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DE1014260B - Synthetic lubricating oil - Google Patents

Synthetic lubricating oil

Info

Publication number
DE1014260B
DE1014260B DEE10810A DEE0010810A DE1014260B DE 1014260 B DE1014260 B DE 1014260B DE E10810 A DEE10810 A DE E10810A DE E0010810 A DEE0010810 A DE E0010810A DE 1014260 B DE1014260 B DE 1014260B
Authority
DE
Germany
Prior art keywords
lubricating oil
synthetic lubricating
ester
percent
weight
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
Application number
DEE10810A
Other languages
German (de)
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.)
ExxonMobil Technology and Engineering Co
Original Assignee
Exxon Research and Engineering Co
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 Exxon Research and Engineering Co filed Critical Exxon Research and Engineering Co
Publication of DE1014260B publication Critical patent/DE1014260B/en
Pending 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
    • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
    • 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
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • 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
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/025—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with condensed rings
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/284—Esters of aromatic monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/285—Esters of aromatic polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/28—Esters
    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
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    • C10M2207/28—Esters
    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • C10M2207/302—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monocarboxylic acids, dicarboxylic acids and dihydroxy compounds only and having no free hydroxy or carboxyl groups
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    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • C10M2207/304—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl groups
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    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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    • 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
    • C10M2209/084—Acrylate; Methacrylate
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
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    • C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
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    • C10M2209/11—Complex polyesters
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    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/062—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups bound to the aromatic ring
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    • C10M2215/066—Arylene diamines
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    • C10M2215/082—Amides [having hydrocarbon substituents containing less than thirty carbon atoms] containing hydroxyl groups; Alkoxylated derivatives
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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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/108—Phenothiazine
    • 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
    • C10N2030/08—Resistance to extreme temperature
    • 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
    • C10N2040/12—Gas-turbines
    • 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
    • C10N2040/12—Gas-turbines
    • C10N2040/13—Aircraft turbines

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Lubricants (AREA)

Description

Die Erfindung betrifft synthetische Schmieröle auf Grundlage von Estern, die sich besonders für Gasturbinentriebwerke von Flugzeugen eignen.The invention relates to synthetic lubricating oils based on esters, which are particularly useful for gas turbine engines suitable for aircraft.

Ein Schmiermittel für Flugzeugturbinen muß die folgenden Eigenschaften aufweisen: Gute Beständigkeit bei hohen Temperaturen, günstiges Viskositätstemperaturverhalten, Belastungsfähigkeit und niedrige Viskosität bei niedrigen Temperaturen in Verbindung mit einem niedrigen Dampfdruck bei hohen Temperaturen. Diese Eigenschaften lassen sich nicht gemeinsam durch ein wirtschaftlich arbeitendes Raffinierverfahren von Erdöl erzielen.A lubricant for aircraft turbines must have the following properties: Good resistance to high temperatures, favorable viscosity temperature behavior, load capacity and low viscosity at low temperatures in conjunction with a low vapor pressure at high temperatures. These Properties cannot be combined through an economically working refining process of crude oil achieve.

Es wurden bereits Schmierölgemische, welche diesen Eigenschaften nahekommen, vorgeschlagen, diebestimmte synthetische Ester, namentlich Diester und Komplexester oder Gemische derselben, als Hauptbestandteil enthalten. Lubricating oil blends approaching these properties have been proposed to determine synthetic esters, namely diesters and complex esters or mixtures thereof, contain as the main component.

Der bevorzugte synthetische Schmierölgrundstoff gemäß der Erfindung enthält als Hauptbestandteil eine oder mehrere Verbindungen folgender Strukturformel:The preferred synthetic lubricating oil base according to the invention contains one as the main ingredient or several compounds of the following structural formula:

R2OOCR1COOR2', R2OOCr1COOR1OOCR3,
R3COOR4OOCR3', R3(OOCR1COOR4)„OOCR1' COOR2', R3COOR4(OOCR1COOR4OnOOCR3'R 2 OOCR 1 COOR 2 ', R 2 OOCr 1 COOR 1 OOCR 3 ,
R 3 COOR 4 OOCR 3 ', R 3 (OOCR 1 COOR 4 ) "OOCR 1 ' COOR 2 ', R 3 COOR 4 (OOCR 1 COOR 4 O n OOCR 3 '

R1 und R1' sind die Reste aliphatischer Dicarbonsäuren: HOOCR1COOH-R2 und R2' sind die Reste einwertiger Alkohole: R2OH. R3 und R3' sind die Reste aliphatischer Monocarbonsäuren: R3COOH. R4 und R4' sind die Reste von Glykolen: HOR4OH. η ist eine Zahl von 1 bis 6, und zwar eine ganze Zahl oder ein Bruch, in letzterem Falle ist es ein Gemisch von Verbindungen mit 1 bis 6 als Mittelwert. Die einwertigen Alkohole sind vorzugsweise aliphatische Alkohole, Ätheralkohole oder Thioalkohole.R 1 and R 1 'are the radicals of aliphatic dicarboxylic acids: HOOCR 1 COOH-R 2 and R 2 ' are the radicals of monohydric alcohols: R 2 OH. R 3 and R 3 'are the radicals of aliphatic monocarboxylic acids: R 3 COOH. R 4 and R 4 'are the residues of glycols: HOR 4 OH. η is a number from 1 to 6, namely an integer or a fraction, in the latter case it is a mixture of compounds with 1 to 6 as the mean value. The monohydric alcohols are preferably aliphatic alcohols, ether alcohols or thioalcohols.

Die Kohlenwasserstoffkette von R2 ist zweckmäßig verzweigt; die Alkohole der Oxosynthese bieten sich hierfür vorzugsweise an; R2 hat im allgemeinen 4 bis 18 C-Atome und enthält Schwefel- und Sauerstoffatome nur in Thioäther- bzw. Ätherbindung. Die aliphatischen Monocarbonsäuren sind vornehmlich solche mit bis zu 22 C-Atomen. Als Glykole verwendet man namentlich solche der Alkylen- oder Polyalkylenglykolreihe, insbesondere Polyäthylenglykole vom Diäthylenglykol bis zum Decaäthylenglykol, oder Diole der Formel H0(CH2)m0H; η ist gleich 3 bis 12. Das Molekulargewicht und die Struktur der Ester werden vorteilhaft so gewählt, daß das fertige Öl eine Viskosität von 1 bis 20, vorzugsweise 3 bis 10 cSt bei 98,9° hat.The hydrocarbon chain of R 2 is advantageously branched; the alcohols of the oxo synthesis are preferred for this purpose; R 2 generally has 4 to 18 carbon atoms and contains sulfur and oxygen atoms only in thioether or ether bonds. The aliphatic monocarboxylic acids are mainly those with up to 22 carbon atoms. The glycols used are specifically those of the alkylene or polyalkylene glycol series, in particular polyethylene glycols from diethylene glycol to decaethylene glycol, or diols of the formula H0 (CH 2 ) m 0H; η is equal to 3 to 12. The molecular weight and the structure of the esters are advantageously chosen so that the finished oil has a viscosity of 1 to 20, preferably 3 to 10 cSt at 98.9 °.

Schmieröle mit Estern als Grundstoff haben erfahrungsgemäß den Nachteil, daß sie beim Lagern bei niedrigen Temperaturen dicker werden. Die Ursache für das Verdicken ist nicht völlig geklärt; jedenfalls ist dieser Vorgang unerwünscht. Vorliegende Erfindung zielt unter anderem darauf ab, ein Mittel zur Verfügung zu stellen, Synthetisches SchmierölExperience has shown that lubricating oils with esters as a base material have the disadvantage that they are stored at low levels Temperatures get thicker. The cause of the thickening is not fully understood; at least this is the process undesirable. The present invention aims, inter alia, to provide a means Synthetic lubricating oil

Anmelder:Applicant:

Esso Research and Engineering Company, Elizabeth, N. J. (V. St. A.)Esso Research and Engineering Company, Elizabeth, N.J. (V. St. A.)

Vertreter: E. Maemecke, Berlin-Lichterfelde West,Representative: E. Maemecke, Berlin-Lichterfelde West,

und Dr. W. Kühl, Hamburg 36, Esplanade 36 a,and Dr. W. Kühl, Hamburg 36, Esplanade 36 a,

PatentanwältePatent attorneys

Beanspruchte Priorität:Claimed priority:

Großbritannien vom 4. Juni und 15. Juli 1954
15Great Britain June 4 and July 15, 1954
15th

welches das Verdicken bei niedrigen Temperaturen wesentlich vermindert.which significantly reduces thickening at low temperatures.

Es wurde gefunden, daß Verbindungen der Formel Ar (R1) R2 in diesem Sinne wirksame Zusätze sind, in der Ar den Benzolkern, R1 eine Hydroxylgruppe, eine Carboxylgruppe oder einen Ester oder ein Anilid der letzteren und R2 eine Carboxylgruppe oder einen Ester oder ein Anilid derselben bedeutet. Beispiele für diese Verbin-It has been found that compounds of the formula Ar (R 1 ) R 2 are effective additives in this sense in which Ar is the benzene nucleus, R 1 is a hydroxyl group, a carboxyl group or an ester or an anilide of the latter and R 2 is a carboxyl group or a Means ester or an anilide thereof. Examples of this connection

düngen sind Äthylsalicylat, Mono- oder Dibutylsalicylat, Mono- oder Dibutylphthalat und Salicylanilid.fertilizers are ethyl salicylate, mono- or dibutyl salicylate, Mono- or dibutyl phthalate and salicylanilide.

Die Menge des Zusatzstoffes bestimmt sich unter anderem nach der Verdickungsneigung des Schmiermittels und der erwünschten Verbesserung. Die Zusatzmenge beträgt im allgemeinen weniger als 7 %, vorzugsweise 0,1 bis 5 %, insbesondere etwa 1 oder 2%. Der Zusatzstoff soll im Schmiermittel löslich sein und darf nicht bei den Betriebstemperaturen des Schmiermittels ausgeschieden werden. Es ist bereits bekannt, kompliziert zusammengesetzte saure Ester aus zwei- oder mehrwertigen Alkoholen und einer Fettsäure, substituierten Fettsäure oder Naphthensäure und einer zwei- oder mehrbasischen Carbonsäure zu Mineralölen als Antikorrosionsmittel zuzusetzen. Hierfür wurden z. B. vorgeschlagen saures Äthylenglykolmononaphthenat-phthalat, Äthylenglykolmononaphthenat-malat, Äthylenglykolphenylstearat-phthalat, Glyceryldistearat-phthalat und viele ähnliche Verbindungen. Hieraus läßt sich kein Schluß auf den erheblichen Rückgang der Tieftemperaturthixotropie von Schmierölen auf Grundlage von Komplexestern und Diestern durch Zusatz der wesentlich einfacher zusammengesetzten Verbindungen nach der Erfindung ziehen.The amount of additive is determined, among other things, by the tendency of the lubricant to thicken and the desired improvement. The amount added is generally less than 7%, preferably 0.1 to 5%, especially about 1 or 2%. The additive should be soluble in the lubricant and not at operating temperatures of the lubricant are excreted. It is already known complicated compound acidic esters of di- or polyhydric alcohols and a fatty acid, substituted fatty acid or naphthenic acid and to add a di- or polybasic carboxylic acid to mineral oils as an anti-corrosion agent. Therefor were z. B. suggested acidic ethylene glycol mononaphthenate phthalate, ethylene glycol mononaphthenate malate, Ethylene glycol phenyl stearate phthalate, glyceryl distearate phthalate and many similar compounds. From this no conclusion can be drawn as to the considerable decrease in the low-temperature thixotropy of lubricating oils Basis of complex esters and diesters through addition draw the much simpler composite connections according to the invention.

Es wurde ferner vorgeschlagen, zwecks Lösung bzw. Minderung der Harz- und Kohleabscheidungen in Ver-It was also proposed to dissolve or reduce the resin and carbon deposits in various

709 658/362709 658/362

brennungskraftmaschinen dem Treibstoff oder dem Schmieröl Lösungsmittelgemische zuzusetzen, die aus drei verschiedenen Komponenten bestehen, und zwar erstens Estern aliphatischer Dicarbonsäuren, Estern aromatischer Säuren, cyclischen Ketonen oder aliphatisehen Alkoholen mit Siedepunkten oberhalb 177°, zweitens Estern aliphatischer Säuren, aliphatischen Alkoholen, aliphatischen Ketonen, Benzol, Alkylbenzolen oder aromatischem Schwerbenzin mit Siedepunkten unterhalb 177° und drittens Phenolen. Diese Gemische können zwar auch Ester aromatischer Säuren enthalten, jedoch nur im Gemisch mit den übrigen angegebenen Bestandteilen, und sie. sind als Lösungsmittel für die Abscheidungen im Motor bestimmt.internal combustion engines add solvent mixtures to the fuel or the lubricating oil, which consist of consist of three different components, firstly, esters of aliphatic dicarboxylic acids, esters aromatic acids, cyclic ketones or aliphatic alcohols with boiling points above 177 °, second Esters of aliphatic acids, aliphatic alcohols, aliphatic ketones, benzene, alkylbenzenes or aromatic Heavy gasoline with boiling points below 177 ° and thirdly phenols. These mixtures can also contain esters of aromatic acids, but only in Mix with the other specified ingredients, and they. are used as a solvent for the deposits in the Engine determined.

Weiterhin ist bekannt, Schmierölen auf Esterbasis N-Acyl-p-aminophenol, Thiodiphenylamin, Hydrochinon, Brenzkatechin, Resorcin, N N'-Dibutyl-p-phenylendiamin oder Disalicyl-äthylendiamin als Oxydationsschutzmittel zuzusetzen. Zu dem gleichen Zweck wurde auch bereits der Zusatz von Phenolen, Alkylphenolen und Alkoxyphenolen, wie Phenol, 2, 4, 6-Tributylphenol, 2, 4-Dimethyl-6-butylphenol, 2, 6-Dibutylp-kresol, 2-Butyl-4~methoxyphenol, 3-Butyl-4-methoxyphenol und vielen anderen Phenolverbindungen vorgeschlagen. It is also known to use ester-based lubricating oils N-acyl-p-aminophenol, thiodiphenylamine, hydroquinone, Pyrocatechol, resorcinol, N N'-dibutyl-p-phenylenediamine or to add disalicylethylenediamine as an antioxidant. For the same purpose the addition of phenols, alkylphenols and alkoxyphenols such as phenol, 2, 4, 6-tributylphenol, 2,4-dimethyl-6-butylphenol, 2,6-dibutylp-cresol, 2-butyl-4-methoxyphenol, 3-butyl-4-methoxyphenol and many other phenolic compounds.

Abgesehen davon, daß der Zusatz dieser Stoffe ausschließlich zum Zwecke der Oxydationsverzögerung erfolgte, wurde auch der Zusatz der erfindungsgemäßen verwendeten Verbindungen zu Schmierölen auf Grundlage von Komplexestern und Diestern bisher noch nicht vorgeschlagen, wie sich denn überhaupt der Stand der Technik mit der Erscheinung der Tieftemperaturthixotropie von Esterschmierölen bisher nicht befaßt hat.Apart from the fact that these substances were added exclusively for the purpose of delaying oxidation, was also based on the addition of the compounds used according to the invention to lubricating oils of complex esters and diesters has not yet been proposed, how the state of the Technik has not previously dealt with the phenomenon of low temperature thixotropy of ester lubricating oils.

Die folgende Tabelle gibt eine Vorstellung von der Wirksamkeit einiger als Beispiele gegebenen Zusatzstoffe. Zusammensetzung eines Schmiermittels: 20 % Komplexester*) Probe E, 20% Dioctylsebacat, 60°/0 Dinonylsebacat + 3,85 % Polymethacrylsäureester + 1 °/0 reines Phenothiazin.The following table gives an idea of the effectiveness of some of the additives given as examples. Composition of a lubricant: 20% complex ester *) sample E, 20% dioctyl sebacate, 60 ° / 0 dinonyl sebacate + 3.85% polymethacrylic acid ester + 1 ° / 0 pure phenothiazine.

40 20 % Komplexester*) Probe D, 20 % Dioctylsebacat, S0°/Q Dinonylsebacat + 3,6 °/0 Polymethacrylsäureester + 1 % reines Phenothiazin.40 20% complex ester *) sample D, 20% dioctyl sebacate, S0 ° / Q dinonyl sebacate + 3.6 ° / 0 polymethacrylic acid ester + 1% pure phenothiazine.

ZusatzstoffAdditive

Keine Zusätze 5 740 14 450No additions 5 740 14 450

2°/0 Glycerinmonostearat ... 6 950 36 0002 ° / 0 glycerol monostearate ... 6,950 36,000

% Hexachlorbenzol 5 850 19 280% Hexachlorobenzene 5,850 19,280

*) Aus Sebacinsäure, 2-Äthylhexanol und Polyglykol 200.*) From sebacic acid, 2-ethylhexanol and polyglycol 200.

Viskosität, cSt bei —40°Viscosity, cSt at -40 °

Vor BehandlungBefore treatment

NachTo

Behandlungtreatment

bei —54°at -54 °

(17 Stunden)(17 hours)

Viskosität,Viscosity, cSt bei — 40°cSt at - 40 ° ZusatzstoffAdditive Vorbefore Behandlungtreatment Keine Zusätze No additives 5 7405 740 2 % Äthylsalicylat 2% ethyl salicylate 5 4055 405 l,4°/0 Butylsalicylat...1.4 ° / 0 butyl salicylate ... 5 3055 305 1 % Butylphthalat ...1% butyl phthalate ... 5 6105 610 2°/0 Butylphthalat ...2 ° / 0 butyl phthalate ... 5 6955 695 1% Salicylanilid1% salicylanilide 6 2416 241 Nach
Behandlung beiTo
Treatment at — 54°- 54 ° (17 Stunden)(17 hours) 10 62010 620 6 0806 080 6 2506 250 6 9906,990 6 2906 290 7 3507 350

*) Aus Sebacinsäure, 2-Äthylhexanol und Polyglykol 200.*) From sebacic acid, 2-ethylhexanol and polyglycol 200.

Aus den beiden letzten Beispielen ersieht man, daß der aromatische Kern offenbar von Bedeutung ist und daß andere Substituenten, z. B. Halogene, unwirksame Verbindungen liefern.From the last two examples it can be seen that the aromatic nucleus is obviously important and that other substituents, e.g. B. provide halogens, ineffective compounds.

Claims (5)

Patentansprüche:Patent claims: 1. Synthetisches Schmieröl auf Grundlage eines Gemisches eines Komplexesters und eines Diesters aliphatischer Dicarbonsäuren, gekennzeichnet durch einen Zusatz an einer Verbindung der Formel Ar (R1) R2, in der Ar den Benzolkern, R1 eine Hydroxylgruppe, eine Carboxylgruppe oder einen Ester oder ein Anilid der letzteren und R2 eine Carboxylgruppe oder einen Ester oder ein Anilid derselben bedeutet.1. Synthetic lubricating oil based on a mixture of a complex ester and a diester of aliphatic dicarboxylic acids, characterized by the addition of a compound of the formula Ar (R 1 ) R 2 , in which Ar is the benzene nucleus, R 1 is a hydroxyl group, a carboxyl group or an ester or an anilide of the latter and R 2 represents a carboxyl group or an ester or an anilide thereof. 2. Synthetisches Schmieröl nach Anspruch 1, dadurch gekennzeichnet, daß es den Zusatz in einer Menge von nicht mehr als 7 Gewichtsprozent, vorzugsweise in einer Menge von 0,1 bis 5 Gewichtsprozent, insbesondere etwa 1 oder 2 Gewichtprozent, enthält.2. Synthetic lubricating oil according to claim 1, characterized in that it is the additive in one Amount of not more than 7 percent by weight, preferably in an amount of 0.1 to 5 percent by weight, especially about 1 or 2 percent by weight. 3. Synthetisches Schmieröl nach Anspruch 1 und 2, dadurch gekennzeichnet, daß der Zusatzstoff Äthylsalicylat, Butylphthalat oder Salicylanilid ist.3. Synthetic lubricating oil according to claim 1 and 2, characterized in that the additive ethyl salicylate, Butyl phthalate or salicylanilide. 4. Synthetisches Schmieröl nach Anspruch 1 bis 3, dadurch gekennzeichnet, daß es nicht weniger als 20 Gewichtsprozent Komplexester enthält.4. Synthetic lubricating oil according to claim 1 to 3, characterized in that it is not less than Contains 20 percent by weight complex ester. 5. Synthetisches Schmieröl nach Anspruch 1 bis 4, dadurch gekennzeichnet, daß der synthetische Ester eine Viskosität von 1 bis 20, vorzugsweise 3 bis 10 cSt bei 98,9° besitzt.5. Synthetic lubricating oil according to claim 1 to 4, characterized in that the synthetic ester has a viscosity of 1 to 20, preferably 3 to 10 cSt at 98.9 °. In Betracht gezogene Druckschriften: USA.-Patentschrift Nr. 2 604 450; britische Patentschriften Nr. 668 663, 680 438;References considered: U.S. Patent No. 2,604,450; British Patent Nos. 668 663, 680 438; französische Patentschriften Nr. 974 374, 1 058 878; Chem. Zentralblatt, 1951, II, S. 920 (kanadische Patentschrift Nr. 471674); 1951, II, S. 2829 (schwedische Patentschrift Nr. 129 412).French Patent Nos. 974,374, 1,058,878; Chem. Zentralblatt, 1951, II, p. 920 (Canadian patent No. 471674); 1951, II, p. 2829 (Swedish Patent No. 129 412). 709 658/362 8.57709 658/362 8.57
DEE10810A 1954-06-04 1955-06-02 Synthetic lubricating oil Pending DE1014260B (en)

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GB16599/54A GB776669A (en) 1954-06-04 1954-06-04 Improvements of low temperature stability of synthetic lubricants

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1058673B (en) 1955-01-04 1959-06-04 Exxon Research Engineering Co Synthetic lubricating oils
DE1064665B (en) 1955-03-04 1959-09-03 British Petroleum Co Lubricant mixture
DE1081587B (en) 1958-01-02 1960-05-12 Exxon Research Engineering Co Lubricating oil

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA471674A (en) * 1951-02-20 The Pure Oil Company Gum and carbon deposit solvents and methods of using the same
FR974374A (en) * 1947-10-28 1951-02-21 Bataafsche Petroleum Lubricants
GB668663A (en) * 1949-04-21 1952-03-19 Standard Oil Dev Co Improvements in or relating to synthetic ester lubricants
US2604450A (en) * 1950-12-22 1952-07-22 Standard Oil Dev Co Lubricating grease composition
GB680438A (en) * 1948-10-01 1952-10-08 Standard Oil Dev Co Complex glycol esters for use as or in lubricants
FR1058878A (en) * 1951-03-02 1954-03-19 Standard Oil Dev Co Compound lubricating oil

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA471674A (en) * 1951-02-20 The Pure Oil Company Gum and carbon deposit solvents and methods of using the same
FR974374A (en) * 1947-10-28 1951-02-21 Bataafsche Petroleum Lubricants
GB680438A (en) * 1948-10-01 1952-10-08 Standard Oil Dev Co Complex glycol esters for use as or in lubricants
GB668663A (en) * 1949-04-21 1952-03-19 Standard Oil Dev Co Improvements in or relating to synthetic ester lubricants
US2604450A (en) * 1950-12-22 1952-07-22 Standard Oil Dev Co Lubricating grease composition
FR1058878A (en) * 1951-03-02 1954-03-19 Standard Oil Dev Co Compound lubricating oil

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1058673B (en) 1955-01-04 1959-06-04 Exxon Research Engineering Co Synthetic lubricating oils
DE1064665B (en) 1955-03-04 1959-09-03 British Petroleum Co Lubricant mixture
DE1081587B (en) 1958-01-02 1960-05-12 Exxon Research Engineering Co Lubricating oil

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Publication number Publication date
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GB776669A (en) 1957-06-12

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