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EP0454110B1 - 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
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.)
Expired - Lifetime
Application number
EP91106665A
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German (de)
English (en)
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EP0454110A1 (fr
Inventor
Klaus Ulm
Maria Maier
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Clariant Produkte Deutschland GmbH
Original Assignee
Hoechst AG
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
    • C10M2223/121—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy of alcohols or phenols
    • 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

  • 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.

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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)

Claims (9)

  1. Procédé pour préparer un liquide de frein protégé contre la corrosion des métaux, caractérisé en ce qu'on mélange les composants A) à C) ci-après, dans lesquels :
    A) est au moins un composé du glycol servant de composant principal,
    B) est au moins un inhibiteur pour liquides, à base de composés du glycol, et
    C) représente de 0,005 à 0,5 % en poids d'un mélange de phosphates acides constitués essentiellement d'esters de l'acide monophosphorique et d'esters de l'acide diphosphorique, mélange que l'on a obtenu par réaction d'un composé phosphoré avec un monoalcool et un polyol, les pourcentages en poids étant rapportés au poids du liquide de frein.
  2. Procédé selon la revendication 1, dans lequel la quantité du composant C) est de 0,01 à 0,1 % en poids.
  3. Procédé selon la revendication 1 ou 2, dans lequel le composant C) est un mélange de phosphates acides, que l'on obtient par réaction de l'oxyde de phosphore-V avec un mélange constitué d'un monoalcool et d'un alcanepolyol ayant de 2 à 12 atomes de carbone et de 2 à 6 groupes hydroxyle, en respectant une proportion molaire oxyde de phosphore-V:monoalcool:alcanepolyol de 1:2:4/n', où n' est le nombre des groupes hydroxyle de la molécule d'alcanepolyol, ou d'un excès stoechiométrique des composants alcooliques, par mélange ou malaxage des composants de la réaction à une température d'environ 0 à 120°C, à l'abri de l'humidité et en présence d'un gaz inerte, et ce pendant environ 1 à 6 heures.
  4. Procédé selon la revendication 1 ou 2, dans lequel le composant C) est un mélange de phosphates acides que l'on a obtenu par réaction d'oxyde de phosphore-V et d'un mélange constitué d'un monoalcool ayant la formule 8 ci-après :
    Figure imgb0071
     dans laquelle R¹⁵ est H ou CH₃, R¹⁶ est un radical alkyle ayant de 1 à 12 atomes de carbone, et e vaut de 0 à 15, et un alcanepolyol ayant la formule 9 ci-après :

            HO-(CH₂)f-OH   (9)

    dans laquelle f vaut de 2 à 8, ou encore ayant la formule 10 ci-après :
    Figure imgb0072
     dans laquelle R¹⁷ est H ou CH₃, et g vaut de 1 à 10, en respectant une proportion molaire oxyde de phosphore-V: monoalcool:alcanepolyol de 1:2:4/n', où n' est le nombre des groupes hydroxyle de la molécule d'alcanepolyol, ou d'un excès stoechiométrique des composants alcooliques, par mélange ou malaxage des composants de la réaction à une température d'environ 0 à 120°C, à l'abri de l'humidité et en présence d'un gaz inerte, et ce pendant environ 1 à 6 heures.
  5. Procédé selon l'une ou plusieurs des revendications 1 à 4, dans lequel le composant A) est constitué de composés du glycol choisis parmi l'ensemble comprenant les glycols, les éthers monoalkyliques du glycol, les éthers dialkyliques du glycol, les glycolformals, les esters de l'acide borique et du glycol et les esters de l'acide borique et des éthers monoalkyliques du glycol, et le composant B) est constitué d'inhibiteurs choisi parmi l'ensemble comprenant les alkylamines, les cycloalkylamines, les alcanolamines, les acides monocarboxyliques et leurs sels de métaux alcalins, les acides dicarboxyliques et leurs sels de métaux alcalins, les sels de métaux alcalins de l'acide carbonique, de l'acide phosphorique et de l'acide molybdique, les triazoles, les imidazoles et les composés aromatiques antioxydants.
  6. Procédé selon l'une ou plusieurs des revendications 1 à 4, dans lequel le composant A) est constitué de composés du glycol choisis parmi l'ensemble comprenant les glycols ayant la formule 1 ci-après :
    Figure imgb0073
     dans laquelle R¹ est H ou CH₃ et, dans la chaîne polyalcoxylène, représente aussi H et CH₃, et x vaut de 1 à 8,
    les éthers monoalkyliques du glycol ayant la formule 2 ci-après :
    Figure imgb0074
     dans laquelle R² est H ou CH₃ et, dans la chaîne polyalcoxylène, représente aussi H et CH₃, R³ est un radical alkyle en C₁-C₄ et y vaut de 1 à 6,
    Les éthers dialkyliques du glycol ayant la formule 3 ci-après :
    Figure imgb0075
     dans laquelle R⁴ est H ou CH₃ et, dans la chaîne polyalcoxylène, représente aussi H et CH₃, R⁵ est un radical alkyle en C₁-C₄, R⁶ est un radical alkyle en C₁-C₄, et z vaut 1 à 6,
    les glycolformals ayant la formule 4 ci-après :

            R⁷O-(CH₂CH₂O)m-CH₂-(OCH₂CH₂)n-OR⁸   (4)

    dans laquelle R⁷ est un radical alkyle en C₁-C₄, R⁸ est un radical alkyle en C₁-C₄, m vaut de 1 à 4 et n vaut de 1 à 4, et
    les esters de l'acide borique et du glycol ayant la formule 5 ci-après :

            [R⁹O-(CH₂CH₂O)a]₃-B   (5)

    dans laquelle R⁹ est un radical alkyle en C₁-C₄, et a vaut de 1 à 6, et
    les esters de l'acide borique et des éthers monoalkyliques du glycol ayant la formule 6 ci-après :
    Figure imgb0076
     dans laquelle R¹⁰ est un radical alkyle en C₁-C₄, R¹¹ est un radical alkyle en C₁-C₄, et b vaut de 1 à 6 et c vaut de 1 à 6,
    Le composant B) étant constitué d'inhibiteurs choisis parmi l'ensemble comprenant les mono-, les di- et les trialkylamines ayant de 1 à 18 atomes de carbone dans chaque groupe alkyle,
    les alcanolamines ayant la formule 7 ci-après :
    Figure imgb0077
     dans laquelle R¹² est H ou CH₃, d vaut 0, 1 ou 2, R¹³ est H, un radical alkyle en C₁-C₁₈ ou un résidu ayant la formule ci-après :
    Figure imgb0078
     dans laquelle R¹² et d ont les significations données ci-dessus, et R¹⁴ a l'une des significations de R¹³,
    les acides monocarboxyliques en C₅-C₁₈ et leurs sels de métaux alcalins, les acides dicarboxyliques de formule HOOC-(CH₂)k-COOH dans laquelle k vaut de 4 à 10, les sels de métaux alcalins de l'acide carbonique, de l'acide phosphorique et de l'acide molybdique, et les triazoles, imidazoles et composés aromatiques antioxydants choisis parmi l'ensemble comprenant les phénols, les bisphénols, les crésols, les quinoléines et les naphtylamines.
  7. Procédé selon l'une ou plusieurs des revendications 1 à 6, dans lequel le composant B) est constitué d'inhibiteurs choisis parmi l'ensemble comprenant les mono-, di- et trialkylamines ayant de 1 à 18 atomes de carbone dans chaque groupe alkyle, les alcanolamines ayant la formule 7 ci-après :
    Figure imgb0079
     dans laquelle R¹² est H ou CH₃, d vaut 0, 1 ou 2, R¹³ est H, un radical alkyle en C₁-C₁₈ ou un résidu ayant la formule ci-après :
    Figure imgb0080
     dans laquelle R¹² et d ont les significations données ci-dessus, et R¹⁴ a l'une des significations de R¹³,
    ainsi que les triazoles.
  8. Procédé selon l'une ou plusieurs des revendications 1 à 7, dans lequel le composant B) est présent en une quantité de 0,1 à 10 % en poids par rapport au poids du liquide de frein.
  9. Procédé selon l'une ou plusieurs des revendications 1 à 8, dans lequel le composant B) est constitué d'inhibiteurs choisis parmi l'ensemble comprenant les mono-, di- et trialkylamines ayant de 1 à 18 atomes de carbone dans chaque groupe alkyle, les alcanolamines ayant la formule 7 ci-après :
    Figure imgb0081
     dans laquelle R¹² est H ou CH₃, d vaut 0, 1 ou 2, R¹³ est H, un radical alkyle en C₁-C₁₈ ou un résidu ayant la formule ci-après :
    Figure imgb0082
     dans laquelle R¹² et d ont les significations données ci-dessus, et R¹⁴ a l'une des significations de R¹³,
    en une quantité de 0,5 à 8 % en poids, et les triazoles, en une quantité de 0,01 à 0,5 % en poids par rapport au poids du liquide de frein.
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)

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DE4013243A DE4013243A1 (de) 1990-04-26 1990-04-26 Gegen metallkorrosion inhibierte bremsfluessigkeiten auf der basis von glykolverbindungen

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DE69327453T3 (de) * 1992-08-18 2004-07-01 Ethyl Japan Corp. Verwendung von anorganischen phosphorverbindungen als friktionsverbesserer in schmiermittelzusammensetzungen für flüssigkeitskupplungen oder flüssigkeitsbremsen
US5851962A (en) * 1992-08-18 1998-12-22 Ethyl Japan Corporation Lubricant composition for wet clutch or wet brake
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
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
DE10117647A1 (de) * 2001-04-09 2002-10-17 Basf Ag Hydraulische Flüssigkeiten mit verbessertem Korrosionsschutz
US8188016B2 (en) 2003-07-08 2012-05-29 Ntn Corporation Lubricant composition and bearing using same
BRPI0613845A2 (pt) * 2005-07-01 2011-02-15 Dow Global Technologies Inc composição de fluìdo funcional e sistema de frenagem para veìculos
US20080182770A1 (en) * 2007-01-26 2008-07-31 The Lubrizol Corporation Antiwear Agent and Lubricating Compositions Thereof
WO2010053639A1 (fr) * 2008-11-07 2010-05-14 Dow Global Technologies Inc. Liquides fonctionnels à faible viscosité
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
WO2021213693A1 (fr) * 2020-04-23 2021-10-28 Clariant International Ltd Composition de fluide fonctionnel à faible viscosité
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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US4141938A (en) * 1976-10-07 1979-02-27 Hoechst Aktiengesellschaft Production of acid orthophosphoric acid ester mixtures

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PT97459A (pt) 1992-01-31
DE59100117D1 (de) 1993-06-24
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PT97459B (pt) 1998-08-31
IE911388A1 (en) 1991-11-06
DK0454110T3 (da) 1993-11-22

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