DE2257708A1 - OIL PREPARATIONS - Google Patents
OIL PREPARATIONSInfo
- Publication number
- DE2257708A1 DE2257708A1 DE2257708A DE2257708A DE2257708A1 DE 2257708 A1 DE2257708 A1 DE 2257708A1 DE 2257708 A DE2257708 A DE 2257708A DE 2257708 A DE2257708 A DE 2257708A DE 2257708 A1 DE2257708 A1 DE 2257708A1
- Authority
- DE
- Germany
- Prior art keywords
- groups
- mixture
- preparation according
- alkyl
- 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.)
- Ceased
Links
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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
- 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
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- 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
- C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
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- 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
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- 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
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- 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
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- 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
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- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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- C10M2207/283—Esters of polyhydroxy compounds
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- C10M2207/286—Esters of polymerised unsaturated acids
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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
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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
- C10M2207/302—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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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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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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- C10M2207/40—Fatty vegetable or animal oils
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- C10M2207/402—Castor oils
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- C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
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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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- C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
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- C10M2209/112—Complex polyesters having dihydric acid centres
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
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- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
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- C10M2219/108—Phenothiazine
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- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/041—Triaryl phosphates
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- C10M2223/043—Ammonium or amine salts thereof
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- C10M2229/04—Siloxanes with specific structure
- C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
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- 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
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
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- 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)
- Lubricants (AREA)
Description
DR. BERG DIPL.-ING. STAPFDR. BERG DIPL.-ING. STAPF
PATENTANWÄLTE
8 MÜNCHEN 86, POSTFACH 860245PATENT LAWYERS
8 MUNICH 86, POST BOX 860245
Ihr Zeichen Your ref.Your sign Your ref.
Unser Zeichen Our ref.Our mark Our ref.
8 MÖNCHEN 80 OA fJniI 8 MONKS 80 OA fJ niI
Anwaltsakte 22 Be/Ro Lawyer file 22 Be / Ro
Esso Research and Engineering Company Linden / USAEsso Research and Engineering Company Linden / USA
"Schmierölzubereitungen""Lubricating Oil Preparations"
Diese Erfindung betrifft SchmierölZubereitungen, die Aminsalze von Phosphorsäuren enthalten.This invention relates to lubricating oil formulations which Contain amine salts of phosphoric acids.
Schmieröle benötigen gewöhnlich Zusätze zur Verbesserung ihrer Eigenschaften gegen Abrieb und ihrer Hochdruckleistungen, und dies trifft besonders für Schmieröle für Flugzeuge, z.B. Flugturbinenschmieröle zu. Es wurden bisher bestimmte Aminsalze von Phosphor und Thio-Lubricating oils usually need additives for improvement their properties against abrasion and their high pressure performance, and this is particularly true of aircraft lubricating oils, e.g., aviation turbine lubricating oils. It so far certain amine salts of phosphorus and thio-
-2--2-
3098^2/10903098 ^ 2/1090
(0811) 988272 S8 70 43 983310(0811) 988272 S8 70 43 983310
Telegramme: BERGSTAPFPATENT München TELEX: 0524560 BERG dTelegrams: BERGSTAPFPATENT Munich TELEX: 0524560 BERG d
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phosphorsäuren als gleitverbessernde Additive vorgeschlagen, aber diese sind, obgleich einige gute gleitverbessernde Eigenschaften aufweisen, korrosiv und/oder mit Silikonelastomeren unverträglich. Es wurde nunmehr gefunden, daß bestimmte Aminsalze nicht nur gute gleitverbessernde und Hochdruckeigenschaften, sondern auch gute Verträglichkeit mit Silikonelastomeren aufweisen. Weiterhin haben sie gute Korrosionseigenschaften.,Phosphoric acids have been suggested as anti-slip additives, but these, although some good, are anti-slip additives Have properties, corrosive and / or incompatible with silicone elastomers. It has now been found that certain amine salts not only have good slip-improving and extreme pressure properties, but also good compatibility with silicone elastomers. They also have good corrosion properties.,
Die Erfindung betrifft eine Schmierölzubereitung, die ein
Schmieröl und ein Gemisch bestimmter Aminsalze enthält. Dieses Gemisch umfaßt (a) ein quarternäres Hydrocarbylammoniumsalz
eines Mono(C--G.J-alkyldihydrogenphosphats
der allgemeinen Formel
R5OThe invention relates to a lubricating oil preparation which contains a lubricating oil and a mixture of certain amine salts. This mixture comprises (a) a quaternary hydrocarbyl ammonium salt of a mono (C 6 -C 8 alkyl dihydrogen phosphate of the general formula
R 5 O
R1R2R5H4N(KR 1 R 2 R 5 H 4 N (K
und (b) ein quarternäres Hydrocarbylammoniumsala eines Di-(Cj-C1, )-alkylhydrogenphosphats der allgemeinen formeland (b) a quaternary hydrocarbylammonium ala of a di- (Cj-C 1 ,) -alkyl hydrogen phosphate of the general formula
R5O^ OR 5 O ^ O
^ ONR1R2R5R4 ,^ ONR 1 R 2 R 5 R 4 ,
worin die Reste R , R , R^ und R gleiche oder verschie-in which the radicals R, R, R ^ and R are identical or different
12 "5 dene Hydrocarbylgruppen sind, wobei die Reste R1 R , R12 "5 dene hydrocarbyl groups, where the radicals R 1 R, R
4
und R eine Gesamtzahl von wenigstens 10 Kohlenstoffatomen enthalten, und R. .und R gleicheoder veraohiedeiie C1-C1,-4th
and R contain a total of at least 10 carbon atoms, and R.. and R the same or different C 1 -C 1 , -
309822/1098 -3-309822/1098 -3-
Alkylgruppen sind.Are alkyl groups.
Die Gesamtanzahl der Kohlenstoffatome in den Resten R ,,The total number of carbon atoms in the radicals R ,,
2 3 4 ■"'-·'2 3 4 ■ "'- ·'
R , R und R muß wenigstens 10 sein und ist vorzugsweise höher, z.B. wenigstens 14. Das bedeutet, daß, obgleich eine oder mehrere der Gruppen relativ kurzkettig, z.B» Methyl oder Äthyl sein können, eine oder mehrere der anderen Gruppen langkettig, z.B.Decyl, Dodeeyl usw. sein müssen. Wenn das Gemisch der Aminsalze den Mineralölen zugegeben wird, ist die bevorzugte Maximalanzahl der Kohlenstoff atome in den Resten R1, R2, R5 und R4", 100, während wenn das Gemisch synthetischen Esterölen zugegeben werdensoll, die bevorzugte Maximalanzahl der KohlenstoffatomeR, R and R must be at least 10 and is preferably higher, e.g. at least 14. This means that although one or more of the groups can be relatively short-chain, e.g., methyl or ethyl, one or more of the other groups can be long-chain, e.g. Must be Dodeeyl, etc. When the mixture of amine salts is added to the mineral oils, the preferred maximum number of carbon atoms in the radicals R 1 , R 2 , R 5 and R 4 "is 100, while when the mixture is to be added to synthetic ester oils, the preferred maximum number of carbon atoms
1 2 '3 4 ist ο Obgleich die Gruppen.R , R , R und R verschieden sein können, wird bei der Durchführung der Erfindung bevorzugt, daß wenigstens zwei der Gruppen gleich sind, ZoB„ R1 und R2 Methyl, R5 Äthyl und R4 Octadecyl, oder R1 und R Methyl, R und R Octadecyl sind. Die Gruppen R1, R2 R und R können grad- oder verzweigtkettig sein. Die Reste R1, R., R5 und R4 können Alkaryl-, Aralkyl-, Cycloalkyl- oder Arylgruppen sein, sind aber vorzugsweise Alkylgruppen.1 2 '3 4 is ο Although the groups R, R, R and R can be different, it is preferred when carrying out the invention that at least two of the groups are the same, ie, R 1 and R 2 methyl, R 5 ethyl and R 4 are octadecyl, or R 1 and R are methyl, R and R are octadecyl. The groups R 1 , R 2, R and R can be straight or branched chain. The radicals R 1 , R., R 5 and R 4 can be alkaryl, aralkyl, cycloalkyl or aryl groups, but are preferably alkyl groups.
12 3 Es können daher eine oder mehrere der Gruppen R , R , R und12 3 One or more of the groups R, R, R and
A . ■" 'A. ■ "'
R Methyl, Äthyl, n-Propyl, iso-Butyl, n-Hexyl, n-Decyl, 2-Äthyldecyl, n-0ctadecyl, m-Tolyl, p-Äthylphenyl, Benxyl, Gycloootyl, Phenyl oder Kaphthyl sein, mit der Maßgabe, daß die Gesamtanzahl der Kohlenstoffatome in den 4 Gruppen wenigstens 10 ist. Besonders bevorzugt wird, daß wenigstens 3R methyl, ethyl, n-propyl, iso-butyl, n-hexyl, n-decyl, 2-ethyldecyl, n-octadecyl, m-tolyl, p-ethylphenyl, benxyl, Be Gycloootyl, Phenyl or Kaphthyl, with the proviso that the total number of carbon atoms in the 4 groups at least 10 is. It is particularly preferred that at least 3
-4-309822/1098 '-4-309822 / 1098 '
1 O^ A 1 O ^ A
der Gruppen R , R , Ir und R gleiche Alkylgruppen, z.B„ alle die gleiche Gruppe wie n-Butyl-, oder 5 Gruppen Octylgruppen wie bei den Hexyltrioctylammoniumsalzen sind.the groups R, R, Ir and R are identical alkyl groups, e.g. all the same group as n-butyl, or 5 groups of octyl groups as with the hexyltrioctylammonium salts.
Obgleich Jede der Gruppen R , R , R"^ und R ale Hydrocarbylgruppen bezeichnet werden, können sie jedoch durch polare Substituenten, z.B. Ohlor- oder Bromatome oder durch Keto- oder Äthergruppen substituiert sein, mit der Maßgabe, daß diese Substituenten nioht in solch großen Anteilen vorhanden sind, daß sie den KohlenwasserstoffCharakter der Gruppe wesentlich verändern} so sollten beispielsweise die Gruppen nicht mehr als 10 Gew.# polaren Substituenten, bezogen auf das Gewicht des Hydro car byl teils der Gruppe, enthalten·Although each of the groups R, R, R "^ and R al are hydrocarbyl groups but they can be designated by polar substituents, e.g. chlorine or bromine atoms or by keto or ether groups, with the proviso that these substituents are not present in such large proportions are that they substantially change the hydrocarbon character of the group} so, for example, the groups should no more than 10 wt. # of polar substituents, based on the weight of the hydrocarbyl part of the group.
5 6
Die Gruppen R und R sind Alkylgruppen mit 1, 2, 3 oder
4 Kohlenstoffatomen, d.h. sie sind Methyl-, Äthyl-, n-Propyliso-Propyl,
η-Butyl, sec-Butyl-oder iso-Butylgruppen. Es5 6
The groups R and R are alkyl groups with 1, 2, 3 or 4 carbon atoms, ie they are methyl, ethyl, n-propyl iso-propyl, η-butyl, sec-butyl or iso-butyl groups. It
5 6 wird bevorzugt, daß beide Reste R und R gleich sind, z.B.5-6 it is preferred that both R and R are the same, e.g.
beide Methyl- oder beide Äthylgruppen sind. Besonders bevorzugte Salze sind Gemische von Tetra-n-butylammoniumsalζen von Dimethylhydrogenphosphat und Methyldihydrogenphosphat und Gemische von Hexyltrioctylammoniumsalzen von Methyldihydrogenphosphat und Dimethylhydrogenphosphat·are both methyl or both ethyl groups. Particularly preferred salts are mixtures of tetra-n-butylammonium salts of dimethyl hydrogen phosphate and methyl dihydrogen phosphate and mixtures of hexyl trioctyl ammonium salts of methyl dihydrogen phosphate and dimethyl hydrogen phosphate
Das Gemisch der sauren Phosphate, aus denen die (juarternären Ammoniumsalze (a) und (b) abstammen, wird am besten in der Weise hergestellt, daß man Phosphorpentoxid mit einem O1-C4-Alkohol oder Gemisch von Alkoholen im Verhältnis von etwaThe mixture of the acidic phosphates from which the juarternary ammonium salts (a) and (b) are derived is best prepared by mixing phosphorus pentoxide with an O 1 -C 4 alcohol or mixture of alcohols in a ratio of about
309822/1098 "5~309822/1098 " 5 ~
..3 Mol -Alkohol pro Mol Pentoxid umsetzt. Das Gemisch von Alkylphosphaten wird nach der.folgenden Reaktion erhalten:..3 moles of alcohol per mole of pentoxide. The mixture of alkyl phosphates is obtained after the following reaction:
p- + 3R5OHp- + 3R 5 OH
Bei der Durchführung kann Phosphorpentoxid kräftig in trockenem Äther gerührt und der Alkohol tropfenweise in ausreichender Geschwindigkeit zugegeben werden, daß der Äther unter mäßigem Rückfluß gehalten werden kann. Das Produkt kann danach zur Entfernung iron irgendwelchem nicht umgesetztem Phosphorpentoxid filtriert, und der Äther durch Verdampfen unter Vakuum entfernt werden. 'When carrying out phosphorus pentoxide can vigorously in dry ether and add the alcohol drop by drop at a sufficient rate that the ether can be kept under moderate reflux. The product can then remove any unreacted iron Phosphorus pentoxide filtered, and the ether by evaporation removed under vacuum. '
Das Gemisch der so erhaltenen Alkylphosphate wird mit einer quarternären Ammoniumhydroxidlösung (z.B. 40^iger, wäßriger Lösung) umgesetzt, Solche Losungen können zweckmäßigerweise dadurch hergestellt werden, .daß man bei Raumtemperatur ein tertiäres Amin mit einem Alkylhalogenid unter Bildung des quarternären Ammoniumhalogenids, z.B. nach der folgenden Gleichung umsetzt:The mixture of the alkyl phosphates thus obtained is with a quaternary ammonium hydroxide solution (e.g. 40%, aqueous Solution) implemented, such solutions can expediently be produced by .that one at room temperature tertiary amine with an alkyl halide to form the quaternary ammonium halide such as the following Implements equation:
R-K + RX ——» R-N^ -R-K + RX —— »R-N ^ -
RRRR
Dieses Halogenid mischt man mit einer Lösung,von Silberoxid in Wasser und rührt das Reaktionsgemisch. Das Silber-This halide is mixed with a solution of silver oxide in water and stir the reaction mixture. The silver-
3 09822/1098 ~6"3 09822/1098 ~ 6 "
halogenid wird auegefällt und man erhält eine Lösung, die quartemäre Ammoniumkationen und Hydroxidanionen enthält. Es kann auch das quartemäre Ammoniumhalogenid in das entsprechende Hydroxid dadurch umgewandelt werden, daß man ein geeignetes Iontnauataueeherharz, z.B. ein Polystyrol/Divinylbenzolmisohpolymerisat» das mit tertiären Amingruppen subatituiert ist, verwendet.Halide is precipitated and a solution is obtained that contains quaternary ammonium cations and hydroxide anions. The quaternary ammonium halide can also be converted into the corresponding hydroxide by a suitable Iontnauataueeher resin, e.g. a polystyrene / divinylbenzene isohpolymer » which is substituted with tertiary amine groups is used.
Wenn man solche quartemären Ammoniumhydroxidlösungen mit dem Gemisch der Alkylphosphate umsetzt, wird das gewünschte Gemisch der Aminsalze (a) und (b) gebildet. Das Molverhältnis von (a) zu (b), das mittels dieser Verfahren gebildet wird, ist etwa 1i1 und dieses ist das bevorzugte Verhältnis.If you have such quaternary ammonium hydroxide solutions Reacts the mixture of alkyl phosphates, the desired Mixture of the amine salts (a) and (b) formed. The molar ratio of (a) to (b) formed by this method is about 1i1 and this is the preferred ratio.
Die Menge des Aminsal«gemische, die einem'Schmieröl zugegeben wird, besondere einem Plugturbinenöl, ist gewöhnlich ein kleinerer Anteil, vorzugsweise 0,001 bis 10 Gew.^, z.B. 0,01 bis 5,0 Gew.?£, bezogen auf das Gewicht des Schmieröls.Mix the amount of amine salt that is added to a lubricating oil , especially a plug turbine oil, is common a minor proportion, preferably 0.001 to 10% by weight, e.g. 0.01 to 5.0 wt% based on the weight of the lubricating oil.
Das Schmieröl kann irgendein Mineralöl, Tieröl, Fischöl, Pflanzenöl oder synthetisches Ol sein, beispielsweise Petrol ö,lfraktionen von Spindelöl bis Schmieröl bis SAE 30, 40 oder 50, Rizinusöl, Tier- oder Fischöle oder oxidiertes Mineralöl, z.B. Palmöl, Fettöl, falgöl, Erdnußöl oder Spermöl. The lubricating oil can be any mineral oil, animal oil, fish oil, Vegetable oil or synthetic oil, for example petroleum oil fractions from spindle oil to lubricating oil up to SAE 30, 40 or 50, castor oil, animal or fish oils, or oxidized Mineral oil, e.g. palm oil, fatty oil, fallow oil, peanut oil or sperm oil.
Das bevorzugte Schmieröl ist «in synthetischer Ester und zu geeigneten Diester» gehören di· Ester der allgemeinen FormelThe preferred lubricating oil is in synthetic esters and in suitable diesters include diesters of the general formula
30 9830 98
.-■■■■■,■■.. .- ..-7-.- ■■■■■, ■■ .. .- ..- 7-
worin R eine Cg- bis C-J2-Alkylgruppe ist, während R^ eine C4- Tais G^q gesättigte aliphatisclie Kohlenwasserstoffgruppe oder eine Äther-unterbrochene gesättigte aliphatische Kohlenwasserstoffgruppe ist. Die oben angegebenen Esterarten, können aus Alkoholen und Dicarbonsäuren oder Glykolen und Monocarbonsäuren hergestellt werden.wherein R is a Cg to CJ 2 alkyl group, while R ^ is a C 4 - Tais G ^ q saturated aliphatic hydrocarbon group or an ether-interrupted saturated aliphatic hydrocarbon group. The types of esters given above can be prepared from alcohols and dicarboxylic acids or glycols and monocarboxylic acids.
Eine weitere geeignete Klasse an Esterschmiermittel sind die Polyester, die dadurch hergestellt werden, daß man mehrwertige Alkohole, z.B. solche mit 2 bis 12 Hydroxylgruppen pro Molekül und 2 bis 40 Kohlenstoffatomen pro Molekül, wie Trimethylolpropan, Pentaerythrit und Di-pentaerythrit mit. Mono- und/oder Di-carbonsäuren, wie Buttersäure, Gapronsäure, Oaprylsäure und Pelargonsäure oder Adipin-, Sebaziri- oder Azelainsäuren, umsetzt.Another suitable class of ester lubricants are the polyesters made by polyvalent Alcohols, e.g., those having 2 to 12 hydroxyl groups per molecule and 2 to 40 carbon atoms per molecule, such as Trimethylolpropane, pentaerythritol and di-pentaerythritol with. Mono- and / or dicarboxylic acids, such as butyric acid, caproic acid, oaprylic acid and pelargonic acid or adipic, sebacic acid or azelaic acids.
Die Komplexester die als-Bäsisöle verwendet werden können, werden durch Veresterungsreaktionen zwischen einer Dicarbonsäure, einem Glykol und einem Alkohol und/oder einer Monocarbonsäure gebildet. Diese Ester haben die nachfolgenden allgemeinen Formeln;The complex esters that can be used as base oils, are produced by esterification reactions between a dicarboxylic acid, a glycol and an alcohol and / or a monocarboxylic acid. These esters have the following general formulas;
R4COO-E3- (0OCR2COO-R3)n-00CR4 R1-OOCR2COO-(R3-OOCR2COO)n-R1 R 4 COO-E 3 - (0OCR 2 COO-R 3 ) n -00CR 4 R 1 -OOCR 2 COO- (R 3 -OOCR 2 COO) n -R 1
R1-C0OCR2COO-R3)n00CR4 : R 1 -C0OCR 2 COO-R 3 ) n 00CR 4:
worin R1 von einem einwertigen Alkohol abstammende Alkylreste, Rg von einer Dicarbonsäure, z.B. Alkandionsauren ab-wherein R 1 is derived from a monohydric alcohol, Rg is derived from a dicarboxylic acid, for example alkanedioic acids.
-8-309822/1098 -8- 309822/1098
— ο —- ο -
stammende Kohlenwasserstoffreste, R, zweiwertige Kohlenwasserstoff-
oder Kohlenwasserstoffoxireste, wie OH2(OH2) -,
oder CH2OH2(00H2OH2)n- oder OH2CH(OH3) (0OH2OH(CH5))n~,
die von einem Alkylenglykol oder Polyalkylenglykol abstammen, sind, während R, die von einer Monocarbonsäure abstammende
Alkylgruppe ist, "n·1 in dem Komplex Estermolekül eine
ganze Zahl, gewöhnlich im Bereich von 1 bis 6 ist, die nach der gewünschten Viskosität des Produkts, wie durch das relative
Molarverhältnis des Glykole oder Polyglykols zu der Dicarbonsäure
gesteuert wird. Bei der Herstellung der Komplexester werden immer einige einfache Ester gebildet werden,
doh· solche, worin η = 0, jedoch werden diese in* allgemeinen nur einen geringen Anteil ausmachen. Im allgemeinen werden
diese Komplexester eine Gesamtzahl von 15 bis- 80, z.B.
20 bis 65 Kohlenstoffatome pro Molekül aufweisen.derived hydrocarbon radicals, R, divalent hydrocarbon or hydrocarbonoxy radicals, such as OH 2 (OH 2 ) -,
or CH 2 OH 2 (00H 2 OH 2 ) n - or OH 2 CH (OH 3 ) (0OH 2 OH (CH 5 )) n ~,
which are derived from an alkylene glycol or polyalkylene glycol, while R, which is the alkyl group derived from a monocarboxylic acid, "n * 1 in the complex ester molecule is an integer, usually in the range of 1 to 6, depending on the desired viscosity of the product, as controlled by the relative molar ratio of the glycols or polyglycols to the dicarboxylic acid. In the preparation of the complex esters, some simple esters will always be formed,
doh · those in which η = 0, but these will generally only make up a small proportion. In general, these complex esters will have a total of 15 to 80, e.g.
Have 20 to 65 carbon atoms per molecule.
Besonders geeignete Schmiermittel sind Ester von mehrwertigen Alkoholen der FormelParticularly suitable lubricants are esters of polyhydric alcohols of the formula
CH2OHCH 2 OH
R-C- CH9OH CH2OHRC-CH 9 OH CH 2 OH
worin R eine CH2OH-Gruppe oder eine Alkylgruppe, zfB. eine
Alkylgruppe mit 1 bis 6 Kohlenstoffatomen ist. Geeignete
Ester dieser Art sind daher die Neopentylpolyolester von
Trimethyloläthan, Trimethylolpropan, Trimethylolbutan und
von Pentaerythrit oder Di-pentaerythrit.wherein R is a CH 2 OH group, or an alkyl group such as a f
Is an alkyl group of 1 to 6 carbon atoms. Suitable
Esters of this type are therefore the neopentyl polyol esters of
Trimethylolethane, trimethylolpropane, trimethylolbutane and
of pentaerythritol or di-pentaerythritol.
309822/1098309822/1098
■ - 9 - ■■ - 9 - ■
Die bevorzugten zur Veresterung des Trimethylolpropan ver- : wendeten Säuren, sind die C^-C-p-Monocarbonsäuren. Besonders bevorzugt werden die C^-C^Q-Ester, ζ.B. Cg (Capryl-) und Og (Pelargon-)säureester. Gemische von diesen CU-CL2-SaU-ren können verwendet werden. Wenn man ein solches Säuregemisch verwendet, wird ein Gemisch bevorzugt, das im Durchschnitt 8 bis 9 Kohlenstoffatome aufweist. Obgleich schwieriger herzustellen, wird es sogar bevorzugt, daß eine Methylolgruppe mit einer neο-Heptansäure, Z0B. 2O2-Dimethylpentansäure verestert ist, und die anderen Methylolgruppen mit nicht gehinderten Säuren, z.B» Pelargonsäuren verestert sind. Dieser besondere Ester ist thermisch wesentlich stabiler als der vollständig gehinderte Ester, hat aber höhere !Tüchtigkeit und überlegene Niedertemperatureigenschaften.The preferred comparable for the esterification of trimethylolpropane: used acids are the C ^ Cp-monocarboxylic acids. Particularly preferred are the C ^ -C ^ Q esters, ζ.B. Cg (caprylic) and Og (pelargonic) acid esters. Mixtures of these CU-CL 2 -SaUs can be used. When using such a mixture of acids, a mixture having an average of 8 to 9 carbon atoms is preferred. Although more difficult to manufacture, it is even preferred that a methylol group with a neο-heptanoic acid, Z 0 B. 2 O 2-dimethylpentanoic acid is esterified, and the other methylol groups with not hindered acids, for example, "esterified Pelargonsäuren. This particular ester is much more thermally stable than the fully hindered ester, but has higher performance and superior low temperature properties.
Die bevorzugten Säuren zur Veresterung von Pentaerythrit sind die C.-G.Q-Monooarbonsäuren, wobei die besonders bevorzugten Ester solche von C^ bis Cg-Säuren, ZoB* n-Valerian-* Isovalerian-, 2-lthylbutter-, Öapron-j n-Heptyi-i n-Octan- oder 2-Äthylhexonsäuren oder ein Gemisch von Oc-Öq-Säuren sind.The preferred acids for the esterification of pentaerythritol are the C.-G.Q-monooarboxylic acids, the particularly preferred esters being those of C ^ to Cg acids, ZoB * n-Valerian- * Isovalerian-, 2-ethylbutter-, Öapron-j n-Heptyi-i n-Octan or 2-ethylhexonic acids or a mixture of Oc-Öq acids are.
Gemische von Diestern mit geringen Anteilen an einem oder mehreren Verdickungsmittel können ebenso als Schmiermittel verwendet werden. So kann man beispielsweise Gemische verwenden, die bis zu 50 VoI»5^ einen oder mehrere wasserunlösliche Polyoxyalkylenglykole» beispielweise Polyäthylenoder Polypropylenglykol oder gemisohten Oxyäthylen/Oxypro-Mixtures of diesters with small proportions of one or several thickeners can also be used as lubricants. For example, you can use mixtures, which, up to 50%, are one or more water-insoluble Polyoxyalkylene glycols, for example polyethylene or Polypropylene glycol or mixed oxyethylene / oxypro-
309822/109Ö309822 / 109Ö
pylenglykol enthalten·contain pylene glycol
Zu Formulierungen! die zur Gasturbinenschmierung geeignet sind, gehören 65 bis 90 YoI,Ji τοη einem oder mehreren Diestern von Azelainsäure oder Sebazinaäure und einem Cg-G-gverzweigtkettigern Alkohol} besonders 2-Äthylhexanol oder "Oxo"-Alkohole, die vorherrschend C8, Cg oder C1Q Alkohole enthalten oder Gemische von solchen Alkoholen und 35 bis Polyoxyalkylenglykolether der allgemeinen Formel:To formulations! which are suitable for gas turbine lubrication include 65 to 90 YoI, Ji τοη one or more diesters of azelaic acid or sebacic acid and a Cg-G branched-chain alcohol} especially 2-ethylhexanol or "oxo" alcohols, which are predominantly C 8 , Cg or C 8 1 Q contain alcohols or mixtures of such alcohols and 35 bis polyoxyalkylene glycol ethers of the general formula:
RORO
CH-OCH-O
R,R,
worin die Reste R^, R und Rg Wasserstoff oder Ö^ö^ gruppen Bind und worin nicht mehr als zwei dieser Gruppen Wasserstoff sind und η'eine ganze Zahl größer als 1 ist* Besonders wertvolle Verbindungen sind Poly-oxypropylenglykolmono-äther und die entsprechenden Diäther. ' ; "in which the radicals R ^, R and Rg are hydrogen or Ö ^ ö ^ groups bind and in which no more than two of these groups are hydrogen and η 'is an integer greater than 1 * Particularly valuable compounds are polyoxypropylene glycol monoethers and the corresponding Dieter. ';"
Die thermische Stabilität solcher Diester/Polyoxyalkylenglykoläther kann verbessert werden, wenn ein geringer Anteil Komplexester, der von drei oder mehr Carbonsäuren oder Alkoholen abstammt, wobei wenigstens zwei derselben difunktionelle Säuren oder Alkohole sind, einbringt. Solche Korn·* plexester können Glykol- oder Dicarbonsäure zentriert sein, wobei das Molekülendständig eine Mono-hydroxy- oder Mono-The thermal stability of such diesters / polyoxyalkylene glycol ethers can be improved if a small percentage Complex ester of three or more carboxylic acids or Alcohols, at least two of which are difunctional Acids or alcohols are, brings in. Such granular esters can be glycolic or dicarboxylic acid centered, where the molecule is terminally a mono-hydroxy or mono-
■ „-T1-309822/1098■ "-T1-309822 / 1098
carbonsäureverbindung aufweist. Ein besonders bevorzugter Komplexester dieser Art stammt von einem Polyäthylenglykol mit einem Molekulargewicht von 200, 2 Molekülen Sebazin- oder Azelainsäure und 2 Moleküle eines Oc-O-jq verzweigtkettigen aliphatischen einwertigen Alkohol- besonders 2- : Äthylhexanol, ab. -having carboxylic acid compound. A particularly preferred complex ester of this type is derived from a polyethylene glycol with a molecular weight of 200, 2 molecules of sebacic or azelaic acid and 2 molecules of an Oc-O-jq branched-chain aliphatic monohydric alcohol, especially 2- : ethylhexanol. -
Zu weiteren Zusätzen, die in dem Schmieröl verwendet werden, können gehören Korrosionsinhibitoren, z.B. Sebazinsäure, ein Metalldeaktivator, wie Chinizarin, ein Schauminhibitor, ZoB. Silikonpolymerisat, wie Dimethylsilikon, ein Antioxidationsmittel, z.B. Phenothiazin oder Dioctyldiphenylamin oder ein gleityerbesserndes Additiv, z.B. Tricresylphosphat. Es kann auch das Gemisch der Aminsalze bei einem flüssigen Brennstofföl, z.B. bei einem Dieselöl, verwendet werden*Other additives that can be used in the lubricating oil include corrosion inhibitors such as sebacic acid, a metal deactivator, such as quinizarine, a foam inhibitor, ZoB. Silicone polymer, such as dimethyl silicone, an antioxidant such as phenothiazine or dioctyldiphenylamine or a slip enhancing additive such as tricresyl phosphate. It can also be the mixture of amine salts with a liquid fuel oil, e.g. with a diesel oil, be used*
Tetrabutylammoniumsalze der Gemische von (1) Methyldihydrogenphosphat und Di-methylhydrogenphosphat (2) Äthyldihydrogenphosphat und Di-äthylhydrogenphosphat und (.3) n-Butyldihydrogenphosphat und Di-n-butylhydrogenphosphat wurden nach dem folgenden Verfahren hergestellt.Tetrabutylammonium salts of mixtures of (1) methyl dihydrogen phosphate and dimethyl hydrogen phosphate (2) ethyl dihydrogen phosphate and diethyl hydrogen phosphate and (.3) n-butyl dihydrogen phosphate and di-n-butyl hydrogen phosphate were produced by the following procedure.
Man rührte eine 10$ige wäßrige Lösung des sauren Phosphats und gab Tetra-n-butylammoniumhydroxidlösung (40%ig, wäßrig) zur Einstellung des p„-Wertes auf 7 zu, und verdampfte dieA 10 $ aqueous solution of the acidic phosphate was stirred and gave tetra-n-butylammonium hydroxide solution (40%, aqueous) to adjust the p "value to 7, and evaporated the
-12-309822/Ί098 -12-309822 / Ί098
Lösung zur Trockne in Gegenwart einer Spurenmenge von n-Octanol zur Inhibierung der Schaumbildung. Man gab dann Toluol zu und verdampfte die Lösung wiederum zur Trooknef dies wiederholte man nocheinmal um ein wasserfreies Produkt sicherzustellen.Solution to dryness in the presence of a trace amount of n-octanol to inhibit foaming. Then one gave Toluene and the solution evaporated again to Trooknef this was repeated once more to ensure an anhydrous product.
Zu Vergleichszwecken wurden ebenso Tetrabutylammoniumsalze der Gemische von 05-» Cg- und C.g-^-Alkyldihydrogen- und Di-n-alkylhydrogenphosphaten hergestellt.Tetrabutylammonium salts were also used for comparison the mixtures of 05- »Cg- and C.g - ^ - alkyl dihydrogen and Di-n-alkyl hydrogen phosphates produced.
Jedes Gemisch wurde getrennt einem synthetischen öl auf Esterbasis zugegeben, das weiterhin 1,0 Gew.$ Tricresylphosphat, 1,6 Gew.$ Dioctyldiphenylamin und 0,4 &ew»# Phenothiazin enthielt. Das Basisöl war ein Gemisch von Estern, die durch Veresterung von 90 Gew.$ Pentaerythrit und 10 ßew.? Dipentaerythrit mit einem Gemisch von (Oc-GgJ-Fettsäuren erhalten wurden. ·Each mixture was separately based on a synthetic oil Ester base added, which also contains 1.0% by weight of tricresyl phosphate, 1.6% by weight of dioctyldiphenylamine and 0.4% by weight of phenothiazine contained. The base oil was a mixture of esters obtained by esterifying 90% by weight of pentaerythritol and 10% by weight. Dipentaerythritol obtained with a mixture of (Oc-GgJ fatty acids became. ·
Es wurden die IAE-Getriebebruchbelastung bei 110°C/2000 Upm und die Rolls-Royce-Elastomeraufquelltemperatur vom IuIIr punkt (in 0C) ermittelt. Die Standard-Rolls-·Royse-Untersuchung der Silikonelastomerverträglichkeit (Verfahren IOO9) beinhaltet das 192 stundenlange Eintauchen eines Standardversuchprobestücks in 50 ml des unter Versuoh stehenden . Schmiermittels bei einer Temperatur von 175°C. öle mit Hochdruckeigenschaften können nicht so hergestellt werden, daß sie mit Elastomeren unter diesen Bedingungen unverändert verträglich sind, und es wurden daher nach einer ModifizierThe IAE transmission fracture load at 110 ° C / 2000 rpm and the Rolls-Royce elastomer swelling temperature from the IUIIr point (in 0 C) were determined. The standard Rolls- Royse investigation of the silicone elastomer compatibility (method IOO9) involves immersing a standard test specimen in 50 ml of the Versuoh for 192 hours. Lubricant at a temperature of 175 ° C. Oils with extreme pressure properties cannot be produced in such a way that they are still compatible with elastomers under these conditions, and a modification has therefore been made
309822/1098 -13-,309822/1098 -13-,
rung dieses Verfahrens Versuchsreihen bei unterschiedlichen Temperaturen durchgeführt und der Prosentsatz des Aufquellens des Elastomers gegen die Temperatur aufgetragen« Die extrapolierte Temperatur, bei der das Auf quellen '* vom Nullstand eintritt, wird als Index der Elastomerverträglichkeit des Öls bezeichnet. Die Ergebnisse sind der nachfolgenden Tabelle zu entnehmen. Es ist zu erkennen, daß die besten Ergebnisse im Hinblick auf die Hochdruckeigenschaften dann erhalten werden, wenn Tetrabutylammoniumsalze der Di-methylhydrogen- und Methyldihydrogenphosphate verwendet werden, und daß die Hochdruckeigenschaften schnell in dem Maße abfallen, wie die Kettenlänge der Gruppen R und R in dem Phosphat zunimmt-.tion of this procedure series of tests with different Temperatures performed and the percentage of swelling of the elastomer plotted against the temperature «The extrapolated temperature at which the swelling '* occurs from the zero level is used as the index of the elastomer compatibility of the oil. The results are shown in the table below. It can be seen that the best Results in terms of the extreme pressure properties then obtained when tetrabutylammonium salts of the dimethylhydrogen and methyl dihydrogen phosphates are used, and that the high pressure properties decrease rapidly as the chain length of the groups R and R in that Phosphate increases-.
309822/1098309822/1098
Kohlenstoff-Kettenläage
in dem
sauren Phosphatgemisch Carbon chain layer in that
acidic phosphate mixture
Konzentration IAE-Getriebe-Concentration of IAE transmission
Gew.# P Gew.$ (Arcinsalz) Bruchbelastung - 2000 Upm/110°0 Weight # P Weight $ (Arcin salt) breaking load - 2000 rpm / 110 ° 0
1010
' 10'10
1010
1010
1010
7 x 107 x 10
5 x 105 x 10
-2 -2 -2 -2 -2 -3 -3-2 -2 -2 -2 -2 -3 -3
0,19 0,17 0,1.5 0,10 0,070.19 0.17 0.1.5 0.10 0.07
R.E.-Silikonelastomer Hull-Aufiiuellung gem. rc) ' RE silicone elastomer Hull filling according to rc) '
135 132 125135 132 125
120 125 130120 125 130
AJlAJl
Beispiel 2 ■.."-_■-.". Example 2 ■ .. "-_ ■ -.".
Hexyl trio et ylammoniumsalze von Gemischen von Methyldi^ hydrogenphosphat und Dime thylhydrogenphosphat warden nach dem Verfahren von Beispiel T hergestellt, ausgenommen, daß Hexyltrioctylaimaoniumhydroxidlösung (4®$, wäßrig) anstelle von Tetra-n-liutylammoniumhydroxid verwendet wurde.Hexyl trio et ylammonium salts of mixtures of methyldi ^ hydrogen phosphate and dimethyl hydrogen phosphate are added prepared according to the procedure of Example T, except that Hexyltrioctylaimaoniumhydroxidlösung (4® $, aqueous) instead of tetra-n-liutylammonium hydroxide was used.
0,125 Gew.% ("bezogen auf das Gewicht <äes Schmieröls) wurden· den gemischten Hexyltrioctylammoniumsalzen zugegeben, wobei das gleiche Basisöl wie in Beispiel Ί verwendet wurde, das die gleichen Mengen wie Tricresylphosjphat, Dioctyldiphenylamin und Phenothiazin enthielt.0.125 wt.% ( "Weight <äes lubricating oil) were mixed Hexyltrioctylammoniumsalzen · added, using the same base oil as used in Example Ί containing the same amounts as Tricresylphosjphat, dioctyldiphenylamine and phenothiazine.
V/enn diese Sciniierölzubereitung den liE-Getriebe- und Eolls-Royce-Silikonelastomer-Untersuelrangen unterworfen wurden, erhielt man folgende Ergebnisse: IAE-Getriebebruchbelastung 2000 Upm/iiO^C - 4,309 kgV / hen this Sciniierölpreparation the liE gear and Subjected to Eolls-Royce silicone elastomer sub-rods the following results were obtained: IAE gear breakage load 2000 rpm / 10 ^ C - 4.309 kg
Rolls-Hoyce-Silikonelastomer-lfiall- :Rolls-Hoyce-silicone-elastomer-lfiall-:
aufquellraag . — 125°Gaufquellraag. - 125 ° G
Patentansprüche; 309022/1098 -16- Claims; 309022/1098 -16-
Claims (7)
Reste R und R gleich und vorzugsweise beide Methylgrup-5 6
R and R residues are the same and preferably both methyl groups
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB5457771A GB1392600A (en) | 1971-11-24 | 1971-11-24 | Lubricating oil compositions |
Publications (1)
Publication Number | Publication Date |
---|---|
DE2257708A1 true DE2257708A1 (en) | 1973-05-30 |
Family
ID=10471463
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2257708A Ceased DE2257708A1 (en) | 1971-11-24 | 1972-11-24 | OIL PREPARATIONS |
Country Status (4)
Country | Link |
---|---|
US (1) | US3859218A (en) |
DE (1) | DE2257708A1 (en) |
FR (1) | FR2160992B1 (en) |
GB (1) | GB1392600A (en) |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1486197A (en) * | 1973-09-29 | 1977-09-21 | Nippon Light Metal Res Labor | Water-soluble metal working lubricating composition |
US3979308A (en) * | 1974-03-27 | 1976-09-07 | Texaco Inc. | Lubricant compositions with improved viscosity index |
US3951829A (en) * | 1975-05-05 | 1976-04-20 | Cities Service Company | Two-cycle and rotary combustion engine lubricant |
GB1583873A (en) * | 1976-05-05 | 1981-02-04 | Exxon Research Engineering Co | Synthetic lubricating oil composition |
US4514311A (en) * | 1983-05-09 | 1985-04-30 | Texaco Inc. | Wear-resistant aircraft engine lubricating oil |
US4778610A (en) * | 1985-12-27 | 1988-10-18 | Mobil Oil Corporation | Acid phosphites as multifunctional additives and compositions thereof |
JPH01279998A (en) * | 1987-12-09 | 1989-11-10 | Exxon Res & Eng Co | Improved engine lubricant |
US5348561A (en) * | 1990-03-01 | 1994-09-20 | Exxon Chemical Patents Inc. | Fuel oil compositions |
JPH05331481A (en) * | 1992-05-29 | 1993-12-14 | Tonen Corp | Lubricant composition for two-cycle engine |
US5422023A (en) * | 1993-10-12 | 1995-06-06 | Exxon Research And Engineering Company | Corrosion inhibitor for aviation turbine oils (PNE-628) |
US5587355A (en) * | 1995-12-22 | 1996-12-24 | Exxon Research And Engineering Company | High load-carrying turbo oils containing amine phosphate and thiophene carboxylic acid derivatives |
US5679627A (en) * | 1995-12-22 | 1997-10-21 | Exxon Research & Engineering Company | High-load carrying turbo oils containing amine phosphate and a sulfur containing carboxylic acid (law348) |
US5582760A (en) * | 1995-12-22 | 1996-12-10 | Exxon Research And Engineering Company | High load-carrying turbo oils containing amine phosphate and alkylthiosuccinic acid |
US5801130A (en) * | 1995-12-22 | 1998-09-01 | Exxon Research And Engineering Company | High load-carrying turbo oils containing amine phosphate and dimercaptothiadiazole derivatives |
US5750478A (en) * | 1995-12-22 | 1998-05-12 | Exxon Research And Engineering Company | High load-carrying turbo oils containing amine phosphate and sulfurized fatty acid |
US5585029A (en) | 1995-12-22 | 1996-12-17 | Exxon Research And Engineering Company | High load-carrying turbo oils containing amine phosphate and 2-alkylthio-1,3,4-thiadiazole-5-alkanoic acid |
US6001778A (en) * | 1996-10-01 | 1999-12-14 | J. Morita Manufacturing Corporation | Lubricating oil for rolling bearing in high-speed rotating equipment, and bearing lubricated with the same lubricating oil |
US7124728B2 (en) * | 2003-01-24 | 2006-10-24 | Exxonmobil Research And Engineering Company | Modification of lubricant properties in an operating all loss lubricating system |
US7598212B2 (en) * | 2003-07-18 | 2009-10-06 | Exxonmobil Research And Engineering Company | Lubricating composition suitable for diesel engines |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2563506A (en) * | 1951-08-07 | Quaternary ammonium salts of | ||
BE759166A (en) * | 1969-06-25 | 1971-05-19 | Exxon Research Engineering Co | LUBRICATING OIL COMPOSITION |
-
1971
- 1971-11-24 GB GB5457771A patent/GB1392600A/en not_active Expired
-
1972
- 1972-11-15 US US306850A patent/US3859218A/en not_active Expired - Lifetime
- 1972-11-23 FR FR7241618A patent/FR2160992B1/fr not_active Expired
- 1972-11-24 DE DE2257708A patent/DE2257708A1/en not_active Ceased
Also Published As
Publication number | Publication date |
---|---|
US3859218A (en) | 1975-01-07 |
GB1392600A (en) | 1975-04-30 |
FR2160992B1 (en) | 1978-10-27 |
FR2160992A1 (en) | 1973-07-06 |
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