DE1279270B - Esterschmiermittel - Google Patents

Esterschmiermittel

Info

Publication number
DE1279270B
DE1279270B DES95904A DES0095904A DE1279270B DE 1279270 B DE1279270 B DE 1279270B DE S95904 A DES95904 A DE S95904A DE S0095904 A DES0095904 A DE S0095904A DE 1279270 B DE1279270 B DE 1279270B
Authority
DE
Germany
Prior art keywords
phenothiazine
alkyl
clear
dioctyl
weight percent
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
DES95904A
Other languages
English (en)
Inventor
Alexander Colquhoun B Macphail
Littele Sutton
Francis Henry Waight
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 DE1279270B publication Critical patent/DE1279270B/de
Pending legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/62—Use of additives, e.g. for stabilisation
    • C—CHEMISTRY; METALLURGY
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    • 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
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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
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • 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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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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    • C10M2207/22—Acids obtained from polymerised unsaturated acids
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    • C10M2207/287—Partial esters
    • C10M2207/288—Partial esters containing free carboxyl groups
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    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
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    • C10M2207/304—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl groups
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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 79 270.0-43 (S 95904)
11. März 1965
3. Oktober 1968
Kombinationen von Phenothiazinen und sekundären aromatischen Aminen sind aus der USA.-Patentschrift 2 930 758 bekannt. Bei diesen Phenothiazinen aber handelt es sich um solche, welche entweder nur im Kern oder nur am N-Atom substituiert sind. Es wurde nun gefunden, daß die Oxydationsbeständigkeit von Schmierölen wesentlich verbessert werden kann, wenn man diesen eine Kombination zusetzt, welche ein Kern- und N-substituiertes Phenothiazin der Formel
Esterschmiermittel
in der R ein Ci 8-AlkyI-, Phenyl-, Tolyl-, Benzyl- oder Cyanoalkylrest ist und die Reste Ri bis Ri Wasserstoff, Alkyl- oder Alkoxygruppen sind, wobei mindestens einer dieser Reste eine Alkyl- oder Alkoxygruppe ist, enthält.
Die erfindungsgemäß anzuwendenden N-substituierten Phenothiazine enthalten eine Alkyl- oder Alkoxygruppe als Substituent in jedem aromatischen Ring, der das Phenothiazinmolekül mitaufbaut, wobei eine Substitution in 3,7-Stellung besonders bevorzugt ist. Die Herstellung solcher N-substituierter Phenothiazine wird beispielsweise in der britischen Patentschrift 873 066 beschrieben. Für die Zwecke der vorliegenden Erfindung sind die nachstehend aufgeführten N-substituierten Phenothiazine besonders geeignet: 10 - Methyl - 3,7 - dioctyl - phenothiazin, lO-n-Butyl-SJ-dioctyl-phenothiazin, 10-n-Octyl-3,7-dioctyl-phenothiazin, lO-Phenyl-Sj-dioctyl-phenothiazin, 10-Tolyl-3,7-dioctyl-phenothiazin, 10-Cyanoäthyl-3,7-dioctyl-phenothiazin, 10-Cyanopropyl-3,7-dioctyl-phenothiazin, lO-CyanobutyWJ-dioctylphenothiazin, 10-Benzyl-3,7-dioctyl-phenothiazin, 10-Benzyl-3,7-dibutyl-phenothiazin, 10-Benzyl-3,7-diisopropoxy-phenothiazin, 10-Benzyl-3,7-dibutoxyphenothiazin und Mischungen dieser Verbindungen.
Obwohl im Rahmen der vorliegenden Erfindung an sich jedes beliebige sekundäre aromatische Amin mit den N-substituierten Phenothiazinen kombiniert werden kann, werden doch bestimmte Diphenylamine und N-Arylnaphthylamine bevorzugt. Sehr geeignete Diphenylamine sind solche mit einer Alkyl- oder Alkoxygruppe, welche 4 bis 20 Kohlenstoffatome aufweist, als Substituent bei wenigstens einem aromatischen Kern in der para-Stellung. Disubsti-Anmelder:
Shell Internationale Research Maatschappij N. V., Den Haag (Niederlande)
Vertreter:
Dr. E. Jung und Dr. V. Vossius, Patentanwälte,
8000 München 23, Siegesstr. 26
Als Erfinder benannt:
Francis Henry Waight, Mold, Flintshire;
Alexander Colquhoun Barr MacPhail,
Little Sutton, Wirral, Cheshire (Großbritannien)
Beanspruchte Priorität:
Großbritannien vom 11. März 1964 (10 263),
vom 19. Juni 1964 (34 930),
vom 26. August 1964 (25 466),
vom 27. Oktober 1964 (43 747),
vom 26. Februar 1965
tuierte Diphenylamine werden bevorzugt, insbesondere eignet sich ρ,ρ'-Dioctyldiphenylamin. Beispiele für N-Arylnaphthylamine, die an wenigstens einem der aromatischen Ringe durch eine oder mehrere Alkylgruppen mit insgesamt bis zu 20 Kohlenstoffatomen substituiert sein können, sind Phenylalpha-naphthylamin, Phenyl-beta-naphthylamin und beta, beta-Dinaphthylamin. Hierbei wird Phenylalpha-naphthylamin besonders bevorzugt. Wenn bei den erfindungsgemäßen Zusammensetzungen das als Basis dienende Esterschmiermittel einen einfachen Ester darstellt, so werden vorzugsweise Diphenylamine, wie ρ,ρ'-Dioctyl-diphenylamin, insbesondere zusammen mit N-Arylnaphthylaminen, als das sekundäre aromatische Amin verwendet. Wenn dagegen Polyester als Basisschmiermittel eingesetzt werden, so erscheint es vorteilhaft, N-Arylnaphthylamine, wie Phenyl-alpha-naphthylamin, anzuwenden.
Die erfindungsgemäßen Phenothiazine und sekundären, aromatischen Amine werden jeweils in Mengen von 0,05 bis 10, insbesondere von 0,1 bis 5 Gewichtsprozent, dem Schmieröl zugesetzt.
Als Basisschmieröle können einfache Ester, komplexe Ester, Polyester oder Gemische dieser Esterkomponenten verwendet werden, denen je nach den
809 619537
gewünschten Viskositätseigenschaften der Endgemische und den Temperaturbedingungen, unter welchen sie angewendet werden, auch noch Verdickungsmittel zugesetzt werden können.
Die Esterschmieröle können außerdem noch andere übliche Zusätze, z. B. Höchstdruckmittel, Antioxydationsmittel, Metalldesaktivatoren, Antikorrosionsmittel, Antischaummittel, Farbstoffe, enthalten.
Zur näheren Erläuterung der Erfindung wurden Esterschmiermittel mit der in Tabelle I angegebenen Zusammensetzung hergestellt (Beispiele I bis III und Vn sowie VIII) und dann mit bekannten Esterschmiermitteln, (Beispiele IV bis VI und IX sowie X) mittels einer der drei nachstehenden Teste verglichen, nämlich eines Oxydations-Korrosionstests bei 175° (vgl. US. Military Specification MIL-L-7808 D), eines Lagerungstests bei tiefer Temperatur und eines beschleunigten Lagerungstests. Bei den Lagerungstesten wurden Proben der erfindungsgemäßen Zusammensetzungen bzw. der nicht der Erfindung entsprechenden Esterschmiermittel in Behältern mit nur lose aufliegenden Verschlüssen gelagert, welche-auf Temperaturen von 15 bzw. 80°C gehalten und nach gewissen Zeitabständen bis zu 3 Monaten bezüglich der Bildung von suspendierten Substanzen geprüft wurden.
Tabelle I
Zusammensetzungen gemäß den Beispielen I bis X
I II t III IV V VI VII VIII X
94,0 94
93,2 — — 93,2 — — 93,2 30,2 93,2
— - — — — — — — 34,0 —
— — 14,5 — t 14,5 — —· —
— —. 58,0 — — 58,0 — — —
1,5 1,5 '1,5 — — J 1,3 1,3 —
— — — 1,5 1,5 1,5 — — 1,3
1,5 1,5 1,5 1,5 1,5 1,5 1,5 1,5 1,5
1,0 2,0· 1,0 2,0 1,0 — 1,0
— 25 25 — 25 25 — — —
25 — — 25 — — 25 25 25 .
0,02 0,02 0,02 0,02 0,02 0,02 0,02 — 0,02
- 3 —
Di-(2-äthylhexyl)-sebacat, Gewichtsprozent
Diisooctylazelat, Gewichtsprozent Diisodecylazelat, Gewichtsprozent ....
2,2,4-Trimethylpentylazelat, Gewichtsprozent
Trimethylolpropantripelargonat,
Gewichtsprozent
lO-Benzyl-SJ-dioctyl-phenothiazin, Gewichtsprozent
3,7-Dioctyl-phenothiazin, Gewichtsprozent
Phenyl-a-naphthylamin, Gewichtsprozent -
Triphenylphosphorthionat, Gewichtsprozent
5-Methylbenzotriazol
3-Amino-5-anilido-l,2,4-triazol
Azelainsäure, Gewichtsprozent
Polymer von 3,3'-Bis-(chlormethyl)-oxetan (Molekulargewicht 450, Cl-Gehalt 45%), Gewichtsprozent
Tabelle II
Flüchtigkeit Erhöhung der Erhöhung Cu Veränderungen im Metallgewicht mg/cm2 Al Fe
Beispiel Verlust in Säurezahl der Viskosität 0 Ag 0 0
Gewichtsprozent mg KOH/g % -0,10 Mg 0 0 -0,02
I 0,8 1,25 12,0 -0,03 0 0,12 0 0
II 0,6 1,5 12,2 -0,04 0 +0,02 0 -0,02
III 0,4 0,5 2,6 0 0 0 0 -0,02
IV 0,7 1,20 11,8 -0,02 0 -0,3 0 0
V 1,2 1,5 12,6 +0,12 0
VI 0,4 0,4 2,5 +0,02
Grenzen ±0,4 ±0,2 —►
gemäß
Vorschrift — 2,0 —5 zu «—
+ 15
Aus Tabelle II ist ersichtlich, daß die erfindungs- keit bei hoher Temperatur aufweisen, welche mindegemäßen Gemische der Beispiele I bis III alle eine stens so gut wie diejenige der Vergleichsmischungten Oxydationsbeständigkeit und Korrosionsbeständig- gemäß den Beispielen IV bis VI ist, wobei das Ester-
schmiermittel gemäß Beispiel I eine ganz besonders gute Oxydations- und Korrosionsbeständigkeit bei hoher Temperatur zeigt.
Aus der nachstehenden Tabelle III ergibt sich weiterhin, daß nur die erfindungsgemäßen Esterschmiermittel gemäß den Beispielen I bis III und VII bzw. VIII ein befriedigendes Verhalten bei den beiden Lagerungstesten zeigen. Vier Proben der Gemische gemäß den Beispielen VII bis X wurden außerdem über 1 Jahr lang dem Lagerungstest bei tiefer Temperatur (15°C) unterworfen und im Abstand von jeweils einigen Wochen bezüglich der Bildung von suspendiertem Material geprüft. Alle Proben mit einer Zusammensetzung gemäß den Beispielen VII und VIII blieben unter diesen Lagerungsbedingungen vollständig klar und hell, während das Verhalten von Proben der Vergleichsbeispiele IX und X variierte: Eine Probe jedes Beispiels blieb klar, andere Proben jedes Beispiels bildeten schon nach den ersten wenigen Tagen des Lagertestes Niederschläge, während alle anderen Proben noch vor Beendigung der Prüfzeit Niederschläge bildeten.
Tabelle III
15° C 3 Wochen Zustand der Proben nach 5 Wochen klar 7 Wochen klar 8 Wochen 12 Wochen klar
Beispiel 3 Monaten 80° C klar klar klar klar
klar — — wolkig — Ablagerungen klar - — · mittlere
I klar — — — klar — Ablagerungen
II klar — — Ablagerungen — mittlere wolkig — schwere
III wolkig —' — — Ablagerungen weiße — Ablagerungen
IV wolkig Teilchen
V — — — wolkig —
wolkig klar —
VI — klar —
VII — klar —
VIII —
IX wolkig —
—
X
Für die Zwecke der vorliegenden Erfindung geeignete N-cyanoalkylsubstituierte Phenothiazine enthalten bis zu 20 Kohlenstoffatome und vorzugsweise 2 bis 8 Kohlenstoffatome in der Alkylkette des Cyanoalkylrestes, und sie weiun ferner vorzugsweise eine Alkyl- oder Alkoxygruppe an jedem das Phenothiazinmolekül aufbauenden aromatischen Ring auf, wobei eine Substitution in 3,7-Stellung bevorzugt wird. Beispiele für derartige Phenothiazine sind 10-Cyanoä&yI-3,7-dioctyl-phenothiazin, 10-Cyanopropyl-SJ-dioctyl-phenothiazin und 10-Cyanobutyl-3,7-dioctyl-phenothiazin.

Claims (1)

  1. Patentanspruch:
    Esterschmiermittel, enthaltend eine bekannte Kombination aus einem substituierten Phenothiazin und einem sekundären aromatischen Amin, welches zwei aromatische Gruppen direkt an das Stickstoffatom gebunden enthält, dadurch gekennzeichnet, daß es ein Kern- und N-substituiertes Phenothiazin der Formel
    sAx!R2
    in der R ein Ci-8-Alkyl-, Phenyl-, Tolyl-, Benzyl- oder Cyanoalkylrest ist und die Reste Ri bis R4 Wasserstoff, Alkyl- oder Alkoxygnippen sind, wobei mindestens einer dieser Reste eine Alkyl- oder Alkoxygruppe ist, enthält.
    In Betracht gezogene Druckschriften:
    USA.-Patentschrift Nr. 2 930 758.
    809 6U/537 9. M φ Bundcsdruckerei Berlin
DES95904A 1964-03-11 1965-03-11 Esterschmiermittel Pending DE1279270B (de)

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GB10263/64A GB1036695A (en) 1964-03-11 1964-03-11 Improvements in or relating to ester base compositions
GB2546664 1964-06-19
GB3493064 1964-08-26
GB4374764 1964-10-27

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FR (1) FR1432875A (de)
GB (1) GB1036695A (de)
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US3539515A (en) * 1968-04-03 1970-11-10 Mobil Oil Corp Lubricating oil compositions containing peroxide-treated phenothiazine as an antioxidant
US3869394A (en) * 1971-06-11 1975-03-04 Grace W R & Co Lubricant composition and method
US3912727A (en) * 1972-11-22 1975-10-14 Grace W R & Co Preparation of phenothiazines
GB1421381A (en) * 1973-05-11 1976-01-14 Exxon Research Engineering Co Antioxidants
US4203854A (en) * 1974-02-20 1980-05-20 The Ore-Lube Corporation Stable lubricant composition containing molybdenum disulfide and method of preparing same
US5157118A (en) * 1986-09-16 1992-10-20 The Lubrizol Corporation N-substituted thio alkyl phenothiazines
US4785095A (en) * 1986-09-16 1988-11-15 The Lubrizol Corporation N-substituted thio alkyl phenothiazines
US5178784A (en) * 1986-09-16 1993-01-12 The Lubrizol Corporation N-substituted thio alkyl phenothiazines
US5034019A (en) * 1988-06-23 1991-07-23 The Lubrizol Corporation N-substituted thio alkyl phenothiazines
US5211862A (en) * 1986-12-31 1993-05-18 Ciba-Geigy Corporation Substituted N-thiomethylphenothiazines as lubricant stabilizers
DE3883048D1 (de) * 1987-04-08 1993-09-16 Ciba Geigy Ag Schwefelhaltige verbindungen als antioxidantien fuer schmiermittel und elastomere.
US4798684A (en) * 1987-06-09 1989-01-17 The Lubrizol Corporation Nitrogen containing anti-oxidant compositions
US5024774A (en) * 1987-06-09 1991-06-18 The Lubrizol Corporation Nitrogen containing anti-oxidant compositions
US4915858A (en) * 1987-06-09 1990-04-10 The Lubrizol Corporation Nitrogen containing anti-oxidant compositions
US5269954A (en) * 1988-12-05 1993-12-14 Elf France Nitrogenous additives with an antioxidant action and lubricating compositions containing the said additives
GB2272000B (en) * 1992-10-30 1997-03-26 Castrol Ltd A method of inhibiting corrosion
US5798321A (en) * 1995-05-23 1998-08-25 Exxon Research And Engineering Company Rust resistant turbo oils containing monobasic amino phosphates and dicarboxylic acids
US6797677B2 (en) 2002-05-30 2004-09-28 Afton Chemical Corporation Antioxidant combination for oxidation and deposit control in lubricants containing molybdenum and alkylated phenothiazine

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BE557513A (de) * 1956-05-14
US3014888A (en) * 1957-12-20 1961-12-26 Shell Oil Co Stabilized hydrocarbon compositions
BE573997A (de) * 1957-12-20
NL247300A (de) * 1959-01-14
FR1296477A (fr) * 1960-08-09 1962-06-15 British Petroleum Co Mélange lubrifiant
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NL6503025A (de) 1965-09-13
CH459427A (de) 1968-07-15
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BE660935A (de) 1965-09-13
MY6700034A (en) 1967-12-31
NO120647B (de) 1970-11-16
FR1432875A (fr) 1966-03-25
US3344068A (en) 1967-09-26

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