DE717968C - Additive to lubricants - Google Patents

Additive to lubricants

Info

Publication number
DE717968C
DE717968C DEN40959D DEN0040959D DE717968C DE 717968 C DE717968 C DE 717968C DE N40959 D DEN40959 D DE N40959D DE N0040959 D DEN0040959 D DE N0040959D DE 717968 C DE717968 C DE 717968C
Authority
DE
Germany
Prior art keywords
lubricants
additive
alkenes
condensing
polycarboxylic acids
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
Application number
DEN40959D
Other languages
German (de)
Inventor
Franz Rudolf Moser
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bataafsche Petroleum Maatschappij NV
Original Assignee
Bataafsche Petroleum Maatschappij NV
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bataafsche Petroleum Maatschappij NV filed Critical Bataafsche Petroleum Maatschappij NV
Application granted granted Critical
Publication of DE717968C publication Critical patent/DE717968C/en
Expired legal-status Critical Current

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
    • 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
    • C10M129/26—Carboxylic acids; Salts thereof
    • C10M129/28—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M129/38—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms
    • C10M129/42—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms polycarboxylic
    • 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
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
    • 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
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
    • 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
    • C10M2207/22—Acids obtained from polymerised unsaturated 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/086—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type polycarboxylic, e.g. maleic acid
    • 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
    • C10N2040/02—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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy

Description

Es ist schon vorgeschlagen worden, Schmiermittel, -wie mineralische Schmieröle u.a., durch Zusatz geringer Mengen von Dicarbonsäuren zu verbessern, welche durch Kondensation von Alkenen oder Albengemischen mit Maleinsäureanhydrid und nachfolgendes Verseifen dies *' Kondensationsproduktes erhalten worden sind* Die Dicarbonsäuren haben die Eigenschaft, die Schmierfähigkeit der Schmiermittel zu verbessern. In verschiedenen Fällen ergab sich jedoch, daß: diese Säuren den Nachteil einer korrodierenden Einwirkung auf die Lagermetalle haben. Wenn man so z. B. Schmiermittel, welche einen Zusatz der genannten Säuren enthalten, in Bleibronzelagern verwendet, kann ein grüner Überzug auf dem Metall auftreten.It has already been proposed to improve lubricants, such as mineral lubricating oils, among other things, by adding small amounts of dicarboxylic acids, which have been obtained by condensation of alkenes or mixtures of alkenes with maleic anhydride and subsequent saponification of this * 'condensation product * The dicarboxylic acids have the property that Improve the lubricity of the lubricant. In various cases, however, it was found that : These acids have the disadvantage of corrosive action on the bearing metals. If you z. B. lubricants that contain an additive of the acids mentioned, used in lead bronze bearings, a green coating may appear on the metal.

Es ist nun gefunden worden, daß kein grüner Überzug oder andere Korrosionserscheinungen auftreten, wenn man Polycarbonsäuren zusetzt, die erhalten worden sind durch Kondensieren von Alkenen oder Alkengemischen, die etwa über 250°, vorzugsweise über etwa 300°, sieden, mit Maleinsäureanhydrid und nachfolgendes Verseifen mit Wasser durch Erhitzen des erhaltenen Kondensationsproduktes. Die gleichen Erzeugnisse können auch erhalten werden durch Kondensieren der gleichen Alkene oder Alkengeimische mit freier Maleinsäure. Etwa im Kondensationsprodukt vorhandene Verunreinigungen können vor der Umsetzung in Polycarbonsäuren in einfacher Weise beseitigt werden, indem man das Kondensationsprodukt nach Entfernung von gegebenenfalls nicht umgesetzten Reaktionskomponenten mit etwa der gleichen Menge Wasser beiIt has now been found that there is no green coating or other signs of corrosion occur when adding polycarboxylic acids obtained by condensing alkenes or Alkene mixtures which boil over about 250 °, preferably over about 300 °, with maleic anhydride and subsequent saponification with water by heating the obtained Condensation product. The same products can also be obtained by condensing the same alkenes or alkene mixtures with free maleic acid. Any existing in the condensation product Impurities can be removed in a simple manner before they are converted into polycarboxylic acids by removing the condensation product after removal of any unreacted reaction components with about the same amount of water

So bis ioo° unter Rühren vermischt und dann absitzen läßt, worauf die hierbei gebildete anhydridhaltige Schicht von der anderen, die Verunreinigungen enthaltenden, Schicht abgetrennt wii'd. Nach der Umsetzung in Polycarbonsäuren lassen die Verunreinigungen sich meistens nicht _ leicht beseitigen, da dann beim Auswaschen öfters schwer trennbare Emulsionen entstehen. ίο Die besondere Eignung der Erzeugnisse als Zusatz zu Schmiermitteln war von vornherein nicht zu erwarten, weil bei den erfindungsgemäß verwendeten Säuren die Carboxylgruppen sehr nahe benachbart sind, so daß mit einer geringeren Acidität im Vergleich zu den früher benutzten Verbindungen im Hinblick auf die Tatsache, daß bei wachsendem Abstand der Carboxylgruppen die Dissoziationskonstante häufig abnimmt, nicht gerechnet werden konnte. Der Verwendung der besonderen hochmolekularen Produkte standen auch insofern Bedenken entgegen, als eine unzureichende Löslichkeit im Öl zu befürchten war.So mixed up to 100 ° with stirring and then lets settle, whereupon the anhydride-containing layer formed by the other, the layer containing impurities was separated off. After implementation In polycarboxylic acids, the impurities are usually not easy to remove, because emulsions that are difficult to separate often arise during washing. ίο The particular suitability of the products as an additive to lubricants was not to be expected from the outset, because with the according to the invention acids used the carboxyl groups are very closely adjacent, so that with a lower acidity in comparison to the previously used compounds in view of the fact that with increasing distance between the carboxyl groups the dissociation constant often decreases, could not be calculated. Of use The special high molecular weight products were also objected to insofar as insufficient solubility was to be feared in the oil.

Außerdem ist gefunden worden, daß solche Säuren, die unter Verwendung hochmolekularer Alkene hergestellt worden sind, bei der Prüfung auf dem Vierkugelapparat (vgl. Engineering., vom . 14. Juli 1933) eine höhere Zerreißtemperatur (das ist die Temperatur, bei welcher der Ölfilm auf den Kugeln unterbrochen wird und die durch elektrischein Kontakt bestimmt werden kann) aufweisen als die aus den niedriger molekularen Alkenen erhaltenen Erzeugnisse. Außerdem weisen sie im Vergleich zu den letztgenannten Säuren in dem ganzen Temperaturgebiet bis zu der Zerreißtemperatur einen niedrigeren Reibungskoeffizienten auf.In addition, it has been found that such acids, using high molecular weight Alkenes have been produced when testing on the four-ball apparatus (see Engineering., from the . July 14, 1933) a higher rupture temperature (that is the temperature in which the oil film on the balls is interrupted and through electrical contact can be determined) than the products obtained from the lower molecular weight alkenes. They also show in comparison to the latter acids in the whole temperature range up to At rupture temperature, a lower coefficient of friction.

Weiterhin haben die Polycarbonsäuren gemäß vorliegender Erfindung eine stärkere Schutzwirkung hinsichtlich der korrodierenden Einflüsse bei gewöhnlicher Temperatur (kalte Korrosion), was von besonderer Bedeutung ist für Zylinder von Maschinen, wie Flugmotoren, welche außer Betrieb gesetzt sind.Furthermore, the polycarboxylic acids according to the present invention have a stronger one Protective effect with regard to the corrosive influences at ordinary temperature (cold corrosion), which is of particular importance for cylinders of machines, like aircraft engines that are out of order.

Die Alkene oder Alkengemische können • durch sorgfältiges Spalten oder Dehydrieren hochsiedender Kohlenwasserstoffe oder Mischungen solcher, wie Paraffin, erhalten werden. The alkenes or alkene mixtures can • by careful cleavage or dehydration high-boiling hydrocarbons or mixtures thereof, such as paraffin, can be obtained.

In der Regel sind die Mengen an zugesetzten Polycarbonsäuren verhältnismäßig gering, z.B. unter 50/0, in manchen Fällen sogar unter i°/o·As a rule, the amounts of polycarboxylic acids added are relatively small, e.g. below 50/0, in some cases even below i ° / o

Beispielexample

300 Gewichtsteile einer durch Dampfphasenspaltung aus festem Paraffin erhalte-η en Fraktion, welche zwischen 280 und 340' siedet und eine Broimzahl 36 aufweist, werden in einem Autoklaven mit 33 Gewichtsteilen Maleinsäureanhydrid 2 Stunden lang bei 220° erhitzt. Der nicht umgesetzte Teil der Spaltfraktion sowie Spuren nicht umgesetzten Malemsäureanhydrids werden durch Vakuumdestillation unter 2000 von dem Produkt abgetrennt. Man erhält ein Erzeugnis mit der Verseifungszahl 345 in einer Ausbeute von 97 Gewichtsteilen, welches aus Anhydriden der gebildeten Polycarbonsäuren besteht, die durch Erhitzen mit einer der Verseifungszahl entsprechenden Menge Wasser während 1 Stunde bei 90° in die freien Polycarbonsäuren übergeführt werden. Die Überführung in Polycarbonsäuren kann auch bei einer Temperatur von z.B. 150 bis i6o° in Gegenwart von Wasserdampf (z. B. durch Überleiten) durchgeführt werden. Dieses Erzeugnis verhindert beim Zusetzen zu einem Schmieröl in einer Menge von 14°/o den korrodierenden Angriff auf Bleibronzelager im Gegensatz zu einem in ähnlicher Weise aus der zwischen 160 und 2000 siedenden Fraktion des gleichen Spaltproduktes erhaltenen Säuregemisch, während sich außerdem bei einer Prüfung im Vierkugelapparat zeigt, daß die Zerreißtemperatur etwa um 500 höher liegt als bei Verwendung der aus der Fraktion 160 bis 200 hergestellten Säuren.300 parts by weight of a fraction obtained by vapor phase splitting from solid paraffin, which boils between 280 and 340 'and has a Broim number 36, are heated in an autoclave with 33 parts by weight of maleic anhydride for 2 hours at 220 °. The unreacted portion of the gap fraction as well as traces of unreacted Malemsäureanhydrids be separated by vacuum distillation to 200 0 of the product. A product with the saponification number 345 is obtained in a yield of 97 parts by weight, which consists of anhydrides of the polycarboxylic acids formed, which are converted into the free polycarboxylic acids by heating with an amount of water corresponding to the saponification number for 1 hour at 90 °. The conversion into polycarboxylic acids can also be carried out at a temperature of, for example, 150 to 160 ° in the presence of steam (for example, by passing over). This product prevented in addition to a lubricating oil in an amount of 14 ° / o the corrosive attack on lead bronze bearing, in contrast to a similarly derived from between 160 and 200 0-boiling fraction of the same cleavage product mixture of acids, while also in at a test four-ball apparatus, showing that the Zerreißtemperatur about 0 is 50 higher than when using the acids prepared from the fraction from 160 to 200.

Claims (2)

Patentansprüche:Patent claims: 1. Die Verwendung hochmolekularer Polycarbonsäuren, die erhalten worden sind durch Kondensieren solcher Alkene oder Alkengemische, welche über 250°, vorzugsweise über 3000, sieden, mit freier Maleinsäure oder durch Kondensieren der gleichen Alkene oder Alkengemische mit Maleinsäureanhydrid und nachfolgendes Verseifen mit Wasser durch Erhitzen der erhaltenen Kondensationsprodukte, als Zusatz zu Schmiermitteln.1. The use of high molecular weight polycarboxylic acids, which have been obtained by condensing such alkenes or Alkengemische which more than 250 °, preferably more than 300 0, boil, with free maleic acid or by condensing the same alkenes or Alkengemische with maleic anhydride and subsequent hydrolysis with water by heating of the condensation products obtained, as an additive to lubricants. 2. Verwendung solcher Polycarbonsäuren nach Anspruch 1, die erhalten worden sind durch Kondensieren von Maleinsäureanhydrid mit zwischen 250 und 350° siedenden Spaltprodukten von Paraffin und nachfolgendes Verseifen des Kon- no densationsproduktes, als Zusatz zu Schmiermitteln. 2. Use of such polycarboxylic acids according to claim 1 which have been obtained are by condensing maleic anhydride at between 250 and 350 ° boiling decomposition products of paraffin and subsequent saponification of the condensation product, as an additive to lubricants. BERLIN. GEDRUCKT IN DEIlBERLIN. PRINTED IN DEIL
DEN40959D 1936-07-24 1937-07-14 Additive to lubricants Expired DE717968C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL488597X 1936-07-24

Publications (1)

Publication Number Publication Date
DE717968C true DE717968C (en) 1942-02-27

Family

ID=19786660

Family Applications (1)

Application Number Title Priority Date Filing Date
DEN40959D Expired DE717968C (en) 1936-07-24 1937-07-14 Additive to lubricants

Country Status (5)

Country Link
US (1) US2133734A (en)
DE (1) DE717968C (en)
FR (1) FR824613A (en)
GB (1) GB488597A (en)
NL (1) NL45837C (en)

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* Cited by examiner, † Cited by third party
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US2542542A (en) * 1948-08-02 1951-02-20 Standard Oil Dev Co Lubricating oil additives
US2647872A (en) * 1950-01-27 1953-08-04 Shell Dev Grease composition
US2824859A (en) * 1953-03-18 1958-02-25 Exxon Research Engineering Co Production of resins by reaction of maleic anhydride with steam-cracked fractions
US2805994A (en) * 1954-12-27 1957-09-10 Standard Oil Co Lubricant grease compostion containing surface esterified organic siliceous organophilic solid thickener
US2806860A (en) * 1955-07-20 1957-09-17 Union Carbide Corp Epoxyalkyl succinic anhydrides
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US2971915A (en) * 1957-02-11 1961-02-14 Shell Oil Co Lubricating oil compositions
NL240511A (en) * 1958-06-25
US3004923A (en) * 1958-12-15 1961-10-17 Nalco Chemical Co Process and compositions for inhibiting and preventing the foaming of aqueous systems
US3048542A (en) * 1959-01-30 1962-08-07 Texaco Inc Lubricating compositions
US3288714A (en) * 1961-12-06 1966-11-29 Monsanto Co Lubricating oil compositions containing alkenyl succinic anhydrides
DE1250951B (en) * 1962-11-30 1967-09-28 Esso Research and Engineering Company Elizabeth, NJ (V St A) Morway, Clark, N J, James Nixon, Elizabeth N J, Rudolph Kassmger, Westfield, N J (V St. A) I Lubricants
US3382172A (en) * 1966-05-18 1968-05-07 Chevron Res Alkenyl succinic acids as antiwear agents
US3671433A (en) * 1970-12-17 1972-06-20 Dow Corning Lubricant compositions
US4321308A (en) * 1975-02-07 1982-03-23 The Lubrizol Corporation Metal workpieces coated with ester-based hot melt metal working lubricants
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US8334244B2 (en) 2005-01-18 2012-12-18 Bestline International Research, Inc. Universal synthetic water displacement multi-purpose penetrating lubricant, method and product-by-process
US8062388B2 (en) 2005-01-18 2011-11-22 Bestline International Research, Inc. Universal synthetic lubricant, method and product-by-process to replace the lost sulfur lubrication when using low-sulfur diesel fuels
US7745382B2 (en) 2005-01-18 2010-06-29 Bestline International Research Inc. Synthetic lubricant additive with micro lubrication technology to be used with a broad range of synthetic or miner host lubricants from automotive, trucking, marine, heavy industry to turbines including, gas, jet and steam
US20150247103A1 (en) 2015-01-29 2015-09-03 Bestline International Research, Inc. Motor Oil Blend and Method for Reducing Wear on Steel and Eliminating ZDDP in Motor Oils by Modifying the Plastic Response of Steel
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Also Published As

Publication number Publication date
US2133734A (en) 1938-10-18
FR824613A (en) 1938-02-11
NL45837C (en)
GB488597A (en) 1938-07-11

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