WO1995002658A1 - Hydrauliköle enthaltend biologisch abbaubare guerbetalkohole - Google Patents

Hydrauliköle enthaltend biologisch abbaubare guerbetalkohole Download PDF

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Publication number
WO1995002658A1
WO1995002658A1 PCT/EP1994/002213 EP9402213W WO9502658A1 WO 1995002658 A1 WO1995002658 A1 WO 1995002658A1 EP 9402213 W EP9402213 W EP 9402213W WO 9502658 A1 WO9502658 A1 WO 9502658A1
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Prior art keywords
hydraulic oil
additives
iodine number
carbon atoms
base oil
Prior art date
Application number
PCT/EP1994/002213
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English (en)
French (fr)
Inventor
Gerhard Müller
Frank Bongardt
Matthias Fies
Peter Daute
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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Publication date
Application filed by Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Priority to US08/583,110 priority Critical patent/US5578558A/en
Priority to EP94922264A priority patent/EP0708810A1/de
Publication of WO1995002658A1 publication Critical patent/WO1995002658A1/de

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    • 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
    • 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
    • C10M2223/042—Metal salts thereof
    • 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
    • C10M2223/045—Metal containing thio derivatives
    • 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
    • C10N2010/04—Groups 2 or 12

Definitions

  • the present invention relates to hydraulic oils containing, in addition to conventional additives, at least one biodegradable Guerbeta1koho1 as base oil.
  • DE-A-39 27 155 describes an environmentally friendly base oil based on natural substances for the formulation of hydraulic oils containing a beet and / or soybean oil as the main oil component, specially selected antioxidants and a proportion of esters of trimethylolethane, trimethylolpropane and the same as the main oil component / or the neopentyl alcohol with Cs-Ci Q -moriocarboxylic acids or at least or partially unsaturated fatty acids based on rapeseed oil, soybean oil or sunflower oil
  • base oils according to DE-A-39 27 155 meet the usual requirements with regard to environmental friendliness, increased viscosity with increased operating temperature and low-temperature stability, they are nevertheless sensitive to hydrolysis due to the ester bond contained in the synthetic ester.
  • a hydraulic oil containing, in addition to conventional additives, at least one Guerbet alcohol of the general formula R-OH, in which R is a simple base oil is a branched radical containing 24 to 44 carbon atoms and having an iodine number of 20-150.
  • the hydraulic oil compositions according to the invention differ from the known hydraulic oils based on mineral oil, which are widely used in practice, in the selection of the environmentally friendly, biodegradable Guerbet alcohols as the basic component of the hydraulic oil.
  • Branched fatty alcohols of the Guerbet alcohol type which are used as a basic component in hydraulic oil compositions for the purposes of the present invention, are known substances which can be obtained by the relevant methods of preparative organic chemistry.
  • a classic process for their preparation is the condensation "Guerbetisation” of primary, linear, saturated or unsaturated alcohols in the presence of basic catalysts, which runs via the intermediate stages of the aldehydes and aldols (Soap Cosm. Chem. Spec. 52, 1987, ( as well as Ullmann's Encyclopedia of Technical Chemistry, oa0., volume 7, page 239 and volume 11, page 437).
  • the Guerbet alcohols used according to the invention contain 24 to 44 carbon atoms, preferably 32 to 40 carbon atoms. in the For the purposes of the invention, they can be used individually or as a mixture of various Guerbet alcohols as the base oil component.
  • the iodine number of the Guerbet alcohol or the Guerbet alcohol mixture is 20-150 and preferably 70-100.
  • the base oil component are the Guerbet alcohols of the unsaturated fatty alcohols, which are commercially available under the trade name HD-Ocenol (commercial products from Henkel KGaA, Düsseldorf).
  • An example of this is the Guerbet alcohol from HD-Ocenol 80/85, which is an oleyl-cetyl alcohol with an iodine number of 84-89 and 70-83% cig content.
  • HD-Ocenol 50/55 III (Ciss content 58-68%, iodine number 48-55), HD-Ocenol 60/65 (Ci ⁇ content 55- 75%, iodine number 60-65), HD-Ocenol 70/75 (Cig content 68-80%, iodine number 70- 75), the oleyl alcohol HD-Ocenol 90/95 (Ciß content 87-95%, iodine number 90-97), HD-Ocenol 92/96 (Ci ⁇ content 87- 93%, iodine number 95-105) and the oleyl-linoeyl alcohol HD-ocenol 110/130 (cis content 90-95%, iodine number 110-130).
  • the formulation of the finished hydraulic oil from the Guerbet alcohol or Guerbet alcohol mixture requires the addition of other, conventional components in a known manner.
  • antioxidants, corrosion inhibitors, high-pressure additives (EP additives), wear protection additives or pour point depressants can be added to the base oils described according to the invention.
  • the high-pressure additives are, in particular, sulfurized triglycerides, sulfurized fatty acid alkyl esters, sulfurized Sperm oils, phosphoric acid esters such as trioleyl alcohol phosphate or triaryl phosphate.
  • Zinc dialkyldithiophosphate compounds such as zinc (di-2-ethylhexyldithiophosphate) are particularly suitable as wear protection additives.
  • Pourpoint depressants include, for example, the products marketed under the trade names "Edenor” 2410 (commercial product from Henkel KGaA, Düsseldorf) and Viskoplex types (commercial products from Röhm, Darmstadt). These products are polymer-based pourpoint depressants that delay crystallization indefinitely.
  • Suitable corrosion protection inhibitors are, in particular, succinic haibesters, sorbitan monooleate, amine soaps from long-chain fatty acids.
  • succinic haibesters commercial product from Rheinchemie, Mannheim
  • Edenor or Eumulgin commercial product from Henkel KGaA, Düsseldorf.
  • antioxidants are combinations of sterically hindered aromatics, in particular TBHQ (tertiary-butyl-hydroxy-quinoline) or BHT (butoxylated hydroxytoluene) and anionic antioxidants such as, in particular, BHA (butoxylated hydroxyanisole) or phenothiazine (commercial product from Hoechst AG, Frankfurt).
  • TBHQ tertiary-butyl-hydroxy-quinoline
  • BHT butoxylated hydroxytoluene
  • anionic antioxidants such as, in particular, BHA (butoxylated hydroxyanisole) or phenothiazine (commercial product from Hoechst AG, Frankfurt).
  • a liquid antioxidant - Edenor VP 2465 commercial product from Henkel KGaA, Düsseldorf
  • the hydraulic oil compositions according to the invention contain at least 90% by weight, preferably at least 95% by weight and particularly preferably at least 98% by weight of the Guerbet alcohol or Guerbet alcohol mixture as the base oil component.
  • the Guerbet alcohols forming the base oil component of the hydraulic oils according to the invention have a favorable low-temperature behavior (low pour point), they are not sensitive to hydrolysis, they are biodegradable and, when added, they have an approximately constant viscosity even under oxidative conditions at elevated temperature.
  • the hydraulic oils are produced by intensively mixing the base oil component with the usual additives. Suitable procedures for this are known to the person skilled in the art, so that there is no need to go into this in detail.
  • the present invention is illustrated by the following example, but without being restricted thereto.
  • Air separation capacity (DIN 51 381) 10 min demulsibility (DIN 51 599) 20-30 min biodegradability (CEC-L33 T82-
  • the cold behavior can be determined by adding e.g. Improve Guerbitol 16 (2-hexyldecan-l-ol, commercial product from Henkel KGaA, Düsseldorf), at the same time the iodine number is reduced and the viscosity is set to ISO VG 46 or 32.

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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)

Abstract

Die vorliegende Erfindung betrifft ein Hydrauliköl enthaltend, neben üblichen Zusatzstoffen, als Grundöl wenigstens einen Guerbetalkohol der allgemeinen Formel R-OH, in dem R ein einfach verzweigter, 24 bis 44 Kohlenstoffatome enthaltender Rest ist und der eine Iodzahl von 20 bis 150 aufweist.

Description

Hvdraulikδle enthaltend biologisch abbaubare Guerbetalkohole
Die vorliegende Erfindung betrifft Hydrauliköle enthaltend, neben üblichen Zusatzstoffen, als Grundöl wenigstens einen biologisch abbaubaren Guerbeta1koho1.
Die DE-A-39 27 155 beschreibt ein umweltfreundliches Grundöl auf Naturstoffbasis für die Formulierung von Hydraulikölen enthaltend ein Rüb- und/oder Sojaöl als Ölhauptkomponente, speziell ausge¬ wählten Antioxidantien und einen zur ölhauptkomponentenmenge gleichen Anteil von Estern des Trimethylolethans, Trimethylol- propans und/oder des Neopentylalkohols mit Cs-CiQ-Moriocarbonsäuren oder zumindest oder teilweise ungesättigten Fettsäuren auf Rüböl-, Sojaöl- oder Sonnenblumenδlbasis
Obwohl die Grundöle nach der DE-A-39 27 155 hinsichtlich der Um¬ weltfreundlichkeit, Viskositätserhöhung bei erhöhter Betriebstempe¬ ratur und Kältestabilität die üblichen Anforderungen erfüllen, sind sie doch aufgrund der Esterbindung, die in dem synthetischen Ester enthalten ist, hydrolyseempfindlich.
Es war somit die Aufgabe der vorliegenden Erfindung, für die Formu¬ lierung von Hydraulikölen ein Grundöl zur Verfügung zu stellen, welches biologisch abbaubar ist, das bei erhöhter Betriebstempe¬ ratur keine nennenswerte Viskositätserhöhung unter oxidativen Be¬ dingungen aufweist, sowie einen niedrigen "Pourpoint" besitzt.
Die Aufgabe wurde erfindungsgemäß gelöst durch ein Hydrauliköl ent¬ haltend, neben üblichen Zusatzstoffen, als Grundöl wenigstens einen Guerbetalkohol der allgemeinen Formel R-OH, in dem R ein einfach verzweigter, 24 bis 44 Kohlenstoffatome enthaltender Rest ist und der eine Iodzahl von 20-150 aufweist.
Zu den näheren Einzelheiten über die Zusammensetzung der Hydraulik¬ öle sei zunächst auf den einschlägigen Stand der Technik verwiesen. Genannt sei hier insbesondere "Ull anns Encyclopädie der Tech¬ nischen Chemie", 4. Auflage (Verlage Chemie, Weinheim) Band 13, Seite 85 ff "Hydraulikflüssigkeit", sowie Dieter Klamann in "Schmierstoffe und verwandte Produkte" Herstellung, Eigenschaften, Anwendung (Verlag Chemie, Weinheim) 1982, Seite 147-148, 11.9 "Hydrauliköle".
Von den vorbekannten und in der Praxis in weitem Umfang einge¬ setzten Hydraulikölen auf Mineralölbasis unterscheiden sich die erfindungsgemäßen HydraulikölZusammensetzungen durch die Auswahl der umweltfreundlichen, biologisch abbaubaren Guerbetalkoholen als Grundkomponente des Hydrauliköls.
Verzweigte Fettalkohole vom Typ der Guerbetalkohole, die im Sinne der vorliegenden Erfindung als Grundkomponente in HydraulikölZu¬ sammensetzungen verwendet werden, stellen bekannte Stoffe dar, die nach den einschlägigen Methoden der präparativen organischen Chemie erhalten werden können. Ein klassisches Verfahren zu ihrer Her¬ stellung ist die Kondensation "Guerbetisierung" von primären, linearen, gesättigten oder ungesättigten Alkoholen in Gegenwart basischer Katalysatoren, die über die Zwischenstufen der Aldehyde und Aldole verläuft (Soap Cosm. Chem. Spec. 52, 1987, (sowie Ullmanns Encyclopädie der Technischen Chemie, o.a.0., Band 7, Seite 239 und Band 11, Seite 437).
Die erfindungsgemäß eingesetzten Guerbetalkohole enthalten 24 bis 44 Kohlenstoffatome, vorzugsweise 32 bis 40 Kohlenstoffatome. Im Sinne der Erfindung können sie einzeln oder als Gemisch verschie¬ dener Guerbetalkohole als Grundölkomponente eingesetzt werden. Die Iodzahl des Guerbetalkohols bzw. des Guerbetalkoholgemisches be¬ trägt 20-150 und vorzugsweise 70-100.
Besonders bevorzugt als Grundölkomponente sind die Guerbetalkohole der ungesättigten Fettalkohole, die unter dem Handelsnamen HD- Ocenol (Handelsprodukte der Firma Henkel KGaA, Düsseldorf) im Handel erhältlich sind. Als Beispiel sei hierzu der Guerbetalkohol von HD-Ocenol 80/85 angeführt, bei welchem es sich um einen Oleyl-Cetylalkohol mit einer Iodzahl von 84-89 und 70-83% Cig-Anteil handelt.
Ebenso geeignet sind Guerbetalkohole der Oleyl-Cetylalkohole HD- Ocenol 45/50 (Cχ8-Anteil 60-70%, Iodzahl 45-50), HD-Ocenol 50/55 (Cι8-Anteil 55-75%, Iodzahl 50-55), HD-Ocenol 50/55 III (Ciß-Anteil 58-68%, Iodzahl 48-55), HD-Ocenol 60/65 (Ciβ-Anteil 55- 75%, Iodzahl 60-65), HD-Ocenol 70/75 (Cig-Anteil 68-80%, Iodzahl 70- 75), der Oleylalkohol HD-Ocenol 90/95 (Ciß-Anteil 87-95%, Iodzahl 90-97), HD-Ocenol 92/96 (Ciβ-Anteil 87-93%, Iodzahl 95-105) und der Oleyl-Linoeyl-Alkohol HD-Ocenol 110/130 (Cis-Anteil 90-95%, Iodzahl 110-130).
Zur Formulierung des fertigen Hydrauliköls aus dem Guerbetalkohol oder Guerbetalkoholgemisches bedarf es in bekannter Weise des Zu¬ satzes weiterer, üblicher Komponenten. So können den erfindungs¬ gemäß beschriebenen Grundölen insbesondere Antioxidantien, Korrosionsinhibitoren, Hochdruckadditive (EP-Additive), Ver¬ schleißschutzadditive oder Pourpoint-Depressants zugesetzt werden.
Bei den Hochdruckadditiven handelt es sich insbesondere um geschwe¬ felte Triglyceride, geschwefelte Fettsäurealkylester, geschwefelte Spermöle, Phosphorsäureester wie Trioleylalkoholphosphat oder Triarylphosphat.
Als Verschleißschutzadditive sind insbesondere Zinkdialkyldi- thiophosphatverbindungen wie Zink(di-2-ethylhexyldithiophosphat) geeignet.
Als Pourpoint-Depressant sind beispielsweise die unter den Handelsnamen "Edenor" 2410 (Handelsprodukt der Firma Henkel KGaA, Düsseldorf) und Viskoplex-Typen (Handelsprodukte der Firma Röhm, Darmstadt) vertriebene Produkte zu erwähnen. Bei diesen Produkten handelt es sich um Pourpoint-Depressants auf Polymerbasis, die die Kristallisation unendlich verzögern.
Als Korrosionsschutzinhibitoren sind insbesondere Bernsteinsäure- haibester, Sorbitanmonooleat, Aminseifen von langkettigen Fett¬ säuren geeignet. Erwähnt seien in diesem Zusammenhang Additin (Handelsprodukt der Firma Rheinchemie, Mannheim), Edenor oder Eumulgin (Handelsprodukt der Firma Henkel KGaA, Düsseldorf).
Als Antioxidantien eignen sich insbesondere Kombinationen aus sterisch gehinderten Aromaten, insbesondere TBHQ (tertiärbutyl- hydroxy-Chinolin) oder BHT (butoxyliertes Hydroxytoluol) und anionische Antioxidantien wie insbesondere BHA (butoxyliertes Hydroxyanisol) oder Phenothiazin (Handelsprodukt der Firma Hoechst AG, Frankfurt). Weiterhin kann ein flüssiges Antioxidants - Edenor VP 2465 (Handelsprodukt der Firma Henkel KGaA, Düsseldorf) - verwendet werden, das aus einer Kombination von anionischem und phenolischem Antioxidants Sesteht.
Im übrigen wird zu der speziellen Formulierung von Hydraulikölen, ihren Zusatzstoffen und den Mengen dieser Zusatzstoffe auf den eingehend referierten druckschriftlichen Stand der Technik zu dieser Materialklasse verwiesen.
Die erfindungsgemäßen HydraulikölZusammensetzungen enthalten wenigstens 90 Gew.-%, vorzugsweise wenigstens 95 Gew.-% und besonders bevorzugt wenigstens 98 Gew.-% des Guerbetalkohols oder Guerbetalkoholgemisches als Grundölkomponente.
Die die Grundölkomponente der erfindungsgemäßen Hydrauliköle bildenden Guerbetalkohole besitzen ein günstiges Kälteverhalten (niedriger Pourpoint), sie sind nicht hydrolyseempfindlich, biologisch abbaubar und weisen additiviert eine annähernd gleich¬ bleibende Viskosität auch unter oxidativen Bedingungen bei erhöhter Temperatur auf.
Die Herstellung der Hydrauliköle erfolgt durch intensives Ver¬ mischen der Grundölkomponente mit den üblichen Zusatzstoffen. Geeignete Verfahrensweisen hierzu sind dem Fachmann bekannt, so daß sich ein näheres Eingehen hierauf erübrigt.
Die vorliegende Erfindung wird durch nachfolgendes Beispiel er¬ läutert, ohne jedoch darauf beschränkt zu sein.
Beispiel:
Guerbetalkohol aus HD-Ocenol 80/85 (Oleyl-Cetyl-Alkohol, 70-83% Cig-Anteil, Iodzahl = 84-89)
Bezeichnung: Guerbetocenol
Iodzahl (DGF C-V 11 b) 94
Säurezahl (DIN 53402) 1,0 Hydroxylzahl (DIN 53240) 100
Wasser n.K. Fischer (DIN 51 757) 0,08%
Dichte bei 20°C (DIN 51 757) 0,8589 g/cm3
Cloudpoint (DIN ISO 3015) -5°C
Pourpoint (DIN ISO 3016 -13°C
Kinemat.Viskositat n. Ubbelohde (DIN 51 562) 54,4 m2/s
Farbe n. Lovibond (DGF C-IV 4 b)
51/4" 31y / 3,5r
1" 3,6y / 0,7r
Luftabscheidever¬ mögen (DIN 51 381) 10 min Demulgiervermögen (DIN 51 599) 20-30 min biologische Abbau- barkeit (CEC-L33 T82-
Test) > 80%
Baader-Oxidationstest (DIN 54566)
(7 Tage, 95°C) jeweils Doppelbindung des Viskositätsanstiegs nach DIN 51 562, bei 40°C:
Guerbetalkohol (ohne Zusätze)
0 Tage 7 Tage Farbe
54,4 mm /s 82,27 mm2/s grün (durch Kupfer) 54,4 mm2/s 82,56 mm2/s
Guerbetalkohol + 1% BHT (Antioxidants. butyliertes Hvdroxytoluol)
0 Tage 7 Tage Farbe (n. Lovibond 1")
54,4 mm2/s 60,80 mm2/s 62 y 5,7r 54,4 mm /s 61,09 mm /s 62 y 5,3 r
Guerbetalkohol + 1% Edenor VP 2465
0 Tage 7 Tage Farbe (n. Lovibond 1")
54,4 mm2/s 75,80 mm2/s 52 y 6,8 r
54,4 mm2/s 79,00 mm2/s 59 y 7,3 r
Das Kälteverhalten (Pourpoint) laßt sich durch Zugabe von z.B. Guerbitol 16 (2-Hexyldecan-l-ol, Handelsprodukt der Firma Henkel KGaA, Düsseldorf) verbessern, gleichzeitig wird die Iodzahl ver¬ ringert und die Viskosität in den Bereich ISO VG 46 oder 32 einge¬ stellt.

Claims

Patentansprüche
1. Hydrauliköl enthaltend, neben üblichen Zusatzstoffen, als Grundöl wenigstens einen Guerbetalkohol der allgemeinen Formel R- 0H, in dem R ein einfach verzweigter, 24 bis 44 Kohlenstoffatome enthaltender Rest ist und der eine Iodzahl von 20 bis 150 aufweist.
2. Hydrauliköl nach Anspruch 1, dadurch gekennzeichnet, daß R 32 bis 40 Kohlenstoffatome enthält.
3. Hydrauliköl nach Anspruch 1 oder 2, dadurch gekennzeichnet, daß die Iodzahl 70 bis 100 beträgt.
4. Hydrauliköl nach einem oder mehreren der Ansprüche 1 bis 3, dadurch gekennzeichnet, daß das Hydrauliköl wenigstens 90 Gew.-% des Grundöls enthält.
5. Hydrauliköl nach einem oder mehreren der Ansprüche 1 bis 4, dadurch gekennzeichnet, daß es als übliche Zusatzstoffe Antioxi¬ dantien, Korrosionsinhibitoren, Hochdruckadditive, Verschlei߬ schutzadditive und/oder Pourpoint-Depressants enthält.
6. Verfahren zur Herstellung eines Hydrauliköls wie durch einen oder mehreren der Patentansprüche 1 bis 5 definiert, durch homo¬ genes Vermischen des wenigstens einen Guerbetalkohol der allge¬ meinen Formel R-OH, in dem R einen verzweigten, 24 bis 44 Kohlen¬ stoffatome enthaltender Rest ist und der eine Iodzahl von 20 bis 150 aufweist, mit üblichen Zusatzstoffen.
7. Verwendung wenigstens eines Guerbetalkohols der allgemeinen Formel R-OH, in dem R ein verzweigter, 24 bis 44 Kohlenstoffatome enthaltender Rest ist und der eine Iodzahl von 20 bis 150 aufweist als Grundöl in Hydrauliköl-Zusammensetzungen.
8. Verwendung nach Anspruch 7, dadurch gekennzeichnet, daß R 32 bis 40 Kohlenstoffatome enthält.
9. Verwendung nach Anspruch 7 oder 8, dadurch gekennzeichnet, daß die Iodzahl 70 bis 100 beträgt.
10. Verwendung nach einem oder mehreren der Ansprüche 7 bis 9, da¬ durch gekennzeichnet, daß das Hydrauliköl wenigstens 90 Gew.-% des Grundöls enthält.
11. Verwendung nach einem oder mehreren der Ansprüche 7 bis 10, dadurch gekennzeichnet, daß das Hydrauliköl neben dem Grundöl noch übliche Zusatzstoffe enthält.
12. Verwendung nach Anspruch 11, dadurch gekennzeichnet, daß die üblichen Zusatzstoffe Antioxidantien, Korrosionsinhibitoren, Ver¬ schleißschutzadditive, Hochdruckadditive oder Pourpoint-Depressants sind.
PCT/EP1994/002213 1993-07-15 1994-07-06 Hydrauliköle enthaltend biologisch abbaubare guerbetalkohole WO1995002658A1 (de)

Priority Applications (2)

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EP94922264A EP0708810A1 (de) 1993-07-15 1994-07-06 Hydrauliköle enthaltend biologisch abbaubare guerbetalkohole

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DE102007027371A1 (de) * 2007-06-11 2008-12-18 Cognis Oleochemicals Gmbh Verfahren zur Herstellung einer Verbindung aufweisend mindestens eine Ester-Gruppe
CN107460025A (zh) * 2017-08-31 2017-12-12 东莞安默琳机械制造技术有限公司 一种加工钛合金的微量润滑切削油及其制备方法
CN114450379A (zh) * 2019-05-30 2022-05-06 弗洛伊泰克国际有限责任公司 溶解力增强剂组合物、其制备方法及其使用方法

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Publication number Publication date
EP0708810A1 (de) 1996-05-01
US5578558A (en) 1996-11-26
DE4323829A1 (de) 1995-01-19

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