WO2000065001A1 - Hydraulische flüssigkeiten, enthaltend cyclische carbonsäurederivate - Google Patents
Hydraulische flüssigkeiten, enthaltend cyclische carbonsäurederivate Download PDFInfo
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- WO2000065001A1 WO2000065001A1 PCT/EP2000/003230 EP0003230W WO0065001A1 WO 2000065001 A1 WO2000065001 A1 WO 2000065001A1 EP 0003230 W EP0003230 W EP 0003230W WO 0065001 A1 WO0065001 A1 WO 0065001A1
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- carboxylic acid
- acid derivatives
- weight
- motor vehicles
- brake fluids
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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
-
- 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 hydraulic fluids, in particular brake fluids for motor vehicles, which contain 0.01 to 50% by weight of one or more cyclic carboxylic acid derivatives of the general formula I.
- X represents an oxygen atom or a grouping of the formula NR 1 , where
- R 1 denotes hydrogen or a linear or branched Ci to C 2 o ⁇ alkyl group, which can additionally be interrupted by up to 9 non-adjacent oxygen atoms and / or can carry up to 6 hydroxyl groups, or a cycloalkyl group or an optionally denotes substituted phenyl group,
- A denotes a grouping of the formula -CRR 3 -, where
- R 2 and R 3 represent hydrogen or C 1 -C 6 -alkyl groups, which can additionally be interrupted by up to 4 non-adjacent oxygen atoms and / or can carry up to 3 hydroxyl groups, and
- n a number from 2 to 7
- Hydraulic fluids and especially brake fluids for motor vehicles are subject to very high requirements with regard to their chemical and physical properties.
- According to the existing standards and specifications for brake fluids from the US Department of Transportation in the Federal Motor Vehicle Safety Standard FMVSS-No. 116 and the standard SAE J 1704 published by the Society of Automotive Engineers are intended to modern brake fluids on the one hand via high dry boiling points (reflux boiling points, dry [Equilibrium reflux boiling point. "ERBP”]) and high wet boiling points (reflux boiling points, moist ["wet ERBP”]), but on the other hand also have a viscosity which changes only slightly within a wide temperature range.
- ERBP Equilibrium reflux boiling point
- 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.
- Of particular interest are N-C ⁇ ⁇ to C o-alkylpyrrolidones-2.
- the ring member X preferably represents a grouping of the formula NR 1 .
- 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.
- 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-octadecyl, eicosyl, 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 4-hydroxybutyl, 2-methoxyethyl, 2-methoxypropyl, 3 -Methoxypropyl, 4-methoxybutyl, 2-hydroxy-3-methoxypropyl, 3-hydroxy-2-methoxypropyl
- the radical R 1 preferably denotes hydrogen or a linear or branched C 1 -C 6 -alkyl group, which is additionally interrupted by up to 3 non-adjacent oxygen atoms be 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 in ring sizes of four to six-membered rings.
- the cyclic carboxylic acid derivatives I are known substances which are commercially available or can be synthesized by customary production methods.
- a preferred embodiment of the present invention are brake fluids for motor vehicles which contain 0.01 to 50% by weight of one or more of the cyclic carboxylic acid derivatives I described.
- preferred contents of the compounds I are 0.05 to 30% by weight, in particular 0.1 to 20% by weight, especially 0.5 to 10% by weight, in each case 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 meets the requirements mentioned at the beginning 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 clearly exceeds the more stringent requirements from the automotive industry for a low low-temperature viscosity in the presence of water.
- the compounds I can therefore be used to lower the viscosity, in particular the low-temperature viscosity, in the presence of water in hydraulic fluids or brake fluids for motor vehicles, ie. H. set to a lower level.
- hydraulic fluids and brake fluids for motor vehicles are their favorable corrosion behavior, good water compatibility, a gentle pH value, good resistance to cold, high temperature and oxidation as well as good chemical stability, a favorable behavior towards elastomers and rubber and good lubrication behavior.
- the brake fluids for motor vehicles according to the invention also contain 0.1 to 97% by weight, in particular 30 to 97% by weight, in particular 50 to 97% by weight, in each case based on the total mass of the compounds I Brake fluid, one or more polyglycol ethers and / or their boric acid esters.
- 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. Ethylene glycol or propylene glycol dialkyl ethers with up to 6 alkylene oxide units and each with up to 4 carbon atoms in the alkyl radicals are also suitable.
- Suitable boric acid esters of the polyglycol ethers mentioned or of other polyglycol ethers are particularly described in EP-B 013 925 (cyclic bis-boric acid esters), DE-C 28 04 535 (nitrogen-containing boric acid esters), DE-A 24 38 038 (boric acid-alkylene glycol monoalkyl) - ether esters) and DE-B 17 68 933 (tris-alkoxyalkyl borate) described.
- the brake fluids according to the invention for motor vehicles can also contain, as the main component, those based on carboxylic acid esters, mineral oils or silicone oils.
- the brake fluids for motor vehicles according to the invention contain, in addition to the compounds I, 0.1 to 50% by weight, in particular 1 to 40% by weight, especially 5 to 30% by weight, based in each case on the Ge - 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 normally 2 to 10.
- the effect of these high-boiling polyglycols is that of a lubricant, which is essentially due to an improvement in the temperature-viscosity behavior.
- the polyglycols give the low viscosity polyglycol ethers sufficient viscosity at high temperatures and thus ensure adequate lubrication. Adequate lubrication is therefore necessary in the components of the motor vehicle brake system, since rubber or elastomers on metal have to slide as wear-free as possible.
- the brake fluids for motor vehicles according to the invention contain, in addition to the compounds I, 0.01 to 10% by weight, in particular 0.02 to 6% by weight, especially 0.05 to 4% by weight, in each case based on the total mass of the brake fluid, one or more corrosion inhibitors.
- Corrosion inhibitors in brake fluids have the task of preventing the destruction of metallic materials caused by corrosion.
- the main corrosion inhibitors here are alkali metal salts of phosphoric acid and phosphorous acid, fatty acids such as caprylic, lauric, palmitic, stearic or oleic acid and their alkali metal salts, esters of phosphoric acid and phosphorous acid such as ethyl phosphate, dimethyl phosphate, isopropyl phosphate, diisopropyl phosphate or butisyl Dimethyl phosphite, optionally ethoxylated mono- and dialkylamines and their salts with mineral and fatty acids, for example Butylamine, hexylamine, octylamine, isononylamine, oleylamine, dipropylamine, diisopropylamine or dibutylamine, optionally ethoxylated alkanolamines, e.g.
- Formulations of a conventional motor vehicle brake fluid were produced from the cyclic carboxylic acid derivatives listed below, which are commercially available or can be prepared by customary methods. The corresponding application data for the brake fluids additized in this way were determined.
- the motor vehicle brake fluid BF 1 used without connections I had the following composition:
- methyltriglycol-borate 75% by weight of methyltriglycol-borate, 22% by weight of a mixture of methyldi-methyltri- and methyl-tetraglycol,
- DOT 5.1 Brake Fluid® 900 1265 180 262 It can be seen that the formulations according to the invention, in contrast to conventional DOT 5.1 brake fluids such as BF 1, Hydraulan 508 from BASF Aktiengesellschaft or DOT 5.1 Brake Fluid from Motul SA (France), in addition to the requirements of the DOT 5.1 specification beyond that
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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)
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT00922626T ATE243248T1 (de) | 1999-04-22 | 2000-04-11 | Hydraulische flüssigkeiten, enthaltend cyclische carbonsäurederivate |
DE50002594T DE50002594D1 (de) | 1999-04-22 | 2000-04-11 | Hydraulische flüssigkeiten, enthaltend cyclische carbonsäurederivate |
KR1020017013231A KR100660953B1 (ko) | 1999-04-22 | 2000-04-11 | 고리계 카르복실산 유도체를 함유하는 유압유 |
CA002367913A CA2367913C (en) | 1999-04-22 | 2000-04-11 | Hydraulic fluids containing cyclic carboxylic derivatives |
US09/959,160 US6783693B1 (en) | 1999-04-22 | 2000-04-11 | Hydraulic fluids, containing cyclic carboxylic acid derivatives |
EP00922626A EP1171552B1 (de) | 1999-04-22 | 2000-04-11 | Hydraulische flüssigkeiten, enthaltend cyclische carbonsäurederivate |
JP2000614340A JP2002543238A (ja) | 1999-04-22 | 2000-04-11 | 環式カルボン酸誘導体を含有する圧媒液 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19918199A DE19918199A1 (de) | 1999-04-22 | 1999-04-22 | Hydraulische Flüssigkeiten, enthaltend cyclische Carbonsäurederivate |
DE19918199.3 | 1999-04-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000065001A1 true WO2000065001A1 (de) | 2000-11-02 |
Family
ID=7905435
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2000/003230 WO2000065001A1 (de) | 1999-04-22 | 2000-04-11 | Hydraulische flüssigkeiten, enthaltend cyclische carbonsäurederivate |
Country Status (10)
Country | Link |
---|---|
US (1) | US6783693B1 (de) |
EP (1) | EP1171552B1 (de) |
JP (1) | JP2002543238A (de) |
KR (1) | KR100660953B1 (de) |
AT (1) | ATE243248T1 (de) |
CA (1) | CA2367913C (de) |
DE (2) | DE19918199A1 (de) |
ES (1) | ES2202113T3 (de) |
PT (1) | PT1171552E (de) |
WO (1) | WO2000065001A1 (de) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013171052A1 (en) | 2012-05-15 | 2013-11-21 | Basf Se | Novel low viscosity functional fluid composition |
WO2015052234A1 (en) | 2013-10-10 | 2015-04-16 | Basf Se | Novel functional fluid composition |
WO2021213693A1 (en) | 2020-04-23 | 2021-10-28 | Clariant International Ltd | Low viscosity functional fluid composition |
EP3929269A1 (de) | 2020-06-22 | 2021-12-29 | Clariant International Ltd | Funktionale fluidzusammensetzung mit niedriger viskosität |
EP4056669A1 (de) | 2021-03-12 | 2022-09-14 | Clariant International Ltd | Niedrigviskose funktionsflüssigkeitszusammensetzung |
EP4130211A1 (de) | 2021-08-02 | 2023-02-08 | Clariant International Ltd | Funktionale fluidzusammensetzung mit niedriger viskosität |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004074547A2 (en) * | 2003-02-19 | 2004-09-02 | Intellectual Concepts, Llc | Lower alkyl carboxylic acid moiety-containing anti- corrosion compositions and methods of use. |
US20130310286A1 (en) * | 2012-05-15 | 2013-11-21 | Basf Se | Novel low viscosity functional fluid composition |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2209830A1 (en) * | 1972-12-12 | 1974-07-05 | Basf Ag | Hydraulic and brake fluids - of glycol or glycol ether type, contg N-alkyl pyrrolidones for improved lubrication |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
JPS5046584A (de) | 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 |
-
1999
- 1999-04-22 DE DE19918199A patent/DE19918199A1/de not_active Withdrawn
-
2000
- 2000-04-11 WO PCT/EP2000/003230 patent/WO2000065001A1/de active IP Right Grant
- 2000-04-11 US US09/959,160 patent/US6783693B1/en not_active Expired - Fee Related
- 2000-04-11 AT AT00922626T patent/ATE243248T1/de active
- 2000-04-11 DE DE50002594T patent/DE50002594D1/de not_active Expired - Lifetime
- 2000-04-11 PT PT00922626T patent/PT1171552E/pt unknown
- 2000-04-11 JP JP2000614340A patent/JP2002543238A/ja active Pending
- 2000-04-11 EP EP00922626A patent/EP1171552B1/de not_active Expired - Lifetime
- 2000-04-11 KR KR1020017013231A patent/KR100660953B1/ko not_active IP Right Cessation
- 2000-04-11 CA CA002367913A patent/CA2367913C/en not_active Expired - Fee Related
- 2000-04-11 ES ES00922626T patent/ES2202113T3/es not_active Expired - Lifetime
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2209830A1 (en) * | 1972-12-12 | 1974-07-05 | Basf Ag | Hydraulic and brake fluids - of glycol or glycol ether type, contg N-alkyl pyrrolidones for improved lubrication |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013171052A1 (en) | 2012-05-15 | 2013-11-21 | Basf Se | Novel low viscosity functional fluid composition |
WO2015052234A1 (en) | 2013-10-10 | 2015-04-16 | Basf Se | Novel functional fluid composition |
US10941367B2 (en) | 2013-10-10 | 2021-03-09 | Basf Se | Functional fluid composition |
WO2021213693A1 (en) | 2020-04-23 | 2021-10-28 | Clariant International Ltd | Low viscosity functional fluid composition |
EP3929269A1 (de) | 2020-06-22 | 2021-12-29 | Clariant International Ltd | Funktionale fluidzusammensetzung mit niedriger viskosität |
WO2021259514A1 (en) | 2020-06-22 | 2021-12-30 | Clariant International Ltd | Low viscosity functional fluid composition |
EP4056669A1 (de) | 2021-03-12 | 2022-09-14 | Clariant International Ltd | Niedrigviskose funktionsflüssigkeitszusammensetzung |
WO2022189047A1 (en) | 2021-03-12 | 2022-09-15 | Clariant International Ltd | Low viscosity functional fluid composition |
EP4130211A1 (de) | 2021-08-02 | 2023-02-08 | Clariant International Ltd | Funktionale fluidzusammensetzung mit niedriger viskosität |
WO2023011801A1 (en) | 2021-08-02 | 2023-02-09 | Clariant International Ltd | Low viscosity functional fluid composition |
Also Published As
Publication number | Publication date |
---|---|
JP2002543238A (ja) | 2002-12-17 |
KR100660953B1 (ko) | 2006-12-26 |
US6783693B1 (en) | 2004-08-31 |
ATE243248T1 (de) | 2003-07-15 |
PT1171552E (pt) | 2003-10-31 |
ES2202113T3 (es) | 2004-04-01 |
DE19918199A1 (de) | 2000-10-26 |
DE50002594D1 (de) | 2003-07-24 |
CA2367913A1 (en) | 2000-11-02 |
EP1171552A1 (de) | 2002-01-16 |
EP1171552B1 (de) | 2003-06-18 |
CA2367913C (en) | 2008-01-08 |
KR20020010606A (ko) | 2002-02-04 |
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