DE1112600B - Schmier- und Hydraulikoele - Google Patents

Schmier- und Hydraulikoele

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Publication number
DE1112600B
DE1112600B DER24969A DER0024969A DE1112600B DE 1112600 B DE1112600 B DE 1112600B DE R24969 A DER24969 A DE R24969A DE R0024969 A DER0024969 A DE R0024969A DE 1112600 B DE1112600 B DE 1112600B
Authority
DE
Germany
Prior art keywords
lubricating
hydraulic oils
esters
hydrogenated
carbon atoms
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
DER24969A
Other languages
English (en)
Inventor
Dr Ernst Koch
Walter Ludwig
Dr Fritz Kollinsky
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.)
Roehm and Haas GmbH
Original Assignee
Roehm and Haas GmbH
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 Roehm and Haas GmbH filed Critical Roehm and Haas GmbH
Priority to DER24969A priority Critical patent/DE1112600B/de
Priority to GB5652/60A priority patent/GB917001A/en
Priority to FR818724A priority patent/FR1248805A/fr
Publication of DE1112600B publication Critical patent/DE1112600B/de
Pending legal-status Critical Current

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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32Esters
    • C10M105/36Esters of polycarboxylic acids
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/03Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
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    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02Hydroxy compounds
    • C10M2207/023Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02Hydroxy compounds
    • C10M2207/023Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/027Neutral salts thereof
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/281Esters of (cyclo)aliphatic monocarboxylic acids
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2209/08Macromolecular 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
    • C10M2209/084Acrylate; Methacrylate
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    • C10M2217/02Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M2217/00Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
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    • C10M2219/104Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/108Phenothiazine
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  • Chemical & Material Sciences (AREA)
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  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Es ist bekannt, Dialkylester von Dicarbonsäuren, wie Adipinsäure und Sebacinsäure, als Schmiermittel zu verwenden. Dabei sind von besonderem Vorteil Ester, deren Alkoholkomponenten verzweigtkettig sind und 6 bis 14 Kohlenstoffatome enthalten. Auch Tricarbonsäureester, bei denen die Estergruppen an ganz oder zum Teil benachbarten Kohlenstoffatomen sitzen, sind für Spezialfälle als Schmiermittel geeignet.
Weiterhin wurde die Verwendung von Tricarbonsäureestern, die die drei Estergruppen an jeweils untereinander nicht benachbarten Kohlenstoffatomen gebunden enthalten und deren Alkoholkomponenten 6 bis 14 Kohlenstoffatome besitzen, als Schmiermittel vorgeschlagen.
Es wurde auch schon empfohlen, polymere Ester polymerisierbarer Monocarbonsäuren mit Alkylenglykolmonoäthern als Zusatz zu hydraulischen Flüssigkeiten zu verwenden.
Es wurde weiterhin bereits vorgeschlagen, solche Produkte als Schmier- und Hydrauliköle zu verwenden, die bei der Cyanäthylierung ein- oder mehrwertiger Alkohole mit Oligomerisierungsprodukten ungesättigter Nitrile und anschließender Verseifung und Veresterung der entstehenden gesättigten Nitrile mit höheren Alkoholen entstehen. Ester dieser Art weisen in der Hauptkette Äthersauerstoff auf und unterscheiden sich unter anderem darin von den im nachstehenden beschriebenen und erfindungsgemäß zu verwendenden Produkten.
Gemäß einem älteren, nicht vorveröffentlichten Vorschlag können Schmier- und Hydrauliköle auf Esterölbasis derart hergestellt werden, daß Aldehyd- oder Alkylenoxydcyanhydrine mit Nitrilen von Äthylencarbonsäuren in an sich bekannter Weise umgesetzt, die erhaltenen Cyanäthylierungsprodukte verseift und mit ein- oder mehrwertigen Alkoholen verestert werden. Auch diese Produkte weisen in der Hauptkette einen Äthersauerstoff auf.
Gegenstand der Erfindung ist die Verwendung von hydrierten Estern von Oligocarbonsäuren einer Acrylsäure (4 bis 10 COOH-Gruppen) mit gesättigten aliphatischen einwertigen C4- bis C12-Alkoholen, wobei sich die Estergruppen an jeweils untereinander nicht benachbarten C-Atomen befinden, als Schmier- und Hydrauliköle.
Als im Sinne der Erfindung zu verwendende Produkte kommen z. B. in Frage die Ester der Methacrylsäure, tetrameren, pentameren und hexameren Methacrylsäure. Besonders günstige Eigenschaften weisen die oligomeren Ester auf, deren Alkoholkomponenten zum überwiegenden Teil geradkettig sind.
Schmier- und Hydrauliköle
Anmelder:.
Röhm & Haas G. m. b. H.,
Darmstadt, Mainzer Str. 42
Walter Ludwig, Bensheim-Auerbach,
Dr. Ernst Koch, Traisa über Darmstadt,
und Dr. Fritz Kollinsky, Darmstadt-Eberstadt,
sind als Erfinder genannt worden
Die oligomeren Ester können durch Hydrierung des oligomeren Methylesters und nachfolgende Alkoholyse mit einem oder mehreren höheren unverzweigten dieser Alkohole erhalten werden. Die oligomeren Säuren ihrerseits können gemäß den in den deutschen Patentschriften 903 932 und 855 554 beschriebenen Verfahren erhalten werden. Die Herstellung kann auch durch Veresterung der freien Säure mit den entsprechenden Alkoholen oder durch Oligomerisierung eines monomeren Methacrylsäureesters mit einer Alkoholkomponente mit 4 bis 12 Kohlenstoffatomen und anschließende Hydrierung erfolgen. Unter Hydrierung soll keine katalytische Reduktion, sondern eine Anlagerung von Wasserstoff an die in den Oligomeren noch vorhandene Doppelbindung verstanden werden.
Der umseitigen Tabelle sind die Daten der im Sinne der Erfindung zu verwendenden Ester zu entnehmen.
Gegenüber den bekannten Schmierölen zeichnen sich die erfindungsgemäßen Produkte durch einen höheren Flammpunkt und eine höhere Viskositätslage aus, was für verschiedene Anwendungsgebiete, z. B. für die Schmierung unter extrem hohen Temperaturbedingungen, gefordert wird. Wegen ihrer hohen Viskositätslage sind die Produkte z. B. als Bestandteil zu Syntheseölen mit niedrigerer Viskositätslage gut geeignet.
109 677/192
Die einzelnen oligomeren Ester können jeweils für Verhalten verbessernden Produkten erwiesen. Auf
sich allein oder im Gemisch miteinander oder mit diese Weise läßt sich noch eine weitere Verbesserang
anderen Schmierstoffen undSchmierstoffzusätzenver- der in der vorstehenden Tabelle angeführten Daten
wendet werden. Als vorteilhaft hat sich der Zusatz und- somit eine Vergrößerung des Anwendungsbe-
von an sich bekannten, das Temperatur-Viskositäts- 5 reiches der Schmier- und Hydrauliköle erzielen.
Ester
Hydrierter tetramerer Methacrylsäuretetra-n-butylester
Hydrierter tetramerer Methacrylsäuretetra-n-hexylester
Hydrierter tetramerer Methacrylsäuretri-n-decyl-isononylester
Hydrierter tetramerer Methacrylsäuretetra-n-decylester
Hydrierter tetramerer Methacrylsäuretetra-n-octylester
Hydrierter tetramerer Methacrylsäurepenta-n-octylester
Viskosität (cSt.)
37,8° C I 98,9° C
6,4 VJ. m-Wert Stockpunkt
0C
Flammpunkt
0C
40,7 6,6 108 3,62 -46 243
44,1 8,9 111 3,58 .... -50 257
64,3 8,7 119 3,40 -53 281
60,8 7,3 121 3,38 -48 278
50,6 9,6 113 3,53 -48 264
77,4 110 3,65 -45 284

Claims (1)

  1. PATENTANSPRUCH:
    Verwendung von Estern von hydrierten Oligocarbonsäuren einer Acrylsäure (4 bis 10 COOH-Gruppen) mit gesättigten aliphatischen einwertigen C4- bis C12-Alkoholen, wobei sich die Estergruppen an jeweils untereinander nicht benachbarten C-Atomen befinden, allein oder in Verbindung mit bekannten Schmier- und Hydraulikölen als Schmier- und Hydrauliköle.
    In Betracht gezogene Druckschriften: Industrial and Engineering Chemistry (1953), S. 1766 bis 1775.
    In Betracht gezogene ältere Patente: Deutsche Patente Nr. 1 074 796, 1078 723, 1085 632.
    © 109 677/192 8. 61
DER24969A 1959-02-17 1959-02-17 Schmier- und Hydraulikoele Pending DE1112600B (de)

Priority Applications (3)

Application Number Priority Date Filing Date Title
DER24969A DE1112600B (de) 1959-02-17 1959-02-17 Schmier- und Hydraulikoele
GB5652/60A GB917001A (en) 1959-02-17 1960-02-17 Improvements in or relating to lubricating and hydraulic compositions
FR818724A FR1248805A (fr) 1959-02-17 1960-02-17 Huiles lubrifiantes et hydrauliques

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DER24969A DE1112600B (de) 1959-02-17 1959-02-17 Schmier- und Hydraulikoele

Publications (1)

Publication Number Publication Date
DE1112600B true DE1112600B (de) 1961-08-10

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Family Applications (1)

Application Number Title Priority Date Filing Date
DER24969A Pending DE1112600B (de) 1959-02-17 1959-02-17 Schmier- und Hydraulikoele

Country Status (3)

Country Link
DE (1) DE1112600B (de)
FR (1) FR1248805A (de)
GB (1) GB917001A (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3278434A (en) * 1963-07-30 1966-10-11 Exxon Research Engineering Co Lubricant compositions containing thiodicarboxylic acid esters

Also Published As

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FR1248805A (fr) 1960-12-23
GB917001A (en) 1963-01-30

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