EP1171552B1 - Liquides hydrauliques contenant des derives cycliques d'acide carboxylique - Google Patents

Liquides hydrauliques contenant des derives cycliques d'acide carboxylique Download PDF

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Publication number
EP1171552B1
EP1171552B1 EP00922626A EP00922626A EP1171552B1 EP 1171552 B1 EP1171552 B1 EP 1171552B1 EP 00922626 A EP00922626 A EP 00922626A EP 00922626 A EP00922626 A EP 00922626A EP 1171552 B1 EP1171552 B1 EP 1171552B1
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Prior art keywords
carboxylic acid
acid derivatives
cyclic carboxylic
group
formula
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EP00922626A
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German (de)
English (en)
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EP1171552A1 (fr
Inventor
Bayram Aydin
Uwe Fidorra
Arthur Höhn
Ladislaus Meszaros
Jan Nouwen
Knut Oppenländer
Michael Roida
Michael Stösser
Bernd Wenderoth
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BASF SE
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BASF SE
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    • C10M2215/226—Morpholines
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/30—Heterocyclic compounds
    • 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
    • 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

  • FR-A 2 209 830 (corresponds to DE-B 2 260 701) discloses the Use of cyclic carboxylic acid derivatives in the form of N-alkylpyrrolidones in hydraulic fluids in an amount of 20 to 60 wt .-% to reduce wear and improve the lubricating properties.
  • Hydraulic fluids and especially brake fluids for motor vehicles are subject with regard to their chemical and physical properties very high requirements.
  • brake fluids from the U.S. Department of Transportation in the Federal Motor Vehicle Safety Standard FMVSS no. 116 and that of the Society of Automotive Engineers published standard SAE J 1704 are said to be modern Brake fluids on the one hand have high dry boiling points (Reflux boiling points, dry [Equilibrium reflux boiling point, "ERBP”]) and high wet boiling points (reflux points, moist ["wet ERBP”]), but also a viscosity have, which are within a wide temperature range little changes. There are also further requirements from the automotive industry after a low Low temperature viscosity in the presence of water.
  • cyclic carboxylic acid derivatives of the general formula I are, in particular, cyclic carboxamides (lactams) and cyclic carboxylic acid esters (lactones), which can serve as precursors in the preparation of the first-mentioned lactams.
  • lactones cyclic carboxylic acid esters
  • Five- and six-membered ring systems can be used as particularly preferred ring sizes.
  • NC 1 to C 20 alkyl pyrrolidones-2 are particularly preferred ring sizes.
  • the ring member X preferably represents a grouping of the formula NR 1 .
  • the radical R 1 denotes, for example, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, iso-pentyl, sec-pentyl , tert-pentyl, neo-pentyl, n-hexyl, cyclohexyl, phenyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, iso-nonyl, n-decyl, iso-decyl, n-undecyl, n-dodecyl, n-tridecyl, iso-tridecyl, n-tetradecyl, n-hexydecyl, n-octa
  • the radical R 1 preferably denotes hydrogen or a linear or branched C 1 -C 6 -alkyl group, which can additionally be interrupted by up to 3 non-adjacent oxygen atoms and / or can carry up to 2 hydroxyl groups, or a cyclohexyl or phenyl group ,
  • R 1 can serve as examples of R 2 and R 3 .
  • R 2 and R 3 are preferably hydrogen or methyl groups, especially hydrogen.
  • n is preferably 2, 3 or 4; this would result Ring sizes from four to six-membered rings.
  • the cyclic carboxylic acid derivatives I are known substances, which are commercially available or according to common manufacturing methods can be synthesized.
  • the brake fluids contain for motor vehicles 0.01 to 10 wt .-% of one or more of the described cyclic carboxylic acid derivatives I. Both for hydraulic Liquids as well as brake fluids for motor vehicles are preferred contents of the compounds I 0.5 to 10% by weight, based on the total mass of the hydraulic fluid or brake fluid.
  • the presence of the compounds I ensures in an excellent manner that the hydraulic fluid or brake fluid for Motor vehicles meet the requirements mentioned above and in addition to those for brake fluids from the US Department of Transportation in the Federal Motor Vehicle Safety Standard FMVSS no. 116 specified requirements of the specifications DOT 5 and DOT 5.1 for silicone-free brake fluids, also the tightened ones Requirements from among the automotive industry a low low temperature viscosity in the presence of water clearly exceeds.
  • the compounds I can therefore be used in hydraulic fluids or brake fluids for motor vehicles the viscosity, in particular the Low temperature viscosity in the presence of water, to decrease d. H. set to a lower level.
  • Suitable polyglycol ethers are especially ethylene glycol monoalkyl ethers with up to 6 ethylene oxide units and with up to 4 Carbon atoms in the alkyl radical. There are also ethylene glycol or Propylene glycol dialkyl ether with up to 6 alkylene oxide units and each with up to 4 carbon atoms in the alkyl radicals into consideration.
  • Suitable boric acid esters of those mentioned or of other polyglycol ethers are described in particular in documents EP-B 013 925 (cyclic Bis-boric acid ester), DE-C 28 04 535 (nitrogen-containing boric acid ester), DE-A 24 38 038 (boric acid-alkylene glycol monoalkyl ether ester) and DE-B 17 68 933 (tris-alkoxyalkyl borate) described.
  • the brake fluids according to the invention for motor vehicles as the main component also those based on carboxylic acid esters, Contain mineral oils or silicone oils.
  • the brake fluids used for motor vehicles according to the invention contained in a further preferred embodiment in addition to the compounds I further 0.1 to 50 wt .-%, in particular 1 to 40 wt .-%, especially 5 to 30 wt .-%, each based on the total mass of the brake fluid, one or more polyglycols.
  • Suitable polyglycols are above all higher-boiling reaction products of ethylene oxide and / or propylene oxide and / or butylene oxide with water or diols, in particular corresponding reaction products of mixtures of ethylene oxide and propylene oxide with water are used.
  • the number of alkylene oxide units in such polyglycols is usually 2 to 10.
  • the effect of these high-boiling polyglycols is one Lubricant, which essentially indicates an improvement in the Temperature-viscosity behavior is attributable.
  • the polyglycols give the thin polyglycol ethers at high Temperatures sufficient viscosity and thus ensure sufficient Lubrication. Sufficient lubrication is therefore in the components of the motor vehicle braking system necessary because there Glide rubber or elastomers on metal as wear-free as possible have to.
  • the brake fluids used for motor vehicles according to the invention contained in a further preferred embodiment in addition to the compounds I further 0.01 to 10 wt .-%, in particular 0.02 to 6 wt .-%, especially 0.05 to 4 wt .-%, each based on the total mass of the brake fluid, one or more Corrosion inhibitors.
  • Corrosion inhibitors in brake fluids have the task the destruction of metallic materials caused by corrosion to prevent.
  • corrosion inhibitors especially alkali metal salts of phosphoric acid and phosphorous Acid, fatty acids such as caprylic, lauric, palmitic, stearic or Oleic acid and its alkali metal salts, esters of phosphoric acid and the phosphorous acid such as ethyl phosphate, dimethyl phosphate, Isopropyl phosphate, diisopropyl phosphate, butyl phosphite or dimethyl phosphite, optionally ethoxylated mono- and dialkylamines and their salts with mineral and fatty acids, e.g.
  • butylamine Hexylamine, octylamine, isononylamine, oleylamine, dipropylamine, Diisopropylamine or dibutylamine, optionally ethoxylated Alkanolamines, e.g. Mono-, di- or triethanolamine, N, N'-din-butylaminoethanol or 1,1'-iminodipropan-2-ol, cyclohexylamine, Triazoles such as benzo- or tolutriazole and nitroaromatics, e.g. 3-nitrobenzaldehyde.
  • Alkanolamines e.g. Mono-, di- or triethanolamine, N, N'-din-butylaminoethanol or 1,1'-iminodipropan-2-ol, cyclohexylamine, Triazoles such as benzo- or tolutriazole and nitroaromatics, e.g. 3-nitrobenzaldehy
  • Brake fluids for motor vehicles can contain common antioxidants, e.g. those based on phenol, and conventional defoamers his.
  • the motor vehicle brake fluid BF 1 used without connections I had the following composition: 75% by weight Methyltriglycol-borate, 22% by weight a mixture of methyldi, methyltri and methyltetraglycol, ⁇ 3% by weight a mixture of N, N'-di-n-butylaminoethanol, 1,1'-iminodipropan-2-ol, tolutriazole and 3-nitrobenzaldehyde ⁇ 0.5% by weight Bisphenol A
  • BF 1 starting 5 wt .-% methyl triglycol against 5 wt .-% of cyclic carboxylic acid derivatives used according to the invention.

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (10)

  1. Utilisation d'un ou plusieurs dérivés d'acides carboxyliques cycliques de formule générale I
    Figure 00150001
    dans laquelle
    X est un atome d'oxygène ou un groupement de formule N-R1, où
    R1 est un atome d'hydrogène ou un groupe alkyle en C1-C20 à chaíne droite ou ramifiée, qui peut encore et en outre être interrompue par jusqu'à 9 atomes d'oxygène non voisins et/ou porter jusqu'à 6 groupes hydroxyle, ou encore désigne un groupe cycloalkyle ou un groupe phényle éventuellement substitué,
    A désigne un groupement de formule -CR2R3-, où
    R2 et R3 représentent chacun un atome d'hydrogène ou un groupe alkyle en C1-C8, qui peut encore et en outre être interrompu par jusqu'à 4 atomes d'oxygène non voisins et/ou porter jusqu'à 3 groupes hydroxyle, et
    n est un nombre de 2 à 7,
       dans des fluides hydrauliques, en une quantité de 0,01 à 10 % en poids, pour abaisser la viscosité, en particulier la viscosité à basse température en présence d'eau.
  2. Utilisation de dérivés d'acides carboxyliques cycliques I, dans lesquels X est un groupement de formule N-R1 selon la revendication 1.
  3. Utilisation de dérivés d'acides carboxyliques cycliques I, dans lesquels R1 est un atome d'hydrogène ou un groupe alkyle en C1-C6 à chaíne droite ou ramifiée, qui peut encore et en outre être interrompu jusqu'à 3 atomes d'oxygène voisins et/ou porter jusqu'à 2 groupes hydroxyle, selon la revendication 1 ou 2.
  4. Utilisation de dérivés d'acides carboxyliques cycliques I, dans lesquels R2 et R3 sont des atomes d'hydrogène ou des groupes méthyle, selon les revendications 1 à 3.
  5. Utilisation de dérivés d'acides carboxyliques cycliques I, dans lesquels n représente le nombre 2, 3 ou 4, selon les revendications 1 à 4.
  6. Utilisation de dérivés d'acides carboxyliques cycliques I selon les revendications 1 à 5, en tant que liquides de frein pour des véhicules à moteur, en une quantité de 0,1 à 10 % en poids.
  7. Utilisation de dérivés d'acides carboxyliques cycliques I selon la revendication 6, pour laquelle les liquides de frein contiennent, outre les composés I, de 0,1 à 97 % en poids d'un ou plusieurs éthers de polyglycol et/ou leurs esters de l'acide borique.
  8. Utilisation de dérivés d'acides carboxyliques cycliques I selon la revendication 6 ou 7, pour laquelle les liquides de frein contiennent, outre les composés I, de 0,1 à 50 % en poids d'un ou plusieurs polyglycols.
  9. Utilisation de dérivés d'acides carboxyliques cycliques I selon les revendications 6 à 8, pour laquelle les liquides de frein contiennent, outre les composés I, de 0,01 à 10 % en poids d'un ou plusieurs inhibiteurs de corrosion.
  10. Fluides hydrauliques, contenant de 0,01 à 10 % en poids d'un ou plusieurs dérivés d'acides carboxyliques cycliques de formule générale I
    Figure 00160001
    dans laquelle
    X est un atome d'oxygène ou un groupement de formule N-R1, où
    R1 est un groupe alkyle en C1-C20 à chaíne droite ou ramifiée, qui peut encore et en outre être interrompue par jusqu'à 9 atomes d'oxygène non voisins et/ou porter jusqu'à 6 groupes hydroxyle, ou encore désigne un groupe cycloalkyle ou un groupe phényle éventuellement substitué,
    A désigne un groupement de formule -CR2R3-, où
    R2 et R3 représentent chacun un atome d'hydrogène ou un groupe alkyle
    en C1-C8, qui peut encore et en outre être interrompu par jusqu'à 4 atomes d'oxygène non voisins et/ou porter jusqu'à 3 groupes hydroxyle, et
       n est un nombre de 2 à 7.
EP00922626A 1999-04-22 2000-04-11 Liquides hydrauliques contenant des derives cycliques d'acide carboxylique Expired - Lifetime EP1171552B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19918199A DE19918199A1 (de) 1999-04-22 1999-04-22 Hydraulische Flüssigkeiten, enthaltend cyclische Carbonsäurederivate
DE19918199 1999-04-22
PCT/EP2000/003230 WO2000065001A1 (fr) 1999-04-22 2000-04-11 Liquides hydrauliques contenant des derives cycliques d'acide carboxylique

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EP1171552A1 EP1171552A1 (fr) 2002-01-16
EP1171552B1 true EP1171552B1 (fr) 2003-06-18

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EP (1) EP1171552B1 (fr)
JP (1) JP2002543238A (fr)
KR (1) KR100660953B1 (fr)
AT (1) ATE243248T1 (fr)
CA (1) CA2367913C (fr)
DE (2) DE19918199A1 (fr)
ES (1) ES2202113T3 (fr)
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WO2004074547A2 (fr) * 2003-02-19 2004-09-02 Intellectual Concepts, Llc Fractions d'acide carboxylique renfermant un alkyle inferieur utilisees comme stabilisateurs et conservateurs organoleptiques pour aliments et boissons et permettant d'empecher la corrosion par oxydation des metaux
US20130310286A1 (en) * 2012-05-15 2013-11-21 Basf Se Novel low viscosity functional fluid composition
EP2850163B1 (fr) 2012-05-15 2019-03-06 Basf Se Nouvelle composition fluide fonctionnelle de faible viscosité
CN105637075B (zh) 2013-10-10 2019-01-04 巴斯夫欧洲公司 新的功能性流体组合物
KR102618845B1 (ko) 2020-04-23 2023-12-29 클라리언트 인터내셔널 리미티드 저점도 기능성 유체 조성물
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
EP4130211A1 (fr) 2021-08-02 2023-02-08 Clariant International Ltd Composition de liquide fonctionnelle peu visqueuse

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US3334048A (en) * 1963-01-17 1967-08-01 Castrol Ltd Hydraulic fluids
US3637794A (en) 1967-04-13 1972-01-25 Olin Mathieson Borate esters prepared by successive reactions of boric acid with glycol monoethers and polyols
GB1323061A (en) * 1969-06-16 1973-07-11 Castrol Ltd Functional fluids and additives therefor
DE2260701C2 (de) * 1972-12-12 1974-09-12 Basf Ag, 6700 Ludwigshafen Hydraulikflüssigkeiten
JPS5046584A (fr) 1973-08-11 1975-04-25
DE2804535C2 (de) 1978-02-03 1984-04-26 Alfred Teves Gmbh, 6000 Frankfurt Hydraulische Flüssigkeiten
DE2901835A1 (de) 1979-01-18 1980-07-31 Hoechst Ag Hydraulische fluessigkeiten
US4461713A (en) * 1983-04-01 1984-07-24 Stauffer Chemical Company Acid-resistant phosphate ester functional fluids

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PT1171552E (pt) 2003-10-31
ES2202113T3 (es) 2004-04-01
KR100660953B1 (ko) 2006-12-26
DE19918199A1 (de) 2000-10-26
CA2367913A1 (fr) 2000-11-02
JP2002543238A (ja) 2002-12-17
EP1171552A1 (fr) 2002-01-16
WO2000065001A1 (fr) 2000-11-02
KR20020010606A (ko) 2002-02-04
US6783693B1 (en) 2004-08-31
CA2367913C (fr) 2008-01-08
DE50002594D1 (de) 2003-07-24

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