WO2012059492A1 - Use of alkanolamines based on propylene oxide as additives in lubricants - Google Patents

Use of alkanolamines based on propylene oxide as additives in lubricants Download PDF

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Publication number
WO2012059492A1
WO2012059492A1 PCT/EP2011/069197 EP2011069197W WO2012059492A1 WO 2012059492 A1 WO2012059492 A1 WO 2012059492A1 EP 2011069197 W EP2011069197 W EP 2011069197W WO 2012059492 A1 WO2012059492 A1 WO 2012059492A1
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Prior art keywords
alkanolamines
lubricants
formula
lubricant
additives
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PCT/EP2011/069197
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German (de)
French (fr)
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Norbert Gutfrucht
Frank Hettche
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Basf Se
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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/06Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M133/08Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M173/00Lubricating compositions containing more than 10% water
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/02Water
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/16Antiseptic; (micro) biocidal or bactericidal
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/24Emulsion properties
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/02Bearings
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/04Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/135Steam engines or turbines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/20Metal working
    • C10N2040/242Hot working
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/38Conveyors or chain belts
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00Form in which the lubricant is applied to the material being lubricated
    • C10N2050/01Emulsions, colloids, or micelles

Definitions

  • alkanolamines based on propylene oxide as additives in lubricants
  • the invention relates to lubricants, which are characterized in that they are an alkanolamine of the formula I.
  • alkanolamines which are selected from alkanolamines of the formulas I to IV, where R 1, R 2, R 3, R 1 ', R 2' and R 3 'are each independently an H atom or a C 1 to C 4 alkyl group, and R 4 is a C1 to C16 alkyl group.
  • Lubricants in particular so-called cooling lubricants (also called cooling lubricants), are used in manufacturing technology to reduce friction and simultaneous heat dissipation. In machine tools, lubricants are used to produce as many high quality workpieces as possible.
  • Lubricants in particular cooling lubricants, contain natural or synthetic or modified mineral oils as an essential component.
  • aqueous lubricants are used. These are, for example, aqueous solutions of polar synthetic or correspondingly polar modified natural mineral oils or also aqueous emulsions in which the mineral oil is emulsified with the aid of a surface-active compound. With aqueous lubricants, it can come to an attack with organic germs, such as fungi or bacteria. To counteract this, biocides are added.
  • WO 2005/055720 discloses that special alkylethanolamines can additionally inhibit bacterial growth.
  • DE-A 10 2008 043 580 describes alkanolamines, which can be used as additives to lubricants, have a biocide-supporting action, regulate the pH and improve the emulsification of the mineral oil in aqueous lubricants.
  • Object of the present invention were therefore lubricants which have good performance properties and to contain as few and simple additives must.
  • the additives should be as easy to prepare as possible and possibly toxicologically as safe as possible.
  • the lubricants according to the invention contain an alkanolamine of the formula I above
  • alkanolamines which are selected from alkanolamines of the formulas I to IV.
  • R4 is a C1 to C8 alkyl group, in particular a C1 to C4 alkyl group, and particularly preferably a methyl group or ethyl group.
  • R1 is identical to R1 ', R2 to R2' and R3 to R3 '. This is in particular due to the method of preparation described below.
  • R1 and R1 ' are an H atom.
  • R 1 and R 1 ' are an H atom and at least one of R 2 or R 3 and at least one of R 2' or R 3 'is an H atom.
  • R 1, R 2, R 3, R 1 ', R 2' and R 3 ' are each an H atom.
  • it is an alkanolamine of the formula I or II, very particularly preferably an alkanolamine of the formula I.
  • alkanolamines which are selected from alkanolamines of the formulas I to IV.
  • Such a mixture may e.g. contain different alkanolamines of the formula I or consist exclusively of different alkanolamines of the formula I. The same applies to alkanolamines of the formulas II to IV.
  • the mixture contains alkanolamines of different formulas I to IV;
  • mixtures are suitable which contain alkanolamines of the formula I.
  • the mixture also contains, in particular, an alkanolamine of the formula II and, if appropriate, alkanolamines of the formula III and IV.
  • alkanolamine of the formula I is alkanolamines of the formula Ia:
  • alkanolamines of the formula II are alkanolamines of the formula IIa:
  • R4 has the above meaning.
  • a mixture comprising alkanolamines of the formula Ia and alkanolamines of the formula IIa is very particularly preferred as a mixture of alkanolamines.
  • R 4 is identical in formulas Ia and IIa.
  • mixtures which contain from 50 to 99% by weight, in particular from 80 to 99% by weight, of an alkanolamine of the formula I, in particular of the formula Ia, and correspondingly to 1 to 50% by weight, in particular to 1 to 20 wt .-% of an alkanolamine of the formula II, in particular of the formula IIa, and to 0 to 10 wt.% Of alkanolamines of the formulas III and IV, wherein the percentages by weight based on the total by weight of the alkanolamines of the formulas I to IV are.
  • the preparation of the above alkanolamines can be carried out by conventional methods.
  • the alkanolamines can be prepared in particular by a two-stage addition of primary amines of the formula H 2 N-R 4 to propylene oxide or propylene oxide derivatives.
  • the primary amine can add to the R 2 , R 3 substituted C atom of Propyleno xids or propylene oxide derivative according to the following schematic representation:
  • the primary amine can add to the CH3 substituted C atom to give the following structural isomeric addition product.
  • the product of the 1. Step is therefore generally a mixture of these two addition products.
  • the secondary amine obtained adds again to a propylene oxide or propylene oxide derivative; in the schematic diagram below, this is shown only by the example of one of the two addition products obtained in the 1st stage:
  • Step can also be obtained as a mixture of alkanolamines of the formulas I to IV.
  • the resulting mixture can be used according to the invention as described above. However, it is also possible to separate a single desired alkanolamine from the mixture and to use it appropriately in lubricants.
  • the lubricants preferably contain the alkanolamine or mixture of alkanolamines in an amount of from 0.05 to 30% by weight, more preferably from 0.1 to 20% by weight and most preferably from 0.5 to 10% by weight. based on the total amount of the lubricant.
  • the alkanolamines can be added to the lubricant at any time prior to or during use in any manner.
  • the alkanolamines can directly Lubricant, which already contains all other ingredients added; but they can also be mixed in advance with other ingredients of the lubricant and then combined in this form with the remaining components of the lubricant.
  • aqueous lubricants see below
  • first so-called lubricant concentrates are prepared that are compositions that already contain the components of the lubricant except for the water, the latter is then added before use the lubricant concentrates in the amount that for the particular use desired distribution of the lubricant in the device in which the lubricant is used results.
  • the total amount of the alkanolamines used in the invention is preferably at least 2 wt .-%, most preferably at least 5 wt .-%, based on the lubricant concentrate;
  • the maximum amount is preferably 30% by weight, in particular 20% by weight, likewise based on the lubricant concentrate.
  • the lubricants preferably contain a natural or synthetic lubricating component as an essential ingredient.
  • Natural lubricating components are e.g. Mineral oils, i. Oils obtained by distillation from lignite, coal, peat, wood or, in particular, petroleum. They contain in particular saturated hydrocarbons.
  • Synthetic lubricating components are e.g. Oils made from suitable raw materials or by chemical modification of natural mineral oils (e.g., so-called ester oils).
  • the lubricants are generally liquid under the conditions of use (pressure, temperature). Preferably, they are liquid at 21 ° C, 1 bar.
  • aqueous lubricants are preferred.
  • the aqueous lubricants may be aqueous solutions of correspondingly polar mineral oils, for example synthetic, polymeric alcohols.
  • the aqueous lubricants may also be emulsions of natural or synthetic mineral oils in water.
  • Aqueous lubricants may be marketed in the form of the solution or emulsion; However, it is also possible that the solution or dispersion is prepared from the starting materials only shortly before the subsequent use.
  • the lubricants according to the invention are preferably aqueous
  • Lubricants in particular aqueous solutions of mineral oils and particularly preferably aqueous emulsions of mineral oils.
  • the lubricants according to the invention may contain further additives.
  • This may mean that in addition to the alkanolamine or alkanolamine mixtures according to the invention of the formula I nis IV or mixtures thereof, other amines are part of the corresponding lubricants or lubricant concentrates and the latter in their effectiveness by an alkanolamine of the formula I to IV or a mixture of these Alkanolamines are amplified.
  • the mineral oil may be self-emulsifying, i. it is chemically modified so that an emulsion forms in water without further additives.
  • the emulsions contain a surface-active compound which causes or contributes to the emulsification of the mineral oil. Suitable for this purpose are customary emulsifiers and / or protective colloids.
  • the lubricants according to the invention are in particular cooling lubricants;
  • the latter not only provide good lubrication but also provide good heat removal, e.g. during the processing or production of workpieces in machine tools.
  • the lubricants or cooling lubricants according to the invention can be used in any areas of production technology. They are suitable for machine tools of all kinds. They have special significance, for example. in the industrial production of parts of tools or machines and in particular of driving and aircraft components.
  • the use of the lubricant according to the invention in the production of light metal components for example. Of magnesium and aluminum is particularly preferred.
  • lubricants or coolants according to the invention Another area of application for the lubricants or coolants according to the invention is given when used in promotion measures of all kinds (mining, oil extraction of all kinds).
  • promotion measures of all kinds for example, by adding the lubricant according to the invention, the functionality and life of the boring machine is extended.
  • the lubricants or cooling lubricants according to the invention can be used in transmissions or turbines, for example also vehicle transmissions or transmissions of wind turbines.
  • the alkanolamines additionally contribute to the emulsification of the mineral oil, so that optionally even further surface-active compounds are dispensed with.
  • alkanolamines of formulas I to IV and their mixtures, respectively promoted the action of the biocide component, and thereby enhanced efficacy against bacteria, e.g. the mycobacterium, or fungi.

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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)
  • Lubricants (AREA)

Abstract

Lubricants characterized in that they comprise an alkanolamine of the formula (I), of the formula (II), of the formula (III), of the formula (IV), or a mixture of alkanolamines selected from alkanolamines of the formulae (I) to (IV), where R1, R2, R3, R1', R2' and R3' independently of one another are an H atom or a C1 to C4 alkyl group and R4 is a C1 to C16 alkyl group.

Description

Verwendung von Alkanolaminen auf Basis von Propylenoxid als Zusatzstoffe in Schmiermitteln  Use of alkanolamines based on propylene oxide as additives in lubricants
Beschreibung description
Die vorliegende Anmeldung schließt durch Verweis die am 4. November 2010 eingereichte läufige US-Anmeldung 61/410000 ein. The present application includes by reference the provisional US application 61/410000 filed on Nov. 4, 2010.
Die Erfindung betrifft Schmiermittel, welche dadurch gekennzeichnet sind, dass sie ein Alkano- lamin der Formel I The invention relates to lubricants, which are characterized in that they are an alkanolamine of the formula I.
Figure imgf000003_0001
der Formel II
Figure imgf000003_0001
of formula II
Figure imgf000003_0002
der Formel III
Figure imgf000003_0003
der Formel IV
Figure imgf000003_0002
of formula III
Figure imgf000003_0003
of formula IV
Figure imgf000003_0004
oder ein Gemisch von Alkanolaminen, welche ausgewählt sind aus Alkanolaminen der Formeln I bis IV, enthalten, wobei R1 , R2, R3, R1 ', R2' und R3' unabhängig voneinander für ein H-Atom oder eine C1 bis C4-Alkylgruppe stehen und R4 für eine C1 bis C16 Alkylgruppe steht.
Figure imgf000003_0004
or a mixture of alkanolamines which are selected from alkanolamines of the formulas I to IV, where R 1, R 2, R 3, R 1 ', R 2' and R 3 'are each independently an H atom or a C 1 to C 4 alkyl group, and R 4 is a C1 to C16 alkyl group.
Schmiermittel, insbesondere auch sogenannte Kühlschmiermittel (auch Kühlschmierstoffe genannt), werden in der Fertigungstechnik zur Verminderung der Reibung und gleichzeitigen Wärmeabfuhr eingesetzt. In Werkzeugmaschinen werden Schmiermittel verwendet, um möglichst viele Werkstücke mit hoher Qualität produzieren zu können. Lubricants, in particular so-called cooling lubricants (also called cooling lubricants), are used in manufacturing technology to reduce friction and simultaneous heat dissipation. In machine tools, lubricants are used to produce as many high quality workpieces as possible.
Schmiermittel, insbesondere Kühlschmiermittel, enthalten als wesentlichen Bestandteil natürliche oder synthetische, bzw. modifizierte Mineralöle. Häufig werden wässrige Schmiermittel verwendet. Dabei handelt es sich z.B. um wässrige Lösungen von polaren synthetischen oder entsprechend polar modifizierten natürlichen Mineralölen oder auch um wässrige Emulsionen, in denen das Mineralöl mit Hilfe eine oberflächenakti- ven Verbindung emulgiert ist. Bei wässrigen Schmierstoffen kann es zu einem Befall mit organischen Keimen, wie Pilzen oder Bakterien kommen. Um dem entgegenzuwirken, werden Biozide zugesetzt. Aus WO 2005/055720 ist bekannt, dass spezielle Alkylethanolamine das Bakterienwachstum zusätzlich hemmen können. DE-A 10 2008 043 580 beschreibt Alkanolamine, welche als Zusatzstoffe zu Schmiermitteln verwendet werden können, eine Biozid unterstützende Wirkung haben, den pH-Wert regulieren und die Emulgierung des Mineralöls in wässrigen Schmiermitteln verbessern. Lubricants, in particular cooling lubricants, contain natural or synthetic or modified mineral oils as an essential component. Often, aqueous lubricants are used. These are, for example, aqueous solutions of polar synthetic or correspondingly polar modified natural mineral oils or also aqueous emulsions in which the mineral oil is emulsified with the aid of a surface-active compound. With aqueous lubricants, it can come to an attack with organic germs, such as fungi or bacteria. To counteract this, biocides are added. WO 2005/055720 discloses that special alkylethanolamines can additionally inhibit bacterial growth. DE-A 10 2008 043 580 describes alkanolamines, which can be used as additives to lubricants, have a biocide-supporting action, regulate the pH and improve the emulsification of the mineral oil in aqueous lubricants.
Erwünscht sind alternative Zusatzstoffe für Schmiermittel, mit denen die vorstehenden Wirkun- gen in möglichst großem Ausmaß bei möglichst geringer Zusatzmenge erfüllen. What is desired are alternative additives for lubricants with which the above effects are fulfilled to the greatest possible extent with the least possible additional amount.
Aufgabe der vorliegenden Erfindung waren daher Schmiermittel welche gute anwendungstechnische Eigenschaften haben und dazu möglichst wenige und einfache Zusatzstoffe enthalten müssen. Darüberhinaus sollten die Zusatzstoffe möglichst einfach herstellbar und gegebenen- falls toxikologisch möglichst unbedenklich sein. Object of the present invention were therefore lubricants which have good performance properties and to contain as few and simple additives must. In addition, the additives should be as easy to prepare as possible and possibly toxicologically as safe as possible.
Demgemäß wurden die eingangs definierten Schmiermittel gefunden. Accordingly, the initially defined lubricants were found.
Die erfindungsgemäßen Schmiermittel enthalten ein Alkanolamin der obigen Formel I The lubricants according to the invention contain an alkanolamine of the formula I above
Figure imgf000004_0001
der Formel II
Figure imgf000004_0001
of formula II
Figure imgf000004_0002
der Formel III
Figure imgf000004_0003
der Formel IV
Figure imgf000004_0002
of formula III
Figure imgf000004_0003
of formula IV
Figure imgf000005_0001
oder ein Gemisch von Alkanolaminen, welche ausgewählt sind aus Alkanolaminen der Formeln I bis IV.
Figure imgf000005_0001
or a mixture of alkanolamines which are selected from alkanolamines of the formulas I to IV.
Vorzugsweise steht R4 für eine C1 bis C8 Alkylgruppe insbesondere eine C1 bis C4 Alkylgrup- pe und besonders bevorzugt für eine Methylgruppe oder Ethylgruppe. Preferably, R4 is a C1 to C8 alkyl group, in particular a C1 to C4 alkyl group, and particularly preferably a methyl group or ethyl group.
In einer bevorzugten Ausführungsform sind R1 mit R1 ', R2 mit R2' und R3 mit R3' identisch. Dies ergibt sich insbesondere durch das unten beschriebene Verfahren zur Herstellung. Insbesondere stehen R1 und R1 ' für ein H-Atom. In a preferred embodiment, R1 is identical to R1 ', R2 to R2' and R3 to R3 '. This is in particular due to the method of preparation described below. In particular, R1 and R1 'are an H atom.
In einer bevorzugten Ausführungsform stehen R1 und R1 ' für ein H-Atom und mindestens einer der Reste R2 oder R3 und mindestens einer der Reste R2' oder R3' für ein H-Atom. In einer besonders bevorzugten Ausführungsform stehen R1 , R2, R3, R1 ', R2' und R3' jeweils für ein H-Atom. In a preferred embodiment, R 1 and R 1 'are an H atom and at least one of R 2 or R 3 and at least one of R 2' or R 3 'is an H atom. In a particularly preferred embodiment, R 1, R 2, R 3, R 1 ', R 2' and R 3 'are each an H atom.
In einer bevorzugten Ausführungsform handelt es sich um ein Alkanolamin der Formel I oder II, ganz besonders bevorzugt handelt es sich um ein Alkanolamin der Formel I. In a preferred embodiment, it is an alkanolamine of the formula I or II, very particularly preferably an alkanolamine of the formula I.
In einer weiteren Ausführungsform handelt es sich um ein Gemisch von Alkanolaminen, welche ausgewählt sind aus Alkanolaminen der Formeln I bis IV. In a further embodiment, it is a mixture of alkanolamines which are selected from alkanolamines of the formulas I to IV.
Ein derartiges Gemisch kann z.B. unterschiedliche Alkanolaminen der Formel I enthalten oder ausschließlich aus unterschiedlichen Alkanolaminen der Formel I bestehen. Entsprechendes gilt für Alkanolamine der Formeln II bis IV. Such a mixture may e.g. contain different alkanolamines of the formula I or consist exclusively of different alkanolamines of the formula I. The same applies to alkanolamines of the formulas II to IV.
Vorzugsweise enthält das Gemisch Alkanolamine unterschiedlicher Formeln I bis IV; insbesondere sind Gemische geeignet, welche Alkanolamine der Formeln I enthalten. Preferably, the mixture contains alkanolamines of different formulas I to IV; In particular, mixtures are suitable which contain alkanolamines of the formula I.
Neben einem Alkanolamin der Formel I enthält das Gemisch insbesondere noch ein Alkanolamin der Formel II und gegebenenfalls auch Alkanolamine der Formel III und IV. In addition to an alkanolamine of the formula I, the mixture also contains, in particular, an alkanolamine of the formula II and, if appropriate, alkanolamines of the formula III and IV.
Besonders bevorzugt ist ein Gemisch, welches zu mehr als 60 Gew.-%, insbesondere zu mehr als 80 Gew.-% aus einem Alkanolamin der Formel I besteht. Bevorzugte Alkanonolamine der Formel I sind Alkanolamine der Formel la: Particular preference is given to a mixture which consists of more than 60% by weight, in particular more than 80% by weight, of an alkanolamine of the formula I. Preferred alkanonolamines of the formula I are alkanolamines of the formula Ia:
Figure imgf000006_0001
Figure imgf000006_0001
Bevorzugte Alkanolamine der Formel II sind Alkanolamine der Formel IIa: Preferred alkanolamines of the formula II are alkanolamines of the formula IIa:
Figure imgf000006_0002
Figure imgf000006_0002
In den Formel la und IIa hat R4 die obige Bedeutung. In formulas Ia and IIa, R4 has the above meaning.
Als Gemisch von Alkanolaminen ist entsprechend ein Gemisch, welches Alkanolamine der Formel la und Alkanolamine der Formel IIa enthält, ganz besonderes bevorzugt. Insbesondere ist R4 in Formel la und IIa identisch. Accordingly, a mixture comprising alkanolamines of the formula Ia and alkanolamines of the formula IIa is very particularly preferred as a mixture of alkanolamines. In particular, R 4 is identical in formulas Ia and IIa.
In Betracht kommen insbesondere Gemische, welche zu 50 bis 99 Gew.-%, insbesondere zu 80 bis 99 Gew.-% aus einem Alkanolamin der Formel I, insbesondere der Formel la, und entsprechend zu 1 bis 50 Gew.%, insbesondere zu 1 bis 20 Gew.-% aus einem Alkanolamin der Formel II, insbesondere der Formel IIa, und zu 0 bis 10 Gew.% aus Alkanolaminen der Formeln III und IV bestehen, wobei die prozentualen Gewichtsangaben auf die Gewichtssumme der Alkanolamine der Formeln I bis IV bezogen sind. Particularly suitable are mixtures which contain from 50 to 99% by weight, in particular from 80 to 99% by weight, of an alkanolamine of the formula I, in particular of the formula Ia, and correspondingly to 1 to 50% by weight, in particular to 1 to 20 wt .-% of an alkanolamine of the formula II, in particular of the formula IIa, and to 0 to 10 wt.% Of alkanolamines of the formulas III and IV, wherein the percentages by weight based on the total by weight of the alkanolamines of the formulas I to IV are.
Die Herstellung der vorstehenden Alkanolamine kann nach üblichen Verfahren erfolgen. Die Alkanolamine lassen sich insbesondere durch eine zweistufige Anlagerung von primären Ami nen der Formel H2N-R4 an Propylenoxid bzw. Propylenoxidderivate herstellen. The preparation of the above alkanolamines can be carried out by conventional methods. The alkanolamines can be prepared in particular by a two-stage addition of primary amines of the formula H 2 N-R 4 to propylene oxide or propylene oxide derivatives.
In der 1 . Stufe kann sich das primäre Amin an das R2, R3 substituierte C-Atom des Propyleno xids bzw. Propylenoxidderivats gemäß nachstehender schematischer Darstellung addieren: In the 1. Step, the primary amine can add to the R 2 , R 3 substituted C atom of Propyleno xids or propylene oxide derivative according to the following schematic representation:
Figure imgf000006_0003
Das primäre Amin kann sich alternativ auch an das CH3- substituierte C-Atom addieren, so dass sich das nachstehende struktur-isomere Additionsprodukt ergibt.
Figure imgf000006_0003
Alternatively, the primary amine can add to the CH3 substituted C atom to give the following structural isomeric addition product.
Figure imgf000007_0001
Figure imgf000007_0001
Das Produkt der 1 . Stufe ist daher im Allgemeinen ein Gemisch dieser beiden Additionsprodukte. The product of the 1. Step is therefore generally a mixture of these two addition products.
In der zweiten Stufe addiert sich das erhaltene sekundäre Amin erneut an ein Propylenoxid bzw. Propylenoxidderivat; in der nachstehenden schematischen Darstellung ist dies nur am Beispiel eines der beiden in der 1. Stufe erhaltenen Additionsprodukte gezeigt: In the second stage, the secondary amine obtained adds again to a propylene oxide or propylene oxide derivative; in the schematic diagram below, this is shown only by the example of one of the two addition products obtained in the 1st stage:
Figure imgf000007_0002
Figure imgf000007_0002
Figure imgf000007_0003
Figure imgf000007_0003
Hierbei kann wiederum ein Gemisch von zwei Additionsprodukten entstehen, je nachdem welches C-Atom der Epoxidgruppe sich das sekundäre Amin addiert hat. This can in turn give rise to a mixture of two addition products, depending on which C atom of the epoxide group has added to the secondary amine.
Ausgehend von beiden Additionsprodukten der 1 . Stufe kann so auch ein Gemisch von Alkanolaminen der Formeln I bis IV erhalten werden. Starting from both addition products of the 1. Step can also be obtained as a mixture of alkanolamines of the formulas I to IV.
Das erhaltene Gemisch kann, wie oben beschrieben, erfindungsgemäß verwendet werden. Es ist jedoch auch möglich, ein einzelnes gewünschtes Alkanolamin aus dem Gemisch abzutrennen und entsprechend in Schmiermitteln zu verwenden. The resulting mixture can be used according to the invention as described above. However, it is also possible to separate a single desired alkanolamine from the mixture and to use it appropriately in lubricants.
Die Schmiermittel enthalten das Alkanolamin oder Gemisch von Alkanolaminen vorzugsweise in einer Menge von 0,05 bis 30 Gew.-%, besonders bevorzugt von 0,1 bis 20 Gew.-% und ganz besonders bevorzugt von 0,5 bis 10 Gew.-% bezogen auf die Gesamtmenge des Schmiermittels. The lubricants preferably contain the alkanolamine or mixture of alkanolamines in an amount of from 0.05 to 30% by weight, more preferably from 0.1 to 20% by weight and most preferably from 0.5 to 10% by weight. based on the total amount of the lubricant.
Die Alkanolamine können dem Schmiermittel zu einem beliebigen Zeitpunkt vor oder während der Verwendung in beliebiger Weise zugesetzt werden. Die Alkanolamine können direkt dem Schmiermittel, welches bereits alle weiteren Bestandteile enthält, zugesetzt werden; sie können aber auch vorab mit anderen Bestandteilen des Schmiermittels gemischt und dann in dieser Form mit den restlichen Bestandteilen des Schmiermittels vereinigt werden. In einer Ausführungsform werden bei wässrigen Schmiermitteln (siehe unten) zunächst sogenannte Schmier- mittelkonzentrate hergestellt, dass sind Zusammensetzungen, die bereits die Bestandteile des Schmiermittels bis auf das Wasser enthalten, Letzteres wird dann vor der Anwendung den Schmiermittelkonzentraten in der Menge zugesetzt, dass die für die jeweilige Verwendung angestrebte Verteilung des Schmiermittels in der Vorrichtung, in der das Schmiermittel zur Anwendung kommt, resultiert. The alkanolamines can be added to the lubricant at any time prior to or during use in any manner. The alkanolamines can directly Lubricant, which already contains all other ingredients added; but they can also be mixed in advance with other ingredients of the lubricant and then combined in this form with the remaining components of the lubricant. In one embodiment, in aqueous lubricants (see below) first so-called lubricant concentrates are prepared that are compositions that already contain the components of the lubricant except for the water, the latter is then added before use the lubricant concentrates in the amount that for the particular use desired distribution of the lubricant in the device in which the lubricant is used results.
Bezogen auf das Schmiermittelkonzentrat im Falle wässriger Schmiermittel beträgt die Gesamtmenge der erfindungsgemäß verwendeten Alkanolamine vorzugsweise mindestens 2 Gew.-%, ganz besonders bevorzugt mindestens 5 Gew.-%, bezogen auf das Schmiermittelkonzentrat; bevorzugt beträgt die maximale Menge 30 Gew.-%, insbesondere 20 Gew.-% ebenfalls bezo- gen auf das Schmiermittelkonzentrat. Based on the lubricant concentrate in the case of aqueous lubricants, the total amount of the alkanolamines used in the invention is preferably at least 2 wt .-%, most preferably at least 5 wt .-%, based on the lubricant concentrate; The maximum amount is preferably 30% by weight, in particular 20% by weight, likewise based on the lubricant concentrate.
Die Schmiermittel enthalten als wesentlichen Bestandteil vorzugsweise eine natürliche oder synthetische Schmierkomponente. Natürliche Schmierkomponenten sind z.B. Mineralöle, d.h. Öle, welche durch Destillation aus Braunkohle, Steinkohle, Torf, Holz oder insbesondere Erdöl gewonnen werden. Sie enthalten insbesondere gesättigte Kohlenwasserstoffe. The lubricants preferably contain a natural or synthetic lubricating component as an essential ingredient. Natural lubricating components are e.g. Mineral oils, i. Oils obtained by distillation from lignite, coal, peat, wood or, in particular, petroleum. They contain in particular saturated hydrocarbons.
Synthetische Schmierkomponenten sind z.B. Öle, welche aus geeigneten Ausgangsstoffen oder durch chemische Modifizierung von natürlichen Mineralölen hergestellt werden (z.B. sogenannte Esteröle). Synthetic lubricating components are e.g. Oils made from suitable raw materials or by chemical modification of natural mineral oils (e.g., so-called ester oils).
Weitere Typen von Schmierkomponenten, welche in den erfindungsgemäßen Schmiermitteln eingesetzt werden können, sind den Fachleuten bekannt. Other types of lubricating components that can be used in the lubricants of the invention are known to those skilled in the art.
Die Schmiermittel sind im Allgemeinen unter den Anwendungsbedingungen (Druck, Temperatur) flüssig. Vorzugsweise sind sie bei 21 °C, 1 bar flüssig. The lubricants are generally liquid under the conditions of use (pressure, temperature). Preferably, they are liquid at 21 ° C, 1 bar.
Unterschieden wird zwischen nicht wässrigen und wässrigen Schmiermitteln. Im Rahmen dieser Erfindung sind wässrige Schmiermittel bevorzugt. A distinction is made between non-aqueous and aqueous lubricants. In the context of this invention, aqueous lubricants are preferred.
Bei den wässrigen Schmiermitteln kann es sich um wässrige Lösungen von entsprechend polaren Mineralölen, z.B. synthetischen, polymeren Alkoholen, handeln. Bei den wässrigen Schmiermitteln kann es sich auch um Emulsionen von natürlichen oder synthetischen Mineralölen in Wasser handeln. Wässrige Schmiermittel können in Form der Lösung oder Emulsion vermarktet werden; in Betracht kommt aber auch, dass die Lösung oder Dispersion erst kurz vor der späteren Verwendung aus den Ausgangstoffen hergestellt wird. Bei den erfindungsgemäßen Schmiermitteln handelt es sich vorzugsweise um wässrige The aqueous lubricants may be aqueous solutions of correspondingly polar mineral oils, for example synthetic, polymeric alcohols. The aqueous lubricants may also be emulsions of natural or synthetic mineral oils in water. Aqueous lubricants may be marketed in the form of the solution or emulsion; However, it is also possible that the solution or dispersion is prepared from the starting materials only shortly before the subsequent use. The lubricants according to the invention are preferably aqueous
Schmiermittel, insbesondere um wässrige Lösungen von Mineralölen und besonders bevorzugt um wässrige Emulsionen von Mineralölen.  Lubricants, in particular aqueous solutions of mineral oils and particularly preferably aqueous emulsions of mineral oils.
Die erfindungsgemäßen Schmiermittel können je nach Anforderung weitere Zusatzstoffe enthal- ten. In Betracht kommen z.B. Zusatzstoffe zur Regelung der Viskosität, Zusatzstoffe zur Verminderung der Korrosion, Zusatzstoffe zur Verringerung der Schaumbildung, Zusatzstoffe zur Verminderung der Reibung, Biozide oder auch sonstige Zusatzstoffe zur Verbesserung der anwendungstechnischen Eigenschaften, insbesondere der Schmierung und Wärmeabfuhr. Dies kann dazu führen, dass neben den erfindungsgemäßen Alkanolamin oder Alkanolaminmi- schungen der Formel I nis IV bzw. deren Mischungen noch andere Amine Bestandteil der entsprechenden Schmiermittel oder Schmiermittelkonzentrate sind und letztere in ihrer Wirksamkeit durch ein Alkanolamin der Formel I bis IV oder ein Gemisch dieser Alkanolamine verstärkt werden. Depending on the requirements, the lubricants according to the invention may contain further additives. Additives for controlling viscosity, additives for reducing corrosion, additives for reducing foaming, additives for reducing friction, biocides or other additives for improving the performance properties, in particular the lubrication and heat dissipation. This may mean that in addition to the alkanolamine or alkanolamine mixtures according to the invention of the formula I nis IV or mixtures thereof, other amines are part of the corresponding lubricants or lubricant concentrates and the latter in their effectiveness by an alkanolamine of the formula I to IV or a mixture of these Alkanolamines are amplified.
In den wässrigen Emulsionen kann das Mineralöl selbstemulgierend sein, d.h. es ist chemisch so modifiziert, dass sich eine Emulsion in Wasser ohne weitere Zusatzstoffe ausbildet. Vorzugsweise enthalten die Emulsionen jedoch eine oberflächenaktive Verbindung, welche die Emulgierung des Mineralöls bewirkt oder dazu beiträgt. In Betracht kommen dazu übliche E- mulgatoren und /oder Schutzkolloide. In the aqueous emulsions, the mineral oil may be self-emulsifying, i. it is chemically modified so that an emulsion forms in water without further additives. Preferably, however, the emulsions contain a surface-active compound which causes or contributes to the emulsification of the mineral oil. Suitable for this purpose are customary emulsifiers and / or protective colloids.
Bei den erfindungsgemäßen Schmiermitteln handelt es sich insbesondere um Kühlschmiermittel; letztere bewirken nicht nur eine gute Schmierung sondern sorgen auch für eine gute Wärmeabfuhr, z.B. während der Verarbeitung bzw. Herstellung von Werkstücken in Werkzeugma- schinen. The lubricants according to the invention are in particular cooling lubricants; The latter not only provide good lubrication but also provide good heat removal, e.g. during the processing or production of workpieces in machine tools.
Die erfindungsgemäßen Schmiermittel bzw. Kühlschmiermittel können in beliebigen Bereichen der Fertigungstechnik eingesetzt werden. Sie eignen sich für Werkzeugmaschinen aller Art. Eine besondere Bedeutung haben sie z.B. bei der industriellen Herstellung von Teilen von Werkzeugen oder Maschinen und im Besonderen von Fahr- und Flugzeugbauteilen. Hierbei ist der Einsatz der erfindungsgemäßen Schmiermittel bei der Herstellung von Leichtmetallbauteilen, bspw. aus Magnesium und Aluminium besonders bevorzugt. The lubricants or cooling lubricants according to the invention can be used in any areas of production technology. They are suitable for machine tools of all kinds. They have special significance, for example. in the industrial production of parts of tools or machines and in particular of driving and aircraft components. Here, the use of the lubricant according to the invention in the production of light metal components, for example. Of magnesium and aluminum is particularly preferred.
Ein weiterer Anwendungsbereich für die erfindungsgemäßen Schmiermittel bzw. Kühlschmier- mittel ist beim Einsatz in Fördermaßnahmen aller Art gegeben (Bergbau, Ölförderung aller Art). Hier wird beispielsweise durch Zusatz der erfindungsgemäßen Schmiermittel die Funktionsfähigkeit und Lebensdauer des Bohrwerks verlängert. Darüber hinaus können die erfindungsgemäßen Schmiermittel bzw. Kühlschmiermittel in Getrieben oder Turbinen, z.B. auch Fahrzeuggetrieben oder Getrieben von Windrädern zum Einsatz kommen. Another area of application for the lubricants or coolants according to the invention is given when used in promotion measures of all kinds (mining, oil extraction of all kinds). Here, for example, by adding the lubricant according to the invention, the functionality and life of the boring machine is extended. In addition, the lubricants or cooling lubricants according to the invention can be used in transmissions or turbines, for example also vehicle transmissions or transmissions of wind turbines.
Alkanolamine der Formel I bis IV, bzw. deren Gemische regulieren den pH-Wert und bewirken einen Korrosionsschutz. Alkanolamines of the formula I to IV, or mixtures thereof, regulate the pH and bring about corrosion protection.
Es ist ein Vorteil der erfindungsgemäßen Schmiermittel, dass die Alkanolamine darüber hinaus zur Emulgierung des Mineralöls beitragen, so dass gegebenenfalls sogar auf weitere oberflä- chenaktive Verbindungen verzichtet werden.  It is an advantage of the lubricants according to the invention that the alkanolamines additionally contribute to the emulsification of the mineral oil, so that optionally even further surface-active compounds are dispensed with.
Darüber hinaus unterstützten die Alkanolamine der Formeln I bis IV bzw. deren Gemische die Wirkung der Biozidkomponente, und dadurch die Wirksamkeit gegenüber Bakterien, wie z.B. dem Mycobakterium, oder gegenüber Pilzen.  In addition, the alkanolamines of formulas I to IV and their mixtures, respectively, promoted the action of the biocide component, and thereby enhanced efficacy against bacteria, e.g. the mycobacterium, or fungi.

Claims

Patentansprüche claims
1 . Schmiermittel, dadurch gekennzeichnet, dass sie ein Alkanolamin der Formel I 1 . Lubricant, characterized in that it is an alkanolamine of the formula I.
Figure imgf000011_0001
der Formel II
Figure imgf000011_0001
of formula II
Figure imgf000011_0002
der Formel III
Figure imgf000011_0002
of formula III
Figure imgf000011_0003
der Formel IV
Figure imgf000011_0003
of formula IV
Figure imgf000011_0004
oder ein Gemisch von Alkanolaminen, welche ausgewählt sind aus Alkanolaminen der Formeln I bis IV, enthalten, wobei R1 , R2, R3, R1 ', R2' und R3' unabhängig voneinander für ein H-Atom oder eine C1 bis C4-Alkylgruppe stehen und R4 für eine C1 bis C16 Alkylgruppe steht.
Figure imgf000011_0004
or a mixture of alkanolamines which are selected from alkanolamines of the formulas I to IV, where R 1, R 2, R 3, R 1 ', R 2' and R 3 'are each independently an H atom or a C 1 to C 4 alkyl group, and R 4 is a C1 to C16 alkyl group.
Schmiermittel gemäß Anspruch 1 , dadurch gekennzeichnet, dass R4 für eine C1 bis C4 Alkylgruppe steht. Lubricant according to claim 1, characterized in that R4 is a C1 to C4 alkyl group.
Schmiermittel gemäß Anspruch 1 oder 2, dadurch gekennzeichnet, dass R1 mit R1', R2 mit R2' und R3 mit R3' identisch sind. Lubricant according to claim 1 or 2, characterized in that R 1 with R 1 ' , R 2 with R 2' and R 3 with R 3 'are identical.
Schmiermittel gemäß einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, dass R1 , R2, R3, R1 ', R2' und R3' jeweils für ein H-Atom stehen. Lubricant according to one of claims 1 to 3, characterized in that R1, R2, R3, R1 ', R2' and R3 'are each an H atom.
5. Schmiermittel gemäß einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, dass es sich um ein Gemisch von Alkanolaminen handelt, welches Alkanolamine der Formel I und II enthält. 5. Lubricant according to one of claims 1 to 4, characterized in that it is a mixture of alkanolamines containing alkanolamines of the formula I and II.
6. Schmiermittel gemäß einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, dass es sich um ein Gemisch von Alkanolaminen handelt, welches zu mindestens 80 Gew.% aus einem Alkanolamin der Formel I besteht. 6. A lubricant according to any one of claims 1 to 5, characterized in that it is a mixture of alkanolamines, which consists of at least 80 wt.% Of an alkanolamine of the formula I.
7. Schmiermittel gemäß einem der Ansprüche 1 bis 6, dadurch gekennzeichnet, dass sie das Alkanolamin oder das Gemisch der Alkanolamine in Mengen von 0,05 bis 30 Gew. % enthalten. 7. A lubricant according to any one of claims 1 to 6, characterized in that they contain the alkanolamine or the mixture of alkanolamines in amounts of 0.05 to 30 wt.%.
8. Schmiermittel gemäß einem der Ansprüche 1 bis 7, dadurch gekennzeichnet, dass es sich um wässrige Schmiermittel handelt. 8. Lubricant according to one of claims 1 to 7, characterized in that they are aqueous lubricants.
9. Schmiermittel gemäß einem der Ansprüche 1 bis 8, dadurch gekennzeichnet, dass es sich um wässrige Lösungen oder Emulsionen handelt. 9. Lubricant according to one of claims 1 to 8, characterized in that it is aqueous solutions or emulsions.
10. Schmiermittel gemäß einem der Ansprüche 1 bis 9, dadurch gekennzeichnet, dass es sich um wässrige Lösungen oder Emulsionen von synthetischen oder nicht synthetischen10. A lubricant according to any one of claims 1 to 9, characterized in that it is aqueous solutions or emulsions of synthetic or non-synthetic
Mineralölen handelt. Mineral oils are traded.
1 1. Schmiermittel gemäß einem der Ansprüche 1 bis 10, dadurch gekennzeichnet, dass sie weitere Zusatzstoffe ausgewählt aus Zusatzstoffen zur Einstellung der Viskosität, Zusatz- Stoffen zur Verminderung der Korrosion, Zusatzstoffen zur Verringerung der Schaumbildung, Zusatzstoffen zur Verminderung der Reibung, Bioziden und gegebenenfalls sonstigen Zusatzstoffen zur Verbesserung der anwendungstechnischen Eigenschaften enthalten. 1 1. A lubricant according to any one of claims 1 to 10, characterized in that it further additives selected from additives for adjusting the viscosity, additives to reduce corrosion, additives to reduce foaming, additives to reduce friction, biocides and optionally contain other additives to improve the performance properties.
12. Schmiermittel gemäß einem der Ansprüche 1 bis 1 1 , dadurch gekennzeichnet, dass es sich um Kühlschmiermittel handelt. 12. Lubricant according to one of claims 1 to 1 1, characterized in that it is cooling lubricant.
13. Verwendung von Schmiermitteln gemäß einem der Ansprüche 1 bis 11 als Schmiermittel bei der Fertigen von Bauteilen oder in Fördertätigkeiten. 13. Use of lubricants according to one of claims 1 to 11 as a lubricant in the manufacture of components or in conveying activities.
14. Verwendung von Schmiermitteln gemäß einem der Ansprüche 1 bis 11 in Getrieben oder Turbinen. 14. Use of lubricants according to one of claims 1 to 11 in transmissions or turbines.
PCT/EP2011/069197 2010-11-04 2011-11-02 Use of alkanolamines based on propylene oxide as additives in lubricants WO2012059492A1 (en)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1906038A1 (en) * 1969-02-07 1970-08-13 Huels Chemische Werke Ag Ep and anti-corrosion additives for - lubricants
US4781849A (en) * 1987-05-21 1988-11-01 Aluminum Company Of America Lyotropic liquid crystal metalworking lubricant composition
JPH0198696A (en) * 1987-10-12 1989-04-17 Toho Chem Ind Co Ltd Water-soluble cutting oil
US5549838A (en) * 1994-03-25 1996-08-27 Nippon Oil Co., Ltd. Hydraulic working oil composition for buffers
WO2005055720A1 (en) 2003-11-19 2005-06-23 Arkema Inc. Alkyl ethanolamines for the control of mycobacteria in functional fluid
DE102008043580A1 (en) 2008-11-07 2010-05-12 Basf Se Lubricant, useful e.g. as cooling lubricants and for manufacturing of components e.g. tools and machineries, preferably vehicle- and aircraft components, and light metal components, comprises an alkanolamine

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1906038A1 (en) * 1969-02-07 1970-08-13 Huels Chemische Werke Ag Ep and anti-corrosion additives for - lubricants
US4781849A (en) * 1987-05-21 1988-11-01 Aluminum Company Of America Lyotropic liquid crystal metalworking lubricant composition
JPH0198696A (en) * 1987-10-12 1989-04-17 Toho Chem Ind Co Ltd Water-soluble cutting oil
US5549838A (en) * 1994-03-25 1996-08-27 Nippon Oil Co., Ltd. Hydraulic working oil composition for buffers
WO2005055720A1 (en) 2003-11-19 2005-06-23 Arkema Inc. Alkyl ethanolamines for the control of mycobacteria in functional fluid
DE102008043580A1 (en) 2008-11-07 2010-05-12 Basf Se Lubricant, useful e.g. as cooling lubricants and for manufacturing of components e.g. tools and machineries, preferably vehicle- and aircraft components, and light metal components, comprises an alkanolamine

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