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DE2534921A1 - Verfahren zur herstellung einer detergensverbindung - Google Patents

Verfahren zur herstellung einer detergensverbindung

Info

Publication number
DE2534921A1
DE2534921A1 DE19752534921 DE2534921A DE2534921A1 DE 2534921 A1 DE2534921 A1 DE 2534921A1 DE 19752534921 DE19752534921 DE 19752534921 DE 2534921 A DE2534921 A DE 2534921A DE 2534921 A1 DE2534921 A1 DE 2534921A1
Authority
DE
Germany
Prior art keywords
alkenylsuccinic
reaction
compound
products
anhydride
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
DE19752534921
Other languages
English (en)
Inventor
Jun Harry John Andress
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.)
ExxonMobil Oil Corp
Original Assignee
Mobil Oil 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 Mobil Oil Corp filed Critical Mobil Oil Corp
Publication of DE2534921A1 publication Critical patent/DE2534921A1/de
Pending legal-status Critical Current

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    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
    • C10M133/58—Heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D263/12—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals containing only hydrogen and carbon atoms
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    • C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
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    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
    • 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
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • 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
    • C10N2040/25—Internal-combustion engines
    • C10N2040/252—Diesel engines
    • 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
    • C10N2040/25—Internal-combustion engines
    • C10N2040/252—Diesel engines
    • C10N2040/253—Small diesel engines
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy
    • 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

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Description

fATCNTA.JW-iLTE
DR. E. WIEGAND DIPL-ING. W. NIEMANN
DR. M. KÖHLER DIPL-ING. C GERNHARDT 9 S Ή 9 2 1
MÖNCHEN HAMBURG TEtEFON = 55 5476 8000 M O N CH E N 2, TELEGRAMME: KARPATENT MATHILDENSTRASSE 12 TELEX: 5 29 068 KARP D
5. August 1975
W. 42 360/75
Mobil Oil Corporation New York, 1I.Y. (V.St.A.)
Verfahren zur Herstellung einer Detergensverbindung
Die Erfindung bezieht sich auf Stickstoff enthaltende Produkte und ihre Verwendung als Detergentien oder Reinigungsmittel.
Die britische Patentschrift 964 409 offenbart ein Verfahren zur Herstellung von Schmiermittelzusatzstoffen durch Umsetzung eines Alkenylbernsxeinsäureanhydrides mit einem Ämin, das wenigstens eine Hydroxylgruppe enthält, z.B. Tris(hydroxyiiethyl)aninor:etlian, bei einer !Temperatur von 180 bis 25O0G. In dieser Patentschrift wird beschrieben, daß ein Amid, ein Imid oder ein Sster gebildet
9809/0970
werden kann. In der "britischen Patentschrift 1 031 ist die Reaktion zwischen einem polyolefineschen PoIybernsteinsäureanhydrid oder,-halogenid und einen h-vdroxylierten Amin wie Tris(hydroxymethyl)aminoinethan (im nachstehenden als 11TMAH" bezeichnet) beschrieben. Diese Produkte sind als Schmiermittel-Detergentien beschrieben.
Aus der US-Patentschrift 3 632 511 ist ein Zweistufenverfahren, bei dem eine Umsetzung zwischen einen olefinsubstituierten Bernsteinsäureacylierungsraittel und einem Alkylenpolyamin erfolgt, wonach das Reaktionsgemisch mit einem hydroxylierten Amin wie TKAM umgesetzt wird, bekannt. In der US-Patentschrift 3 576 743 wird die Umsetzung zwischen dem Alkenylbernsteinsäureanhydrid und einem mehrv/ertigen Alkohol beschrieben, wonach das sich ergebende Reaktionsprodukt mit einem hydroxylierten Amin wie SMAM umgesetzt wird. In diesen beiden US-Patentschriften wird das sich ergebende Produkt als Mischung aus verschiedenen Produkten betrachtet. Die Produkte sollen Dispergierungseigenschaften und Rostbeständigkeitseigenschaften für Schmiermittel und Brennstoffe haben.
Es wurde nun gefunden, daß eine Klasse neuer, als Schmiermittel-Detergentien geeigneter Reaktionsprodukte durch Umsetzung einer Alkenylbernsteinsäureverbindung mit Tris(hydroxymethyl)aminomethan bei einer Temperatur unterhalb 1800C hergestellt werden kann. Diese neuen Produkte haben eine Oxazolinstruktur, im Gegensatz zur Amid-, Imid- oder Esterstruktur, die gemäß der britischen Patentschrift 984 409 bei höheren Temperaturen hergestellt wird.
Gemäß vorliegender Erfindung wird deshalb ein Verfahren zur Herstellung einer Detergensverbindung durch Reaktion einer Alkenylbernsteinsaureverbindung mit Tris{hydroxy— methyl)aminomethan bei einer Temperatur von 100 bis 1750C geschaffen, wobei ein Reaktionsprodukt mit einer Oxazolinstruktur erhalten wird.
809809/0970
Diese Detergensverbindungen sind in organischen Zusammensetzungen sehr nützlich, weil sie nicht metallisch und frei von Asche sind. .,
Die Alkenylbemsteinsäureanhydride, die "bei der Umsetzung verwendet werden, werden normalerweise durch Umsetzung eines Olefins (vorzugsweise eines Olefins mit 8 bis 300, gewöhnlich 20 bis 300 Kohlenstoffatomen) mit einem Maleinsäureanhydrid hergestellt. Die Herstellung dieser Anhydride ist eine "bekannte Verfahrensweise. Die Anhydride können auch aus chlorierten Olefinen mit Maleinsäureanhydrid hergestellt werden, um das entsprechende Alkenylbernsteinsäureanhydrid zu erhalten. Sin anderes Verfahren zur Herstellung dieser Anhydride ist die katalytische Methode, "bei der das Olefin und das Maleinsäureanhydrid miteinander vermischt und über einen kurzen Zeitraum erhitzt werden und ein organisches Peroxyd hinzugefügt wird. Das Verfahren ist in der DS-OS 2 352 347 beschrieben. Statt Maleinsäureanhydrid zu verwenden, können andere Materialien eingesetzt werden, z.B. Maleinsäure oder Maleinsäurehalogenid, Fumarsäure, Itaconsäure oder -anhydrid, Citraconsäure oder -anhydrid. Als Olefin können Monoolefine und Polyolefine verwendet werden. Polymere solcher Olefine wie Propen, Buten, Isobuten, Hexen, Octen und dgl. liefern ausgezeichnete Heaktionsteilnehmer. Monomere und Oligomere der höheren Olefine wie Decen, Dodecen, Octadecen und Sicosen liefern ebenfalls geeignete Produkte. Mischungen von Olefinen oder ihren Polymeren können bei Reaktion mit der ungesättigten Säurekomponente gemischte Alkenylbernsteinsäureverbindungen ergeben und sind in gleicher Weise brauchbar. Die Alkenylbernsteinsäureanhydride mit höherem Molekulargewicht werden bevorzugt, insbesondere jene mit 20 bis Kohlenstoffatomen,
6G3BQ9/097CI
Das Amin ist Tris(hydroxymethyl)aminomethan (TIiAM). Es wird nicht als typisch für Aminreaktanten als Klasse angesehen, weil es ein Oxazolinreaktionsprodukt erzeugt.
"Üblicherweise werden 0,05 "bis 5 Mol Amin mit einem Mol Alkenylbernsteinsäureverbindung umgesetzt. Das TIiAlI wird mit der Alkenylbernsteinsäureverbindung bei einer Temperatur von 100 bis 175 0 umgesetzt. Die Reaktion, die gemäß der Erfindung hier von Interesse ist, läuft, wie folgt, ab (zur Veranschaulichung wird ein Verhältnis von 1:1 geY/ählt):
j? CH2OH
Alkenyl-CH—
CH2 £ CH2OH
-CH -C =
CH2-C-OH
0
Dieses Produkt hat funktioneüe Gruppen, die Re"aktionsstellen liefern können, zwei Methanol Gruppen und eine nicht verwendete Carboxylgruppe. Somit kann eine weitere Reaktion durch Zufügung eines zweiten Reaktionsteilnehmers zu der E-eaktionsmischung Produkte mit einzigartigen
Eigenschaften liefern. Obwohl diese Oxazolinderivate Schnierölen und Brennstoffen Detergenseigenschaften verleihen, sind ihre Derivate nach Reaktion mit Boraten, Phosphonaten und Aldehyden sogar noch wirksamere Detergentien. Solche Materialien sind in der DT-OS 2 534- 922 "beschrieben
Die Gegenwart der Oxazolinstruktur kann durch Infrarotspektroanalyse bestätigt werden. Die C=iT-Bindung der Oxazolinstruktur absorbiert in Infrarotbereich bei etwa 1670 cm" , und dies liefert ■
die Gegenwart des Oxazolins·
I67O cm" , und dies liefert eine leichte Kontrolle für
Die Produkte gemäß der Erfindung sind als Detergentien in vielen organischen flüssigkeiten für Industriezwecke wie Schmieröle, Mineralöle und synthetische Ester oder synthetische Kohlenwasserstofföle, Fette, Wärmeaustauschflüssigkeiten, Sransnissionsflüssigkeiten, Getriebeöle und Schiffsdieselöle sowie Treib- und Brennstoffe wie Benzin und Heizöle brauchbar. In diesen Zusammensetzungen können andere Zusatzstoffe wie zusätzliche Detergentien, Viskositänsverbesserungsmittel, Hochdruekzusatzmittel, Oxidationsstabilitätszusatzstoffe anwesend sein. Diese zusätzlichen Zusatzstoffe können Asche bilden oder keine Asche bilden, einschließlich Alkenylbernsteinsäureiniid von Alkylenpolyaminen, Metallsulfonaten, Ketallphenolaten oder Metallphosphordithioaten. Diese Zusammensetzungen können zwischen 0,05 bis 20 Gew.-^, vorzugsweise 0,1 bis 10 Gew.-^ von diesen Zusatzstoffen enthalten. Die Zusatzstoffe gemäß der Erfindung können in ähnlichen Mengen verwendet werden.
Die Erfindung wird nachstehend anhand von Beispielen näher erläutert. Teile und Prozentsätze sind auf das Ge-
609809/0970
wicht bezogen, soweit nichts anderes angegeben ist. per Ausdruck "Hol" mit Bezug auf Polyalkenylbernsteinsäureanhydrid bezieht sich bei Polyalkenylbernsteinsäureanhydrid auf das kombinierte Gewicht des Anhydrides, da das Anhydrid nicht umgesetztes Olefin enthalten kann.
Beispiel 1
Tris(hydroxymethyl)aminoniethan (24 g, 0,2 EoI) wurmit 170 g Poly(decenyl)bernsteinsäureanhydrid (llolekulargewicht etwa 1500) und 170 g eines Prozeßöles (Promor Mr. &) gemischt. Die Mischung wurde dann zwei Stunden lang auf 120° - HO0C, danach von 160 auf etwa 1750C vier btunden lang erhitzt, worauf sie drei Stunden lang bei 1600C bis 1700C unter einem Vakuum von 3 mm Hg zur Abdestillation gehalten wurde. Das flüssige Produkt wog 358 g und enthielt 0,87$ (gesamt) Stickstoff und 0,61$ (basischen) Stickstoff. Danach v/urde dieses Produkt mit Wasser gewaschen, und die Stickstoffanalyse wurde mit folgenden Ergebnissen wiederholt:
<fo Stickstoff (gesamt) 0,48 $ Stickstoff (basisch) 0,54
Dieses Produkt hatte Infrarotabsorptionsbanden bei 3360, 2920, 1665, 1465, 1380, 1200, 1050 und 720 cm"1. Die Gegenwart der Bande von mittlerer Stärke bei 1665 cm~~ ist ein Anzeichen für die egenwart der Oxazolinstruktur. Schultern (schwach) an der Bande bei 1730 cssT sind ein Anzeichen der C=O-Gruppen von Imiden bzw. Estern, wodurch die Gegenwart von geringen !!engen dieser als Nebenprodukte angezeigt wird.
609809/0970
Beispiel 2
In ein geeignetes Eeaktionsgefäß wurden 508,0 g (0,26 Mol) eines Polybutenylbernsteinsäureanhydrides, wobei die Polybutenylgruppe durchschnittlich, etwa 130 Kohlenstoffatome enthielt, und 31 g (0,26 Mol) TIiAi,! gegeben, und die Mischung wurde unter Rühren auf etwa 175°C erhitzt· Das Verdampfungswasser wurde während des Reaktionszeitraumes entfernt. Die Reaktion war beendet, wenn die Vasserentwicklung aufhörte. Die Reaktionsmischung wurde gefiltert und bei 1650C unter verringertem Druck abdestilliert; es ergab sich ein viskoses flüssiges Endprodukt.
Beispiel 3
In einem geeigneten Reaktionsgefäß wurden 500 g (0,25 Mol) des in Beispiel 2 verwendeten Polybutenylbernsteinsäureanhydrides und 60 g (0,5 Mol) TIiAM gemischt. Die Mischung wurde auf etwa 17O0C unter Rühren erhitzt und auf-- dieser Temperatur gehalten, bis die Wasserdampfentwicklung aufhörte. Die Reaktionsmisehung wurde gefiltert und wie in Beispiel 2 abdestilliert.
Bewertung der Produkte
Die Produkte der Beispiele 2 und 3 wurden in dem folgenden Test bewertet: ein Aluminiumzylinder wird durch
609609/0970
Strahlenenergie in einem geschlossenen Gefäß erhitzt. Die Oberflächentemperatur des Zylinders wird HO min lang (Dauer des Tests) auf 30O0C gehalten. Der Zylinder dreht sich bei 2 U/min in einem Ölbad und der sich auf dem Zylinder bildende dünne Ölfilm kommt mit einer Luft enthaltenden erhitzten Atmosphäre (15O0C) in Berührung, die die Oxidation des Filmes und Oxidationsablagerurigen verursacht. Das Testschmiermittel v/ird gemäß der auf der Zylinderoberfläche gebildeten Ablagerungsmenge bewertet. Auf einer Skala von 0 bis 100 ist ein Ergebnis von 100 ein völlig sauberer Zylinder.
Die in diesem Test verwendete G-rundölzusammensetzung besteht aus einer Mischung von lösungsmittelraffinierten Mineralölen, die insgesamt etwa 3,5 Gew.-^ überbasisches Magnesiumorganosulfonat, Zinkorganodithiophosphat und ein Bariumarganodithiophosphat enthält. Die Produkte der Beispiele 2 und 3 sind ebenfalls in federn Testansatz in einer Konzentration von 3 Gew.-^ anwesend. Zum Vergleich mit den Produkten gemäß der Erfindung wurde die oben genannte Grundzusammensetzung auch mit 3 Gew.-$& eines im Handel erhältlichen Po3ybutenylbansteinsäureimides von Tetraäthylenpentamin geprüft, wobei die Polybutenylgruppe ein Molekulargewicht von etwa 900 hatte.
Es wurden folgende Ergebnisse erhalten:
Zusatzmittel
keines (nur Grundflüssigkeit) 62
im Handel erhältliches 74
Polybutenylbernsteinsäureimid 84
Beispiel 2 82 Beispiel 3
603809/0970

Claims (4)

Patentans prüche
1. Verfahren zur Herstellung einer Detergensverbindung durch Umsetzung einer Alkenylbernsteinsäureverbindung mit Iris(hydroxymethyl)aminomethan, dadurch gekennzeichnet, daß man die Alkenylbernsteinsäureverbindung mit dem Tris(hydroxymethyl)aminomethan bei einer Temperatur von loo bis 1750C umsetzt, um ein Oxazolinderivat der Alkenylbernsteinsäureverbindung zu bilden.
2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß die Alkenylgruppe der Alkenylbernsteinsäureverbindung 8 bis 3oo, vorzugsweise 2o bis 3oo Kohlenstoffatome enthält.
3. Verfahren nach Anspruch 1 oder 2, dadurch gekennzeichnet, daß die Alkenylbernsteinsäureverbindung aus einem Alkenylbernsteinsäureanhydrid besteht.
4. Verwendung von Verbindungen nach einem der Ansprüche 1 bis 3 als Detergentien in Schmierölen, Schmierfetten, Wärmeaustausch- und Transmissionsflüssigkeiten sowie Treib- und Brennstoffen.
609809/0970
DE19752534921 1974-03-27 1975-08-05 Verfahren zur herstellung einer detergensverbindung Pending DE2534921A1 (de)

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DE19752534921 Pending DE2534921A1 (de) 1974-03-27 1975-08-05 Verfahren zur herstellung einer detergensverbindung
DE19752534922 Withdrawn DE2534922A1 (de) 1974-03-27 1975-08-05 Verfahren zur herstellung von detergentien

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2745909A1 (de) * 1976-11-11 1978-05-18 Exxon Research Engineering Co Kombination von schmieroelzusaetzen
US4116876A (en) * 1977-01-28 1978-09-26 Exxon Research & Engineering Co. Borated oxazolines as varnish inhibiting dispersants in lubricating oils

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US4017406A (en) * 1975-05-01 1977-04-12 Exxon Research And Engineering Company Carboxylate half esters of 1-aza-3,7-dioxabicyclo[3.3.0] oct-5-yl methyl alcohols, their preparation and use as additives for oleaginous compositions
US4062786A (en) * 1976-09-24 1977-12-13 Exxon Research And Engineering Company Lactone oxazolines as oleaginous additives
DE2747608A1 (de) 1976-10-28 1978-05-03 Ciba Geigy Ag Wirksame fluessigkeitszusammensetzung
US4203900A (en) 1977-01-03 1980-05-20 The Dow Chemical Company Process for preparing 2-oxazolines
NZ188418A (en) * 1977-10-03 1981-02-11 Mobil Oil Corp Lubricants containing oil and an oxazoline
CA1133490A (en) * 1978-09-18 1982-10-12 Jack Ryer Molybdenum complexes of ashless oxazoline dispersants as friction reducing antiwear additives for lubricating oils
US4443611A (en) * 1978-12-05 1984-04-17 The Dow Chemical Company Liquid phase preparation of 2-H-2-oxazolines and 2-substituted-2-oxazolines
US4292184A (en) 1979-03-26 1981-09-29 Exxon Research & Engineering Co. Thio-bis-(hydrocarbon-bisoxazolines) as oleaginous additives for lubricants and fuels
CA1148548A (en) * 1979-03-26 1983-06-21 Stanley J. Brois Thio-bis-(hydrocarbon-bisoxazolines) and analogs as oleaginous additives
IT1193212B (it) * 1979-08-10 1988-06-15 Anic Spa Additivi disperdenti per lubrificanti e metodo per la loro preparazione
US4263153A (en) * 1979-10-11 1981-04-21 Exxon Research & Engineering Co. Oxazoline containing dispersants stabilized against oxidation with sulfur and fuels and lubricants containing same
US4374032A (en) * 1980-03-28 1983-02-15 Mobil Oil Corporation Lubricant composition containing borated oxazoline friction reducer
US4295983A (en) * 1980-06-12 1981-10-20 Ethyl Corporation Lubricating oil composition containing boronated N-hydroxymethyl succinimide friction reducers
US4354029A (en) 1981-11-30 1982-10-12 The Dow Chemical Company Preparation of 2-substituted-2-oxazolines with organic zinc salt catalysts
GB2123429A (en) * 1982-05-22 1984-02-01 Orobis Ltd Phosphorus-containing polymeric lubricant additives
GB8407300D0 (en) * 1984-03-21 1984-04-26 Ici Plc Surfactants
US6299655B1 (en) * 1985-03-14 2001-10-09 The Lubrizol Corporation Diesel fuel compositions
US5334329A (en) * 1988-10-07 1994-08-02 The Lubrizol Corporation Lubricant and functional fluid compositions exhibiting improved demulsibility
US5294233A (en) * 1989-02-10 1994-03-15 Nippon Zeon Co., Ltd. Additive for organic medium or thermoplastic polymer
EP0388921A3 (de) * 1989-03-22 1992-12-16 Nippon Zeon Co., Ltd. Additiv für organische Lösungsmittel oder thermoplastische Polymere
AU674052B2 (en) * 1993-05-24 1996-12-05 Lubrizol Corporation, The Pour point depressant treated fatty acid esters as biodegradable, combustion engine fuels

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DE1062253B (de) * 1957-06-29 1959-07-30 Hoechst Ag Verfahren zur Herstellung von aether- bzw. thioaether- und carbon-saeureamidgruppenhaltigen Verbindungen
DE1099263B (de) * 1958-02-26 1961-02-09 Standard Oil Co Motortreibstoff auf Leichtbenzinbasis
NL131916C (de) * 1962-09-28
NL142429B (nl) * 1964-03-19 1974-06-17 Shell Int Research Werkwijze ter bereiding van een asvrije als smeermiddeltoevoegsel geschikte verbinding.
US3533971A (en) * 1967-02-02 1970-10-13 Pan American Tung Research & D Polymer forming composition and electrodeposition thereof
DE1720006A1 (de) * 1968-03-01 1971-05-19 Bayer Ag Verfahren zur Herstellung von Oxazolinen
US3576743A (en) * 1969-04-11 1971-04-27 Lubrizol Corp Lubricant and fuel additives and process for making the additives
FR2052593A5 (de) * 1969-06-16 1971-04-09 Dow Chemical Co
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2745909A1 (de) * 1976-11-11 1978-05-18 Exxon Research Engineering Co Kombination von schmieroelzusaetzen
US4116876A (en) * 1977-01-28 1978-09-26 Exxon Research & Engineering Co. Borated oxazolines as varnish inhibiting dispersants in lubricating oils

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NL7509289A (nl) 1976-02-09
AU8366175A (en) 1977-02-10
NL7509290A (nl) 1976-02-09
AU7922775A (en) 1976-09-23
FR2281422B1 (de) 1978-10-20
AU8366075A (en) 1977-02-10
FR2281423B3 (de) 1978-03-24
GB1513178A (en) 1978-06-07
NL182220C (nl) 1988-02-01
FR2281422A1 (fr) 1976-03-05
DE2512201A1 (de) 1975-10-09
NL182220B (nl) 1987-09-01
BE827198A (fr) 1975-09-26
FR2281423A1 (fr) 1976-03-05
GB1483681A (en) 1977-08-24
GB1483682A (en) 1977-08-24
FR2265771B1 (de) 1980-06-20
FR2265771A1 (de) 1975-10-24
NL7503722A (nl) 1975-09-30

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