EP0557839A1 - Low and high molecular weight corrosion inhibiting additives based on epoxides - Google Patents
Low and high molecular weight corrosion inhibiting additives based on epoxides Download PDFInfo
- Publication number
- EP0557839A1 EP0557839A1 EP93102317A EP93102317A EP0557839A1 EP 0557839 A1 EP0557839 A1 EP 0557839A1 EP 93102317 A EP93102317 A EP 93102317A EP 93102317 A EP93102317 A EP 93102317A EP 0557839 A1 EP0557839 A1 EP 0557839A1
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- European Patent Office
- Prior art keywords
- molecular weight
- acids
- oils
- high molecular
- low
- Prior art date
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Classifications
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- 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
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
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- 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
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/66—Epoxidised acids or esters
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- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/24—Epoxidised acids; Ester derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/40—Fatty vegetable or animal 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/40—Fatty vegetable or animal oils
- C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
-
- 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
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
-
- 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
- C10N2040/02—Bearings
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/135—Steam engines or turbines
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Paints Or Removers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Fats And Perfumes (AREA)
Abstract
Description
Metallische Gegenstände oder Konstruktionen, die abgeschmiert oder durch Öle oder Fette geschützt werden, benötigen häufig einen wirksamen Schutz gegen Korrosion. Aus diesem Grund wird den Ölen oder Fetten ein Inhibitor zugesetzt. Zweckmäßig ist dies bei Motorenfetten, hydraulischen Ölen, Schmierölen, bei den meisten Schmierfetten und den temporären Rostschutzmitteln.Metallic objects or structures that are lubricated or protected by oils or greases often need effective protection against corrosion. For this reason, an inhibitor is added to the oils or fats. This is useful for engine greases, hydraulic oils, lubricating oils, most lubricating greases and temporary rust inhibitors.
Im Laufe der Zeit ist es gelungen, Inhibitoren zu entwickeln, die in Ölen oder Fetten als oxidierende Inhibitoren (Passivatoren) oder als Adsorptionsinhibitoren wirken oder gleichzeitig auf beide Arten. Beispiele für oxidierende Inhibitoren sind Natriumnitrit oder Lithiumnitrit, welche als feste Salze im Fett feinverteilt werden können, ferner bestimmte organische Nitrite oder Chromate. Die größte Gruppe der in Öl eingesetzten Inhibitoren sind Adsorptionsinhibitoren, die häufig aus Stickstoff- oder Schwefelverbindungen bestehen. Hierher gehören auch die Amine, welche entweder als solche oder als Salze niedriger Alkan-Carbonsäuren verwendet werden.Over time, it has been possible to develop inhibitors which act in oils or fats as oxidizing inhibitors (passivators) or as adsorption inhibitors, or both at the same time. Examples of oxidizing inhibitors are sodium nitrite or lithium nitrite, which can be finely divided as solid salts in the fat, and also certain organic nitrites or chromates. The largest group of inhibitors used in oil are adsorption inhibitors, which often consist of nitrogen or sulfur compounds. This subheading also includes the amines, which are used either as such or as salts of lower alkane-carboxylic acids.
Die wichtigsten in Öl eingesetzten Inhibitoren sind die Alkali- und Erdalkalisalze höhermolekularer Sulfonsäuren, die man durch Neutralisation von sulfonierten Ölen (Petroleumsulfonate, Synthesesulfonate) erhält. Es handelt sich hier um höhermolekulare Verbindungen, die über ihre polare Sulfonsäuregruppe auf der ganzen Metalloherfläche adsorbiert werden. Sie wirken dabei im allgemeinen auf doppelte Weise; d.h., sie verzögern sowohl die anodische als auch die kathodische Reaktion. Der lipophile Teil solcher Verbindungen trägt zur besseren Löslichkeit in Mineralölen bei.The most important inhibitors used in oil are the alkali and alkaline earth salts of high molecular weight sulfonic acids, which are obtained by neutralizing sulfonated oils (petroleum sulfonates, synthesis sulfonates). These are higher molecular weight compounds which are adsorbed on the entire metal surface via their polar sulfonic acid group. They generally work in two ways; that is, they delay both the anodic and cathodic reactions. The lipophilic part of such compounds contributes to better solubility in mineral oils.
Ein Nachteil der Erdalkalimetallsulfonate ist, daß bei Kombination mit anderen Additiven schwerlösliche Erdalkalimetallsalze entstehen können, die durch Ablagerungen auf den Metalloberflächen die tribologische Wirksamkeit beeinträchtigen können. Es können auch bei hohen Verarbeitungstemperaturen, bei denen die Öle verdampfen bzw. verbrennen, anorganische Salze auf der Metalloberfläche zurückbleiben, die z.B. beim Walzen von Feinstblechen störend sind. Ein weiterer Nachteil ist, daß bei der Herstellung metallhaltiger Sulfonate schwermetallhaltige Rückstände wie Bariumsulfat und Zinksulfat anfallen.A disadvantage of the alkaline earth metal sulfonates is that, when combined with other additives, poorly soluble alkaline earth metal salts can form, which can impair the tribological activity due to deposits on the metal surfaces. Even at high processing temperatures at which the oils evaporate or burn, inorganic salts may remain on the metal surface, e.g. are annoying when rolling thin sheets. Another disadvantage is that heavy metal residues such as barium sulfate and zinc sulfate are produced in the production of metal-containing sulfonates.
Die Anwendung metallhaltiger Korrosionsinhibitoren, insbesondere in offenen Tribosystemen ist eingeschränkt, da in Folge ihres hohen Metallgehaltes die biologische Abbaubarkeit durch Störung mikrobieller Abbauprozesse verzögert werden kann.The use of metal-containing corrosion inhibitors, in particular in open tribosystems, is restricted because, owing to their high metal content, the biodegradability can be delayed by disrupting microbial degradation processes.
Aufgabe der Erfindung ist, sulfonatähnliche Verbindungen bereitzustellen, die als Zusätze zu Mineralölen, Fetten und insbesondere nativen Ölen wie Rapsöl, guten Korrosionsschutz bewirken.The object of the invention is to provide sulfonate-like compounds which, as additives to mineral oils, fats and in particular native oils such as rapeseed oil, provide good corrosion protection.
Es wurde gefunden, daß Umsetzungsprodukte von epoxidierten Fettsäureestern, vorzugsweise den Methylestern solcher Fettsäuren mit höhermolekularen Sulfonsäuren, die geforderten Eigenschaften besitzen.It has been found that reaction products of epoxidized fatty acid esters, preferably the methyl esters of such fatty acids with higher molecular weight sulfonic acids, have the required properties.
Gegenstand der Erfindung ist daher die Verwendung epoxidierter und anschließend mit nieder- oder höhermolekularen Sulfonsäuren umgesetzter Fettsäureester, insbesondere Methylester ungesättigter Fettsäuren als korrosionshemmender Zusatz zu Schmierölen, insbesondere Schmierölen pflanzlicher Herkunft.The invention therefore relates to the use of epoxidized fatty acid esters and subsequently reacted with low or higher molecular weight sulfonic acids, in particular methyl esters of unsaturated fatty acids, as a corrosion-inhibiting additive to lubricating oils, in particular lubricating oils of vegetable origin.
Die erfindungsgemäß verwendeten Umsetzungsprodukte können wie folgt hergestellt werden:
Zur Umsetzung geeignete Sulfonsäuren sind z.B. höhermolekulare Monoalkylbenzolsulfonsäuren oder Dialkylbenzolsulfonsäuren. Als epoxidierte Fettsäureester werden bevorzugt die epoxidierten Methylester ungesättigter Fettsäuren oder Fettsäuregemische, z.B. Rüböl, Leinöl, Sojaöl oder Fischöl zugrundeliegende Fettsäuren eingesetzt. Die genannten Sulfonsäuren werden mit den epoxidierten Fettsäureestern, die Epoxidgehalte von 1,5 - 15 Gew.-% (Gew.-% Sauerstoff, bezogen auf epoxidierten Methylester), vorzugsweise 4 - 8 Gew.-% aufweisen, in Mengen von 10 - 60 Gew.-% (bezogen auf epoxidierten Fettsäureester) bei Temperaturen von 20 - 120°C, vorzugsweise bei 30 - 60°C, umgesetzt, wobei flüssige Produkte erhalten werden. Die Menge der Sulfonsäuren wird so bemessen, daß auf ein Mol Epoxidgruppen etwa ein Mol reaktionsfähige Sulfonsäuregruppe kommt. Bei nicht vollständiger stöchiometrischer Umsetzung soll das Reaktionsprodukt vorzugsweise noch Epoxidgruppen enthalten. Bevorzugte Sulfonsäuren sind höhermolekulare Dialkylbenzolsulfonsäuren.The reaction products used according to the invention can be prepared as follows:
Sulfonic acids suitable for the reaction are, for example, higher molecular weight monoalkylbenzenesulfonic acids or dialkylbenzenesulfonic acids. The epoxidized fatty acid esters are preferably the epoxidized methyl esters of unsaturated fatty acids or fatty acid mixtures, for example rapeseed oil, linseed oil, soybean oil or fish oil Fatty acids used. The sulfonic acids mentioned with the epoxidized fatty acid esters, which have epoxide contents of 1.5-15% by weight (% by weight of oxygen, based on epoxidized methyl ester), preferably 4-8% by weight, in amounts of 10-60 % By weight (based on epoxidized fatty acid esters) at temperatures of 20-120 ° C., preferably at 30-60 ° C., to give liquid products. The amount of sulfonic acids is such that there is about one mole of reactive sulfonic acid group per mole of epoxy groups. If the stoichiometric conversion is not complete, the reaction product should preferably also contain epoxy groups. Preferred sulfonic acids are higher molecular weight dialkylbenzenesulfonic acids.
Die erhaltenen Reaktionsprodukte werden Ölen, insbesondere nativen Ölen, in Mengen von 0,01 - 70 Gew.-%, bevorzugt 0,05 bis 5 Gew.-%, bezogen auf reines Öl zugesetzt und verleihen diesen bedeutend bessere Korrosionsschutzeigenschaften als herkömmliche Korrosionsinhibitoren wie Metallsulfonate und Metallnaphthenate.The reaction products obtained are added to oils, in particular native oils, in amounts of 0.01-70% by weight, preferably 0.05 to 5% by weight, based on pure oil, and give them significantly better corrosion protection properties than conventional corrosion inhibitors such as metal sulfonates and metal naphthenates.
Je nach eingesetzter Sulfonsäure bzw. epoxidiertem Fettsäuremethylester können demulgierende oder emulgierende Produkte erhalten werden. Insbesondere für Hydraulik-, Getriebe- und Dampfturbinenöle bei denen HLP- und CLP-Anforderungen vorgeschrieben sind, ist der Einsatz von Schmierstoffen mit gutem Demulgierverhalten erforderlich.Depending on the sulfonic acid or epoxidized fatty acid methyl ester used, demulsifying or emulsifying products can be obtained. In particular for hydraulic, gear and steam turbine oils for which HLP and CLP requirements are prescribed, the use of lubricants with good demulsifying behavior is necessary.
Hydrauliköle HLP nach DIN 51 524 Teil 2 sind Druckflüssigkeiten aus Mineralölen mit Wirkstoffen zum Erhöhen des Korrosionsschutzes, der Alterungsheständigkeit und zur Verminderung des Fressverschleißes. Schmieröle CLP nach DIN 51 517 Teil 3 sind Mineralöle mit Wirkstoffen zum Erhöhen des Korrosionsschutzes und der Alterungsbeständigkeit sowie Wirkungen zum Herabsetzen des Verschleißes.Hydraulic oils HLP according to DIN 51 524 Part 2 are hydraulic fluids made from mineral oils with active ingredients to increase corrosion protection, aging resistance and reduce seizure wear. Lubricating oils CLP according to DIN 51 517 Part 3 are mineral oils with active substances to increase the protection against corrosion and the aging resistance as well as effects to reduce the wear.
Damit in Hydraulikanlagen keine Störungen auftreten, müssen Hydrauliköle durch extrem feine Filter (z.B. 3 µm) gut filtrierbar sein. Die erfindungsgemäßen Reaktionsprodukte enthalten im Gegensatz zu herkömmlichen Sulfonaten keine Metallverbindungen, die oft die Filtrierbarkeit stören oder gar unmöglich machen und sind daher besonders gut filtrierbar.To ensure that no malfunctions occur in hydraulic systems, hydraulic oils must be easy to filter through extremely fine filters (eg 3 µm). In contrast to conventional sulfonates, the reaction products according to the invention contain no metal compounds which often interfere with the filterability or even make it impossible, and are therefore particularly easy to filter.
Die erfindungsgemäßen Reaktionsprodukte eignen sich aufgrund ihrer wasserabweisenden und korrosionsschützenden Eigenschaften als Zusatz zu Dewatering-Fluids auf Basis von tiefsiedenen Kohlenwasserstoffen.Because of their water-repellent and corrosion-protecting properties, the reaction products according to the invention are suitable as an additive to dewatering fluids based on low-boiling hydrocarbons.
Aufgrund ihrer hohen Affinität zu biologisch schnell abbaubaren Grundölen wie Rapsöl, Sojaöl, Syntheseester, sind sie geeignete Additive zur Formulierung von biologisch schnell abbaubaren Schmierstoffen. Ihre biologische Abbaubarkeit ist durch die Verwendung von epoxidierten nativen Rohstoffen und das Fehlen von Metallionen wesentlich besser als die herkömmlicher Additive z.B. Metallsulfonate.Due to their high affinity for rapidly biodegradable base oils such as rapeseed oil, soybean oil, synthetic esters, they are suitable additives for the formulation of rapidly biodegradable lubricants. Their biodegradability is significantly better than that of conventional additives such as metal sulfonates due to the use of epoxidized native raw materials and the lack of metal ions.
500 g Monoalkylbenzolsulfonsäure mit einer Säurezahl vom 78 mg KOH/g Substanz und 300 g Rüböl werden unter Rühren auf 40°C erwärmt. Dazu gibt man innerhalb von 60 min portionsweise 400 g epoxidiertes Rüböl mit einem Epoxid-Gehalt von 5 Gew.-%. Anschließend läßt man noch 4 Stunden bei 40°C nachreagieren. Das erhaltene Reaktionsprodukt kann ohne weitere Aufarbeitung als Korrosionsschutz-Additiv eingesetzt werden.500 g monoalkylbenzenesulfonic acid with an acid number of 78 mg KOH / g substance and 300 g turnip oil are heated to 40 ° C. with stirring. 400 g of epoxidized beet oil with an epoxy content of 5% by weight are added in portions within 60 minutes. Then allowed to react for a further 4 hours at 40 ° C. The reaction product obtained can be used as a corrosion protection additive without further workup.
500 g Dialkylbenzolsulfonsäure mit einer Säurezahl vom 80 mg KOH/g Substanz und 300 g Rüböl werden unter Rühren auf 40°C erwärmt. Dazu gibt man innerhalb von 60 min portionsweise 195 g 2-Ethylhexylglycidylether. Anschließend läßt man noch 4 Stunden bei 40°C nachreagieren. Das erhaltende Reaktionsprodukt kann ohne weitere Aufarbeitung als Korrosionsschutz-Additiv eingesetzt werden.500 g dialkylbenzenesulfonic acid with an acid number of 80 mg KOH / g substance and 300 g turnip oil are heated to 40 ° C. with stirring. 195 g of 2-ethylhexylglycidyl ether are added in portions within 60 minutes. Then allowed to react for a further 4 hours at 40 ° C. The reaction product obtained can be used as a corrosion protection additive without further workup.
500 g epoxidierter Rübölsäuremethylester mit einem Epoxid-Gehalt von 5 Gew.-% wird auf 40°C erwärmt. Dazu gibt man innerhalb von 60 min portionsweise 660 g Monoalkylbenzolsulfonsäure mit einer Säurezahl von 78 mg KOH/g Substanz. Anschließend läßt man noch 4 Stunden bei 40°C nachreagieren. Das erhaltende Reaktionsprodukt kann ohne weitere Aufarbeitung als Korrosionsschutz-Additiv eingesetzt werden.500 g of epoxidized rape oleic acid methyl ester with an epoxy content of 5% by weight is heated to 40 ° C. 660 g of monoalkylbenzenesulfonic acid with an acid number of 78 mg of KOH / g of substance are added in portions within 60 minutes. Then allowed to react for a further 4 hours at 40 ° C. The reaction product obtained can be used as a corrosion protection additive without further workup.
Claims (2)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4206047 | 1992-02-27 | ||
| DE4206047A DE4206047A1 (en) | 1992-02-27 | 1992-02-27 | LOW AND HIGH MOLECULAR CORROSION PROTECTION ADDITIVES BASED ON EPOXIES |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0557839A1 true EP0557839A1 (en) | 1993-09-01 |
| EP0557839B1 EP0557839B1 (en) | 1997-04-09 |
Family
ID=6452731
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP93102317A Expired - Lifetime EP0557839B1 (en) | 1992-02-27 | 1993-02-15 | Low and high molecular weight corrosion inhibiting additives based on epoxides |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0557839B1 (en) |
| JP (1) | JPH0625687A (en) |
| AT (1) | ATE151449T1 (en) |
| DE (2) | DE4206047A1 (en) |
| DK (1) | DK0557839T3 (en) |
| ES (1) | ES2099852T3 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4079830A1 (en) | 2021-04-19 | 2022-10-26 | Marteen Sports World, S.L. | Biodegradable lubricant composition |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2763615A (en) * | 1953-04-16 | 1956-09-18 | Monsanto Chemicals | Carboxylic acid derivatives and lubricants containing them |
| US3096357A (en) * | 1960-05-04 | 1963-07-02 | Bohme Fettchemie Gmbh | Novel reaction products of a sulfuric acid and epoxides |
| FR1570355A (en) * | 1967-06-30 | 1969-06-06 | ||
| EP0247467A2 (en) * | 1986-05-24 | 1987-12-02 | Henkel Kommanditgesellschaft auf Aktien | Use of salts from esters of long chain fatty alcohols with alpha-sulfofatty acids |
| EP0335429A2 (en) * | 1988-03-22 | 1989-10-04 | King Industries, Inc. | Amine dinonylnaphthalene sulfonates with corrosion inhibiting properties |
-
1992
- 1992-02-27 DE DE4206047A patent/DE4206047A1/en not_active Withdrawn
-
1993
- 1993-02-15 AT AT93102317T patent/ATE151449T1/en not_active IP Right Cessation
- 1993-02-15 EP EP93102317A patent/EP0557839B1/en not_active Expired - Lifetime
- 1993-02-15 DE DE59306079T patent/DE59306079D1/en not_active Expired - Lifetime
- 1993-02-15 ES ES93102317T patent/ES2099852T3/en not_active Expired - Lifetime
- 1993-02-15 DK DK93102317.0T patent/DK0557839T3/en active
- 1993-02-25 JP JP5061010A patent/JPH0625687A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2763615A (en) * | 1953-04-16 | 1956-09-18 | Monsanto Chemicals | Carboxylic acid derivatives and lubricants containing them |
| US3096357A (en) * | 1960-05-04 | 1963-07-02 | Bohme Fettchemie Gmbh | Novel reaction products of a sulfuric acid and epoxides |
| FR1570355A (en) * | 1967-06-30 | 1969-06-06 | ||
| EP0247467A2 (en) * | 1986-05-24 | 1987-12-02 | Henkel Kommanditgesellschaft auf Aktien | Use of salts from esters of long chain fatty alcohols with alpha-sulfofatty acids |
| EP0335429A2 (en) * | 1988-03-22 | 1989-10-04 | King Industries, Inc. | Amine dinonylnaphthalene sulfonates with corrosion inhibiting properties |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4079830A1 (en) | 2021-04-19 | 2022-10-26 | Marteen Sports World, S.L. | Biodegradable lubricant composition |
Also Published As
| Publication number | Publication date |
|---|---|
| DK0557839T3 (en) | 1997-10-13 |
| EP0557839B1 (en) | 1997-04-09 |
| JPH0625687A (en) | 1994-02-01 |
| ES2099852T3 (en) | 1997-06-01 |
| DE4206047A1 (en) | 1993-09-02 |
| DE59306079D1 (en) | 1997-05-15 |
| ATE151449T1 (en) | 1997-04-15 |
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