DE1156926B - Lubricating oils - Google Patents
Lubricating oilsInfo
- Publication number
- DE1156926B DE1156926B DEC22117A DEC0022117A DE1156926B DE 1156926 B DE1156926 B DE 1156926B DE C22117 A DEC22117 A DE C22117A DE C0022117 A DEC0022117 A DE C0022117A DE 1156926 B DE1156926 B DE 1156926B
- Authority
- DE
- Germany
- Prior art keywords
- monoalkenyl
- dialkylaminoalkyl
- succinimide
- carbon atoms
- lubricating oil
- 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.)
- Pending
Links
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
- C07D207/408—Radicals containing only hydrogen and carbon atoms attached to ring carbon atoms
- C07D207/412—Acyclic radicals containing more than six carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/567—Preparation of carboxylic acid anhydrides by reactions not involving carboxylic acid anhydride groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
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- 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
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
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- C—CHEMISTRY; METALLURGY
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- 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
- C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
- C10M133/56—Amides; Imides
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/02—Well-defined aliphatic compounds
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/02—Well-defined aliphatic compounds
- C10M2203/022—Well-defined aliphatic compounds saturated
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- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/02—Well-defined aliphatic compounds
- C10M2203/024—Well-defined aliphatic compounds unsaturated
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- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/04—Well-defined cycloaliphatic compounds
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- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/06—Well-defined aromatic compounds
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- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
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- C10M2203/102—Aliphatic fractions
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- C10M2203/104—Aromatic fractions
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- C10M2203/106—Naphthenic fractions
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- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/108—Residual fractions, e.g. bright stocks
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- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/024—Propene
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- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/026—Butene
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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Description
Gegenstand der Erfindung sind Schmieröle, die als Reinigungsmittel N-Dialkylaminoalkyl-monoalkenylsuccinimide enthalten.The invention relates to lubricating oils which, as cleaning agents, contain N-dialkylaminoalkyl-monoalkenylsuccinimides contain.
Alkenyl-bernsteinsäureanhydride sowie zahlreiche ihrer Derivate sind in der Technik bekannt. So gelten z. B. Alkenyl-bernsteinsäureanhydride, deren Alkenylrest 5 bis 20 Kohlenstoffatome enthält, in Schmiergemischen als Antikorrosionsmittel, und Produkte aus der Umsetzung derartiger Alkenyl-bernsteinanhydride mit Monoaminen werden in Schmierölgemischen als Antikorrosionsmittel für Eisen, verwendet. Alkenyl succinic anhydrides as well as many of their derivatives are known in the art. So apply z. B. Alkenyl succinic anhydrides, the alkenyl radical of which contains 5 to 20 carbon atoms, in lubricating mixtures as anti-corrosion agents, and products from the reaction of such alkenyl amber anhydrides with monoamines are used in lubricating oil mixtures as anti-corrosion agents for iron.
Obige bekannte Alkenyl-succinimide sind jedoch als Reinigungsmittel für Schmierölgemische nicht geeignet. Hingegen erweisen sich die erfindungsgemäßen Alkenyl-succinimide für diesen Zweck als gute Reinigungsmittel.However, the above known alkenyl succinimides are not suitable as cleaning agents for lubricating oil mixtures suitable. In contrast, the alkenyl succinimides according to the invention prove to be suitable for this purpose good detergent.
Es sind Motortreibstoffe bekannt, die als Oxydationsinhibitor das Reaktionsprodukt aus einer Monocarbonsäure und einem Polyalkylenimin enthalten. There are motor fuels known as the oxidation inhibitor, the reaction product of a Contain monocarboxylic acid and a polyalkyleneimine.
Die heutigen Verbrennungsmotoren laufen mit hoher Geschwindigkeit und hoher Verdichtungszahl. Bei dem ständigen Halten und Anfahren im heutigen Stadtverkehr, dem sehr viele Kraftfahrzeuge während des größten Teil der Fahrzeit ausgesetzt sind, erreichen die Verbrennungsmotoren jedoch nicht die wirksamste Arbeitstemperatur. Unter den im Stadtverkehr herrschenden Bedingungen bilden sich große Mengen von als einzelne Teilchen vorliegenden Oxydationsprodukten, die, da sie über die Kolbenringe hinausgeblasen werden, das Kurbelgehäuse des Motors erreichen. Der größte Teil dieser als einzelne Teilchen vorliegenden Oxydationsprodukte ist in Öl unlöslich und neigt dazu, auf den verschiedenen Teilen des Motors, wie dem Kolben, Kolbenringen usw., Ablagerungen zu bilden. Zur Verhinderung derartiger Ablagerungen müssen den Schmierölgemischen Reinigungsmittel zugesetzt werden, um die polymeren Produkte in stark dispergiertem Zustand zu halten.Today's internal combustion engines run at high speed and high compression ratios. With the constant stopping and starting in today's city traffic, which many motor vehicles during are exposed to most of the driving time, the internal combustion engines do not achieve the most effective working temperature. Large ones form under the conditions prevailing in city traffic Amounts of oxidation products present as individual particles which, as they pass over the piston rings blown out can reach the crankcase of the engine. Most of these as individual particles The oxidation products present is insoluble in oil and tends to be on different parts of the oil Engine, such as the piston, piston rings, etc., to form deposits. To prevent such Deposits must be added to the lubricating oil mixtures in order to keep the polymeric detergents To keep products in a highly dispersed state.
Meistens bestehen die verschiedenen Reinigungsmittel, die dem in das Kurbelgehäuse gelangenden ölen zugesetzt werden, um die Bildung von Schlämmen und Firnissen zu verringern, aus metallorganischen Verbindungen, insbesondere aus solchen Verbindungen, in denen das Metall über ein Sauerstoffatom an eine organische Gruppe gebunden ist. Obgleich diese metallhaltigen organischen Verbindungen als Reinigungsmittel eine gewisse Wirksamkeit besitzen und die Vorstufen der Ablagerungen in dem Öl selbst dispergieren, damit sich letztere nicht auf den verschiedenen Teilen des Motors ablagern können, SchmieröleMost often there are the various cleaning agents that make up the one that gets into the crankcase oils can be added to reduce the formation of sludges and varnishes, from organometallic Compounds, especially from those compounds in which the metal has an oxygen atom an organic group is attached. Although these metal-containing organic compounds are used as cleaning agents have a certain effectiveness and the precursors of the deposits in the oil itself disperse so that the latter cannot be deposited on the different parts of the engine, Lubricating oils
Anmelder:Applicant:
California Research Corporation,
San Francisco, Calif. (V. St. A.)California Research Corporation,
San Francisco, Calif. (V. St. A.)
Vertreter: Dr. W. Beil, A. HoeppenerRepresentative: Dr. W. Beil, A. Hoeppener
und Dr. H. J. Wolff, Rechtsanwälte,
Frankfurt/M.-Höchst, Antoniterstr. 36and Dr. HJ Wolff, lawyers,
Frankfurt / M.-Höchst, Antoniterstr. 36
Beanspruchte Priorität:Claimed priority:
V. St. v. Amerika vom 24. August 1959V. St. v. America August 24, 1959
(Nr. 835 390 und Nr. 835 400)(No. 835 390 and No. 835 400)
Frank Albert Stuart, Orinda, Calif.,Frank Albert Stuart, Orinda, Calif.,
Robert Gordon Anderson, Novato, Calif.,Robert Gordon Anderson, Novato, Calif.,
und Alan YuIe Dr^mmond, Richmond, Calif.and Alan YuIe Dr ^ mmond, Richmond, Calif.
(V. St. Α.),
sind als Erfinder genannt worden(V. St. Α.),
have been named as inventors
haben sie den Nachteil, daß sie im Motor Ascheablagerungen bilden, die Zündkerzen und Ventile verschmutzen, dadurch die Leistung des Motors herabmindern und eine Frühzündung mitverursachen. they have the disadvantage that they form ash deposits in the engine, the spark plugs and Clog the valves, thereby reducing engine performance and contributing to pre-ignition.
Ziel der Erfindung sind daher Schmieröle, die metallfreie Reinigungsmittel enthalten.
Es wurde gefunden, daß man für den Schwerbetrieb besonders geeignete Schmierölgemische dadurch erhält,
daß man Ölen mit Schmierölviskosität 0,25 bis 5,0 Gewichtsprozent, bezogen auf das Gesamtschmieröl,
bestimmter N-Dialkylaminoalkyl-monoalkenyl-succinimide
zusetzt.The aim of the invention is therefore lubricating oils which contain metal-free cleaning agents.
It has been found that lubricating oil mixtures which are particularly suitable for heavy duty operation are obtained by adding certain N-dialkylaminoalkylmonoalkenyl succinimides to oils with a lubricating oil viscosity of 0.25 to 5.0 percent by weight, based on the total lubricating oil.
Die N-Dialkylaminoalkyl-monoalkenyl-succinimide sind in Schmierölgemischen besonders wirksame Reinigungsmittel. Bei Verwendung von Schmierölgemischen, die diese Alkenyl-succinimide enthalten, bleiben die verschiedenen Teile von Diesel- und Benzinmotoren sogar unter harten Arbeitsbedingungen bis zu einem erstaunlichen Grade frei von Ablagerungen und Firnissen.The N-dialkylaminoalkyl-monoalkenyl-succinimides are particularly effective cleaning agents in lubricating oil mixtures. When using lubricating oil mixtures, The various parts of diesel and fuel that contain these alkenyl succinimides remain Petrol engines are remarkably free of debris, even under tough working conditions and varnishes.
309 747/350309 747/350
Die erfindungsgemäß eingesetzten N-Dialkylaminoalkyl-monoalkenyl-succinimide können durch, folgende Formel wiedergegeben werden:The N-dialkylaminoalkyl-monoalkenyl-succinimides used according to the invention can be represented by the following formula:
R-CH-CR-CH-C
N — R1 —N - R 1 -
CH2-CCH 2 -C
,R2
1R3 , R 2
1 R 3
in der R einen Alkenylrest mit 30 bis 200 Kohlenstoffatomen, R1 einen zweiwertigen Alkylenrest und R2 und R3 Alkylreste bedeuten. Die Summe der Kohlenstoffatome in R1, R2 und R3 beträgt 3 bis 10.in which R is an alkenyl radical having 30 to 200 carbon atoms, R 1 is a divalent alkylene radical and R 2 and R 3 are alkyl radicals. The sum of the carbon atoms in R 1 , R 2 and R 3 is 3 to 10.
R besteht vorzugsweise aus einem Polymeren eines Olefins mit 2 bis 5 Kohlenstoffatomen, wobei das Molekulargewicht des Polymeren zwischen 400 und 3000, vorzugsweise zwischen etwa 900 und etwa 1200 liegt. Beispiele solcher Olefine sind Äthylen, Propylen, 1-Buten, 2-Buten, Isobuten sowie deren Gemische. Da das im einzelnen angewendete Verfahren zur Polymerisation der Olefine für die Herstellung der neuen, vorliegend beschriebenen Verbindung unwesentlich ist, kann hierfür jedes der zahlreichen zur Verfügung stehenden Verfahren angewendet werden.R preferably consists of a polymer of an olefin having 2 to 5 carbon atoms, the Molecular weight of the polymer between 400 and 3000, preferably between about 900 and about 1200 lies. Examples of such olefins are ethylene, propylene, 1-butene, 2-butene, isobutene and their Mixtures. Since the process used in detail for the polymerization of olefins for the production of new, presently described compound is insignificant, any of the numerous available procedures are used.
Als Alkylenrest kann für R1 ein zweiwertiger Äthylenrest, Propylenrest, Butylenrest usw. verwendet werden. Alkylreste der Symbole R2 und R3 sind Methyl, Äthyl, Propyl usw. Vorzugsweise enthält R1 3 Kohlenstoffatome und R2 und R3 jeweils 1 Kohlenstoffatom.A divalent ethylene radical, propylene radical, butylene radical, etc. can be used as the alkylene radical for R 1. Alkyl radicals of the symbols R 2 and R 3 are methyl, ethyl, propyl, etc. Preferably, R 1 contains 3 carbon atoms and R 2 and R 3 each contain 1 carbon atom.
Amin- Reaktionsteilnehmer für die Herstellung von N-Dialkylaminoalkyl-monoalkenyl-succinimiden sind z. B.: Dimethylaminomethylamin, Dimethylaminoäthylamin, Dimethylaminopropylamin, Dimethylaminobutylamin, Dimethylaminoheptylamin, Diäthylaminomethylamin, Diäthylaminopropylamin, Diäthylaminoamylamin, Dipropylaminopropylamin, Methylpropylaminoamylamin und Propylbutylaminoäthylamin. Amine reactants for the preparation of N-dialkylaminoalkyl monoalkenyl succinimides are z. E.g .: dimethylaminomethylamine, dimethylaminoethylamine, dimethylaminopropylamine, dimethylaminobutylamine, Dimethylaminoheptylamine, diethylaminomethylamine, diethylaminopropylamine, diethylaminoamylamine, dipropylaminopropylamine, Methylpropylaminoamylamine and propylbutylaminoethylamine.
Das Verfahren zur Herstellung der Succinimide, für das im Rahmen vorliegender Erfindung kein Schutz begehrt wird, kann wie folgt durchgeführt werden:The process for the preparation of the succinimides, for which within the scope of the present invention no Protection is desired can be carried out as follows:
Ein Polyolefin wird mit Maleinsäureanhydrid unter Bildung eines Monoalkenylsuccinsäureanhydrids umgesetzt, das weiter mit einem Diäthylaminoalkylamin in etwa äquimolaren Mengen zur Reaktion gebracht wird und dabei das gewünschte N-Dialkylaminoalkyl-monoalkenyl-succinimid bildet.A polyolefin is reacted with maleic anhydride to form a monoalkenyl succinic anhydride, further reacted with a diethylaminoalkylamine in approximately equimolar amounts and thereby the desired N-dialkylaminoalkyl-monoalkenyl-succinimide forms.
Da die Umsetzung des Polyolefins mit dem Maleinsäureanhydrid nicht immer bis zur Vollständigkeit fortschreiten wird, kann das erhaltene Alkenylbernsteinsäureanhydrid etwas nicht umgesetztes Polyolefin enthalten. Da eine Abtrennung dieses nicht umgesetzten Polyolefins in diesem Stadium unzweckmäßig sein kann, wird das erhaltene Imid aus der Umsetzung des Alkenyl-bernsteinsäureanhydrids mit dem Diamin als Verunreinigung dieses Polyolefin enthalten, das bei der Herstellung von Schmierölgemischen ein Verdünnungsmittel sein kann. Gewünschtenfalls kann jedoch dieses nicht umgesetzte Polyolefin ζ. B. durch Aceton oder Methanol aus einer Kohlenwasserstofflösung ausgefällt und entfernt werden.Because the reaction of the polyolefin with the maleic anhydride will not always progress to completion, the obtained alkenyl succinic anhydride may contain some unreacted polyolefin. Since separation of this unreacted polyolefin is inconvenient at this stage can be, the imide obtained from the reaction of the alkenyl succinic anhydride with Contain diamine as an impurity in this polyolefin, which is used in the manufacture of lubricating oil blends can be a diluent. If desired, however, this can not be implemented Polyolefin ζ. B. precipitated by acetone or methanol from a hydrocarbon solution and removed will.
In nachstehenden Beispielen wird die Herstellung von N-Dialkylaminoalkyl-monoalkenyl-succinimiden beschrieben.The following examples illustrate the preparation of N-dialkylaminoalkyl-monoalkenyl-succinimides described.
Beispiel 1
Herstellung von Polybutenyl-bernsteinsäureanhydridexample 1
Production of polybutenyl succinic anhydride
Unter einer Stickstoffatmosphäre wird ein Gemisch aus 1000 g (1 Mol) Polybuten mit einem Molekulargewicht von etwa 1000 und 98 g (1 Mol) Maleinsäureanhydrid unter Rühren 24 Stunden auf 210° C erhitzt. Dann wird das Reaktionsgemisch auf 66° C abgekühlt, und man gibt 700 cm3 Hexan hinzu. Nach Entfernung des Hexans aus dem Filtrat durch Vakuumdestillation wird das Produkt 1 Stunde auf 177° C bei einen! absoluten Druck von 10 mm Hg gehalten, um Spuren von Maleinsäureanhydrid zu entfernen. Die Verseifungszahl des auf diese Weise hergestellten rohen Polybutenyl-bernsteinsäureanhydrids betrug 79.Under a nitrogen atmosphere, a mixture of 1000 g (1 mol) of polybutene with a molecular weight of about 1000 and 98 g (1 mol) of maleic anhydride is heated to 210 ° C. for 24 hours with stirring. The reaction mixture is then cooled to 66 ° C. and 700 cm 3 of hexane are added. After the hexane has been removed from the filtrate by vacuum distillation, the product is heated to 177 ° C. for 1 hour at a! Maintained absolute pressure of 10 mm Hg to remove traces of maleic anhydride. The saponification value of the crude polybutenyl succinic anhydride thus prepared was 79.
Herstellung von N-Dimethylaminopropylmono-(polybutenyl)-succinimid Production of N-dimethylaminopropylmono- (polybutenyl) succinimide
Unter einer Stickstoffatmosphäre wurden 21,3 g (0,21 Mol) Dimethylaminopropylamin und 150 g (0,09 Mol) Polybutenyl-bernsteinsäureanhydrid des Beispiels 1 unter Rühren vermischt und das Gemisch 1 Stunde auf 260° C erhitzt. Dann wurde der absolute Druck unter Beibehaltung dieser Temperatur während 30 Minuten auf etwa 200 mm Hg verringert, um die Entfernung von Wasser und überschüssigem Amin zu erleichtern. Unter Beibehaltung dieses verringerten Druckes ließ man das Reaktionsgemisch dann auf Raumtemperatur abkühlen. Das Produkt enthielt 1,7 7o Stickstoff (theoretische Menge = 1,8%). Die Identität des N-Dimethylaminopropylalkenyl-succinimids wurde durch Infrarot-Spektroskopie nachgewiesen. Under a nitrogen atmosphere, there were obtained 21.3 g (0.21 mol) of dimethylaminopropylamine and 150 g (0.09 mol) polybutenyl succinic anhydride of Example 1 mixed with stirring and the mixture Heated to 260 ° C for 1 hour. Then the absolute pressure was maintained while maintaining this temperature Reduced to about 200 mm Hg for 30 minutes to remove water and excess amine to facilitate. The reaction mixture was then released while maintaining this reduced pressure Cool down to room temperature. The product contained 1.7 70 nitrogen (theoretical amount = 1.8%). the Identity of the N-dimethylaminopropylalkenyl succinimide was detected by infrared spectroscopy.
Nachstehende Tabelle 1 enthält weitere Daten für die Herstellung von N-Dialkylaminoalkyl-monoalkenyl-succinimiden. Als Polyamin wurde Dimethylpropylamin verwendet, und der Alkenylrest des Alkenyl-succinimids bestand aus einem Polybuten dessen Molekulargewicht in Tabelle I aufgeführt istTable 1 below contains further data for the preparation of N-dialkylaminoalkyl-monoalkenyl-succinimides. Dimethylpropylamine was used as the polyamine, and the alkenyl radical of the alkenyl succinimide consisted of a polybutene whose molecular weight is listed in Table I.
Molekulargewicht
des PolyisobuteneMolecular weight
of polyisobutenes
Menge der Reaktionsteilnehmer (g)
PIBBA* I AminAmount of reactants (g)
PIBBA * I amine
Reaktionstemperatur
(0QReaction temperature
( 0 Q
Prozentualer StickstoffgehaltPercentage of nitrogen
gefundenfound
theoretischtheoretically
etwa 350
etwa 700about 350
about 700
334
500334
500
21,3
44,021.3
44.0
260
168260
168
4,1
1,84.1
1.8
4,0
1,44.0
1.4
*) Polyisobutenyl-bernsteinsäureanhydrid.*) Polyisobutenyl succinic anhydride.
Als Basisöle für Schmierölgemische solcher Alkenylsuccinimide kann eine Vielzahl von Schmierölen eingesetzt werden. Hierzu gehören Schmieröle auf naphthenischer Basis, Paraffinbasis und Mischbasis, andere Kohlenwasserstoff-Schmiermittel, z. B. Schmieröle aus Kohleprodukten, und synthetische öle, z. B. Alkylenpolymere (wie Polymere von Propylen, Butylen usw. sowie deren Gemische), Polymere der Alkylenoxydart (z. B. Alkylenoxydpolymere aus der in Gegenwart von Wasser oder Alkoholen, z. B. Äthylenalkohol, durchgeführten Polymerisation von Alkylenoxyd, z. B. Propylenoxyd usw.), Dicarbonsäureester (z. B. Ester von Dicarbonsäuren, wie Adipinsäure, Azelainsäure, Korksäure, Sebacinsäure, Alkanolbernsteinsäure, Fumarsäure, Maleinsäure, mit Alkoholen, wie Butylalkohol, Hexylalkohol, 2-Äthylhexylalkohol, Dodecylalkohol), flüssige Ester von Phosphorsäuren, Alkylbenzole, Polyphenyle (z. B. Biphenyle und Terphenyle), Alkyldiphenyläther, Siliconpolymere (z. B. Tetraäthylsilicat, Tetraisopropylsilicate, Tetra-(4-methyl-2-tetraäthyl)-silicat, Hexyl-(4-methyl-2-pentoxy)-disiloxan, Poly-(methyl)-siloxan und Poly-(methylphenyl)-siloxan).As base oils for lubricating oil mixtures of such alkenyl succinimides a wide variety of lubricating oils can be used. This includes lubricating oils naphthenic base, paraffin base and mixed base, other hydrocarbon lubricants, e.g. B. Lubricating Oils from coal products, and synthetic oils, e.g. B. Alkylene polymers (such as polymers of propylene, butylene etc. and their mixtures), polymers of the alkylene oxide type (e.g. alkylene oxide polymers from the in Presence of water or alcohols, e.g. B. Ethylene alcohol, carried out polymerization of alkylene oxide, z. E.g. propylene oxide etc.), dicarboxylic acid esters (e.g. esters of dicarboxylic acids, such as adipic acid, Azelaic acid, suberic acid, sebacic acid, alkanolsuccinic acid, fumaric acid, maleic acid, with alcohols, such as butyl alcohol, hexyl alcohol, 2-ethylhexyl alcohol, Dodecyl alcohol), liquid esters of phosphoric acids, alkylbenzenes, polyphenyls (e.g. Biphenyls and terphenyls), alkyl diphenyl ethers, silicone polymers (e.g. tetraethylsilicate, tetraisopropylsilicate, Tetra- (4-methyl-2-tetraethyl) -silicate, hexyl- (4-methyl-2-pentoxy) -disiloxane, Poly (methyl) siloxane and poly (methylphenyl) siloxane).
Obige Basisöle können entweder einzeln oder im Gemisch miteinander, soweit sie mischbar sind oder durch gegenseitige Lösungsmittel mischbar gemacht wurden, verwendet werden.The above base oils can either be used individually or as a mixture with one another, provided they are miscible or made miscible by mutual solvents.
In der nachstehenden Tabelle II sind Daten über die Wirksamkeit von N-Dialkylaminoalkyl-monoalkenyl-succinimiden als Schmierölzusätze zusammengestellt. In Table II below are data on the effectiveness of N-dialkylaminoalkyl-monoalkenyl-succinimides compiled as lubricating oil additives.
Als Succinimid wurde ein N-Dimethylaminopropylalkenyl-succinimid verwendet, dessen Alkenylrest ein Molekulargewicht von annähernd 1000 aufwies und aus einem Isobutenpolymeren bestand.An N-dimethylaminopropylalkenyl succinimide was used as the succinimide used whose alkenyl radical had a molecular weight of approximately 1000 and consisted of an isobutene polymer.
Als Basisöl wurde ein SAE-10-Basisöl verwendet. Die Daten wurden in einem Caterpillar-L-1-Versuch ermittelt, der 120 Stunden unter Mil-L-2104-Bedingungen durchgeführt wurde.An SAE-10 base oil was used as the base oil. The data was obtained in a Caterpillar L-1 run that ran for 120 hours under Mil-L-2104 conditions was carried out.
Die Kolbenverfärbungszahl bezieht sich auf den Verfärbungswert des Kolbens. Nach dem Motorentest werden die drei Kolbenstege visuell untersucht, ein vollkommen schwarzer Kolbensteg erhält die Kolbenverfärbungszahl 800, während ein vollkommen sauberer Steg die Kolbenverfärbungszahl 0 erhält.The piston discoloration number refers to the discoloration value of the piston. After the engine test If the three piston lands are examined visually, a completely black piston land receives the Piston discoloration number 800, while a perfectly clean land receives the piston discoloration number 0.
Kolbenstege, deren Verfärbungswert zwischen vollkommen Schwarz und vollkommen Weiß liegt, erhalten Kolbenverfärbungszahlen innerhalb des genannten Bereiches im Verhältnis zu dem Ausmaß und Grad ihrer Verdunkelung.Piston lands with a discoloration value between completely black and completely white are preserved Piston discoloration numbers within the stated range in relation to the extent and degree their darkening.
Die »Rillenablagerungszahl« bezieht sich auf die prozentualen Ablagerungen in den Rillen der Kolbenringe. Eine saubere Rille erhält den Wert 0, während eine mit Ablagerungen angefüllte Rille die Zahl 100The "Groove Deposition Number" refers to the percentage of deposits in the grooves of the piston rings. A clean groove is given the value 0, while a groove filled with debris is assigned the number 100
ίο erhält.ίο receives.
Zusatzmittel
Succinimid (Gewichtsprozent) Additives
Succinimide (weight percent)
Versuchsergebnisse
Rillenablagerungszahl .
KolbenverfärbungszahlTest results
Groove Deposition Number.
Piston discoloration number
1,51.5
2
30,0,02
30.0.0
0,00.0
39
800,800,80039
800,800,800
Aus den in der nachstehenden Tabelle III wiedergegebenen Daten geht hervor, wieweit diese Alkenylsuccinimide der Bildung von Kolbenfirnis entgegenwirken. Diese Versuche wurden in einem FL-2-Test unter Verwendung eines Chevrolet-Motors mit sechs Zylindern bei einer Umdrehungszahl von 2500 Min.The extent to which these alkenyl succinimides are achieved can be seen from the data presented in Table III below counteract the formation of piston varnish. These trials were in a FL-2 test using a Chevrolet engine with six cylinders at a speed of 2500 min.
während 40 Stunden durchgeführt. Dieser Testversuch ist in einem »Coordinating Research Council Bulletin« unter dem Titel »Research Technique for the Determination of the Effects of Fuels and Lubricants on the Formation of Deposits During Moderate Temperature Operation« (1948) ausführlich beschrieben.carried out for 40 hours. This test attempt is in a "Coordinating Research Council Bulletin" under the title “Research Technique for the Determination of the Effects of Fuels and Lubricants on the Formation of Deposits During Moderate Temperature Operation "(1948) described in detail.
Der Kolbenfirniswert wird durch visuelle Feststellung der Firnismenge auf einem Kolbenmantel bestimmt, wobei ein sauberer Kolben den Wert »10« und ein mit schwarzem Firnis völlig überzogener Kolben den Wert »0« erhält. Dieser Kolbenfirniswert steht in Wechselbeziehung zur Straßenleistung.The piston varnish value is determined by visually determining the amount of varnish on a piston skirt determined, with a clean flask having a value of "10" and one completely coated with black varnish Piston receives the value »0«. This piston varnish value is related to road performance.
Als Dithiophosphat wurde ein Zinksalz eines Dialkyldithiophosphatgemisches verwendet, wobei einer der Alkylreste 4 Kohlenstoffatome und der andere 5 Kohlenstoffatome enthielt.A zinc salt of a dialkyl dithiophosphate mixture was used as the dithiophosphate used, one of the alkyl radicals having 4 carbon atoms and the other Contained 5 carbon atoms.
Succinimid (Gewichtsprozent)
Dithiophosphat (Gewichtsprozent)
Versuchsergebnisse
Kolbenfirniswert Additives
Succinimide (weight percent)
Dithiophosphate (weight percent)
Test results
Piston varnish value
0,0
2,50.0
0.0
2.5
0,0
6,21.0
0.0
6.2
0,54
6,90.6
0.54
6.9
0,75
7,01.5 *)
0.75
7.0
0,75
7,72.0
0.75
7.7
*) Der Alkenylrest des Succinimids bestand aus einem Isobutenpolymeren eines Molekulargewichts von etwa 700.*) The alkenyl radical of the succinimide consisted of an isobutene polymer with a molecular weight of about 700.
Wie aus obigen Daten hervorgeht, sind die Schmierölgemische, die die erfindungsgemäßen Succinimide enthalten, auffallend wirksame Schmiermittel für Verbrennungsmotoren. As can be seen from the above data, the lubricating oil blends comprising the succinimides of the present invention are contain extremely effective lubricants for internal combustion engines.
Außer den vorstehend beschriebenen Dithiophosphaten können Schmierölgemische mit einem Gehalt an
erfindungsgemäßen N - Dialkylaminoalkyl-monoalkenyl-succinimiden noch andere übliche Zusätze, wie
Reinigungsmittel, Mittel zur Verbesserung des Viskositätsindex, Rostschutzmittel,
verdickungsmittel, enthalten.In addition to the dithiophosphates described above, lubricating oil mixtures containing N-dialkylaminoalkyl-monoalkenyl-succinimides according to the invention can also contain other customary additives, such as cleaning agents, agents for improving the viscosity index, rust inhibitors,
thickeners included.
Öligkeitsmittel, Fett-Fatty oily agents
Claims (4)
USA.-Patentschrift Nr. 2 622 018.Considered publications:
U.S. Patent No. 2,622,018.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US835400A US3018291A (en) | 1959-08-24 | 1959-08-24 | Nu-dialkylaminoalkyl alkenyl succinimides |
US835390A US3018250A (en) | 1959-08-24 | 1959-08-24 | Lubricating oil compositions containing nu-dialkylaminoalkyl alkenyl succinimides |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1156926B true DE1156926B (en) | 1963-11-07 |
Family
ID=27125786
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEC22117A Pending DE1156926B (en) | 1959-08-24 | 1960-08-10 | Lubricating oils |
Country Status (4)
Country | Link |
---|---|
US (2) | US3018291A (en) |
DE (1) | DE1156926B (en) |
GB (1) | GB942818A (en) |
NL (2) | NL124306C (en) |
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Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2622018A (en) * | 1949-10-19 | 1952-12-16 | Socony Vacuum Oil Co Inc | Motor fuel |
Family Cites Families (4)
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---|---|---|---|---|
US2540800A (en) * | 1947-02-08 | 1951-02-06 | Socony Vacuum Oil Co Inc | Antirust agent |
US2490744A (en) * | 1947-02-08 | 1949-12-06 | Socony Vacuum Oil Co Inc | Antirust agent |
US2604451A (en) * | 1948-09-16 | 1952-07-22 | Gulf Research Development Co | Mineral oil compositions |
US2638450A (en) * | 1950-01-17 | 1953-05-12 | Socony Vacuum Oil Co Inc | Reaction products of nu-alkylated polyalkylenepolyamines and alkenyl succinic acid anhydrides |
-
0
- NL NL255194D patent/NL255194A/xx unknown
- NL NL124306D patent/NL124306C/xx active
-
1959
- 1959-08-24 US US835400A patent/US3018291A/en not_active Expired - Lifetime
- 1959-08-24 US US835390A patent/US3018250A/en not_active Expired - Lifetime
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1960
- 1960-08-10 DE DEC22117A patent/DE1156926B/en active Pending
- 1960-08-16 GB GB28419/60A patent/GB942818A/en not_active Expired
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2622018A (en) * | 1949-10-19 | 1952-12-16 | Socony Vacuum Oil Co Inc | Motor fuel |
Also Published As
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GB942818A (en) | 1963-11-27 |
NL124306C (en) | |
US3018250A (en) | 1962-01-23 |
US3018291A (en) | 1962-01-23 |
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