EP0726335A1 - Lactobionamide containing corrosion inhibiting composition - Google Patents

Lactobionamide containing corrosion inhibiting composition Download PDF

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Publication number
EP0726335A1
EP0726335A1 EP96101716A EP96101716A EP0726335A1 EP 0726335 A1 EP0726335 A1 EP 0726335A1 EP 96101716 A EP96101716 A EP 96101716A EP 96101716 A EP96101716 A EP 96101716A EP 0726335 A1 EP0726335 A1 EP 0726335A1
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Prior art keywords
lactobionic acid
corrosion
alkylamides
agents
corrosion protection
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German (de)
French (fr)
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EP0726335B1 (en
Inventor
Klaus-Günther Gerling
Helge Rau
Kornelia Wendler
Petra Schwarz
Karlheinz Uhlig
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Solvay GmbH
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Solvay Deutschland GmbH
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    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
    • C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
    • C23F11/14—Nitrogen-containing compounds
    • C23F11/145—Amides; N-substituted amides
    • 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
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/16—Amides; Imides
    • 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
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium containing a sulfur-to-oxygen bond
    • C10M135/10—Sulfonic acids or derivatives 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
    • C10M173/00—Lubricating compositions containing more than 10% water
    • 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
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/02—Water
    • 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
    • C10M2215/08—Amides
    • 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
    • C10M2215/08—Amides
    • C10M2215/082—Amides containing hydroxyl groups; Alkoxylated derivatives
    • 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
    • C10M2215/086—Imides
    • 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
    • C10M2215/12—Partial amides of polycarboxylic acids
    • 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
    • C10M2215/12—Partial amides of polycarboxylic acids
    • C10M2215/122—Phtalamic acid
    • 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
    • C10M2215/28—Amides; Imides
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
    • 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
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
    • 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
    • C10N2040/20—Metal working
    • 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
    • C10N2040/20—Metal working
    • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/01—Emulsions, colloids, or micelles

Definitions

  • the invention relates to corrosion protection agents which contain lactobionic acid N-alkylamides.
  • anti-corrosion agents In many metalworking processes such as Cutting, grinding or drilling use anti-corrosion agents to protect the machined metal objects from rust.
  • Many of the previously used corrosion protection agents contain sulfur-containing compounds such as Petroleum sulfonates or alkylarylsulfonic acids or nitrogen-containing compounds such as e.g. secondary amines or alkanolamines.
  • Sulfur-containing corrosion protection agents have the disadvantage that their active ingredients are easily modified or broken down by sulfur-reducing microorganisms.
  • amine-containing anticorrosive agents which contain, in particular, secondary amines, there is the possibility that nitrosamines which are hazardous to health and which have previously formed through uncontrolled chemical reactions are released.
  • new amine-free corrosion protection agents are particularly desirable which, as a corrosion-inhibiting agent, contain an active ingredient based on renewable raw materials which is also favorable from an environmental point of view.
  • the present invention is therefore based on the object of providing new corrosion protection agents.
  • lactobionic acid N-alkylamides have a corrosion-inhibiting effect.
  • the invention thus relates to anticorrosive agents which contain lactobionic acid N-alkylamides.
  • the anti-corrosion agents according to the invention preferably contain lactobionic acid N-alkylamides, the saturated or partially unsaturated alkyl radicals of which are bonded via the amide function and have a chain length of Have 8 to 18 carbon atoms.
  • those corrosion protection agents are preferred which contain lactobionic acid-N-alkylamides which have been obtained by the reaction of lactobionic acid or reactive lactobionic acid derivatives, preferably lactobionic acid lactone, with a primary fatty amine mixture.
  • primary fatty amines are primary amines which contain an aliphatic radical corresponding to the aliphatic radical of a fatty acid.
  • Fatty amines can e.g. can be obtained technically from fatty acids by first converting them to their nitriles, which are then reduced to amines.
  • Fatty amine mixtures which are obtained from naturally occurring fatty acid mixtures are preferably used. The proportion of unsaturated fatty amines in these fatty amine mixtures fluctuates between approximately 5 and 85% by weight.
  • the corrosion protection agents according to the invention particularly preferably comprise lactobionic acid-N-alkylamides from the group lactobionic acid-N-oleylamide, lactobionic acid-N-coconut amide and lactobionic acid-N-tallow amide.
  • lactobionic acid N-alkylamides can easily be prepared by reacting lactobionic acid or lactobionic acid derivative with the corresponding fatty amine mixtures.
  • So oleylamine is a fatty amine mixture that is derived from a fatty acid mixture derived from sunflower oil and / or soybean oil.
  • a corresponding fatty amine mixture derived from coconut fat is referred to as coconut fatty amine and a corresponding fatty amine mixture derived from tallow is described as tallow amine.
  • coconut fatty amine A corresponding fatty amine mixture derived from coconut fat
  • tallow amine a corresponding fatty amine mixture derived from tallow is described as tallow amine.
  • unsaturated fatty amines there is always a certain proportion of unsaturated fatty amines in these natural fatty amine mixtures available.
  • Oleylamine obtained from sunflower oil contains, for example, approximately 14% by weight of saturated fatty amines with 12 to 18 carbon atoms and approximately 85% by weight of unsaturated fatty amines with 14 to 18 carbon atoms.
  • Oleylamine (also called soya amine) obtained from soybean oil contains, for example, approximately 16% by weight of saturated C 16 fatty amines, approximately 15% by weight of saturated C 18 fatty amines and a proportion of approximately 63% by weight unsaturated fatty amines with 14 to 18 carbon atoms.
  • coconut fatty amine contains, for example, approx. 50% by weight of saturated C 12 fatty amines, approx. 18% by weight of saturated C 14 fatty amines approx. 7% by weight of unsaturated C 18 fatty amines.
  • Tallow amine contains, for example, approximately 29% by weight of saturated C 16 fatty amines, approximately 23% by weight of saturated C 18 fatty amines and a proportion of approximately 42% by weight of unsaturated fatty amines with 14 to 18 carbon atoms.
  • the corrosion protection agent according to the invention preferably contains the lactobionic acid N-alkylamides in the form of an aqueous solution.
  • the aqueous solutions of lactobionic acid-N-alkylamides can be used alone or as a mixture with other compounds as corrosion inhibitors.
  • the content of lactobionic acid-N-alkyl-amides, based on the aqueous solution, can be in the concentration range customary for anti-corrosion agents, advantageously in the concentration range from 0.1 to 20% by weight, e.g. are in the concentration range from 1 to 10% by weight.
  • the pH of the aqueous anti-corrosion agents should be below pH 9.0.
  • the corrosion inhibitors according to the invention which contain lactobionic acid N-alkylamides in an aqueous solution, can be completely clear solutions or, in particular in the presence of other compounds, finely divided emulsions which can be transparent, opal or even milky.
  • the anticorrosive agents according to the invention can contain all compounds customary for anticorrosive agents, e.g. Contains petroleum sulfonates, mineral oils or other additives.
  • the anti-corrosion agents according to the invention show emulsifying and corrosion-inhibiting effects in aqueous metalworking agents containing mineral oils.
  • Another object of the invention is therefore the use of the anti-corrosion agents according to the invention in metalworking agents, in particular water-containing metalworking agents.
  • Metalworking agents are understood to mean all liquids customary for metalworking, in particular cooling lubricants, drilling, cutting and grinding oils, rust removal, paint stripping and passivation agents.
  • With the anticorrosive agents according to the invention it is possible to produce metalworking emulsions which contain a large amount of water without rusting.
  • the corrosion protection agents according to the invention are notable for excellent skin tolerance and high biodegradability.
  • the corrosion-inhibiting effect of the corrosion protection agents according to the invention was determined by means of the swarf / filter paper method according to DIN 51360, part 2.
  • lactobionic acid N-oleylamide As described by way of example for lactobionic acid N-oleylamide, the other lactobionic acid amides were also prepared.
  • Gray cast iron chips (material DIN 1691-GG30 of about 5 mm x 5 mm in size) were washed with petroleum ether, sieved through a wire sieve and dried at about 105 ° C. in a drying cabinet. After drying, it was avoided to touch the chips by hand.
  • a round filter made of filter paper (diameter 40 mm) was placed in a Petri dish and evenly sprinkled with 2 g ( ⁇ 0.1 g) of the dried chips. The chips were then uniformly wetted with 2 ml of the solution to be examined using a full pipette. The lid of the Petri dish was put on and the Petri dish was left to stand for 2 hours at room temperature. Then the chips were removed from the round filter, the round filter rinsed under running water, swirled in acetone for about 5 seconds and dried at room temperature. Immediately after cleaning and drying the round filter, the degree of corrosion of the corrosion marks on the round filter was determined by visual inspection. The degree of corrosion determined for the anticorrosive agents according to the invention is given in the table below.

Abstract

A corrosion inhibitor (I) contains lactobionic acid N-alkylamides (II).

Description

Die Erfindung betrifft Korrosionsschutzmittel, welche Lactobionsaure-N-alkylamide enthalten.The invention relates to corrosion protection agents which contain lactobionic acid N-alkylamides.

Bei vielen Vorgängen der Metallbearbeitung wie z.B. Schneiden, Schleifen oder Bohren werden Korrosionsschutzmittel eingesetzt, um die bearbeiteten Metallgegenstände vor Rostbildung zu schützen. Viele der bisher üblichen Korrosionsschutzmittel enthalten schwefelhaltige Verbindungen wie z.B. Petrolsulfonate oder Alkylarylsulfonsäuren oder stickstoffhaltige Verbindungen wie z.B. sekundäre Amine oder Alkanolamine. Schwefelhaltige Korrosionsschutzmittel haben dabei den Nachteil, daß deren Wirkstoffe leicht von schwefelreduzierenden Mikroorganismen modifiziert bzw. abgebaut werden. Bei aminhaltigen Korrosionsschutzmitteln, welche insbesondere sekundäre Amine enthalten, besteht die Möglichkeit, daß aus ihren gesundheitsgefährdende Nitrosamine freigesetzt werden, welche sich zuvor durch unkontrollierte chemische Reaktionen gebildet haben. Es besteht somit immer noch der Bedarf nach neuen Korrosionsschutzmitteln, welche diese Nachteile des Standes der Technik nicht aufweisen. Hierbei sind insbesondere neue aminfreie Korrosionsschutzmittel wünschenswert, die als korrosionsinhibierendes Agens einen auch unter Umweltschutzgesichtspunkten günstigen Wirkstoff auf Basis nachwachsender Rohstoffe enthalten.In many metalworking processes such as Cutting, grinding or drilling use anti-corrosion agents to protect the machined metal objects from rust. Many of the previously used corrosion protection agents contain sulfur-containing compounds such as Petroleum sulfonates or alkylarylsulfonic acids or nitrogen-containing compounds such as e.g. secondary amines or alkanolamines. Sulfur-containing corrosion protection agents have the disadvantage that their active ingredients are easily modified or broken down by sulfur-reducing microorganisms. In the case of amine-containing anticorrosive agents which contain, in particular, secondary amines, there is the possibility that nitrosamines which are hazardous to health and which have previously formed through uncontrolled chemical reactions are released. There is therefore still a need for new anti-corrosion agents which do not have these disadvantages of the prior art. In this context, new amine-free corrosion protection agents are particularly desirable which, as a corrosion-inhibiting agent, contain an active ingredient based on renewable raw materials which is also favorable from an environmental point of view.

Der vorliegenden Erfindung liegt daher die Aufgabe zugrunde, neue Korrosionsschutzmittel zur Verfügung zu stellen.The present invention is therefore based on the object of providing new corrosion protection agents.

Überraschenderweise wurde nun gefunden, daß Lactobionsäure-N-alkylamide, eine korrosionsinhibierende Wirkung besitzen.Surprisingly, it has now been found that lactobionic acid N-alkylamides have a corrosion-inhibiting effect.

Gegenstand der Erfindung sind somit Korrosionsschutzmittel, die Lactobionsäure-N-alkylamide enthalten. Bevorzugt enthalten die erfindungsgemäßen Korrionsschutzmittel Lactobionsäure-N-alkylamide, deren über die Amidfunktion gebundene gesättigte oder teilweise ungesättigte Alkylreste eine Kettenlänge von
8 bis 18 Kohlenstoffatomen aufweisen.The invention thus relates to anticorrosive agents which contain lactobionic acid N-alkylamides. The anti-corrosion agents according to the invention preferably contain lactobionic acid N-alkylamides, the saturated or partially unsaturated alkyl radicals of which are bonded via the amide function and have a chain length of
Have 8 to 18 carbon atoms.

Insbesondere sind solche Korrosionsschutzmittel bevorzugt, welche Lactobionsäure-N-alkylamide enthalten, welche durch die Umsetzung von Lactobionsäure oder reaktiven Lactobionsäurederivaten, vorzugsweise Lactobionsäurelacton, mit einem primären Fettamingemisch erhalten wurden. Als "primäre Fettamine" werden im Rahmen der vorliegenden Erfindung primäre Amine bezeichnet, welche einen dem aliphatischen Rest einer Fettsäure entsprechenden aliphatischen Rest enthalten. Fettamine können z.B. technisch aus Fettsäuren erhalten werden, in dem diese zunächst in ihre Nitrile überführt werden, welche anschließend zu Aminen reduziert werden. Bevorzugt werden Fettamingemische eingesetzt, welche aus natürlich vorkommenden Fettsäuregemischen gewonnen werden. Der Anteil an ungesättigten Fettaminen schwankt dabei in diesen Fettamingemischen zwischen ca. 5 und 85 Gew.-%.In particular, those corrosion protection agents are preferred which contain lactobionic acid-N-alkylamides which have been obtained by the reaction of lactobionic acid or reactive lactobionic acid derivatives, preferably lactobionic acid lactone, with a primary fatty amine mixture. In the context of the present invention, “primary fatty amines” are primary amines which contain an aliphatic radical corresponding to the aliphatic radical of a fatty acid. Fatty amines can e.g. can be obtained technically from fatty acids by first converting them to their nitriles, which are then reduced to amines. Fatty amine mixtures which are obtained from naturally occurring fatty acid mixtures are preferably used. The proportion of unsaturated fatty amines in these fatty amine mixtures fluctuates between approximately 5 and 85% by weight.

Besonders bevorzugt enthalten die erfindungsgemäßen Korrosionsschutzmittel Lactobionsäure-N-alkylamide aus der Gruppe Lactobionsäure-N-Oleylamid, Lactobionsäure-N-Kokosamid und Lactobionsäure-N-Talgamid. Diese besonders bevorzugten Lactobionsäure-N-alkylamide können leicht durch die Umsetzung von Lactobionsäure bzw. Lactobionsäurederivat mit den entsprechenden Fettamingemischen hergestellt werden. So wird mit Oleylamin ein Fettamingemisch bezeichnet, welches aus einem aus Sonnenblumenöl und/oder Sojaöl stammenden Fettsäuregemisch gewonnen wurde. Mit Kokosfettamin wird ein entsprechendes sich aus Kokosfett herleitendes Fettamingemisch, mit Talgamin ein entsprechendes sich aus Talg herleitendes Fettamingemisch bezeichnet. Neben gesättigten Fettaminen ist in diesen natürlichen Fettamingemischen immer ein gewisser Anteil ungesättigter Fettamine vorhanden. Aus Sonnenblumenöl gewonnenes Oleylamin enthält z.B. ca. 14 Gew.-% an gesättigten Fettaminen mit 12 bis 18 Kohlenstoffatomen und ca. 85 Gew.-% an ungesättigten Fettaminen mit 14 bis 18 Kohlenstoffatomen. Aus Sojaöl gewonnenes Oleylamin (auch Sojaamin genannt) enthält z.B. ca. 16 Gew.-% an gesättigten C16-Fettaminen, ca. 15 Gew.-% an gesättigten C18-Fettaminen sowie einen Anteil von ca. 63 Gew.-% an ungesättigten Fettaminen mit 14 bis 18 Kohlenstoffatomen. Kokosfettamin enthält z.B. ca. 50 Gew.-% an gesättigten C12-Fettaminen, ca. 18 Gew.-% an gesättigten C14-Fettaminen ca. einen Anteil von ca. 7 Gew.-% an ungesättigten C18-Fettaminen. Talgamin enthält z.B. ca. 29 Gew.-% an gesättigten C16-Fettaminen, ca. 23 Gew.-% an gesättigten C18-Fettaminen sowie einen Anteil von ca. 42 Gew.-% an ungesättigten Fettaminen mit 14 bis 18 Kohlenstoffatomen.The corrosion protection agents according to the invention particularly preferably comprise lactobionic acid-N-alkylamides from the group lactobionic acid-N-oleylamide, lactobionic acid-N-coconut amide and lactobionic acid-N-tallow amide. These particularly preferred lactobionic acid N-alkylamides can easily be prepared by reacting lactobionic acid or lactobionic acid derivative with the corresponding fatty amine mixtures. So oleylamine is a fatty amine mixture that is derived from a fatty acid mixture derived from sunflower oil and / or soybean oil. A corresponding fatty amine mixture derived from coconut fat is referred to as coconut fatty amine and a corresponding fatty amine mixture derived from tallow is described as tallow amine. In addition to saturated fatty amines, there is always a certain proportion of unsaturated fatty amines in these natural fatty amine mixtures available. Oleylamine obtained from sunflower oil contains, for example, approximately 14% by weight of saturated fatty amines with 12 to 18 carbon atoms and approximately 85% by weight of unsaturated fatty amines with 14 to 18 carbon atoms. Oleylamine (also called soya amine) obtained from soybean oil contains, for example, approximately 16% by weight of saturated C 16 fatty amines, approximately 15% by weight of saturated C 18 fatty amines and a proportion of approximately 63% by weight unsaturated fatty amines with 14 to 18 carbon atoms. Coconut fatty amine contains, for example, approx. 50% by weight of saturated C 12 fatty amines, approx. 18% by weight of saturated C 14 fatty amines approx. 7% by weight of unsaturated C 18 fatty amines. Tallow amine contains, for example, approximately 29% by weight of saturated C 16 fatty amines, approximately 23% by weight of saturated C 18 fatty amines and a proportion of approximately 42% by weight of unsaturated fatty amines with 14 to 18 carbon atoms.

Lactobionsäure(=4-(β-D-Galacto)-D-Glukonsäure) und Lactobionsäurelacton sowie deren Herstellung sind bereits bekannt. Lactobionsäure kann beispielsweise auf bekannte Weise durch Oxidation von Lactose erhalten werden.Lactobionic acid (= 4- (β-D-galacto) -D-gluconic acid) and lactobionic acid lactone and their preparation are already known. Lactobionic acid can be obtained, for example, in a known manner by oxidation of lactose.

Vorzugsweise enthält das erfindungsgemäße Korrosionsschutzmittel die Lactobionsäure-N-alkylamide in Form einer wäßrigen Lösung. Die wäßrigen Lösungen der Lactobionsäure-N-alkylamide können dabei alleine oder auch im Gemisch mit weiteren Verbindungen als Korrosionsschutzmittel eingesetzt werden. Der Gehalt an Lactobionsäure-N-alkyl-amiden, bezogen auf die wäßrige Lösung, kann dabei im für Korrionsschutzmittel üblichen Konzentrationsbereich, zweckmäßigerweise im Konzentrationsbereich von 0,1 bis 20 Gew.-%, z.B. im Konzentrationsbereich von 1 bis 10 Gew.-%, liegen. Der pH-Wert der wäßrigen Korrosionsschutzmittel sollte unterhalb pH 9,0 liegen.The corrosion protection agent according to the invention preferably contains the lactobionic acid N-alkylamides in the form of an aqueous solution. The aqueous solutions of lactobionic acid-N-alkylamides can be used alone or as a mixture with other compounds as corrosion inhibitors. The content of lactobionic acid-N-alkyl-amides, based on the aqueous solution, can be in the concentration range customary for anti-corrosion agents, advantageously in the concentration range from 0.1 to 20% by weight, e.g. are in the concentration range from 1 to 10% by weight. The pH of the aqueous anti-corrosion agents should be below pH 9.0.

Die erfindungsgemäßen Korrosionsschutzmittel, die Lactobionsäure-N-alkylamide in einer wäßrigen Lösung enthalten, können vollständig klare Lösungen oder, insbesondere bei Gegenwart anderer Verbindungen, feinverteilte Emulsionen sein, die transparent, opal oder auch milchig trüb sein können.The corrosion inhibitors according to the invention, which contain lactobionic acid N-alkylamides in an aqueous solution, can be completely clear solutions or, in particular in the presence of other compounds, finely divided emulsions which can be transparent, opal or even milky.

Neben Lactobionsäure-N-alkylamiden können die erfindungsgemäßen Korrosionsschutzmittel alle für Korrosionsschutzmittel üblichen Verbindungen, z.B. Petrolsulfonate, Mineralöle oder andere Additive enthalten.In addition to lactobionic acid-N-alkylamides, the anticorrosive agents according to the invention can contain all compounds customary for anticorrosive agents, e.g. Contains petroleum sulfonates, mineral oils or other additives.

Die erfindungsgemäßen Korrosionsschutzmittel zeigen emulgierende und korrosionsinhibierende Wirkung in mineralölhaltigen, wäßrigen Metallbearbeitungsmitteln. Ein weiterer Gegenstand der Erfindung ist daher die Verwendung der erfindungsgemäßen Korrosionsschutzmitteln in Metallbearbeitungsmitteln, insbesondere wasserhaltigen Metallbearbeitungsmitteln. Unter Metallbearbeitungsmitteln werden dabei alle zur Metallbearbeitung üblichen Flüssigkeiten, insbesondere Kühlschmiermittel, Bohr-, Schneid- und Schleiföle, Entrostungs-, Entlackungs- und Passivierungsmittel verstanden. Mit den erfindungsgemäßen Korrosionsschutzmitteln ist es möglich, Metallbearbeitungsemulsionen herzustellen, welche in hohem Maße Wasser enthalten, ohne daß es dabei zur Rostbildung kommt. Neben einem guten Korrosionsschutz zeichnen sich die erfindungsgemäßen Korrosionsschutzmittel durch eine ausgezeichnete Hautverträglichkeit und hohe biologische Abbaubarkeit aus.The anti-corrosion agents according to the invention show emulsifying and corrosion-inhibiting effects in aqueous metalworking agents containing mineral oils. Another object of the invention is therefore the use of the anti-corrosion agents according to the invention in metalworking agents, in particular water-containing metalworking agents. Metalworking agents are understood to mean all liquids customary for metalworking, in particular cooling lubricants, drilling, cutting and grinding oils, rust removal, paint stripping and passivation agents. With the anticorrosive agents according to the invention it is possible to produce metalworking emulsions which contain a large amount of water without rusting. In addition to good corrosion protection, the corrosion protection agents according to the invention are notable for excellent skin tolerance and high biodegradability.

Die korrosionsinhibierende Wirkung der erfindungsgemäßen Korrosionsschutzmittel wurde mittels des Späne/Filterpapier-Verfahrens nach der DIN 51360, Teil 2, ermittelt.The corrosion-inhibiting effect of the corrosion protection agents according to the invention was determined by means of the swarf / filter paper method according to DIN 51360, part 2.

Die nachfolgenden Beispiele sollen die Erfindung weiter erläutern, ohne sie jedoch in ihrem Umfang zu begrenzen.The following examples are intended to explain the invention further, but without restricting its scope.

BeispieleExamples 1. Herstellung von Lactobionsäure-N-Oleylamid:1. Preparation of lactobionic acid-N-oleylamide:

500 g Lactobionsäurelacton wurden in einem Mörser fein gerieben und dann portionsweise bei 50 bis 60°C in 1,6 l Methanol gelöst. In diese Lösung wurden 324,4 g geschmolzenes Oleylamin unter Rühren zugegeben. Diese gesamte, noch klare Lösung wurde 1 Stunde bei Raumtemperatur gerührt und anschließend für ca. 12 Stunden stehengelassen. Es fiel ein weißer Niederschlag aus, der abfiltriert, mit Methanol gewaschen und dann im Vakuumtrockenschrank bei 30°C getrocknet wurde. Die Ausbeute betrug 93 Gew.-% Lactobionsäure-N-Oleylamid, bezogen auf Lactobionsäurelacton.500 g of lactobionic acid lactone were finely ground in a mortar and then dissolved in portions in 1.6 l of methanol at 50 to 60 ° C. Into this solution were added 324.4 g of molten oleylamine added with stirring. This entire, still clear solution was stirred for 1 hour at room temperature and then left to stand for about 12 hours. A white precipitate precipitated out, which was filtered off, washed with methanol and then dried in a vacuum drying cabinet at 30 ° C. The yield was 93% by weight of lactobionic acid-N-oleylamide, based on lactobionic acid lactone.

Wie beispielhaft für Lactobionsäure-N-Oleylamid beschrieben, erfolgte auch die Herstellung der übrigen Lactobionsäureamide.As described by way of example for lactobionic acid N-oleylamide, the other lactobionic acid amides were also prepared.

2. Bestimmung der Korrosionsschutzeigenschaften:2. Determination of the corrosion protection properties:

Die Korrosionsschutzeigenschaften wurden gemäß der DIN-Norm 51360, Teil 2, durchgeführt.The corrosion protection properties were carried out in accordance with DIN standard 51360, part 2.

Graugußspäne (Werkstoff DIN 1691-GG30 von etwa 5 mm x 5 mm-Größe) wurden mit Petrolether gewaschen, durch ein Drahtsieb gesiebt und bei ca. 105°C im Trockenschrank getrocknet. Nach der Trocknung wurde es vermieden, die Späne mit der Hand zu berühren.Gray cast iron chips (material DIN 1691-GG30 of about 5 mm x 5 mm in size) were washed with petroleum ether, sieved through a wire sieve and dried at about 105 ° C. in a drying cabinet. After drying, it was avoided to touch the chips by hand.

In eine Petri-Schale wurde ein Rundfilter aus Filtrierpapier (Durchmesser 40 mm) gelegt und mit 2 g (± 0,1 g) der getrockneten Späne gleichmäßig bestreut. Anschließend wurden die Späne mit 2 ml der zu untersuchenden Lösung mittels einer Vollpipette gleichmäßig benetzt. Es wurde der Deckel der Petri-Schale aufgelegt und die Petri-Schale für 2 Stunden bei Raumtemperatur stehengelassen. Dann wurden die Späne vom Rundfilter entfernt, das Rundfilter unter fließendem Wasser abgespült, in Aceton etwa für 5 Sekunden geschwenkt und bei Raumtemperatur getrocknet. Sofort anschließend an das Reinigen und Trocknen des Rundfilters wurde der Korrosionsgrad der Korrosionsabzeichnungen auf dem Rundfilter durch Sichtprüfung festgestellt. In der nachfolgenden Tabelle wird der ermittelte Korrosionsgrad für die erfindungsgemäßen Korrosionsschutzmittel angegeben. Zur besseren Beurteilung wurde ein Versuch nur mit reinem Leitungswasser ohne weiteren Zusatz durchgeführt. Es wurde jeweils die Korrosionsschutzwirkung für eine mit Leitungswasser angesetzte 3%ige wäßrige Lösung von Oleylamid, Kokosamid und Talgamid ermittelt. Zusätzlich wurde noch eine weitere Versuchsreihe durchgeführt, bei der der pH-Wert mit Triethanolamin auf pH 9,0 eingestellt wurde. Tabelle 1 Korrosionsgrad Wasser starke Korrosion Oleylamid Spuren von Korrosion 3 Gew.-% in H2O Kokosamid keine Korrosion 3 Gew.-% in H2O Talgamid keine Korrosion 3 Gew.-% in H2O Tabelle 2 Korrosionsgrad Wasser, pH 9,0 starke Korrosion Oleylamid, pH 9,0 leichte Korrosion 3 Gew.-% in H2O Talgamid, pH 9,0 leichte Korrosion 3 Gew.-% in H2O Kokosamid, pH 9,0 mäßige Korrosion 3 Gew.-% in H2O A round filter made of filter paper (diameter 40 mm) was placed in a Petri dish and evenly sprinkled with 2 g (± 0.1 g) of the dried chips. The chips were then uniformly wetted with 2 ml of the solution to be examined using a full pipette. The lid of the Petri dish was put on and the Petri dish was left to stand for 2 hours at room temperature. Then the chips were removed from the round filter, the round filter rinsed under running water, swirled in acetone for about 5 seconds and dried at room temperature. Immediately after cleaning and drying the round filter, the degree of corrosion of the corrosion marks on the round filter was determined by visual inspection. The degree of corrosion determined for the anticorrosive agents according to the invention is given in the table below. For For better assessment, a test was only carried out with pure tap water without any additional additives. The corrosion protection effect for a 3% aqueous solution of oleylamide, coconut amide and tallow amide prepared with tap water was determined in each case. In addition, a further series of experiments was carried out in which the pH was adjusted to pH 9.0 using triethanolamine. Table 1 Degree of corrosion water severe corrosion Oleylamide Traces of corrosion 3% by weight in H 2 O Coconut amide no corrosion 3% by weight in H 2 O Tallow amide no corrosion 3% by weight in H 2 O Degree of corrosion Water, pH 9.0 severe corrosion Oleylamide, pH 9.0 slight corrosion 3% by weight in H 2 O Talgamide, pH 9.0 slight corrosion 3% by weight in H 2 O Coconut amide, pH 9.0 moderate corrosion 3% by weight in H 2 O

Die vorstehenden Ergebnisse belegen, daß die erfindungsgemäßen Korrosionsschutzmittel, Korrosionsschutzeigenschaften entsprechend der DIN-Norm 51360, Teil 2, besitzen.The above results prove that the anti-corrosion agents according to the invention have anti-corrosion properties in accordance with DIN standard 51360, part 2.

Claims (8)

Korrionsschutzmittel, enthaltend Lactobionsäure-N-alkylamide.Corrosion protection agent containing lactobionic acid-N-alkylamides. Korrosionsschutzmittel nach Anspruch 1, dadurch gekennzeichnet, daß es Lactobionsäure-N-alkylamide mit über die Amidfunktion gebundenen gesättigten oder teilweise ungesättigten Alkylresten mit einer Kettenlänge von 8 - 18 Kohlenstoffatomen enthält.Corrosion protection agent according to Claim 1, characterized in that it contains lactobionic acid N-alkylamides with saturated or partially unsaturated alkyl radicals with a chain length of 8-18 carbon atoms bonded via the amide function. Korrosionsschutzmittel nach Anspruch 2, dadurch gekennzeichnet, daß es Lactobionsäure-N-alkylamide enthält, welche durch Umsetzung von Lactobionsäure oder Lactobionsäurederivaten mit Fettamingemischen erhalten wurden.Corrosion protection agent according to Claim 2, characterized in that it contains lactobionic acid N-alkylamides which have been obtained by reacting lactobionic acid or lactobionic acid derivatives with fatty amine mixtures. Korrosionsschutzmittel nach Anspruch 1 bis 3, dadurch gekennzeichnet, daß es Lactobionsäure-N-alkylamide aus der Gruppe Lactobionsäure-N-Oleylamid, Lactobionsäure-N-Kokosamid, Lactobionsäure-N-Talgamid enthält.Corrosion protection agent according to Claims 1 to 3, characterized in that it contains lactobionic acid N-alkylamides from the group lactobionic acid N-oleylamide, lactobionic acid N-coconut amide, lactobionic acid N-tallow amide. Korrosionsschutzmittel nach Anspruch 1 bis 4, dadurch gekennzeichnet, daß es Lactobionsäure-N-alkylamide in einer Menge von 0,1 bis 20 Gew.-%, vorzugsgweise 1 bis 10 Gew.-%, enthält.Corrosion protection agent according to Claims 1 to 4, characterized in that it contains lactobionic acid-N-alkylamides in an amount of 0.1 to 20% by weight, preferably 1 to 10% by weight. Verwendung eines Korrosionsschutzmittels gemäß einem der Ansprüche 1 bis 5 als Additiv in Metallbearbeitungsmitteln.Use of an anti-corrosion agent according to one of claims 1 to 5 as an additive in metalworking agents. Verwendung von Lactobionsäure-N-alkylamiden in Korrosionsschutzmitteln und/oder Metallbearbeitungsmitteln.Use of lactobionic acid N-alkylamides in anti-corrosion agents and / or metal working agents. Verwendung nach Anspruch 7, dadurch gekennzeichnet, daß man Lactobionsäure-N-alkylamide mit über die Amidfunktion gebundenen gesättigten oder teilweise ungesättigten Alkylresten mit einer Kettenlänge von 8 bis 18 Kohlenstoffatomen verwendet.Use according to claim 7, characterized in that lactobionic acid-N-alkylamides with saturated or partially unsaturated alkyl radicals having a chain length of 8 to 18 carbon atoms bonded via the amide function are used.
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