁ to C₄ alkyl and b and c are each 1 to 6, preferably 1 to 4. Particularly preferred boric acid esters of formulas 5 and 6 are those when R⁹ is CH₃ and a is 2, 3 or 4; R¹⁰ and R¹¹ are CH₃ and b and c are each 2, 3 or 4.
Die Komponente B) der erfindungsgemäßen Bremsflüssigkeit besteht aus einer oder mehreren Verbindungen, die üblicherweise als Inhibitoren in Flüssigkeiten auf der Basis von Glykolen und/oder Glykolderivaten eingesetzt werden (vergleiche die eingangs genannten Druckschriften). Es handelt sich in der Regel um die bekannten Inhibitorverbindungen aus der Gruppe der Alkylamine, Cycloalkylamine, Alkanolamine, Monocarbonsäuren und deren Alkalimetallsalze, Dicarbonsäuren und deren Alkalimetallsalze, Alkalimetallsalze der Kohlensäure, Phosphorsäure und Molybdänsäure, Triazole, Imidazole und der antioxidativen aromatischen Verbindungen. Bevorzugte Alkylamine sind Mono-, Di- und Trialkylamine mit 1 bis 18 C-Atomen, vorzugsweise 3 bis 8 C-Atomen, in jeder Alkylgruppe, wie Butylamin, Hexylamin, Octylamin, Isononylamin, Isotridecylamin, Oleylamin, Diisopropylamin, Dioctylamin, Tributylamin, Trihexylamin und Dimethyloctylamin. Das bevorzugte Cycloalkylamin ist Cyclohexylamin.Component B) of the brake fluid according to the invention consists of one or more compounds which are usually used as inhibitors in fluids based on glycols and / or glycol derivatives (compare the documents mentioned at the outset). These are generally the known inhibitor compounds from the group of alkylamines, cycloalkylamines, alkanolamines, monocarboxylic acids and their alkali metal salts, dicarboxylic acids and their Alkali metal salts, alkali metal salts of carbonic acid, phosphoric acid and molybdic acid, triazoles, imidazoles and the antioxidative aromatic compounds. Preferred alkylamines are mono-, di- and trialkylamines having 1 to 18 carbon atoms, preferably 3 to 8 carbon atoms, in each alkyl group, such as butylamine, hexylamine, octylamine, isononylamine, isotridecylamine, oleylamine, diisopropylamine, dioctylamine, tributylamine, trihexylamine and dimethyloctylamine. The preferred cycloalkylamine is cyclohexylamine.
Bevorzugte Alkanolamine sind solche der nachstehenden Formel 7
worin R¹² H oder CH₃ ist, d 0, 1 oder 2 ist, vorzugsweise 0, R¹³ H, C₁ bis C₁₈-Alkyl, vorzugsweise C₁ bis C₈-Alkyl, oder ein Rest der Formel
ist, worin R¹² und d die angegebenen Bedeutungen haben, und R¹⁴ eine der Bedeutungen von R¹³ hat, wie Ethanolamin, Methyldiethanolamin, Isopropanolamin, Diethanolamin, Diisopropanolamin, Butyldiethanolamin, Octyldiethanolamin, Triethanolamin und Triisopropanolamin.Preferred alkanolamines are those of formula 7 below
wherein R¹² is H or CH₃, d is 0, 1 or 2, preferably 0, R¹³ H, C₁ to C₁₈ alkyl, preferably C₁ to C₈ alkyl, or a radical of the formula
is where R¹² and d have the meanings given, and R¹⁴ has one of the meanings of R¹³, such as ethanolamine, methyldiethanolamine, isopropanolamine, diethanolamine, diisopropanolamine, butyldiethanolamine, octyldiethanolamine, triethanolamine and triisopropanolamine.
Bevorzugte Monocarbonsäuren und deren Alkalimetallsalze sind die C₅ bis C₁₈-Monocarbonsäuren (Fettsäuren) und deren Natriumsalze, wie Caprylsäure, Laurinsäure, Stearinsäure und Ölsäure.Preferred monocarboxylic acids and their alkali metal salts are the C₅ to C₁₈ monocarboxylic acids (fatty acids) and their sodium salts, such as caprylic acid, lauric acid, stearic acid and oleic acid.
Bevorzugte Dicarbonsäuren und deren Alkalimetallsalze sind solche der Formel HOOC-(CH₂)₄₋₁₀-COOH und deren Natriumsalze, wie Adipinsäure, Suberinsäure, Azelainsäure und Sebacinsäure.Preferred dicarboxylic acids and their alkali metal salts are those of the formula HOOC- (CH₂) ₄₋₁₀-COOH and their sodium salts, such as adipic acid, suberic acid, azelaic acid and sebacic acid.
Bevorzugte Alkalimetallsalze der Kohlensäure, Phosphorsäure und Molybdänsäure sind Natriumcarbonat, Natriumphosphat und Natriummolybdat (Na₂MoO₄).Preferred alkali metal salts of carbonic acid, phosphoric acid and molybdic acid are sodium carbonate, sodium phosphate and sodium molybdate (Na₂MoO₄).
Bevorzugte Triazole und Imidazole sind Benzotriazol (auch als 1 H-Benzotriazol oder 1,2,3-Benzotriazol bezeichnet), Tolyltriazol (in der Regel ein Isomerengemisch) und Benzimidazol.Preferred triazoles and imidazoles are benzotriazole (also referred to as 1 H-benzotriazole or 1,2,3-benzotriazole), tolyltriazole (usually a mixture of isomers) and benzimidazole.
Bevorzugte antioxidative aromatische Verbindungen sind solche aus der Gruppe der Phenole, Bisphenole, Kresole, Chinoline und Naphthylamine, wie Phenol, Bisphenol A, 2,4-Dimethyl-6-tert.-butylphenol, styrolmodifiziertes Phenol, 2,6-Dimethyl-p-kresol, Diphenylamin, Phenyl-α-naphthylamin, styrolisiertes Diphenylamin, 4,4'-Dioctyl-diphenylamin und polymeres 2,2,4-Trimethyl-1,2-dihydrochinolin.Preferred antioxidative aromatic compounds are those from the group of phenols, bisphenols, cresols, quinolines and naphthylamines, such as phenol, bisphenol A, 2,4-dimethyl-6-tert-butylphenol, styrene-modified phenol, 2,6-dimethyl-p- cresol, diphenylamine, phenyl-α-naphthylamine, styrenated diphenylamine, 4,4'-dioctyl-diphenylamine and polymeric 2,2,4-trimethyl-1,2-dihydroquinoline.
Die Komponente B) liegt im allgemeinen in einer Menge von 0,1 bis 10 Gew.-% vor, vorzugsweise in einer Menge von 0,5 bis 8 Gew.-%, Gewichtsprozente bezogen auf das Gewicht der (fertigen) Bremsflüssigkeit.
Die Komponente B) besteht in der Regel aus einem oder mehreren der obengenannten Inhibitoren. Sie besteht vorzugsweise aus einem der genannten Alkylamine oder Alkanolamine oder einem Alkylamin und einem Alkanolamin und aus einer der genannten Triazolverbindungen, wobei das Alkylamin und/oder das Alkanolamin die Hauptmenge ausmacht, während das Triazol in einer vergleichsweise geringen Menge vorliegt. Die Komponente B) besteht demnach vorzugsweise aus 0,5 bis 8 Gew.-%, vorzugsweise 0,5 bis 6 Gew.-%, von einem der genannten Alkylamine und/oder Alkanolamine, wobei die Alkanolamine bevorzugt sind, und 0,01 bis 0,5 Gew.-%, vorzugsweise 0,05 bis 0,3 Gew.-%, von einer der genannten Triazolverbindungen, Gewichtsprozente bezogen auf das Gewicht der Bremsflüssigkeit.Component B) is generally present in an amount of 0.1 to 10% by weight, preferably in an amount of 0.5 to 8% by weight, percentages by weight based on the weight of the (finished) brake fluid.
Component B) generally consists of one or more of the inhibitors mentioned above. It preferably consists of one of the alkylamines or alkanolamines mentioned or an alkylamine and an alkanolamine and one of the triazole compounds mentioned, the alkylamine and / or the alkanolamine making up the majority, while the triazole is present in a comparatively small amount. Component B) accordingly preferably consists of 0.5 to 8% by weight, preferably 0.5 to 6% by weight, of one of the alkylamines and / or alkanolamines mentioned, the alkanolamines being preferred, and 0.01 to 0.5% by weight, preferably 0.05 to 0.3% by weight, of one of the triazole compounds mentioned, percentages by weight based on the weight of the brake fluid.
Die Komponente C) der erfindungsgemäßen Bremsflüssigkeit ist ein Gemisch von sauren Phosphorsäureestern. Es besteht also im wesentlichen aus Phosphorsäuremonoestern und Phosphorsäurediestern. Phosphorsäuretriester liegen, wenn überhaupt, nur in einer sehr geringen Menge vor. Ein weiteres Merkmal des Phosphorsäureesterproduktes liegt darin, daß zur Veresterung mit der Ausgangsphosphorverbindung sowohl ein einwertiger Alkohol als auch ein Polyol eingesetzt wird. Um den sauren Charakter des Phosphorsäureesterproduktes zu erhalten, werden die drei Reaktionskomponenten klarerweise in einem solchen Molverhältnis eingesetzt, daß im wesentlichen nur primäre und sekundäre Phosphorsäureester gebildet werden. Die Säurezahl des Phosphorsäureestergemisches liegt im allgemeinen bei 300 bis 700, vorzugsweise 350 bis 600 (die Bestimmung der Säurezahl erfolgt nach der bekannten Methode, das heißt durch Titration mit NaOH-Lösung bis zum zweiten Wendepunkt der Titrationskurve und Umrechnung des NaOH-Verbrauches in mg KOH pro g Produkt).Component C) of the brake fluid according to the invention is a mixture of acidic phosphoric acid esters. It essentially consists of phosphoric acid monoesters and phosphoric acid diesters. If at all, phosphoric acid triesters are only present in a very small amount. Another feature of the phosphoric acid ester product is that both a monohydric alcohol and a polyol are used for the esterification with the starting phosphorus compound. In order to maintain the acidic character of the phosphoric acid ester product, the three reaction components are clearly used in such a molar ratio that essentially only primary and secondary phosphoric acid esters are formed. The acid number of the phosphoric acid ester mixture is generally 300 to 700, preferably 350 to 600 (the acid number is determined by the known method, that is to say by titration with NaOH solution up to the second turning point of the titration curve and conversion of the NaOH consumption into mg KOH per g of product).
Geeignete Phosphorverbindungen sind zum Beispiel Phosphorsäure (H₃PO₄), Phosphortrichlorid (PCl₃), Phosphorpentachlorid (PCl₅) und Phosphorpentoxid (P₄O₁₀). Unter den möglichen Phosphorverbindungen ist Phosphorpentoxid bevorzugt, weil bei Einsatz dieser Verbindung die relativ zeitraubende Entfernung des bei der Veresterung entstehenden Reaktionswassers oder HCl entfällt.Suitable phosphorus compounds are, for example, phosphoric acid (H₃PO₄), phosphorus trichloride (PCl₃), phosphorus pentachloride (PCl₅) and phosphorus pentoxide (P₄O₁₀). Among the possible phosphorus compounds, phosphorus pentoxide is preferred because when this compound is used, the relatively time-consuming removal of the water of reaction or HCl formed during the esterification is eliminated.
Geeignete einwertige Alkohole sind solche aus der Gruppe der Alkanole und oxalkylierten Alkanole. Als einwertige Alkohole werden bevorzugt eingesetzt C₁ bis C₁₂-Alkanole, vorzugsweise C₁ bis C₆-Alkanole (geradkettig oder verzweigt), oder deren Oxethylate und Oxpropylate, vorzugsweise Oxethylate, mit 1 bis 15 Oxalkyleneinheiten, vorzugsweise 1 bis 8 Oxalkyleneinheiten. Bevorzugte einwertige Alkohole sind also solche der nachstehenden Formel 8
worin R¹⁵ H oder CH₃ ist, vorzugsweise H, R¹⁶ ein vorzugsweise geradkettiger Alkylrest mit 1 bis 12 C-Atomen, vorzugsweise 1 bis 6 C-Atomen, und e 0 bis 15 ist, vorzugsweise 0 bis 8. Als Vertreter von einwertigen Alkoholen seien im einzelnen genannt Methanol, Ethanol, Propanol, Isopropanol, n-Butanol, Isobutanol, n-Amylalkohol, Isoamylalkohol, n-Hexanol, Isononylalkohol, n-Decanol, Laurylalkohol und Isotridecylalkohol sowie deren Oxpropylate, vorzugsweise Oxethylate, mit 1 bis 15 Oxalkyleneinheiten, vorzugsweise 1 bis 8 Oxalkyleneinheiten.Suitable monohydric alcohols are those from the group of alkanols and alkoxylated alkanols. As a mono Alcohols are preferably used C₁ to C₁₂ alkanols, preferably C₁ to C₆ alkanols (straight-chain or branched), or their oxethylates and oxpropylates, preferably oxethylates, with 1 to 15 oxalkylene units, preferably 1 to 8 oxalkylene units. Preferred monohydric alcohols are therefore those of the formula 8 below
wherein R¹⁵ is H or CH₃, preferably H, R¹⁶ is a preferably straight-chain alkyl radical having 1 to 12 carbon atoms, preferably 1 to 6 carbon atoms, and e is 0 to 15, preferably 0 to 8. As representatives of monohydric alcohols are im called methanol, ethanol, propanol, isopropanol, n-butanol, isobutanol, n-amyl alcohol, isoamyl alcohol, n-hexanol, isononyl alcohol, n-decanol, lauryl alcohol and isotridecyl alcohol and their oxpropylates, preferably oxethylates, with 1 to 15 oxalkylene units, preferably 1 up to 8 oxalkylene units.
Geeignete Polyole sind solche aus der Gruppe der Alkandiole, Alkantriole, Alkantetrole, Pentite und Hexite, wie Ethandiol (Ethylenglykol), Propandiol-1,2, Propandiol-1,3, Butandiol-1,2, Butandiol-1,3, Butandiol-1,4, Pentandiol und Hexandiol, Diethylenglykol, Triethylenglykol, Tetraethylenglykol und Pentaethylenglykol sowie die entsprechenden Propylenglykole, Glycerin, Trimethylolpropan, Trimethylolethan, Erythrit und Pentaerythrit, wobei Diole und Triole bevorzugt sind. Besonders bevorzugte Polyole sind die Alkandiole der nachstehenden Formel 9
HO-(CH₂)f-OH (9)
worin f 2 bis 8 ist, vorzugsweise 2 bis 5 (das sind Alkylenglykole), und der nachstehenden Formel 10
worin R¹⁷ H oder CH₃ ist, vorzugsweise H, und g 1 bis 10 ist, vorzugsweise 1 bis 5 (das sind Oxalkylenglykole).Suitable polyols are those from the group of the alkanediols, alkanetriols, alkanetretrols, pentites and hexites, such as ethanediol (ethylene glycol), 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, butanediol- 1,4, pentanediol and hexanediol, diethylene glycol, triethylene glycol, tetraethylene glycol and pentaethylene glycol and the corresponding propylene glycols, glycerol, trimethylolpropane, trimethylolethane, erythritol and pentaerythritol, with diols and triols being preferred. Particularly preferred polyols are the alkanediols of formula 9 below
HO- (CH₂) f -OH (9)
wherein f is 2 to 8, preferably 2 to 5 (these are alkylene glycols), and Formula 10 below
wherein R¹⁷ is H or CH₃, preferably H, and g is 1 to 10, preferably 1 to 5 (these are oxalkylene glycols).
Die Komponente C) der erfindungsgemäßen Bremsflüssigkeit ist vorzugsweise ein Phosphorsäureesterprodukt gemäß US-Patentschrift 4,141,938 und gemäß europäischer Patentschrift 28 674-B1, auf die hier bezug genommen wird. Ein bevorzugtes saures Phosphorsäureestergemisch ist demnach ein solches, das erhalten worden ist durch Umsetzung von Phosphor-V-oxid mit einem Gemisch, bestehend aus einem einwertigen Alkohol und einem Alkanpolyol mit 2 bis 12 C-Atomen und 2 bis 6 Hydroxylgruppen, bevorzugt unter Einhaltung eines Molverhältnisses von Phosphor-V-oxid : einwertigem Alkohol : Alkanpolyol von 1 : 2 : 4/n', wobei n' die Anzahl der Hydroxylgruppen im Alkanpolyolmolekül bedeutet, oder eines stöchiometrischen Überschusses der alkoholischen Komponenten, wobei die Reaktionskomponenten bei einer Temperatur von etwa 0 bis 120 °C unter Ausschluß von Feuchtigkeit und in Gegenwart eines inerten Gases etwa 1 bis 6 Stunden lang gerührt oder geknetet werden. Im Falle eines einwertigen Alkohols und eines Alkandiols beträgt also das Molverhältnis von Phosphor-V-oxid : einwertigem Alkohol : Alkandiol 1 : 2 : 2 und im Falle eines Alkantetrols als Alkanpolyol 1 : 2 : 1. Es hat sich als vorteilhaft erwiesen, wenn man die Umsetzung des Phosphor-V-oxids mit dem einwertigen Alkohol und dem Alkanpolyol in der exothermen Phase der Reaktion - durch Kühlen des Reaktionsgemisches - bei einer Temperatur von 0 bis 70 °C, vorzugsweise 20 bis 60 °C, und in der Endphase der Reaktion - durch Erwärmen des Reaktionsgemisches - bei einer Temperatur von 80 bis 100 °C durchführt. Dabei empfiehlt sich die Anwendung eines Inertgases, wie zum Beispiel Stickstoff. Im allgemeinen ist die Umsetzung innerhalb von 1 bis 3 Stunden beendet, was durch das Ausbleiben der bei der anfänglich exothermen Reaktion entstehenden Reaktionswärme angezeigt wird. Nach Beendigung der Reaktion und Abkühlen des Reaktionsgemisches liegt das angestrebte Gemisch saurer Phosphorsäureester vor. Wie bereits oben erwähnt, stellen die einwertigen Alkohole der Formel 8 und die Alkandiole der Formeln 9 und 10 neben Phosphorpentoxid die bevorzugten Reaktionspartner zur Herstellung der Komponente C) dar.Component C) of the brake fluid according to the invention is preferably a phosphoric acid ester product according to US Pat. No. 4,141,938 and according to European Pat. No. 28,674-B1, to which reference is made here. A preferred acidic phosphoric ester mixture is accordingly one which has been obtained by reacting phosphorus V-oxide with a mixture consisting of a monohydric alcohol and an alkane polyol having 2 to 12 carbon atoms and 2 to 6 hydroxyl groups, preferably while observing one Molar ratio of phosphorus V-oxide: monohydric alcohol: alkane polyol of 1: 2: 4 / n ', where n' is the number of hydroxyl groups in the alkane polyol molecule, or a stoichiometric excess of the alcoholic components, the reaction components being at a temperature of about 0 to 120 ° C with exclusion of moisture and in the presence of an inert gas for about 1 to 6 hours stirred or kneaded. In the case of a monohydric alcohol and an alkanediol, the molar ratio of phosphorus V-oxide: monohydric alcohol: alkanediol is 1: 2: 2 and in the case of an alkane tetrol as an alkane polyol 1: 2: 1. It has proven to be advantageous if the reaction of the phosphorus V-oxide with the monohydric alcohol and the alkane polyol in the exothermic phase of the reaction - by cooling the reaction mixture - at a temperature of 0 to 70 ° C, preferably 20 to 60 ° C, and in the Final phase of the reaction - by heating the reaction mixture - at a temperature of 80 to 100 ° C. The use of an inert gas such as nitrogen is recommended. In general, the reaction is complete within 1 to 3 hours, which is indicated by the absence of the heat of reaction which arises in the initially exothermic reaction. After the reaction has ended and the reaction mixture has cooled, the desired mixture of acidic phosphoric acid esters is present. As already mentioned above, the monohydric alcohols of the formula 8 and the alkanediols of the formulas 9 and 10, in addition to phosphorus pentoxide, are the preferred reactants for the preparation of component C).
Wie aus den obigen Ausführungen hervorgeht, sind die charakteristischen Merkmale der erfindungsgemäßen Bremsflüssigkeit ihr Inhibitorsystem gemäß den Komponenten B) und C) und die Unabhängigkeit des Inhibitorsystems von der Komponente A), das heißt, für die Wirkung des Inhibitorsystems ist die Art der Komponente A) im einzelnen nicht kritisch. Die Komponente A) bestimmt bekanntlich den Typ, zu dem die Bremsflüssigkeit gehört, das heißt, es liegt praktisch allein an der Komponente A), ob eine Bremsflüssigkeit bezüglich der eingangs genannten Eigenschaften, das sind Trockensiedepunkt, Naßsiedepunkt und Viskosität, zu den derzeit gebräuchlichen Typen DOT 3, DOT 4 und/oder DOT 5 gehört. Der Effekt des Inhibitorsystems gemäß den Komponenten B) und C) zeigt sich also in all diesen an sich bekannten Bremsflüssigkeitstypen. Was die Komponente A) im einzelnen betrifft, sind bekanntlich zwei Varianten bevorzugt. Nach der einen Variante besteht die Komponente A) im wesentlichen aus den angegebenen Glykolverbindungen aus der Gruppe der Glykole, Glykolmonoalkylether und Glykoldialkylether, die in einem solchen Verhältnis eingesetzt werden, daß der angestrebte Bremsflüssigkeitstyp erhalten wird. Nach der zweiten Variante besteht die Komponente A) im wesentlichen aus den angegebenen Glykolverbindungen aus der Gruppe der Glykol- und Glykolmonoalkylborsäureester, Glykolmonoalkylether, Glykoldialkylether, Glykole und Glykolformale, die wiederum in einem solchen Verhältnis eingesetzt werden, daß der angestrebte Bremsflüssigkeitstyp erhalten wird. Nachstehend seien einige typische Zusammensetzungen der Komponente A) angegeben, wie sie im Stand der Technik beschrieben und in den genannten Bremsflüssigkeitstypen vorliegen, wobei die einzelnen Bestandteile mit A₁, A₂ und A₃ bezeichnet werden und die angegebenen Gewichtsprozente sich auf die Gewichtssumme aus A₁, A₂ und A₃ beziehen.As can be seen from the above explanations, the characteristic features of the brake fluid according to the invention are its inhibitor system according to components B) and C) and the independence of the inhibitor system from component A), that is to say for the action of the inhibitor system the type of component A) not critical in detail. As is known, component A) determines the type to which the brake fluid belongs, i.e. it is practically solely due to component A) whether a brake fluid is one of the types currently used with regard to the properties mentioned at the outset, i.e. dry boiling point, wet boiling point and viscosity DOT 3, DOT 4 and / or DOT 5 belongs. The effect of the inhibitor system according to components B) and C) is thus evident in all of these brake fluid types known per se. As far as component A) is concerned, two variants are known to be preferred. According to one variant, component A) essentially consists of the specified glycol compounds from the group of glycols, glycol monoalkyl ethers and glycol dialkyl ethers, which are used in such a ratio that the desired brake fluid type is obtained. According to the second variant, component A) essentially consists of the specified glycol compounds from the group of glycol and glycol monoalkyl boric acid esters, glycol monoalkyl ethers, glycol dialkyl ethers, glycols and glycol formals, which in turn are used in such a ratio that the desired brake fluid type is obtained. Some typical compositions of component A) are described below, as described in the prior art and in the brake fluid types mentioned, the individual constituents being denoted by A₁, A₂ and A₃ and the percentages by weight given based on the total weight of A₁, A₂ and A₃ refer.
- A₁) 30 bis 80 %A₁) 30 to 80%
- Glykole vom Molekulargewicht bis zu 300, wobei die Menge an Glykol mit einem Molekulargewicht von mehr als 150 mindestens 20 Gew.-% beträgt, undGlycols of molecular weight up to 300, the amount of glycol with a molecular weight of more than 150 being at least 20% by weight, and
- A₂) 20 bis 70 %A₂) 20 to 70%
- Glykolmonoalkylether und/oder GlykoldialkyletherGlycol monoalkyl ether and / or glycol dialkyl ether
- A₁) 40 bis 50 %A₁) 40 to 50%
- Glykole vom Molekulargewicht bis zu 200 undGlycols from molecular weight up to 200 and
- A₂) 50 bis 60 %A₂) 50 to 60%
- GlykolmonoalkyletherGlycol monoalkyl ether
- A₁) 50 bis 70 %A₁) 50 to 70%
- Glykole vom Molekulargewicht bis zu 200 undGlycols from molecular weight up to 200 and
- A₂) 30 bis 50 %A₂) 30 to 50%
- GlykoldialkyletherGlycol dialkyl ether
- A₁) 30 bis 50 %A₁) 30 to 50%
- Glykole vom Molekulargewicht 150 bis 300,Glycols with a molecular weight of 150 to 300,
- A₂) 20 bis 50 %A₂) 20 to 50%
- Glykolmonoalkylether undGlycol monoalkyl ether and
- A₃) 10 bis 20 %A₃) 10 to 20%
- GlykoldialkyletherGlycol dialkyl ether
- A₁) 40 bis 95 %A₁) 40 to 95%
- Borsäureester von Glykolen und/oder Glykolmonoalkylethern undBoric acid esters of glycols and / or glycol monoalkyl ethers and
- A₂) 5 bis 60 %A₂) 5 to 60%
- Glykolmonoalkylether und/oder GlykoldialkyletherGlycol monoalkyl ether and / or glycol dialkyl ether
- A₁) 40 bis 90 %A₁) 40 to 90%
- Borsäureester von Glykolen und/oder Glykolmonoalkylethern,Boric acid esters of glycols and / or glycol monoalkyl ethers,
- A₂) 5 bis 50 %A₂) 5 to 50%
- Glykolmonoalkylether und/oder Glykoldialkylether undGlycol monoalkyl ether and / or glycol dialkyl ether and
- A₃) 2 bis 10 %A₃) 2 to 10%
- Glykole vom Molekulargewicht 150 bis 300Glycols with a molecular weight of 150 to 300
- A₁) 10 bis 50 %A₁) 10 to 50%
- Borsäureester von Glykolen und/oder Glykolmonoalkylethern undBoric acid esters of glycols and / or glycol monoalkyl ethers and
- A₂) 50 bis 90 %A₂) 50 to 90%
- GlykolmonoalkyletherGlycol monoalkyl ether
- A₁) 10 bis 20 %A₁) 10 to 20%
- Borsäureester von Glykolmonoalkylethern,Boric acid esters of glycol monoalkyl ethers,
- A₂) 40 bis 60 %A₂) 40 to 60%
- Glykolmonoalkylether undGlycol monoalkyl ether and
- A₃) 15 bis 45 %A₃) 15 to 45%
- Glykole vom Molekulargewicht 150 bis 300Glycols with a molecular weight of 150 to 300
- A₁) 20 bis 40 %A₁) 20 to 40%
- Borsäureester von Glykolen und Glykolmonoalkylethern,Boric acid esters of glycols and glycol monoalkyl ethers,
- A₂) 30 bis 60 %A₂) 30 to 60%
- Glykolmonoalkylether undGlycol monoalkyl ether and
- A₃) 10 bis 40 %A₃) 10 to 40%
- Bis-(ethylenglykolmonoalkylether)-formaleBis (ethylene glycol monoalkyl ether) formal
Die Herstellung der erfindungsgemäßen Bremsflüssigkeiten 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 durchgeführt, wobei zweckmäßigerweise Feuchtigkeit abgehalten wird. Das Zusammenmischen kann auch bei höherer Temperatur durchgeführt werden, beispielsweise bei 30 bis 50 °C.The brake fluids according to the invention are produced by mixing the components together, for example in a container with a stirring element, as a result of which a homogeneous mixture is obtained in a simple manner. As a rule, the mixing is carried out at atmospheric pressure and at room temperature, it being expedient to keep moisture away. Mixing can also be carried out at a higher temperature, for example at 30 to 50 ° C.
Die erfindungsgemäßen Bremsflüssigkeiten eignen sich vor allem für hydraulische Bremssysteme, vorzugsweise von solchen in Motorfahrzeugen.The brake fluids according to the invention are particularly suitable for hydraulic brake systems, preferably those in motor vehicles.
Die Erfindung wird an Beispielen und Vergleichsbeispielen noch näher erläutert.
Die in den Beispielen und Vergleichsbeispielen angegebenen Prozentwerte sind Gewichtsprozente, und die einzelnen Bremsflüssigkeiten wurden durch Mischen der angegebenen Komponenten bei Raumtemperatur hergestellt. Die Bremsflüssigkeiten der Beispiele und Vergleichsbeispiele wurden bezüglich Siedepunkt (Trockensiedepunkt), Naßsiedepunkt, Viskosität bei -40 °C und Zinnkorrosion getestet. Die Bestimmung des Siedepunktes, Naßsiedepunktes und der Viskosität bei -40 °C erfolgte genau nach FMVSS Nr. 116. Die Bestimmung der Zinnkorrosion erfolgte ebenfalls nach FMVSS Nr. 116, wobei jedoch zusätzlich eine Verschärfung des Testes gewählt wurde, indem die im Test vorgesehene Zugabe von 5 Vol.-% Wasser zur Bremsflüssigkeitsprobe nicht vorgenommen wurde; es wurde also, ebenso wie bei der technischen Verwendung, die Bremsflüssigkeit als solche eingesetzt. Bekanntlich wird ein Wassergehalt von bis zu 5 Vol.-% oft erst nach mehrjährigem Gebrauch der Bremsflüssigkeit erreicht.The invention is explained in more detail using examples and comparative examples.
The percentages given in the examples and comparative examples are percentages by weight, and the individual brake fluids were prepared by mixing the specified components at room temperature. The brake fluids of the examples and comparative examples were tested for boiling point (dry boiling point), wet boiling point, viscosity at -40 ° C. and tin corrosion. The boiling point, wet boiling point and the viscosity at -40 ° C. were determined exactly in accordance with FMVSS No. 116. The tin corrosion was also determined in accordance with FMVSS No. 116, although the test was additionally tightened by adding the addition provided for in the test of 5% by volume of water for the brake fluid sample was not carried out; So, just like in technical use, the brake fluid was used as such. As is known, a water content of up to 5% by volume is often only achieved after the brake fluid has been used for several years.
-
A)
- 42,00 %
- Triethylenglykol
- 22,10 %
- Diethylenglykolmonomethylether
- 35,00 %
- Triethylenglykolmono-n-butylether
- 42.00%
- Triethylene glycol
- 22.10%
- Diethylene glycol monomethyl ether
- 35.00%
- Triethylene glycol mono-n-butyl ether
-
B)
- 0,80 %
- Diisopropanolamin
- 0,05 %
- Tolyltriazol
- 0.80%
- Diisopropanolamine
- 0.05%
- Tolyltriazole
-
C)
- 0,05 %
- von einem sauren Phosphorsäureestergemisch, das wie nachstehend beschrieben hergestellt worden ist.
- 0.05%
- of an acidic mixture of phosphoric acid esters prepared as described below.
- Siedepunktboiling point
- 235 °C235 ° C
- NaßsiedepunktWet boiling point
- 147 °C147 ° C
- Viskositätviscosity
- 1 284 mm²/s1 284 mm² / s
- ZinnkorrosionTin corrosion
- ±0 mg/cm²± 0 mg / cm²
Herstellung des sauren Phosphorsäureestergemisches:
33,3 g (0,45 mol) n-Butanol und 27,9 g (0,45 mol) Ethylenglykol wurden in einem 250-ml-Glasgefäß mit Rührvorrichtung unter Stickstoffatmosphäre gemischt. Anschließend wurden in das Gemisch im Verlauf von 30 min 63,9 g (0,225 mol) P₄O₁₀ eingetragen, wobei die Mischung mit einem Wasser-Eis-Gemisch gekühlt wurde. Die Temperatur des Reaktionsgemisches stieg während des Eintragens von 22 auf 55 °C. Nach dem Abklingen der exothermen Reaktion wurde das Gemisch innerhalb von einer Stunde auf 80 °C erwärmt und 1 Stunde lang bei 80 bis 85 °C gehalten. Nach dem Abkühlen wurden 125 g einer farblosen, viskosen Flüssigkeit mit einer Säurezahl bis zum zweiten Wendepunkt bei einem pH-Wert von 9,5 von 564 mg KOH/g erhalten.Preparation of the acidic phosphoric ester mixture:
33.3 g (0.45 mol) of n-butanol and 27.9 g (0.45 mol) of ethylene glycol were mixed in a 250 ml glass vessel with a stirrer under a nitrogen atmosphere. 63.9 g (0.225 mol) of P₄O₁₀ were then introduced into the mixture in the course of 30 min, the mixture being cooled with a water-ice mixture. The temperature of the reaction mixture rose from 22 to 55 ° C. during the introduction. After the exothermic reaction had subsided, the mixture was heated to 80 ° C. in the course of one hour and held at 80 to 85 ° C. for 1 hour. After cooling, 125 g of a colorless, viscous liquid with an acid number up to the second turning point at a pH of 9.5 of 564 mg KOH / g were obtained.
-
A)
- 42,07 %
- Triethylenglykol
- 6,60 %
- Triethylenglykolmonomethylether
- 35,00 %
- Triethylenglykolmono-n-butylether
- 15,00 %
- Triethylenglykoldimethylether
- 42.07%
- Triethylene glycol
- 6.60%
- Triethylene glycol monomethyl ether
- 35.00%
- Triethylene glycol mono-n-butyl ether
- 15.00%
- Triethylene glycol dimethyl ether
-
B)
- 1,10 %
- Tributylamin
- 0,20 %
- Benztriazol
- 1.10%
- Tributylamine
- 0.20%
- Benzotriazole
-
C)
- 0,03 %
- saures Phosphorsäureestergemisch wie im Beispiel 1
- 0.03%
- acidic phosphoric ester mixture as in Example 1
- Siedepunktboiling point
- 257 °C257 ° C
- NaßsiedepunktWet boiling point
- 146 °C146 ° C
- Viskositätviscosity
- 1 090 mm²/s1 090 mm² / s
- ZinnkorrosionTin corrosion
- -0,01 mg/cm²-0.01 mg / cm²
-
A)
- 34,59 %
- Tetraethylenglykolmonomethylether
- 61,40 %
- Borsäureester der Formel [CH₃O-(CH₂CH₂O)₃]₃-B
- 34.59%
- Tetraethylene glycol monomethyl ether
- 61.40%
- Boric acid esters of the formula [CH₃O- (CH₂CH₂O) ₃] ₃-B
-
B)
- 3,90 %
- Butyldiethanolamin
- 0,10 %
- Benztriazol
- 3.90%
- Butyldiethanolamine
- 0.10%
- Benzotriazole
-
C)
- 0,01 %
- saures Phosphorsäureestergemisch wie im Beispiel 1
- 0.01%
- acidic phosphoric ester mixture as in Example 1
- Siedepunktboiling point
- 282 °C282 ° C
- NaßsiedepunktWet boiling point
- 187 °C187 ° C
- Viskositätviscosity
- 1 264 mm²/s1 264 mm² / s
- ZinnkorrosionTin corrosion
- -0,01 mg/cm²-0.01 mg / cm²
-
A)
- 61,40 %
- Tetraethylenglykolmonomethylether
- 35,50 %
- Borsäureester der Formel
- 61.40%
- Tetraethylene glycol monomethyl ether
- 35.50%
- Boric acid esters of the formula
-
B)
- 3,00 %
- Diisopropanolamin
- 0,05 %
- Tolyltriazol
- 3.00%
- Diisopropanolamine
- 0.05%
- Tolyltriazole
-
C)
- 0,05 %
- saures Phosphorsäureestergemisch wie im Beispiel 1
- 0.05%
- acidic phosphoric ester mixture as in Example 1
- Siedepunktboiling point
- 270 °C270 ° C
- NaßsiedepunktWet boiling point
- 174 °C174 ° C
- Viskositätviscosity
- 1 768 mm²/s1 768 mm² / s
- ZinnkorrosionTin corrosion
- ±0 mg/cm²± 0 mg / cm²
-
A)
- 35,30 %
- Tetraethylenglykolmonomethylether
- 61,40 %
- Borsäureester wie im Beispiel 3
- 35.30%
- Tetraethylene glycol monomethyl ether
- 61.40%
- Boric acid esters as in Example 3
-
B)
- 3,20 %
- Diisopropanolamin
- 0,05 %
- Tolyltriazol
- 3.20%
- Diisopropanolamine
- 0.05%
- Tolyltriazole
-
C)
- 0,05 %
- von einem sauren Phosphorsäureestergemisch, das wie nachstehend beschrieben hergestellt worden ist.
- 0.05%
- of an acidic mixture of phosphoric acid esters prepared as described below.
- Siedepunktboiling point
- 284 °C284 ° C
- NaßsiedepunktWet boiling point
- 186 °C186 ° C
- Viskositätviscosity
- 1 250 mm²/s1 250 mm² / s
- ZinnkorrosionTin corrosion
- ±0 mg/cm²± 0 mg / cm²
Herstellung des sauren Phosphorsäureestergemisches:
75 g (0,5 mol) Triethylenglykol und 30 g (0,5 mol) Isopropanol wurden in einem 250-ml-Glasgefäß mit Rührvorrichtung unter Stickstoffatmosphäre gemischt. Anschließend wurden in das Gemisch im Verlauf von 30 min 71 g (0,25 mol) P₄O₁₀ eingetragen, wobei die Mischung mit einem Wasser-Eis-Gemisch gekühlt wurde. Die Temperatur des Reaktionsgemisches stieg während des Eintragens von 22 auf 60 °C. Das Reaktionsgemisch wurde nun 2 Stunden lang bei 80 °C gehalten. Das auf Raumtemperatur abgekühlte Produkt war eine leicht braun gefärbte, viskose Flüssigkeit. Die Säurezahl des Produktes betrug bis zum zweiten Wendepunkt 482 mg KOH/g.Preparation of the acidic phosphoric ester mixture:
75 g (0.5 mol) of triethylene glycol and 30 g (0.5 mol) of isopropanol were mixed in a 250 ml glass vessel with a stirrer under a nitrogen atmosphere. 71 g (0.25 mol) of P₄O₁₀ were then introduced into the mixture over the course of 30 minutes, the mixture being cooled with a water-ice mixture. The temperature of the reaction mixture rose from 22 to 60 ° C. during the introduction. The reaction mixture was now held at 80 ° C for 2 hours. The product, cooled to room temperature, was a light brown colored, viscous liquid. The acid number of the product was 482 mg KOH / g up to the second turning point.
-
A)
- 59,00 %
- Tetraethylenglykolmonomethylether
- 35,50 %
- Borsäureester wie im Beispiel 4
- 59.00%
- Tetraethylene glycol monomethyl ether
- 35.50%
- Boric acid esters as in Example 4
-
B)
- 5,40 %
- Octyldiethanolamin
- 0,10 %
- Benztriazol
- 5.40%
- Octyldiethanolamine
- 0.10%
- Benzotriazole
-
C)
- 0,03 %
- von einem sauren Phosphorsäureestergemisch, das wie nachstehend beschrieben hergestellt worden ist.
- 0.03%
- of an acidic mixture of phosphoric acid esters prepared as described below.
- Siedepunktboiling point
- 270 °C270 ° C
- NaßsiedepunktWet boiling point
- 173 °C173 ° C
- Viskositätviscosity
- 1 760 mm²/s1 760 mm² / s
- ZinnkorrosionTin corrosion
- ±0 mg/cm²± 0 mg / cm²
Herstellung des sauren Phosphorsäureestergemisches:
Es wurde wie im Beispiel 5 vorgegangen, wobei jedoch 38 g (0,5 mol) Propandiol-1,3 und 23 g (0,5 mol) Ethanol mit 71 g (0,25 mol) P₄O₁₀ umgesetzt wurden. Es wurde eine leicht braun gefärbte, viskose Flüssigkeit mit einer Säurezahl bis zum zweiten Wendepunkt von 589 mg KOH/g erhalten.Preparation of the acidic phosphoric ester mixture:
The procedure was as in Example 5, but 38 g (0.5 mol) of 1,3-propanediol and 23 g (0.5 mol) of ethanol were reacted with 71 g (0.25 mol) of P₄O₁₀. A slightly brown colored, viscous liquid with an acid number up to the second turning point of 589 mg KOH / g was obtained.
-
A)
- 17,99 %
- Triethylenglykolmonomethylether
- 5,00 %
- Tetraethylenglykoldimethylether
- 74,80 %
- Borsäureester wie im Beispiel 3
- 17.99%
- Triethylene glycol monomethyl ether
- 5.00%
- Tetraethylene glycol dimethyl ether
- 74.80%
- Boric acid esters as in Example 3
-
B)
- 2,10 %
- Diisopropanolamin
- 0,10 %
- Tolyltriazol
- 2.10%
- Diisopropanolamine
- 0.10%
- Tolyltriazole
-
C)
- 0,01 %
- saures Phosphorsäureestergemisch wie im Beispiel 1
- 0.01%
- acidic phosphoric ester mixture as in Example 1
- Siedepunktboiling point
- 275 °C275 ° C
- NaßsiedepunktWet boiling point
- 195 °C195 ° C
- Viskositätviscosity
- 880 mm²/s880 mm² / s
- ZinkorrosionZinc corrosion
- ±0 mg/cm²± 0 mg / cm²
Die erfindungsgemäßen Beispiele 1 bis 7 wurden wiederholt, mit dem Unterschied, daß die Komponente C) nicht eingesetzt wurde [die Ergänzung der Bremsflüssigkeitsmischung auf 100 Gew.-% erfolgte mit Hilfe des ersten Vertreters der Komponente A)].Examples 1 to 7 according to the invention were repeated, with the difference that component C) was not used [the brake fluid mixture was supplemented to 100% by weight with the aid of the first representative of component A)].
Diese Bremsflüssigkeiten hatten bezüglich Siedepunkt, Naßsiedepunkt und Viskosität bei -40 °C praktisch die gleichen Werte wie die erfindungsgemäßen Bremsflüssigkeiten, bezüglich Zinnkorrosion hingegen waren sie wesentlich schlechter; die Zinnkorrosionswerte lagen im Bereich von -0,12 bis -0,16 mg/cm².With regard to boiling point, wet boiling point and viscosity at -40 ° C., these brake fluids had practically the same values as the brake fluids according to the invention, but were considerably worse with regard to tin corrosion; the tin corrosion values ranged from -0.12 to -0.16 mg / cm².
-
A)
- 35,30 %
- Tetraethylenglykolmonomethylether
- 61,40 %
- Borsäureester wie im Beispiel 3
- 35.30%
- Tetraethylene glycol monomethyl ether
- 61.40%
- Boric acid esters as in Example 3
-
B)
- 3,20 %
- Diisopropanolamin
- 0,05 %
- Tolyltriazol
- 3.20%
- Diisopropanolamine
- 0.05%
- Tolyltriazole
-
C)
- 0,05 %
- von einem sauren Phosphorsäureestergemisch, das wie nachstehend beschrieben hergestellt worden ist.
- 0.05%
- of an acidic mixture of phosphoric acid esters prepared as described below.
- SidepunktSide point
- 285 °C285 ° C
- NaßsiedepunktWet boiling point
- 185 °C185 ° C
- Viskositätviscosity
- 1 285 mm²/s1 285 mm² / s
- ZinnkorrosionTin corrosion
- -0,10 mg/cm²-0.10 mg / cm²
Herstellung des sauren Phosphorsäureestergemisches:
90 g (1,5 mol) Isopropanol wurden in einem 250-ml-Glasgefäß mit Rührvorrichtung unter Stickstoffatmosphäre vorgelegt. Anschließend wurden portionsweise 71 g (0,25 mol) P₄O₁₀ eingetragen, wobei die Mischung durch Kühlung mit einem Wasser-Eis-Gemisch bei 22 bis 40 °C gehalten wurde. Das Reaktionsgemisch wurde nun 1 Stunde lang bei 80 °C gehalten. Es wurde eine wasserklare, viskose Flüssigkeit mit einer Säurezahl bis zum zweiten Wendepunkt von 490 mg KOH/g erhalten.Preparation of the acidic phosphoric ester mixture:
90 g (1.5 mol) of isopropanol were placed in a 250 ml glass vessel with a stirrer under a nitrogen atmosphere. Then 71 g (0.25 mol) of P₄O₁₀ were added in portions, the mixture being kept at 22 to 40 ° C. by cooling with a water-ice mixture. The reaction mixture was now held at 80 ° C for 1 hour. A water-clear, viscous liquid with an acid number up to the second turning point of 490 mg KOH / g was obtained.
Claims (9)
- A process for the preparation of brake fluids inhibited against metallic corrosion, characterized in that the following components A) to C) are mixed,A) being at least one glycol compound as main component,B) being at least one inhibitor for fluids based on glycol compounds andC) being 0.005 to 0.5% by weight, percent by weight being based on the weight of the brake fluid, of a mixture of acid phosphoric esters, consisting essentially of monophosphoric esters and diphosphoric esters and obtained by reacting a phosphorus-containing compound with a monohydric alcohol and a polyol.
- A process as claimed in claim 1, in which the amount of component C) is 0.01 to 0.1% by weight.
- A process as claimed in claim 1 or 2, in which component C) is a mixture of acid phosphoric esters obtained by reacting phosphorus(V) oxide with a mixture consisting of a monohydric alcohol and an alkanepolyol having 2 to 12 carbon atoms and 2 to 6 hydroxyl groups, while maintaining a molar ratio of phosphorus(V) oxide : monohydric alcohol : alkanepolyol of 1 : 2 : 4/n', in which n' is the number of hydroxyl groups in the alkanepolyol molecule, or a stoichiometric excess of the alcoholic components, with mixing or kneading of the reactants at a temperature of about 0 to 120°C with the exclusion of moisture and in the presence of an inert gas for about 1 to 6 hours.
- A process as claimed in claim 1 or 2 in which component C) is a mixture of acid phosphoric esters obtained by reacting phosphorus(V) oxide with a mixture consisting of a monohydric alcohol of the formula 8 below
HO-(CH₂)f-OH (9)
in which f is 2 to 8, or of the formula 10 below - A process as claimed in one or more of claims 1 to 4, in which component A) comprises glycol compounds selected from the group comprising glycols, glycol monoalkyl ethers, glycol dialkyl ethers, glycol formals, glycol boric esters and glycol monoalkyl ether boric esters, and component B) comprising inhibitors selected from the group comprising alkylamines, cycloalkylamines, alkanolamines, monocarboxylic acids and alkali metal salts thereof, dicarboxylic acids and alkali metal salts thereof, alkali metal salts of carbonic acid, phosphoric acid and molybdic acid, triazoles, imidazoles and antioxidant aromatic compounds.
- A process as claimed in one or more of claims 1 to 4, in which component A) comprises glycol compounds selected from the group comprising glycols of the formula 1 below
R⁷O-(CH₂CH₂O)m-CH₂-(OCH₂CH₂)n-OR⁸ (4)
in which R⁷ is C₁- to C₄-alkyl, R⁸ is C₁- to C₄-alkyl, m is 1 to 4 and n is 1 to 4, and glycol boric esters of formula 5 below
[R⁹O-(CH₂CH₂O)a]₃-B (5)
in which R⁹ is C₁- to C₄-alkyl and a is 1 to 6, and glycol monoalkyl ether boric esters of formula 6 below - A process as claimed in one or more of claims 1 to 6, in which component B) comprises inhibitors selected from the group comprising mono-, di- and trialkylamines having 1 to 18 carbon atoms in each alkyl group, alkanolamines of formula 7 below
- A process as claimed in one or more of claims 1 to 7, in which component B) is present in an amount of 0.1 to 10% by weight, the percent by weight being based on the weight of the brake fluid.
- A process as claimed in one or more of claims 1 to 8, in which component B) comprises inhibitors selected from the group comprising mono-, di- and trialkylamines having 1 to 18 carbon atoms in each alkyl group, alkanolamines of formula 7 below
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4013243A DE4013243A1 (en) | 1990-04-26 | 1990-04-26 | AGAINST METAL CORROSION INHIBITED BRAKE FLUIDS BASED ON GLYCOL COMPOUNDS |
DE4013243 | 1990-04-26 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0454110A1 EP0454110A1 (en) | 1991-10-30 |
EP0454110B1 true EP0454110B1 (en) | 1993-05-19 |
Family
ID=6405091
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP91106665A Expired - Lifetime EP0454110B1 (en) | 1990-04-26 | 1991-04-25 | Fluids based on glycol compounds, for metal corrosion inhibiting brakes |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP0454110B1 (en) |
JP (1) | JP2925038B2 (en) |
DE (2) | DE4013243A1 (en) |
DK (1) | DK0454110T3 (en) |
ES (1) | ES2058980T3 (en) |
IE (1) | IE65470B1 (en) |
PT (1) | PT97459B (en) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994004637A1 (en) * | 1992-08-18 | 1994-03-03 | Ethyl Japan Corporation | Lubricating oil composition for wet clutch or wet brake |
US5851962A (en) * | 1992-08-18 | 1998-12-22 | Ethyl Japan Corporation | Lubricant composition for wet clutch or wet brake |
CA2199172A1 (en) * | 1994-12-09 | 1996-06-13 | Raymond Frederick Watts | Oil soluble complexes of phosphorus-containing acids useful as lubricating oil additives |
DE19546856C1 (en) * | 1995-12-15 | 1997-06-26 | Hoechst Ag | Test procedure for hydraulic fluids based on glycols and glycol boric acid esters with regard to precipitation tendency |
US6074992A (en) * | 1999-02-02 | 2000-06-13 | Union Carbide Chemicals & Plastics Technology Corporation | Functional fluid compositions |
DE10117647A1 (en) * | 2001-04-09 | 2002-10-17 | Basf Ag | Hydraulic fluids with improved corrosion protection |
US8188016B2 (en) | 2003-07-08 | 2012-05-29 | Ntn Corporation | Lubricant composition and bearing using same |
JP2009507938A (en) * | 2005-07-01 | 2009-02-26 | ダウ グローバル テクノロジーズ インコーポレイティド | Low viscosity functional fluid |
US20080182770A1 (en) * | 2007-01-26 | 2008-07-31 | The Lubrizol Corporation | Antiwear Agent and Lubricating Compositions Thereof |
WO2010053639A1 (en) * | 2008-11-07 | 2010-05-14 | Dow Global Technologies Inc. | Low viscosity functional fluids |
JP5851911B2 (en) * | 2012-03-29 | 2016-02-03 | シーシーアイ株式会社 | Hydraulic fluid |
PL237249B1 (en) * | 2018-02-27 | 2021-03-22 | Przemyslowy Inst Motoryzacji | Protective oil |
MX2021002816A (en) * | 2020-04-23 | 2022-01-24 | Clariant Int Ltd | Low viscosity functional fluid composition. |
JP7373474B2 (en) * | 2020-08-25 | 2023-11-02 | 出光興産株式会社 | lubricating oil composition |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4141938A (en) * | 1976-10-07 | 1979-02-27 | Hoechst Aktiengesellschaft | Production of acid orthophosphoric acid ester mixtures |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1230781A (en) * | 1967-04-13 | 1971-05-05 | ||
FR2101027A1 (en) * | 1970-08-10 | 1972-03-31 | Naphtachimie Sa | Aqs hydraulic fluid - contg polyoxyalkylene ether - phosphate and amine base has improved lubrication |
DE2756747A1 (en) * | 1977-12-20 | 1979-06-28 | Basf Ag | CORROSION PROTECTION AGENT |
DE2926269A1 (en) * | 1979-06-29 | 1981-01-15 | Hoechst Ag | Hydraulic fluids based on borate ester - comprising poly:ethoxylated tri:alkyl metaborate and di:alkyl formal derivs. |
DE2941419A1 (en) * | 1979-10-12 | 1981-04-23 | Hoechst Ag, 6000 Frankfurt | USE OF ACID PHOSPHORIC ACID ESTERS OR THEIR SALTS AS AN AGENT TO PREVENT CORROSION OF METALS |
DE2945094A1 (en) * | 1979-11-08 | 1981-05-21 | Hoechst Ag, 6000 Frankfurt | HYDRAULIC LIQUID WITH IMPROVED PROPERTIES |
-
1990
- 1990-04-26 DE DE4013243A patent/DE4013243A1/en not_active Withdrawn
-
1991
- 1991-04-24 PT PT97459A patent/PT97459B/en active IP Right Grant
- 1991-04-24 JP JP3094270A patent/JP2925038B2/en not_active Expired - Fee Related
- 1991-04-25 DE DE9191106665T patent/DE59100117D1/en not_active Expired - Fee Related
- 1991-04-25 EP EP91106665A patent/EP0454110B1/en not_active Expired - Lifetime
- 1991-04-25 DK DK91106665.2T patent/DK0454110T3/en active
- 1991-04-25 IE IE138891A patent/IE65470B1/en not_active IP Right Cessation
- 1991-04-25 ES ES91106665T patent/ES2058980T3/en not_active Expired - Lifetime
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4141938A (en) * | 1976-10-07 | 1979-02-27 | Hoechst Aktiengesellschaft | Production of acid orthophosphoric acid ester mixtures |
Also Published As
Publication number | Publication date |
---|---|
DK0454110T3 (en) | 1993-11-22 |
DE4013243A1 (en) | 1991-10-31 |
PT97459A (en) | 1992-01-31 |
DE59100117D1 (en) | 1993-06-24 |
IE65470B1 (en) | 1995-11-01 |
EP0454110A1 (en) | 1991-10-30 |
JPH04227690A (en) | 1992-08-17 |
ES2058980T3 (en) | 1994-11-01 |
IE911388A1 (en) | 1991-11-06 |
JP2925038B2 (en) | 1999-07-26 |
PT97459B (en) | 1998-08-31 |
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