EP0000514B1 - Phenol-N, N-dioctyl-dithio-carbaminsäureester und damit stabilisierte Schmiermittel - Google Patents

Phenol-N, N-dioctyl-dithio-carbaminsäureester und damit stabilisierte Schmiermittel Download PDF

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Publication number
EP0000514B1
EP0000514B1 EP78100387A EP78100387A EP0000514B1 EP 0000514 B1 EP0000514 B1 EP 0000514B1 EP 78100387 A EP78100387 A EP 78100387A EP 78100387 A EP78100387 A EP 78100387A EP 0000514 B1 EP0000514 B1 EP 0000514B1
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Prior art keywords
alkyl
formula
compound
stabiliser
lubricants
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EP78100387A
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English (en)
French (fr)
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EP0000514A1 (de
Inventor
Siegfried Rosenberger
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Novartis AG
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Ciba Geigy AG
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    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/12—Thio-acids; Thiocyanates; Derivatives thereof
    • C10M135/14—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond
    • C10M135/18—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond thiocarbamic type, e.g. containing the groups
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Definitions

  • the present invention relates to lubricants stabilized with phenol-N, N-dioctyl-dithio-carbamates, or to the use of phenol-N, N-dioctyl-dithiocarbamates for stabilizing lubricants.
  • additives are generally added to mineral and synthetic lubricants to improve their performance properties.
  • additives which are intended to protect the devices to be lubricated from frictional wear.
  • wear inhibitors are required to increase the load-bearing capacity of the lubricant and not to have a corrosive effect on the metal parts to be protected.
  • Alkyl-substituted phenols and dithiocarbams such as the already widely used commercial products 2,6-di-tert-butyl-4-methylphenol or S-benzyl-N, N-diethyldithiocarbamate, are already generally known in the lubricant sector as antioxidants.
  • US Pat. No. 3,412,026 describes a lubricant composition containing a small proportion of a mixture of antimony-N, N-dialkyldithiocarbamate and dialkylhydroxybenzyl-N, N-diphenyl-dithiocarbamate with good stability.
  • GB-A-1 024 651 describes metal salts of carbamides containing 2,6-dialkylphenol which are to be used as antioxidants and antiwear additives in lubricants. However, it was found that the effects of these metal salt additives are impaired by the formation of residues. W.M. Denton, "Screening of Compounds for Anti-Oxidant Activity in Motor Oil," Inst. Of Pet Review, 2/66, 46-54, describes S- (3,5-di-tert-butyl-4-hydroxy- benzyl) -N, N-di-n-butyl-dithiocarbamate as a lubricant additive.
  • the dithiocarbamate group is bonded to the phenol ring in the o- or in particular in the m- or p-, but preferably in the p-position to the hydroxyl group.
  • Lubricants which are a stabilizer are a compound of the formula contain, wherein R and R 1 are C 1 -C 4 alkyl.
  • lubricants that act as a stabilizer, a compound of the formula included, wherein R and R 1 are C 1 -C 4 alkyl.
  • the invention also relates to compounds of the formula wherein RC 1 -C 1Z alkyl, C 5 -C 7 cycloalkyl, C 6 -C 10 aryl optionally substituted by C 1 -C 6 alkyl, C 7 -C 22 aralkyl and R 1 and R 2 each independently represent H or R. .
  • hydroxybenzyl-N, N-dioctyl-dithiocarbamates to be used according to the invention can be obtained by generally known methods, for example by using mono- or di-chloromethylphenols of the formulas with the equivalent amounts of corresponding Na dithiocarbamates of the formula in an inert solvent such as acetonitrile, toluene, ether or chloroform with the elimination of NaCl.
  • an inert solvent such as acetonitrile, toluene, ether or chloroform with the elimination of NaCl.
  • the ortho- and in particular the para-hydroxybenzyl-dithiocarbamates can be obtained analogously in the manner cited above for the meta derivatives, but they are preferably prepared by known methods by reacting molar amounts of a corresponding substituted phenol of the formula. with formaldehyde, carbon disulfide and an amine of the formula
  • the compounds of the formula act as stabilizers against the oxidation and corrosion effects in lubricants.
  • Mineral and synthetic lubricating oils and mixtures thereof which contain 0.001 to 5% by weight, based on the lubricant, and preferably 0.02-3% of a compound of the formula I, have excellent lubricating properties, which are due to greatly reduced wear and tear on the lubricants Friction partners become clear.
  • lubricants in question are familiar to the person skilled in the art and e.g. in the "Lubricant Pocket Book” (Hüthig Verlag, Heidelberg, 1974). Mineral oils are particularly suitable.
  • the lubricating oil formulation can additionally contain other additives that are added to improve certain performance properties, such as antioxidants, metal passivators, rust inhibitors, viscosity index improvers, pour point depressants, dispersants / surfactants and other wear protection additives.
  • additives such as antioxidants, metal passivators, rust inhibitors, viscosity index improvers, pour point depressants, dispersants / surfactants and other wear protection additives.
  • antioxidants are:
  • metal passivators examples are:
  • Polymethacrylates vinyl pyrrolidone methacrylate copolymers, polybutenes, olefin copolymers, styrene / acrylate copolymers.
  • pour point depressants examples are:
  • dispersants / surfactants are polybutenyl succinic acid imides.
  • Compounds containing sulfur and / or phosphorus and / or halogen such as sulfurized vegetable oils, zinc dialkyldithiophosphates, tritolyl phosphate, chlorinated paraffins, alkyl and aryl disulfides.
  • Example 1 S- (3-Hydroxy-4-tert-butyl-2,6-dimethylbenzyl) -N, N-di-n-octyldithiocarbamate.
  • the mixture is then poured into about 1 liter of ice water, the toluene phase is separated off after the addition of a further 100 ml of toluene, shaken out with water, dried over calcium chloride and evaporated in vacuo.
  • the S- (3-hydroxy-4-tert-butyl-2,6-dimethylbenzyl) -N, N-di-n-octyl-dithiocarbamate remains as a brownish viscous oil and is already sufficiently pure and suitable for use as a stabilizer elementary analytical and chromatographic largely uniform.
  • di-n-octyl (Example 2) to be used according to the invention and the di-n-butyl (Example 3) derivatives to be compared are listed in the following table. They are obtained by known methods, preferably by reacting appropriate phenols (column 2 of the table) with formaldehyde, carbon disulfide and the corresponding secondary amine (column 3 of the table) (for example according to US Pat. No. 2,757,174).
  • Example 5 Oil Oxidation Test, Standard Version According to ASTM D 2272 (Rotary Bomb Oxidation Test)
  • the glass vessel is in a stainless steel bomb with a pressure gauge.
  • the bomb rotates axially at 100 rpm. at an angle of 30 ° to the horizontal, in an oil bath at 150 ° C.
  • the oxygen pressure is initially around 6 atm (90 psi) before heating, rises to 150 ° C to just under 14 atm (200 psi) and remains constant until oxidation begins.
  • the test is complete when the pressure drops by 1.7 Atm (25 psi). The time is recorded in minutes.

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

Description

  • Die vorliegende Erfindung betrifft mit Phenol-N,N-dioctyl-dithio-carbamaten stabilisierte Schmiermittel, bzw. die Verwendung von Phenol-N,N-dioctyl-dithiocarbamaten zum Stabilisieren von Schmiermitteln.
  • Mineralischen und synthetischen Schmierstoffen werden im allgemeinen verschiedene Zusatzstoffe zur Verbesserung ihrer Gebrauchseigenschaften beigegeben. Insbesondere besteht ein Bedarf an Additiven, welche die zu schmierenden Vorrichtungen vor Reibungsabnutzung schützen sollen. An solche Verschleissinhibitoren wird die Anforderung gestellt, dass sie das Lasttragevermögen des Schmierstoffes erhöhen und nicht korrodierend auf die zu schützenden Metallteile wirken.
  • Alkylsubstituierte Phenole und Dithiocarbamte, wie beispielsweise die bereits vielseitig verwendeten Handelspordukte 2,6-Di-tert.-butyl-4-methylphenol bzw. S-Benzyl-N,N-diäthyl- dithiocarbamat, sind bereits allgemein auch im Schmiermittelsektor als Antioxydantien bekannt. In der US-A-3,412,026 wird eine Schmiermittelzusammensetzung enthaltend einen kleinen Anteil einer Mischung von Antimon-N,N-dialkyldithiocarbamat und Dialkylhydroxybenzyl-N,N-diphenyl-dithio- carbamat mit guter Stabilität beschrieben. Die GB-A-1 024 651 beschreibt Metallsalze von 2,6-Dialkylphenol enthaltenden Carbamiden, die als Antioxydantien und Antiwear-Additive in Schmiermitteln einzusetzen sind. Es zeigte sich jedoch, dass diese Metallsalz-Zusätze durch Bildung von Rückständen in ihrer Wirkung beeinträchtigt werden. W.M. Denton, "Screening of compounds for Anti-Oxidant Activity in Motor Oil", Inst. of Pet.Review, 2/66, 46-54, beschreibt S-(3,5-Di-tert.-butyl-4-hydroxy-benzyl)-N,N-di-n-butyl-dithiocarbamat als Schmiermittelzusatz.
  • Es wurde nun gefunden, dass in Schmiermitteln überraschenderweise durch Zugabe eines kleinen Anteils an ausgewählten Phenol-N,N-dioctyldithiocarbaminsäureestern eine noch verbesserte Antioxydations- und Antikorrosionswirkung erzielt werden kann. Diese Verbindungen, die keinen Metallsalzcharakter haben, sind zudem frei von den durch Bildung von Rückständen entstehenden Nachteilen.
  • Die vorliegende Erfindung betrifft demgemäss Schmiermittel, die als Stabilisator eine Verbindung der Formel
    Figure imgb0001
    enthalten, worin
    • R C1-C12 Alkyl, C5-C7 Cycloalkyl, gegebenenfalls durch C1-C6 Alkyl substituiertes C6-C10 Aryl, CI-C22 Aralkyl,
    • R1 und R2 jeweils unabhängig voneinander H oder R bedeuten und
    • R3 Octyl ist.
      • R ist als C1-C12 Alkyl verzweigtes oder unverzweigtes Alkyl, wie Methyl, Aethyl, n-Propyl, Isopropyl, n-Butyl, tert.-Butyl, n-Pentyl, a-Methylpentyl, Hexyl, 2,4-Dimethylpentyl, Octyl, 6-Methylheptyl, 2-Aethylhexyl, Decyl, Dodecyl. Bevorzugt sind Alkylgruppen mit 1-8, insbesondere aber solche mit 1-4 C-Atomen.
      • R ist als C5-C7 Cycloalkyl, Cyclopentyl, Cyclohpetyl und insbesondere Cyclohexyl.
      • R ist als gegebenenfalls durch C1-C6 Alkyl substituiertes C5-C10 Aryl gegebenenfalls mehrmals jedoch insbesondere einmal durch lineares oder verzweigtes C1-C6 Alkyl substituiertes Phenyl oder Naphthyl, wie beispielsweise Methylphenyl oder Methylnaphthyl. Dabei handelt es sich insbesondere um p-substituiertes Phenyl oder in 4-Stellung substituiertes 1-Naphthyl, vorzugsweise jedoch um unsubstituiertes Phenyl oder 1-Naphthyl.
      • R ist als C7-C22 Aralkyl Phenalkyl oder Naphthalkyl, wobei der Alkylteil jeweils aus verzweigtem oder unverzweigtem C1-C12 insbesondere jedoch C1-C4 Alkyl besteht. Bevorzugte Aralkylreste sind a-Phenäthyl und insbesondere Benzyl.
  • Die Dithiocarbamatgruppe ist in o- oder insbesondere in m- oder p-, jedoch bevorzugt in p-Stellung zur Hydroxylgruppe an den Phenolring gebunden.
  • Hervorzuheben sind Schmiermittel, die als Stabilisator eine Verbindung der Formle I enthalten, worin
    • R und R1 C1-C8 Alkyl, Phenyl oder Benzyl und
    • R2 Wasserstoff oder C1-C8 Alkyl sind und
    • R3 Octyl bedeutet,

    wobei die Dithiocarbamatgruppe in m- oder p-Stellung zur Hydroxylgruppe des Phenols steht.
  • Von ganz besonderem Interesse sind Schmiermittel, die als Stabilisator eine Verbindung der Formel IV
    Figure imgb0002
    enthalten, worin
    • R und R1 C1-C4 Alkyl und
    • R2 Wasserstoff oder Methyl sind.
  • Bevorzugt sind Schmiermittel, die als Stabilisator eine Verbindung der Formel
    Figure imgb0003
    enthalten, worin R und R1 C1-C4 Alkyl bedeuten.
  • Ebenfalls bevorzugt sind Schmiermittel, die als Stabilisator eine Verbindung der Formel
    Figure imgb0004
    enthalten, worin R und R1 C1-C4 Alkyl sind.
  • Gegenstand der Erfindung sind auch Verbindungen der Formel
    Figure imgb0005
    worin R-C1-C1Z Alkyl, C5-C7 Cycloalkyl, gegebenenfalls durch C1-C6 Alkyl substituiertes C6-C10 Aryl, C7-C22 Aralkyl und R1 und R2 jeweils unabhängig voneinander H oder R bedeuten.
  • Die erfindungsgemäss zu verwendenden Hydroxybenzyl-N,N-dioctyl-dithiocarbamate können nach allgemein bekannten Methoden erhalten werden, indem man beispielsweise Mono- oder Di-Chlormethylphenole der Formeln
    Figure imgb0006
    mit den äquivalenten Mengen entsprechender Na-dithiocarbamate der Formel
    Figure imgb0007
    in einem inerten Lösungsmittel wie Acetonitril, Toluol, Aether oder Chloroform unter Abspaltung von NaCI umsetzt.
  • Die ortho- und insbesondere die para-Hydroxybenzyl-dithiocarbamate sind in der vorstehend für die meta-Derivate zitierten Weise analog erhältlich, bevorzugt werden sie aber nach bekannten Methoden hergestellt durch Reaktion molarer Mengen eines entsprechenden substituierten Phenols der Formel.
    Figure imgb0008
    mit Formaldehyd, Schwefelkohlenstoff und einem Amin der Formel
    Figure imgb0009
  • Die Verbindungen der Formel wirken schon in sehr geringen Mengen als Stabilisatoren gegen Oxidations- und Korrpsionswirkung in Schmiermitteln. So zeigen mineralische und synthetische Schmieröle, sowie deren Gemische, welche 0,001 bis 5 Gew.-% bezogen auf das Schmiermittel, und vorzugsweise 0,02-3% einer Verbindung der Formel I enthalten, ausgezeichnete Schmiereigenschaften, welche durch stark reduzierte Abnutzungserscheinungen der zu schmierenden Reibpartner deutlich werden.
  • Die in Frage kommenden Schmiermittel sind dem Fachmann geläufig und z.B. im "Schmiermittel-Taschenbuch" (Hüthig Verlag, Heidelberg, 1974) beschrieben. Besonders geeignet sind Mineralöle.
  • Die Schmierölformulierung kann zusätzlich noch andere Additive enthalten, die zugegeben werden, um gewisse Gebrauchs-Eigenschaften zu verbessern, wie Antioxidantien, Metallpassivatoren, Rostinhibitoren, Viskositätsindex-Verbesserer, Stockpunkterniedriger, Dispergiermittel/Tenside und andere Verschleissschutz-Additive.
    • Beispiele für Antioxidantien sind:
    • a) Alkylierte und nicht-alkylierte aromatische Amine und Mischungen davon, z.B.: Dioctyldiphenylamin, (2,2,3,3-Tetramethyl-butyl)-phenyl-cr- und-ß-naphthylamine, Phenothiazin, Dioctylphenothiazin, Phenyl-a-naphthylamin, N,N'-Di-sec.-butyl-p-phenylendiamin.
    • b) Sterisch gehinderte Phenole, z.B.: 2,6-Di-tert.-butyl-p-cresol, 4,4'-Bis-(2,6-diisopropylphenol)-, 2,4,6-Triisopropylphenol, 2,2'-Thio-bis-(4-methyl-6-tert.-butyl-phenol), 4,4'-Methylen-bis-(2,6-di-tert.-butylphenol).
    • c) Alkyl-, Aryl- oder Alkaryl-phosphite z.B.: Trinonylphosphit, Triphenylphosphit, Diphenyldecylphosphit.
    • d) Ester von Thiodipropionsäure oder Thiodiessigsäure, z.B.; Dilaurylthiodipropionat oder Dioctylthiodiacetat.
    • e) Kombination von zwei oder mehr Antioxidantien der obigen, z.B.: ein alkyliertes Amin und ein sterisch gehindertes Phenol.
    Beispiele für Metallpassivatoren sind
    • a) für Kupfer, z.B.:
      Benzotriazol, Tetrahydrobenzotriazol, 2-Mercaptobenzotriazol, 2,5-Dimercaptothiadiazol, Salicylidenpropylendiamin, Salze von Salicylaminoguanidin.
    • b) für Blei, z.B.:
      Sebacinsäurederivate, Chinizarin, Propylgallat,
    • c) Kombination von zwei oder mehr der obigen Additive.
    Beispiele für Rost-Inhibitoren sind
    • a) Stickstoffhaltige Verbindungen, z.B.:
      • I. Primäre, sekundäre oder tertiäre aliphatische oder cycloaliphatische Amine und Amin-Salze von organischen und anorganischen Säuren, z.B. öllösliche Älkylammoniumcarboxylate.
      • 11. Heterocyclische Verbindungen z.B.: Substituierte Imidazoline und Oxazoline.
    • b) Phosphorhaltige Verbindungen, z.B.:
      • Aminsalze von Phosphorsäurepartialestern,
    • c) Schwefelhaltige Verbindungen, z.B.:
      • Barium-dinonylnaphthalin-sulfonate, Calciumpetroleumsulfonate,
    • d) Kombinationen von zwei oder mehr der obigen Additive.
    Beispiele für Viskositätsindex-Verbesserer sind
  • Polymethacrylate, Vinylpyrrolidon-Methacrylat-Copolymere, Polybutene, Olefin-Copolymere, Styrol/Acrylat-Copolymere.
    • Beispiele für Stockpunkterniedriger sind
  • Polymethacrylate, alkylierte Naphthalinderivate.
  • Beispiele für Dispergiermittel/Tenside sind Polybutenylbernsteinsäure-imide. Polybutenylphosphonsäurederivate, basiche Magnesium-, Calcium-, und Bariumsulfonate und -phenolate.
    • Beispiele für andere Verschleissschutz-Additive sind
  • Schwefel und/oder Phosphor und/oder Halogen enthaltende Verbindungen, wie geschwefelte vegetabilische Oele, Zinkdialkyldithiophosphate, Tritolyl-phosphat, chlorierte Paraffine, Alkyl- und Aryldisulfide.
  • Die Herstellung der in den erfindungsgemässen Schmiermitteln als Stabilisatoren zu verwendenden Verbindungen, sowie die Verwendung und Wirkung der erfindungsgemässen Schmiermittelzusammensetzungen wird in den folgenden Beispielen näher beschrieben.
    • Herstellungsbeispiele Beispiel 1: S-(3-Hydroxy-4-tert.-butyl-2,6-dimethylbenzyl)-N,N-di-n-octyldithiocarbamat.
  • 34 g N,N-Di-n-octyldithiocarbarninsäure-Natriumsalz werden in 300 ml Acetonitril gelöst und unter Rühren bei 10°C innert 30 Minuten mit einer Lösung von 22,7 g 3-Hydroxy-4-tert.-butyl-2,6-dimethyl-benzyl-chlorid (Darstellung siehe Makromolekulare Chemie, Band 9 (1952), Seiten 21/22) in 50 ml Toluol versetzt. Das Reaktionsgemisch wird dann ca. 15 Stunden bei 20-25°C gerührt, wobei eine Natriumchlorid-Abscheidung zu beobachten ist.
  • Anschliessend wird das Gemisch in ca. 1 Liter Eiswasser eingegossen, die Toluolphase nach Zugabe von weiteren 100 ml Toluol abgetrennt, mit Wasser ausgeschüttelt, über Calciumchlorid getrocknet und im Vakuum eingedampft. Das S-(3-Hydroxy-4-tert.-butyl-2,6-dimethylbenzyl)-N,N-di-n-octyl-dithiocarbamat bleibt als bräunliches viskoses Oel zurück und ist für den Einsatz als Stabilisator bereits genügend rein und elementar-analytisch sowie chromatographisch weitgehend einheitlich.
  • Weitere Hydroxybenzyldithiocarbamate, das erfindungsgemäss zu verwendende Di-n-octyl-(Beispiel 2) und die zu vergleichenden Di-n-butyl- (Beispiel 3) Derivate sind in der folgenden Tabelle aufgeführt. Sie werden nach bekannten Methoden, vorzugsweise durch Umsetzen entsprechender Phenole (Kolonne 2 der Tabelle) mit Formaldehyd, Schwefelkohlenstoff und dem entsprechenden sekundären Amin (Kolonne 3 der Tabelle) erhalten (z.B. nach US-PS 2,757,174).
    Figure imgb0010
    • Anwendungsbeispiele Beispiel 5: Oel-Oxidations-Test, Standard Version nach ASTM D 2272 (Rotary Bomb Oxidation Test)
  • Eine Oelprobe von 50 ml "Rotary-Vacuum-Oil" der Fa. SHELL (Viskosität 11 cSt./100°0* wird unter Zusatz von 0,25 g Stabilisator in einem Glasgefäss zusammen mit 5 ml dest. Wasser und einer blankpolierten, mit Petroläther gewashenen katalytisch werikenden Cu-Spirale in einer SauerstoffAtmosphäre oxydiert.
  • Das Glasgefäss befindet sich in einer Bombe aus rostfreiem Stahl mit Manometer. Die Bombe dreht sich axial mit 100 U/Min. in einem Winkel von 30° zur Horizontalen, in einem Oelbad bei 150°C. Der Sauerstoffdruck beträgt anfangs, vor dem Aufheizen ca. 6 Atm (90 psi), steigt bei 150°C auf knapp 14 Atm (200 psi) und bleibt bis zur einsetzenden Oxidation konstant. Die Prüfung ist beendet bei einem Druckabfall um 1,7 Atm (25 psi). Aufgezeichnet wird die Zeit in Minuten.
  • Zum Wirkungsvergleich wurden in die Prüfserie aufgenommen:
    Figure imgb0011
    • Beispiel 6 Oel-Oxidationstest nach IP 280, "CIGRE"
    • Modifizierte Version mit löslichem Cu- und Fe-Katalysator.
    • Bedingungen: 4 Stunden Sauerstoff einleiten bei 150°C (4 Liter O2/h).
    • Bestimmung der Säurezahl nach Testende; Tabebellenwert: mg KOH-Verbrauch pro g Testöl.
    • Stabilisatorkonzentration: 0,5%
    • Testöl: Shell Rotary Vakuum Oil (Viskosität 11 cSt./100°C).
      Figure imgb0012
    Beispiel 7 Prüfung der Wirkung als Oxidations- und Korrosionsschutzmittel in Gasturbinenöl nach Methode FTMS 5308. C
    • Bedingungen: Lufteinleiten 3 Tage bei 174°c
    • Stabilisatorkonzentration: 0,5%
    • Testöl: Shell Rotary Vacuum Oil (Viskosität 11 cSt./100°C).
      Figure imgb0013

Claims (12)

1. Schmiermittel enthaltend als Stabilisator eine Verbindung der Formel I
Figure imgb0014
worin
R C1-C12 Alkyl, C5-C7 Cycloalkyl, gegebenenfalls durch C1-C6 Alkyl substituiertes C6-C10 Aryl, C7-C22 Aralkyl,
R1 und R2 jeweils unabhängig voneinander H oder R bedeuten und
R3 Octyl ist.
2. Schmiermittel gemäss Anspruch 1, dadurch gekennzeichnet, dass sie als Stabilisator eine Verbindung der Formel I enthalten, worin
R und R1 C1-C8 Alkyl, Phenyl oder Benzyl und R2 Wasserstoff oder C1-C8 Alkyl sind und
R3 Octyl bedeutet,

wobei die Dithiocarbamatgruppe in m- oder p-Stellung zur Hydroxylgruppe des Phenols steht.
3. Schmiermittel gemäss Anspruch 1, dadurch gekennzeichnet, dass sie als Stabilisator eine Verbindung der Formel IV
Figure imgb0015
enthalten, worin
R-und R1 C1-C4 Alkyl und
R2 Wasserstoff oder Methyl sind.
4. Schmiermittel gemäss Anspruch 1, dadurch gekennzeichnet, dass sie als Stabilisator eine Verbindung der Formel
Figure imgb0016
enthalten, worin
R und R1 C1-C4 Alkyl bedeuten.
5. Schmiermittel gemäss Anspruch 1, dadurch gekennzeichnet, dass sie als Stabilisator eine Verbindung der Formel
Figure imgb0017
enthalten, worin
R und R1 C1-C4 Alkyl sind.
6. Schmiermittel gemäss Anspruch 1, dadurch gekennzeichnet, dass sie als Stabilisator S-(3-Hydroxy-4-tert.-butyl-2,6-dimethylbenzyl)-N,N-di-n-octyl-dithiocarbamat enthalten.
7. Schmiermittel gemäss Anspruch 1, dadurch gekennzeichnet, dass sie als Stabilisator S-(3,5-Di- tert.-butyl-4-hydroxybenzyl)-N,N-di-n-octyl-dithiocarbamat enthalten.
8. Verwendung von Verbindungen der Formel I als Stabilisatoren von Schmiermitteln gemäss Anspruch 1.
9. Verwendung von Verbindungen der Formel 1 als Stabilisatoren von Mineralölen gemäss Anspruch 1.
10. Verbindungen der Formel
Figure imgb0018
worin R C1-C12 Alkyl, C5-C7 Cycloalkyl, gegebenenfalls durch C1-C6 Alkyl substituiertes C6-C10 Aryl, C7-C22 Aralkyl und R1 und R2 jeweils unabhängig voneinander H oder R bedeuten.
EP78100387A 1977-07-21 1978-07-13 Phenol-N, N-dioctyl-dithio-carbaminsäureester und damit stabilisierte Schmiermittel Expired EP0000514B1 (de)

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US4734210A (en) * 1985-07-30 1988-03-29 Ciba-Geigy Corporation Additives for lubricant compositions
US4836942A (en) * 1988-06-06 1989-06-06 Ethyl Petroleum Additives, Inc. Lubricant composition
EP0376889B1 (de) * 1988-12-28 1993-05-19 Ciba-Geigy Ag Schmierstoffzusammensetzung
US5370806A (en) * 1989-12-21 1994-12-06 Mobil Oil Corporation Borated dihydrocarbyl dithiocarbamate lubricant additives and composition thereof
US5560853A (en) * 1990-08-30 1996-10-01 Pennzoil Products Company Dithiocarbamoyl diols and borate esters thereof for use in lubricant compositions
US5254275A (en) * 1991-12-12 1993-10-19 Exxon Research And Engineering Company Lubricating oil containing an O-alkyl-N-alkoxycarbonylthionocarbamate (PNE-633)
US6046144A (en) * 1997-06-02 2000-04-04 R.T. Vanderbilt Co., Inc. Combination of phosphate based additives and sulfonate salts for hydraulic fluids and lubricating compositions
US7112558B2 (en) 2002-02-08 2006-09-26 Afton Chemical Intangibles Llc Lubricant composition containing phosphorous, molybdenum, and hydroxy-substituted dithiocarbamates
US7741257B2 (en) 2005-03-15 2010-06-22 Ecolab Inc. Dry lubricant for conveying containers
US7745381B2 (en) * 2005-03-15 2010-06-29 Ecolab Inc. Lubricant for conveying containers
US7727941B2 (en) * 2005-09-22 2010-06-01 Ecolab Inc. Silicone conveyor lubricant with stoichiometric amount of an acid
US7915206B2 (en) * 2005-09-22 2011-03-29 Ecolab Silicone lubricant with good wetting on PET surfaces
US7741255B2 (en) * 2006-06-23 2010-06-22 Ecolab Inc. Aqueous compositions useful in filling and conveying of beverage bottles wherein the compositions comprise hardness ions and have improved compatibility with pet
CN103119143A (zh) 2010-09-24 2013-05-22 艺康美国股份有限公司 包括乳液的输送机润滑剂和使用它们的方法
SG193366A1 (en) * 2011-03-10 2013-10-30 Lubrizol Corp Lubricating composition containing a thiocarbamate compound
WO2014164468A1 (en) 2013-03-11 2014-10-09 Ecolab Usa Inc. Lubrication of transfer plates using an oil or oil in water emulsions
CN105601551B (zh) * 2014-11-24 2017-08-22 中国石油化工股份有限公司 一种含硫受阻酚类化合物及其制备方法和应用
CN104611094B (zh) * 2015-01-30 2017-02-22 西安热工研究院有限公司 一种汽轮机油复合抗氧剂及其制备方法与添加方法
CN111040823B (zh) * 2020-01-02 2022-06-28 济南佳进新材料有限公司 抗磨剂、其应用、其制备方法、无灰液压油组合物及其制备方法

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GB966224A (en) * 1960-10-06 1964-08-06 Canadian Ind Hydroxybenzyl dithiocarbamates and stabilization of olefine polymers
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NL298236A (de) 1962-09-24
FR1482630A (fr) * 1965-06-09 1967-05-26 Us Rubber Co Composés chimiques à action fongicide ou bactéricide pour l'agriculture ou l'industrie
GB1125900A (en) 1966-08-30 1968-09-05 Ici Ltd Stabilisation of resin
US3412026A (en) * 1966-12-12 1968-11-19 Shell Oil Co Lubricant compositions containing dithiocarbamates
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