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DE1263212B - Esterschmieroel - Google Patents

Esterschmieroel

Info

Publication number
DE1263212B
DE1263212B DES85111A DES0085111A DE1263212B DE 1263212 B DE1263212 B DE 1263212B DE S85111 A DES85111 A DE S85111A DE S0085111 A DES0085111 A DE S0085111A DE 1263212 B DE1263212 B DE 1263212B
Authority
DE
Germany
Prior art keywords
oxetane
polymer
lubricating oil
ester lubricating
weight
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
DES85111A
Other languages
English (en)
Inventor
Alexander Colquhoun B Macphall
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 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 DE1263212B publication Critical patent/DE1263212B/de
Pending legal-status Critical Current

Links

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    • 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
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
    • C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D305/06—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/16—Cyclic ethers having four or more ring atoms
    • C08G65/18—Oxetanes
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—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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    • C10M2207/00—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
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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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
    • C10M2207/22—Acids obtained from polymerised unsaturated acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
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    • C10M2207/28—Esters
    • 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
    • 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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    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084—Acrylate; Methacrylate
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/108—Phenothiazine
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/041—Triaryl phosphates
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts thereof
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/02—Unspecified siloxanes; Silicones
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08—Resistance to extreme temperature
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • C10N2040/13—Aircraft turbines

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Lubricants (AREA)

Description

BUNDESREPUBLIK DEUTSCHLAND
DEUTSCHES
PATENTAMT
AUSLEGESCHRIFT
Int. Cl.:
ClOm
Deutsche KL: 23 c -1/01
Nummer: 1 263 212
Aktenzeichen: S 851111V c/23 c
Anmeldetag: 9. Mai 1963
Auslegetag: 14. März 1968
Esterschmieröl
Bekanntlich werden Esteröle zum Schmieren von Gasturbinen verwendet.
Diese Esteröle verhalten sich aber bei hoher Belastung vielfach nicht befriedigend. Daher werden diesen ölen Zusätze beigegeben.
Es wurde nun gefunden, daß Esteröle gegenüber hohen Drucken eine wesentliche Verbesserung aufweisen, wenn man ihnen ein Oxetanpolymeres mit nicht mehr als 10 sich wiederholenden Einheiten, das durch Polymerisation eines substituierten Oxetans der Formel
X3C
X,C
CH,
CH,
in welcher ein X Cl oder Br und das andere H, Cl oder Br bedeutet, hergestellt worden ist, zusetzt.
Besonders bevorzugt sind Oxetanpolymere, die sich von 3,3-Bis-(chlormethyl)-oxetan ableiten.
Die polymeren Hochdruckzusätze können in einfacher Weise durch Erhitzen des Monomeren (vorzugsweise in Abwesenheit von Luft) bei einer Temperatur hergestellt werden, die zur Einleitung der Polymerisation ausreicht. Eine genügende Polymerisationsgeschwindigkeit wird bei Temperaturen von etwa 200°C erhalten. Die Struktur des Polymeren ist nicht mit Sicherheit bekannt. Man nimmt aber an, daß eine Cyclisierung unter Bildung großer Ringe eintritt, welche Ätherbindungen aufweisen. Der Polymerisationsgrad wird so gewählt, daß sich ein Polymeres ergibt, das bei 200:C nicht nennenswert flüchtig ist und welches in den betreffenden Diestern ausreichend löslich ist.
Die Konzentration des Polymeren in dem Schmiermittel gemäß vorliegender Erfindung soll zwischen 0,5 und 10 Gewichtsprozent, vorzugsweise zwischen 1 und 5 Gewichtsprozent des fertigen Schmiermittelgemisches, liegen.
Beispiele von Diestern einer aliphatischen Dicarbonsäure sind Diisononylsebacat, Di-(2-äthylhexyl)-sebacat. Di - isooctylazelat, Di - (3,5,5 - trimethylhexyl) - adipat, 2 - Äthylhexyl - 3,5,5 - trimethylhexylsebacat und Di-(2,2,4-trimethylpentyl)-azelat. Gemische dieser Ester und gemischte Ester können ebenfalls als Basisöl verwendet werden. Gewünschtenfalls können diesen Estern auch noch übliche Verdickungsmittel, ζ. B. Polymere von Acrylsäureester, Äther von Polyoxyalkylenglykole oder komplexe Ester zugesetzt werden. Die beanspruchten Schmieröle können Anmelder:
»Shell« Research Limited, London
Vertreter:
Dr. E. Jung, Patentanwalt,
8000 München 23, Siegesstr. 26
Als Erfinder benannt:
Francis Henry Waight,
Alexander Colquhoun Barr Macphall,
Derek Southern, Wirral, Cheshire
(Großbritannien)
Beanspruchte Priorität:
Großbritannien vom 11. Mai 1962 (18 206),
vom 8. April 1963
aber auch noch andere übliche Zusätze, z. B. Antioxydationsmittel, wie Phenothiazin, oder Rostverhinderer, wie Metallsalze von Erdölsulfonaten, oder schaumhindernde Mittel, wie Silikon, oder E. P.-Mittel, wie organische Phosphat- oder Phosphitester, zugesetzt werden.
Die Herstellung von Oxetanpolymerisaten wird durch die folgenden Beispiele erläutert. Patentschutz wird hierfür jedoch nicht beansprucht.
B e i s ρ i e 1 1
245 g 3,3'-Bis-(chlormethyl)-oxetan wurden in einer Stickstoffatmosphäre bei 21O0C 11 Tage lang erhitzt. Während dieser Zeit änderte sich die Farbe des Reaktionsgemisches zu Bernsteingelb. Nicht umgesetztes Monomeres wurde aus dem Reaktionsgemisch abdestilliert. Der polymere Rückstand war eine bernsteinfarbene, viskose Flüssigkeit und wurde in technischen, denaturierten Alkohol ausgegossen. Die beiden Flüssigkeiten waren nicht mischbar. Das Gemisch wurde gerührt, und nachdem sich die Schichten vollständig getrennt hatten, wurde der Alkohol von dem Polymerisat abgegossen. Die letzten Spuren von Wasser und Alkohol wurden aus dem Polymerisat durch Destillation beim Druck einer Wasserstrahlpumpe entfernt. Das so hergestellte Polymere hatte ein durchschnittliches Molgewicht von 450 und einen Chlorgehalt von 44,9 Gewichtsprozent.
809 518,618
Beispiel 2
175 g 3,3'-Bis-(chlormethyl)-oxetan wurden wie im Beispiel 1 10 Tage lang am Rückfluß erhitzt. Das Produkt wurde dann wie folgt fraktioniert:
Siedebereich Gewicht CI-Gehalt
Fraktion
Gewichts
0C g prozent
A <84/15mmHg 67
B 120 bis 180/ 41 45,4
0,1 mm Hg
C 180/0,1 mm Hg- 31 45,4
270/5 μ Hg
D < 270/5 μ Hg 36 45,3
Die Fraktion A bestand aus nicht umgesetzten Monomerem. Die Fraktionen B, C und D waren überwiegend das Dimere, Trimere bzw. Tetramere.
Beispiel 3
Das im Beispiel 1 beschriebene Polymere wurde weiter mit einem Silbernitrat-Alkohol-Gemisch gewaschen, um freie Chloridionen zu entfernen.
Die Erfindung wird weiter erläutert durch Beispiele (4 bis 10), die in Tabelle I zusammengestellt sind. Zum Vergleich sind Gemische, welche kein Polymeres gemäß vorliegender Erfindung bzw. ein Gemisch aus chlorierten Di- und Polyphenylen enthalten, ebenfalls in die Tabelle aufgenommen worden; beschrieben in den Beispielen 11 bis 14.
Tabelle I
Zusammensetzung
Di-(2-äthylhexyl)-sebacat,
Gewichtsprozent
Di-isooctylazelat, Gewichtsprozent Azelainsäure, Gewichtsprozent .. Adipinsäure, Gewichtsprozent...
3,7-Dioctylphenothiazin,
Gewichtsprozent
Phenyl-a-naphthylamin,
Gewichtsprozent
5-Methylbenzotriazol, Teile pro
Million
Silikon (Antischaummittel)
Teile pro Million
3% des Polymeren vom
Beispiel
Gemisch aus chlorierten Di-
und Polyphenylen, Gewichtsprozent
Beispiele
97
0,02
97
0,02
94 0,02
1,5
1,5 25 5 2B 94
0,02
94
0,02
1,5
1,5
25
5
2D
94
0,02
1,5
1,5
25
5
3
97
— — 0,02
10 11
97
94 —
0,02 0,02
1,5 —
1.5 —
Lj
5 		—
1
12
13
94 0,02
94 0,02
25
Die Mischungen der Beispiele 4 bis 14 wurden geprüft in einer I. A. E.-31/4-Zoll-Getriebe-Schmiermittelprüfmaschine, wie beschrieben von M a η - so s i ο η in »J. Inst. Pet.«, 1952, 38, 633, unter Anwendung von B. S. S.-EN-34-Stahlzahnrädern. Die Ergebnisse sind, ausgedrückt in Kilogramm der Belastung, die bis zum Eintreten des Versagens beim jeweiligen Schmiermittel angewendet werden konnten, in der Tabelle II angegeben.
Tabelle II
60
60 Geschwindigkeit U/min 6000 Temperatur 0C 60 HO
Beispiel 24,95 2000 13,61 15,88
Nr. 40,82 20,41 18,14
11 110
5 27,22
34,02
65
60 Geschwindigkeit U/min 6000 Temperatur ''C 60 110
Beispiel 24,95 2000 13,61 15,88
Nr. 47,63 24,95 20,41
31,75 18,14 13,61
12 40,82 20,41 20,41
4 36,29 20,41 15,88
13 34,02 13,61 18,14
6 40,82 18,14 20,41
7 36,29 18,14 15,42
8
9 110
14 27,22
38,56
27,22
36,29
38,56
36,29
39,01
33,57
Tabelle II zeigt, daß die Schmiermittelgemische der vorliegenden Erfindung verbesserte Wirkungen ergaben gegenüber Mischungen, welche kein Poly-
meres der vorliegenden Erfindung bzw. einen handelsüblichen Hochdruckzusatz enthielten.

Claims (2)

Patentansprüche:
1. Esterschmieröl aus einer aliphatischen Dicarbonsäure mit 6 bis 20 Kohlenstoffatomen und einem verzweigten, aliphatischen, einwertigen Alkohol mit 6 bis 12 Kohlenstoffatomen, d a durch gekennzeichnet, daß es ein Oxetanpolymeres mit nicht mehr als 10 sich wiederholenden Einheiten, das durch Polymerisation eines substituierten Oxetans der Formel X3C CH,
X3C
CH,
in welcher ein X Cl oder Br und das andere H, Cl oder Br bedeutet, hergestellt worden ist, enthält.
2. Schmiermittel nach Anspruch 1, dadurch gekennzeichnet, daß es ein von 3,3-Bis-(chlormethyl)-oxetan abgeleitetes Polymeres enthält.
809 518/618 3.68 © Bundesdruckerei Berlin
DES85111A 1962-05-11 1963-05-09 Esterschmieroel Pending DE1263212B (de)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB18206/62A GB964672A (en) 1962-05-11 1962-05-11 Improvements in or relating to lubricants

Publications (1)

Publication Number Publication Date
DE1263212B true DE1263212B (de) 1968-03-14

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ID=10108477

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Application Number Title Priority Date Filing Date
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Country Link
US (1) US3275555A (de)
BE (1) BE632079A (de)
DE (1) DE1263212B (de)
GB (1) GB964672A (de)
NL (1) NL292528A (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3546118A (en) * 1968-11-25 1970-12-08 Phillips Petroleum Co Metal working operations and lubricants
GB8502458D0 (en) * 1985-01-31 1985-03-06 Exxon Chemical Patents Inc Lubricating oil composition

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2137782A (en) * 1935-07-16 1938-11-22 Lubri Zol Dev Corp Lubricating composition
BE522938A (de) * 1951-08-22
US2722340A (en) * 1954-09-02 1955-11-01 Hercules Powder Co Ltd 3,3-bis(chloromethyl)oxetane coated articles and method of coating
US2914540A (en) * 1957-07-05 1959-11-24 Hercules Powder Co Ltd Stabilization of monomeric 3, 3-bis(chloromethyl)-oxetane
BE576233A (de) * 1958-02-28
NL258114A (de) * 1959-11-19

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NL292528A (de)
GB964672A (en) 1964-07-22
BE632079A (de)

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