DE2140683A1 - Synthetisches Grundmaterial fur Schmiermittel und funktionell Fluide - Google Patents

Synthetisches Grundmaterial fur Schmiermittel und funktionell Fluide

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Publication number
DE2140683A1
DE2140683A1 DE19712140683 DE2140683A DE2140683A1 DE 2140683 A1 DE2140683 A1 DE 2140683A1 DE 19712140683 DE19712140683 DE 19712140683 DE 2140683 A DE2140683 A DE 2140683A DE 2140683 A1 DE2140683 A1 DE 2140683A1
Authority
DE
Germany
Prior art keywords
alcohol
alcohols
mixture
acid
base materials
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
DE19712140683
Other languages
English (en)
Inventor
Colin Dr Cheadle McGuigan Brian Dr Timperley Cheshire Staley (Großbritannien)
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.)
Novartis AG
Original Assignee
Ciba Geigy AG
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 Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of DE2140683A1 publication Critical patent/DE2140683A1/de
Pending legal-status Critical Current

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Description

Dr. F. Zumstein sen, - Pr. E. Assrnann Dr. R. Koenigsberger - ΡίρΙ.-Phys. R. Holzbauer - Dr. F. Zumstelrv Jun.
PATENTANWÄLTE
TELEFON: SAMMEL-MR. 225341
TELEX 529979
TELEGRAMME: ZUMPAT POSTSCHECKKONTO: MÜNCHEN 01139
BANKKONTO: BANKHAUS H. AUFHÄUSER
8MÜNCHEN2,
BRÄUHAUSSTRASSE 4/III
3-3379/HA 14-57*
CIBA-GEIGY A." G., CH- 4002 Basel /'Schweiz
Synthetisches Grundmaterial für Schmiermittel und
funktionelle Fluide
Die vorliegende Erfindung betrifft neue chemische Zusammensetzungen und insbesondere Trimellitbsäureester, die als synthetische Schmiermittel oder funktionelle Fluide geeignet sind.
Es wurden verschiedene Vorschläge zur Herstellung billiger synthetischer Carbonsäureester, die für die Verwendung als Grundmaterialien für funktionelle Fluide geeignet sind, gemacht. Zum Beispiel wurden o-Phthalsäure- und Isophthalsäure-ester dahingehend untersucht, ob sie für diesen Verwendungszweck geeignet sind. Diese beiden Esterarten sind ^ecloch für diesen Zweck dadurch nicht vollständig geeignet, da sie relativ niedrige Viskositäten, einen niedrigen Viskositätsindex, hohe Stockpunkte und hohe Flüchtigkeit aufweisen.
Hinzu kommt, daß die o-Phthalate dazu neigen, während der Verwendung unter Bildung des flüchtigen festen Phthalsäureanhydrids abgebaut zu werden, was eine höchst unerwünieli^Eigenschaft darstellt. Die Verwendung- von Alkoholen mit "'höherem Molekulargewicht zur Erhöhung der Viskosität der o~Phthalate und
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der Isophthalate führt zu Produkten mit höheren Stockpunkten, wogegen die Herstellung von komplexen Estern zu dem gleichen -Zweck, aus z.B. Glykolen und Alkohol, zu einer verminderten Verträglichkeit mit Mineralölen und Hineralöladditivsn rührt.
Es wurde nun gefunden, daß gewisse Alkylester der Triiiiellithsäure eine gute Kombination von Viskositäis/Pemperatiir-Eigenschäften mit einem niedrigen Stockpunkt ermöglichen, ade frei von Anwendungsnachteilen ist, wie sie "bei o-Phthalaten auftreten. V/eiterhin besitzen diese Materialien ausreichend hohe Viskositäten, so daß sie für die Verwendung als Schmiermittel in Benzinverbrennungsmotoren und als Fluide in automatischen Getrieben geeignet sind, wobei diese guten Viskositätseigenschaften mit niedrigen Stockpunkten und einer niedrigen Flüchtigkeit kombiniert sind.
Demzufolge stellt die vorliegende Erfindung ein Grundmaterial für ein synthetisches Schmiermittel oder ein funktionelles Fluid zur Verfugung, das einen Carbonsäureester der Trimelli ölsäure oder dessen Anhydrid mit einem oder mehreren aliphatischen Alkoholen mit 6 bis 11 Kohlenstoffatomen in der Alkylkette umfasst. .
Der in der vorliegenden Beschreibung verwendete Ausdruck "funktionelles Fluid" ist in der Art auszulegen, wie er in der Schmiermittelbranche allgemein verstanden wird. So verwenden die Schmiermittelfachleute den generischen Ausdruck "funktionelles Fluid" in der Weise, daß Materialien, wie Getz-iebefiuids und hydraulische Fluids, umschlossen, sind.
Beispiele von aliphatischen Alkoholen, die bei der Herstellung der Trimellitihsäureester geeignet sind, schließen Isohexylalkohol, Isoheptylalkohol, Isooctylalkohol, 3i5,5-Trimethylh.exylalkohol, Isodecylalkohol und Isoundecylalkohol ein. Bevorzugtere Alkoholausgangsmaterialien sind geradketfcige Alkohole, wie n-Hexylalkohol, im Plandel erhältliche Mischungen von Alkoholen mit 6 bis 11 Kohlenstoffatomen in der Alkylkette, wie "Alfol 610", eine Mischung von Cg-> Gg- und C-Q-Alkoholen,
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_ 3 —
"Linevol 79" und "Linevol 911.% eine Mischung von Cn-, Gq- und Cq-Alkoholen, bzw. eine Mischung von C0-, C^q- und CL^-Alkoholen. Es können Mischungen von zwei oder mehr der obengenannten Alkohole verwendet werden.
Die Trimellitteäureester können nach an sich bekannten Verfahren hergestellt werden, wobei die Veresterung derart durchgeführt werden sollte, daß eine im vresentlichen vollständige Veresterung der Trimellitteäure oder dessen Anhydrid erreicht wird. Demzufolge ist es bevorzugt, daß mindestens die stöchioiüetrische Menge des Alkohols, die benötigt wird, um mit der Säure zu reagieren, verwendet wird, wobei bevorzugter ein wesentlicher Überschuß des Alkohols, z.B. ein molarer Überschuß von bis zu 20 Gew.-%, verwendet werden sollte.
Die Veresterungsreaktion kann geeigneterweise unter Rückfluß und in Gegenwart eines sauren Katalysators erfolgen. Geeignete Katalysatoren sind wäfo&rige Mineralsäuren, insbesondere Chlorwasserstoffsäure, Schwefelsäure und ο-Phosphorsäure, gasförmiger Chlorwasserstoff und organische Sulfonsäuren, z.B. p-Toluolsulfonsäure.
Das erfindungsgemäße Estermaterial kann in der letztendlichen Anwendung entweder allein oder vermischt mit anderen bekannten natürlichen oder synthetischen Materialien, z.B. Mineralölen und Carbonsäureestern, eingesetzt werden.
Das erfindungsgemäße Estermaterial kann gewünschtenfälls eine geringe Menge bekannter Additive, wie Antioxydantien, Metallkomplexierungsmittel, Metallpassivatoren, Rostinhibitoren, Viskositätsindexverbesserer, Stockpunkterniedriger, Dispergiermittel oder Detergentien, Hochdruckadditive oder Antiabriebadditive oder Antischaummittel enthalten.
Geeignete Antioxydantien schließen die in der britischen Patentschrift 1 046 353 beschriebenen tert.-Alkylphenyl-oc- und ß-naphthylamine und die in der britischen Patentschrift 1 180 385 beschriebenen Mischungen mit Dioctyldiphenylamin,
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oxydierte Amine, wie sie in de,r britischen Patentschrift (Patentanmeldung Nr. '17461/6S) der gleichen Anmelderin beschrieben sind, andere alkylierte und nicht-alkylierbe aromatische Amine und Mischungen davon, sterisch gehinderte Phenole, wie 2,6-Di-tert.-butyl-p~kresol, 4,4-'-Bis-(2,6-diiso~ propylphenol), 2,4,6-Triisopropylphenol und 2,2'-Thio~bis~(''!-~ methyl-6-tert.-butylphenol); Alkyl-, Aryl- oder Alkarylphosphite, wie Triphenylphosphite, Triarylphosphite und Diphenyldecylphosphit, Ester der Thiopropionsäure, 'z.B. Dilauryltbiodipropionat; Salze der Carbaminsäure oder der Dithiophosphon-säure, z.B. Antimondiamyldithiocarbamat und Zinkdiainyldithiophosphat und frei radikalische Antioxydantien und deren Vor- W läufer, wie Aminoxyde und Hitroxyde, .ein.
Beispiele geeigneter MetalIkomplexierungsmittel sind Metallsalze und Komplexe von organischen Chelatisierungsmitteln, wie Kupfer-bis-itrifluoracetylacetonate), Kupferphthalοcyanine und das Mononatriumsalz des Tributylesters der Ä'thylendiamintetraessigsäure.
Beispiele geeigneter Metallpassivatoren schließen die folgenden Typen ein:
(a) für Kupfer z.B.: Benztriazol, J^'
zol5 Tetrahydrobenztriazol, 2,5-Dimercapto-thiadiazol, Salicyliden-propylen-diamin und Salze von Salicylaminoguanidin^.
(b) für Blei z.B.: Sebacinsäure, Propy3SEQ.lat oder Chinizarin.
(c) Für Magnesium z.B.: Pyridylamine.
Ro st inhibit or en, die in den Schmiermittelzusaiamensetsungen verwendet werden können, schließen diejenigen der folgenden Gruppen ein:
(a) Organische Säuren und deren Ester, Metallsalze und Anhydride, z.B. N-Oleylsarcosin, Sorbitanmonooleat, Bleinophtlienat und Dodecenylbernsteinsäureanhydrid.
(b) Stickstoffhaltige Materialien, z.B.
20SS08/1759
(i) primäre, sekundäre oder, tertiäre aliphatisch^ oder cycloaliphatische Amine und Aminsalze von organischen und anorganischen Säuren, z.B. Morpholin, Stearylamin und Triäthanolamincaprylat.
(ii) heterocyclische Verbindungen, z.B. Imidazoline und Oxyzoline.
(c) Phosphorhaltige Materialien, z.B. anorganische Phosphate, Phosphonsäuren und Aminphosphate»
(d) Schwefelhaltige Materialien, z.B. Barium - Dinonylnaphthalinsulfonate.
Geeignete Viskositätsindexverbesserer oder Stockpunkterniedriger sind z.B. Polyacrylate, Polybutene und Polyvinylpyrrolidone.
Beispiele für Dispergiermittel oder Detergentien schließen Metall sulfonate, insbesondere Calcium-, Barium- und Magnesiumsalze, Metallphenate und" Polybutenylsuccinimide ein»
Hochdruckadditive oder Antiabriebadditive, die für die Verwendung in der Schmiermittelzusammensetzung geeignet sind, schliessen schwefel-und/oder phosphor-und/oder halogenhaltige Materialien, z.B. gulphurisiertes Spermöl, Tritolylphosphat und chlorierte Paraffine ein.
Silikone stellen besonders geeignete Antischaummittel dar»
Die erfindungsgemäßen Carbonsäureestergrundmaterialien sind billig herzustellen und besitzen' niedrige Stockpunkt-und Temperatur/Viskositäts-Eigenschaften, die sie für die Verwendung als Grundmaterialien für eine Vielzahl von synthetischen Schmiermitteln und funktionellen Fluiden äusserst geeignet machen.
Die folgenden Beispiele sollen die vorliegende Erfindung weiter erläutern, ohne sie jedoch zu beschränken. Gewichtsteile stehen in gleichem Verhältnis zu Volumenteilen wie Kilogramm zu Litern.
209808/1759
— 6 —
Beispie.'le 1 bis 3
A. Eine Mischung von 970 Teilen Trimellitsäureanhydrid, 2000 TeilenLinevol 79 ? einer im Handel erhältlichen Mischung von vorwiegend geradkettigen aliphatischen Alkoholen mit 7 bis 9 Kohlenstoffatomen, 6 Teilenp-Toluolsulf onsäure und 200 Teilet] Toluol wurden unter RiickXlußbedirigungen erhitzt, währenddem r/ian dac bei der Reaktion sich bildende Wasser kontinuierlich abtrennte. Die innere Temperatur der Mischung wurde, falls notwendig, durch weitere Toluolzugaben bei 135°C gehalten. In dem Moment, da sich kein Wasser mehr bildete, wurde das Erhitzen gestoppt, wobei an diesem Punkt der Säurewert der Reaktionsinssse niedriger als 5 mg K0H/gelag. Die Eeaktionsmischung wurde dann durch Abstreifen deSo Toluols,durch Waschen des Rückstandes mit wässriger Sodalösung, um die verbliebene Säure zu entfernen, und durch Behandlung mit Aktivkohle zur Verbesserung der Farbe, aufgearbeitet.·
In ähnlicher Weise wurden durch Ersatz des Linevol 79 durch eine äquivalente Menge Linevol 91^ bzw. Alfol 610 Trilinevol 911-Trimellithat(aus Linevol 911 hergestellt, das eine im Handel erhältliche Mischung von vorv?iegend geradkettigen aliphatischen Alkoholen mit 9 bis 11 Kohlenstoffatomen darstellt) bzw. Tri-Alfol 610 Trimelli&at (aus Alfol 610 gebildet, das eine im Handel erhältliche Mischung \wn geradkettigen aliphatischen Alkoholen mit 6 und 8 bis 10 Kohlenstoffatomen darstellt) bereitet.
B. Die so gebildeten Ester wurden untersucht und besaßen die im folgenden angegebenen physikalischen Eigenschaften:
209808/1759
Eigenschaft Ester Tri-Linevo1-
79-trimellitfoat		 Tri-Linevol-
911-trimelliifeat		 Iri-Alfol-
610 trimelliüiat		 Di-Linevol-79-
trineliaähat
Beispiel 1 Beispiel 2 Beispiel 3
Dichte 20/20°C «■ 0,987 0,961 0,975 -
Flammpunkt 0C (0F) 260 (500) 282 (540) . 285 (545) 235 (455) '
Viskosität 98,90C (21O0F)CS 7,53 9,79 8,00 4,39
Viskosität 37,80C (10O0E)CS 54,03 72,75 54,88 24,78
Viskositätsinäex 110 120 120 .92
ASTM Heisung 0,713 0,670 0,687 0,770
Stockpunkt 0C (0P) -53,9 (-65) -42,8 (-45) <-62. , (<-80) -51,1 (-60)
Säurewert mg KOH/g 0,05 0,05 0,03 0,06
Hydroxylwert mg KOH/g <0,5 <0,5 <0,5 ■ <0,5 .
O CD OO
J7ortSetzung der Tabelle
O CO CO O 00
Di-Linevo1 911 Ester Di-Dobanal-25-
isophthalat		 • -1,11 (+300I1;
Eigenschaft _ Di-AIf01-610-
ΐ sophthai at		 _
Dichte 20/200C 235 (505) _
Flammpunkt 0C (0JT) 5,92 263 (480) 8,05
Viskosität 98,9°C (2100F) CS 36,59 4,63 · 55,56.
Viskosität 37,8°C (10O0F) CS 114 26,20 119
Viskositätsindex • 0,725 101
ASTM Neigung -37,2 (-35) 0,757
Stockpunkt 0C (0F) 0,04 -51,1 (-60)
Säurewert mg KOH/g 0,5 -
Eydroxylwert mg KOH/g -
Jedes erfindungsgemäße Estergrundmaterial "besitzt Eigenschaften, die es für die Verwendung als funktioneiles Fluid geeignet machen. Insbesondere sind die Eigenschaften der erfindungsgemäßen Materialien denen bisher bekannter Ester, wie Isophthalaten, bezüglich der Viskositäts/Temperatur-Eigen«^haften überlegen.

Claims (5)

- 9 Patentansprüche
1. Grundmaterialien für synthetische Schmiermittel oder funktioneile Fluide, dadurch gekennzeichnet, daß sie einen Carbonsäureester der Trimellifchsäure oder dessen Anhydrid mit einem oder mehreren aliphatischen Alkoholen mit G "bis 11 Kohlenstoffatomen in der Alkylkette enthalten.
2. Grundmaterialien gemäß Anspruch 1, dadurch gekennzeichnet, daß der aliphatische Alkohol Isohexylalkohol, Isoheptylalkohol, Isooctylalkohol, 3r5>5-Trimethylhexylalkohol, Isodecylalkohol oder Isoundecylalkohol ist.
3. Grundmaterialien gemäß Anspruch 1, dadurch gekennzeichnet, daß der aliphatische Alkohol-n-Hexylalkohol oder eine, im Handel erhältliche Mischung von Alkoholen mit 6 bis 11 Kohlenstoffatomen in der Alkylkette ist. ' ·
4-, Grundmaterialien gemäß Anspruch· 3» dadurch gekennzeichnet, daß die Mischung der Alkohole eine Mischung von C/--, Cg- und C^Q-Alkoholen, eine Mischung von Cg-, C1-,- und Cq-Alkoholen oder eine Mischung von Cg-, ^λγΓ un<^ C..-Alkoholen ist.
5. Verwendung der Grundmaterialien gemäß einem der vor hergehenden Ansprüche für Getriebefluide oder hydraulische Fluide.
209808/1789
DE19712140683 1970-08-14 1971-08-13 Synthetisches Grundmaterial fur Schmiermittel und funktionell Fluide Pending DE2140683A1 (de)

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Publication number Priority date Publication date Assignee Title
GB8408017D0 (en) * 1984-03-28 1984-05-10 Bp Chem Int Ltd Oil-based lubricant compositions
US5068049A (en) * 1987-12-29 1991-11-26 Exxon Research & Engineering Company Method of cold rolling a metal
EP0351906B1 (de) * 1988-07-22 1992-09-16 Akzo N.V. Synthetische Schmierölzusammensetzung
DK3147317T3 (en) * 2015-09-28 2017-12-04 Evonik Degussa Gmbh TRIPENTYL ESTERS OF TRIMELLIC ACID

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