EP0454110A1 - Fluides pour freins inhibés contre la corrosion métallique à base de composés de glycols - Google Patents

Fluides pour freins inhibés contre la corrosion métallique à base de composés de glycols Download PDF

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Publication number
EP0454110A1
EP0454110A1 EP91106665A EP91106665A EP0454110A1 EP 0454110 A1 EP0454110 A1 EP 0454110A1 EP 91106665 A EP91106665 A EP 91106665A EP 91106665 A EP91106665 A EP 91106665A EP 0454110 A1 EP0454110 A1 EP 0454110A1
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EP
European Patent Office
Prior art keywords
glycol
alkyl
formula
brake fluid
component
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP91106665A
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German (de)
English (en)
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EP0454110B1 (fr
Inventor
Klaus Ulm
Maria Maier
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Clariant Produkte Deutschland GmbH
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Hoechst AG
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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
    • 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
    • C10M2227/0615—Esters derived from boron used as base material
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/003—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/02—Groups 1 or 11
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids

Definitions

  • the 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.
  • the property requirements for these fluids are specified in US Federal Motor Vehicle Safety Standard 116 (FMVSS No. 116) and in US Society of Automotive Engineers J 1703 (SAE J 1703).
  • FMVSS No. 116 US Federal Motor Vehicle Safety Standard 116
  • SAE J 1703 US Society of Automotive Engineers J 1703
  • the important properties of a brake fluid include the dry boiling point (also known as reflux boiling point or simply boiling point), the wet boiling point (also known as reflux boiling point and wet) and the viscosity at -40 ° C. The values required in this regard are summarized below:
  • 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.
  • the object of the invention is therefore to provide a brake fluid that has both the standard properties mentioned and good corrosion inhibition compared to the usual metals and at the same time against 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.
  • 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.
  • 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 have been known for a long time (compare the publications mentioned at the beginning).
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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 alkali metal salts of carbonic acid, phosphoric acid and molybdic acid are sodium carbonate, sodium phosphate and sodium molybdate (Na2MoO4).
  • 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.
  • 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.
  • 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.
  • 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).
  • Suitable phosphorus compounds are, for example, phosphoric acid (H3PO4), phosphorus trichloride (PCl3), phosphorus pentachloride (PCl5) and phosphorus pentoxide (P4O10).
  • 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.
  • Suitable monohydric alcohols are those from the group of alkanols and alkoxylated alkanols.
  • 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.
  • 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.
  • 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.
  • ethanediol ethylene glycol
  • 1,2-propanediol 1,3-propanediol
  • 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).
  • 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.
  • 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 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.
  • the reaction mixture has cooled, the desired mixture of acidic phosphoric acid esters is present.
  • 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).
  • 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.
  • 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.
  • 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.
  • component A 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.
  • Composition 1 is a composition of Composition 1:
  • Composition 2 is a composition of Composition 2:
  • Composition 3 is a composition of Composition 3:
  • Composition 4 is a composition having Composition 4:
  • Composition 5 is a composition of Composition 5:
  • composition 6 is a composition of Composition 6:
  • Composition 7 is a composition of Composition 7:
  • Composition 8 is a composition of Composition 8:
  • composition 9 is a composition of Composition 9:
  • 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.
  • 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.
  • the brake fluids according to the invention are particularly suitable for hydraulic brake systems, preferably those in motor vehicles.
  • 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.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Lubricants (AREA)
EP91106665A 1990-04-26 1991-04-25 Fluides pour freins inhibés contre la corrosion métallique à base de composés de glycols Expired - Lifetime EP0454110B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4013243A DE4013243A1 (de) 1990-04-26 1990-04-26 Gegen metallkorrosion inhibierte bremsfluessigkeiten auf der basis von glykolverbindungen
DE4013243 1990-04-26

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EP0454110A1 true EP0454110A1 (fr) 1991-10-30
EP0454110B1 EP0454110B1 (fr) 1993-05-19

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EP (1) EP0454110B1 (fr)
JP (1) JP2925038B2 (fr)
DE (2) DE4013243A1 (fr)
DK (1) DK0454110T3 (fr)
ES (1) ES2058980T3 (fr)
IE (1) IE65470B1 (fr)
PT (1) PT97459B (fr)

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WO1996017914A1 (fr) * 1994-12-09 1996-06-13 Exxon Chemical Patents Inc. Composes solubles dans l'huile d'acides contenant du phosphore et pouvant etre utilises comme additifs d'huile lubrifiante
WO2002081604A1 (fr) * 2001-04-09 2002-10-17 Basf Aktiengesellschaft Liquides hydrauliques a proprietes anticorrosion ameliorees
WO2010053639A1 (fr) * 2008-11-07 2010-05-14 Dow Global Technologies Inc. Liquides fonctionnels à faible viscosité

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US5851962A (en) * 1992-08-18 1998-12-22 Ethyl Japan Corporation Lubricant composition for wet clutch or wet brake
DE69327453T3 (de) * 1992-08-18 2004-07-01 Ethyl Japan Corp. Verwendung von anorganischen phosphorverbindungen als friktionsverbesserer in schmiermittelzusammensetzungen für flüssigkeitskupplungen oder flüssigkeitsbremsen
DE19546856C1 (de) * 1995-12-15 1997-06-26 Hoechst Ag Testverfahren für hydraulische Flüssigkeiten auf der Basis von Glykolen und Glykolborsäureestern bezüglich Niederschlagsneigung
US6074992A (en) * 1999-02-02 2000-06-13 Union Carbide Chemicals & Plastics Technology Corporation Functional fluid compositions
US8188016B2 (en) 2003-07-08 2012-05-29 Ntn Corporation Lubricant composition and bearing using same
EP1934317A2 (fr) * 2005-07-01 2008-06-25 Dow Gloval Technologies Inc. Fluide fonctionnel a faible viscosite
US20080182770A1 (en) * 2007-01-26 2008-07-31 The Lubrizol Corporation Antiwear Agent and Lubricating Compositions Thereof
JP5851911B2 (ja) * 2012-03-29 2016-02-03 シーシーアイ株式会社 作動液
PL237249B1 (pl) * 2018-02-27 2021-03-22 Przemyslowy Inst Motoryzacji Olej ochronny
PL3938479T3 (pl) * 2020-04-23 2023-10-23 Clariant International Ltd Kompozycja funkcjonalnego płynu o niskiej lepkości
JP7373474B2 (ja) * 2020-08-25 2023-11-02 出光興産株式会社 潤滑油組成物

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WO1996017914A1 (fr) * 1994-12-09 1996-06-13 Exxon Chemical Patents Inc. Composes solubles dans l'huile d'acides contenant du phosphore et pouvant etre utilises comme additifs d'huile lubrifiante
US5773392A (en) * 1994-12-09 1998-06-30 Exxon Chemical Patents Inc. Oil soluble complexes of phosphorus-containing acids useful as lubricating oil additives
WO2002081604A1 (fr) * 2001-04-09 2002-10-17 Basf Aktiengesellschaft Liquides hydrauliques a proprietes anticorrosion ameliorees
CN1312261C (zh) * 2001-04-09 2007-04-25 巴斯福股份公司 具有改进的防腐性能的水力流体
CZ299651B6 (cs) * 2001-04-09 2008-10-01 Basf Aktiengesellschaft Brzdová kapalina pro motorová vozidla mající zlepšenou ochranu proti korozi
KR100861969B1 (ko) * 2001-04-09 2008-10-08 바스프 에스이 방식성이 개선된 유압 작동액
WO2010053639A1 (fr) * 2008-11-07 2010-05-14 Dow Global Technologies Inc. Liquides fonctionnels à faible viscosité

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Publication number Publication date
PT97459A (pt) 1992-01-31
DK0454110T3 (da) 1993-11-22
JPH04227690A (ja) 1992-08-17
DE59100117D1 (de) 1993-06-24
EP0454110B1 (fr) 1993-05-19
PT97459B (pt) 1998-08-31
JP2925038B2 (ja) 1999-07-26
IE911388A1 (en) 1991-11-06
ES2058980T3 (es) 1994-11-01
IE65470B1 (en) 1995-11-01
DE4013243A1 (de) 1991-10-31

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