DE1643959B1 - Antioxydationsmittel - Google Patents

Antioxydationsmittel

Info

Publication number
DE1643959B1
DE1643959B1 DE19671643959 DE1643959A DE1643959B1 DE 1643959 B1 DE1643959 B1 DE 1643959B1 DE 19671643959 DE19671643959 DE 19671643959 DE 1643959 A DE1643959 A DE 1643959A DE 1643959 B1 DE1643959 B1 DE 1643959B1
Authority
DE
Germany
Prior art keywords
butyl
phenol
tert
weight
bis
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
DE19671643959
Other languages
English (en)
Inventor
O'neill James Dennis
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.)
Ethyl Corp
Original Assignee
Ethyl Corp
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 Ethyl Corp filed Critical Ethyl Corp
Publication of DE1643959B1 publication Critical patent/DE1643959B1/de
Pending legal-status Critical Current

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    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
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    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
    • C08K5/57—Organo-tin compounds
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Description

Diese Erfindung betrifft ein Antioxydationsmittel, insbesondere einen antioxydativen Stabilisator für Schmieröle auf Mineralölbasis.
Bekannt sind gehinderte phenolische Antioxydationsmittel zur Stabilisierung organischer Stoffe. Beispielsweise ist die Stabilisierung von organischen Stoffen mit 4,4-Methylen-bis-(2,6-di-tert.butyl-phenol) in der deutschen Patentschrift 1237 246 offenbart. Andere phenolische Stabilisatoren sind in der deutschen Patentschrift 1145 630 und in der USA.-Patentschrift 2 364 338 offenbart.
Weiterhin sind Diakylzinnsulfide als Stabilisatoren für Schmieröle in der USA.-Patentschrift 3 077 451 offenbart.
Es wurde nunmehr gefunden, daß die Kombination eines gehinderten phenolischen Antioxydationsmittels mit einem Dihydrocarbylzinnsulfid zu einer überraschenden synergistischen Wirkung führt, die von der Einzelwirkung ihrer Bestandteile her nicht erwartet werden konnte.
Gegenstand der Erfindung ist ein Antioxydationsmittel, insbesondere ein Mittel für die antioxydative Stabilisierung von Schmierölen auf Mineralölbasis, aus
(A) 4,4'-Methylen-bis-(2,6-di-tert.-butyl-phenol),
4,4'-Thio-bis-(2-methyl-6-tert.-butyl-phenol)
oder 4,4'-Thio-bis-(2,6-di-tert.-butyl-phenol) in einer Menge von 1 bis 99 Gewichtsprozent und
(B) Dibutylzinnsulfid in einer Menge von etwa 1 bis 99 Gewichtsprozent.
Das erfindungsgemäße Gemisch wird dem zu stabilisierenden Schmieröl in einer Menge von beispielsweise 0,001 bis 5 Gewichtsprozent, vorzugsweise 0,001 bis 3 Gewichtsprozent, zugegeben.
Die nachfolgenden Beispiele und Zahlenangaben erläutern die Vorteile der Erfindung an Hand eines Kohlenwasserstoffschmieröls. Als Untersuchungsverfahren wurde der Panel Coker Test verwendet (vgl. »Aeronautical Standards of the Departments of Navy and Air Force«, Spec. MIL-L 7808 C, 2.11.1955). Bei dem Test wird ein lösungsmittelraffiniertes, neutrales Kohlenwasserstoffschmieröl in eine Wanne unter eine auf 288° C erhitzte Metallplatte eingegeben. Das Öl wird periodisch gegen die erhitzte Platte gespült, worauf man es in die Wanne zurücktropfen läßt. Man spült das Öl 5 Sekunden und läßt es 55 Sekunden abtropfen. Dies wird 10 Stunden lang wiederholt. Nach dieser Zeit wird die Metallplatte mit Hexanen abgewaschen und die Gewichtszunahme bestimmt. Eine
Additiv Konzen
tration
(7o)		 Ablage
rung
(mg)
4,4'-Methylen-bis-(2,6-di-
tert.-butyl-ph.enol)
Dibutylzinnsulfid
Dibutylzinnsulfid
4,4'-Methylen-bis-(2,6-di-
tert.-butyl-phenol) +
Dibutylzinnsulfid 		1
0,1
0,5
1
0,1		 143
22
13
4
Wie diese Zahlen zeigen, tritt bei 0,1 °/0 Dibutylzinnsulfid eine Ablagerung von 22 mg auf. Wird die Menge des Dibutylzinnsulfids um das Fünffache, auf 0,5 °/o erhöht, so nimmt das Gewicht der Ablagerung nur auf 13 mg ab. Überraschenderweise ergibt die Kombination von 0,1 °/0 Dibutylzinnsulfid mit l°/0 4,4'-Methylen-bis-(2,6-di-tert.-butyl-phenol) ein Ablagerungsgewicht von nur 4 mg. Dies, trotz der Tatsache, daß 1% 4,4'-Methylen-bis-(2,6-di-tert.-butyl-phenol) selbst zu 143 mg Ablagerung führt.
Weitere Untersuchungen wurden unter Verwendung von Phenolen mit Schwefel-Brückenbindung durchgeführt. Die untersuchten Kombinationen enthielten 4,4'-Thiobis-(2,6-di-tert.-butyl-phenol) und 4,4'-Thiobis-(2-methyl-6-tert.-butyl-phenol), beide zusammen mit Dibutylzinnsulfid. Es wurden nachfolgende Ergebnisse erhalten.
Tabelle!!
45 Additiv
4,4'-Thiobis-(2,6-di-tert.-butyl-
phenol)
4,4'-Thiobis-(2-methyl-6-tert.-
butyl-phenol)
di-Butylzinnsulfid
4,4'-Thiobis-(2,6-di-tert.-butyl-
phenol)
di-Butylzinnsulfid
4,4'-Thiobis-(2-methyl-6-tert.-
butyl-phenol)
di-Butylzinnsulfid
di-Butylzinnsulfid
4,4'-Thiobis-(2,6-di-tert.-butyl-
phenol)
di-Butylzinnsulfid
4,4'-Thiobis-(2,6-di-tert.-butyl-
phenol)
65 Aus der Tabelle II ist zu ersehen, daß 1 °/0 4,4'-Thiobis-(2-methyl-6-tert.-butyl-phenol) zu 16 mg Ablagerung und 0,1 % di-Butylzinnsulfid zu 22 mg Ab
0,5
Ablagerung
(mg)
1 16 J- 37 1
0,1 22 } 8 137 [ 4
1 4 I
0,1
1
0,1
0,5
0,5
0,5
lagerung führen. Die Kombination der beiden ergab ein Schmiermittel, das nur 8 mg Ablagerung bildete.
Noch deutlicher sind die Ergebnisse, die mit 4,4'-Thiobis-(2,6-di-tert.-butyl-phenol) erhalten wurden. l°/0 dieses Materials ergibt ein Schmieröl mit einer Ablagerung von 6 mg. Wird dieses Material mit 0,1 °/0 Dibutylzinnsulfid kombiniert, das selbst eine Schmierölablagerung von 22 mg ergibt, so wird ein hochstabiles Öl erhalten, das nur 4 mg Ablagerung ergibt. "Wenn die Menge an 4,4'-Thiobis-(2,6-di-tert.-butylphenol) und Dibutylzinnsulfid um 50°/0 verringert wird, werden nur 4 mg Ablagerung erhalten.
Diese Versuche zeigen, daß die synergistisch wirkenden, stabilisierenden Gemische der vorliegenden Erfindung die thermische und oxydative Stabilität des
Schmieröls wesentlich erhöhen. Die vorliegenden Gemische sind deshalb wirksame Stabilisatoren für Schmiermittel auf KW-Basis.
Schmiermittel, bei welchen die Stabilisatoren der Erfindung anwendbar sind, umfassen öle oder Fette auf Basis mineralischer Kohlenwasserstoffe oder siliciumhaltige Stoffe, wie Siloxane, Silane und Silicatester, Fluorkohlenstoffe, Diester, aromatische Äther, Phosphatester, Polyalkylenglycole, synthetische Kohlenwasserstoffe, z. B. Polybutene oder andere Polyolefinöle niederen Molekulargewichts und Tetrahydrofuranpolymerisate. Das erfindungsgemäße Antioxydationsmittel ist auch zur Stabilisierung anderer funktioneller Flüssigkeiten, von Kunststoffen, Kautschuk und dergleichen organischen Materialien brauchbar.

Claims (1)

  1. Patentanspruch:
    Antioxydationsmittel, bestehend aus
    (A) 4,4'-Methylen-bis-(2,6-di-tertiär-butyl-phenol), 4,4'-Thio -bis-(2-methyl-6-tertiär-butyl-phenol) oder 4,4'-Thio-bis-(2,6-di-tertiär-butyl-phenol) in einer Menge von 1 bis 99 Gewichtsprozent und
    (B) Dibutylzinnsulfid in einer Menge von 1
    99 Gewichtsprozent.
    bis
    IO
    Gewichtszunahme ist auf ein thermisches und oxydatives Zusammenbrechen des Öles zurückzuführen, bei dem eine kohlenstoffhaltige Ablagerung zurückbleibt. Die ersten Versuchsreihen wurden durchgeführt, wobei als Stabilisatoren Dibutylzinnsulfid, 4,4'-Methylenbis-(2,6-di-tert.-butyl-phenol) und die Kombination von beiden verwendet wurde. Das Gewicht der gebildeten Ablagerung ist in der nachfolgenden Tabelle aufgezeigt.
    Tabelle I
    15
DE19671643959 1966-12-22 1967-12-07 Antioxydationsmittel Pending DE1643959B1 (de)

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US4701486A (en) * 1981-02-26 1987-10-20 Morton Thiokol, Inc. Stabilizer compositions for PVC resins
US4314934A (en) * 1981-02-26 1982-02-09 Carstab Corporation Organohalide polymers stabilized with an organotin compound and an ortho mercapto phenol compound
US4576984A (en) * 1982-02-04 1986-03-18 Morton Thiokol, Inc. Stabilizer compositions for PVC resins
US4822833A (en) * 1986-03-10 1989-04-18 Ciba-Geigy Corporation Stabilized rigid polyvinyl chloride compositions
US5039437A (en) * 1987-10-08 1991-08-13 Exxon Chemical Patents, Inc. Alkyl phenol-formaldehyde condensates as lubricating oil additives
US5032634A (en) * 1988-12-02 1991-07-16 Akzo America Inc. Stabilized vinyl halide resins and stabilizer combination
US5284886A (en) * 1989-10-31 1994-02-08 Elf Atochem North America, Inc. Non-toxic polymeric compositions stabilized with organosulfide antioxidants

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DE1217382B (de) * 1960-04-11 1966-05-26 Ethyl Corporation, New York, N. Y. (V. St. A.) Stabilisieren von Motortreibstoffen, Schmierölen, oder -fetten auf Kohlenwasserstoffbasis oder von polymeren Kohlenwasserstoffen

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