DE1276276B - Esterschmieroel - Google Patents

Esterschmieroel

Info

Publication number
DE1276276B
DE1276276B DES98907A DES0098907A DE1276276B DE 1276276 B DE1276276 B DE 1276276B DE S98907 A DES98907 A DE S98907A DE S0098907 A DES0098907 A DE S0098907A DE 1276276 B DE1276276 B DE 1276276B
Authority
DE
Germany
Prior art keywords
imidazoline
thiono
bis
methyl
esters
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
DES98907A
Other languages
English (en)
Inventor
William Alexander Munday
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 Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
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 Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Publication of DE1276276B publication Critical patent/DE1276276B/de
Pending legal-status Critical Current

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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D233/30—Oxygen or sulfur atoms
    • C07D233/42—Sulfur atoms
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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
    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl 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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    • C10M2207/121—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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Description

BUNDESREPUBLIK DEUTSCHLAND
DEUTSCHES
PATENTAMT
AUSLEGESCHRIFT
Int. Cl.:
Nummer:
Aktenzeichen:
Anmeldetag:
Auslegetag:
ClOm
Deutsche Kl.: 23 c -1/01
P 12 76 276.4-43 (S 98907)
18. August 1965
29. August 1968
Die bekannten Antioxydationsmittel für Esterschmieröle, wie Phenothiazin, reichen unter scharfen Betriebsbedingungen oft nicht aus, und sie weisen außerdem den Nachteil einer Neigung zur Schlammbildung auf.
Es wurde nun gefunden, daß dieser Nachteil beseitigt wird, wenn man Esterölen ein Imidazolin der allgemeinen Formel
R-C C
f.
NH
in welcher R ein heterocyclischer Ring oder ein substituierter Arylrest und R' ein Ci -4-Alkylrest ist, zusetzt.
Zur Klarstellung wird darauf hingewiesen, daß der Imidazolinring im Rahmen der Erfindung wie folgt numeriert wird:
Esterschmieröl
Anmelder:
Shell Internationale Research Maatschappij N. V., Den Haag
Vertreter:
Dr. E. Jung und Dr. V. Vossius, Patentanwälte,
8000 München 23, Siegesstr. 26
Als Erfinder benannt:
William Alexander Munday,
Chester, Cheshire (Großbritannien)
Beanspruchte Priorität:
Großbritannien vom 20. August 1964 (34089),
vom 23.JuIi 1965 v
Die substituierten Imidazoline können nach irgendeinem bekannten und geeigneten Verfahren hergestellt werden, Im Rahmen der Erfindung können beispielsweise die nachstehenden substituierten Imidazoline eingesetzt werden: 2,5-Bis-(4'-pyridyl)-2-methyl-4-thiono-imidazolin; 2,5-Bis-(2'-furyl)-2-methyl-4 - thiono - imidazolin; 2,5 - Bis - (p - tolyl) - 2 - methyl-4-thiono-imidazolin; 2,5-Bis-(p-isopropylphenyl)-2 - methyl - 4 - thiono - imidazolin; 2,5 - Bis - (p - chlorphenyl)-2-methyl-4-thiono-imidazolin und 2,5-Bis-(p-methoxyphenyl)-2-methyl-4-thiono-imidazolin.
Diese substituierten Imidazoline liegen in den Schmierölen in Konzentrationen von 0,1 bis 5,0 Gewichtsprozent und vorzugsweise von 0,5 bis 2 Gewichtsprozent, bezogen auf das fertige Schmiermittel, vor.
Vorzugsweise werden im Rahmen der Erfindung als Basisschmiermittel einfache Ester angewendet. Unter einem einfachen Ester wird ein aus einer aliphatischen Dicarbonsäure und einem aliphatischen einwertigen Alkohol gebildeter Ester verstanden, wobei einfache Ester aus einer aliphatischen Dicarbonsäure mit 6 bis 10 Kohlenstoffatomen im Molekül und einem verzweigtkettigen einwertigen Alkohol mit 6 bis 12 Kohlenstoffatomen im Molekül bevorzugt werden, insbesondere solche Ester, die sich von Alkoholen ohne Wasserstoffatom am ^-Kohlenstoffatom ableiten. Für die Zwecke der vorstehenden Erfindung eignen sich beispielsweise die nachstehenden einfachen Ester: Dinonylsebacat, Di - (2 - äthylhexyl) - sebacat, Diisooctylazelat, Di-(3,5,5-trimethylhexyl)-adipat und 2,2,4-TrimethyJ-pentylazelat.
Es können aber auch komplexe Ester und Polyester oder Gemische daraus als Schmiermittelbasis verwendet werden.
Unter einem komplexen Ester wird eine Verbindung verstanden, welche sich in den unterschiedlichsten Kombinationen von einer aliphatischen Dicarbonsäure, einem Glykol oder Polyglykol und einem aliphatischen einwertigen Alkohol und/oder einer aliphatischen Monocarbonsäure ableitet. Einige typische solcher komplexen Ester können schematisch durch die Kombination AD(GD)nA, A(DG)11M und MG(DG)nM dargestellt werden, wobei A, D, G und M jeweils die bei der Veresterung in das Molekül eintretenden Reste eines aliphatischen einwertigen Alkohols, einer aliphatischen Dicarbonsäure, eines Glykole oder Polyglykols bzw. einer aliphatischen Monocarbonsäure bedeuten und η ein«! ganze Zahl von 1 bis 6 ist. Beispiele für typische AUSgangS-
materialien zur Herstellung solcher Ester sind 2-ÄthylbutylalkohoI, 2-Äthylhexylalkohol, Capronsäuren, Pelargonsäure, Caprinsäure, NeopentylglykoL, Äthylenglykol, Propylenglykol, Polyglykole, wie Polyäthylenglykole, Sebacinsäure, Adipinsäure, Azelainsäure und Pimelinsäure.
Unter Polyestern werden Verbindungen verstanden, die sich von aliphatischen Alkoholen mit wenigstens drei Hydroxylgruppen ableiten, beispielsweise Ester des Trimethylolpropans, ferner Tetraester, wie Pentaerythritoltetraester oder das Dimere oder Trimere eines solchen Esters, sowie Dipentaerythritolester. Solche Ester leiten sich vorzugsweise von Fettsäuren ab, welche im Säurerest 4 bis 18 und insbesondere 6 bis 14 Kohlenstoffatome enthalten.
Die Schmiermittel gemäß der Erfindung können auch zusätzlich andere bekannte Verdickungsmittel, Hochdruckmittel, Antioxydationsmittel, Metalldesaküvatoren, Antikorrosionsmittel, Antischaummittel und Farbstoffe enthalten. Als Verdickungsmittel eignen sich z. B. Polyalkylenglykole und deren Mono- und Diäther sowie Ester und die Polymerisate von Estern der Acrylsäure sowie von 1-Alkylacrylsäure, aber auch alle anderen üblichen Verdickungsmittel.
Beispiel I
Di-(2-äthylhexyl)-sebacat mit einer Anfangsviskosität bei 98,9°C von 3,4 cSt wurde als Basisschmiermittel verwendet und enthielt einen Zusatz von 0,5 Gewichtsprozent an 2,5-Bis-(4'-pyridyl)-2-methyl-4-thiono-imidazolin.
25 Shaken Circulatory Oxidation Test (SCOT)
Bei diesem Test, der in allen Einzelheiten in »Journal Inst. Petroleum«, Vol. 48, Nr. 457, Januar 1962, beschrieben ist, werden kleine Mengen des zu prüfenden Öles bei einer Temperatur von 16O0C in Gegenwart eines Katalysators in einem Reaktionsgefäß kräftig mit Sauerstoff geschüttelt, um das öl mit dem Sauerstoff in innige Berührung zu bringen, wobei man den Sauerstoff durch das Reaktionsgefäß hindurchleitet. Der in einer bestimmten Zeiteinheit absorbierte Sauerstoff wird bestimmt und als Induktionsperiode angegeben.
Die ölmischungen gemäß den Beispielen wurden bei diesem Oxydationsversuch auch hinsichtlich des Gehaltes (Gewichtsprozent) an Unlöslichem geprüft.
Aus der nachstehenden Tabelle ist ersichtlich, daß die erfindungsgemäßen Gemische der Beispiele I bis VI größere Induktionsperioden aufweisen, d. h. eine größere Oxydationsbeständigkeit zeigen, als das Vergieichsgemisch des Beispieles VII.
Weiterhin ergibt sich aus dieser Tabelle, daß das Schmiermittelgemisch von Beispiel VII, welches ein bekanntes Antioxydationsmittel enthält, nach der Oxydationsprüfung unter SCOT-Bedingungen einen bestimmten Anteil an unlöslichen Stoffen aufweist, die im allgemeinen als Schlamm bezeichnet werden, während die erfindungsgemäßen Schmiermittel unter den gleichen Bedingungen völlig schlammfrei sind.
30
Boispiel II
Das Basisöl von Beispiel I mit einem Gehalt von 0,5 Gewichtsprozent an 2,5-Bis-(2'-furyl)-2-methyl-4-thiono-imidazoIin.
Beispiel III
Das Basisöl von Beispiel I mit einem Gehalt von 0,5 Gewichtsprozent an 2,5-Bis-(p-tolyl)-2-methyl-4-thiono-imidazolin.
Beispiel IV
Das Basisöl von Beispiel I mit einem Gehalt von 0,5 Gewichtsprozent an 2,5-Bis-(p-isopropylphenyl)-2-methyl-4-thiono-imidazolin.
Bei spiel V
Das Basisöl von Beispiel Ϊ mit einem Gehalt von 0,5 Gewichtsprozent an 2,5-Bis-(p-chlorphenyl)-2-methyl-4-thiono-imidazoIin.
Beispiel VI
Das Basisöl von Beispiel I mit einem Gehalt von 0,5 Gewichtsprozent an 2,5-Bis-(p-methoxyphenyl)-2-methyl-^thiono-imidazolin.
Beispiel VII
Das Basisöl von Beispiel I mit einem Gehalt von 0,5 Gewichtsprozent an Phenothiazin.
Induktionsperiode Oxydiertes öl
Beispiel (Minuten) unlösliches
in Gewichtsprozent
I 550 0 '
II 555 0
III 500 0
IV 650 0
V 585 0
VI 525 0
VII 408 0,13

Claims (1)

  1. Patentanspruch:
    Esterschmieröl, dadurch gekennzeichnet, daß es ein Imidazolin der allgemeinen Formel
    R-C
    S = C-
    NH
    in welcher R ein heterocyclische/ Ring oder ein substitutierter Arylrest und R' ein Ci^i-Alkyliest ist, enthält.
    In Betracht gezogene Druckschriften:
    USA.-Patentschriften Nr. 2 599 384, 2 968 625.
    809 598/524 8.68 0 Bundesdruckerei Berlin
DES98907A 1964-08-20 1965-08-18 Esterschmieroel Pending DE1276276B (de)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6187722B1 (en) * 1999-07-22 2001-02-13 Uniroyal Chemical Company, Inc. Imidazole thione additives for lubricants
EP1361217B1 (de) * 2001-01-24 2005-03-23 Rohm And Haas Company 4-Thionoimidazolidinderivate als öllösliche Additive für Schmieröle
EP1227144B1 (de) * 2001-01-24 2005-05-25 Crompton Corporation Oel-lösliche Zusammensetzungen für Schmiermittel enthaltend Imidazolidine thione als Zusatz
US6602831B2 (en) 2001-01-24 2003-08-05 Rohm And Haas Company Oil-soluble additives for lubricating oils
US6734149B2 (en) 2001-01-24 2004-05-11 Rohm And Haas Company Combination of additives for lubricating oils
EP1394239A1 (de) * 2002-08-07 2004-03-03 Rohm And Haas Company Cyclische Thioamiden als Zusatz für Schmieröle

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2599384A (en) * 1950-04-08 1952-06-03 Petrolite Corp Solid stick corrosion inhibitors and a process for preventing corrosion of oil and gas well equipment
US2968625A (en) * 1956-07-25 1961-01-17 Standard Oil Co Fluid power transmission

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2599384A (en) * 1950-04-08 1952-06-03 Petrolite Corp Solid stick corrosion inhibitors and a process for preventing corrosion of oil and gas well equipment
US2968625A (en) * 1956-07-25 1961-01-17 Standard Oil Co Fluid power transmission

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GB1053716A (de)
NL6510788A (de) 1966-02-21

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