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DE1268299B - Schmieroel - Google Patents

Schmieroel

Info

Publication number
DE1268299B
DE1268299B DEP1268299A DE1268299A DE1268299B DE 1268299 B DE1268299 B DE 1268299B DE P1268299 A DEP1268299 A DE P1268299A DE 1268299 A DE1268299 A DE 1268299A DE 1268299 B DE1268299 B DE 1268299B
Authority
DE
Germany
Prior art keywords
bis
lubricating oil
butyl
tert
hydroxyphenyl
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
DEP1268299A
Other languages
English (en)
Inventor
Bobby Malone
George Nacson
Gedeminas Joseph Reinis
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.)
Shell Research Ltd
Original Assignee
Shell Research Ltd
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 Shell Research Ltd filed Critical Shell Research Ltd
Publication of DE1268299B publication Critical patent/DE1268299B/de
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
    • C07D207/408—Radicals containing only hydrogen and carbon atoms attached to ring carbon atoms
    • C07D207/412—Acyclic radicals containing more than six carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
    • 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
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
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    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/08—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic sulfur-, selenium- or tellurium-containing compound
    • C—CHEMISTRY; METALLURGY
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/10—Compounds containing silicon
    • C10M2201/102—Silicates
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
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    • C10M2203/02—Well-defined aliphatic compounds
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    • C—CHEMISTRY; METALLURGY
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    • 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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Description

BUNDESREPUBLIK DEUTSCHLAND
DEUTSCHES
PATENTAMT
AUSLEGESCHRIFT
Int. CL:
Nummer:
Aktenzeichen:
Anmeldetag:
Auslegetag:
ClOm
Deutsche KI.: 23 c -1/01
1268299
P 12 68 299.4-43
16. August 1962
16. Mai 1968
N-Dialkylaminoalkylalkenylbernsteinsäureesterund N-Polyalkylenaminalkenylbernsteinsäureimide sind als Reinigungsmittel für Schmieröle bekannt. Weiter sind auch Bisphenole als Schmierölzusätze bekannt.
Diese Einzelkomponenten haben jedoch den Nachteil, daß sie bei hohen Temperaturen, wie diese z. B. in Verbrennungskraftmaschinen auftreten, zur Niederschlagsbildung neigen.
Gegenstand der Erfindung ist nun ein Schmieröl, bestehend aus einem mineralischen oder synthetischen öl und einer Kombination von zwei als Schmierölzusätze bekannten Einzelkomponenten sowie gegebenenfalls weiteren üblichen Zusätzen, welches dadurch gekennzeichnet ist, daß es ein Alkyl- bzw. Alkylenbernsteinsäureamid der allgemeinen Formel
R-CH Cs
N —[<R,)X —NH],-.
CH,
Il ο
L-(R1^-N
Schmieröl
Anmelder:
»Shell« Research Limited, London
Vertreter:
Dr. E. Jung, Patentanwalt,
8000 München 23, Siegesstr. 26
Als Erfinder benannt:
George Nacson,
Queen's Park, Chester (Großbritannien);
Gedeminas Joseph Reinis, Edwardsville, JlI.;
Bobby Malone, East Alton, JIl. (V. St. A.)
Beanspruchte Priorität:
Großbritannien vom 18. August 1961 (29 984),
vom 2. Juli 1962
V. St. v. Amerika vom 19. April 1962 (188902)
worin R ein Polyalkyl- oder Polyalkylenrest mit 20 bis 500 Kohlenstoffatomen, Ri eine CHo-Gruppe, .γ und ζ 1 bis 3, y0 bis 6 und R2 ein Wasserstoffatom oder einen Q 5-AlkyIrest bedeuten oder die beiden Reste R2 einen heterocyclischen Ring der Struktur
CH-R
— N
CH,
bilden, in dem R die obige Bedeutung hat, und ein Bisphenol der allgemeinen Formel
0H
worin R1 einen Ci m-Alkylrest, m 1 bis 4 und X eine CHi-Gruppe oder Schwefel bedeutet, enthält.
Vorzugsweise ist R ein Polymeres eines Alkens mit 2 bis 8, insbesondere mit 2 bis 5 Kohlenstoffatomen, in welchem das Polymere ein Molgewicht von 300 bis 5000, insbesondere 800 bis 1500, hat.
Die Zahl der Kohlenstoffatome in dem Rest R beträgt vorzugsweise 30 bis 200. Beispiele solcher Polymere sind: Polyäthylen, Polypropylen, PoIybutylen, Polyisobutylen, Äthylen-Propylen-Mischpolymerisat, Äthylen - Isobutylen - Mischpolymerisat
sowie Äthylen-a-Methylstyrol-Mischpolymerisat.
Vorzugsweise haben jc und ζ den Wert 1.
Wenn y 0 ist, so ist Ri vorzugsweise ein Äthylen-, Propylen- oder Butylenrest, und die R2 sind vorzugsweise Methyl-, Äthyl-, Propyl- oder Butylreste. Es wird besonders bevorzugt, daß Ri 2 oder 3 Kohlenstoffatome und jedes R2 1 Kohlenstoffatom enthält. Wenn y den Wert 1 oder einen höheren Wert hat, ist diese Zahl vorzugsweise 1 bis 6 und besonders zweckmäßig 3. In diesem Fall ist Ri vorzugsweise ein Äthylenrest, und die R» sind vorzugsweise Wasserstoffatome (Monobernsteinsäureimid), oder sie bilden einen heterocyclischen Ring, wie oben
M» 549/379
3 4
beschrieben (Dibernsteinsäureimid). Gemische aus phenyl) - methan, Bis - (2,6 - tert.butyl - 4 - hydroxy-
zwei oder mehr Zusatzstoffen, z. B. von Mono- und phenyl) - methan, Bis-(3,5-ditert.octyl-4-hydroxy-
Diimiden, können mit Vorteil angewandt werden. phenyl) - methan, Bis - (3 - tert.butyl - 5 - tert.octyl-
Das Succinimid wird nach bekannten Verfahren 4-hydroxyphenyl)-methan und besonders Bis-(3,5-dihergestellt. 5 tert.butyl-4-hydroxyphenyl)-methan.
Zwecks Bildung von Dibernsteinsäureimiden sollen Die Bisphenole werden nach bekannten Verfahren
die R.2-Reste dieser Amine Wasserstoff bedeuten. hergestellt.
Beispiele solcher Amine sind: «,^-primäre Poly- Weiter können übliche Schmierölzusätze dem
amine, wie Äthylendiamin, Diäthylentriamin, Tri- erfindungsgemäßen Schmieröl beigemischt werden, äthylentetramin,Propylendiamin,Butylendiamin,Tri- io z.B. Alkyl-, Cycloalkyl-, Alkaryl-, Aralkyl- und
methyltrimethylendiamin, Tetramethylendiamin, Di- Arylphosphite, -phosphate, -phosphonate und deren
aminopenten, Pentamethylendiamin, Diaminohexan, Thioderivate, wie Ca ls-Alkylphosphite, z. B. Di-
Hexamethylendiamin, Heptamethylendiamin, Di- und Tributyl-, -octyl-, -Iauryl-, -stearyl-, -cyclohexyl-,
aminooctan, Decamethylendiamin sowie die höheren -benzyl-, -kresyl-, -phenylphosphite oder -phosphate Homologen bis zu 18 Kohlenstoffatomen. 15 sowie deren Thioderivate; PoSrrTerpenreaktionspro-
Bei der Herstellung von Monobernsteinsäure- dukte; Organophosphate, wie Dibutylmethanphos-
imiden, -amiden und -salzen können die gleichen phonat, Dibutyltrichlormethanphosphonat, Dibutyl-
Amine angewandt werden, oder es können substitu- monochlormethanphosphonat und Dibutylchlorben-
ierte Amine verwendet werden, wie N-Methyl- zolphosphonat. Die Ester von Säuren des fünfwertigen
äthylendiamin, N - Äthyläthylendiamin, N - Propyl- 20 Phosphors, wie Diphenyl-, Dikresyl-, Triphenyl-,
äthylendiamin, N-2-Hydroxypropyläthylendiamin, Trikresyl-, Trilauryl- und Tristearylphosphat, P2S5-
Penta-(l-methylpropylen)-heptamin, Di-(I-methyl- Terpenreaktionsprodukte und deren Mischungen,
butylen) - triamin, Pentaamylenhexamin, Tri- Diese Zusätze werden jeweils in einer Menge von
(1,2,2-trimethyläthylen)-tetramin, Di-(I-methyl- 0,1 bis 10, vorzugsweise 0,25 bis 5 Gewichtsprozent
amylen)-hexamin, Di-(l,3-dimethylpropylen)-pent- 25 zugesetzt.
amin, Penta-(l,5-dimethylamylen)-hexamin, Di- Dem erfindungsgemäßen Schmieröl können auch
(1-methyl-4-äthylbutylen)-triamin, Penta-(l,2-di- noch weitere Zusatzstoffe zugegeben werden; z.B.
methyl -1 - isopropyläthylen) - hexamin und Tetra- Mittel gegen das Fressen, schaumhindernde Mittel,
octylenpentamin. z. B. Siliconpolymere; Verbesserungsmittel für den
Die Amine werden nach bekannten Verfahren 30 Viskositätsindex, z. B. polymere Acrylsäureester;
hergestellt. Hochdruckzusatzstoffe, ζ. B. Dibenzyldisulfid; Rost-
Die Bisphenole können ein bis acht Alkylgruppen Verhinderer, z. B. das Kondensationsprodukt aus
enthalten. Vorzugsweise haben sie aber zwei bis Maleinsäureanhydrid und langkettigen Olefinen;
sechs Alkylgruppen. Bisphenole mit vier Alkyl- Verbesserungsmittel für die öligkeit, z. B. säure-
gruppen werden besonders bevorzugt. Jede dieser 35 freier Talg; sowie oberflächenaktive Mittel, z. B.
Alkylgruppen kann 1 bis 10 Kohlenstoffatome, vor- peroxydierte aromatische Extrakte, zugsweise 2 bis 6 Kohlenstoffatome und besonders
zweckmäßig 4 Kohlenstoffatome, enthalten. Außer- Herstellung von Dibernsteinsäureimiden dem können die in irgendeinem bestimmten Bisphenol enthaltenen Alkylgruppen gleich oder ver- 40 Beisniel 1 schieden sein und können primäre, sekundäre oder
tertiäre Alkylgruppen sein. Bisphenole, die min- Polyisobutylen mit einem Molgewicht von 1185
destens eine tertiäre Alkylgruppe enthalten, werden und einer Bromzahl von 21 wurde auf 100 C erhitzt
besonders bevorzugt. und eine äquivalente Menge Maleinsäureanhydrid
Beispiele solcher Bisphenole sind: Bis-(3-äthyl- 45 langsam im Verlauf von etwa 30 Minuten zugegeben.
4-hydroxyphenyl)-disulfid, Bis-(3-methyl-4-propyl- Die Reaktionsmischung wurde auf 199 bis 204 C
5-hydroxyphenyl)-disulfid, Bis-(2-isopropyl-3-butyl- erhitzt und 16 Stunden auf dieser Temperatur
5-hydroxyphenyl)-selenid, 2,2'-Diäthyl-3-tert.butyl- gehalten. Beim Abkühlen wurde Mono-(polyiso-
4:4'-dihydroxydiphenyIseIenid, Bis-l,2-(2:6-ditert.- butylen)-bernsteinsäureanhydrid durch Auflösen in
butyl-4-hydroxyphenyl)-thiaäthan, Bis-l,2-(2:5-di- 50 1,51 leichtem Erdöl (Siedebereich 60 bis 80 C) und
isopropyl-3-hydroxyphenyD-thiaäthan, Bis-(3:5-di- Abtrennen des Produktes durch Filtrieren gewonnen,
tert.butyl-4-hydroxyphenyl)-sulfid, 2,4-Diisobutyl- Etwa 2 Mol dieses Produktes wurden mit 1 Mol
3-hydroxybenzyl-21,41-dipropyl-31 -hydroxybenzyl- Tetraäthylenpentamin vermischt und zu einer Lösung
sulfid. Bis-1,2-(3-octyl-5-tert.butyl-4-hydroxy- in leichtem Erdöl zugegeben. Das Leichtöl wurde
phenyl)-äthan, Bis-l,l-(2,6-diisopropyl-4-hydroxy- 55 abdestilliert und durch 1 1 Toluol ersetzt, das eben-
phenyl)-äthan, l,2-Bis-(2,4-ditert.pentyl-3-hydroxy- falls abdestilliert wurde, um das Wasser azeotrop
phenyl)-propan, Bis-2,2-(4,5-ditert.butyl-2-hydroxy- zu entfernen. Der Rückstand wurde auf 199 bis
phenyl) - propan, Bis - (2 - tert.butyl - 2 - isopentyl- 204 C erhitzt und 3 Stunden auf dieser Temperatur
4-hydroxyphenyl)-amin, Bis-(3,5-dibutyl-4-hydroxy- gehalten. Das isolierte Produkt. Tetraäthylenpent-
phenyl)-äther, Bis-(2,6-dipropyl-4-hydroxyphesiyl)- 60 amindiimid der Mono-(polyisobutylen)-bernstein-
äther, Bis-(2,5-dipentyl-4-hydroxyphenyl)-sulfid. säure, war in öl löslich und zeigte vorzügliche
Bis - (2,5 - dihexyl - 3 - hydroxyphenyl) - sulfid. Bis- Reinigungsungseigenschaften. (2 - methyl - 5 - tert.butyl - 4 - hydroxyphenyl) - sulfid.
Bis-(2-methyl-5-tert.butyl-6-hydroxyphenyl)-sulfid Beispiel 2 und besonders Bis-(3-tert.butyl-5-methyl-2-hydroxy- 65
phenyl)-sulfid. Beispiele von Bisphenolen mit einer Etwa 0,45 Mol Tetraäthylenpentamin und 1 Mol
Methylenbrücke sind :Bis-(2,3-ditert.butyl-4-hydroxy- des im wesentlichen unter den im Beispiel 1 be-
phenyl)-methan, Bis - (2,5-ditertbutyl-4-hydroxy- schriebenen Bedingungen hergestellten Mono-(poly-
butenyl)-bernsteinsäureanhydrids wurden unter Rühren in einer Stickstoffatmosphäre bei 52 C vermischt. Die Temperatur wurde im Verlauf einer Stunde auf 177 C erhöht, worauf der absolute Druck während 30 Minuten auf etwa 200 Torr herabgesetzt wurde, um das Wasser zu entfernen. Darauf ließ man das Reaktionsgemisch bei dem genannten verringerten Druck auf Zimmertemperatur abkühlen.
Beispiel 3
Etwa 1 Mol Mono-(polybutenyl)-bernsteinsäureanhydrid aus Beispiel 2 wurde unter den Reaktionsbedingungen gemäß Beispiel 2 mit etwa 0,5 Mol Triäthylentetramin umgesetzt und ein Endprodukt, wie es oben identifiziert ist, erhalten, das öllöslich war und vorzügliche Reinigungseigenschaften aufwies.
Beispiel
Olefin zu Bernsteinsäureanhydrid
Polyisobutylen (Molgewicht 850) zu Bernsteinsäureanhydrid
Polyisobutylen (Molgewicht 850) zu Bernsteinsäureanhydrid
Polyäthylen-Isobutylen (Molgewicht 1000) zu Bernsteinsäureanhydrid
Polyäthylen-u-Methylstyrol (Molgewicht 800) zu Bernsteinsäureanhydrid
Polyisobutylen (Molgewicht 1000) zu Bernsteinsäureanhydrid
Polyisobutylen (Molgewicht 1500) zu Bernsteinsäureanhydrid
Polypropylen-Polyisobutylen (Molgewicht 3000) zu Bernsteinsäureanhydrid
Diäthylentriamin
M,f>j-Pentamethylendiamin
Tetraäthylenpentamin
Tetraäthylenpen tamin
methylendiamin
f/,f)-Butylendiamin
Tetraäthylenpentamin
Herstellung von Monobernsteinsäureimiden Beispiel 11
Etwa 0,5 Mol Mono-(polyisobutylen)-bernsteinsäureanhydrid. dessen Polyisobutylenrest ein Molgewicht 615 und eine Bromzahl 21 aufwies, wurde mit 1,0 Mol Tetraäthylenpentamin in Leichtbenzinlösung bei 177 bis 216 C während etwa 20 Stunden umgesetzt. Das leichte Erdöl wurde abdestilliert und durch 1 1 Toluol ersetzt, das dann ebenfalls zwecks azeotroper Abtrennung des Wassers abdestilliert wurde. Der Rückstand wurde auf 199 bis 204 C erhitzt und 3 Stunden auf dieser Temperatur gehalten. Das Endprodukt war ein öllösliches Tetraäthylenpentaminmonoimid von Mono-(polyisobutylen ^bernsteinsäure.
Beispiel 12
84 g (0,45 Mol) N-Dipropyltetraäthylenpentamin und 702 g (0,45 Mol) des oben beschriebenen Mono-(polybutylen)-bernsteinsäureanhydrids nach Beispiel 2 wurde unter Rühren bei 52 C in einer Stickstoffatmosphäre vermischt. Die Temperatur wurde im Verlauf einer Stunde auf 204 C erhöht, worauf der absolute Druck während 30 Minuten auf etwa 200 Torr verringert wurde, um die Entfernung des Wassers zu erleichtern. Dann ließ man das Reak-2 : 1
2 : 1
2 : 1
2 : 1
2 : 1
3 : 1
3 : 1
Temperatur
C
204
177
191
177
177
204
204
Endprodukt
Diäthylentriamindiimid von Mono-(polyisobutylen)-bernsteinsäure
Pentamethylendiamin-bis-(polyisobutylenbernsteinsäureimid)
Tetraäthylenpentamindiimid von Mono-(polyäthylen-Isobutylen)-bernsteinsäure
Tetraäthylenpentamindiimid von Mono-(polyäthylena-Methylstyrol)-bernsteinsäure
Hexamethylendiamin-bis-(polyisobutylenbernsteinsäureimid)
Butylendiamin-bis-(polyisobutylenbernsteinsäureimid)
Tetraäthylenpentamindiimid von Mono-(polypropylenpolyisobutylen )-bernsteinsäure
tionsgemisch bei diesem verringerten Druck auf Zimmertemperatur abkühlen.
Beispiel 13
Es wurde nach Beispiel 12 gearbeitet mit der Ausnahme, daß Dimethylaminopropylamin im Reaktionsgemisch verwendet wurde und das Molverhältnis des Polyamine zu dem Anhydrid etwa 1:1 betrug. Das Endprodukt ist ein N-Dimethylpropylalkenylbernsteinsäureimid.
Herstellung von Halbamiden Beispiel 14
Durch Umsetzen eines Polyisobutylene (Molgewicht 850) mit Bernsteinsäureanhydrid bei etwa 204 C, wie im Beispiel 1, wurde Polyisobutylenbernsteinsäureanhydrid hergestellt. Etwa 500 g des so erhaltenen Polyisobutylenbernsteinsäureanhydrids wurden mit 50 g Diäthylentriamin in Toluol bei Zimmertemperatur vermischt. Das Amin wurde in Portionen zugegeben, und die Temperatur wurde so geregelt, daß sie nicht über etwa 49* C anstieg. Die Reaktion verlief in 15 bis 30 Minuten, worauf das Lösungsmittel entfernt und das Endprodukt isoliert wurde.
Weitere Beispiele von Monobernsteinsäureimiden:
Beispiel Olefin zu Bernsteinsäureanhydrid Amin Mol
verhältnis 		Temperatur
C 		Art des Endprodukts
15 Polyisobutylen (Molgewicht 850) N-Diäthylaminpropyl- 1 : 1 216 Imid
zu Bernsteinsäureanhydrid amin
16 Polyisobutylen (Molgewicht 850) N-Methyltetraäthylen- 1,5: 1 49 Halbamid
zu Bernsteinsäureanhydrid pentamin
17 Polyäthylen-Isobutylen (Mol N-Dimethylamin- 1 : 1 232 Imid
gewicht 1000) zu Bernstein propylamin
säureanhydrid
18 Polyäthylen-a-Methylstyrol (Mol N-Diäthylmethyl- 1 : 1 232 Imid
gewicht 800) zu Bernsteinsäure-
anfivdrid 		aminoheptylamin
19 Polyisobutylen (Molgewicht 1000) N-Dimethyläthylen- 1 : 1 49 Amid-Aminsalz
zu Bernsteinsäureanhydrid diamin
20 Polyäthylen-Propylen zu Bern N-Dimethyldiäthylen- 1 : 1 221 Imid
steinsäureanhydrid triamin
40
45
Gemische von Imiden und von einem oder'mehreren Imiden und deren Salzen werden mit Vorteil verwendet. Die Mengenverhältnisse zwischen den Komponenten können innerhalb weiter Grenzen verändert werden, z. B. von 10 : 90 bis 90 : 10. Als Beispiele für solche Gemische können angeführt werden: (1) 80% Beispiel 1 und 20% Beispiel 11; (2) 80% Beispiel 11 und 20% Beispiel 2; (3) 90% Beispiel 12 und 10% Beispiel 2; (4) 80% Beispiel 1 und 20% Beispiel 13; (5) 70% Beispiel 7 und 30% Beispiel 16; (6) 50% Beispiel 1 und 50% Beispiel 19.
Zur weiteren Erläuterung der Erfindung wurden die nächstehend angegebenen Schmierölmischungen hergestellt und geprüft. Die Prozentsätze beziehen sich auf Gewicht.
Gemisch A
Zusatz nach Beispiel 1 2%
Bis-(3,5-ditert.butyl-4-hydroxyphenyl)-
methan 0,5%
Mineralisches Schmieröl (SAE 20) .. 97,5%
Gemisch B
Zusatz nach Beispiel 2 2%
Bis-(3,5-ditert.butyl-4-hydroxyphenyl)-
methan 0,75%
Mineralisches Schmieröl (SAE 20) .. 97,25%
Gemisch C
Zusatz nach Beispiel 2 2%
Zusatz nach Beispiel 12 0,50O
Bis-(3,5-ditert.butyl-4-hydroxyphenyl)-
sulfid 0,75"/,,
Mineralisches Schmieröl (SAE 20) .. 96,75%
Gemisch D
Zusatz nach Beispiel 4 2%
Zusatz nach Beispiel 14 0,5%
Bis-(3,5-ditert.butyl-4-hydroxyphenyl)-
methan 0,75"/,,
Mineralisches Schmieröl
(SAE 20 W-30) 96,75%
55
60 Gemisch E
Zusatz nach Beispiel 1 2%
Zusatz nach Beispiel 12 0,5%
Bis-(3,5-ditert.butyl-4-hydroxyphenyl)-
methan 0,75°/»
Trikresylphosphat 0,5%
Mineralisches Schmieröl (SAE 20) .. 96,25%
Gemisch F
Zusatz nach Beispiel 1 2%
Zusatz nach Beispiel 11 0,5 %
Bis-(3,5-ditert.butyl-4-hydroxyphenyl)-
methan 0,75%
Trikresylphosphat 0,5%
Mineralisches Schmieröl (SAE 20) .. 96,25%
Gemisch G
Zusatz nach Beispiel 4 0,2"'o
Zusatz nach Beispiel 11 1 "'0
Bis-(3,5-ditert.butyl-4-hydroxyphenyl)-
methan 0.75%
Trikresylphosphat 0,5%
Mineralisches Schmieröl (SAE 20) .. 96,25%
Gemisch H
Zusatz nach Beispiel 1 0,3 %
Zusatz nach Beispiel 12 2,5'Vo
Bis-(3,5-ditert.butyI-4-hydroxyphenyl)-
methan 0,75%
Trikresylphosphat 0,80%
Dikresylphosphat 0,04%
Mineralisches Schmieröl
(SAE 10 W-30) 95,650A,
Gemisch .1
Zusatz nach Beispiel 11 2"/«
Bis-(3,5-ditert.butyl-4-hydroxyphenyl)-
methan 0,75%
Trikresylphosphat 0,5%
Mineralisches Schmieröl (SAE 20) .. 96.75%
Diese Gemische wurden unter verschiedenen laboratoriumsmäßigen und praktischen Motorbedingungen geprüft.
Heißplattentest
Eine Platte von 30,48 cm Länge und 6,35 cm Breite ist längs der Schmalseite am oberen und unteren Ende mit Rinnen für die Verteilung und für das Auffangen von öl versehen. Die Platte wird auf 270 C erhitzt und auf dieser Temperatur gehalten, Man läßt 500 g Schmieröl 6 Stunden lang über die Platte zirkulieren, wobei eine Fließgeschwindigkeit von etwa 6,5 ecm pro Minute aufrechterhalten wird. Nach Beendigung der Prüfung werden die Niederschläge von der Platte abgekratzt und mit Petroläther (Siedepunkt 60 bis 80 C) in einen gesinterten Glasfiltertiegel gespült. Nach gründlichem Waschen mit Petroläther wird der Niederschlag bei 100 C getrocknet und nach dem Kühlen gewogen.
Die Prüfung wurde unter Verwendung von Gemisch J und einer Vielzahl von Schmierölgemischen zu Vergleichszwecken durchgeführt. Die Ergebnisse sind in der folgenden Tabelle zusammengefaßt.
Heißplattentest Niederschlags
Basisöl Zusatz menge in g
198.4
SAE 20 21Vo nach Beispiel 11 182,0
SAE 20 0,75% AN 2* 125
SAE 20 0,75% AN 2*
+ 0,75% TTP** 31,4
SAE 20 2"/ο nach Beispiel 11
+ 0,75% AN 2* 3,8
SAE 20 Gemisch J 14,4
SAE 20 10Ai nach Beispiel 11
+ 0,75% AN 2*
+ 0,5% TTP** 98,0
SAE 20 4,5% im Handel erhältliches
Mischpolymerisat aus
Laurylmethacrylat und
N-Vinylpyrrolidon 77,2
SAE 20 4,5% im Handel erhältliches
Mischpolymerisat aus
Laurylmethacrylat und
N-Vinylpyrrolidon
+ 0,75% AN 2*
35
40
45
1 Bis-(3,5-ditert.butyl-4-hydroxyphenyl)- methan.
' Tritolyl- oder Trikresylphosphat.
10

Claims (1)

  1. Patentanspruch:
    Schmieröl, bestehend aus einem mineralischen oder synthetischen öl und einer Kombination von zwei als Schmierölzusätze bekannten Einzelkomponenten sowie gegebenenfalls weiteren üblichen Zusätzen,dadurch gekennzeichnet, daß es ein Alkyl- bzw. Alkylenbernsteinsäureimid der allgemeinen Formel
    R-CH
    worin R ein Polyalkyl- oder Polyalkylenrest mit 20 bis 500 Kohlenstoffatomen, Ri eine CH2-Gruppe, χ und ζ 1 bis 3, y 0 bis 6 und Rg ein Wasserstoffatom oder einen Ci 5-Alkylrest bedeuten oder die beiden Reste R2 einen heterocyclischen Ring der Struktur
    — N
    CH-R
    CH2
    Il
    bilden, in dem R die obige Bedeutung hat, und ein Bisphenol der allgemeinen Formel
    HO
    OH
    worin R1 einen Ci -10-Alkylrest, m 1 bis 4 und X eine CH2-Gruppe oder Schwefel bedeutet, enthält.
    In Betracht gezogene Druckschriften:
    Britische Patentschrift Nr. 884 164.
    809 549/379 5.6» Q Bundeadruckerei Berlin
DEP1268299A 1961-08-18 1962-08-16 Schmieroel Pending DE1268299B (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB29984/61A GB946032A (en) 1961-08-18 1961-08-18 Improved lubricating oil compositions
US18890262A 1962-04-19 1962-04-19

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DE1268299B true DE1268299B (de) 1968-05-16

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GB1102032A (en) * 1965-04-27 1968-02-07 Monsanto Chemicals Antioxidant compositions
US3454496A (en) * 1967-01-17 1969-07-08 Shell Oil Co Lubricant compositions
DE1794133B2 (de) * 1968-09-13 1975-09-25 The Lubrizol Corp., Cleveland, Ohio (V.St.A.). Schmierole
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US4755311A (en) * 1986-08-14 1988-07-05 The Lubrizol Corporation Phosphorus-, sulfur- and boron-containing compositions, and lubricant and functional fluid compositions containing same
US5391307A (en) * 1989-07-07 1995-02-21 Tonen Corp. Lubricating oil composition
CA2030096A1 (en) * 1989-11-27 1991-05-28 Stephen Norman Gear oils and additives therefor
US5328620A (en) * 1992-12-21 1994-07-12 The Lubrizol Corporation Oil additive package useful in diesel engine and transmission lubricants
US6107409A (en) * 1998-05-06 2000-08-22 Bridgestone Corporation Gels derived from extending grafted comb polymers and polypropylene via a solution synthesis
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US3357920A (en) 1967-12-12

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