EP0617116B1 - Composition de fluide hydraulique - Google Patents

Composition de fluide hydraulique Download PDF

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Publication number
EP0617116B1
EP0617116B1 EP94301644A EP94301644A EP0617116B1 EP 0617116 B1 EP0617116 B1 EP 0617116B1 EP 94301644 A EP94301644 A EP 94301644A EP 94301644 A EP94301644 A EP 94301644A EP 0617116 B1 EP0617116 B1 EP 0617116B1
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EP
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Prior art keywords
ether
hydraulic fluid
fluid composition
amine
linear
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EP94301644A
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German (de)
English (en)
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EP0617116A1 (fr
Inventor
Andre Gillmann
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BP Chemicals Ltd
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BP Chemicals SNC
BP Chemicals Ltd
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/041—Triaryl phosphates
    • 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
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids

Definitions

  • the present invention relates to a hydraulic fluid composition and in particular to a brake fluid composition.
  • the preparation is known of hydraulic fluids based on glycol ethers and/or based on boric esters of glycol ethers. These hydraulic fluids most often contain additives, in particular corrosion-inhibiting or oxidation inhibiting additives and a neutralizing agent.
  • the preparation is known of hydraulic fluids containing amines as corrosion-inhibiting additives and/or as neutralizing agents.
  • the use is known, according to European Patent Application EP-A-454 110 and Patent US 3 711 410, of alkanolamines.
  • these alkanolamines do not make it possible to prepare hydraulic fluids of high boiling point which simultaneously have a number of specific characteristics.
  • they do not make it possible to prepare hydraulic fluids having a desired viscosity and optionally a desired volatility as a function of the boiling point, while moreover having good compatibility with elastomers of styrene butadiene rubber (SBR) type, a basic pH and good corrosion-inhibiting properties.
  • SBR styrene butadiene rubber
  • the present invention relates to a high boiling point hydraulic fluid composition which makes it possible to solve the problems mentioned above.
  • the subject of the present invention is thus a hydraulic fluid composition based on at least one glycol ether or on at least one boric ester of a glycol ether or a mixture of the two, characterised in that it contains, as additive, at least one ether-amine having a molecular weight between 120 and 300 and having the following formula: in which R 3 is linear or branched radical having at least one ether functional group and no alcohol functional group, R is a methyl radical or a hydrogen atom, p is an integer from 1 to 3 and q is an integer from 0 to 2.
  • the composition contains an ether-amine used essentially as a corrosion-inhibiting additive and/or a neutralizing agent.
  • This ether-amine has a molecular weight between 120 and 300.
  • a composition is obtained which is volatile and which has a low boiling point.
  • a composition is obtained which has an excessively high viscosity.
  • the molecular weight of the ether-amine is preferably from 150 to 250.
  • the ether-amine used must contain a radical R3 which is a linear or branched radical having at least one ether functional group and no alcohol functional group.
  • radical R3 is not cyclic.
  • R3 has the following formula R1-O-R2- in which R1 is a linear or branched alkyl radical preferably having from 1 to 5 carbon atoms and R2 is a linear or branched alkylene radical preferably having from 2 to 8 carbon atoms.
  • the ether-amine comprises at least one and preferably at least 2 units derived from an epoxide.
  • the ether-amine is generally obtained by reacting a starting ether-amine, with an epoxide such as, for example, ethylene oxide, propylene oxide or a mixture of the two.
  • an epoxide such as, for example, ethylene oxide, propylene oxide or a mixture of the two.
  • a particularly advantageous starting ether-amine can have the following general formula (A): R 1 -O-R 2 -NH 2 in which R 1 and R 2 have the same meaning as above.
  • the ether-amine obtained advantageously contains the amines having the following formula (B): in which R 1 , R 2 , R, p and q have the same meaning as above.
  • the hydraulic fluid composition according to the invention most often contains, by weight, between 0.5 and 5 %, and preferably between 1 and 4 %, of the ether-amine.
  • the composition of the invention has generally a viscosity measured at 40°C equal to or less than 10 mm2/s, and preferably comprised between 2 and 8 mm2/s. It essentially consists of at least one glycol ether such as, for example, butyl triglycol ether, ethyl triglycol ether or methyl triglycol ether, or most often of at least one boric ester of a glycol ether such as, for example, the boric ester of methyl triglycol ether or further of a mixture of the two.
  • the amine of the invention is an excellent neutralizing agent.
  • the composition can contain the usual additives of hydraulic fluids.
  • it can contain, in addition to the amine, a corrosion-inhibiting additive, such as benzotriazole, tolyltriazole, an alkali metal or alkaline-earth metal nitrate, triphenyl phosphite, or dodecenylsuccinic anhydride.
  • a corrosion-inhibiting additive such as benzotriazole, tolyltriazole, an alkali metal or alkaline-earth metal nitrate, triphenyl phosphite, or dodecenylsuccinic anhydride.
  • an oxidation-inhibiting additive such as bisphenol A or polymerized trimethylquinoline.
  • composition according to the invention can advantageously contain, by weight:
  • the amine used makes it possible to more particularly obtain compositions having an equilibrium reflux boiling point (E.R.B.P.) equal to or greater than 270°C, e.g. from 270 to 295°C, and simultaneously a kinematic viscosity, measured at - 40°C, equal to or less than 1100 mm2/s, e.g. from 900 to 1100 mm2/s, while having a low volatility which is characterized by a small variation in the pH and in the reserve alkalinity (RA) after having been subjected to an evaporation test. It also makes it possible to obtain compositions having an E.R.B.P. equal to or greater than 300°C, e.g.
  • E.R.B.P. equilibrium reflux boiling point
  • compositions from 300 to 310°C, while having a kinematic viscosity, measured at - 40°C, equal to or less than 1400 mm2/s, e.g. from 1250 to 1400 mm2/s.
  • all these compositions have a pH between 7 and 9 and preferably between 7.5 and 8.5, a good compatibility with elastomers and good corrosion-inhibiting properties, especially with respect to ferrous alloys or metals.
  • composition according to the invention is particularly suited to the manufacture of brake fluids of DOT 3 type (DOT signifying Department of Transportation U.S.A.) and preferably of DOT 4 or DOT 5.1.
  • DOT 3 type DOT signifying Department of Transportation U.S.A.
  • DOT 4 or DOT 5.1 DOT 4 or DOT 5.1.
  • These brake fluids can be used very advantageously in the brake circuits of competition cars, in particular when they have an E.R.B.P. equal to or greater than 300°C.
  • the E.R.B.P. of a hydraulic fluid is measured in °C according to the SAE standard J 1703 of June 1991.
  • the pH of a hydraulic fluid is measured according to SAE standard J 1703 of June 1991.
  • the reserve alkalinity (RA) of a hydraulic fluid is measured by the volume of 0.1 N hydrochloric acid, expressed in ml, necessary to obtain a pH of 5.5 for a 50 ml sample of hydraulic fluid.
  • the following examples illustrate the present invention.
  • compositions were prepared. Table 1 gives the compositions by weight.
  • Composition 1, prepared according to the invention contains 2,2'-[3(methoxypropyl)imino]bisethanol (amine (C)), which was obtained by reacting 3-methoxypropylamine with 2 moles of ethylene oxide.
  • This ether-amine had the following composition by weight :
  • compositions are comparative and were not prepared according to the invention.
  • Table 2 shows, for each of the compositions 1 to 7, the following characteristics :
  • Table 2 also shows the requirements for the characteristics measured. It was observed that Composition 1 made it possible to fulfil all these requirements. Composition 5 had an excessively large swelling of the elastomers, Composition 4 had an excessively low pH and an excessively high viscosity whereas compositions 2, 6 and 7 had an excessively low E.R.B.P.
  • compositions were prepared. Table 3 shows the compositions by weight.
  • Composition 8 prepared according the invention, contained 2,2'-[3(methoxypropyl)imino]bisethanol (amine (C)) used in Example 1.
  • the other compositions are comparative compositions which had not been prepared according to the invention.
  • "additives” means a mixture containing tolyltriazole, triphenyl phosphite and polymerized trimethylquinoline. This mixture is used to obtain a hydraulic fluid containing 200 ppm of tolyltriazole, 0.1 % by weight of triphenyl phosphite and 0.02 % by weight of the polymerized trimethylquinoline.
  • Table 4 shows, for each of the compositions, the following measured characteristics with the requirements:
  • Composition No. 8 made it possible to fulfil all the requirements. Moreover, it shows the following results of SBR swelling tests carried out according to SAE standard J 1703 of June 1991:
  • Composition 9 which contained tridecylamine, had a pH measured after Evaporation Test No. 1 of less than 7 whereas Composition 10 showed an excessively large variation in the reserve alkalinity.
  • Evaporation Test No. 1 was carried out in the following way : 100 ml of hydraulic fluid were introduced into a 600 ml glass beaker. The beaker was then placed for 168 hours in an oven maintained at 140°C.
  • Evaporation Test No. 2 was carried out in the following way: 200 ml of hydraulic fluid were introduced into a 500 ml round-bottomed flask with a ground neck. This roundbottomed flask was placed for 24 hours in an oven maintained at 80°C ⁇ 2°C and under a 2 mm mercury vacuum.
  • compositions in weight % % 1 2 3 4 5 6 7 boric ester of the monomethyl ether of triethylene glycol 95.0 95.5 90.0 91.0 85.8 95.0 95.0 monomethyl ether of triethylene glycol 1.5 6.5 monobutyl ether of triethylene glycol 2.0 8.3 11.0 2.0 2.0 amine (C) 3.0 tributylamine 3.0 tridecylamine 3.2 dioctylamine 3.5 diisopropanolamine 3.0 monoethanolamine 0.7 3-methoxypropylamine 3.0 Characteristics Requirements 1 2 3 4 5 6 7 boron content 1.87 1.88 1.80 1.82 1.88 1.87 1.87 pH from 7 to 11 7.15 7.3 7.45 6.9 7.4 7.5 8.3 ERBP (°C) > 300 308 290 306 300 310 292 261 kinematic viscosity at -40°C(mm 2 / s ) ⁇ 1400 1329 1470 1440 1500 1273 Results of the SBR swelling test variation in the diameter (mm

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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)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Lubricants (AREA)

Claims (10)

  1. Composition de fluide hydraulique à base d'au moins un éther de glycol ou d'au moins un ester borate d'un éther de glycol, ou encore d'un mélange des deux, caractérisée en ce qu'elle contient, à titre d'additif, au moins une éther-amine ayant une masse moléculaire de 120 à 300 et ayant la formule suivante :
    Figure 00150001
    dans laquelle R3 est un radical linéaire ou ramifié ayant au moins un groupe fonctionnel éther et pas de groupe fonctionnel alcool, R est un radical méthyle ou un atome d'hydrogène, p est un entier de 1 à 3 et q est un entier de 0 à 2.
  2. Composition de fluide hydraulique selon la revendication 1, caractérisée en ce que R3 est un groupe de formule R1-O-R2- dans laquelle R1 est un radical alkyle linéaire ou ramifié et R2 est un radical alkylène linéaire ou ramifié.
  3. Composition de fluide hydraulique selon la revendication 2, caractérisée en ce que R1 est un radical alkyle linéaire ou ramifié ayant de 1 à 5 atomes de carbone et R2 est un radical alkylène linéaire ou ramifié ayant de 2 à 8 atomes de carbone.
  4. Composition de fluide hydraulique selon l'une des revendications 1 à 3, caractérisée en ce que l'éther-amine a une masse moléculaire de 150 à 250.
  5. Composition de fluide hydraulique selon l'une des revendications 1 à 4, caractérisée en ce qu'elle contient, en poids, de 0,5 à 5 % de l'éther-amine.
  6. Composition de fluide hydraulique selon l'une des revendications 1 à 5, caractérisée en ce qu'elle a une viscosité, mesurée à 40°C, inférieure à 10 mm2/s.
  7. Composition de fluide hydraulique contenant, en poids :
    a) de 60 à 95 % d'ester borate de l'éther monométhylique de triéthylèneglycol,
    b) de 1 à 15 % d'éther monométhylique de triéthylèneglycol,
    c) de 0 à 15 % d'éther monobutylique de triéthylèneglycol et
    d) de 0,5 à 5 % d'une éther-amine ayant une masse moléculaire de 120 à 300 et ayant la formule suivante :
    Figure 00160001
    dans laquelle R3 est un radical linéaire ou ramifié ayant au moins un groupe fonctionnel éther et pas de groupe fonctionnel alcool, R est un radical méthyle ou un atome d'hydrogène, p est un entier de 1 à 3 et q est un entier de 0 à 2.
  8. Composition de fluide hydraulique selon la revendication 7, caractérisée en ce que R3 est un groupe de formule R1-O-R2- dans laquelle R1 est un radical alkyle linéaire ou ramifié ayant de 1 à 5 atomes de carbone et R2 est un radical alkylène linéaire ou ramifié ayant de 2 à 8 atomes de carbone.
  9. Composition de fluide hydraulique selon l'une des revendications 1 à 8, caractérisée en ce qu'elle a un point d'ébullition au reflux à l'équilibre (E.R.B.P.) égal ou supérieur à 270°C et une viscosité, mesurée à-40°C, égale ou inférieure à 1100 mm2/s.
  10. Composition de fluide hydraulique selon l'une des revendications 1 à 8, caractérisée en ce qu'elle a un point d'ébullition au reflux à l'équilibre (E.R.B.P.) égal ou supérieur à 300°C et une viscosité, mesurée à -40°C, égale ou inférieure à 1400 mm2/s.
EP94301644A 1993-03-17 1994-03-09 Composition de fluide hydraulique Expired - Lifetime EP0617116B1 (fr)

Applications Claiming Priority (2)

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FR9303342 1993-03-17
FR9303342A FR2702772B1 (fr) 1993-03-17 1993-03-17 Composition de fluide hydraulique.

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US6558569B1 (en) 2000-11-10 2003-05-06 Union Carbide Chemicals & Plastics Technology Corporation Low viscosity functional fluids compositions
BRPI0613845A2 (pt) 2005-07-01 2011-02-15 Dow Global Technologies Inc composição de fluìdo funcional e sistema de frenagem para veìculos
WO2010053639A1 (fr) * 2008-11-07 2010-05-14 Dow Global Technologies Inc. Liquides fonctionnels à faible viscosité
EP2850163B1 (fr) * 2012-05-15 2019-03-06 Basf Se Nouvelle composition fluide fonctionnelle de faible viscosité
AU2020343995B2 (en) 2020-04-23 2022-03-03 Clariant International Ltd Low viscosity functional fluid composition
EP3929269A1 (fr) 2020-06-22 2021-12-29 Clariant International Ltd Composition de liquide fonctionnelle peu visqueuse
EP4056669A1 (fr) 2021-03-12 2022-09-14 Clariant International Ltd Composition de liquide fonctionnelle avec une viscosité basse
CN113122357B (zh) * 2021-04-19 2023-01-24 中国石油化工股份有限公司 一种机动车辆制动液组合物及其制备方法
EP4130211A1 (fr) 2021-08-02 2023-02-08 Clariant International Ltd Composition de liquide fonctionnelle peu visqueuse

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US3637794A (en) * 1967-04-13 1972-01-25 Olin Mathieson Borate esters prepared by successive reactions of boric acid with glycol monoethers and polyols
DE1906038C3 (de) * 1969-02-07 1973-11-08 Chemische Werke Huels Ag, 4370 Marl Schmiermittel
JPS5930759B2 (ja) * 1977-05-31 1984-07-28 三洋化成工業株式会社 新規なブレ−キ液組成物
GB2172284B (en) * 1985-03-12 1988-07-27 Ciba Geigy Ag Nitrogen-containing additives for non-aqueous functional fluids
DE68907288T2 (de) * 1988-06-24 1993-10-21 Exxon Chemical Patents Inc Reibungsvermindernde Hydroxyätheramine für Kraftübertragungsflüssigkeiten und Verschleissschutzadditive, die damit verwendbar sind.

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EP0617116A1 (fr) 1994-09-28
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FR2702772B1 (fr) 1995-04-28
ES2141196T3 (es) 2000-03-16
FR2702772A1 (fr) 1994-09-23

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