EP0823494B1 - Lactobionamide containing corrosion inhibitors or corrosion preventing compositions - Google Patents
Lactobionamide containing corrosion inhibitors or corrosion preventing compositions Download PDFInfo
- Publication number
- EP0823494B1 EP0823494B1 EP97113202A EP97113202A EP0823494B1 EP 0823494 B1 EP0823494 B1 EP 0823494B1 EP 97113202 A EP97113202 A EP 97113202A EP 97113202 A EP97113202 A EP 97113202A EP 0823494 B1 EP0823494 B1 EP 0823494B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- corrosion
- lactobionic acid
- agents
- lactobionamide
- lactobionic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- 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
- C10M173/02—Lubricating compositions containing more than 10% water not containing mineral or fatty oils
-
- 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
- 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
- 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
- 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 anti-corrosion agents and corrosion inhibitors, Which Lactobionic acid alkylamine amides and / or di-lactobionic acid alkyl diamides contain.
- lactobionic acid amides are known as corrosion-inhibiting agents known.
- EP 550 278, EP 541 467, EP 688 781 and EP 748 813 are lactobionic acid alkylamides, Di-lactobionic acid amides, lactobionic acid aminamides and bisamides and their use as a surface-active agent described. In particular, these connections are based on their properties in detergents application.
- the present invention is therefore based on the object new anti-corrosion agents and anti-corrosion agents To provide agents.
- Lactobionic acid alkylaminamides their saturated or unsaturated bound via the amide function Alkyl group has a chain length of 8 to 30 carbon atoms have, and Di-Lactobionklarealkyldiamide, whose about the amide function bonded saturated or unsaturated alkyl group have a chain length of 8 to 30 carbon atoms, have a corrosion-inhibiting effect.
- the subject of the invention is the use of the compounds mentioned or their mixtures as anti-corrosion agents and / or as an additive in metalworking agents for treatment of metals.
- the treatment of the metals can be done by dipping, Coating, spraying with the agents according to the invention.
- lactobionic acid alkylaminamides and / or di-lactobionic acid alkyl diamides by the implementation of lactobionic acid or reactive Lactobionic acid derivatives, preferably lactobionic acid lactone, with an ⁇ , ⁇ -primary diamine or an ⁇ , ⁇ -primary diamine mixture were used.
- ⁇ , ⁇ primary diamines within the scope of the invention, ⁇ , ⁇ primary fatty diamines denotes the aliphatic residue of a fatty acid with 8 contain up to 30 carbon atoms.
- These fat diamonds can e.g. B. technically obtained from fatty acids in known Way to be implemented to the corresponding diamines.
- Prefers are fatty diamines or their mixtures that are made from natural occurring or technical fatty acid mixtures obtained were used. The proportion of unsaturated fatty diamines fluctuates between approx. 5 and 85% by weight.
- the corrosion protection agent used according to the invention preferably contains the lactobionic acid alkylaminamides and / or the di-lactobionic acid alkyl diamides in the form of an aqueous solution.
- the aqueous solutions can be used alone or in a mixture with other compounds used as an anti-corrosion agent or inhibitor become.
- the content of lactobionic acid derivatives, based on the aqueous solution can be the usual for anti-corrosion agents Concentration range, expediently in the concentration range from 0.01 to 20% by weight, e.g. B. in the concentration range from 0.5 to 10% by weight.
- the anti-corrosion agents or inhibitors used Lactobionic acid alkylaminamides and / or dilactobionic acid alkyl diamides in an aqueous solution may contain completely clear solutions or, in particular in the presence of other compounds, finely divided emulsions be transparent, opaque or milky.
- lactobionic acid derivatives used can also be used for corrosion protection agents usual connections, e.g. B. petroleum sulfonates, Mineral oils or other additives are mixed and used Treatment of metals can be used.
- the lactobionic acid derivatives used according to the invention show emulsifying and corrosion-inhibiting effects in mineral oil-containing, aqueous metalworking agents.
- Another The invention therefore relates to their use in particular water-containing metalworking agents. Under metal working tools are all common for metalworking Liquids, especially cooling lubricants, drilling, Cutting and grinding oils, rust removal, paint stripping and passivation agents Understood. It is therefore possible to use metalworking emulsions to produce which contain a high level of water, without rusting.
- the corrosion protection used is characterized by good corrosion protection Lactobionic acid derivatives thanks to excellent skin tolerance and high biodegradability.
- lactobionic acid derivatives The corrosion-inhibiting effect of lactobionic acid derivatives was by means of the chips / filter paper method according to the DIN 51360, part 2, determined.
- the anti-corrosion properties were determined in accordance with the DIN standard 51360, part 2.
- Gray cast iron chips (material DIN 1691-GG30 of approx. 5 mm x 5 mm size) were washed with petroleum ether, through a wire sieve sieved and dried at about 105 ° C in a drying cabinet. After drying did not 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.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
Abstract
Description
Die Erfindung betrifft Korrosionsschutzmittel und Korrosions-Inhibitoren, welche Lactobionsäurealkylaminamide und/oder Di-Lactobionsäurealkyldiamide enthalten.The invention relates to anti-corrosion agents and corrosion inhibitors, Which Lactobionic acid alkylamine amides and / or di-lactobionic acid alkyl diamides contain.
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 Ver-bindungen 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 ihnen 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 Korrosionsschutzmittel wünschenswert, die als korrosionsinhibierendes Agens einen auch unter Umweltschutzgesichtspunkten günstigen Wirkstoff auf Basis nachwachsender Rohstoffe enthalten. In many metalworking operations such. B. Cutting, grinding or drilling become anti-corrosion agents used to protect the machined metal objects from rusting to protect. Many of the usual anti-corrosion agents contain sulfur-containing compounds such. B. petroleum sulfonates or alkylarylsulfonic acids or nitrogenous ones Connections such as B. secondary amines or alkanolamines. Sulfur-containing corrosion protection agents have the disadvantage that their active ingredients are slightly sulfur-reducing Microorganisms are modified or broken down. With amine-containing Corrosion protection agents, which are secondary in particular Containing amines, there is a possibility that they are harmful to health Nitrosamines are released, which are have previously formed through uncontrolled chemical reactions. So there is still a need for new anti-corrosion agents, which these disadvantages of the prior art Technology does not have. This includes new anti-corrosion agents desirable as the corrosion inhibitor Agents also favorable from an environmental point of view Active ingredient based on renewable raw materials.
Gemäß EP 726 335 sind Lactobionsäureamide als korrosionsinhibierende Agenzien bekannt. In EP 550 278, EP 541 467, EP 688 781 und EP 748 813 werden Lactobionsäurealkylamide, Di-Lactobionsäureamide, Lactobionsäureaminamide und -bisamide sowie deren Verwendung als oberflächenaktives Mittel beschrieben. Insbesondere finden diese Verbindungen aufgrund ihrer Eigenschaften in Reinigungsmitteln Anwendung. According to EP 726 335, lactobionic acid amides are known as corrosion-inhibiting agents known. In EP 550 278, EP 541 467, EP 688 781 and EP 748 813 are lactobionic acid alkylamides, Di-lactobionic acid amides, lactobionic acid aminamides and bisamides and their use as a surface-active agent described. In particular, these connections are based on their properties in detergents application.
Der vorliegenden Erfindung liegt daher die Aufgabe zugrunde, neue Korrosionsschutzmittel und korrosionsinhibierende Agenzien zur Verfügung zu stellen.The present invention is therefore based on the object new anti-corrosion agents and anti-corrosion agents To provide agents.
Es wurde gefunden, daß Lactobionsäurealkylaminamide, deren über die Amidfunktion gebundene gesättigte oder ungesättigte Alkylgruppe eine Kettenlänge von 8 bis 30 Kohlenstoffatome aufweisen, und Di-Lactobionsäurealkyldiamide, deren über die Amidfunktion gebundene gesättigte oder ungesättigte Alkylgruppe eine Kettenlänge von 8 bis 30 Kohlenstoffatome aufweisen, eine korrosionsinhibierende Wirkung besitzen.It was found that Lactobionic acid alkylaminamides, their saturated or unsaturated bound via the amide function Alkyl group has a chain length of 8 to 30 carbon atoms have, and Di-Lactobionsäurealkyldiamide, whose about the amide function bonded saturated or unsaturated alkyl group have a chain length of 8 to 30 carbon atoms, have a corrosion-inhibiting effect.
Gegenstand der Erfindung ist die Verwendung der genannten Verbindungen oder deren Gemische als Korrosionsschutzmittel und/ oder als Additiv in Metallbearbeitungsmitteln zur Behandlung von Metallen. Die Behandlung der Metalle kann durch Tauchen, Beschichten, Besprühen mit den erfindungsgemäßen Mitteln erfolgen. The subject of the invention is the use of the compounds mentioned or their mixtures as anti-corrosion agents and / or as an additive in metalworking agents for treatment of metals. The treatment of the metals can be done by dipping, Coating, spraying with the agents according to the invention.
In einer Ausführungsform der Erfindung werden Lactobionsäurealkylaminamide und/oder Di-Lactobionsäurealkyldiamide, die durch die Umsetzung von Lactobionsäure oder reaktiven Lactobionsäurederivaten, vorzugsweise Lactobionsäurelacton, mit einem α, Ω-primären Diamin oder einem α, Ω-primären Diamingemisch erhalten wurden, verwendet. Als α, Ω-primäre Diamine im Rahmen der Erfindung werden α, Ω-primäre Fettdiamine bezeichnet, die einen aliphatischen Rest einer Fettsäure mit 8 bis 30 Kohlenstoffatome enthalten. Diese Fettdiamine können z. B. technisch aus Fettsäuren erhalten werden, die in bekannter Weise zu den entsprechenden Diaminen umgesetzt werden. Bevorzugt werden Fettdiamine oder deren Gemische, die aus natürlich vorkommenden oder technischen Fettsäuregemischen gewonnen wurden, eingesetzt. Der Anteil an ungesättigten Fettdiaminen schwankt dabei zwischen ca. 5 und 85 Gew.-%.In one embodiment of the invention, lactobionic acid alkylaminamides and / or di-lactobionic acid alkyl diamides, by the implementation of lactobionic acid or reactive Lactobionic acid derivatives, preferably lactobionic acid lactone, with an α, Ω-primary diamine or an α, Ω-primary diamine mixture were used. As α, Ω primary diamines within the scope of the invention, α, Ω primary fatty diamines denotes the aliphatic residue of a fatty acid with 8 contain up to 30 carbon atoms. These fat diamonds can e.g. B. technically obtained from fatty acids in known Way to be implemented to the corresponding diamines. Prefers are fatty diamines or their mixtures that are made from natural occurring or technical fatty acid mixtures obtained were used. The proportion of unsaturated fatty diamines fluctuates between approx. 5 and 85% by weight.
Durch Veränderung des stöchiometrischen Verhältnisses von Lactobionsäure, bzw. Lactobionsäurelacton zu α, Ω-Fett-Diamin erhält man die gewünschten Aminamide bzw. Diamide.By changing the stoichiometric ratio of Lactobionic acid, or lactobionic acid lactone to form α, Ω-fat diamine the desired aminamides or diamides are obtained.
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 manufacture are already known. Lactobionic acid can, for example, in a known manner Oxidation of lactose can be obtained.
Vorzugsweise enthält das erfindungsgemäße verwendete Korrosionsschutzmittel die Lactobionsäurealkylaminamide und/oder die Di-Lactobionsäurealkyldiamide in Form einer wäßrigen Lösung. Die wäßrigen Lösungen können dabei alleine oder auch im Gemisch mit weiteren Verbindungen als Korrosionsschutzmittel oder -Inhibitor eingesetzt werden. Der Gehalt an Lactobionsäurederivaten, bezogen auf die wäßrige Lösung, kann dabei im für Korrosionsschutzmittel üblichen Konzentrationsbereich, zweckmäßigerweise im Konzentrationsbereich von 0,01 bis 20 Gew.-%, z. B. im Konzentrationsbereich von 0,5 bis 10 Gew.-%, liegen.The corrosion protection agent used according to the invention preferably contains the lactobionic acid alkylaminamides and / or the di-lactobionic acid alkyl diamides in the form of an aqueous solution. The aqueous solutions can be used alone or in a mixture with other compounds used as an anti-corrosion agent or inhibitor become. The content of lactobionic acid derivatives, based on the aqueous solution, can be the usual for anti-corrosion agents Concentration range, expediently in the concentration range from 0.01 to 20% by weight, e.g. B. in the concentration range from 0.5 to 10% by weight.
Die verwendeten Korrosionsschutzmittel bzw. -Inhibitoren, die Lactobionsäurealkylaminamide und/oder Dilactobionsäurealkyldiamide in einer wäßrigen Lösung enthalten, können vollständig klare Lösungen oder, insbesondere bei Gegenwart anderer Verbindungen, feinverteilte Emulsionen sein, die transparent, opak oder auch milchig trüb sein können.The anti-corrosion agents or inhibitors used Lactobionic acid alkylaminamides and / or dilactobionic acid alkyl diamides in an aqueous solution may contain completely clear solutions or, in particular in the presence of other compounds, finely divided emulsions be transparent, opaque or milky.
Die verwendeten Lactobionsäurederivate können mit für Korrosionsschutzmittel üblichen Verbindungen, z. B. Petrolsulfonate, Mineralöle oder andere Additive gemischt werden und zur Behandlung der Metalle verwendet werden.The lactobionic acid derivatives used can also be used for corrosion protection agents usual connections, e.g. B. petroleum sulfonates, Mineral oils or other additives are mixed and used Treatment of metals can be used.
Die erfindungsgemäß verwendeten Lactobionsäurederivate zeigen emulgierende und korrosionsinhibierende Wirkung in mineralölhaltigen, wäßrigen Metallbearbeitungsmitteln. Ein weiterer Gegenstand der Erfindung ist daher deren Verwendung in insbesondere wasserhaltigen Metallbearbeitungsmitteln. Unter Metallbearbeitungsmitteln werden dabei alle zur Metallbearbeitung üblichen Flüssigkeiten, insbesondere Kühlschmiermittel, Bohr-, Schneid- und Schleiföle, Entrostungs-, Entlackungs- und Passivierungsmittel verstanden. Es ist daher möglich, Metallbearbeitungsemulsionen herzustellen, welche in hohem Maße Wasser enthalten, ohne daß es dabei zur Rostbildung kommt. Neben einem guten Korrosionsschutz zeichnen sich die erfindungsgemäß verwendeten Lactobionsäurederivate durch eine ausgezeichnete Hautverträglichkeit und hohe biologische Abbaubarkeit aus.The lactobionic acid derivatives used according to the invention show emulsifying and corrosion-inhibiting effects in mineral oil-containing, aqueous metalworking agents. Another The invention therefore relates to their use in particular water-containing metalworking agents. Under metal working tools are all common for metalworking Liquids, especially cooling lubricants, drilling, Cutting and grinding oils, rust removal, paint stripping and passivation agents Understood. It is therefore possible to use metalworking emulsions to produce which contain a high level of water, without rusting. Besides one The corrosion protection used is characterized by good corrosion protection Lactobionic acid derivatives thanks to excellent skin tolerance and high biodegradability.
Die korrosionsinhibierende Wirkung der Lactobionsäurederivate wurde mittels des Späne/Filterpapier-Verfahrens nach der DIN 51360, Teil 2, ermittelt. The corrosion-inhibiting effect of lactobionic acid derivatives was by means of the chips / filter paper method according to the DIN 51360, part 2, determined.
Die nachfolgenden Beispiele sollen die Erfindung weiter erläutern, ohne sie jedoch in ihrem Umfang zu begrenzen.The following examples are intended to further illustrate the invention explain, but without limiting their scope.
500 g (1,47 mol) Lactobionsäurelacton werden bei 40 °C in ca. 2 l Methanol gelöst. Zu dieser Lösung werden 200 g (1 mol) 1,12 Diaminododecan schnell eingetragen. Nach 12 Stunden Reaktionszeit wird der entstehende Niederschlag abfiltriert, mit Methanol nachgewaschen und im Trockenschrank getrocknet. Zur Entfernung von Di-Lactobionsäuredodecandiamid wird eine wäßrige Lösung des Substanzgemisches über einen sauren Ionenaustauscher (z. B. IRA 252) gegeben. Der Durchlauf enthält neben dem unerwünschten Diamid überschüssige Lactobionsäure. Nach Elution des Ionenaustauschers mit 2n NH4OH-Lösung werden nach Entfernung des Wassers und Trocknung des Produktes im Vakuumtrockenschrank 383 g (entspricht 71 % der Theorie) Lactobion-12-amino-dodecanamid erhalten. 500 g (1.47 mol) of lactobionic acid lactone are dissolved in about 2 l of methanol at 40 ° C. 200 g (1 mol) 1.12 diaminododecane are quickly added to this solution. After a reaction time of 12 hours, the precipitate formed is filtered off, washed with methanol and dried in a drying cabinet. To remove di-lactobionic acid dodecanediamide, an aqueous solution of the substance mixture is passed through an acidic ion exchanger (eg IRA 252). In addition to the undesirable diamide, the run contains excess lactobionic acid. After elution of the ion exchanger with 2N NH 4 OH solution, 383 g (corresponds to 71% of theory) of lactobion-12-amino-dodecanamide are obtained after removal of the water and drying of the product in a vacuum drying cabinet.
500 g (1,47 mol) Lactobionsäurelacton werden bei 50 bis 60 °C in ca. 1,6 l Methanol gelöst und mit 140 g (0,7 mol) 1,12-Diaminododecan versetzt. Nach 12 Stunden Reaktionszeit bei Raumtemperatur wird der erhaltene Niederschlag abfiltriert, mit Methanol nachgewaschen und im Vakuumtrockenschrank bei 40 bis 50 °C getrocknet. Man erhält 486 g (entspricht 76 % der Theorie) als cremefarbenes Pulver Di-Lactobionsäuredodecandiamid.500 g (1.47 mol) of lactobionic acid lactone are at 50 to 60 ° C. dissolved in about 1.6 l of methanol and with 140 g (0.7 mol) of 1,12-diaminododecane transferred. After a reaction time of 12 hours at room temperature the precipitate obtained is filtered off with Washed methanol and in a vacuum drying cabinet at 40 to 50 ° C dried. 486 g are obtained (corresponds to 76% of theory) as a cream-colored powder di-lactobionic acid dodecanediamide.
Die Korrosionsschutzeigenschaften wurden gemäß der DIN-Norm 51360, Teil 2, durchgeführt.The anti-corrosion properties were determined in accordance with the 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 approx. 5 mm x 5 mm size) were washed with petroleum ether, through a wire sieve sieved and dried at about 105 ° C in a drying cabinet. After drying did not 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 Lactobion-12-aminododecanamid
und Di-Lactobiondodecan-1,12-diamid ermittelt.
Die vorstehenden Ergebnisse belegen, daß die erfindungsgemäßen Korrosionsschutzmittel, Korrosionsschutzeigenschaften entsprechend der DIN-Norm 51360, Teil 2, besitzen.The above results show that the inventive Corrosion protection agent, corrosion protection properties accordingly the DIN standard 51360, part 2.
Claims (2)
- Use of lactobionic acid alkylamine amides with saturated or partially unsaturated alkyl residues bonded by the amide function and having a chain length of 8 to 30 carbon atoms, and/or of dilactobionic acid alkyl diamides with saturated or partially unsaturated alkyl residues bonded by the amide function and having a chain length of 8 to 30 carbon atoms, as anticorrosive agent and/or additive in metalworking auxiliaries.
- Use of lactobionic acid alkylamine amides and/or dilactobionic acid alkyl diamides according to Claim 1, characterized in that they are used in an amount of 0.01 to 20 % by weight, preferably 0.5 to 10 % by weight.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19631959 | 1996-08-08 | ||
| DE19631959A DE19631959A1 (en) | 1996-08-08 | 1996-08-08 | Corrosion inhibitors and corrosion inhibitors containing lactobionic acid amides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0823494A1 EP0823494A1 (en) | 1998-02-11 |
| EP0823494B1 true EP0823494B1 (en) | 1999-12-29 |
Family
ID=7802080
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP97113202A Expired - Lifetime EP0823494B1 (en) | 1996-08-08 | 1997-07-31 | Lactobionamide containing corrosion inhibitors or corrosion preventing compositions |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US5795851A (en) |
| EP (1) | EP0823494B1 (en) |
| AT (1) | ATE188263T1 (en) |
| DE (2) | DE19631959A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6846788B2 (en) | 2001-06-07 | 2005-01-25 | Ecolab Inc. | Methods for removing silver-oxide |
| US8136236B2 (en) * | 2009-09-15 | 2012-03-20 | John Mezzalingua Associates, Inc. | Method for manufacturing a coaxial cable |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2752334A (en) * | 1952-03-01 | 1956-06-26 | Nat Dairy Res Lab Inc | Nu-substituted lactobionamides |
| FR2683223B1 (en) * | 1991-11-05 | 1995-04-28 | Stepan Europe | AMPHIPHILIC COMPOUNDS WITH DOUBLE HEAD SUGAR SURFACTANT AND VESICULAR AGENT COMPRISING SUCH A COMPOUND AND PROCESS FOR PREPARING SAID COMPOUND. |
| US5336765A (en) * | 1991-12-31 | 1994-08-09 | Lever Brothers Company, Division Of Conopco, Inc. | Process of preparing N-substituted aldobionamides |
| US5296588A (en) * | 1991-12-31 | 1994-03-22 | Lever Brothers Company, Division Of Conopco, Inc. | Process of preparing N-substituted aldonamides |
| US5389279A (en) * | 1991-12-31 | 1995-02-14 | Lever Brothers Company, Division Of Conopco, Inc. | Compositions comprising nonionic glycolipid surfactants |
| DE4215478A1 (en) * | 1992-05-11 | 1993-11-18 | Solvay Deutschland | Lactobionic acid amide compositions and their use |
| US5401839A (en) * | 1993-03-23 | 1995-03-28 | Lever Brothers Company, Division Of Conopco, Inc. | Process of preparing N-substituted aldonamides having improved color and color stability |
| GB9412140D0 (en) * | 1994-06-17 | 1994-08-10 | Kodak Ltd | Non-ionic surface active compounds |
| GB9424444D0 (en) * | 1994-12-02 | 1995-01-18 | Unilever Plc | Detergent compositions |
| DE19504639A1 (en) * | 1995-02-13 | 1996-08-14 | Solvay Deutschland | Corrosion inhibitors containing lactobionic acid amides |
| EP0748813B1 (en) * | 1995-06-15 | 2000-03-29 | Akzo Nobel N.V. | Process for preparing an N-substituted aldonamide |
-
1996
- 1996-08-08 DE DE19631959A patent/DE19631959A1/en not_active Withdrawn
-
1997
- 1997-07-31 AT AT97113202T patent/ATE188263T1/en not_active IP Right Cessation
- 1997-07-31 EP EP97113202A patent/EP0823494B1/en not_active Expired - Lifetime
- 1997-07-31 DE DE59700922T patent/DE59700922D1/en not_active Expired - Fee Related
- 1997-08-08 US US08/908,809 patent/US5795851A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ATE188263T1 (en) | 2000-01-15 |
| US5795851A (en) | 1998-08-18 |
| DE19631959A1 (en) | 1998-02-12 |
| EP0823494A1 (en) | 1998-02-11 |
| DE59700922D1 (en) | 2000-02-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0222311B1 (en) | Use of alkoxy-hydroxy-substituted fatty acids as corrosion inhibitors in oils and emulsions containing oil | |
| DE3837811C1 (en) | ||
| EP0058711B1 (en) | Process and product for the passivation of iron and steel surfaces | |
| DE2943963C2 (en) | ||
| EP0099598A1 (en) | Solution for the anti-corrosive treatment of metallic surfaces, and concentrate for preparing it | |
| EP0823494B1 (en) | Lactobionamide containing corrosion inhibitors or corrosion preventing compositions | |
| DE1302095B (en) | Liquid, storage-stable concentrates and cleaning and degreasing agents that can be prepared from them by diluting them with water | |
| EP1354905A2 (en) | Method for producing ether-carboxylic acids having low pour point | |
| DE2524543A1 (en) | BACTERICIDAL ADDITIVE FOR OIL-IN-WATER EMULSIONS | |
| EP0726335B1 (en) | Lactobionamide containing corrosion inhibiting composition | |
| EP0566956B1 (en) | Corrosion inhibitor | |
| EP0144738B1 (en) | Succinic monodialkyl amides as water-soluble corrosion inhibitors | |
| EP0034726B1 (en) | Process for the manufacture of reaction products from fatty acids and alkanol amines and the use of the reaction products as technical emulsifiers | |
| EP0231524B1 (en) | Application of alkylbenzoylacrylic acids as corrosion inhibitors | |
| DE3300874A1 (en) | Succinic acid derivatives as corrosion protection agents | |
| EP0216280B1 (en) | Use of alkenylsuccinic monoamides as corrosion inhibitors | |
| DE3808372A1 (en) | REACTION PRODUCTS FROM BORSAEUR AND ALKANOLETHERAMINES AND THEIR USE THEREOF AS A CORROSION PROTECT | |
| DE10043040A1 (en) | Use of N-alkyl-beta-alanine derivatives for the production of cleaning anti-corrosion agents | |
| WO1995002714A1 (en) | Agents for the cleaning and passivation of metal surfaces | |
| DE3701719A1 (en) | Corrosion protection agent, containing mixtures with amido acids | |
| EP0109549B1 (en) | Corrosion inhibitors for aqueous solutions for the treatment of metals, and process for their preparation | |
| DE3208748A1 (en) | Epoxide-phosphoric acid adducts and process for their preparation | |
| EP0015442A1 (en) | Low-foaming corrosion inhibitors with microbiocidal properties, that contain alcanolamine-boric acid reaction products as the active ingredients | |
| EP0109548B1 (en) | Corrosion inhibitors for aqueous solutions for the treatment of metals, and process for their preparation | |
| EP0015491B1 (en) | Aqueous emulsions for metal working and concentrates for their preparation |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE CH DE FR GB IT LI NL |
|
| 17P | Request for examination filed |
Effective date: 19980811 |
|
| AKX | Designation fees paid |
Free format text: AT BE CH DE FR GB IT LI NL |
|
| RBV | Designated contracting states (corrected) |
Designated state(s): AT BE CH DE FR GB IT LI NL |
|
| 17Q | First examination report despatched |
Effective date: 19980922 |
|
| GRAG | Despatch of communication of intention to grant |
Free format text: ORIGINAL CODE: EPIDOS AGRA |
|
| GRAG | Despatch of communication of intention to grant |
Free format text: ORIGINAL CODE: EPIDOS AGRA |
|
| GRAH | Despatch of communication of intention to grant a patent |
Free format text: ORIGINAL CODE: EPIDOS IGRA |
|
| GRAH | Despatch of communication of intention to grant a patent |
Free format text: ORIGINAL CODE: EPIDOS IGRA |
|
| GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
| AK | Designated contracting states |
Kind code of ref document: B1 Designated state(s): AT BE CH DE FR GB IT LI NL |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: NL Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 19991229 Ref country code: IT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT;WARNING: LAPSES OF ITALIAN PATENTS WITH EFFECTIVE DATE BEFORE 2007 MAY HAVE OCCURRED AT ANY TIME BEFORE 2007. THE CORRECT EFFECTIVE DATE MAY BE DIFFERENT FROM THE ONE RECORDED. Effective date: 19991229 Ref country code: GB Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 19991229 Ref country code: FR Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 19991229 |
|
| REF | Corresponds to: |
Ref document number: 188263 Country of ref document: AT Date of ref document: 20000115 Kind code of ref document: T |
|
| REG | Reference to a national code |
Ref country code: CH Ref legal event code: EP |
|
| REF | Corresponds to: |
Ref document number: 59700922 Country of ref document: DE Date of ref document: 20000203 |
|
| EN | Fr: translation not filed | ||
| NLV1 | Nl: lapsed or annulled due to failure to fulfill the requirements of art. 29p and 29m of the patents act | ||
| GBV | Gb: ep patent (uk) treated as always having been void in accordance with gb section 77(7)/1977 [no translation filed] |
Effective date: 19991229 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: BE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20000731 Ref country code: AT Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20000731 |
|
| PLBE | No opposition filed within time limit |
Free format text: ORIGINAL CODE: 0009261 |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT |
|
| 26N | No opposition filed | ||
| BERE | Be: lapsed |
Owner name: SOLVAY DEUTSCHLAND G.M.B.H. Effective date: 20000731 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: DE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20010501 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: LI Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20010731 Ref country code: CH Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20010731 |
|
| REG | Reference to a national code |
Ref country code: CH Ref legal event code: PL |