WO2002083607A2 - Huile hydraulique stable a l'oxydation - Google Patents

Huile hydraulique stable a l'oxydation Download PDF

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Publication number
WO2002083607A2
WO2002083607A2 PCT/EP2002/003048 EP0203048W WO02083607A2 WO 2002083607 A2 WO2002083607 A2 WO 2002083607A2 EP 0203048 W EP0203048 W EP 0203048W WO 02083607 A2 WO02083607 A2 WO 02083607A2
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WO
WIPO (PCT)
Prior art keywords
dgf
synthetic
esters
hydraulic oil
weight
Prior art date
Application number
PCT/EP2002/003048
Other languages
German (de)
English (en)
Other versions
WO2002083607A3 (fr
Inventor
Frank Bongardt
Ralf Christoph
Original Assignee
Cognis Deutschland Gmbh & Co. Kg
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Cognis Deutschland Gmbh & Co. Kg filed Critical Cognis Deutschland Gmbh & Co. Kg
Priority to US10/473,054 priority Critical patent/US20040147411A1/en
Priority to CA002442236A priority patent/CA2442236A1/fr
Priority to EP02742861A priority patent/EP1373443A2/fr
Publication of WO2002083607A2 publication Critical patent/WO2002083607A2/fr
Publication of WO2002083607A3 publication Critical patent/WO2002083607A3/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
    • C07C69/58—Esters of straight chain acids with eighteen carbon atoms in the acid moiety
    • 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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/38—Esters of polyhydroxy 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
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C10M2207/2835—Esters of polyhydroxy compounds 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/288—Partial esters containing free carboxyl groups
    • 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
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • 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
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/223—Five-membered rings containing nitrogen and carbon only
    • 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
    • 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
    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/013—Iodine value
    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/04—Molecular weight; Molecular weight distribution
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/04—Detergent property or dispersant property
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/18—Anti-foaming property
    • 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
    • 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
    • C10N2040/12—Gas-turbines
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

Definitions

  • the present application relates to oxidation-stable hydraulic oils which contain certain synthetic esters based on polyols and unsaturated fatty acids and the use of certain additive packages to improve the oxidation stability of hydraulic oils.
  • Hydraulic systems are used in a large number of technical devices, for example automobiles, trucks, cranes, trains and other means of transport, but also in agricultural devices, ships as well as in industrial companies and in the railway sector.
  • the hydraulic systems generally contain a hydraulic fluid which traditionally contains petrochemical fluids or esters or other oleochemicals as the base fluid. The latter are increasingly preferred due to their biodegradability.
  • polyol esters of fatty acids are known from the prior art as suitable base liquids for hydraulic oils.
  • suitable base liquids for hydraulic oils for example, WO 97/39086 discloses esters which are obtained by reacting polyols, including trimethylolpropane, with mixtures of fatty acids, the ratio of short-chain fatty acids to long-chain fatty acids being in the range from 2: 1 to 1:20.
  • the esters claimed should have advantageous technical properties, in particular because of their low-temperature compatibility.
  • ester systems and hydraulic fluids must also have high oxidation stability, which is particularly important when the hydraulic oil is exposed to high temperatures in the presence of atmospheric oxygen.
  • antioxidants are added to the hydraulic oils as customary additives.
  • the decisive factor in this case is the so-called modified, "Turbine oxidation stability test", or dryer TOST for short, in accordance with DIN51587, which tests the stability of test oils when aged at 95 ° C in the presence of oxygen.
  • Conventional systems already reach the critical limit of 2.0 mg KOH / g test oil after 170 to about 300 hours.
  • the present application therefore relates to synthetic esters
  • R 1 represents a hydrogen atom, a methyl radical or a hydroxyl group
  • R 2 and R 3 independently of one another represent a methyl radical or a CH2-OH group, with the proviso that at least two hydroxyl groups must be present in the molecule
  • the synthetic esters have an iodine number (according to DGF-C-V 11b) from 65 to 100, a saponification number (according to DGf C-V 3) in the range from 160 to 200 and an acid number (according to DGF C-V 2) from a maximum of 3.
  • the synthetic esters according to the invention are prepared in a manner known per se by reacting the polyols with the unsaturated fatty acids in the presence of suitable catalysts and at an elevated temperature. The reaction products can then be removed from the batch by distillation.
  • Such synthetic esters are particularly preferred which have a kinematic viscosity at 40 ° C. of 40 to 70 mm / sec. and at 100 ° C a kinematic viscosity measured according to DIN 51562 of 5 to 20 mm 2 / sec. exhibit.
  • the polyols which are used to prepare the synthetic esters are preferably selected from the group consisting of neopentyl glycol, trimethylolpropane, trimethylolethane and / or pentaerythritol.
  • the use of trimethylolpropane as a starting point for the preparation of the synthetic esters according to the invention is particularly preferred.
  • the fatty acids with 16 to 18 carbon atoms, which together with the polyols according to a) synthetic esters are preferably derived from oleic acid with its different qualities.
  • the esters according to the invention are further characterized in that their acid number measured according to DGF C-V2 at max. 3, preferably ax. 2 mg KOH / g.
  • the iodine number measured according to DGF C-V11B should preferably be in the range from 65 to 100, but in particular in the range from 65 to 90 and very particularly preferably in the range from 70 to 90 mg KOH / g.
  • the saponification numbers measured according to DGF CV should preferably be less than 200 and in particular in the range from 160 to 190 and in particular in the range from 170 to 185 mg KOH / g.
  • the cloud point, measured according to DGF D-Ill 3 is preferably in the range from -40 to -20 ° C. in the esters according to the invention.
  • the water content according to Karl Fischer (DGF C-Ill 13a) is preferably in the range of max. 0.1 and preferably in the range of 0.01 to 0.05.
  • esters according to the invention are the pour point (DIN 3016), which is preferably at most - 30 ° C.
  • the cloud point according to DIN EN 23015 is preferably at most - 20 ° C.
  • the esters according to the invention are not only stable to oxidation but also Stable for several years even at normal storage temperature.
  • Another object of the present application relates to a process for the preparation of synthetic polyol and complex esters, wherein polyols of the general formula (I) are reacted with so-called oleins at temperatures of> 200 ° C. for at least 3 hours with a nitrogen atmosphere and then in reduced pressure removes the excess fatty acid by distillation.
  • the oleins used in the process according to the invention are technical mixtures of unsaturated and saturated fatty acids which, however, predominantly contain oleic acid. Such oleins are obtained from naturally occurring fats and oils, especially animal oils. Oleins which are obtained by the process of DE 197 36 737 A1 are preferably used for the preparation of the esters according to the invention.
  • such oleins have an iodine number, measured according to DGF CV 11B, in the range from 60 to 130 and a cloud point, measured according to DGF C III, of less than 11 ° C., the oleines furthermore comprising more than 65% by weight of oleic acid and must contain less than 20% by weight of linoleic acid.
  • the present application further claims a hydraulic oil containing 90 to 99% by weight, preferably 95 to 99% by weight and in particular 97 to 99% by weight of a synthetic ester as described above and 1 to 10% by weight of additives .
  • additives are the classes known in principle to the person skilled in the art, namely antioxidants, extreme pressure (EP) or anti-wear (AW) additives, corrosion inhibitors, demugators and / or defoamers. Nonferrous metal deactivators may also be present.
  • the additives are in usual quantities, but in total in max. Contain 10% by weight, preferably 1 to 3% by weight, based on the total weight of the hydraulic oil.
  • the EP / AW additives are in amounts of preferably 0.2 to 2.0% by weight, antioxidants in the range of 0.2 to 1.0% by weight, corrosion protection additives in the range of 0.05 to 0.2 % By weight, non-ferrous metal deactivators in the range from 0.05 to 0.5 and antifoam additives defoamers in the range from 0.005 to 0.04% in the hydraulic oils according to the invention.
  • Such hydraulic oils are formulated by mixing the base liquid with the additives, if necessary at elevated temperature.
  • an additive containing alkylamines, tolyltriazole, alkylphosphate and / or succinic acid semiesters and their derivatives to the hydraulic oils according to the invention.
  • Such additives are preferably contained in a total amount of 0.5 to 2% by weight.
  • Additin RC 9308 has been particularly preferred.
  • This additive contains C12-C14 tertiary alkyl amines, tolyltriazole, tri-n-butyl phosphate and tetrapropylene succinic acid semiesters.
  • the combination of this additive with the synthetic hydraulic oil results in a particularly oxidation-stable end product.
  • Another object of the present application therefore relates to the use of such an additive package to improve the oxidation stability of polyol esters of the above description.
  • esters according to the invention and the hydraulic oils formulated therefrom show a surprisingly high stability TOST test.
  • the so-called “dry” TOST test in which water is no longer present, is used in particular.
  • the TMP ester had the following key figures:
  • a hydraulic oil was examined, containing 98% by weight of TMP ester from the 1st and 2% by weight of an additive package, containing C12-14 alkylamines, tolyltriazole, tri-n-butyl phosphate and tetrapropenylsuccinic acid alkyl half-ester (Additin RC 9308 - a commercial product from the company Rhein Chemie).
  • the above hydraulic oil was subjected to a modified turbine oxidation stability test "TOST" according to DIN 51587 in order to determine the oxidation stability of the hydraulic oil.
  • TOST turbine oxidation stability test
  • the test was carried out in the absence of water. The water was replaced with the same amount of test oil.
  • the test oil is aged in the presence of steel and copper wire with the introduction of oxygen at 95 ° C. The end point of aging is either reached at a neutralization number of 2.0 mg KOH / g oil or, if this value has not yet been reached after 1000 h, the value measured after 1000 h is given.
  • the neutralization number was 1.9 after 1000 h. Only after 1414 h was a neutralization number of 2.0 and thus the final state of aging reached.

Abstract

L'invention concerne des huiles hydrauliques stables à l'oxydation, pouvant être obtenues par estérification de polyols à l'aide d'acide oléique et, éventuellement, par ajout d'additifs. Selon cette invention, les huiles hydrauliques correspondantes satisfont aux exigences de l'essai d'oxydation des huiles inhibées pour turbines selon la norme DIN 51587.
PCT/EP2002/003048 2001-03-29 2002-03-20 Huile hydraulique stable a l'oxydation WO2002083607A2 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US10/473,054 US20040147411A1 (en) 2001-03-29 2002-03-20 Oxidation-stable hydraulic oil
CA002442236A CA2442236A1 (fr) 2001-03-29 2002-03-20 Huile hydraulique stable a l'oxydation
EP02742861A EP1373443A2 (fr) 2001-03-29 2002-03-20 Huile hydraulique stable a l'oxydation

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10115829.7 2001-03-29
DE10115829A DE10115829A1 (de) 2001-03-29 2001-03-29 Oxidationsstabiles Hydrauliköl

Publications (2)

Publication Number Publication Date
WO2002083607A2 true WO2002083607A2 (fr) 2002-10-24
WO2002083607A3 WO2002083607A3 (fr) 2003-01-09

Family

ID=7679714

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2002/003048 WO2002083607A2 (fr) 2001-03-29 2002-03-20 Huile hydraulique stable a l'oxydation

Country Status (5)

Country Link
US (1) US20040147411A1 (fr)
EP (1) EP1373443A2 (fr)
CA (1) CA2442236A1 (fr)
DE (1) DE10115829A1 (fr)
WO (1) WO2002083607A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2228425A1 (fr) * 2009-02-27 2010-09-15 Dako Ag Lubrifiant

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1958931A1 (fr) * 2007-02-02 2008-08-20 Cognis IP Management GmbH Esters d'acides carboxyliques stables à l'oxidation et leur utilisation

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2063909A (en) * 1979-11-29 1981-06-10 Mobil Oil Corp High flashpoint hydraulic fluid
GB2134538A (en) * 1983-01-20 1984-08-15 Idemitsu Kosan Co Lubricating oils
EP0612831A1 (fr) * 1992-12-07 1994-08-31 Idemitsu Kosan Company Limited Huile hydraulique ignifuge
EP0652280A2 (fr) * 1993-10-15 1995-05-10 Oronite Japan Limited Fluide fonctionnel à usage multiple pour machine agricole ou engin de construction
US5614483A (en) * 1994-10-05 1997-03-25 Rhein Chemie Rheinau Gmbh Stabilized lubricant base material
WO1997033954A1 (fr) * 1996-03-12 1997-09-18 Voitelukeskus Tonttila Oy Huile hydraulique et son procede de fabrication
WO1997039086A1 (fr) * 1996-04-16 1997-10-23 Unichema Chemie B.V. Fluides hydrauliques
EP0902006A2 (fr) * 1997-08-25 1999-03-17 Henkel Kommanditgesellschaft auf Aktien Oléines stables à l'oxydation
EP0997519A1 (fr) * 1998-09-29 2000-05-03 Nippon Mitsubishi Oil Corporation Huile pour machine réfrigérante

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5652201A (en) * 1991-05-29 1997-07-29 Ethyl Petroleum Additives Inc. Lubricating oil compositions and concentrates and the use thereof

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2063909A (en) * 1979-11-29 1981-06-10 Mobil Oil Corp High flashpoint hydraulic fluid
GB2134538A (en) * 1983-01-20 1984-08-15 Idemitsu Kosan Co Lubricating oils
EP0612831A1 (fr) * 1992-12-07 1994-08-31 Idemitsu Kosan Company Limited Huile hydraulique ignifuge
EP0652280A2 (fr) * 1993-10-15 1995-05-10 Oronite Japan Limited Fluide fonctionnel à usage multiple pour machine agricole ou engin de construction
US5614483A (en) * 1994-10-05 1997-03-25 Rhein Chemie Rheinau Gmbh Stabilized lubricant base material
WO1997033954A1 (fr) * 1996-03-12 1997-09-18 Voitelukeskus Tonttila Oy Huile hydraulique et son procede de fabrication
WO1997039086A1 (fr) * 1996-04-16 1997-10-23 Unichema Chemie B.V. Fluides hydrauliques
EP0902006A2 (fr) * 1997-08-25 1999-03-17 Henkel Kommanditgesellschaft auf Aktien Oléines stables à l'oxydation
EP0997519A1 (fr) * 1998-09-29 2000-05-03 Nippon Mitsubishi Oil Corporation Huile pour machine réfrigérante

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2228425A1 (fr) * 2009-02-27 2010-09-15 Dako Ag Lubrifiant

Also Published As

Publication number Publication date
EP1373443A2 (fr) 2004-01-02
US20040147411A1 (en) 2004-07-29
DE10115829A1 (de) 2002-10-10
CA2442236A1 (fr) 2002-10-24
WO2002083607A3 (fr) 2003-01-09

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