DE1243811B - Lubricant additives - Google Patents

Lubricant additives

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Publication number
DE1243811B
DE1243811B DEF43191A DEF0043191A DE1243811B DE 1243811 B DE1243811 B DE 1243811B DE F43191 A DEF43191 A DE F43191A DE F0043191 A DEF0043191 A DE F0043191A DE 1243811 B DE1243811 B DE 1243811B
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DE
Germany
Prior art keywords
oil
carbodiimide
diphenyl
tetraisopropyl
diphenylcarbodiimide
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
DEF43191A
Other languages
German (de)
Inventor
Dr Wolfram Neumann
Dr Walther Lohmar
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.)
Bayer AG
Original Assignee
Bayer AG
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Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Priority to DEF43191A priority Critical patent/DE1243811B/en
Priority to US455606A priority patent/US3346496A/en
Priority to BE665202A priority patent/BE665202A/xx
Priority to GB24765/65A priority patent/GB1049618A/en
Priority to FR20482A priority patent/FR1437094A/en
Priority to NL656507710A priority patent/NL144982B/en
Publication of DE1243811B publication Critical patent/DE1243811B/en
Pending legal-status Critical Current

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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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—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
    • C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—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
    • C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
    • 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
    • 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
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/086—Imides
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/14—Containing carbon-to-nitrogen double bounds, e.g. guanidines, hydrazones, semicarbazones
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/221—Six-membered rings containing nitrogen and carbon only
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/226—Morpholines
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/28—Amides; Imides
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/30—Heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives

Description

BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY

DEUTSCHESGERMAN

PATENTAMTPATENT OFFICE

AUSLEGESCHRIFTEDITORIAL

Int. Cl.:Int. Cl .:

ClOmClOm

CIOM 169/oOB 26CIOM 169 / oOB 26

Deutsche Kl.: 23 c-1/01 German class: 23 c -1/01

Nummer:
Aktenzeichen:
Anmeldetag:
Auslegetag:Number:
File number:
Registration date:
Display day:

1243 811
F43191IVc/23c
16.Juni 1964
6. Juli 19671243 811
F43191IVc / 23c
June 16, 1964
July 6, 1967

Es wurde gefunden, daß sich als Schmierstoffzusatzmittel mit hervorragendem Erfolg Carbodiimide verwenden lassen.It has been found that as lubricant additives have had carbodiimides used with excellent success.

Als Carbodiimide kommen Mono- und Polycarbodiimide in Betracht; sie können der aliphatischen, cycloaliphatischen und aromatischen Reihe angehören. Von den Monocarbodiimiden seien beispielsweise genannt: Diisopropyl-carbodiimid, Di-n-butyl-carbodiimid, Methyl-tert.-butyl-carbodiimid, Dicyclobexylcarbodiimid, Diphenyl-carbodiimid, Di-p-tolyl-carbodiimid und 4,4'-Didodecyl-diphenyl-carbodiimid; als besonders vorteilhaft haben sich Diphenyl-monocarbodiimide erwiesen, die in den Phenylresten in Orthostellung zur Carbodiimidgruppe Substituenten, z. B. Alkyl-, Alkoxy-, Aryl- und Aralkylreste, tragen, wie 2,2'-Diäthyl-diphenyl-carbodiimid, 2,2'-Diisopropyl - diphenyl - carbodiimid, 2,2' - Diäthoxy - diphenyl carbodiimid, 2,6,2',6'-Tetraäthyl-diphenyl-carbodiimid, 2,6,2',6'-Tetraisopropyl-diphenyl-carbodiimid, 2,6,2',6'-Tetraäthyl-3,3'-dichlor-diphenyl-carbodiimid, 2,2'-Diäthyl-6,6'-dichlor-diphenyl-carbodiimid, 2,6, 2',6'-Tetraisobutyl-3,3'-dinitro-diphenyl-carbodiimid und 2,4,6,2',4',6' - Hexaisopropyl - diphenyl -carbodiimid. Von den Polycarbodiimiden kommen beispielsweise in Betracht Tetramethylen-w,a/-bis-(tert.-butylcarbodiimid), Hexamethylen-w,(o'-bis-(tert.-butyl-carbodiimid), Tetramethylen-oj,c/-bis-(phenyl-carbodiimid) sowie die Verbindungen, die durch Erhitzen von aromatischen Polyisocyanaten, wie 1,3-Diisopropylphenylen-2,4-diisocyanat, l-MethyW^-diäthyl-phenylen-2,4-diisocyanat und 3,5,3',5'-Tetraisopropyl-diphenylmethan-4,4-diisocyanat, in Gegenwart von tertiären Aminen, basisch reagierenden Metallverbindungen, carbonsauren Metallsalzen oder nichtbasischen Organmetallverbindungen bei einer Temperatur von mindestens 12O0C gemäß dem Verfahren des deutschen Patents 1156 401 erhältlich sind.Suitable carbodiimides are mono- and polycarbodiimides; they can belong to the aliphatic, cycloaliphatic and aromatic series. Examples of the monocarbodiimides are: diisopropyl-carbodiimide, di-n-butyl-carbodiimide, methyl-tert-butyl-carbodiimide, dicyclobexyl-carbodiimide, diphenyl-carbodiimide, di-p-tolyl-carbodiimide and 4,4'-didodecyl-diphenyl-diphenyl -carbodiimide; Diphenyl monocarbodiimides have proven to be particularly advantageous which have substituents in the phenyl radicals in the ortho position to the carbodiimide group, e.g. B. alkyl, alkoxy, aryl and aralkyl radicals, such as 2,2'-diethyl-diphenyl-carbodiimide, 2,2'-diisopropyl-diphenyl-carbodiimide, 2,2'-diethoxy-diphenyl carbodiimide, 2, 6,2 ', 6'-tetraethyl-diphenyl-carbodiimide, 2,6,2', 6'-tetraisopropyl-diphenyl-carbodiimide, 2,6,2 ', 6'-tetraethyl-3,3'-dichloro-diphenyl -carbodiimide, 2,2'-diethyl-6,6'-dichloro-diphenyl-carbodiimide, 2,6, 2 ', 6'-tetraisobutyl-3,3'-dinitro-diphenyl-carbodiimide and 2,4,6, 2 ', 4', 6 '- hexaisopropyl-diphenyl-carbodiimide. Examples of polycarbodiimides include tetramethylene-w, a / -bis- (tert-butylcarbodiimide), hexamethylene-w, (o'-bis- (tert-butyl-carbodiimide), tetramethylene-oj, c / -bis - (phenyl-carbodiimide) and the compounds obtained by heating aromatic polyisocyanates such as 1,3-diisopropylphenylene-2,4-diisocyanate, l-methyW ^ -diethylphenylene-2,4-diisocyanate and 3,5,3 ', 5'-Tetraisopropyl-diphenylmethane-4,4-diisocyanate, in the presence of tertiary amines, basic metal compounds, carboxylic acid metal salts or non-basic organ metal compounds at a temperature of at least 12O 0 C according to the method of the German patent 1156 401 are available.

Mit Hilfe der Carbodiimide gelingt es, Schmiermittel der verschiedensten Art wesentlich zu verbessern, insbesondere in ihrer Widerstandsfähigkeit gegenüber oxydativen Angriffen. Dies gilt vor allem für Schmiermittel, die aus Mineralölen bereitet sind, sowie für Schmieröle synthetischer Herkunft, welche Polyäther oder Polyätherester sind, insbesondere für Schmieröle auf der Grundlage von synthetischen PoIyäthern oder Polyätherestern, welche — (CH2)4-O-Gruppen in mehrfachem Wechsel miteinander oder mit anderen Alkylen-O-Gruppen enthalten und beispielsweise in dem deutschen Patent 1 071 872 beschrieben sind. Gleichzeitig wirken die Carbodiimide auch als Korrosionsschutzmittel, und außerdem halten sie Abbauprodukte, die sich beim Schmiervorgang SchmierstoffzusatzmittelWith the help of the carbodiimides it is possible to improve lubricants of the most varied of types significantly, especially in terms of their resistance to oxidative attacks. This applies in particular to lubricants made from mineral oils, as well as to lubricating oils of synthetic origin, which are polyethers or polyether esters, in particular for lubricating oils based on synthetic polyethers or polyether esters which have multiple - (CH 2 ) 4 -O groups Alternations with one another or with other alkylene-O groups and are described, for example, in German Patent 1,071,872. At the same time, the carbodiimides also act as a corrosion protection agent, and they also hold the breakdown products that are produced during the lubrication process as lubricant additives

Anmelder:Applicant:

Farbenfabriken Bayer Aktiengesellschaft,Paint factories Bayer Aktiengesellschaft,

LeverkusenLeverkusen

Als Erfinder benannt:Named as inventor:

Dr. Wolfram Neumann,Dr. Wolfram Neumann,

Dr. Walther Lohmar, LeverkusenDr. Walther Lohmar, Leverkusen

bilden, in Lösung. Die jeweils erforderlichen Mengen an Carbodiimiden lassen sich durch Vorversuche leicht ermitteln; im allgemeinen erweisen sich Zusätze von 1 bis 2 Gewichtsprozent, bezogen auf das Schmiermittel, als ausreichend.form, in solution. The amounts of carbodiimides required in each case can easily be determined by preliminary tests determine; In general, additions of 1 to 2 percent by weight, based on the lubricant, prove to be as sufficient.

Bemerkenswert ist, daß die erfindungsgemäß zu verwendenden Schmierstoffzusatzmittel mit anderen Schmierstoffzusätzen, z. B. mit Detergentien, Mitteln zur Erhöhung der Schmiernlmfestigkeit sowie Mitteln zur Verbesserung des Stockpunktes und der Viskosität, verträglich sind. Eine besonders vorteilhafte Ausführungsform der vorliegenden Erfindung besteht darin, daß man den Schmierstoffen die Carbodiimide in Kombination mit als Alterungsschutzmitteln bekannten Diphenylaminen, wie 4,4'-Di-(methylbenzyl)-diphenylamin, und/oder Hydroxychinolinen, wie 8-Hydroxychinolin, zusetzt. Man erzielt so überraschenderweise einen synergistischen Effekt.It is noteworthy that the to be used according to the invention Lubricant additives with other lubricant additives, e.g. B. with detergents, agents to increase smear resistance and agents to improve the pour point and the viscosity, are compatible. A particularly advantageous embodiment of the present invention is that the lubricants the carbodiimides in Combination with diphenylamines known as anti-aging agents, such as 4,4'-di- (methylbenzyl) -diphenylamine, and / or hydroxyquinolines, such as 8-hydroxyquinoline, are added. This is surprisingly achieved a synergistic effect.

Die in den folgenden Beispielen angegebenen Teile sind Gewichtsteile.The parts given in the following examples are parts by weight.

Beispiel 1example 1

100 Teile eines naphthenbasischen Mineralöles werden mit 1 Teil 2,6,2',6'-Tetraisopropyl-diphenyl-carbodiimid versetzt. Die Widerstandsfähigkeit des Mineralöles gegenüber oxydativen Angriffen wird auf diese Weise erheblich verbessert; die Wirkung des angewandten Carbodiimids wird durch Zusatz von 0,2 Teilen 4,4'-(Dimethylbenzyl)-diphenylamin oder/und 8-Hydroxychinolin noch erhöht. Dies geht aus einschlägigen Vergleichsversuchen hervor, deren Ergebnisse in der Tabelle I wiedergegeben sind, in der die Neutralisationszahlen (mg KOH/g öl) der mit den verschiedenen Zusätzen versehenen öle nach oxydativer Einwirkung aufgeführt sind.
In der Tabelle bedeutet
A = Öl ohne Zusatz;
,50 B = Öl mit 1 % 2,6,2',6'-Tetraisopropyl-diphenyl-100 parts of a naphthenic mineral oil are mixed with 1 part of 2,6,2 ', 6'-tetraisopropyl-diphenyl-carbodiimide. The resistance of the mineral oil to oxidative attacks is considerably improved in this way; the effect of the applied carbodiimide is increased by adding 0.2 parts of 4,4 '- (dimethylbenzyl) diphenylamine and / or 8-hydroxyquinoline. This is evident from relevant comparative tests, the results of which are shown in Table I, in which the neutralization numbers (mg KOH / g oil) of the oils provided with the various additives are listed after oxidative action.
In the table means
A = oil without additives;
, 50 B = oil with 1% 2,6,2 ', 6'-tetraisopropyl-diphenyl-

carbodiimid;
C = öl mit 0,2 °/o 4,4'-Dimethylbenzyldiphenylamin;carbodiimide;
C = oil with 0.2% 4,4'-dimethylbenzyldiphenylamine;

709 609/400709 609/400

Claims (1)

D = Ol mit 1% 2,6,2',6'-Tetraisopropyl-diphenylcarbodiimid und 0,2% 4,4'-Dimethylbenzyldiphenylamin; D = oil with 1% 2,6,2 ', 6'-tetraisopropyl-diphenylcarbodiimide and 0.2% 4,4'-dimethylbenzyldiphenylamine; E = öl mit 1 % 2,6,2',6'-Tetraisopropyl-diphenylcarbodiimid und 0,2% 8-HydroKychinolin:E = oil with 1% 2,6,2 ', 6'-tetraisopropyl-diphenylcarbodiimide and 0.2% 8-hydroquinoline: F = Öl mit 0,2% 4,4'-DimethylbenzyldiphenylaminF = oil with 0.2% 4,4'-dimethylbenzyldiphenylamine und 0,2% 8-Hydroxychinolin;
G = öl mit 1 % 2,6,2',6'-Tetraisopropyl-diphenyI-and 0.2% 8-hydroxyquinoline;
G = oil with 1% 2,6,2 ', 6'-tetraisopropyl-diphenyl- carbodiimid, 0,2% 4,4'-Dimethylbenzyldiphe-carbodiimide, 0.2% 4,4'-dimethylbenzyldiphe- nylamiu und 0,3% 8-Hydroxychinolin.nylamiu and 0.3% 8-hydroxyquinoline. Tabelle 1Table 1 Dauer der oxydativenDuration of the oxidative A ,A, \\ BB. CC. NeutralisationszahlenNeutralization numbers EE. , F, F GG Einwirkung in StundenExposure in hours 0,070.07 II. 0,050.05 0,080.08 i D i D 0,120.12 0,140.14 0,100.10 00 2,882.88 0,200.20 0,400.40 0,050.05 0,040.04 0,070.07 0,060.06 5050 0,340.34 0,660.66 0,160.16 0,020.02 0,120.12 0,080.08 100100 0,700.70 1,061.06 0,240.24 0,160.16 ; 0,25; 0.25 0,090.09 200200 1,001.00 1,551.55 I 0,24I 0.24 0,200.20 ! 0,43! 0.43 0,110.11 300300 1,391.39 2,482.48 ; 0.80; 0.80 0,280.28 0,650.65 0,160.16 400400 1,921.92 ' 1,20 .'1.20. 0,570.57 , 0,99 ', 0.99 ' 0,300.30 500500 3,103.10 1,431.43 2,462.46 M7M7 0,540.54 600600 1.601.60 1,401.40 0,860.86 700700 1 1,79 1 1.79 ' 1,60'1.60 1,061.06 800800 1,891.89 1,79 :1.79: 1.191.19 900900 1.971.97 1,96 j1.96 y 1,251.25 10001000 2,202.20
Zur Durchführung der Vergleichsversuche wurden entsprechend der Vorschrift des ASTM-Oxydationstests D 943-54 jeweils 300 ml des zu untersuchenden Öles zusammen mit 60 ml destilliertem Wasser in einen 60 cm hohen Glaszylinder von 4,5 cm Durchmes>er eingefüllt, und in das Öl-Wasser-Gemisch wurden in Anlehnung an die bei den Schmiervorgängen herrschenden Bedingungen Eisen- und Kiipferspiralen eingebracht. Durch ein Rohr, das fast bis zum Boden des Prüfzylinders reichte, wurden dann bei 95: C stündlich 3 1 Sauerstoff durch das Öl-Wasscr-Gemisch geblasen. In bestimmten Zeitabständen wurden 10 ml des Öles zur Bestimmung der Nciitralisationszahl entnommen. Wenn die Neutralisationszahl einen Wert über 2 erreicht hatte oder wenn die Dauer der oxydativen t inwirkung 1000 Stunden betragen hatte, wurde die Prüfung abgebrochen.To carry out the comparative tests, in accordance with the ASTM oxidation test D 943-54, 300 ml of the oil to be examined were poured into a 60 cm high glass cylinder with a diameter of 4.5 cm, together with 60 ml of distilled water, and the oil Water mixture, iron and copper spirals were introduced based on the conditions prevailing during the lubrication processes. Then 3 liters of oxygen per hour were blown through the oil-water mixture through a tube which reached almost to the bottom of the test cylinder at 95 : C. At certain time intervals, 10 ml of the oil were removed to determine the nitralization number. If the neutralization number had reached a value above 2 or if the duration of the oxidative action was 1000 hours, the test was terminated. Beispiel 2Example 2 100 Teile eines Polyathcrölcs, welches gemäß Beispiel 2 der deutschen Patentschrift 1 120 139 durch Polymerisation eines Gemisches aus Tetrahydrofuran, Äthylenoxyd und Propylenoxyd in Gegenwart von Formaldehyddimethylacetat und Bortrirluoridverbindungen des Tetrahydrofurans hergestellt war, werden mit 2 Teilen eines der in der Tabellen angeführten Zusatzmittels versetzt. Aus den dortigen Neutralisationszahlen, die gemäß den im Beispiel I gemachten Angaben ermittelt wurden, geht hervor, daß auf diese Weise die Widerstandsfähigkeit des Öles gegenüber oxydativen Einflüssen ebenfalls beträchtlich verbessert werden kann.100 parts of a Polyathcrölcs, which according to Example 2 of German patent specification 1 120 139 by polymerizing a mixture of tetrahydrofuran, Ethylene oxide and propylene oxide in the presence of formaldehyde dimethyl acetate and boron fluoride compounds of tetrahydrofuran was prepared, 2 parts of one of the tables listed Additive added. From the neutralization numbers there, which are made in accordance with those in Example I. Information has been determined, it can be seen that in this way the resistance of the oil to oxidative influences can also be improved considerably. In der Tabelle bedeutet
A -■ Öl ohne Zusalzmiüel;
B -- Öl mit 2% Di-n-butyl-carbodiimid;
C -- Öl mit 2% Di-cyelohexyl-carbodiimid;
D ^= Öl mit 2'V0 2,6.2'.6'-Tetraäthyl-4,4'-dimethyl-In the table means
A - ■ Oil without additives;
B - oil with 2% di-n-butyl-carbodiimide;
C - oil with 2% di-cyelohexyl-carbodiimide;
D ^ = oil with 2'V 0 2,6.2'.6'-tetraethyl-4,4'-dimethyl- diphenyl-carbodiimid:
E ---- Öl mit 2°,o 2.6.2',e'-Tetraäthyl-diphenyl-carbo-diphenyl carbodiimide:
E ---- oil with 2 °, o 2.6.2 ', e'-tetraethyl-diphenyl-carbo- diimid;diimide; F =-■ Öl mit 2% 2,6,2',6'-Teiraisopiopyl-diphenylcarbodiimid. F = - ■ Oil with 2% 2,6,2 ', 6'-teiraisopiopyl-diphenylcarbodiimide. Tabelle IITable II D;uter der o\\dalnen
Einwirk'jtiii in SiumienD; uter der o \\ thalnen
Influence in Siumia Neutral i
C Neutral i
C. 50
100
200
300
400
500
600
700
800
900
100050
100
200
300
400
500
600
700
800
900
1000 Verwendung von Carbodiimiden als Schmierstoffzusatzmittel, gegebenenfalls in Kombination mit als Alterungsschutzmittel bekannten Diphenylaminen und/oder Hydroxychinolinen.Use of carbodiimides as lubricant additives, optionally in combination with as Antioxidants known diphenylamines and / or hydroxyquinolines. 0.020.02 0.000.00 0,000.00 0.010.01 0.010.01 0.030.03 0,20.2 0.000.00 0.000.00 0.010.01 1 0,01 1 0.01 0,030.03 0,580.58 0.000.00 0,000.00 0,010.01 0,010.01 0,030.03 1,351.35 0.010.01 0.000.00 0,010.01 0,010.01 0.030.03 1/-71 / -7 0,(i60, (i6 0,000.00 0,020.02 0.010.01 0.050.05 2,502.50 0,150.15 0,000.00 0,050.05 0,OL0, OL 0,120.12 0,210.21 0.030.03 : 0,15 : 0.15 0,010.01 0,200.20 0,290.29 0.080.08 0.340.34 0,020.02 0,280.28 0,380.38 0,140.14 0.580.58 0,120.12 0.360.36 i 0,48i 0.48 0,210.21 0,900.90 0,300.30 0,470.47 0,530.53 0,290.29 0.950.95 I 0,54I 0.54 0,490.49 0.530.53 0,390.39 0,950.95 I 0,84I 0.84 0,490.49 Patentanspruch:Claim:
DEF43191A 1964-06-16 1964-06-16 Lubricant additives Pending DE1243811B (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
DEF43191A DE1243811B (en) 1964-06-16 1964-06-16 Lubricant additives
US455606A US3346496A (en) 1964-06-16 1965-05-13 Lubricants containing carbodiimides as antioxidants
BE665202A BE665202A (en) 1964-06-16 1965-06-10
GB24765/65A GB1049618A (en) 1964-06-16 1965-06-11 Lubricants
FR20482A FR1437094A (en) 1964-06-16 1965-06-11 Lubricant additives
NL656507710A NL144982B (en) 1964-06-16 1965-06-16 PROCESS FOR PREPARING LUBRICANTS.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF43191A DE1243811B (en) 1964-06-16 1964-06-16 Lubricant additives

Publications (1)

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DE1243811B true DE1243811B (en) 1967-07-06

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DEF43191A Pending DE1243811B (en) 1964-06-16 1964-06-16 Lubricant additives

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US (1) US3346496A (en)
BE (1) BE665202A (en)
DE (1) DE1243811B (en)
FR (1) FR1437094A (en)
GB (1) GB1049618A (en)
NL (1) NL144982B (en)

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US3944492A (en) * 1966-04-07 1976-03-16 Uniroyal, Inc. Lubricant compositions containing N-substituted naphthylamines as antioxidants
US3666716A (en) * 1966-04-07 1972-05-30 Uniroyal Inc Derivatives of diphenylamine and the phenylnaphthylamines as antioxidants and as synergists with dialkyl 3,3{40 -thiodipropionates
US4346015A (en) * 1979-02-21 1982-08-24 Union Carbide Corporation Method of improving antiwear properties of high temperature hydrocarbon compositions
US4202784A (en) * 1979-04-09 1980-05-13 Standard Oil Company (Indiana) Tertiary carbinamine modified mannich compositions and lubricants containing same
US4392968A (en) * 1980-08-13 1983-07-12 Nippon Oil Company, Limited Metal deactivator and composition containing same
US4467395A (en) * 1983-02-25 1984-08-21 Sprague Electric Company AC Metallized capacitor and impregnant therefor
DE69421032T2 (en) * 1993-03-25 2000-02-03 Asahi Denka Kogyo Kk LUBRICANTS FOR REFRIGERATOR AND LUBRICANT COMPOSITION CONTAINING THEM
DE4435548A1 (en) * 1994-10-05 1996-04-11 Rhein Chemie Rheinau Gmbh Stabilized lubricant base substance
US6750182B1 (en) 1998-10-09 2004-06-15 Exxonmobil Research And Engineering Company Polar oil based industrial oils with enhanced sludge performance
US6143702A (en) * 1998-10-09 2000-11-07 Exxon Research And Engineering Company Lubricating oils of enhanced oxidation stability containing n-phenyl-naphthyl amines, or substituted derivatives of n-phenyl naphthyl amine and carbodiimide acid scavengers
US6235687B1 (en) * 1998-10-09 2001-05-22 Exxon Research And Engineering Company Method for producing lubrication oils possessing anti rust properties containing acidic anti rust additive and acid scavengers
GB2416172B (en) * 2004-07-13 2009-04-22 Alan Edwin Jemmett Rapeseed oil lubricant
US7456137B2 (en) * 2004-12-03 2008-11-25 Afton Chemical Corporation Compositions comprising at least one carbodiimide
US20060122077A1 (en) * 2004-12-03 2006-06-08 Bruce Wilburn Compositions comprising at least one carbodiimide
WO2008041492A1 (en) * 2006-09-29 2008-04-10 Idemitsu Kosan Co., Ltd. Lubricant for compression refrigerating machine and refrigerating apparatus using the same
GB0904900D0 (en) * 2009-03-21 2009-05-06 Taylor Russell This invention relates to the manufacture and application of an metal ion chelating composition that can be added to motor oil to improve performance of the
CA2908474C (en) 2013-04-02 2021-04-27 Brasscorp Limited Improved neutralization and removal of acids in hvac systems through the use of drying agents
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DE1074794B (en) * 1957-12-02 1960-02-04 Esso Research And Engineering Company, Elizabeth, N. J. (V. St. A.) Lubricating oil additive and mineral lubricating oils containing this additive
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Publication number Priority date Publication date Assignee Title
DE1543843B1 (en) * 1965-12-27 1972-04-27 Rhone Poulenc Sa 4,4'-bis- (alpha, alpha-dimethylbenzyl) -diphenylamine, its production and use as an anti-aging agent

Also Published As

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NL144982B (en) 1975-02-17
US3346496A (en) 1967-10-10
BE665202A (en) 1965-10-01
FR1437094A (en) 1966-04-29
GB1049618A (en) 1966-11-30

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